A word of encouragement & ways Worklife can help

Dear founders and friends, 

As we head into a period of uncertainty, I wanted to offer both a word of encouragement and a few suggestions for ways that Worklife can help in the coming weeks. 

First things first, I remain incredibly optimistic and excited for every company in our portfolio and our broader category. 

We have a collective vision to reimagine work through better tools and services. Now is our time to shine. 

In the coming weeks, we will experience unexpected demand for our products, increased stress on our technology and new expectations from our users. 

I trust that we will rise to the occasion and we will continue to share insights from our investors, customers, and most importantly our teammates. 

As a reminder, we have a Slack channel and my DMs are always open. Please use both as a resource at any time. 

WorkOS CEO Michael Grinich reminded me today that “any crew can sail in good weather. But it takes a different type of crew to sail through a storm.” 

Please use this time to build a strong internal culture and lean on myself and other investors as questions, concerns and new opportunities to support individual employees arise. 

No ask is too small and we are all hands on deck at this time. 

Secondly, please thank every single person who touches your business. 

Every Engineer, Customer Success Manager and especially freelancers and contractors who face a high degree of uncertainty while juggling multiple projects and clients.

It’s my hope that we continue to build world class cultures and over deliver on our value and empathy for individuals who directly and indirectly impact our business and the value we deliver to our customers.  

A few reminders for the week:

1. Worklife puts people above all else 

Now more than ever, our people are our priority.  

Please check on teammates daily and consider creating a safe space to ask questions on Slack or other internal tools. 

I am available for office hours this week and I will happily join group discussions, AMAs and any efforts to boost employee morale. 

Worklife is calmly and efficiently navigating the uncertainty ahead with a team-first mentality. 

We will be scheduling time with portfolio founders as needed to help with product prioritization, customer introductions and ways to help out in the coming weeks as we navigate changes to our businesses. 

2. Worklife is strategically a focused fund with a collective of sector-aligned operators behind us. 

In the coming weeks, many of us will begin business continuity planning for the first time. 

Over the last few years, we have operated in an ecosystem where capital has freely flowed and many aspects of our business have come together quite easily. 

As the market pulls us in new directions and we begin to re-evaluate our cash flow and core fundamentals of the business, please give Worklife a heads up before making any changes that impact individuals on your team. 

With a nimble, focused fund we are in a unique position to help individuals support multiple portfolio companies or soft land at another Worklife company with a shared vision and team culture. 

We’re here to help and we are committed to every individual that’s joined us on this journey so far. 

3. Worklife will continue to operate with the same commitment and level of service to our portfolio companies and the broader ecosystem of operators who are reimagining work through better tools & services.

Venture firms share a lot of similarities to enterprise and workplace tech, we are only successful if the companies we serve are equally as successful. 

I am incredibly thankful to have invested in your company and continue to be committed to help you grow, even in the most uncertain times. 

In the coming weeks, please use myself and our collective of operators to help you if you feel unsure at any point in time or simply want a second opinion. We’re here to help and my number is below. 

Onward and upward,


Building a better work life together.

With a new, specialized fund, our goal is to partner with founders at the earliest stages and provide more than just capital.

In the coming weeks, we’ll share more on our strategy, investments to date and growing community of designers, developers and friends of the firm.

But here’s a little preview of what’s been happening behind the scenes.

Our recent investments include:

  • Developer tools: collaborative coding environments, robust no-code solutions for developers and technical marketers and product managers and video game-like productivity tools.
  • Design tools: 2D animation tools, freemium photo and video editing tools that start with a better Instagram and scale into mobile friendly alternatives to expensive tools like Adobe.
  • Professional networks: a recommendation engine for finding freelancers and full-time employees for a specific skill or expertise, a social network for developers, a modern media company for female founders and more.
  • New platforms for launching a business: a creator platform for custom jewelry, a fully-customizable platform for launching your own subscription business.

We’re not just B2B (really), we love consumer but selectively look for opportunities where we can be most helpful:

While we love consumer, we typically look for signals that individuals will use your core technology to launch new companies, ship better features or improve their work life. 

We look for an open ecosystem where your technology will be used by developers and your core technology has the potential to become a new technology standard or operating system for your industry. 

ie: it’s difficult for us to invest in individual gaming studios given our fund size and commitment to LPs, however we’d love to find the next Unity or Roblox.  

For creator tools, we look for technology that starts with an early group of smaller creators, but ultimately delivers value for small to medium sized businesses.

ie: If you’re building the next Shopify, we’re most helpful if you plan to become the core technology for traditional retailers (Shopify Plus) and want to build an open ecosystem where new businesses will be built on top of your platform ie: customer support, shipping/logistics and other e-commerce services.  

For LPs, co-investors and finance folks, our official name is Work Life Ventures. 

We believe capital is a small piece of what we offer, so we invest flexibly from pre-seed to series A with an initial investment of $100,000 to $250,000.

For designers, developers and other friends of the firm, you can call us worklife. 

We like to keep things pretty casual: our emails are brief, events are worth your time and our companies are always hiring.

We believe the best career opportunities happen at the intersection of what you enjoy doing and where your work can have outsized recognition and impact on the business.

We believe that individual product designers and developers (yes, you and you alone) can have meaningful impact on the future of work by writing code and moving pixels for companies at the earliest stages.

When you think of workplace software, you probably think of Oracle, Salesforce and enterprise giants with pretty poor product design.

With your help, we’re here to change that. 💪

While many enterprise companies use stick figures and humans of flat illustrations, we prefer to use photos of real people.

Our logo looks like this  

It’s Regola Pro. You’re welcome to use it and change the color of the dot. 

In the coming weeks, we’ll be sharing more from our growing team including our new additions to the team: our first Engineer and Editor.

More to come!

The hard work for the oversubscribed

My interview with Nathan Baschez on the momentum required to back the best founders

In today’s funding environment, founders have a lot of options when it comes to raising early rounds — operator-angel funds, alumni syndicates, celebrities and growing seed programs at Sequoia, a16z and most multi-stage firms in Silicon Valley.

For repeat founders & A-teams, fundraising feels like a fast game of Tetris where every name/allocation on the cap table must deliver a high value per $ invested — relevant operating experience, strategic alignment with early customers, strong signal for the next round. The question is never can you raise, but rather what is the minimum allocation you can offer without losing their attention and access to their network.

I recently joined Nathan Baschez for an in-depth interview on how I built WorkLife and the momentum required to invest in the best founders and inherently the most oversubscribed and competitive rounds from the earliest stage.

I hope discussions like these encourage more operators to find new ways to give back to the startup ecosystem and give founders a fresh perspective on how to drive a highly efficient fundraise where each name on the cap table becomes a core part of your early team.

Brianne Kimmel’s Momentum Investing

How the founder of WorkLife Ventures built one of Silicon Valley’s most sought after emerging funds from scratch.

Brianne Kimmel knows how to drive a wedge into the market, and parlay it into lasting momentum.

Exhibit A: her investing career.

It’s incredibly hard to break into the market as a new VC. There’s a sort of double chicken-and-egg problem: great companies want investors with proven brands, but in order to build a proven brand, you need to invest in great companies. A similar dynamic exists on the LP side: in order to prove yourself a good fund manager, you need experience managing funds.

Most investors solve this “cold start” problem by working their way up through the ranks at established VC firms, then branching out on their own. But Brianne carved her own path.

She’s built a distinctive brand for WorkLife, the first enterprise fund focused on the consumerization of enterprise, investing in companies like Webflow, Voiceflow, Tandem, Command E and 20+ others.

Her early investors include Zoom CEO Eric Yuan, Slack CEO Stewart Butterfield and executives from breakout SaaS companies like Dropbox, Slack, Twilio and Zendesk. 

Her fund advisors include the original super angels: a16z founder Marc Andreessen, Felicis founder Aydin Senkut, Meritech founder Rob Ward and Floodgate’s Mike Maples

The story of how she did all this is a masterclass in strategy and momentum.

How Brianne positioned herself to start investing 

In addition to operating full-time, first at Expedia and later at Zendesk, I started advising startups when I was teaching at General Assembly in Sydney. It worked well for me because I was an expat with free time on nights and weekends. When I moved to San Francisco, I continued teaching and ultimately taught over 5,000 students in four years. 

This was a great way to build expertise in early stage growth marketing and GTM strategy. General Assembly served as an especially good platform for building a personal brand by leveraging their global social channels and mailing list, which I used to build momentum and spin out to launch my own program SaaS School. 

As I continued to advise early stage startups and build relationships with both founders and VCs, my appetite for investing grew. 

My first week at Zendesk I was asked to fill out a career card which highlighted my professional goals over the next ten years, which included a plan to move up the ranks as an operator and wait ten years before making the jump to venture. 

Soon after that, I decided to accelerate my transition to investing, which led to a shift in my strategy where I chose to optimize for startup-facing projects inside Zendesk and double down on community-building events on evenings and weekends.

I also discovered a few tactical ways that to build my VC network: 

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Fund I: the friends & family “round”

Emerging funds are a lot like startups, in that your first fund (“Fund I”) looks a lot like a friends and family round. Even if you are a successful angel investor, you are still unproven as a good steward of other people’s money. 

To raise my first fund, I first activated my co-investor network and my portfolio CEOs who could vouch for my working style and my ability to access great companies and provide portfolio support in scalable ways. Then, I exported LinkedIn contacts and emailed sector-aligned CEOs and executives in my network. I also changed my Twitter bio to: “Thinking about starting something new. DM me for deck,” which generated inbound interest from followers in the startup ecosystem.

I gathered all of these cold emails and inbound requests then started socializing my fundraising deck. It was a good way of getting people involved from day one and it turned out to be effective.

When I went to raise my fund, I had several things going for me:

  • Angel investor in a number of early stage companies that “didn’t need my money,” including Webflow (recently raised $72M from Accel), Airgarage and Command E.
  • A strong point of view of GTM for early stage enterprise companies, especially helping product-led companies identify new opportunities for growth. 
  • A large community of early stage founders from starting SaaS School, building Zendesk Apps Marketplace & Zendesk for Startups and investing in professional networks like Dev.to, Girlboss and Webflow. 
  • A trusted network of co-investors I had developed from angel investing and a growing portfolio with sector-aligned founders and early employees who quickly help founders navigate specific challenges and pivotal moments for the company.

The combination of these helped me raise my first $5 million in 2.5 weeks and continue raising to grow the total fund size. My initial deck I used has now been viewed over 30,000 times.

Building a foundation for institutional LPs

To scale into a larger fund size, you will have to move beyond friends, family and high-net worth individuals and pitch family offices and institutional Limited Partners (“LPs”). In the same way that venture capitalists aim to buy a percentage of a company, LPs typically invest based on a percentage of total fund size and seek to build a concentrated portfolio across a number of top-tier funds. 

What’s interesting about institutional LPs is how they approach building a portfolio across different asset classes ranging from real estate, private equity and in recent years a growing interest in venture capital. When it comes to institutional LPs, venture capital firms are competing against more mature, stable asset classes and seek to find LPs with established venture portfolios. 

(Image via the The State of Family Offices 2019)

I chose to launch with a two-prong strategy to build an enduring platform that scales into institutional LPs: 

  1. Have sector-aligned CEOs get involved from the very beginning, including Eric Yuan from Zoom, Stewart Butterfield from Slack, Clark Valberg from InVision, Nick Mehta from Gainsight and many more. 
  2. Learn from “super angels” who started their own funds and managing directors of top-performing funds. 

LPs will ask about hiring, day-to-day operations and core mechanics of the firm to de-risk their investment and I’ve found a strong alliance with sector-aligned CEOs and managing directors of top-performing funds has been an effective strategy for establishing a strong reputation in the sea of new seed funds.

The best VCs have an identity and a strong point of view 

In the early stage landscape today, there’s no shortage of network-based $1M-$10M micro-funds. These funds build credibility based on broad access to early stage companies and maintain an “ears on the ground” status where they seek small allocations in companies that have heat in the market, meaning multiple venture firms are trying to invest. This can be an effective strategy to get started, however it can easily lead to groupthink and a more transactional relationship with founders after the round closes. 

With a sector focus and a strong opinion on GTM, WorkLife provides a series of programs and services to help early stage companies develop their market entry strategy (top-down, bottom-up, open-source, closed beta vs. open freemium) to accelerate their time to product market fit.  

The most public-facing program is SaaS School, an invite-only program for founders to learn from executives at Airtable, Drift, Dropbox, Notion and more.

An effective model for a focused fund is Forerunner, which built a highly differentiated brand and hit significant momentum with a concentrated focus on direct to consumer companies for its debut fund. Forerunner has since expanded into marketplaces and SaaS with a unique angle on commerce infrastructure, thanks to early investments in companies like Away, Glossier and more.   

Another example is Founders Fund’s unique focus on big, non-consensus ideas (their manifesto talks about space, transportation, and biotech). It serves as a beacon, both for VCs and founders. 

Daniel Gross at Pioneer Fund also has a model I love. As a founder and friend to young, unproven founders, Pioneer makes bold bets based on individual potential and whitespace in frontier sectors. Through his personal story, he speaks well to “lost Einsteins”. His messaging helps Pioneer invest in big ideas from day one and attract young talent who are looking for a way to break into Silicon Valley tech circles.

Discovering WorkLife’s identity

WorkLife’s identity started as a collaboration with creators and exploration of the many ways that technology can create new industries and revive old ones.

Folks like O.G. streetwear creator Bobby Hundreds, revolutionary Instapoet Rupi Kaur, and repeat founder Arianna Huffington helped turned WorkLife into something much bigger than early stage enterprise focused fund.

Whether you’re a mixologist at Soho House, a traveling tattoo artist on Instagram or back-end engineer at a big tech company, WorkLife is reimagining work through better tools and services. 

We believe as the world becomes increasingly technical and creative, there will be a thriving ecosystem of new tools and professional networks for consumers, prosumers and enterprise uses cases. 

[Editor’s note: this is a great example of “competing to be unique,” instead of “competing to be the best.”]

A gap in the market

After spending 12 months in the ecosystem meeting consumer and enterprise VCs and entrepreneurs, I noticed a very clear divide between the enterprise partners and the consumer partners where my portfolio companies struggled to connect with either. 

The enterprise partners typically come from a traditional enterprise background and have deep expertise on top-down strategies with an emphasis on sales and marketing and less on product-led growth with an engineering mindset. 

While the consumer partners are spending more time on gaming, eSports, celebrity-founded companies and other emerging interest areas for the everyday consumer. Very few had deep specialization on consumer trends in the workplace. 

In most cases, bottom-up workplace tools and professional networks meet with both the consumer and enterprise partners to get a balanced perspective of consumer acquisition and product-led growth in addition to early enterprise GTM. 

However, increasingly we’re seeing firms hiring a dedicated SaaS partner. For example: Slack’s first Head of Growth Merci Grace, now Lightspeed, and early Evernote Head of Product Naomi Ionita, now Menlo Ventures, who both made the move to venture in the last 18 months.

The thesis: future of work

The consumerization of enterprise in its simplest form asks: What are the tools and services that everyday people need to do their job well? What “BYOT” (bring your own tech) will consumers bring to work, share with teammates, and take with them to the next role?

I have a theory that any workplace product that is ten years old is ready to be unbundled into a new ecosystem of newer, more consumer-friendly tool. 

LinkedIn, Adobe and Zendesk are currently being unbundled, without facing immediate disruption, because their independent market sizes are large enough to support many $1B+ companies. 

Using Zendesk as an example: Freshdesk, a fast follow copycat came first, then Front, a shared inbox for teams, and Kustomer, “Zendesk for retail and e-commerce companies.” 

With enterprise, the problem is already known and the market size is typically large enough to support a growing ecosystem. Enterprise founders can also expand their market size by building complementary products and selling them as add-ons, and developing new buyers and use cases as the market matures.

The future of work needs more than software

In addition to workplace software, WorkLife also looks at labor marketplaces and new ways for people to make money. 

For example, think of a high schooler who wants their first job. They have to drive from store to store to hand out a paper resume, which shows little to no work experience or references. 

To solve the problem, Heroes (a WorkLife portfolio company) created a TikTok-like video application for hourly workers to apply for customer-facing roles. Companies on the platform—Starbucks, H&M, Panda Express—care most about people who can be customer-facing. And video is a great way to show if you can be personable and are aligned with the company’s mission, values and culture. 

I’ve also invested in managed marketplaces such as Tend. If you’re a mixologist and work somewhere like Soho House, access to additional work is really hard. It’s not as simple as picking up additional shifts (unless you want to work at a dive bar down the road). Tend builds a marketplace to manage these highly-skilled hospitality and entertainment workers and help them get additional hourly shifts.

From WorkLife’s Instagram: @worklifevc

Brianne’s advantage: competitive analysis

Taking a high-level view, there are four stages to venture capital: sourcing, picking, winning, then post-investment support. 

Sourcing can come from writing, blogging, and hosting events—but it’s actually been fairly commoditized. A lot of us in the Bay Area share the same hyper-connected networks where everyone knows everyone. 

As a result, I spend most of my time on picking, which in many cases means cold emailing and finding introductions to companies based on a thesis or unique insight. 

Typically, when I meet a startup, I will proactively reach out to every other similar company. While some say this isn’t important, I think having a focused strategy around competitive analysis is critical for pre-seed and seed stage investing. Great ideas come in bunches, and oftentimes you will quickly uncover three or four entrepreneurs that are solving the same problem with a similar solution. 

When you prepare for a meeting and come with original research and context, it helps drive a much deeper discussion and get to an investment decision much faster. I find this alone has been a differentiated way to remove the reactive tendencies that potentially come up in seed, so I focus more on outbound than inbound introductions.

For example, before I even met with Tandem, I met all the competitors in the space. And post-close, I even joined a dinner where all the competitors got together. It was really fascinating to see that even though seed stage companies are potentially competing, they often want to get to know each other to determine to what extent they’re competitive and to what extent can they partner together in the future. As companies tend to evolve so quickly before they find product-market fit, it’s beneficial for founders to build relationships and meet their peers to understand their place in the ecosystem better. 

A bit of tactical advice for founders: invest in relationships today that will help you tomorrow.

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As an operator turned angel investor, my goal is to share tactical advice and help more operators build a track record on evenings and weekends. 

After 12+ months of research, dozens of angel dinners and a new micro-fund, I shared the Angel J-Curve, a framework for operators w/ tactical advice to build & scale your angel portfolio.

I hope essays like these help others found companies, break into investing, and supports the ecosystem’s overall growth.

The 2020s will foster a thriving creative scene like the Roaring Twenties.

Adobe’s market cap, Netflix stock & new opportunities for creator tools

As we close out the year and welcome a new decade, I took some time over the last few days to reflect on the major cultural shifts that have defined the past decade and study market signals on what’s to come.  

Here’s the Tldr: The 2010s will be remembered for transformational changes in the physical world brought to you by SoftBank, while the 2020s will foster a thriving creative scene like the Roaring Twenties.

Relax, old sport.

The Roaring Twenties 2.0 will be mostly positive for a few reasons: 

All eyes are on Adobe, but it’s still too f*cking expensive. 

Adobe will serve as a positive signal to the public markets with a market cap larger than Salesforce and plenty of new opportunities for prosumer and professional-grade tools because Adobe is still too expensive and will keep going up

Original content will continue to be king as we binge our way into the nouveau niche genres.

Netflix, the top performing stock of the decade, gained more than 4,000% as it disrupted the media industry with its video streaming platform. 

We’ll see even more original content and new, niche genres from the modern media giants Amazon, Netflix and now Disney+, while simultaneously facing the impending doom of our already shrinking attention spans when Quibi’s ‘seven to ten minute bites’ launch on April 6, 2020.

Everyone’s a creator = $$$ for the design stack. 

Individuals will pay out of pocket to produce better creative content — a catalyst for new tools across consumer, prosumer and professional-grade use cases — many venture-scale businesses will emerge.

(more to come on new opportunities and companies to watch in the design gold rush coming next week.)

Sadly, most consumers will monetize a small, but loyal base of followers to cover the operating costs for producing original work, while they continue to work full-time in less exciting occupations.

The same “rugged individualism” described in the Roaring Twenties 1.0 will drive dinner party discussions in the Roaring Twenties 2.0 where individuals will discuss their podcast, newsletter, creative endeavors and angel investments while quietly working normal jobs.

Meanwhile and somewhat contrary to popular belief, creatives and freelancers will face insane anxiety and see little to no financial upside in exchange for their full-time independence.

As consumer spend for luxury software including personal productivity, podcasting, design and other personal tools increases, so will the new opportunities for fractional ownership of luxury in the real world. Rally Road for cars, Otis for art and other technology companies owning various parts of the dinner party discussion stack.

Overall, quality of life has never been better.

Celebrities defend their position on current platforms and break out as angel investors, venture capitalists and venture-backed founders.

In the same way vaudeville performers seamlessly transitioned to the film industry with larger crowds and bigger salaries, celebrities will continue to have outsized distribution advantages on any new creative platform and create a high barrier to entry for new creators.

Celebrities will defend their positions on Instagram, TikTok and existing social platforms, while breaking out with their own venture-backed startups and early stage VC funds.

“Can a celebrity get innovation before a creator gets distribution?” In most cases, yes. Triple threats, especially Hollywood angels, are the future of early stage investing:

I joined @HarryStebbings on 20VC to discuss Super Angels 2.0:

Original “Super Angels” @pmarca @m2jr @asenkut went on to start @a16z, @floodgatefund @felicis

“Triple threat” angel investors are the future of early stage investing: operator, angel, influencer

Some highlights:

— Brianne Kimmel (@briannekimmel) October 14, 2019

Expect more celebrity-backed startups, new independent VC funds à la Serena Williams, Will Smith, Karlie Kloss and a16z-like Cultural Leadership Funds where celebrity LPs co-invest alongside institutional investors.

What we’ve learned in the last decade:

1. The “Industrial Revolution” brought to you by Softbank is cooling down for now.  

The ease of calling a car from your phone.

The convenience of ordering a healthy meal that arrives in 20 minutes or less. 

The freedom of flexible office space and “video conferencing that doesn’t suck.”

2010s will be remembered for its convenient services that impact our quality of life. 

We’ve seen incredible location flexibility and productivity gains driven by the sheer number of WeWork offices in 99 cities and 26 countries combined with Zoom’s ability to consistently deliver “video conferencing that doesn’t suck” that has scaled into 5 billion monthly meeting minutes and a $100M IPO. 

We’ve also seen Uber and WeWork — arguably the two most influential and transformational companies for daily life — face a great deal of public scrutiny for gross mismanagement magnified by voices on social media and the overall capital intensive nature of the businesses.

Outside of the investing world, consumers haven’t noticed — or cared — that WeWork and Uber cost SoftBank’s Vision Fund a quarterly loss of $8.9 billion.

Consumers will continue to use SoftBank-backed services and new market entrants will struggle to raise enough venture capital to compete with well-funded giants as investors shift focus to higher margin businesses. New market entrants will serve as small acquisition targets and struggle to scale into $1B+ stand-alone businesses.

On the bright side, we’re patiently awaiting both Uber and WeWork’s highly anticipated films. An itch we haven’t scratched since the debut of two Fyre Festival documentaries in early 2019. 

2. The capital intensive giants will mature with help from big tech leaders. 

Capital-intensive businesses will scale with help from big company operators who can cut overall operating costs, expand into new markets and launch new lines of business to unlock additional revenue streams. 

3. The early builders transition smoothly to B2B.

Early product builders at capital-intensive consumer tech companies will transition smoothly to higher margin workplace software by productizing internal tools they’ve previously built and applying high-growth consumer best practices to professional-grade products and legacy tools.

I’m betting on the consumerization of enterprise and why outsiders (consumer product builders) are likely to build the next great product at work.

“The next generation of applications for the workplace sees people spinning out of Uber, Coinbase  and Airbnb,” 

“They’ve faced challenges inside their highly efficient tech company so we are seeing more consumer product builders deeply passionate about the enterprise space.”

Where we’re going in the next decade: 

  • “Rugged individualism” will drive dinner party discussions: individuals will discuss podcast, newsletter and creative endeavors before full-time work, however few are actually thrive in their creative endeavors. 
  • In the same way vaudeville performers were recruited by the film industry for larger salaries and more distribution, celebrities have outsized distribution advantages on any new creative platforms, which create a high barrier to entry for new creators. 
  • Many successful companies will be built on the back of Creative Capitalism across consumer, prosumer and professional-grade use cases, individuals will pay out of pocket to produce better creative content. Most will monetize a small base to cover the operating expenses for creative work while continuing to advance in their full-time occupation.

Up next week: New opportunities and companies to watch in the design gold rush

My pitch to Marc Andreessen, Zoom CEO Eric Yuan and investors in Worklife.

As an operator and active angel investor, I left Zendesk a year ago to build Worklife, a future of work focused fund, backed by Silicon Valley investors and executives from breakout $1B+ companies.

While there are many paths into venture, I’d like to share my background, fund strategy and how I raised $5M in just two weeks (and chose to raise $10M based on a lot of interest from other sector-aligned founders) to help other operators, angels and emerging fund managers break into what I consider to be one of the most high impact and meaningful jobs in the world.

It’s an honor and a privilege to partner with founders on the long road to success. If nothing else, I hope this post inspires you to get involved with early stage companies in some capacity. Startups require so much more than capital to be successful.

  1. How to start angel investing
  2. Why start a fund?
  3. The pitch

The pitch is an early version of the deck that closed Marc Andreessen, Zoom CEO Eric Yuan and Silicon Valley investors and executives at Dropbox, Slack and other 🚀companies.

How to start angel investing

Like many angel investors, I got started by meeting early stage on evenings and weekends, while I was operating full time at Expedia and later Zendesk in various product roles and lastly in a GTM strategy role where I built Zendesk for Startups which included a network of incubators, accelerators and VC firms.

In addition to operating, I taught classes at General Assembly for over four years and built my own GTM bootcamp as a way to expand my reach and build a trusted network with 5,000+ operators in the Bay Area (many have gone on to start companies).

I then decided to rebrand the program as it’s own stand-alone entity and call it SaaS School, a self-funded & community-led program taught by executives from Airtable, Dropbox, Notion, Superhuman and other venture-backed startups.

In my recent interview with TechCrunch, I shared that “you start by advising, then you start with very small angel checks.”

Today, there are a number of programs to get started ie: First Round Angel Track, AngelList Spearhead (up to $1M for founders) and most VC firms operate their own variation of scout program.

In the beginning, I used my own capital to invest in early stage companies including Webflow, Command E, AirGarage , but most importantly I sent a high volume of companies to VC funds.

Through Zendesk for Startups, SaaS School and other events I hosted, I became a super-connector in Silicon Valley.

I would take the first meeting and help founders find their lead and access other angels in my network.

A few thoughts for those who are just getting started:

  • Access is everything when you’re just getting started: meet a lot of companies and start to narrow your filter over time
  • Lean into existing networks: Venture capital is an industry built on trust and reputation. Your reputation with colleagues and peers at other companies matter a lot, especially as they leave to start companies or you want to recruit them to your portfolio companies
  • Give, give, give before you ever ask for anything: Before raising a dollar for my fund, I had taught over 5,000 students, hosted weekly startup dinners and jumped on diligence calls when firms had questions that aligned with my experience in SaaS growth and GTM

Why start a fund?

While there’s no shortage of scout programs or ways to play an active role in the early days of a startup, I chose to start my own fund for three reasons:

  • Values alignment: People spend 1/3 of their lives at work. Technology has the power to create new jobs, improve existing ones and give people more control over their career progression without employer dependencies.
  • Market opportunity: “I had friends like Ryan Hoover,  who started Weekend Fund focused on consumer, and Alexia is one of my friends as well and I saw what she was doing with Dream Machine, which is also consumer. It felt like it was the right time to come out with a SaaS-focused fund.”
  • From SaaS School alone, I see 200 applications twice a year from Seed and Series A founders. There was increasing demand from the community for a dedicated program to technical/product founders learn GTM best practices from leading experts.
  • Skills alignment: The ability to partner with founders where I can immediately add value through operating experience, network and general interests was a core driver for not joining a firm. I wanted to stay focused and continue to develop my craft as a bottom-up SaaS and workplace product expert.

The Pitch

Worklife is a future of work focused fund not tied to “Consumer” or “Enterprise” labels, but rather focused on new tools and services to unlock individual potential through creativity, productivity and new types of work.

Here is an early version of the deck that I used to pitch early LPs.

Overview: bullet points to describe the fund strategy and high signal LPs involved

Fund I has a fairly high number of investments by design.
The goal is to build a broad network that aligns to my core thesis. I’m anticipating 70% of companies will fall under the “work” category and 30% will fall under “life” such as education, childcare and services that are consumer, but directly impact your work life.

Fund I has a fairly high number of investments by design.
The goal is to build a broad network that aligns to my core thesis. I’m anticipating 70% of companies will fall under the “work” category and 30% will fall under “life” such as education, childcare and services that are consumer, but directly impact your work life.

About slide: value proposition to founders, achievements and fund differentiators 

Market opportunity: Define the market opportunity and provide examples of companies that align to your thesis.

In this case, my LP base is focused on Silicon Valley investors and executives with deep expertise in the space, so this section is fairly light.

Theme slides: A key trend, unique insight or thought that demonstrates access, expertise and ability to win deals aligned to the theme.

In this case BYOT is a term I coined to describe tools that people discover on evenings and weekends, bring to work and land & expand inside of companies.

For creative tools such as podcasting, publishing, design platforms for architects, jewelers, graphic designers and animators, these tools grow through influencer adoption and social mentions, industry communities and creative agencies/freelancer platforms.

One of the core pillars of @WorkLifeVC is new technology that reimagine work.

The greatest innovations we’ll see in the workplace will come from new consumer tech that people discover & use daily to improve their work life. Technology gives consumers more leverage to advance their career without employer dependencies.

People want more ownership over their career and flexibility to seamlessly transition into new sectors and areas of expertise

People (not employers) will solve problems like career progression.

Affordable skills-based education is giving people more ownership over career progression @LambdaSchool and @WhiteHatGB accelerate & launch high earning careers not possible before @knowablefyi@superhi_ for ongoing learning to accelerate careers or start something new.

Online communities and forums create a compressed learning environment & safety net for members – Peers share insights and validate ideas – Members collectively refresh content & moderate – Safe space to job hunt or start something new @ThePracticalDev@girlboss

Professional coaching, on-demand advice & remote workspaces create new outlets for people to break into a new field Interests snowball into careers: self-education & consistent publishing to build expertise Interest based calls like Dial-up https://dialup.com

GTM for software companies is increasingly similar to DTC brands: brand matters, community reduces customer acquisition costs and customer support costs and social signals drive purchase decisions over pure functionality.

Your work life is part of your identity.

For early builders, you’ll have periods with long hours and insane focus but at the end of the day you’re building what you love.

As you scale, keep in mind: people spend 1/3 of their lives at work, it’s a big part of who we are and how we view the world.

The modern workplace is a community with shared values, a discovery platform for new goods and services and a trusted source for news and information.

Offices are designed for Instagram.

Employees choose companies based on benefits and services.

Companies compete on culture.

I recently told Harry Stebbings on 20 Minute VC that “great company cultures aren’t coincidental. It requires insane focus and a commitment to company values.”

Fund Strategy slide: A clear definition for how you plan to source, pick, win and support companies.

Track record: List angel investments and advisor roles to demonstrate both access and deal judgement.

In this case, Webflow had received raised a $72M Series A from Accel and all angel investments were alongside top-tier firms or high-signal angels in the cases where I invested before a priced round.

Personal brand: What are you known for in the ecosystem? Why would they pick you over other angels and micro-funds?

Access & Scale: How do you currently meet founders? How will you help your growing portfolio with limited resources?

Fund strategy: target fund size, average check size, carry & management fees

Strike zone: What companies and align with your thesis and fit within your strike zone of sourcing, picking, winning and supporting.

Note: LPs also look for examples of companies outside of your strike zone, however I have removed outside strike zone slides to avoid any signaling risk for founders.

If you’re an angel investor, scout or first time fund manager, I’d love to connect and compare notes.

I host monthly dinners for emerging managers and frequently share best practices for angels and emerging fund managers on my blog and Twitter @briannekimmel.

Why ex-Airbnb, Coinbase, Uber will build the next $1B+ workplace product

In a recent interview with TechCrunch, I shared why I’m betting on the consumerization of enterprise and why outsiders (consumer product builders) are likely to build the next great product at work.

“The next generation of applications for the workplace sees people spinning out of Uber,  Coinbase  and Airbnb,” 

“They’ve faced challenges inside their highly efficient tech company so we are seeing more consumer product builders deeply passionate about the enterprise space.” Read more here.

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Prior to joining Zendesk, I was on the buy side running nearly a dozen RFPs per year and putting tens of thousands of SaaS dollars on a corporate credit card each month.

I spent 4 years at Expedia scaling from a performance marketing role into the Head of Social Media, which owned acquisition, engagement, customer support (on-shore and off-shore with a tiered escalation strategy) and community (a growing team of in-market brand managers + translation experts).

Expedia, like many high-growth tech companies, have a “do everything in house culture.” We hired SEO, SEM, FB and Customer Support specialists and gave them freedom to choose their own tools. We rarely used agencies and we taught individual contributors how to purchase tools without engaging procurement (within reason and with a goal of freeing up procurement to focus on higher profile projects).

After 4 years of deeply analyzing tools and in some cases engaging internal engineers to build our own, I made the leap to full-time B2B by joining Zendesk to scale the product portfolio from one to seven products include live chat, analytics and tools beyond the core help desk ticketing software.

If you’re thinking about building something for the workplace, here’s what you should know

⚠️ Caution: Tough feedback ahead ⚠️

  1. In the early days of the company, things will come easy.

It feels a lot like building a consumer product, but maybe better (early users pay $) Keep in mind: these users are the easiest to acquire Selling to other startups is a great strategy, but that well easily dries up

Startups churn at a higher rate & have a lower expansion rate. I wrote about the challenges of a purely self-serve business here

2. Purely self-serve businesses are easily commoditized.

Think you’re the only “product person” working on this problem?

You’ll quickly uncover others, especially as you are out fundraising.

To quote @davidu: “Good ideas comes in bunches.”

Some recent example: Tandem/Around & Linear/Height

3. Sales is an achilles heel, figure it out sooner rather than later.

Behind closed doors, every self-serve SaaS companies talks about revenue they missed by not figuring out sales sooner.

Find an advisor who has done it before and build the muscle before you need it.

Keep in mind: Dropbox created whitespace for Box. Microsoft Teams fast followed Slack with an enterprise-grade product.

4. Hiring will get harder and your company culture will change.

Self-serve is a life phase and you’ve chosen to build in a space with an evolving business model I call it “horses for courses”

The people you hire today are likely not the same people you’ll have around in later funding rounds

On the product side, product people love joining self-serve SaaS businesses. But once the core tech is built, those same people don’t want to be handed feature requests from large customers.

Read: Enterprise Products Vs. Consumer Products

On the sales side, there will always be challenges If a sale team doesn’t hit their quota, guess what? They’ll leave for a company where they will In the early days, I suggest a Head of Sales and Customer Success someone who can partner directly with founders.

But eventually, you’ll need to layer in a more traditional sales org If you’re a product person, this will feel uncomfortable Company culture will change and guess what? You’re now running a real B2B company.

As you think about the transition from consumer to workplace tech, talk to folks who have made the switch Be mindful of the changes that come with a constantly evolving business model.

5. The day-to-day doesn’t scale well, that’s the point.

Somedays it will feel like a consumer business, other days you’re flying across the country for one meeting.

But trust me, you’re not flying to SXSW… You’re going to Newark, San Jose, Omaha and Orlando for conferences

You will have to fly to meet customers, save customers and speak at industry events. Welcome to the wonderful world of B2B!

For more thoughts on early stage company building, especially SaaS business models, please subscribe to my newsletter.

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Turn unused space into extra income with AirGarage

Announcing my investment in AirGarage, the first API for physical space starting with parking lots

“This land is your land, this land is my land From California to the New York island From the Redwood Forest, to the gulf steam waters This land was made for you and me”

As the old song reminds us, America is a land filled with forests, streams and wide open spaces from sea to shining sea.  

But if we’re honest, the average American sees more potholes than palm trees on any given day.

In urban metro areas, parking lots cover up ⅓ of the land area, becoming the single more salient landscape feature of our built environment.

Los Angeles alone has 18.6 million parking spaces, which adds up to 17,020,594 square meters of land.

This adds up to more than three parking spaces for every vehicle in the city.

A breakdown of parking spaces in Los Angeles

For business owners, parking spaces and larger lots are underutilized assets.

Hotels in particular require fewer parking spaces for guests as 52% of all work-related ground transport is now booked through ride-sharing apps.

Moving outside of cities, we see sprawling church parking lots, university campuses and industrial parks in suburban and rural areas.

In these regions, there is more available land than demand for parking, which create larger spaces for public use such as school fundraisers and community events.

But renting the space requires additional bookkeeping and vendor management to both maintain the space and get paid for each event.

This is why today, I am thrilled to announce my investment in AirGarage as part of a round co-led by Founders Fund and Floodgate with support from Ryan Delk, Ryan Hoover and other angels.

AirGarage is a real estate company building the first API for physical space starting with parking lots.

Organizations of every kind including churches, hotels and businesses use AirGarage to handle lot enforcement, payments, and visitor registration. It’s an easy way to passively earn extra income by renting out their unused space.

For consumers, this means fewer parking monopolies, more available spaces at better rates, especially in urban metro areas during periods of peak demand such as conferences and sporting events.  

The AirGarage founders embody what it takes to build a disruptive real estate technology company with a deep understanding of the problem today, aligned incentives for landowners and consumers, and a technology layer that serves as foundational infrastructure for new companies such as cloud kitchens, pop-up retail experiences and group based fitness activities.  

A converted parking lot in Downtown Los Angeles

In a world that’s increasingly multi-modal with bikes, scooters, one-wheels and more, AirGarage is well positioned to help landowners unlock revenue from parking today and create entirely new experiences for everyday people in years to come!

AirGarage dashboard view

If you’re a landowner who wants to make extra money for your space, schedule a demo to learn more.

Kylie Jenner, Joe Rogan and the new American Dream

I recently joined the Square One podcast with Romeen Sheth to discuss the latest trends impacting the way people work.

In this episode we’ll discuss three themes that I’ve been actively exploring as an early stage investor:

The new American Dream

How creative expression, online influence and extreme optionality ie: remote work, calendar flexibility and the freelance economy is changing how Americans define success.

YouTubers and Twitch streamers

The age of the individual   

How the gig economy exposed a need for better tools for freelancers and side-hustlers including personal finance, productivity tools and new economic opportunities for blue-collar and white-collar workers.

And why customer support is a good analogy for augmenting (and not automating) knowledge work.

Founder as a service 

Following events like Fyre Festival, we’ve seen Distrust Go Viral and a shift away from pay-per-post influencers to a new generation of creators.

In the next wave of online influence, celebrities will launch their own brands and move away from paid posts and collaborations w/ legacy companies.

Kylie Cosmetics is worth $1B+ w/ only 12 employees!

How 20-Year-Old Kylie Jenner Built A $900 Million Fortune In Less Than 3 Years

With Shopify, we saw the ability for anyone, anywhere to create their own e-commerce company.

In future, we’ll see new platforms for celebrities, influencers and aspiring creators to build just about any type of tech-enabled business.

Listen to the episode or skim the full conversation below.

But first, sign up to get future essays delivered to your inbox:

You’re listening to Square One, a podcast where we interview entrepreneurs, investors, and executives at the cutting edge of business.

I’m your host, Romeen Sheth. Today’s guest is Brianne Kimmel, network leader at Village Global.

Scale and reach are off the charts today. Joe Rogan gets more views than CNN, Kylie Jenner’s dominating cosmetics with less than 30 employees, and Conor McGregor can sell more pay per view than UFC.

But with access comes real responsibility. Fyre Festival is the latest SNAFU to fall trap to this. So what’s going on?

Romeen Sheth: The age of the individual is on the rise, and AI is automating away old world jobs while increasing leverage for new world jobs.

This paradigm shift is causing us to reimagine work. What does it mean to participate in the workforce?

How will we interact with one another, and what are the skills of the future?

Welcome Brianne, and thanks so much for joining us.

Brianne Kimmel: Hi, thanks so much for having me.

Romeen Sheth: So Brianne, really excited to have you on the show today and dive pretty deeply into your perspective on all things future of work, but before we jump in, tell us a little bit more about your background.

Brianne Kimmel: Yeah, sounds great. So I spent most of my early career at Expedia. I worked across the consumer experience and also the B2B side of the business.

This was where I got most excited about enterprise businesses and the future of work.

Expedia was one of the first technologies to really tackle a very large antiquated sector and bring them online.

So if you think about airlines, hotel chains, car rental companies, before Expedia, essentially the entire landscape was fragmented and heavily reliant on travel agents. 

Brianne Kimmel: By bringing all of these services online, it actually created a whole new level of transparency in terms of pricing, standardized star ratings and publicly available consumer reviews. 

I think what was really interesting was during my time at Expedia was the mass consolidation of these online travel agencies. 

Expedia had acquired Orbitz, Travelocity and HomeAway to bring non-traditional, Airbnb like accommodations to the platform. 

Brianne Kimmel: It was great to experience first hand the size and scale of a platform like Expedia with supply consisting of the world’s oldest hotel groups and airlines and demand

So it was really great to really understand how do you use software and how do you use a marketplace, essentially, to bring in an outdated sector or category of businesses online, and then how do you use even reviews and recommendations and really strong data science to essentially bring a whole new level of transparency to a certain category.

Following my experience at Expedia, I got recruited for a role at Zendesk. 

So I took my platform experience from Expedia and applied it to enterprise software. During my time at Zendesk, we went from one product to seven products.

Brianne Kimmel: A lot of folks know Zendesk for Zendesk customer support, which is our core product, but essentially we built a whole suite of additional services such as live chat, more robust analytics, and a number of basically new technologies that would help us not only sell better into the enterprise but ultimately compete against Salesforce.

Brianne Kimmel: It was really cool, because during this time, I started spending a lot of time with our customers, so Peloton, Allbirds. I built a program called Zendesk for Startups, which was our way to create a dedicated program of the next generation of great companies. So it was a really interesting time in Zendesk journey where essentially, as we were moving that market and tackling more large antiquated enterprise companies, we also wanted to make sure we had programs and infrastructure in place to really support the next generation of great, disruptive companies.

Romeen Sheth: Yeah, your suite of experience is really interesting to me, because I think it ties to kind of a fundamental underlining of what’s going on in the labor markets today, right? So the labor markets we’re living through right now are, I think, incredibly interesting. It’s only at certain times in history that we reach such inflection points where policymakers, business leaders, and workers, frankly, are thinking through the benefits and uncertainty at such scale.

Romeen Sheth: So it’s a huge point we can obviously talk about for a full episode, but at a macro level, what’s your view on how to think about the intersection between technology and the labor market?

Brianne Kimmel: Yeah, that’s a great question, and I’m happy to kind of dissect it in terms of how I’m thinking about how do we even just categorize work? Because I think right now, there are just so many different ways to actually think about post education. How do we classify our work? There’s a lot of conversations around things like a side hustle, or you’ll hear folks talk about underemployment.

I’ve really been thinking about four types of labor:

  1. Centralized white-collar: knowledge workers in an office
  2. Decentralized white-collar: remote & freelance knowledge workers
  3. Centralized blue-collar: manual/physical labor in factories or warehouse facilities
  4. Decentralized blue-collar: desk-less workers such as delivery, installation and maintenance professionals.

Brianne Kimmel: So what’s interesting today is that in addition to having white collar work and blue collar work, we actually are starting to see new trends in terms of centralized and decentralized.

Technology companies will talk about what does it mean to have remote teams? Remote teams are becoming more and more important. You see that white collar distributed work is actually, there’s a broader trend where people actually like working from home.

It’s great to have your own setup. They like the flexibility. We’re seeing trends, even, in terms of how does this create a more inclusive workforce, I think specifically for new parents and also for the aging population.

We’re seeing that people are willing to work longer and they’re willing to continue contributing to their places of employment longer if they’re able to choose the way that they work.

Oftentimes, the way that they work is best from home.

Romeen Sheth: I like the decentralized, centralized framing, because I think if you look at the value stack, you see kind of different dimensions of what’s going on today. You have one side of the value stack which has a ton of increased opportunity sides, right? Finding talent and high skilled workers can be challenging in today’s market. But then you have the other part of the stack, more low skilled workers in many ways are being left behind. 

You have a pretty interesting perspective actually specifically on how millennial men are less likely to work than any other gender demographic. Talk a little bit more about that.

Brianne Kimmel: There’s also a lot of research that’s been done lately on the millennial work opt- in rate, and what’s interesting is when you look at recently changes. We’ll look specifically at the US labor market. Specifically with the US labor market, we have seen a shift where millennial men, so primarily men who are 25-34, they’re actually opting in less than previous generations, and more specifically, post-global financial crisis and post the previous economic downturn.

We’ve seen a major shift where actually, there’s an element of unemployment that’s happening, or underemployment that’s happening across the board. However, we’re seeing that men in particular are actually opting out rather than accepting underemployment, which is quite interesting.

Romeen Sheth: It’s interesting too because you can cut it kind of from a demographic perspective, but you can cut it from a skills perspective. One of my favorite or most interesting stats is if you look at it from a skills perspective, there’s actually a huge technical talent shortage.

Brianne Kimmel: Yes.

Romeen Sheth: So by 2020, there’s gonna be over a million and a half software development jobs than actually applicants who can fill them. So how do you think about it kind of from a skills perspective?

Brianne Kimmel: Yeah, I think this is a really interesting point, because I think historically when we talk about software development, there’s an assumption that you need to have a computer science degree. Now that we are seeing different types of software development emerging, we’re actually seeing a whole new landscape of both software technology that will help us build faster, but also ways for people to learn how to build software faster, as well.

So I think what’s interesting is we’re actually starting to see that computer science majors are opting into much more challenging roles when it comes to the full stack of things that we need to build.

So you’ll notice, we’ll talk a lot about in Silicon Valley is the smartest and the most technically capable developers, they want to work on things like AI, ML projects.

There’s a shift towards the smartest people really want to work on these new applications and these frontier technologies where essentially you need to have a computer science degree or you need to have additional training for that.

Brianne Kimmel: What this has actually done though is it’s actually created a whole new landscape of roles and responsibilities within an organization where essentially, you don’t need a CS degree. So there’s a lot of great programs. I think in the previous tech cycle, we saw coding camps and things like Dev boot camp or like general assembly, where essentially you can learn how to build great applications and especially in sort of front end web development. You can actually do a lot of things without a CS degree, which is great.

Brianne Kimmel: So we’re kind of seeing these two paths where I think there are individuals who are technical-ish or technical enough to really be able to add value outside of having a traditional computer science degree. I think this is where we’ll continue to see programs like Lambda School, for an example, where essentially, it does make sense for us to provide new classes of work for people who would like to work for a tech companies, but they either can’t or aren’t ready to commit to a full CS degree.

Romeen Sheth: It’s interesting because I think that has some pretty deep implications for skilling capability building. I want to jump into that a little bit later in the conversation because I think there’s some interesting nuances there. I’m curious to hear your perspective on how you think about job characteristics and job skills that folks should be thinking about.

So the McKinsey Global Institute did a study pretty recently on looking at characteristics in occupations that could be automated away. It was interesting because the conclusion was less than 5% of jobs were at risk of being full automated away, but up to 40% of skills that are the underlying components of those jobs will be affected by technology.

So how do you think about kind of that conclusion or that statement both from the perspective of a startup that’s building and then from the perspective of an individual worker?

Brianne Kimmel: Yeah, so this is a topic that I think about a lot, and I think what’s great is the time that I spent at Zendesk was very much a time period where I learned a lot about various functions within an organization. I think that customer support is actually a really good analogy for the way that I think about automating work versus augmenting work.

If you look at the sort of day to day roles and responsibilities of a customer support agent, there are a lot of things that we can augment and that we can automate to make their day to day much more enjoyable.

Brianne Kimmel: So I think the question and what you sort of read in a lot of headlines is that jobs are being replaced, things are going away, and I think that oftentimes, those sort of headlines don’t really dig into how complicated and how nuanced each individual role actually is.

So I’m an investor in a company called Forethought AI which does enterprise search and they do what we call human augmentation. They’re starting with customer support.

The reason they started with customer support was this is one function within an organization where essentially, agents don’t really have the tools that they need to do their job.

What I mean by that is we have created a whole suite of different technologies for agents to receive comments from customers and to respond to them, but we haven’t gone the next layer deeper where we actually give them access to the right information internally to solve problems quickly.

Brianne Kimmel: At Zendesk, we’ve done a lot of research around this as well, as far as how long does it take to respond to a customer’s question?

Oftentimes, the reason that it takes so long is that the agents don’t have the information they need to solve the problem. So they don’t have access to internal information or maybe data is sitting in different technologies that they don’t have access to.

So I think what’s interesting is often times when we talk about replacing roles, or when we talk about workplace automation, what we really need to focus on I think in the next 5-10 years is how do we actually augment a person’s day to day and actually remove some of the daily annoyances that keep us and hold us back from doing what we’re meant to do faster.

Romeen Sheth: Yeah, I like that framing a lot, because one of the things I’ve been most interested by is this idea of digital transformation at work, and specifically two buckets of it.

One which is entirely new forms of work, and then the second which is work that can created on a scale by platform businesses. On that kind of latter point, I had JD Ross, who was one of the co-founders of Opendoor on the show, and he talked about how he’s seeing individuals actually created larger home services businesses off of the Opendoor platform.

Romeen Sheth: I think it’s a very interesting kind of nuance. I’d love to get your perspective on how do you think about, there’s obviously the gig economy, but how do you think about how the gig economy and this opportunity set particularly unfolding?

Brianne Kimmel: I absolutely love what Opendoor’s doing and I think that’s, Opendoor will be an analogy for a number of other sectors. I think the same way that the Lambda School model which basically, you can learn without any sort of fees and you don’t have to pay until you get a job.

I think these sort of models are great starting points, and I think they will carry into other sectors, which is awesome. What’s interesting about building services on top of these platforms is that it creates a whole new opportunity for people to make money.

Brianne Kimmel: So I think historically, when we think about the gig economy, I think one of the challenges with the gig economy is typically, you will not, they’re used as basically complimentary or supplementary income.

Oftentimes, Uber drivers still have a full time job or you have to essentially have multiple gig jobs to really make a true salary. Whereas I think with a lot of these platforms, I’ve spent a lot of time and done research with specifically with people who do full time HomeAway rentals or Airbnb rentals. Essentially, you could build your own services business on top of a number of these platforms.

Brianne Kimmel: I’ve been spending a lot of time lately looking at marketplaces for knowledge workers, and I have two examples. So one is a company called Wonder, which is based in New York. They do market research on demand, so essentially, if startups all the way up to Fortune 500s want to access additional individuals to help with research, so think basically early research that will then be passed to management consultants or to lawyers or accountants.

This is a job that didn’t exist before, but for the average person, especially someone who is either in college or recently graduated from college to build your own business where you’re able to do research from home is actually a really compelling alternative to driving for Uber or doing Postmates after you’ve recently received your college degree.

Romeen Sheth: Let’s dig into that a little bit more, because I think what you’re hitting on is kind of the intersection between doing new services on top of existing platforms. Then there’s another bucket which is just entirely new types of work, and you have a really interesting perspective on this with your thought process on influencers and streamers.

There’s a really good tweet that I was reading this weekend, and it pointed out that now Joe Rogan gets more views than CNN, Kylie Jenner is dominating cosmetics, and Conor McGregor can sell more pay per views than the UFC.

Romeen Sheth: I think there’s two threads there, right? One is just entirely new types of forms of work, and then the second is kind of the age of the individual and a little bit of the power of technology with distribution scale. Let’s talk about the first one first. Talk a little bit more about your perspective on not just digitally enabled work but really entirely new type of work.

Brianne Kimmel: Yeah, I mean, I think this a really interesting point where I think we’re seeing this shift where in generations prior, I think specifically post World War II, oftentimes people took the job that was open and available, and they took a job that was close to home. I actually have recently done a lot of research on post World War II, like how did we transition from a wartime culture and specifically very much a blue collar culture into these new communities of white collar workforces. Where did we actually start transitioning from kind of the industrial revolution into where we are today?

Brianne Kimmel: During this period in time, that’s when we saw the introduction of things like the Myers-Briggs and the sort of new ways of thinking about work where essentially, people want purpose. I think prior, it was how do you work hard, how do you demonstrate that you’re working hard, and how do you basically provide for your family? Where I think today it’s more about, how do we find purpose? How do we find new ways to be creative and to build? I think what’s different about our generation is that we are highly creative and we are a generation that wants to build something.

Brianne Kimmel: We see with these new platforms, Twitch is a great example. YouTube is a great example as well where we have these new platforms where essentially, you can actually create your own type of work. There’s nothing stopping you from becoming an expert in basically any field that you’d like. I think an example I have here is I recently went to TwitchCon, which was an amazing experience to spend time with a large group of people, thousands of people, actually who have either built a company on top of Twitch from a tech standpoint, or who actually stream full time.

Brianne Kimmel: What was interesting was I had a conversation with an individual who is a streaming coach. I was saying to her, I said, “What did you study? What did you dream of doing when you were growing up?” She’s like, “When I was younger, I never thought I was going to be a coach. I never thought I’d be a professional coach, and I would’ve never thought that I would be helping individuals become more animated as they’re broadcasting their ability to play video games. There’s just so many classes of work that we didn’t know it exists. I think touching on influencers and streamers, there are amazing ways to do what you love and make enough money to not only pay the bills but also become incredibly successful.

Brianne Kimmel: So I’m super passionate about these new platforms for distribution, how people are using them to create new types of work.

Romeen Sheth: That’s interesting. Let’s dig into that a little bit more, because I think one of the things that I’m seeing is as we move more and more towards this world where individuals can leverage all sorts of technical platforms, whether it’s infrastructure or distribution and have the ability to create upsized economic value and influence. It’s exciting because of the leverage, but it also requires, I think, a new set of responsibility guidelines and standards. We saw the effect of this on a really small group of influencers and how it exacerbated the impact of Fyre Festival.

Brianne Kimmel: Yeah, I agree, and I think what’s interesting and one thing that when you talk to influencers who are just getting started, it goes back to the early days of Hollywood where yes, your quality of content does matter, but also there is an element of access and of luck. I think specifically for YouTubers that are just getting started, oftentimes as these platforms start to mature, it does become increasingly hard to get discovered or to become famous.

Brianne Kimmel: So I think it’s really interesting to see over time, in the age of the individual, we actually start to revert back to very tried and true behaviors of individuals ultimately need groups. I think that’s something I saw at TwitchCon where essentially, streamers don’t operate on their own. They actually find ways to collaborate. Influencers also create this whole network of other influencers where they can promote each other’s content or work together and do a lot of collaborations with brands.

Brianne Kimmel: So I think while we’re entering this age of the individual, we’re actually starting to see these kind of next gen of social constructs being built, which is really fascinating. I think to kind of talk about Fyre Festival for a little bit, Fyre Festival was only successful because they leaned into a very human truth and something that’s very true today, where people are looking to have access, and they’re looking to actually build credibility through spending time with other influencers or experts.

Brianne Kimmel: So while over time we are kind of the age of the individual, I will say that I think with Fyre Festival for an example, these influencers that were involved in actually promoting the event, part of the hype and part of the demand was actually, wouldn’t it be great if I could get access to these influencers and I can spend time with them and I can kind of live, access that lifestyle by paying for a ticket. It turns out people are willing to pay for those tickets.

Romeen Sheth: Talk a little bit more about kind of distrust and how in kind of the age of today you have companies where reputations take a long time to build and one misstep or trust can kind of exacerbate out of control. How do you think about that from the company perspective on how to proactively manage?

Brianne Kimmel: Yeah, I mean this is something that I’ve been spending a lot of time on. I think a lot of these heritage brands that we know and love have become so large that it’s very challenging for them to be transparent. So I’ve seen this when working with Fortune 500 companies where we start to, as your company grows, and this is natural, we start to have more policies. But one of the challenges with a lot of these policies is we start to lose our transparency over time.

Brianne Kimmel: This is an area where as we see this next generation of great companies, direct to consumer brands are doing incredibly well at being transparent from day one. They’re also aligning to their, they are developing their own mission and values, which really resonates with today’s consumer, but I think one of the questions I have is long term will these direct to consumer brands ultimately consolidate, similar to the way that Expedia brands ultimately had to consolidate? And will they eventually lose their transparency over time?

Brianne Kimmel: I think it’s a little bit early for us to see that, but I’m very optimistic and excited to see these next generation of brands that are more transparent, that have better ingredients, that are really starting to prioritize the consumer. I’m just kind of skeptical and wonder at what point in time do they become large and bureaucratic as well?

Romeen Sheth: So as you’ve worked with a lot of, as you’ve observed kind of future of work from both an early stage startup and an investor perspective and you’ve kind of seen both sides of the gamut, what do you think large corporations and larger organizations get wrong? One of the things I see a lot of the time is this idea of just capturing data without having a really clear framing of the problem that you’re trying to solve. But when you think about future of work, what do you think that large companies or large organizations get wrong?

Brianne Kimmel: That’s a great question. I mean, I think as far as large companies go, I think you’ve really nailed it in terms of saying, oftentimes the problems that these large companies face is actually, it’s a problem of access and of information. So over time, as your company grows, fewer and fewer people have access to core data. Fewer and fewer people are truly connected to the core mission of the company, and I think oftentimes, this has to do with size and with scale.

Brianne Kimmel: Now, what I think is really interesting is now we’re starting to see where companies that want to go back to their early mission or that want to innovate and get access to the next generation of consumers, they are willing to acquire companies that match that profile. So I think we’ll continue to see large acquisitions, specifically in the retail/eCommerce space, specifically with consumer packaged goods where essentially it becomes harder and harder to innovate as a large multinational company. However, it is very easy for them to spend time with relevant startups and to actually acquire them and fold them into their portfolio of brands.

Romeen Sheth: Yeah, it’s interesting. I see a lot of, especially in the consumer goods space, a lot of, and R&D and innovation is just done via acquisition as opposed to any sort of internal, organic R&D. I’m curious to hear your perspective on the flip side of that same question, which is what do you think startups get wrong about large companies, right? I think there’s a lot of truth in corporates being very legacy and not adapting to technology, but I think it’s actually a lot less about sophistication with technology, which is often the conversation in startup rooms. But it’s more so about some of the things you mentioned, right? Organizational issues, cultural challenges, [inaudible 00:27:32].

Brianne Kimmel: Yeah, I mean, this is something that I talked to startup founders a lot about. I think what’s challenging is that oftentimes in the Bay area or if you’re in a very startup centric ecosystem, it’s very easy to sell to other startups. You understand their buying behavior, you understand how to partner with them or sort of what’s in it for them longterm, but one of the challenges is that selling to the enterprise is very different. It typically requires a different feature set. Oftentimes companies are looking for maybe if it’s healthcare, they’re looking for HIPAA compliance. If you are a large enterprise company, you have to start thinking about different types of contracts and different features, and there’s a lot of customizations that come when working with large enterprise companies.

Brianne Kimmel: So we see that oftentimes, startups, I feel like wait too long to talk to enterprise customers. I think that you can get a significant amount of traction by selling to other startups, and I think we see this a lot specifically with the YC ecosystems. So if you’re going through Y Combinator, you get access to not only your current batch of startups, but also any YC alumni companies. So you can see companies get to 500k, a million in MRR, and actually it’s just selling to other startups either in the Bay area or outside of the Bay area.

Brianne Kimmel: What you’re missing is actually a deep understanding of what are the nuances that comes with moving out market and just selling to larger companies, which I think this ultimately comes down to how large companies make decisions. Large companies typically make decisions based on how do you maintain current traction and kind of not rock the boat too much, and how do you think about incremental change rather than disruption. I think oftentimes that’s where startups will come in and if you’re presenting to a large Fortune 500 company, the last thing they want to hear is disruption or a complete change in structure processes, because essentially, what they’ve been doing is working well. It’s good enough and longterm, they want to figure out ways to align with partners that can de-risk what they’re trying to achieve and provide incremental change over time.

Romeen Sheth: Let’s switch gears a little bit and talk about what’s going on in the world of rescaling and capability builder. I also know Allred, the CEO of Lambda School, and Shaan Hathiramani who runs Flockjay, another interesting capability building and scaling startup out of YC right now in the current YC batch on the show. We talked about the education system at large, and I’m interested in your perspective on what you’re seeing with scaling and coaching startups. When you think from first principles, the experience can be pretty neat. Real time feedback, dynamic course experiences, flipping the classroom. How do you think about rescaling and capability building today?

Brianne Kimmel: Yeah, this is a great question. I think over, I would say even let’s zoom out over the past ten years. We’ve seen a number of great platforms that are focused on skilling and coaching, whether that be mentor mashing, like helping you find the right person to learn from, either as a peer or as someone a little bit more senior. We’ve seen education startups like Udemy and Coursera which have done a fantastic job in terms of essentially democratizing education that historically, you would have to either go get your MBA, go get your MFA. They’ve taken a lot of these really core, fundamental courses and brought them online for individuals.

Brianne Kimmel: I think in the next cycle, we’re seeing great, new companies like Lambda School, which I think what’s very interesting about Lambda School is they have infinite scale, because as they’re tackling such a large sector, which is education and more specifically an alternative to undergraduate college education, which is historically extremely expensive. Student loans are one of the largest point of stress for individuals. I think we’ll start to see new types of education and new types of even classes of work that come after individuals graduate from Lambda School.

Brianne Kimmel: Now, what I think is interesting about a lot of these re-skilling and a lot of the education and coaching startups is if you’re selling to a consumer or you’re ultimately competing for attention. I think one of the challenges that I’ve seen with specifically a lot of marketplaces that essentially offer professional coaching as a service or mentorship as a service. One of the challenges here is accountability, and it’s also competing for attention. So one of the things that I’ve seen is oftentimes with these marketplaces where one side is either an expert or a mentor or someone that is historically fairly time poor.

Brianne Kimmel: Facilitating that matching is very important, but also ensuring what’s in it for both sides? It’s very clear that there’s a whole category of young professionals who are hungry and eager to learn more, but on the supply side, it’s always a little bit more challenging to actually find the right people who a, have the time, and b, have the right incentive to actually invest in an individual for even a short, medium, or longterm period.

Romeen Sheth: Yeah, one of the things I always, and I’m curious to hear your thoughts on this. One of the things I always kind of wonder with with some of these kind of coaching on demand platforms or so, especially when they’re consumer focused, is how do they solve for the platform leakage problem, right? So if you think of, all marketplace businesses are different, but if you think of some of the kind of high profile companies that ended up not succeeding, like Homejoy out of YC, right? Raised $40 million.

Romeen Sheth: I think one of the big learnings from the nature of the transaction itself was that they were doing a great job of helping you match and find someone, but then the nature of that transaction was once you found someone to come in and service your home, you’re kind of, you trusted them and you didn’t really need to go back to the platform. So you ended up having a lot of these kind of platform leakage problems where folks would say, as a consumer, it doesn’t make sense for me to pay [inaudible 00:33:58]. Then as a vendor, it doesn’t make sense for you to take a price cut just by being on the platform. If we’re gonna develop a kind of longterm relationship, it just makes sense to take your transaction off of the platform itself.

Romeen Sheth: That’s something I think about a lot with kind of mentorship as a service, training as a service, et cetera. How do you think about that?

Brianne Kimmel: Yeah, I think that makes a lot of sense. I think in early marketplaces, we’ve seen that even with home sharing apps to an extent. We’ve seen that with the dog walking on demand services. Once you find someone that you really like and you build a longterm relationship, it is difficult to maintain a platform lock in over time. What’s interesting with a lot of these coaching applications is I think there is an opportunity to do more than just one on one matching, but also how do we think about the group facilitation of conversations.

Brianne Kimmel: I actually recently read an article that I thought was interesting that made the comparison that events and conferences are the new, that’s the number one choice for editorial. So historically, you would have magazine coverage. It was more about impressions and eyeballs and creating, brand building was actually built on a very specific aesthetic and look, whereas now that we’re in this sort of individual economy as you said. Now that we’re in this individual economy, what happens is actually people want to be directly involved in your product experience, whether that’s events or becoming an influencer in part of your platform.

Brianne Kimmel: I think there are ways to facilitate a lot of these service marketplaces by doing more of kind of a focus on community building rather than one on one matching. But I agree, I think to your point, one of the challenges with a lot of these services marketplaces is when you’re competing for attention from a consumer point of view, then oftentimes you’ll find these companies will ultimately convert to almost an enterprise sale. If it’s something that your work is paying for and it’s something that becomes a core part of your education or your career, then people are more likely to opt in and to lean in.

Brianne Kimmel: An example that I have there is there’s a company called Plato, which is also a YC company as well, and they do mentorship for engineers. What’s interesting is for Plato, they see high retention on both sides of the marketplace. So both on the supply side, these are mentors. These are mentors at top tech companies, and their goal is to essentially build a personal brand for themselves. They use it as a way to hire and recruit up and coming engineers, and then on the demand side, you have very hungry and eager young professionals who want to connect with leaders at other companies. Not necessarily even in terms of I’m ready to switch careers. I want to move to this company, but there are a lot of great things that you can learn from individuals at another company.

Brianne Kimmel: I always use personalization as an example. So if you’re working at a Bay area startup and you want to learn about personalization, then Netflix is obviously one company that you’d love to spend more time with. They’re actually located in Los Gatos and it doesn’t make sense for you to ever facilitate and in person conversation, but even getting access to someone who’s worked on personalization at the size and scale of Netflix is a really compelling offer.

Romeen Sheth: Well, let’s talk a little bit, I want to pick up on that last thread of personalization and I want to use it a segue to talk a little bit more about ML and AI and how it’ll affect the workplace. You alluded to this a little bit earlier in the conversation. One of the companies that I’m an angel in, Imbellus is doing really interesting work in the assessment space. I see a lot of interesting applications for ML and AI in helping improve the end to end talent equation. So screening at the top of the funnel by mapping the skills, matching and rerouting talent internally. Talk a little bit more about what you’re seeing in the space and how you think about it from a macro perspective.

Brianne Kimmel: Yeah, I think it’s interesting. With AI, ML, we’re seeing the impact across multiple, different sectors and functions. I think from a recruiting standpoint what’s great is we’re actually able to facilitate much stronger matches. I think what I’m starting to see as far as a macro level trend is oftentimes, the recruiting process is a pretty complex one. You can divide it into college recruiting, which historically, there has been a matching and facilitation problem where essentially you would have one person in recruiting who works at one company and they would go to a career fair which happens once or twice a year.

Brianne Kimmel: What you would find is essentially students would go to these career fairs in hopes of meeting someone. You’d wander around, and it was just sort of like antiquated version of matching, which is not great for the employer, because they can only meet a limited number of candidates. It’s not great for students, because they don’t really have the time or the ability to truly have a conversation and to demonstrate how they’re different from the hundreds of other candidates that you’d see at one of these large university or college career fairs.

Brianne Kimmel: So what’s great is we’re actually starting to see these new platforms, like I’m an investor in dev.to. Dev.to is one of the largest communities of software engineers, and the way that it’s different than, say a GitHub or from other platforms is it’s actually more about the individual. So it’s a place where you can create a profile. You talk about your skills as a developer. You also talk about what you’re looking for in terms of culture fit, and you can write your own blog posts that are related to remote work or work/life balance, or any sort of parts of your day to day that matter in both a personal and professional context.

Brianne Kimmel: What’s great about that is you can actually start to facilitate matching that extends beyond just these are the things that I’ve done. I think LinkedIn is great in terms of having a nice resume, but the challenge with resumes is it doesn’t really ensure future happiness. So with a resume, they are data points that really communicate where you’ve been, but they don’t really communicate where you’d like to go. I think that’s where recruiting and matching is really broken, because it’s actually a way to lean into any personal biases that you have. So then you start selecting candidates based on where they went to school or what their most recent job was. But it doesn’t really communicate appetite and hunger and drive and all of these things that we look for when hiring new candidates.

Romeen Sheth: Yeah, I like the framing of kind of a historical perspective versus a future oriented perspective. That’s actually one of the things that I like that Imbellus does the most is this idea of recruiting by set in order proxy or where you went to school, what your previous job was. It doesn’t really give you a great, full picture of the story, right? But if you can start to understand how people think about problem solving, critical thinking, right? Judgment, how they exercise judgment, these are the core skills that you really want to see, right? You want to see in any sort of type of worker. It gets especially interesting I think when you actually put blind screens on top, to your point a little bit around kind of confirmation bias, right? I think you actually end up getting more interesting results based on the actual kind of first order observations that second order observations might not have gotten.

Romeen Sheth: But what are the most interesting kind of specific applications of technology you’re seeing as related to the workforce and kind of workforce productivity and what you’re most excited about today?

Brianne Kimmel: So I’ve been spending a lot of time in basically three areas. We talked a lot about new platforms for distribution and new classes of work such as streamers, influencers, and some of the new workplace applications that will tie into the gig economy. I’m also looking at distributed teams and not from the lens of do companies allow you to work from home one or two days a week, but what does it actually mean for a company to be fully distributed from day one?

Brianne Kimmel: I think we have a few examples today that have proven out this model. So we have InVision, we have GitHub, which is primarily distributed as well, and we have a whole kind of plethora of new startups that are essentially starting with distributed teams from day one, because it’s a great way to reduce overall cost. So you can remove real estate from the equation. You can hire great talent from anywhere. You are not constrained to only one or two markets where you have your HQ and maybe a satellite sales and marketing office.

Brianne Kimmel: So we’re really starting to see what are the deep mechanics to build a decentralized team from day one. That’s more on the white collar and on, in terms of knowledge work. I think on the blue collar side, what’s really interesting is we’re starting to see new applications that truly understand both centralized blue collar work, which is more factories and more kind of large companies. We also see new applications for decentralized blue collar work, which the example that I use there is a company called Earnin. Earnin is backed by Andreessen Horowitz, and they allow people to get paid in between paychecks.

Brianne Kimmel: What’s great about the model that they’ve built is they’re actually using a number of models that they’ve built to understand how many hours are you working on a weekly, monthly basis? How much money can we give you in between paychecks to actually unlock new opportunities for you as an individual? One way that they do this, which is super cool, is the actually can forecast on when are you actually at work? So they can use data from your phone, which tells you on average, you’re spending 5-10 hours, let’s say if you work an hourly wage job. You’re spending 5-10 hours at this certain company. Maybe you work at a restaurant, something like that.

Brianne Kimmel: But then you also have a side hustle where you also spend another 5-10 hours. So it can actually start to forecast how much money can we give you in between paychecks because we know the number of hours that you’re working. We see that you are fairly consistent in the hours that you work. However, like most people, unforeseen bills come up. Maybe it’s as medical expense. Maybe it’s a family holiday. Whatever might come up, there are just certain times where we need a little bit of extra cash, and they’re able to facilitate that using what they understand about the hours that you’re working and more importantly, the data that goes into this model that they’ve built.

Romeen Sheth: This has been a super interesting conversation. Granted, as we round out, I’d love to ask you that kind of Peter Thiel question as applied to the future of work which is what do you believe to be true about this idea of future of work that most people wouldn’t agree with you on?

Brianne Kimmel: I think to date what I’ve been thinking a lot about is how do we augment the way that people work today? I think that makes AI, ML, fairly approachable. I think in the short term, it’s really great for us to align on the fact that there are a number of things that we do in our day to day that are highly inefficient. But I think longterm, I’m actually very optimistic about the automation of work. What I’ve noticed in terms of understanding a lot of deep nuances in terms of blue collar work is there are just categories of jobs that shouldn’t exist.

Brianne Kimmel: I don’t believe that people should be truck drivers. When you look at the overall side effects and from a safety standpoint as far as number of car accidents, but also when you look at just the overall health of truck drivers, it’s a really, really sad job to have. I think that there’s a number of ones like this where when we start to look at different categories of work.

Historically, we haven’t had the technology to automate jobs that are, quite frankly, unsafe for people. So I think over time, I’m really optimistic in terms of automating things that are incredible unsafe. We can look at a list of these are the top 20, 40 jobs that have the most amount of workplace injuries and fatalities. We can just figure out ways to solve those problems. I think that is the starting point.

Brianne Kimmel: If I were gonna start a company today, I would start with that list. I would look at, I think another space that’s really fascinating is if you look at, when we talked about millennial males opting out of work, a huge percentage is actually driven by the opioid epidemic, which is a manmade epidemic. It’s a problem that’s impacting a large percentage of specifically American males. So how do we actually find alternatives to prescription medication? How do we disrupt certain, I would call them cartels, essentially these large, antiquated spaces where essentially, we are causing harm to the average American person.

Brianne Kimmel: So I think for me, short term, very much aligned in terms of let’s augment what people are doing today, but I think longterm, we need to automate work. We need to automate certain jobs that are incredibly unsafe.

Romeen Sheth: Well, Brianne, this has been a really interesting conversation, and I’m glad you were able to make the time. Thanks again for joining us. We really enjoyed having you on today.

Brianne Kimmel: Yes, thanks so much.

What startup founders don’t understand about developers and community building

Building a SaaS platform that 3rd party developers will love is no easy feat for startups.

Community building requires dedicated time and resources. Traditional marketing and sales tactics don’t work for developers. Customer retention can be challenging if your product is easy to rip and replace or devs can easily build it themselves.

As part of SaaS School, I interviewed Dev.to founder Ben Halpern on the evolving landscape of developer communities and best practices for software companies that sell direct to developers.

In this talk, we’ll cover:

  • How to engage with existing developer communities
  • Motivations and incentives that get developers excited
  • What it takes to build a SaaS platform that 3rd party developers will love
  • Best practices for community building and measuring success

Skim the full conversation below and don’t forget to sign up to get future essays delivered to your inbox.

Brianne Kimmel: 00:00

I’m excited to be joined on stage with Ben Halpern, CEO of Dev.to, for an open discussion on how to sell direct to developers and best practices for building a developer community.

So, Ben, we have a lot of startup CEOs in the room and for most startups hiring developers is hard.

What are your thoughts on how an entrepreneur should build relationships with developers and when does it make sense to start engaging with dev communities?

Ben Halpern: 00:24

Yeah. So, in terms of developing a community, I think it’s important to pay attention to the longterm fundamentals of marketing yourself on the internet, finding your voice, developing a brand that the people can relate to and understand that’s maybe different from some of your other customers. 

If you sell directly to developers, you’re probably going to have a different brand than if you need to hire developers, but also sell to someone else.

Ben Halpern: 01:00

And then I think it’s a lot about paying attention to your wins, and running with it, but then also just doing a lot of listening.

So, the question is I think a little different if you’re looking to hire, and if you’re looking to sort of develop a community.

But one of the fundamentals of any of these things is to throw away some of your preconceptions about where the best developers are.

Be pretty flexible about the interests, and needs of developers because if you have some flexibility you’re going to find some really great talent. And then ultimately, be the kind of company that developers want to work for, and they’re going to tell their friends.

Brianne Kimmel: 01:46

What’s interesting, so we’ve talked about this, or you’ve said it, as well, where oftentimes the projects and the things that get developers excited is sometimes very different from the things that maybe more CEOs or more revenue-minded founders get excited about.

Can you kind of talk about what are some things that get developers excited, and how is that potentially different from that of a startup’s business agenda?

Ben Halpern: 02:13

Developers are often excited by some things that seem less exciting.

If an interesting test automation tool hits the scene, developers get very excited, but test automation is a very boring thing. 

Just automating your code before it goes up so you have better visibility into whether it’s going to break.

Because developers, the more experience they have, the more pain they’ve lived through.

And the pain in software development is sort of the most memorable part.

People I don’t think act always on their favorite memories.

They sort of want to lessen the pain. So, vitamins don’t always work for software developers. Medicine and painkillers are very appealing.

Ben Halpern: 03:06

Software developers, in some ways they’re really excited about AI, ML, a lot of the trendiest sort of cutting edge stuff.

Everyone’s a little excited about that on some scale.

Some are really excited, but everyone’s pretty excited when a really polished tool hits the market that they feel actually fits their existing workflow.

They can see how they can kind of incorporate it without sort of changing everything else, without suffering a lot of pain through the process. So, when GitHub launched Actions, it really got people really excited even though it didn’t even hit the market yet at first. It was part of people’s kind of flow. It really helped their process.

Ben Halpern: 03:56

Even stuff like linting, it’s the process in software development of just sort of tabs and spaces, and linting tools get people excited. It’s funny. And it’s less different year to year than I think sometimes people realize in the startup community.

So, realizing that the most exciting things in the startup community are not necessarily the things that get developers as excited, and developers can get excited by some very boring things for other kind of people in tech.

Brianne Kimmel: 04:28

So, let’s say that one of the developer tools in the audience has built one of these painkillers for developers.

How would you go about getting taking this product to market?

How do you actually get it in front of the right developers?

Ben Halpern: 04:47

Yeah, so I think this is definitely one of those areas where things that don’t scale can really help.

Getting a few fans, users really on board really helps these things spread.

People love to give talks about things that they … that’s scored them some wins in their process, so you reach a few people who really love the tool, and can possibly give back to the tool in some way.

Leveraging open-source in that way is always helpful.

You score some wins with some of the right people, and they’re going to tell their friends.

People are going to write about it. It’s going to spread pretty naturally.

Trying to invest too much in paid acquisition, just like a lot of other startup ideas, the developer ecosystem can be chaotic.

It can be hard to kind of become sticky, and I think you do that by reaching a dedicated fan base at first, and hoping they tell their friends. And they will if it’s solving a real problem.

Brianne Kimmel: 05:57

Controversial question, but have you ever seen this go wrong?

So, you’re talking about building a community, and doing things that don’t scale which feels like a very organic way of growing, and kind of moving into more of a dev friendly company.

Have you ever seen examples, or have there been some lessons learned where either entrepreneurs or someone has tried to push into the developer community, and it hasn’t turned out well?

I’m trying to understand what is authentic versus inauthentic, and how do we balance both? Like move fast, but still maintain authenticity.

Ben Halpern: 06:30

Yeah. Authenticity is definitely one of the most important terms here.

Developers can smell bullshit, incredibly sensitive nose for that sort of thing. And it’s sometimes oversensitive.

Developers can become sort of jaded and cynical, and you try to reach them with the wrong messaging, it’s going to injure your brand.

You’re going to sort of live through some pain. Actually, I think as much as MongoDB has truly become a total success, and they’re a public company, and they’re skyrocketing in the public markets, and they’re incredibly successful, I think they suffered through some pain of being a database company that occasionally lost the trust of the community because data and trust go hand in hand.

And they worked through it. They had great relations. They stuck to the fundamentals.

They became the winner in a space that seemed like it was going to be the next big thing, and it turned out it was just Mongo plus … each of the major cloud providers has a solution, as well, in the no sequel community.

Ben Halpern: 07:57

There have been some other attempts which have sort of failed by failing to kind of work through the actually pain developers were having, and bring the product people cared about even if it was useful.

In contrast to Mongo, RethinkDB, another database, very similar model. It was an open-source database.

It lives on as a project with some popularity, but still a lot of pain, but the company folded.

They just didn’t really solidify the trust, didn’t get the messaging about why this was a really differentiated project.

I had some experience working with it. I think I remember it being a little bit more painful than it needed to be, and they just didn’t get it right even though the technology was. 

Mongo failed in a lot of the same ways early on, and I think they did a good job of maintaining trust in their brand, and understanding the more boring value propositions that sometimes people cared about.

Brianne Kimmel: 09:17

Do you feel like with Mongo, with GitHub, with Twilio, with some of the more mature companies, do you notice a different type of developer that wants to join and work at these companies?

Do you see different ways of some developers or more early stage startup individuals others want to join because there’s different problems to solve once the company starts to mature?

How do you think about the various different types of developers?

Ben Halpern: 09:42

Yeah. That’s definitely a spectrum that exists. So, I think folks in the Silicon Valley area also tend to over index on the people that fit into their physical universe, which represents a pretty small percentage of overall developers.

Twilio has always had success because they solved a lot of really fundamental problems, but I think for awhile they had a harder time reaching the more excited developer community in some way, especially after I think SMS became a little less exciting for people.

Ben Halpern: 10:30

So, at the height of maybe the chat bot excitement, maybe Twilio had a certain bit of momentum which faded a bit, but they stayed strong because they have good fundamentals. 

They’ve got sort of different markets, but it is like the people who care about the most interesting, innovative things that a company like that will do are definitely a different crowd than the people who think that the communication pipes of the software industry are the most exciting part.

And very different people, you don’t necessarily have to try too hard to overemphasize either one because if you’re clear about your value proposition, and you have a good looking brand, people are going to sort of understand.

Ben Halpern: 11:35

So, I don’t know if you want to over-communicate where you stand on that spectrum because you probably need to hire people on either one, but you should have an idea of what value you bring to each kind of person.

Brianne Kimmel: 11:47

Yeah, that’s a really interesting point.

What I love about Dev.to is the ability to communicate the things that they want to work on, or sort of the things that you’re currently thinking about versus maybe the things on your resume. 

This is really important as people are switching companies, changing careers and constantly evolving in their interest areas. 

Are you seeing any trends with decentralized companies where the need for community is sort of increasing over time? Is there a greater need for developers to connect with other developers? 

Ben Halpern: 12:26

The decentralized nature of software development, and the idea of asynchronous communication as being so important has been sort of with us forever.

The start of the world wide web had all these fascinating asynchronous conversations between Marc Andreessen who co-founded Netscape and Tim Berners-Lee who invented the World Wide Web, who represent to incredibly different ends of the spectrum in terms of software development personalities, but two super brilliant people who understood the power of the web early on.

And that same sort of fundamentals of communication, and how community happens hasn’t ever gone away, and is probably having a resurgence because of remote work, which it’s possible is just the default in our industry going forward. I would say if I were to guess that I think that would be the case, and I think there’s going to be some purpose for campuses as part of a strategy.

Distributed work, and more fundamentally, asynchronous communication as the thing that enables it is critical, and you see a lot of companies building really good tools that help with this.

Ben Halpern: 13:47

Slack is useful for both synchronous and asynchronous. There’s a paper trail. Notion is a really great product that I think solves a lot of problems.

And then GitHub for asynchronous communication was really the big one for software developers.

The part where you use Git, and merge the code, and stuff is what GitHub’s built on, but that didn’t really mean GitHub was going to be successful. But they really understood communication, and continue to kind of innovate, and build on that.

Brianne Kimmel: 14:22

Specifically with some of the earlier stage companies here today, often times you’ll have maybe a few core team members, or early founders are based in Silicon Valley, but behind the scenes, you have an army of developers either in your home country if you grew up overseas, or you start to build more remote engineering offices sooner rather than later just due to costs in the Bay Area.

What are your thoughts on some ways to not only find the right devs, but also some ways to think about employee retention, and what sort of motivates them over time?

Ben Halpern: 14:58

With remote employees, retention and motivation is probably the hardest part.

Communication has gotten easier over time, but it’s really hard to tell if someone really hates their job if you don’t see them.

We have a portion of our team remote. We have an office in Brooklyn. I don’t even go in most days.

Early on we did more in person because we just had to kind of work through less organized stuff, but eventually, saving the time on commute became so much better.

Ben Halpern: 15:53

So, we have one person that works for us full-time as a contractor now in Russia.

And I communicated with her when we were hiring her. One of my co-founders I think talked to her via video call, but I don’t even know what she looks like.

But we have tremendous communication. We have great vibes, and then we’ve also had some issues with just … we had a hard time as the home base kind of communicating with folks.

I’ve seen it really go horribly wrong in some cases where you just have no idea what’s going on over there.

You’re just praying that this distributed team is doing the things you want them to be doing, and you just go downhill, and you fail. So, you need to be sort of agile.

You need to kind of develop an understanding of what’s going on, and really over-communicate everything.

Brianne Kimmel: 17:02

Got it. So, process, communication, you mentioned Slack is great for that.

Notion can be another, as well. What about in terms of career development and mentorship?

Because I’ve seen a couple of platforms played out as one where you’re able to get mentored by more senior managers at other companies.

Do you feel like there’s a need for ongoing education? Or how do you think about retention when it comes to not only hiring, but then training and continuous education with developers?

Ben Halpern: 17:32

I think with continuous education, there’s a sense that … I would think that the hardest part is that there’s probably not going to be any singular tools which are overly effective because of the hyper specific nature of a lot of software development problems.

So, you need to sort of learn by immersion, and that’s what’s great about when you’re hired into a company with an office. You can kind of be a fly on the wall in certain discussions, and stuff.

And that’s definitely not the case as much in distributed environments. I think the most important thing for the individual developer, and for a team looking to be successful when you’re looking to have your distributed team learn, and get better, I think it’s to look for self-starters, and for developers to become self-starters.

Because there is a huge amount of resources out there, and there’s a huge amount of helpfulness from the senior development community, and they’re always being proactive. The good ones are really getting ahead of things, but people get lost when they’re waiting around for someone to kind of solve their problem.

Ben Halpern: 18:51

Me, working at our HQ, or in my home, I have a hard time. I won’t know if you’re just struggling through one little thing, and I could just quickly help you out.

You need to be able to communicate back up, like what’s going on with your day.

We don’t want to know every detail you go through. We want you to be able to kind of take a walk with your dog, and come back to your computer.

We don’t want to know where you are, but we really need to know what you’re going through. It’s those little moments that sort of push you in the right direction, and you need to kind of communicate that back up. As the founders, as the people vested in the success of our hires, and our contractors, we need to make it easy for them to do that. So, that’s kind of the dynamic.

Ben Halpern: 19:44

And then the education happens on its own throughout the community. So much of what we do is education. There’s education everywhere. GitHub, Stack Overflow, organizations that specialize in the education process explicitly, and it happens very organically as long as there’s communication, good, solid, two way communication, and ground up communication from the newer developers and stuff.

Brianne Kimmel: 20:08 

I’ve seen this in companies that have a culture focused on transparency. I think if you have a very open culture where it feels like no ask is too small, and you can kind of create these systems where it’s easy to communicate, it’s easy to ask for help without feeling embarrassed, or like you’re failing. It’s great to hear.

I think that you guys have done that really well. I think another thing that Dev has done really well is I think that by building a community you have been able to partner with other great tech companies.

Can you talk about how you work with companies like Netlify, Repl.it or Digital Ocean? 

How do you view your job as a founder in terms of helping other companies, or in terms of building long term relationships?

Because I think for this audience, what’s interesting is we’re all around the same size and same stage, and I think there’s an opportunity to either do things as tactical as coming together for a hackathon, or just really starting to build the community from day one.

Do you have any thoughts on how you started that from the beginning?

Ben Halpern: 21:15 

In terms of successes and failures in partnerships, and getting along with organizations, I think consistent learnings for us have been to walk away from discussions with some next steps.

Even if they’re the simplest things, and even if it’s … be good at having the right ask. You’ll leave a conversation with someone, and you’ll be like, cool.

You should start using our platform creatively. It’s hard to stoke creativity in people.

If you’re creative with our partnership, it’ll go great because you have all these tools we have for you.

But that sometimes doesn’t go far enough because people get busy with other things, things come up. So, some very simple takeaways is to kind of get the ball rolling, or help momentum happen, and stuff like that.

Ben Halpern: 22:17

I was just talking with an important contact this morning at a big tech company who would love to be kind of using our platform to help communicate with their developers, and things like that.

At the end of the conversation, he said, “How can I kind of help you today as much as possible?” And that’s kind of been a hard question for us to answer. Just like, I don’t know. Just be awesome. Be a good community member, and stuff.

But knowing that the vaguer it is, the less likely anything will happen, I gave some really boring things that they could do this afternoon that would just be helpful for us no matter what happens with our relationship.

One of those things was I asked them to put the Dev logo on their personal homepage just alongside Twitter just as a totally arbitrary, specific ask. But it sort of cemented like, let’s do one thing together, and then the next step, and the next step.

Ben Halpern: 23:18

Even though you could go in any number of direction, having a simple step zero with any relationship is incredibly important. It’s similar to kind of on-boarding a new user.

They’re not going to start becoming a power user on day one, but you want to give them a few simple steps to get started with your project, and then ultimately things happen through various a-ha moments along the way. Relationships build.

People kind of learn the tools, and understand the nuances, and that’s never going to happen if you’re just constantly expecting them to figure it out on their own, or leaving things vague because then you’re just going to kind of forget about it, and go home.

Brianne Kimmel: 23:59

I think that’s a really interesting point. I feel like with a lot of startups, we typically wait for awhile before we start to approach the big tech companies, or start to think about partnerships, or working directly with them.

I think oftentimes it’s like prioritization. How important is it to start building those relationships? And also how actionable is it going to be?

Because I think a lot of times when talking to some of the large tech companies you can kind of get into … you kind of go down the rabbit hole of meeting after meeting after meeting.

When would you recommend starting to build these relationships?

And what have been some ways where you able to kind of solicit those next steps, and make sure that there was followup?

Ben Halpern: 24:43 

This sparks some good thoughts about our absolute origin stories when it was just me. Not even our, just me sitting around. But you’re always going through different origin stories, so I think things like this kind of help it, a kind of new beginning.

But when I had the Twitter account, I had a bit of a following. I had this new kind of blog I was writing on, and stuff. I had the idea that if I interviewed some bigger names, that they would share the interview after that, and that would be a great way to kind of build things.

Interviewing someone via blog was good, and I understand the issue. I’m a good communicator. I felt like if I have some good questions, it would be good content.

Ben Halpern: 25:32

So, I just emailed some huge names, and they responded. Literally, at that point I got 100% yeses. I emailed the right people. I didn’t even propose an interview. I just proposed me sending them a couple questions via email for them to answer, and then just let’s kind of treat this as if it were an interview, but I’m going to make it as simple as humanely possible for you. Just making the yes as easy as possible.

Before there was any traction, I got David Heinemeier Hansson, the founder of Basecamp, and the creator of Rails to do an interview. He was excited because they were about to launch Rails 5, and he wanted to get some of his thoughts out. And that was like an easy yes.

Ben Halpern: 26:28

I’m shy, introverted. I have to kind of work up the courage to do stuff like that, but it works if you understand that the person on the other end is going to say yes. A little self reflection in that way really goes a long way.

When you get an email, and it’s actionable, the ask is easy for you to do with your own knowledge, software developers I know just love blabbing about their things, like what we’re doing right now.

And making the ask easy, and simple, and within the person’s wheelhouse is great. I’m also kind of in a conversation with someone who proposed a fun little collaboration, and I’m actually personally struggling through it because I want to do it, but it’s requiring us both to be creative, and figure things out, and I would’ve kind of preferred if there was a very specific ask

Brianne Kimmel: 27:53 

With developers, it feels like there are blurred lines between personal and professional. 

You can build a personal following for your open-source projects that you’re building for your company.

Do you kind of lean into the personal plus professional, where you’re building relationships with the individual who may or may not stay at that current company?

They may go to a different company. How do you sort of view relationship building when it comes to the personal, and the professional side of things?

Ben Halpern: 28:41

Yeah. I definitely think that’s pretty key to everything. I have a friend at Microsoft at Azure, and when I met her she was at Google. Now we’re the total competitor in that specific space. And that was cool, and we kind of have to understand there’s a lot of fluidity there.

Most business relationships are more personal than professional really, honestly. People want to do business with people they can be friends with, and stuff. I think it’s important to understand appropriate boundaries for even just any personal relationship.

So, you have a relationship that’s different from being best friends because I don’t think it’s necessarily healthy if people just do work with their friends. But you know, seek out the personal relationships with a variety of people that they can have in their lives, and ask personal questions. Get coffee, and don’t talk only about the work or the opportunity. And that’s led to a lot of our success, my success, just being friendly, offering to help on things that don’t have an obvious payoff.

Brianne Kimmel: 30:13

Yeah, that’s a great point. I think that speaks a lot to also the format of this event, and why we’re hosting it at GitHub. So, GitHub, that’s part of their core ethos, and they still deliver on that to date. Where I think like you said before, when you invest in non-scalable things, and when you proactively bring people together, there’s always a nice support group, and people who are willing to be helpful. We’re super grateful to have this space, and love the work that GitHub is doing to actually just facilitate these conversations, and bring people together. So, that’s great. Ben, thank you. 

Hosted by Brianne Kimmel and Ben Halpern.

Ben Halpern is the founder of Dev.to, one of the fastest growing communities for developers with 1.8 million unique visitors per month. Ben has written over 500 blog posts for developers and his Twitter handle @thepracticaldev is one of the most popular sources for developer news and education.

Follow Ben on Twitter: @benhalpern

Brianne Kimmel is an angel investor and startup advisor in Silicon Valley. Brianne previously worked on the go-to-market team at Zendesk focused on self-serve revenue growth, technology integrations and built Zendesk for Startups.

Follow Brianne on Twitter: @briannekimmel

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