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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,

Brianne 

How creatives win friends, influence people and break the internet

The rise of design collectives, technical designers, no code + production-ready tools and viral side projects (e.g. Amazon Dating 💕)

A few Saturdays ago, I was running late for drinks at the Ace Hotel in Downtown Los Angeles. My friend Ani was already waiting by the pool. I had dozens of messages on Slack, WhatsApp and Twitter to coordinate who was arriving when, and most importantly, what everyone wanted to drink.

On my way up the elevator, I had the strangest thought: “I have NO idea what my friends look like…”

… 

After months of catching up, hours on the phone, and really meaningful advice that inspired new companies, cool collaborations and my own new fund Worklife

Here’s the catch, we’d never met in person.

This whole collective of creatives was connected through an invite-only chat room started by a mysteriously cool guy in Scotland named Marty Bell, the Founder of the famous Poolside.fm, sunglasses company Tens, and plenty of other projects that have broken the internet.

As the night went on, I was reminded of how this interaction represents the shifting gravity of technology. Companies are increasingly distributed, people are choosing smaller, selective social networks for our personal and professional lives, and tech is moving further and further away from Silicon Valley.  

In many ways, this experience was similar to the early days of Silicon Valley where curious minds assembled in a garage for meetings of the Homebrew Computer Club in Menlo Park: no membership requirements, no minimum dues, no elections of officers.

Steven Levy’s Hackers: Heroes of the Computer Revolution describes their earliest meetings: 

“It was a club of young people—every one of them could have been an entrepreneur—the sort of people that liked to put together gadgets at home and make them work.” – Steve Wozniak*

[Photo of the Homebrew Computer Club]

In my case, what started with a late arrival, long lines at the bar and random banter with internet friends by the pool evolved into an early preview of Ani’s new Amazon Dating site, Marty’s new creative campaign for Tens, and our unannounced collaboration coming soon. (Invites for newsletter subscribers coming soon 💌) 

This is how I describe the future of work: it’s creative, collaborative and more flexible than ever.   

Hacker culture in its purest form still exists today with makers like Simone Giertz emerging as the new face of hardware. Local hackathons from London to Lagos assemble based on programming languages like Javascript and React. 

Conversations and collaboration are less exclusive and more distributed with online communities like Hacker News, Dev.to, and Stack Overflow. The open source community continues to grow exponentially with 10M+ new contributors over the last year and 44M+ new repositories on GitHub.  

In addition to the traditional technical hacker culture, I’m excited to see a new class of hackers that use both art and science to create iconic experiences inside tech companies and online: designers.

From founding startups to experimenting with an emerging set of design tools to developing cult-followings with side projects, designers are using their skills and growing influence to transform the tech industry one pixel at time.

Let’s discuss:

  1. The rise of design driven companies: great tech & company culture = iconic companies
  2. The new design stack: editing apps for consumers & professional grade tools 🚀
  3. The design projects that win friends, influence people and break the internet 

The rise of design driven companies

Iconic companies are a combination of great technology and internal culture. 

The story of the “founding hackers” is familiar. A handful of engineers working out of a garage eventually strike genius, and go on to launch the next big thing. These companies are decidedly engineering-led, with a focus on technical excellence. Think Larry Page and Sergey Brin with Google. 

[Photo of Sergey Brin and Larry Page in Susan Wojcicki’s garage]

In Sachin Rekhi’s “Finding Product Culture Fit” he discusses engineering-driven companies like Google and Microsoft:

Engineering-driven product cultures often start with a unique technical insight that becomes the basis for their products. Larry Page and Sergey Brin’s Page Rank algorithm, for example, was the unique insight that enabled them to build the world’s most successful search engine.

On the other hand, design-driven like Apple and Airbnb are decidedly different:

Design-driven product cultures obsess over every detail of the user experience.

In the case of Airbnb, Everlane, Webflow, Zendesk and other design-driven companies, design thinking and an emphasis on building a strong internal culture are influenced by the background of the founders and the structure of the executive team. 

On a recent private tour of Airbnb, Brian Chesky shared some early lessons with Worklife portfolio companies including the importance of having a design leader report to the CEO. 

This is especially important as a company starts to scale and the role of the CEO becomes increasingly tied to board meetings, reporting financials and ultimately public earnings call, he said. 

The creative voice that serves as a champion for the customer will continue to push the product and user experience and, increasingly, the employee experience, into new and innovative directions. 

Design is a core competency, not an afterthought

Founding members of Airbnb, Brian Chesky and Joe Gebbia, attended the Rhode Island School of Design and infused design-thinking into every part of the company. The company is now regarded as one of the top design-driven companies, making way for more designer founders. 

Yet, their backgrounds in design raised initial skepticism:

When we came to the Valley, no one even wanted to invest in Airbnb. One of the reasons was they thought the idea was crazy…But the other reason is that they didn’t think a designer could build and run a company.” – Brian Chesky*

This attitude has shifted, with companies like Dropbox as part of a pack of design driven companies. It turns out these companies also make business sense; McKinsey linked design-driven companies with superior business performance, specifically 32% higher revenue growth and greater returns to shareholders.  

Just as “the first engineer” was a key distinction, we’re seeing the rise of “the first designer”. First Round’s Designer Track, underscores the increasing importance of a startup’s first design hire with instruction from folks like Jessica Ko, the First Designer at Opendoor, and Davey Nguyen, the First Designer at Gusto. 

Designers aren’t simply contributing to small product features at companies as employee number 100 or 1000. They’re founding their own companies and joining startups in their earliest days. In doing so, they’re pulling influence from engineers in steering product and diverting clout from marketers in defining brand. 

As people try new tools, we’ll increasingly hear “who designed this?” rather than “who built this?” With hybrid roles like UI Engineering or “designers who can code” taking a foothold in tech companies, the answer to both questions will often be the same.

As the influence and importance of design continues to grow, dollar signs will follow. Just as the best hackers command high salaries and set off bidding wars, we’ll see design wages rise, inching closer to parity with software developers, and cults of personality build around an increasing number of talented designers.

The new design stack: editing apps for consumers & professional grade tools 🚀

Homebrew hackers like Steve Dompier tinkered with the Altair to make it play “Fool on the Hill” by The Beatles. Modern day hackers like Jane Manchun Wong reverse engineer apps to find hidden features and security vulnerabilities.

[Jane Manchun Wong discussing unreleased Instagram feature]

Designers are doing their own tinkering, using a range of emerging tools in the process. 

With the rise of no-code tools, designers have been empowered to do their own hacking, creating functioning prototypes and live sites without writing a single line of code. Designers who’ve caught the experimentation bug are putting their skills to work creating Webflow cloneable templates of popular web properties like Airbnb listings or Facebook

Engineers continue to be cut out of design workflows with tools like Rive that let designers and illustrators create sophisticated interactions and animations without writing code. 

That means working on as many iterations as needed to get it just right on a new game or app. Better yet, it’s all done on a browser. The speed, performance and the convenience of browser-based tools are driving massive productivity gains in the design world.

Similarly, Thinko’s Animation Studio is building Mr. Puppet, a hardware tool that uses puppetry to give artists greater creativity and control by letting them animate their creations instantly. 

Of course, design hacking isn’t only for experts – beginners and amateurs alike can play around with presets like Figma Valentine’s Templates as a creative outlet and an exercise in creativity within constraint. 

[Alex Muench’s popular Figma Valentine tweet]

As new dev tools and languages are created, the number of software enthusiasts grow and we see more hackers. With the rise of every day design for assets like flyers and Instagram posts, casual dabblers who start with consumer tools like Canva and Chroma Stories will eventually graduate to more complex hacking.

With the design gold rush, we’ll see a new class of designer hackers who solve interesting problems with design-thinking, define new styles for product design that shape the next generation of apps, and bring a playful hacker spirit to everything from prototyping to wireframing.

The side projects that win friends, influence people and break the internet 

Hacking together side projects is an outlet for curiosity and creativity, but it’s also a way to get noticed by people you admire and attract new opportunities. This was true of why members joined the Homebrew Computer Club:

“This was my way of socializing and getting recognized,” Woz wrote. 

“I had to build something to show other people.”

In the new American Dream, I shared how creative expression, online influence and extreme optionality is changing how Americans define success. Extreme optionality is leading to greater societal expectation for creative outlets.

Side projects are an opportunity to showcase inventiveness because they avoid the trap of creativity under the gun. While the trope of coming up with the perfect solution in the 11th hour is ever present, people tend to think less creatively when they’re under pressure. In fact, it generally leads to feelings of being “overworked, fragmented, and burned out”.

Instead, individuals perform their most creative work when they have less time pressure and feel like they have the time and space to explore ideas. For many of us, this is during evenings or weekends.

A side project shared across Twitter, Product Hunt, and Hacker News can net a brand new following, a business with revenue and profits, or job offers at a FAANG or high-growth startup. Hackers have always embraced the power of the side project. 

Inspired by a Paul Graham tweet, 16 year-old Samarth Jajoo built an app that lets you keep a private journal over email.

[Embed: Initial Paul Graham Tweet]

[Samarth Jajoo’s side project]

Designers and creatives embrace side project culture too.

Amazon Dating, created by Ani Acopian and Suzy Shinn is a satirical site remixing Amazon with the concept of finding a date – complete with a rating system, details on love languages, and Amazon prime delivery. The side project garnered press from publications like Dazed, Fast Company, New York Post, and Refinery29. 

[Screen capture of https://amazondating.co/

Pablo Stanley, a designer at InVision, controversially launched Open Doodles as an Open Design side project to help anyone to “copy, edit, remix, share, or redraw” illustrations without restriction. In hacker spirit, the project encourages collaboration.

[https://www.opendoodles.com/

Designer led side projects take countless forms ranging from memes to parody accounts that manage to go viral and blow up the internet for the day or week. Rather than kudos for technical complexity, they’re often complimented for creativity, irreverence, and style. 

Even venture capitals at top-tier firms are using creative hacks to win friends and influence people (founders) with their own personal flare. 

Side projects are better together. Having a group of peers to bounce ideas off of can help with everything from accountability to finding collaborative partners. Designers and creatives are creating their own Homebrew-eque collectives to share what they’re working on. Exclusive online memberships like Jacuzzi Club include creatives from companies like Airbnb, TikTok, and Poolside FM with discussions about creative projects or job opportunities. 

Similarly, teamLab, a collective of artists, programmers, animators, mathematicians, and architects bringing tech-art experiences to cities around the world is reimagining the museum experience with video game elements for Gen Z and Instagram-worthy moments for Millennials. 

In 12 months, teamLab’s Tokyo Museum has become the world’s most popular single-artist destination, surpassing the Van Gogh Museum. 

This is just the beginning of design hacking in the public sphere. We’ll see more public art space and new uses for retail, such as Sandbox VR, where interactive experiences will replace physical stores that have moved online or been replaced by modern brands.


The Homebrew Computer Club’s collective of hackers was described as “a mélange of professionals too passionate to leave computing at their jobs” and “amateurs transfixed by the possibilities of technology”. 

We’re seeing the same spirit in today’s new cohort of designer’s who are unsatisfied with simply shaping products at their day jobs. Instead they’re branching out and starting companies or bringing their influence to early stage startups, tinkering with design tools in their off-time, and envisioning and executing on design side-projects that make the internet a better and brighter place.

If you’re a designer who is thinking about your next move or want to show off a side project, say hi on Twitter: @briannekimmel

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: 

Share this tweet

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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Transparency

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

How Superhuman uses video game design to make work feel more like a game

The 4 components of a game-like experience featuring Superhuman CEO Rahul Vohra

I recently sat down with Rahul Vohra, the founder and CEO of email client Superhuman, to discuss his unique approach to building products that turned email, one of the most routine and mundane daily tasks, into a game-like experience that’s fast, enjoyable, and worth sharing with friends.

With a computer science degree from Cambridge and a background as a video game designer, Vohra entered the tech scene in the early 2000s. During that time, he co-founded Rapportive, an email company that LinkedIn eventually acquired. At LinkedIn he led email integrations and witnessed rapid scaling at the company as it grew from 1,500 employees to more than 10,000. 

It was during this time that the idea for Superhuman was first formed. 

“When Gmail first came out in 2004, it was fast and clean and did one thing *email*really well,” he said.

“But over the years it became slow, started killing battery life, and was getting bogged down by extensions. That’s why we wanted to create something that would be like if you were to build Gmail from scratch, but with today’s technology that was blazingly fast, visually appealing, and keyboard-driven.”

But what would be the secret sauce that made all of this work?

Going back to his roots, Vohra started from first principle as if he were going to build a highly entertaining, maybe even slightly addictive, video game.

Game-like experiences will ride the next big wave in tech

Today, many companies are trying to build “Superhuman for X.”

But as Mehdi Boudoukhane pointed out, it’s not quite as easy as it sounds. 

In Vohra’s case, his background and focus have enabled him to successfully create the delightful experience we associate with Superhuman today: an invite only, $30/month email service with more than 220,000 people on its waitlist.

Superhuman provides a delightful experience all the way to inbox zero using a deep background in game design.

As one of the first productivity tools to emerge with a game-like experience, Superhuman is uniquely positioned to ride the next massive wave in tech as video games become a driving force for mainstream consumer culture.

I predict we’ll see more game-like experiences emerge as gaming goes mainstream and more developers, founders, STEM students will lean into gaming best practices as they create new products – in the same way Vohra has with Superhuman.

There are already early, promising shifts in how we learn, collaborate and ship new software experiences. Figma’s multi-player technology and Repl.it’s real-time collaborative coding are early examples for developer and design tools, however I believe this is just the beginning and more will emerge across different teams, sectors and use cases.

The proliferation of gaming culture

Before we dive into the core components of a game-like experience, let’s look at early signals of the massive wave to come in gaming.

The gaming industry is now bigger than Hollywood. Americans spent $43B on video games in 2018 alone. Gaming culture will be increasingly synonymous with mainstream culture as professional gamers become celebrities, award shows celebrate game creators and streamers, and an explosion of new jobs emerge to support the gaming ecosystem.

The gaming tech stack is growing and well-funded. New platforms, leagues, content studios and a whole ecosystem of analytics, performance coaching and new technologies are emerging to support consumers, prosumers and professional gamers. There are an estimated 759 gaming related startups today.

The end of ‘game shame.’ Gaming has long battled a negative social stigma of promoting violence, misogyny and an often misunderstood camaraderie for the loners and socially inept, however increasingly video games are used in school to teach STEM and provide an alternative to traditional sports.

Research suggests girls who play video games are 3x more likely to study STEM. As games become more age, gender and geographically diverse, we will see a more inclusive ecosystem and a shift in the traditional ‘gamer’ stereotype.

In the few years, we’ve seen an influx of coding bootcamps and original programs like Kode with Klossy, a code bootcamp designed for girls 13-18, create more inclusive opportunities for underrepresented groups to study STEM.

I’m excited to see (and fund) original content such as video games and software experiences, especially those designed for women and underrepresented groups to expand their technical abilities.

The four components of a game-like experience

Getting a bit more down into the details on Superhuman’s video game approach, we can see how the team leverages video game-like engagement hooks and rewards that tap into intrinsic motivations of users.

There are four key components to the Superhuman experience:

Goal: To get to inbox zero. 

During their one-to-one onboarding session with new users, the Superhuman team observes how an individual interacts with their inbox and identifies stressful patterns of behavior, which informs how they encourage new users to work towards inbox zero.

“Most companies worry about what users want or what they need. But we don’t worry about that at all. We obsess about how users feel. We make users feel is just as important as what we make. And what we actually make is joy, in software form,” Vohra said.

More than anything else, Superhuman is a direct result of an intense focus on the emotions behind the experience that ultimately lead to delight.

Control: Keyboard shortcuts. 

These controls are taught to the new user during an onboarding session and help them quickly navigate through the tool and execute tasks more quickly when using it.

While Superhuman didn’t invent shortcuts, it created a more approachable and popularized version of command line shortcuts that developers use daily.

I call this the “consumerization of the command line,” a shift in how users interact with their devices where a command line interface and use of keyboard shortcuts is used to remove distractions and increase productivity in a single session.

Since the launch of Superhuman, we’ve seen Command E, keyboard shortcuts to search and open any document, and Linear, a streamlined bug tracking tool and modern alternative to Jira.

Tutorials: Training.

This is the functional onboarding where the user gets to hang out with the Superhuman team, learn the controls, and is shown the goal, all within a safe environment with a friendly person who’ll help you as you try out the controls and use new moves.

Like any good game, many superfans have designed their own ‘cheat sheets’ and share their personal hacks on social media with other fans.

For games and most productivity tools, “just enough” training can be achieved through a few onboarding screens and a standalone Discord community for users to learn from self-serve education and other users.

Pace: Speed.

A good game flows smoothly and consistently builds momentum and speed as the user becomes more experienced, which is why Superhuman has focused so intensely on speed. They help users maintain a state of flow and focus with more speed and less cognitive load than other email clients. Users are immersed in the experience.

“With these elements in place, you have the perfect ingredients for what is essentially a video game–and then you can start to layer things on top of that. One of the ways we do this is the name itself: Superhuman. Users are the superhumans; they’re the main character in the game–and by playing it, they become brilliant at what they do,” Vohra said.

Conclusion: While video game design in the context of workplace productivity is still fairly new and experimental, the core components bring a refreshing approach to building better products at work.

Research suggests more than half of all employees are unhappy at work because of the software tools they’re using.

I hope to see more design elements inspire new tools and processes such as keyboard shortcuts and real-time collaboration that seamlessly integrates both “single player” and “multiplayer” modes to make work increasingly feel more like a game.

What’s next for Superhuman?

Looking ahead, Superhuman plans to double down on single player mode. 

The reason: Vohra is more interested in horizontal teams than vertical teams, and wants to see what it looks like when all of the executives and leadership roles within a company are using Superhuman. This means rather than focusing on building new team collaboration tools, their existing features may just be tweaked and marketed differently down the road.

“I’ve always believed it’s worth it (although probably harder) to absolutely nail the consumer single player use case before you start going into teams. So we’re very much like Dropbox and say, ‘Let’s nail that single player experience first,’” Vohra said.

In the future, the Superhuman team will spend about half of its time doubling down on the things that users love and the other half of the time systematically overcoming objections to adoption from the target market.

Watch the full discussion & please say hi on Twitter!

I’d love to get your thoughts and feedback.

The Angel J-Curve: Super Connectors, Workhorses, Show horses in tech

How operators get their wings in Silicon Valley 

I joined my friend Harry Stebbings on a recent episode of 20VC to discuss trends in early stage investing including the state of scout funds, the whitespace for “triple threats” who operate, angel invest and have their own beat on social media and why I believe more operator angels should start their own funds.

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In this essay, I’ve split the discussion into a few key phases with tactical suggestions for each phase.

While there’s no single path to start investing, The Angel J-Curve is a guiding framework to better understand the opportunities available for operators in Silicon Valley based on your time and revenue (social/working capital) in the ecosystem.  

Where are you on The Angel J-Curve? 

Let’s start with a definition of each phase and high-level overview before we move into tactics and recent examples: 

Super Connectors: early career operators who seek high-growth opportunities such as startups on the Breakout List³ or look for well-funded startups backed by a16Z, Sequoia and top-tier firms. These operators build a broad network that later converts to professional opportunities, such as an internal referral at a hot company or opportunity to invest in a friend’s company.  

Tldr: Social capital converts to professional opportunities

Workhorses: operators who build a track record and reputation by helping early stage startups on evenings & weekends. Capital can come from a number of sources including small personal checks, scout funds and some choose to raise outside money as Operator Angel Funds

Tldr: High value per dollar invested based on operator angel’s skill/sector/stage alignment 

Show horses: super angels with a trusted reputation and proven track record based on breakout tech experience and subsequent breakout angel investments. While many still operate with similar characteristics as a Workhorse, the real value is in their signal to other investors. 

Tldr: High social signal irrespective of sector/stage/dollars invested 

What are the guiding principles for each phase? 

Based on your time and revenue (social/working capital), there are a number of guiding principles and baseline activities to build a track record.  

Super Connectors: 

For Super Connectors, geographical location and a hyperlocal network is an important factor to accelerate social & knowledge spillover. 

These operators learn by simply being exposed to other super connectors, workhorses and the occasional show horse at an event or conference. 

Silicon Valley has the highest concentration of early stage startups and hyper compressed environment for Super Connectors who want to accelerate both professionally in their tech career and socially as an angel investor. However, many operators outside of the Bay Area have built a reputation through tweeting, blogging and podcasting. We’ll look at examples from both Silicon Valley and beyond.  

Without working capital, Super Connectors build a reputation using social capital and ‘cool as a currency’ meaning these operators have a unique ability to discover new products, spot trends before they blow up and build, ship and share on social media.   

A few baseline activities for each phase: 

  • Build, ship and share on social media

Twitter is a great place to start, however SubstackDev.to are great places to further develop ideas and build an audience. 

  • Find your beat aka “be known for a thing” 

Breakout Super Connectors become a go-to person for a specific topic, sector or area of interest, which requires consistent publishing around a specific topic. 

Founders building in the space and investors should be able to articulate your beat in a few words, so others can easily seek you out based on your known expertise.

  • Optimize for a high-growth experience

Choose your next career move based on where you’ll have outlier potential with high-growth experience and a valuable network of Super Connectors. 

In the first two years in the Bay Area, the relationships you build will influence your view of the world and your professional opportunities in the future.   

Look for entrepreneurial cultures where the person sitting next to you is likely to start something new. 

If you’re a Super Connector, say 👋

I host a monthly happy hour in SF and would love to follow your newsletter and compare notes on your beat. 

A few Super Connectors to follow: 

@sarthakgh

Sar has mastered the power of Tech Twitter. 

In a matter of months, his name was consistently mentioned in coffees with founders, Monday partner meetings at VC firms and he’s consistently tagged in relevant conversations on Twitter. 

Sar is by all accounts a Super Connector or as I call him the DJ Khaled of Silicon Valley: he knows everyone, hypes everyone and gives up-and-comers more visibility.

He reads a tweet, jumps in with relevant commentary and tags individuals who have recently shared similar ideas or have deep expertise in the space.  

A lot of great original thinking gets lost in the Twitter feed, so Sar’s ability to invite relevant people to a discussion is incredibly valuable.  

@HipCityReg

Reggie’s newsletter Product Lost covers things he’s seen, heard and experienced (typically well before anyone else). While his discussions are not directly startup or business strategy related, it consistently delivers big ideas and new opportunities for founders and investors to explore.   

@HarryStebbings

Harry started 20VC long before he started his own VC fund. 

One of his secret weapons for building his network is sending cold emails. Before every episode, Harry emails founders, investors and mutual friends to prepare for each guest.  

Workhorses: 

For early career Workhorses on their first or second startup, this is where you start to cultivate a more strategic network based on your beat. 

  • Build your intercompany peer network

Want to be known as a go-to product person? 

Make a list and meet every product person at breakout companies. 

Find something to work on together: organize a monthly dinner, host office hours for startups, any excuse to get together on an ongoing basis. 

  • Advise for free or minimal equity 

The best advisory relationships happen organically and will likely come from your Super Connector network, however if you’re new to advising startups you can seek out opportunities to help startups that are one to two funding rounds behind your current startup. 

In this phase, optimize for experience and build/iterate on your offering as a startup advisor. 

During this phase, I taught classes at General Assembly as a way to build my own offering and continuously iterate after each class. 

After 4 years, I had taught over 5,000 students without ever writing an angel check. I did however amass a mailing list of 8,000 readers through consistent coverage in General Assembly’s mailing list. 

  • Start writing $1-5K checks 

If you’re a helpful operator, there is rarely a minimum check size. 

Start to build a small, concentrated portfolio and remember your check size can easily scale up or down based on your personal working capital and conviction level based on relationship with entrepreneur and your skill/sector alignment. 

At this stage, your goal is small checks into pre-seed companies especially founders before they apply to YC or similar program that serves as a strong signal for future investors. 

For later career Workhorses, this phase requires consistent, compounding activities that both strengthen your existing networks and create access to startups outside of your immediate network. 

By this point, you’ve had a number of shots on goal and likely have access to a number of alumni syndicates to invest in founders that you’ve worked with directly or have enough first degree connections to get to conviction quickly when referencing the founding team. 

A few baseline activities for this phase: 

  • Subscribe to alumni syndicates, newsletters and events
  • Determine scout potential: if you’ve been an operator at a breakout company or have coverage across a number of startups, reach out to VC firms to gauge scout interest. 
  • Prioritize external visibility: To become a magnet for startups, you’ll need top of mind awareness and visibility in the ecosystem 

This exercise is different for everyone. If writing or speaking at conferences is not your thing, choose to work on external facing projects. 

For me, I made the strategic decision to work on startup-facing products at Zendesk which included Zendesk Apps Marketplace and building Zendesk for Startups for broad startup coverage and an accelerated strategic network, which included partnering with incubators, accelerators and VCs. 

In parallel, I spun out of General Assembly and used the same content to start my own program called SaaS School. 

Rather than building this alone, I asked my intercompany peer network to join me including product leaders from Dropbox, Drift, Slack, SurveyMonkey and other operators I had previously met at SaaS Growth events hosted by a friend/mentor Guillaume Cabane at Segment. 

Because there’s a great deal of nuance when it comes to scout programs, self-funded angel portfolio construction and the rise of Operator Angel Funds, I will cover this in-depth in future posts. 

In the meantime, here’s the deck I used to raise $5M from Marc Andreessen, Eric Yuan and early investors in my new fund Work Life. 

Show horses: 

The most common Show horses are growth stage and post-IPO CEOs who both LP in Operator Angel Funds and continue to invest on a deal by deal basis. 

Show horses are well capitalized and typically build a concentrated portfolio of Series A+ investments. They have access to the best deals via their existing relationships with top-tier firms and strong CEO network. 

In recent years, many Show horses have hired a dedicated Workhorse to serve as an investment partner to both meet early stage companies and help scale their portfolio support while they continue to operate a high-growth tech company. 

Now, where does this leave the Silicon Valley Elite? 

The Angel J-Curve is a guiding framework with a fairly linear path for any operator who wants to build a track record as an angel, so by definition the Silicon Valley Elite are an exception to this model.

For simplicity’s sake, the definition of Silicon Valley Elite is defined as outlier operators who are part of a collective ‘Mafia.’

Some Show horses may swing in the same social circles as the Silicon Valley Elite, which means they have similar access however they do not benefit from the compounding advantages of the ‘Mafia’ network: first look at alumni founders and ability to compete head-on with ‘Mafia’ peers at other top-tier firms.

If you’re based in Silicon Valley, say hello @briannekimmel!

I host a number of angel dinners and events throughout the year for angel investors across all phases of The Angel J-Curve.

“free” can attract the wrong users. Find out if freemium is right for your startup with Slack Head of Self-Serve Fareed Mosavat

In this talk, Slack Director of Product Fareed Mosavat will share his framework for building freemium business models.

You’ll learn the 5 criteria to determine if a freemium business model is right for your business:

1. Do you have access to lost cost acquisition channels?

If not, start by building an acquisition engine An acquisition engine requires a deep understanding of users: content, competition, cross-company virality

“Paid marketing & freemium are oil and water”

2. Is there a quick activation path?

If not, make onboarding a core priority. Free users require fast activation or else they’ll churn or remain dormant forever

“Free can attract the wrong users, activate the right ones ASAP”

3. Do you have internal growth loops?

If not, expand into multi-player features. Build features that enable collaboration, cross-team visibility and unlock value for managers.

“Teams are inherently collaborative, but we have to productize it.”

4. Is your core audience empowered to purchase?

If yes, remove as much friction as possible – Optimize your pricing page – Self-serve add-ons & upgrades (no sales rep needed!) If no, find ways to work around procurement and manager approvals”

5. Is there a clear value metric?

Determine your first value metric and create a conversion at this moment. Value should increase over time, but start you need to start somewhere! “Premium features are hard to anchor on!”

This talk was originally created for SaaS School, an invite-only program for entrepreneurs to learn from the fastest growing software companies like Airtable, Dropbox, Drift, Slack and more.


Why the next professional network will look nothing like LinkedIn

As LinkedIn unbundles, SaaS companies emerge as leaders of the new professional networks

LinkedIn, now in its 16th year, was built for a different era where professional ability was confined to a resume and recruiters served as gatekeepers between professionals and hiring managers.

Resumes, career fairs, networking events, professional organizations…

If the new American Dream is defined by “creative expression, online influence and extreme optionality” over linear moves up the corporate ladder, then LinkedIn is enough to make any Millennial or Gen Z jobseeker cringe.

Today, we’re seeing an “unbundling of LinkedIn” with a whole ecosystem of programs, services and technologies to better serve the 500 million+ professionals across different geographies, sectors, interests.

In this essay, we’ll explore:

  • LinkedIn: first to market with enduring network effects
  • What’s broke? 75% of LinkedIn revenue comes from recruiters
  • Why the resume is dead and what’s next
  • SaaS companies emerge as the new leaders of professional networks

LinkedIn: first to market with enduring network effects

LinkedIn started as the first social network for working aged adults and scaled into an enduring platform that has outlived its consumer social peers (Friendster, Myspace). Long before YouTube, Facebook, Instagram, there was LinkedIn.

LinkedIn benefits from two key factors:

  • Strong, enduring network effects: steady stream of students who enter the workforce each year, job hopping and career changes increase engagement
  • Highly monetizable beyond traditional ads: ability to charge consumers (jobseekers) and businesses (sales, recruiting, marketing) for premium features and services

What’s broke & new opportunities to displace LinkedIn

To truly understand how a platform works, examine how it makes money.

In the early days of LinkedIn, its ability to generate significant enterprise revenue was a core differentiator compared to other social networks which have limited forms of monetization beyond standard ad units.

But in the same way that the consumerization of enterprise technology has given individuals more freedom, choice and control over the tools they use at work, LinkedIn’s loyalty to recruiters comes at the cost of a better end-user experience.

The end-user experience goes down as the number of InMail from sales reps, recruiters and marketing campaigns goes up.

Today, up to 75% of revenue comes from employers and recruiters. And it shows.

What’s broke? The resume.

While the resume is a fairly accurate snapshot of professional credentials.

It fails to reflect true potential such as grit, ability to collaborate with others and professional skills developed on evening and weekends.

Much of LinkedIn’s value today is in its ability to link to Dribbble, Github, Substack and new platforms with shared skills and a thriving community to critique your work.

New opportunities include: 

Professional networks with shared interests and emphasis on peer education: Dev.to for developers, Girlboss for female business owners. 

Where people want to hang out on evenings and weekends. 

Professional networks with peer reviews and recommendations: TrustedFor for suggesting in-network experts for specific projects. 

Where shout-outs are fun and feels more like a social network than writing performance reviews. 

Professional networks where individuals can build their own services business with public profiles and reviews from happy customers.

Where your hobbies and side projects can turn into meaningful extra cash. 

Moonlight matches developers with creative side projects and opportunities to “moonlight” outside of their current role using a pseudonymous profile with professional experience and community reviews.

Developers spend up to 20 hours a week on technical debt and fixing bad code, the ability to find interesting projects outside of work is accelerated learning and career progression that’s not dependent on current employer.

What’s broke? The promised land that lives behind a paywall.

Want to connect with like-minded people on LinkedIn, apply for jobs or find better work? It’ll cost you $29.99/month. 

A free plan on LinkedIn offers only the ability to see the last 5 people who have viewed your profile.

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New opportunities include: 

SaaS tools that deliver daily utility emerge as the leaders of new professional networks.

By adding a public facing profile and the ability to share your work ie: open-source designs, templates and projects, SaaS tools that invest in community can deliver a better end-user experience that’s inherently sticky.

When users build a portfolio, grow their following and contribute to the community, they build a personal track record and bring the tool from one job to the next (BYOT).

Example 1: Figma Community

The ability to “Publish publicly” has been integrated into the core workflow and requires two clicks from the user. 

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Example 2: Webflow Community

The ability to share your work, build an audience and allow users to clone your work.

A single user can see 25K+ views, 10K+ comments and 1K+ clones.

Power contributors can build a following, find new work and contribute new work to the community independent of their current employer.

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As SaaS companies expand from tool-based utility to professional networks, companies will measure user retention (from job to job) in addition to traditional employer focused metrics (logo retention).

The best networks will play an active role in how users make their next big career move through user conferences, branded Slack channels and curated events.

As LinkedIn continues to unbundle, we’re entering an era of productivity, collaboration and creativity where the new professional networks are not new at all. They’re the tools we use everyday.

I’d love to hear your thoughts on the unbundling of LinkedIn and new opportunities for professional networks. Say hi on Twitter: @briannekimmel