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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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

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

As an operator and active angel investor, I left Zendesk a year ago to build Work Life, 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 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

Work Life 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.