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, 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,, 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

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.


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

Why hourly work is more creative and flexible than ever

TikTok for retail jobs, nail technicians with Hollywood agents & tattoo artists on world tour

Over the last decade, hailing a ride through an app, getting your favorite meal delivered, or having new furniture assembled at your convenience has become an affordable convenience for the average American. 

While the services provided by these well-funded Silicon Valley startups have enabled massive productivity gains for busy working professionals and consumers on the demand side of these technologies. In recent years, “gig” work has received its fair share of criticism due to its opaque wages and unfair labor practices as companies aim to cut labor costs and maintain an affordable service for customers.

As we look ahead to the next decade, I take an optimistic view on new opportunities for hourly work in the Roaring 20’s as more creative work becomes readily available across all skill levels.

In the same way that influencers and celebrities are using social influence to launch their own podcasts, jewelry lines and venture-backed startups, we’re seeing modern tradespeople such as mixologists, hair stylists, freelance designers and self-taught software engineers build meaningful businesses off the back of social platforms like Instagram. 

The virtuous cycle for modern trades starts with the delivery of an Instagram-worthy experience that’s praised by others, studied by peers and attracts more opportunities for future work.

With the help of Instagram and other platforms, creative tradespeople are bypassing licensing and other limitations by connecting directly with top clientele on social media and creating scarcity through multi-cities tours to meet fans and offer their services via a pop-up experience or private bookings.

In this essay, we’ll discuss: 

  1. The backlash on policies meant to protect freelance workers

  2. The 4 categories of flexible work 

  3. The tech and tools to enable flexible work

  4. Three predictions for the future of flexible work

The backlash on policies to protect freelance workers 

As freelancing gains significant momentum with high-earning sectors, we expect Uncle Sam will be watching these new classes of work closely under the guise of protecting workers, without really understanding the work at all.

While many new startups will emerge to support freelancers and flexible work with accounting, scheduling/time management, flexible health insurance and more.

The state of California — home to two of the largest markets for specialized independent professionals: LA and SF — made the first real attempt to protect freelance workers by introducing limitations to employers in efforts to create full-time employment which left both parties annoyed and confused:

One section of California Assembly Bill 5 (A B5) caps submissions from any “freelance writer, editor, or newspaper cartoonist” to 35 per year. 

A recent study by Contently surveyed 573 freelancers about CA AB5 and found the following:

  • 88% oppose AB5’s provisions limiting freelance creative submissions

  • 75% freelance because they prefer it over a full-time work

  • 82% are opposed to a cap on freelance submissions of any kind

When the government takes aim at the gig economy, it’s not corporations or the services they provide that are under attack, it’s real people.

In Los Angeles alone, there are over 400,000 gig workers who collectively earned more than $18 billion last year.

Freelancers affected by AB5 are sharing their stories on Twitter with the #AB5stories hashtag. It’s independent musicians losing performing gigs, full-time caregivers who need flexibility, and individuals with disabilities making their own way. One freelance writer put their concern succinctly: “#AB5 makes me feel like collateral damage in the war against Uber and Lyft.”

Here’s what the bill missed: many people actively choose flexible work. When laws remove these options, they’re taking away economic and creative opportunities: temporary relief, supplementary income, flexible part-time income and more. They eliminate paid creative work and income in support of creative work. 

The battle cry for work that falls outside 9 to 5 is too loud to ignore. With it, we’ll see technological innovation and a new class of tools to support independent contractors, creatives, and anyone else searching for their next side-gig. The future of work is flexible; let’s take a glimpse at current and emerging trends.

The Four Categories of Flexible Work

Flexible work exists across four main categories: Classic Gigs, Modern Trades, Creative Experts, and Me as a Service (MaaS). Each category is distinct and has its own specific characteristics. Additionally, individuals can jump categories one as they develop particular skills or as they become more selective. 

Classic Gigs: offering time and some muscle for extra cash

Before the rise of peer to peer apps, we had the classified section of newspapers and then the emergence of Craigslist. Anyone from babysitters to handymen could post an ad offering their services. 

These gigs are tried and true classics that have served as a right of passage for teenagers first entering the workforce and a familiar archetypes for Hollywood’s answer to wholesome American culture.

Although we still appreciate the classics, they’re not fully protected from disruption – the ease and convenience of driving your own car with Uber and Lyft presents a new opportunity for flexible work on your own schedule. 

The barrier to entry is low and making meaningful money generally requires regularly accumulating a number of smaller paid tasks (e.g. x number of rides or x food deliveries). Individuals finding flexible work in the Classic Gigs category increasingly don’t need to advertise; the gigs flow to them in exchange for a flat fee per gig or percentage of your earnings. Additionally, you may earn tips.

  • A DoorDash delivery driver earns a fee for each food order they pick up from a restaurant and deliver to a customer.

  • A Handy service professional secures payment for services like home cleaning and television mounting.

Modern Trades

Skilled mixologists, make-up artists, and tattoo artists fall under Modern Trades.

The services they provide have a higher barrier to entry because they're trained in a particular field either traditionally through a school or apprenticeship or non-traditionally through hours of self-taught education through Instagram and YouTube. 

Today, rather than handing out business cards or attending trade shows, individuals in the Modern Trades category use platforms like Instagram, Facebook, and other social media platforms to build a following, connect with peers and access more work.

While they use online services to promote their work, they generally provide their services in-person and face-to-face. 

  • A specialized nail technician might pay for space to see clients in an established salon, but is self-employed and showcases their nail art through Instagram.

  • A magician for hire might post videos of their stunts and tricks on YouTube to drive bookings for corporate and private events.  

@thehangedit is an LA nail technician represented by NailingHollywood.   

Creative Experts

Creative Experts are who we generally classify as “freelancers” in tech – freelance designers, freelance software developers, or freelance writers. In this category, the barrier to entry and level of expertise can vary wildly. While a novice brand designer can get their start on Fiverr and producing a logo for a low fee, an experienced designer can command thousands of dollars for the same task if they have a portfolio of past work and a differentiated style that’s sought after.

To earn top dollar, specialization and differentiation is key: a known portfolio, peer recognition that leads to conference talks and industry press are all assets.

Generally, Creative Experts deliver their services digitally and their work for clients can be done entirely remotely.

  • Alice Lee (@ByAliceLee) is a freelance illustrator turned muralist who is credited for developing the people illustrations used by many enterprise companies today (see @HumansofFlat for inspiration). She’s worked with companies like Slack, Cruise and Philz Coffee and bounces between San Francisco and Venice.   

  • Aristide Benoist (@AriBenoist) is a freelance developer who specializes in motion graphics and interaction with clients including Epicurrence and Folio. 

@ByAliceLee’s original work with Slack.

See Taylor Swift as SaaS illustrations here

Me as a Service (MaaS)

Me as a Service (MaaS) is the newest entry to the flexible work spectrum. Under this category, people trade off their name and established brand by earning income through streams like Patreon, Substack, a blog, a podcast, or an online storefront. 

Here the “product” is the individual or something they’ve written, spoken, curated, or created. This category relies on influence and people caring about what you say or think in a particular niche. Customers, often “fans” or “supporters”, provide payments directly to their favorite creators as a one-off transaction or a regularly recurring subscription fee.

  • Cassidy Williams (@cassidoo) has a popular newsletter and Patreon and is known for her technical knowledge and funny quips on software engineering. 

  • Julia Evans (@b0rk) packages technical content into helpful web zines. While it was a side project for several years, she recently left Stripe to pursue creative work fully. 

This category is increasingly broad and spans across niches like productivity and self development, political commentary, or academic discourse. 

MaaS represents the only category where individuals shift from earning with their time to earning while they sleep. Patreon or Substack allow anyone in the world to subscribe to your content. These platforms are truly scalable and can generate true wealth through flexible work (e.g. writing a weekly newsletter or filming videos). 

While these four categories have always existed in some form, they’ve become increasingly democratized as tech tools can provide access to a steady flow of gigs, help you inexpensively build a website to showcase your talent, or enable a company of one to reach thousands of people with an Instagram snap and a few well chosen hashtags.

The Value of Flexible Work

The reasons that people opt for flexible work, and will continue to do so in the future, are diverse. There are four key reasons we can discern: the Chicken-Egg Dilemma, Lifestyle Flexibility, Antifragility, and Creative Expression. 

Chicken-Egg Dilemma

Flexible work is an opportunity to more easily acquire experience to put on a resume to leverage for full-time employment. This mitigates the “chicken-egg dilemma” in which you need experience to get a job, but need a job to get experience. For instance, flexible work can help students build portfolios to secure their first internships or new graduate roles. Employers increasingly want to see what prospective employees have done, not what they can do. Flexible work is low barrier and low permission. By choosing flexible work, individuals can quickly develop cross-functional soft and hard skills – stringing together daily gigs is time management and organization, while advertising your business online makes you a marketer. 

Lifestyle Flexibility

The mainstay of “work hours” from 9 am to 5 pm locks many people out of full-time employment. It’s often infeasible for parents, primary caregivers, or people with disabilities. Alternatively, many simply desire lifestyle flexibility, wanting to experience some semblance of the 4-Hour workweek, or at least a 4-hour workday. Flexible work enables people to break the constraints of the long commute and office day. Instead, they can earn an income while simultaneously raising kids, taking care of an aging parent, or travelling the world.


Flexible work provides a means to work with interesting people, build your network, and gain more skills. In a fast moving economy, the ability to develop a body of work that precedes you represents stability and freedom. It makes you antifragile. Increasingly “building a personal brand” isn’t for marketers or entrepreneurs; it’s advice for everyone – academics, technologists, and everyone in between. Having a website, portfolio, blog, or Twitter account to point to can spurn work opportunities and serves as insurance in the case of job or income loss. 

Creative Expression

People are disengaged at work. 

Gallup’s 2017 State of the American Workplace Report found the following about the country’s 100 million full-time employees:

  • 16% of employees are actively disengaged — they are miserable in the workplace and destroy what the most engaged employees build.

  • 51% of employees are not engaged — they’re just there.

This disengagement exists for several reasons. Here’s just one: many people are unable to align their passions with their full-time work. Flexible work is a way to seek out passion projects that serve as a creative outlet. These can permanently supplement full-time work (e.g. “side gigs”) or they can be a bridge to transition to creative work in the future.

Alternatively, flexible work can support creative work that doesn’t generate income or costs money. The trope of the struggling actor waiting tables is now the striving actor who manages brand accounts on the side in between auditions.

The Tech and Tools Enabling Flexible Work

There’s an expanding canon of tools that are enabling flexible work across Classic Gigs, Modern Trades, Creative Experts, and MaaS. More so, it looks like the market opportunity for work tools and platforms is only growing.

Platforms like Indeed are part of the present-day pack of successful work tools.

However, there’s room for a new set of well-designed workplace tools and platforms that provide an elevated user experience for both employers and candidates. Additionally, there’s an opportunity for freelancer and creator focused-tools that help flexible workers find their next big project. 

The “workplace tools category” extends far beyond the next Slack or the next Zoom – it’s a wide grouping that’s ready for disruption and newcomers. These are the categories of tools we can look forward to seeing.

New marketplaces for flexible work opportunities. Beyond rideshare and delivery, marketplaces will arise across different sectors. Tend (a WorkLife portfolio company), a marketplace for highly-skilled hospitality and entertainment workers, helps anyone from mixologists to cooks get additional hourly shifts in cities like San Francisco, New York, Miami, and more. 

Tools innovating on hourly work. Hourly work remains a prominent part of the economy, and an area where tech tools will bring new opportunities and experiences. Heroes (a WorkLife portfolio company) lets prospective employees create short personality-driven videos to apply to customer service roles at companies like American Eagle, H&M, and Jamba Juice. Think TikTok, but for getting hired at your favorite store like REI (if you’re outdoorsy) or Sephora (if you’re addicted to beauty). 

Tools enabling creators. We’re going to see more companies like Patreon, Podia (a WorkLife portfolio company), Substack, and Gumroad. While each platform has their own specific value proposition, their commonality is in helping creators monetize their knowledge and skills by helping individuals offer exclusive content through subscriptions or paid courses. We’ll see more companies like Beacons, an influencer marketing platform that lets creators monetize through short video interactions with their fans. Similarly, Bunches lets anyone set up and monetize a group chat about anything and represents a shift to more intimate communities. 

Tools for remote work. The rise of flexible work will correspond with the continued elevation of remote work. Flexible workers can increase their client base from a city to a country and beyond. Tools like Tandem (WorkLife portfolio company) will provide a means to connect remote collaborators through a virtual office. Additionally, collaborating with anyone you want, regardless of their time zone, is increasingly possible with asynchronous tools.

Communities will be the new professional networks. I’ve suggested that the next professional network will look nothing like LinkedIn. Communities like, Elpha, Girlboss, Webflow Community, and Lunch Club (all WorkLife portfolio companies) will redefine what networking for a job and connecting with prospective employers and employees looks like. These communities will serve as a place to find high skill gigs, potential collaborators, and prospective clients.

Tools to showcase work. We’ll see more tools like Dribbble and Behance for showcasing design work and platforms like GitHub for documenting open source contributions. Aside from work specific tools, we’ll see new platforms that are co-opted to showcase professional work (e.g. Instagram). 

Tools unbundling Patreon. Currently the platform is a catch-all for creatives – visual artists, writers, gamers, and everyone in between. Offshoots of Patreon that are niche-specific will arise (e.g. “Patreon for Academics” or “Patreon for Singers”).

Tools to start a business, quickly. The rise of flexible work means more Founders. We’ll see services to reduce the overhead, cost and complexity of starting a solo business (e.g. Stripe Atlas for Creatives).

Three Predictions on the Future of Flexible Work

It’s not only novel tech that will emerge as fixtures of the flexible work revolution. We’ll see a renaissance that extends beyond SaaS tools and permeates into the economy, physical spaces and how companies do business.

  1. We’ll see innovative healthcare plans to support freelancers. One reason people cite for not starting their own business is losing their employer provided healthcare. Private insurance remains complex and often out of reach. New developments in health care plans for freelancers will provide a corresponding boost in the economy as people start businesses, find success, and go on to hire others.

  1. Physical spaces for creatives. As flexible work makes traditional offices less important, people will still want a place to connect with peers and network in person. Despite the fall of WeWork, franchise and independent creative spaces, like The Wing and Ethel's Club, will continue to pop up as less people work in traditional offices. Big events like ComicCon, Vidcon, and the Girlboss Rally will grow in significance and act as modern day pilgrimages where individuals can congregate annually with like-minded people to discuss their passions and find new inspiration.

  1. Traditional companies will compete more aggressively for talent. Both legacy institutions and startups will compete more aggressively for talent as the power shifts increasingly to highly-skilled individuals. Similar to the Screen Actors Guild in Hollywood, industries like software development and design are seeing their own guilds and collectives form – both as a professional network and a trusted source of information on fair pay and labor rights. Moonlight, a professional community for software developers, helps professionals find jobs and engage with other remote developers. Employers will need to offer greater schedule flexibility and soften non-compete clauses to allow for side projects. The 2016 Deloitte Millennial Survey found “75 percent would like to start to, or more frequently, work from home or other locations where they feel more productive.” We’ll see companies try to turn full-time employment into flexible employment by offering more remote work opportunities. Employers will also turn to services like Dover (a WorkLife portfolio company), to increase their talent pipeline and staff talented employees.

I’d love to hear your thoughts on flexible work and new tools enabling more creative and flexible work. Say hi on Twitter: @briannekimmel

Why founders killed the friends & family round

Building on last week’s discussion ‘the hard work for the oversubscribed’ with an open discussion below:

As more founders replace the friends and family round with the new operator-angel round to de-risk technical dependencies, accelerate time to launch and build momentum for the next round.

Slack’s head of self-serve product Fareed Mosavat on why early stage SaaS companies need to measure more than early-stage investor metrics. Subscribe to get the full deck delivered to your inbox.

The 3 goals of an operator-angel round:

  1. Accelerate your startup’s time to market by driving strategic alignment with core integration partners and founders/operators who can open doors quickly.

  2. Augment your team’s current capabilities with operators who can immediately deliver a high value per dollar invested through a focused body of work and immediate access to network.

    • Choose angels based on relevant operating experience

    • Create goals and focused body of work to leverage an individual angel’s superpower

    • Continue to build momentum with angel until your startup has enough momentum to hire someone full-time. Leverage angel’s peer network to source, vet and onboard someone full-time

  3. Act on first mover advantage and engage high-signal angels in a way that new entrant’s will be viewed as a fast follow with a low chance of becoming the category leader.

    • Build your sector-aligned CEO network to establish credibility with users & investors

    • Leverage early investor alumni networks to scale hiring momentum & culture

    • Box out competition with a bottom-up community of early believers and evangelists

Leave your questions/thoughts/comments below:

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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, Girlboss and Webflow. 

  • A trusted network of co-investors I had developed from angel investing and a growing portfolio with sector-aligned founders and early employees who quickly help founders navigate specific challenges and pivotal moments for the company.

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

Building a foundation for institutional LPs

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

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

(Image via the The State of Family Offices 2019)

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

  1. Have sector-aligned CEOs get involved from the very beginning, including Eric Yuan from Zoom, Stewart Butterfield from Slack, Clark Valberg from InVision, Nick Mehta from Gainsight and many more. 

  2. Learn from “super angels” who started their own funds and managing directors of top-performing funds. 

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

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

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

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

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

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

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

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

Discovering WorkLife’s identity

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

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

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

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

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

A gap in the market

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

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

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

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

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

The thesis: future of work

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

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

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

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

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

The future of work needs more than software

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

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

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

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

From WorkLife’s Instagram: @worklifevc

Brianne’s advantage: competitive analysis

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

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

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

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

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

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

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

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

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

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

You can subscribe to Brianne’s newsletter here, and follow her on Twitter here.

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Welcome to 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 cultural shifts that have defined the past decade and study market signals of 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 larger market cap 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 counterintuitively, 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, production for podcasts & original videos, 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.

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 new social platforms. We can expect more to break 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:

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

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