In the beginning, VFA was an institution beloved by many of its fellows. “It was a wonderful way to leave college and enter the real world because you’re surrounded by a community and there’s support from the organization,” says Jamie Norwood, co-founder of feminine hygiene brand Winx Health. Norwood and her co-founder, Cynthia Plotch, are a VFA success story. They met as fellows in 2015 and VFA eventually helped them launch their company with a grant and advisement. “We always say, Winx Health would not be here without VFA,” Norwood says.

Norwood and Plotch went through the standard VFA admissions protocol, which was rigorous. It required two written applications, a video interview, and in-person interviews at an event called “Selection Day,” many of which were held in New York City and Detroit over the years. By the end of each university term in May, accepted fellows would get access to Connect, VFA’s job portal, and have until November to land a job. For each fellow hired in a full-time job, VFA received a $5,000 placement fee, paid by partner companies. This fee became a crucial revenue stream for the organization—effectively wedding the professional success of its fellows to its bottom line.

Selection Day interviews were conducted by judges who often pitted interviewees against each other. Candidates were told to organize themselves in order of least to most likely to be successful, or according to whose answers had the most value per word. The format felt ruthless. “People cried” during the interview process, Plotch remembers.

The problems with the business bled into the fellows’ experience in 2023 and 2024, leaving them disenchanted, financially struggling, or expelled en masse from the program for reasons they believe were beyond their control. Despite a multitude of financial red flags, VFA leadership still insisted on recruiting for the 2024 class. “The talent team was traveling nonstop, using prepaid Visa cards since the corporate cards didn’t work,” explains a former director who worked closely with fellows.

Onboarding fresh recruits became increasingly crucial if VFA was going to survive. The organization asked companies for placement fees upfront in 2023, according to internal VFA documents and conversations with former employees. The policy change gave companies pause. Fewer companies signed up as partners, meaning fellows weren’t getting jobs and VFA was losing money.

In the spring of 2023, “there were 15 jobs on opening day,” for a class that eventually grew to over 100 fellows, the former director explains. Gabriella Rudnik, a 2023 fellow, estimates that when training camp began in July 2023, less than half of her peers had jobs, “whereas in previous years it would be closer to like 80 percent.”

Fellows were made to pay the price for the shortage of companies partnering with VFA in 2023. “We weren’t getting more jobs on Connect, and that’s what led to so many fellows being off-boarded,” explains a former director who worked closely with fellows.

Traditionally, VFA gave fellows a deadline of November of their class year to find a job, which typically meant a few stragglers were given extra help to find a position if they were late. In those rare cases during earlier years, fellows were offboarded by the organization, a former director says.

In previous years, expulsion was a much more serious and infrequent occurrence. “Removal from the fellowship was not something done lightly. During my tenure, we instituted an internal investigation process, similar to an HR investigation,” says the former executive who worked at VFA from 2017-20.  In total, at least 40 fellows from the 2023 class were expelled for failing to get jobs that weren’t available, according to research by former VFA fellows who tracked the number of fellows purged from a Slack channel. Records of their participation were removed from the VFA website, the fellows say.

Many fellows had made sacrifices to be part of the highly selective and prestigious VFA, which cited acceptance rates of around 10 percent of applicants. “There were fellows who turned down six-figure jobs to be a part of this program, and were told that the program that Andrew Yang started would live up to its reputation,” says Paul Ford, a 2024 fellow.

Though internal documents show that VFA was slowly imploding for months, in all external communications with fellows, the nonprofit still maintained that 2024 training camp would take place in Detroit.

“From an ethical perspective, it does reek of being problematic,” says Thad Calabrese, a professor of nonprofit management at New York University. “You entered into an arrangement with people who don’t have a lot of money, who believed that you were going to make them whole. Then you’re going to turn around and not make them whole.”

As a SaaS startup scales, sales and customer support staff pay for themselves, and the marginal cost to serve your one-thousandth versus one-millionth user is near-zero. The result? Some SaaS companies achieve gross profit margins of 75 to 90 percent, rivaling Windows in its monopolistic heyday.

Rent-seeking has become an explicit playbook for many shameless SaaS investors. Private equity shop Thoma Bravo has acquired over four hundred software companies, repeatedly mashing products together to amplify lock-in effects so it can slash costs and boost prices—before selling the ravaged Franken-platform to the highest bidder.

In the Kafkaesque realm of health care, software giant Epic’s 1990s-era UI is still widely used for electronic medical records, a nuisance that arguably puts millions of lives at risk, even as it accrues billions in annual revenue and actively resists system interoperability. SAP, the antiquated granddaddy of enterprise resource planning software, has endured for decades within frustrated finance and supply chain teams, even as thousands of SaaS startups try to chip away at its dominance. Salesforce continues to grow at a rapid clip, despite a clunky UI that users say is “absolutely terrible” and “stuck in the 80s”—hence, the hundreds of “SalesTech” startups that simplify a single platform workflow (and pray for a billion-dollar acquihire to Benioff’s mothership). What these SaaS overlords might laud as an ecosystem of startup innovation is actually a reflection of their own technical shortcomings and bloated inertia.

Over 1,500 software startups are focused on billing and invoicing alone. The glut of tools extends to sectors without any clear need for complex software: no fewer than 378 hair salon platforms, 166 parking management solutions, and 70 operating systems for funeral homes and cemeteries are currently on the market. Billions of public pension and university endowment dollars are being burned on what amounts to hackathon curiosities, driven by the machinations of venture capital and private equity. To visit a much-hyped “demo day” at a startup incubator like Y Combinator or Techstars is to enter a realm akin to a high-end art fair—except the objects being admired are not texts or sculptures or paintings but slightly nicer faces for the drudgery of corporate productivity.

As popular as SaaS has become, much of the modern economy still runs on the humble, unfashionable spreadsheet. For all its downsides, there are virtues. Spreadsheets are highly interoperable between firms, partly because of another monopoly (Excel) but also because the generic .csv format is recognized by countless applications. They offer greater autonomy and flexibility, with tabular cells and formulas that can be shaped into workflows, processes, calculators, databases, dashboards, calendars, to-do lists, bug trackers, accounting workbooks—the list goes on. Spreadsheets are arguably the most popular programming language on Earth.

Many people try out careers in venture and then wind up leaving after a year when it stops feeling novel and starts feeling like they’re floating in lonely limbo without any markers of success. That’s because the craft of venture is not for people who derive their satisfaction from external indicators of progress — it’s for people who find the development of their relationships and refinement of their internal model of the world to be motivation enough to keep going.

If you derive satisfaction from refining a craft, don’t go into venture yet.

Here are five individual investor archetypes I’ve noticed can produce outsized returns in the early-stage venture game:Philosopher: hangs one’s reputation on their predictions about the futureHustler: simply outwork everyone else and are great at networkingHawk: most competitive, gets a thrill out of the fight to win a deal Friend: confidante and coach to founders, often founders’ first callCelebrity: a person widely respected for their work/knowledge/skill

A good archetype for you is whichever one you can sustain the longest. A great archetype for you is one that no one else is doing and you have some sort of signal works.

Some good advice I got: build your fund’s structure and strategy around allowing yourself to invest in whichever way you most enjoy and are naturally good at (admittedly, it will probably get harder and harder to stick to this as your fund scales).

Examples: if you like being a friend to founders and want your fund to function as Switzerland (i.e. not compete with anyone), write small checks. If you like to fight and are naturally hawkish, it might make sense to set yourself up to try to lead rounds. If complex problems and futuristic theories are what get you excited, investing in series A companies that fit into where you see the world going could be quite gratifying. If for some reason you love living in spreadsheets, consider growth investing (and don’t follow literally any of my advice).

In many ways, the job of the writer and the job of a VC are quite similar, in that they both ask you to produce an original end product (in the writer’s case, articulated ideas and stories; in the investor’s case, a differentiated portfolio with outsized financial returns) without much of a map for how you get there. The reason professional writers complain about writing so much is that it’s really difficult to wrangle your brain into producing uniquely interesting thoughts all the time, and highly frustrating when you consider it your job to do so. Making good investment decisions is similar; just with the added element of also being highly social. Taking the quality of your self talk seriously seems superfluous but is an investment that will result in better decisions.

A lot of the game of investing is won by getting people to think of you — a sign that you’ve built the kind of moat we call a strong brand. Remember: a fund is just a pile of money with a person on top to sell it. As an investor, putting down stakes in the ground about what you invest in saves you a lot of time in the long run because it allows people to self-select for fit

I’ve been surprised by how much it’s benefited my fund to make Moth’s brand (i.e. what I invest in and look for) difficult to summarize in a sentence. For small early-stage generalist funds like my own, quality matters much more than quantity. Quality deals almost always come from trusted sources who resonate with my taste, not from a list of random companies for which I have no context.

A brand is a promise to show up in the same way time and time again. Good brands are built on being decent and principled with all of the people you interact with.

Lastly and of utmost importance: remember that fear of failure fades into the background if you focus on leaving everyone you encounter along the way better than you found them.

VCs need to believe that your company could be a billion-dollar business and generally lack imagination — you need to paint a vivid picture of this path for them, starting with the striking protagonist character you play in your company’s story.Your alter ego should never lie, but it should be completely comfortable showing the fullest expression of your ambition to people who probably intimidate you. Fundraising is a snap judgment game — most VCs are trying to pattern-match you to a founder archetype who already won. They index primarily on IQ, self-belief, experience, and personability (in that order). A general rule of thumb is that to be taken seriously in SV, male founders would benefit from acting warmer, while female founders are taken more seriously when they act colder. Both benefit from acting a little entitled.

a VC’s job is to make a diversified portfolio of bets — you are only one. Most founders find being around VCs distracting and draining because they feel pressure to perform the role of ‘impressive person.’ If you can’t immediately capture value from your performance… why waste your energy?

don’t expect the average investor to provide much value beyond money and connections. This makes the 10% of investors who can be legitimately useful to your business worth their weight in gold. Develop litmus tests to identify the valuable ones quickly and avoid wasting your time trying to convince nonbelievers.

our goal here is to spend as little time fundraising as possible — which requires being strategic about the order in which you talk to investors and how you talk about where things stand as you progress through the raise. The combined force of controlling those two variables are what “generates momentum” during your fundraise process.

Make a list of all the investors you know and can get introduced to, ordering them by the ones you most want on board to the ones you couldn’t care less aboutTalk first to a few low-stakes investors at the bottom of your list to practice your pitch and identify common investor questions and critiques you’re going to getIf available to you, next get a few investors who already wanted to give you money on board so you have a dollar amount you can say you’ve raisedWork your way up your investor list, talking to the investors you most-want-on-board-but-still-need-to-convince last (this optimizes your odds they say yes)

This all goes by much faster if you court investors similarly to how hot girls treat their many potential suitors. If your raise is already a little taken and you exude an air that you don’t need them, mimetically-minded investors become much more interested.

If you’re anything like me, you will worry intensely about not making a fool of yourself. It will probably go ok, but not as amazing or illuminating as you’d hoped. You might leave and feel a deep sense of lostness set in. This is all very normal. In time you will see them in increasing clarity, often noticing the differences between your and their values and why you would not enjoy living their life at all.

the people on pedestals probably hate being there. It’s lonely, hard to trust that the intentions of the new people around you are pure, and you often feel like you’re constantly letting people down. In the end, idolization hurts everyone involved.

Beware of intellectual dementors and clout demonsIntellectual dementors will try to eat your ideas and interestingness — not necessarily to copy you, but to wring your brain dry to amass knowledge themselves. They often play mini IQ games/tests of will in conversation and masquerade as investors while never actually investing. Clout demons are similar, but view people less as brains and more as stepping stones towards supreme social status. The power move to protect yourself from both is to simply abstain from playing their games — give as little info on yourself and your ideas as possible and reflect their questions directly back at them.

People will help you if you ask for what you want clearly and concisely

Knowing what you want requires a lot of upfront soul-searching, followed by strategic and long-term thinking once you’ve committed to a thing (I can’t really demystify this more). Once you’re all in, I highly recommend diligently keeping a list somewhere of the top three things you currently need help with so when people ask, you’re ready.

You don’t want to make people feel like you’re using them but you do want to use your social capital for things you care about. General rule of thumb: ask for things either 1) after a positive interaction or 2) completely out of the blue with a concisely written and compelling email/text. Tone matters because you don’t want to sound desperate and you do want to show you know how to play the game (write like the founder you most admire talks).

once we’ve taken action on behalf of something, our brain assigns more value to said thing. Tim Keller: “The feeling of love follows the action of love.” Love is a strong word here, but the point stands — help people help you. Startups are long-term games, so it only makes sense to do them with people you truly want to be around for a very long time.

Muse as a brand and a product represented something aspirational. People want to be deeper thinkers, to be more strategic, and to use cool, status-quo challenging software made by small passionate teams. These kinds of aspirations are easier to indulge in times of plenty. But once you're getting laid off from your high-paying tech job, or struggling to raise your next financing round, or scrambling to protect your kids' college fund from runaway inflation and uncertain markets... I guess you don't have time to be excited about cool demos on Twitter and thoughtful podcasts on product design.

I’d speculate that another factor is the half-life of cool new productivity software. Evernote, Slack, Notion, Roam, Craft, and many others seem to get pretty far on community excitement for their first few years. After that, I think you have to be left with software that serves a deep and hard-to-replace purpose in people’s lives. Muse got there for a few thousand people, but the economics of prosumer software means that just isn’t enough. You need tens of thousands, hundreds of thousands, to make the cost of development sustainable.

We envisioned Muse as the perfect combination of the freeform elements of a whiteboard, the structured text-heavy style of Notion or Google Docs, and the sense of place you get from a “virtual office” ala group chat. As a way to asynchronously trade ideas and inspiration, sketch out project ideas, and explore possibilities, the multiplayer Muse experience is, in my honest opinion, unparalleled for small creative teams working remotely.

But friction began almost immediately. The team lead or organizer was usually the one bringing Muse to the team, and they were already a fan of its approach. But the other team members are generally a little annoyed to have to learn any new tool, and Muse’s steeper learning curve only made that worse. Those team members would push the problem back to the team lead, treating them as customer support (rather than contacting us directly for help). The team lead often felt like too much of the burden of pushing Muse adoption was on their shoulders. This was in addition to the obvious product gaps, like: no support for the web or Windows; minimal or no integration with other key tools like Notion and Google Docs; and no permissions or support for multiple workspaces. Had we raised $10M back during the cash party of 2020–2021, we could have hired the 15+ person team that would have been necessary to build all of that. But with only seven people (we had added two more people to the team in 2021–2022), it just wasn’t feasible.

We neither focused on a particular vertical (academics, designers, authors...) or a narrow use case (PDF reading/annotation, collaborative whiteboarding, design sketching...). That meant we were always spread pretty thin in terms of feature development, and marketing was difficult even over and above the problem of explaining canvas software and digital thinking tools.

being general-purpose was in its blood from birth. Part of it was maker's hubris: don't we always dream of general-purpose tools that will be everything to everyone? And part of it was that it's truly the case that Muse excels at the ability to combine together so many different related knowledge tasks and media types into a single, minimal, powerful canvas. Not sure what I would do differently here, even with the benefit of hindsight.

Muse built a lot of its reputation on being principled, but we were maybe too cautious to do the mercenary things that help you succeed. A good example here is asking users for ratings; I felt like this was not to user benefit and distracting when the user is trying to use your app. Our App Store rating was on the low side (~3.9 stars) for most of our existence. When we finally added the standard prompt-for-rating dialog, it instantly shot up to ~4.7 stars. This was a small example of being too principled about doing good for the user, and not thinking about what would benefit our business.

Growing the team slowly was a delight. At several previous ventures, I've onboard people in the hiring-is-job-one environment of a growth startup. At Muse, we started with three founders and then hired roughly one person per year. This was absolutely fantastic for being able to really take our time to find the perfect person for the role, and then for that person to have tons of time to onboard and find their footing on the team before anyone new showed up. The resulting team was the best I've ever worked on, with minimal deadweight or emotional baggage.

ultimately your product does have to have some web presence. My biggest regret is not building a simple share-to-web function early on, which could have created some virality and a great deal of utility for users as well.

In terms of development speed, quality of the resulting product, hardware integration, and a million other things: native app development wins.

After decades working in product development, being on the marketing/brand/growth/storytelling side was a huge personal challenge for me. But I feel like I managed to grow into the role and find my own approach (podcasting, demo videos, etc) to create a beacon to attract potential customers to our product.

when it comes time for an individual or a team to sit down and sketch out the beginnings of a new business, a new book, a new piece of art—this almost never happens at a computer. Or if it does, it’s a cobbled-together collection of tools like Google Docs and Zoom which aren’t really made for this critical part of the creative lifecycle.

any given business will find a small number of highly-effective channels, and the rest don't matter. For Heroku, that was attending developer conferences and getting blog posts on Hacker News. For another business it might be YouTube influencer sponsorships and print ads in a niche magazine. So I set about systematically testing many channels.

While there were undoubtedly people who came in for the food, worked 3 hours a day, and enjoyed their early retirements, all the people I met were earnest, hard-working, and wanted to do great work. What beat them down were the gauntlet of reviews, the frequent re-orgs, the institutional scar tissue from past failures, and the complexity of doing even simple things on the world stage. Startups can afford to ignore many concerns, Googlers rarely can. What also got in the way were the people themselves - all the smart people who could argue against anything but not for something, all the leaders who lacked the courage to speak the uncomfortable truth, and all the people that were hired without a clear project to work on, but must still be retained through promotion-worthy made-up work.

Another blocker to progress that I saw up close was the imbalance of a top heavy team. A team with multiple successful co-founders and 10-20 year Google veterans might sound like a recipe for great things, but it’s also a recipe for gridlock. This structure might work if there are multiple areas to explore, clear goals, and strong autonomy to pursue those paths.

Good teams regularly pay down debt by cleaning things up on quieter days. Just as real is process debt. A review added because of a launch gone wrong. A new legal check to guard against possible litigation. A section added to a document template. Layers accumulate over the years until you end up unable to release a new feature for months after it's ready because it's stuck between reviews, with an unclear path out.

We still believe that there will be a separation between the “application layer” companies and foundation model providers, with model companies specializing in scale and research and application layer companies specializing in product and UI. In reality, that separation hasn’t cleanly happened yet. In fact, the most successful user-facing applications out of the gate have been vertically integrated.

We predicted that the best generative AI companies could generate a sustainable competitive advantage through a data flywheel: more usage → more data → better model → more usage. While this is still somewhat true, especially in domains with very specialized and hard-to-get data, the “data moats” are on shaky ground: the data that application companies generate does not create an insurmountable moat, and the next generations of foundation models may very well obliterate any data moats that startups generate. Rather, workflows and user networks seem to be creating more durable sources of competitive advantage.

Some of the best consumer companies have 60-65% DAU/MAU; WhatsApp’s is 85%. By contrast, generative AI apps have a median of 14% (with the notable exception of Character and the “AI companionship” category). This means that users are not finding enough value in Generative AI products to use them every day yet.

generative AI’s biggest problem is not finding use cases or demand or distribution, it is proving value. As our colleague David Cahn writes, “the $200B question is: What are you going to use all this infrastructure to do? How is it going to change people’s lives?”

Entrepreneurship is like one of those carnival games where you throw darts or something.Middle class kids can afford one throw. Most miss. A few hit the target and get a small prize. A very few hit the center bullseye and get a bigger prize. Rags to riches! The American Dream lives on.Rich kids can afford many throws. If they want to, they can try over and over and over again until they hit something and feel good about themselves. Some keep going until they hit the center bullseye, then they give speeches or write blog posts about "meritocracy" and the salutary effects of hard work.Poor kids aren't visiting the carnival. They're the ones working it.

Users rely on drug dealers for ecstasy and most other psychedelics, or in elite cases, they employ chemists. One prolific drug dealer in San Francisco who serves a slice of the tech world is known as “Costco” because users can buy bulk at a discount, according to people familiar with the business. “Cuddle puddles,” which feature groups of people embracing and showing platonic affection, have become standard fare.

I think when you're starting a company, it's really useful to ask the question, why now? And this is like, pretty cliche for startup stuff, so if you've heard of it already, apologies, but I do think it's a really useful framework. And that question of why now? Can be societal. Maybe there's some new cultural trend, perhaps it's regulatory. Some law has been passed or appealed. I like the technological version. And for us we saw drones in 2012 and WebGL as few technologies that were happening where because these technologies were happening, new possibilities were suddenly there.

But we're like, why would you do anything in photo editing if you're not on the phone? And so we felt like we were kind of building the wrong place and then eventually sort of shifted our attention to design, which I had been a design internet flipboard and that helped kind of help me realize what would be possible there.

And I would just say don't just go for an idea because it's kind of working. Go for an idea that you really care about because even if it doesn't work, you'll still learn from it and you'll still have one.

those most likely to become entrepreneurs are well-rounded. A 2005 study from Edward Lazear suggests that the self-employed tend to be generalists, not specialists.