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.

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.