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.