Jacob O'Bryant
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The trade-offs of being a startup founder
23 September 2020

I recently hit my 20-month mark as a startup founder, with half of that being spent on Findka. Over that time, I’ve become painfully aware of the downsides of such a career choice—and at least one of those downsides was quite unexpected. But let me give you some background first.

I chose to do a startup because I have lots of project ideas, and I wanted to work on them full-time. I wanted freedom to explore and build. During college, I thought seriously about going to grad school. However, grad school comes with an important constraint: your projects have to be research. This Paul Graham quote sums it up well:

I don't consider myself to be doing research on programming languages. I'm just designing one, in the same way that someone might design a building or a chair or a new typeface. I'm not trying to discover anything new. I just want to make a language that will be good to program in. In some ways, this assumption makes life a lot easier.

The difference between design and research seems to be a question of new versus good. Design doesn't have to be new, but it has to be good. Research doesn't have to be good, but it has to be new. I think these two paths converge at the top: the best design surpasses its predecessors by using new ideas, and the best research solves problems that are not only new, but actually worth solving. So ultimately we're aiming for the same destination, just approaching it from different directions.

My experience doing undergrad research taught me that I didn't want to have to frame my ideas as research problems. I think grad school might be a good option if the type of ideas you have naturally fit the mold of research—but that isn't the case for me.

So after getting my Bachelor's degree, I worked for a year and then became a full-time founder. After almost two years, I believe I'm finally converging on something that will work (thank you, thank you, please hold the applause). But my journey to get here has felt pretty suboptimal. And this brings us to my main discovery:

For many good ideas, the constraint to become a business can be just as damaging as the constraint to be research.

That seems obvious, yet I never thought about it much until recently. Perhaps that’s because the most commonly cited reason to not start a startup is roughly “it’s really hard and you probably won’t succeed.” If you’re ambitious, “it’s really hard” is a positive signal, in the same way that most people would judge a $80 pair of boots to be better than a $20 pair.

First, the business constraint can distract you from the most meaningful parts of your idea. This bit me hard when I was working on my previous startup, a music recommender system. My plan was to make an algorithm that was better at picking which songs to play than Spotify and Pandora (this was the focus of my undergrad research). But instead of working on the algorithm, most of my time was spent building music player prototypes (protip: never build an audio app on Android) and figuring out how to monetize (“Can I license music myself? If I just use Spotify’s API, will anyone pay for my app on top of a Spotify subscription? Could I get started with only users who still download their music?”). In hindsight, most of my effort feels wasted.

Second, you might ignore interesting ideas that come to you if they don’t seem to be related to your startup. Biff, a web framework I made, only exists because I was being indulgent. I decided to spend a day per week writing Clojure web dev tutorials, not realizing that this would eventually lead me to migrate Findka to my own self-hosted Firebase alternative. I’ve had a handful of other interesting thoughts which I would like to explore but haven’t, since they aren’t related to Findka. But who knows where those ideas would go?

Another example: if Linus Torvalds had been obsessed with starting a business, would we have Linux?

Framing your ideas as businesses can also dampen your morale. The euphoria of quitting my job and being free to work on my own projects lasted for about two months. After that, it was largely replaced by the soul-crushing burden of how-on-earth-will-I-ever-make-a-living-from-this. Psychologically, I sometimes wonder if it’d be easier to build a business if I wasn’t trying to build a business.

These won’t be problems for everyone. I think they’ve been problems for me because of the types of ideas I’m naturally drawn to. I tend to have “grand visions.” For example, Findka: it’s meant to be a dead-simple, general-purpose information discovery tool, kind of like Google. But Google is only good for search—when you’re looking for something specific. What if you just want to be made aware of new information that’s relevant to you, whatever that information might be? Why isn’t there one big recommender system for everything?

My ideas feel like business ideas because I can totally see how they would make lots of money—eventually. But the problem with these grand visions is that they don’t tell you how to get the idea started, and that’s what matters in a startup. I’ve been working on Findka for 10 months and I’m only now getting to something that’s worth using in the short-term (i.e. before we have lots of users and data to make the algorithm great). Anecdotally, it seems to me that most successful startups are not driven by grand visions at first; rather, the long-term vision comes into view after the company starts to grow.

I wouldn’t be surprised if grand visions are on average more of a liability than an asset for early-stage founders. If that’s the case, it’s ironic that startups, with their change-the-world potential, naturally appeal to grand-vision people like me. Perhaps we’d be better off working through things first in a low-pressure, non-startup phase, switching to startup mode when (and only when) an infant grand vision matures into a real business idea.

I for one would've probably been much better off if my post-quitting-job plan had been more like what Rich Hickey did:

I started working on Clojure in 2005, during a sabbatical I funded out of retirement savings. The purpose of the sabbatical was to give myself the opportunity to work on whatever I found interesting, without regard to outcome, commercial viability or the opinions of others.

After a period of pure exploration, I could've picked whatever “exit strategy" fit best:

Had I done that, I bet I would’ve learned and produced a lot more over the past 20 months. And if I decide later that another pivot is in order, I’ll probably pivot to being a consultant instead of pursuing another startup idea. Then I can spend my (hopefully abundant) free time exploring whatever I like, without business constraints.

However, I can't help but wonder: wouldn’t the world be better off if more people had the freedom to explore? From an individual’s viewpoint, the best bet is probably freelancing or saving up for an unpaid sabbatical. From society’s perspective, we could do a lot better.

Universal basic income might solve this problem, but there’s potentially another answer: part-time jobs. It’d be great if there were more opportunities to work just enough to pay your living expenses and save for retirement, and then spend the rest of your time exploring. And if the supply of well paid part-time jobs went up, there would be more opportunities for explorers to connect with each other. You could make a social network where people list their projects and interests on their profiles, and you can browse people by topic. You could find people to discuss ideas with, and you could find people to work with.

The networking would also reduce the risk: even if your exploration doesn’t result in anything significant, you’ll have a network of people who know you do good work. That’s incredibly valuable—if this whole system worked well enough, it could be a good alternative to college. Who needs a degree when you have referrals?

So, the big question is simply “how do you make well paid part-time labor highly available?”

One option: established companies could create teams of part-time workers who do their own projects in their free time (perhaps call it R&D). Most of the projects won’t benefit the business, but some will, given a large enough sample size. A side effect of working part-time on the business is that the workers will be more likely to have business-related ideas. For the right company, it might end up net-positive.

For example: Stripe would be a great company to try this out. Their business is good at capturing spillover benefits from other companies, hence e.g. Stripe Atlas. So even if these R&D projects don’t benefit Stripe directly, they could still be profitable indirectly.

Another angle might be startup investment. If you got a bunch of explorers together and helped them find part-time work and network with each other, it would probably result in some good startups, and you could provide seed funding. Though I’m guessing that this strategy would be harder to pull off profitably than the established-company strategy.

Finally, there’s always the grassroots approach: there could be a social network for explorers like I mentioned above, and then individuals can deal with the financial problem on their own. As the network grows and members build relationships, they should be able to help each other find freelancing or other part-time work.

If we’re lucky, this could turn into the next big hub for creative thinkers. We should call it “The Explorers’ Guild.”

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