I’m soon coming up on 6 months of unemployment. Half a year of trying to be an entrepreneur full-time.

I still haven’t made it, unfortunately. I have however learnt a ton. This post is a reflection on my entrepreneurial journey thus far and a discussion of how I formed my entrepreneurial meta-strategy.

Learning how to entrepreneur

Before starting my entrepreneurial journey, I figured there were more or less correct ways of doing things.

I figured that while I didn’t have a clue as to what I was going to work on, there were guidelines or rules I could follow that would optimize my chance at creating an economically sustainable business. The problem was I didn’t know what they were.

So, in parallel with building, I decided to start learning how to be an entrepreneur.

I tried a few different things, separate from the actual day-to-day trial and error of trying to build products, in order to learn the key lessons I’d need. Here are the ones I perceive to have worked, in ascending order of utility:

  • Reading as much random online material as possible on how to entrepreneur – think immersion learning on /r/startups (if it works for an LLM why wouldn’t it for me?)
  • Going through YCombinator’s Startup School
  • Speaking to various types of people in the space (VC’s, angels, entrepreneurs in the struggle, post-exit entrepreneurs)
  • Discussions with my co-founder/business partner

Consuming online material was moderately useful. The sheer volume of thought out there means there’s probably more useful information on places like Reddit/medium/substack than I’d be able to ingest from any other source, the only problem is finding it amongst all the slop. Still, passively browsing allowed me to gain a fuzzy sense of the key questions I wanted to answer, and informed future research.

YCombinator’s Startup School is a treasure trove of information. It is a curated set of videos and articles touching on a bunch of topics an aspiring entrepreneur needs to learn about. You’ll hear the lingo, and familiarize yourself with the basic structure of starting a startup.

Speaking to people in the space is likely the highest utility thing I did per minute spent. A possible exception to this is investor chats. Some VCs were tremendously insightful. With others it felt more like I was a way for them to gauge the market/competition so they could pass this information on to companies in their portfolio. Knowing the difference upfront likely takes a bunch of knowledge I don’t have, and if you’re not actively raising I believe saying no to intro chats is the best thing you can do overall.

My chats with angels were generally positive, though again, I think being selective upfront is EV+.

The real absolute must do for any entrepreneur is to speak to other entrepreneurs. Time and again I’ve been blown away by how generous more established entrepreneurs have been with their time, and getting to steal their hard-won knowledge by just asking the right questions is literally a cheat code. An added benefit is if there’s synergy in your businesses, or if one of you can put the other in touch with someone/something the other needs. The culture of paying it forward has been overwhelming and inspiring, and definitely something I hope to contribute to one day.

All of the learnings gleaned through the above mentioned methods have been internalized through discussions with my co-founder. Having someone go through the same thing as you at the same time who you can explore ideas and thoughts with as you come into contact with them is tremendously useful. I see it not really as an additive source of information, but as a multiplier. It upgrades the learning you extract from passive to active.

The entrepreneurial method

My goal while ingesting all this information was to arrive at a representation of a meta-method of entrepreneurship. An entrepreneurial method analogous to the scientific method.

While I don’t think I’m there, I do think I’ve made some progress.

Nothing else matters

Like the goal in the scientific method is singularly to increase or decrease confidence in an experimental hypothesis, the goal of the entrepreneurial method is singularly to find a way to generate utility for other people. That’s it. “Make something people want”. That’s what product market fit (PMF) is.

The great thing is I’ve heard repeatedly, through conversations with founders who have found PMF, that once you have it, the response from your customers will be unmistakeable.

While I can’t yet speak at all to how one should efficiently and sustainably continue to generate utility post-PMF, I believe that falls into the domain of scaling and running a business, I do think the process of searching for PMF is clearer in my mind than it was before.

Let go of your biases

You surely have biases and preconceptions regarding what problems your imagined customers have. They’re useful to the extent that they allow you to formulate an idea of what problem to solve, but may incur a cost if held on to post expiration.

Your opinion about a problem space needs to be directly grounded in customer insights. To me, there seem to be a few ways of validating these customer insights.

You can speak to potential customers. Do they confirm your problem verbally through open-ended conversation (no leading questions)? Do they tell you about a different but related problem?

You can manually solve your potential customers problem. Say that you have an hypothesis that there’s room for software helping American expats in the EU file expat taxes. A good way to validate this is to find a bunch of Americans and charge them for your work of filing their taxes. How hard was it to find Americans willing to pay you? How automatable was the work you did?

You can build out a minimal viable product (MVP) that solves your hypothesized problem. Do you find your customers use your product when you tell them about it? Why/why not? Does another group use your product?

These methods obviously have different strengths and weaknesses. Speaking to customers is cheap in terms of up-front effort, but your results may vary depending on how honest they are, and how well they fit the customer profile. Also, they have no reason to speak to you – you haven’t solved a problem of theirs yet.

On the other end of the spectrum, building out a full-fledged MVP takes a lot of engineering effort. However, if you get real traction in terms of usage metrics, you know you’ve got something. You can also collect feedback at a different scale than if you were to speak to every one of your users individually.

Likely, you shouldn’t be doing one or the other, but all of them synergistically.

I’ve found that building a demo is a useful way to get initial conversations. It’s proof of work. It shows you’re willing and capable of solving problems in your chosen space.

Similarly, you likely shouldn’t jump into building an MVP purely based off a hunch. Have a few conversations at first if you can.

Action drives everything

You need to take action. It is too easy to speculate about potential problems, analyze market opportunities, be put off by how far ahead a potential competitor is, or think about cool new technologies. Likely all you’re doing is generating new biases.

This is orthogonal to what you need to be doing.

You are a shark. You need to keep swimming.

Extending the scientific method analogy – the role of a researcher is to constantly propose experimental hypotheses, attempt to isolate the effect of an experimental variable, and using this, increase or decrease confidence in an explanatory model of the world, and if necessary propose amendments to this model.

You need to be doing the same thing.

You need to constantly be proposing novel problems you think people face, finding ways to validate whether they’re real problems or not, and attempting to solve them for other people. If you can solve a real problem for one person, it’s likely a real problem for another person.

If it’s a real problem for two people, automate your solution. Voila, you’ve now generated utility for a large group of people.

The flipside of this is that most of the time, most research is largely not novel.

Most research affirms something we already thought we knew (useful because it allows us to convert a bias into knowledge), reproduces previous novel findings, or disproves a new potential insight.

Very rarely are we able to make genuine leaps forward.

I think it’s likely the same for startup ideas. Most of the time, you’re going to be wrong. It is really difficult to think of a new problem, or a new way of tackling an existing one.

Time and time again I’ve been struck by the fractal like nature of the technological landscape. You start with a view of a problem space, an idea of the players and their relationships. You zoom in to a space that looks promising, only to find a similar amount of existing players and complexities in the subspace you thought were in the original space. Repeat ad nauseam.

Really, it’s a testament to human ingenuity.

The good thing is, you only need to find one real problem.

So stay lean. Keep your team small enough to be aligned on problem discovery and validation. Minimize distractions. Take failures in stride. Make finding PMF using an evidence based approach your singular aim.

A note on distractions

I do think it’s easy to distract yourself with work that doesn’t really move the needle.

Some of this is work that appeals to your vanity. I’m more and more convinced that creating pitch decks, booking meetings with VCs, and “building in public” are more often than not examples of this.

I’m not categorically against raising. I am however saying that if you can afford to bootstrap, and you don’t have PMF, what are you going to do with more money anyways? Hiring more people isn’t going to help you find PMF quicker. I think if you raise, you should have an excellent idea of what that money is going to help you accomplish.

A counterpoint to this is amortizing risk – pursuing a startup is likely the riskiest thing you can do. Sharing some of that risk at the expense of potential future upside may not be a bad idea.

However, in general, I think too many people default to “raise as much money as possible” too early. If you have a strong profile, or a silver tongue (or both), you can likely convince someone to back you financially. This may feel good, and like you’re closer to your goal, but I suspect it’s a common anti-pattern.

I also think building out a technically wonderful solution is an example of this. This is something I’ve had to learn the hard way.

Nobody cares how maintainable or scalable your MVP is. If it takes 2 extra weeks to build, that’s 2 weeks you’re not using to validate a problem. Most likely, you’re going to end up throwing away what you built in a few weeks anyways, and you probably won’t get more than 2 concurrent requests per second for a while. If you’re not optimizing for ship velocity, you’re probably doing it wrong.

Your single focus pre-PMF should be building the absolutely minimally viable prototype needed to validate a problem. Post PMF, I can see it being a different story (at least the perfectionist in me hopes it is).

Should I stay or should I go

On another note.

When do you stop pursuing a given problem space?

What is a recoverable setback vs an insurmountable one?

I suspect, “making it” in any industry is going to be difficult. You’re going to have to overcome problems with anything you choose to work on. Finding PMF will always be hard.

When does pivoting stop falling into the “iterating quickly” bucket, and start falling into the “lacks the grit necessary to succeed” bucket?

This is, in my opinion, one of the key fuzzy questions to learn how to answer in order to be a good entrepreneur. I don’t think there’s ever a clear right or wrong here, and likely you get better at this with wisdom and experience. Being good at this is probably where part of the “X-factor” of successful serial entrepreneurs comes from, just like having good “research taste” informing which problems you explore sets the great scientists apart from the good.