Lost and Founder

I usually listen to audiobooks while running. I have been an Audible member since 2010, and in the beginning, following a whole book through audio alone took some effort. It is much easier now. I did not notice the improvement happening from one book to the next, but looking back over the years, the difference is clear. Running and listening have become a comfortable part of the same routine. The book I most recently finished was Rand Fishkin's Lost and Founder.

I came across it in a post on Threads (I no longer remember which one). It sounded like a candid account of starting and running a company, which appealed to me partly because I have been feeling uncomfortable with some of the enthusiasm around startups lately. Yes, startups are hot again. They have always attracted attention (especially in this Bay Area), but the recent AI hype seems to have intensified it. However, recently, I keep encountering people who seem to want to become founders before they have much sense of what they want to build or why. The title of "founder" itself appears to be the goal, with a company as the means of acquiring it.

There are many reasons to start a business, and wanting financial success is a reasonable one. Still, I have seen cases where the company seemed to exist mainly to satisfy the founder's ego. That is difficult for me to feel enthusiastic about. I want to understand what someone cares about enough to spend years working on it, and what they believe should exist that does not exist yet. When just "becoming a founder" takes priority over those questions, I wonder what will sustain the work once the initial excitement wears off.

I went into Lost and Founder expecting something closer to Ben Horowitz's The Hard Thing About Hard Things, with its accounts of agonizing decisions under extreme pressure. Fishkin's story felt less extreme. He writes about building Moz, the SEO software company, and the experience is full of decisions, mistakes, and consequences that feel recognizable: choosing how to grow, working with investors, building products, and learning what running a company asks of you. Even when the consequences are painful, the story has an ordinariness that I found meaningful.

That ordinariness is a large part of the book's value. Of course, "ordinary" needs some qualification here. Fishkin is a comparatively fortunate founder in my view. He built a substantial business, which is already an outcome many founders would be glad to reach. His story still contains years of uncertainty and compromises, and success does not neatly resolve them. I would hesitate to call Moz an average startup, but the experience he describes feels closer to what someone should prepare for than the biographies of founders who built the greatest technology companies. It gives some shape to the years of work that can continue even when things go reasonably well. By the time you look back, those years may have taken up a substantial part of your life without making you a tech billionaire.

I suspect this also makes the book less immediately appealing to readers looking for a spectacular startup story or a recipe for success. A huge triumph is exciting to imagine, and an account of overcoming an extraordinary crisis can be compelling to read about. A founder explaining the limitations of a business or ordinary successes offers less of that drama. But if someone is considering starting a company, those limitations deserve attention. Several of Fishkin's points matched things I have thought for a long time.

One is his warning that even founding a startup in the top five percent may not make you rich. A successful company and a wealthy founder are different outcomes, and the distance between them can be considerable. The scale of the business, the ownership you retain, and whether that ownership can ever become money you can use all matter. I think people need to assess their expectations against the kind of success they are actually pursuing. A business can serve customers well, employ good people, and be a considerable achievement, yet still fall short of the wealth you imagined. Be clear about the outcome you want, and ask whether the work you are doing can realistically get you there.

Another is his caution about pivots. A pivot can be an effective response to something you have learned. Customers may need a different product from the one you imagined, or your original approach may turn out to be impractical. But I get uneasy when a company changes direction repeatedly without being able to explain what connects those decisions. Sometimes that looks like a lack of core purpose, especially when pivoting is treated as a clever move in itself. I do not mean that founders should cling to their first idea. I mean that they should understand the core value they want to create, and a pivot should bring them closer to delivering it.

The discussion of minimum viable products also stayed with me. Fishkin argues for an exceptional viable product, particularly when customers already have expectations of the company releasing it. In his book The Lean Startup, Eric Ries presents an MVP as a way to learn quickly from customers before making a larger investment. That is useful. What I have seen too often, though, is founders treating the MVP as the actual finished offering, then pouring marketing money into it before establishing whether it gives people a reason to use it.

The word "viable" carries a responsibility that can disappear in the rush to launch. A product being available says very little about whether it matters to anyone. It can be small and limited in scope while still doing something useful enough that a person wants to return to it. That is the standard I take from Fishkin's argument. There is room for rough edges and early experiments, but at some point the work has to make some meaning for the user. Spending more to attract people does not answer the question of why they should stay. Once customers have been disappointed, persuading them to give the product another chance can be extremely difficult and expensive.

I would recommend that anyone thinking seriously about founding a startup read both The Hard Thing About Hard Things and Lost and Founder. Horowitz gives a sense of how severe the pressure can become. If you start a company, you should expect to face some of that pressure yourself and be prepared to work through it. Fishkin helps set expectations for the long stretches of less dramatic work, and for success that may look different from what you imagined. For someone drawn to becoming a founder, that second perspective may be particularly useful.