Unfettered Thoughts From a Flailing Founder

B2B stands for “back to boring” and building a startup is not fun

ChatGPT 4 prompt: “Generate an image of a flailing tech founder, like a fish out of water. He’s losing energy and interest and he’ll eventually make peace with stopping. The scene should be calm, but subtly urgent. The image should be in the style of Jorge González Camarena.”

One year ago, I quit my job and started a company. The initial spark was like any other beginning for a software engineer in San Francisco. Join a team, pitch an idea, and take off at a startup accelerator. I had my fair share of ups and downs during the year, but this past month may have been the longest I’ve been out of water. When traction and success are not immediate, a founder may find themself thrashing and flailing, gasping for anything and anyone’s attention. This was certainly my experience over the last several weeks.

As I wind down my journey as a startup founder, I’m overcome with thoughts and reflections about what I’ve learned about myself, my goals and interests, and what I’ve discovered about the realities of building a company. In quick passing, most of what I have to say are whiny complaints—naturally, it may sound defensive and bitter. Over time, however, I hope this message reaches the right person, a founder or prospective founder who feels trapped or stuck like a fish out of water. I didn’t succeed this time around, but this isn’t the end of the book for me.

Here are my closing thoughts on this chapter.

B2B: Back 2 Boring 😴

I’ve never considered myself a “B2B founder”, but I found myself in a position, on a team, at a time and place where enterprise and AI were screaming for disruption. Who could ignore the opportunity to build LLMs into modern B2B software? It was obvious.

Discovering Air 💨

The tale of B2B is well documented. VCs encourage founders who are searching for a domain to seek out underserved markets. Talk to hundreds of prospective customers. And hopefully, find a problem painful enough that someone is willing to pay for it to go away. You’re unlikely to strike gold on your first try and that’s okay. Try again. And again. And again and again and again and again. The discovery process can be monotonous and grueling, but not in the form we typically imagine. Enough has been said about grit and a founder’s ability to persevere through turbulent times. But what about when there’s no turbulence? When there’s only air? Maybe founders should also be tested on their ability to withstand boredom.

The ideation and discovery process was immensely difficult for me. As a builder, all I wanted to do was build. It’s easy to lose focus if tech and tinkering occupy a large portion of your headspace. For a founder-builder, this is a balancing act on the tiniest of tightropes.

ChatGPT 4 prompt: “Generate an image of a tech founder who is balancing on a tightrope. On one side of the rope is a horde of customers and phones and chatter. On the other side of the rope is an abundance of new shiny technology. The founder is struggling to balance. The image should be in the style of Jorge González Camarena.”

Fake Empathy 🎭

There’s no doubt that historically underserved markets need new technology. It’s typical to start with a small problem in a narrow domain and expand. B2B founders excel at the process of cycling through ideas, sizing markets, and then executing on particular solutions. Exceptional founders succeed even outside their areas of expertise.

I suppose I’m not one of these exceptional founders. Working on someone else’s problem felt like a drag. As our team pivoted towards completely new domains, it was hard for me to build empathy for customers who simply didn’t share our experiences and values. At times, it felt no different from working a regular 9-to-5 job. Listen for problems, build solutions, pretend to care. Rinse and repeat. On the spectrum of missionary to mercenary, I definitely felt closer to the latter.

Capped Vision 🧢

Building a massive vision in a space where you can barely get your foot in the door is heroic. As founders, we’re told to pull our vision of the future into the present. Sadly, the reality of underserved markets is that most teams and problems aren’t ready for your exciting future. They’re simply stuck too far in the past without any rope to climb out with. This means that founders spend more time pushing the past uphill into the present. Practically, a founder’s vision can only be as big as the present allows.

YC recently shared their Requests for Startups, which includes a call for new ERP software. Upon further reflection, I’m becoming more convinced that this point is evading the larger problem for businesses in underserved markets. These markets need talent and motivation, much more than they need new software. This thought has crippled me to the point of discouragement. I laud those who are made for B2B.

Unfettered Thoughts From a CEO 🤨

No one said anything about fun. We try our best every day to put on a smile, but the truth is that in addition to being insanely hard, building a company can at times be downright miserable.

Not Fun, But Happy 🤔

I attended a talk with a prominent CEO of a large AI company and when asked about “fun” he snapped back his response at first. “I’m not having fun”. Laughter erupted from the audience. Then hesitation. Then repeat, “I’m not having fun”. He emphasized the point several times while claiming that he was still fulfilled and happy in other parts of his life. It was an honest and honorable response, but equally paradoxical.

At the very least, it made me ask myself, am I having fun? If the answer is not yes, then it is no. In my case, I may not have been happy either.

Operators Should Quit Sooner 🛑

Later, the CEO was asked about when founders should pivot. He suggested that founders usually pivot away from ideas too soon. He wished that we would think on longer time horizons for problems and ideas. Casually, he slipped in another viewpoint from the opposite: founders who are better operators should quit sooner. I had heard this comment before, but for whatever reason, this time felt like the final death blow. In the long arc of a career, a highly skilled operator may have orders of magnitude more impact than a typical founder. But of course, we always see the exception in ourselves, at least in the beginning.

At this moment, I recognize that I’m a much stronger operator than I am a founder. By a long shot. I’m at my peak starting from 1. This state may not always be the case and I suspect I’ll be motivated to try again in the future, but who would give me a chance given my track record? What about my grit? These are questions for later. For now, I have my eyes set on a new mission and I hope readers will understand that honesty with the self is paramount above all else.

Thank you to my co-founder Ayan for giving me the confidence to start this journey with him and thank you to the partners at South Park Commons for believing in us. Today is not my day and this chapter is over. But stay tuned. My book is still being written.

ChatGPT 4 prompt: “Generate an image of a tech founder who has made peace with his decision to walk away from it all. The image should be in the style of Jorge González Camarena.”