Founder Fumbles

Preface

Hi. I’m Clarice. I started writing Founder Fumbles because I couldn’t stop thinking about the things I wish I had done differently in my startup experiences so far. For nearly two years, I was part of a startup that received significant support: a university that gave us space and time, generous sponsorship from a global foundation, and even a summer incubator in Japan. But we still struggled. Not just with product-market fit or strategy, but with decision-making, confidence, clarity, and conflict. At the time, I wasn’t always sure what was going wrong. Later, as I began thinking back on the experience, sometimes just to process it, I realized that I had been making sense of our journey in fragments. Eventually, those fragments became essays. These aren’t polished answers or universal truths. They’re reflections: raw, specific, and sometimes messy. I’ve tried to be honest about what we got wrong, what I misunderstood, and what I’d do differently now. I’ve also tried to be clear about what I don’t know. This is not advice from someone who built a unicorn. It’s a window into the inner workings of a startup that didn’t work out. Startup failure is rarely the result of just one thing. It’s often a swirl of overlapping mistakes, missed cues, personal limits, and bad timing. What I’ve tried to do is pick apart the pieces, not to overanalyze, but to understand. Writing these essays helped me make sense of what happened. I hope reading them helps you, too.

Preface

Introduction

This series, Founder Fumbles, is my attempt to counteract survivorship bias. Founders are usually inclined to read success stories and stick to them. The issue with this is that even successful founders make mistakes and still become successful. What is detrimental for one startup isn’t always detrimental for another. I think it’s useful to take a closer look at the mistakes of a startup that did not succeed and also to examine what we did right that still didn’t result in overall success.

I'm originally from Trinidad and Tobago, West Indies. In high school, I focused on STEM, but at Minerva University, I switched to business and entrepreneurship. My university is pretty unique, with the opportunity to spend each semester in a different country. For the past four years, I haven’t lived in one location for more than four months at a time. This lifestyle has its challenges, but I love the digital nomad style of life.

My first startup experience was a university program called the AI Lab. It was supported by the Masason Foundation, a Japanese nonprofit dedicated to developing young people with high aspirations and exceptional talents. In Fall 2022, we began with four cofounders, which then became three by the end of Spring 2023. In the Summer of 2023, the three of us went to the Masason Foundation incubator in Japan, where we didn’t have any competing obligations, allowing us to focus on the startup full-time. Then, from the Fall of 2023 to the Spring of 2024, we continued working on the startup part-time since our semester at university had resumed. I briefly had another startup experience with a different set of cofounders from Spring 2024 to Summer 2024. Subsequently, I engaged in business development with a solar technology company that was trying to transition from a service-based business to a product-based business: a more startup-type deal.

These essays discuss my experiences and reflections through several relevant topics, including the impact of cognitive biases, imposter syndrome, how scientific literacy helps founders, and much more. My reflections led me to do a deep dive into research that supports my conclusions. I provide some advice, my message being something like, “These are things I would have done differently, given my particular set of circumstances.” The idea is that if any of these situations seem familiar to readers, they can find something here worth trying.

I think a big limitation of these reflections is that I had major, undiagnosed mental health problems for most of the time I was in my first startup. I was not willing to incorporate the details of that into these essays, and even if I was, I’m not sure how to fully explain how the impact on the company. But at the very least, I can say that certain executive functions were extremely difficult for me. And that’s the kind of thing that affects just about every part of a startup.

Another limitation is the medium with which I am that these blog pieces may make it sound as if these anecdotes I mention happened in a vacuum, but maybe that’s just the nature of the blog format. It can be difficult to capture the complexity of a story where there are so many overlapping variables. It’s convenient to wrap things up with a neat beginning, conflict, and resolution—even when real life doesn’t work that way. That might make some of these stories easier to read, but it doesn’t mean they were clean or simple or linear as they were happening. Necessarily, these essays contain oversimplifications.

I also acknowledge that these pieces are a bit of a longer read. There’s a good argument for making them shorter. I know founders famously prefer to read concise content, like Blinkist, bite-sized advice, or tweet threads, but this is not appropriate for several reasons. Being so young in my career, for readers to take me seriously, I need to explicitly elaborate on my evidence to be taken seriously. More importantly, these pieces are about illustrating that things are not always what they seem. That means I have to show how things appeared, how I figured out they weren’t, and how I coped.

The topics I chose may seem a bit random, but they are perhaps where my most valuable learnings have emerged.. There are other mistakes worth discussing, like the myth that you need to give up every other professional pursuit to make a startup work or how founders navigate work-life balance. These are real issues. I just don’t have the clarity to articulate them at the time of this writing.

I don’t know if these reflections will be useful to everyone, but they helped me make sense of a very messy, very confusing time. If you find yourself in the middle of that same fog, my sincere hope is that something here will help you move forward with a little more clarity.