Fantastic Builders and Where to Find Them, 2nd Installment

Read the 1st installment for an introduction to the series + builder spotlights #1 and 2.

Builder spotlight #3: The Right Kind of “Crazy” (Esther Crawford)

Image source: https://x.com/esthercrawford/photo

Principles on display: self-honesty as the foundation for self-trust; agency is what makes us human; your life as the measure

I’d been wanting to sit down with Esther Crawford ever since I saw her legendary tweet about the time when she went against conventional wisdom and put her own savings into her startup.

My first encounter with this tweet was through Paul Graham’s quote tweet commenting on it:

For my part, I thought Esther’s story sounded like a great example of a builder’s willingness to bet on her independent judgment. But I also wondered what it was about Esther’s context at the time that would have warranted such a judgment—since it would in fact have been a foolish move in many similar circumstances. Did she have a backup source of financial support in case the company failed? Was she seeing early signs of traction that were clear from her customer conversations but hard to communicate to investors? Or was it in fact a foolish decision that simply looks good in retrospect due to survival bias?

I asked Esther these questions over bagels last week, and her answers impressed and inspired me beyond anything I could’ve hoped for. Here’s some of the additional context Esther shared about her story:

Despite being a single mom with 2 young kids at the time, she did not feel especially threatened by the prospect of burning through her savings; she knew that in the worst case scenario, she could simply get a job. In fact, she had done the same thing once before for a prior startup she’d also cofounded, and that time she did lose the money—and it was fine. It probably helped that she’d grown up quite poor and had managed to stay resilient through all sorts of family drama, from being kept secret by her biological father until age 7, to finding out her stepfather was sentenced to life imprisonment when she was 13. So the prospect of needing to watch her spending for a while did not exactly intimidate her.

This was by no means the first time Esther had made an unconventional decision that worked out well for her in the long-run. Here were a few others:

• As a 21-year-old college student trying to lose a bunch of weight, Esther was dealing with a lot of shame about her body and yet knew she needed accountability. So she joined the predominantly much older crowd of people using Weight Watchers at the time, and started posting videos about her weekly progress on this small and esoteric (and thus, she figured, relatively anonymous) new video platform called YouTube. Her videos started gaining popularity with increasing numbers of viewers who found them inspiring, and eventually caught the attention of both the YouTube and Weight Watchers CEOs, who recruited her to help them promote their respective businesses in this new age of online video content.

• As a graduate student studying International Relations and looking for new ways to explore her interests in online media and film, Esther looked on Craigslist and found a receptionist job at a film production company. She figured this would be a good way to get her foot in the door and learn more about the industry—and she couldn’t have been more right. The skills and contacts she picked up at that company became the launchpad for what essentially became her first startup.

• As a 29-year-old with 2 kids and a husband of 10 years, Esther realized her professional ambitions required her to move to San Francisco. So she said to her husband, “I am moving to SF with the kids, and you can either join us or not.” He did join them, however reluctantly, and they amicably divorced sometime later.

• Today Esther and her ex-husband are both remarried and their 2 families are great friends, facilitated by the fact that Esther bought them both homes across the street from one another many years ago—another unconventional decision that has worked out beautifully for all parties, thanks to the years of earned trust and understanding between them.

Some months after Esther’s decision to put her own savings into the startup, she finally managed to raise a round of venture capital, only to realize a few months later that the product they were building—which involved, prophetically enough, interactive AI personae—was about 5-6 years ahead of its time. (She was right; this was 2017.) So she made the hardest professional decision she had ever made up to that point, and told one of her lead investors that the product they had just invested in was not going to work.

The investor was flustered by the news at first; then, after 3 hours of open, honest conversation, that investor looked at Esther and said, in effect: “look, I invested in you, and I believe in you now as much as ever. Whatever it is you decide to build, I will gladly back it, and will give you more money the next time you raise.” 

Esther spoke of this conversation, more than the initial decision to risk her own savings, as a critical inflection point: she had chosen to be completely honest with herself and her investors about a judgment that pained her to form, and the result was greater rather than lesser trust, both from herself and them. From that day on, Esther said, she never had any difficulty fundraising for her startups or making unconventional but values-aligned decisions for her own life and career. Her judgment had been tested in crucible after crucible, and it had stood the test of experience and time. 

After Esther told me this story, I expressed how much I admired the courage and independence of judgment she’s shown at so many junctures in her life. She mused that perhaps she had been driven by a need to “prove herself” to the people who rejected and dismissed her early in life; but I submit that such an interpretation wouldn’t do her credit.

A need to “prove oneself” to internalized authority figures leads to things like climbing conventional status ladders, or staying in an unhappy marriage, or piling up as much money as possible to preserve the appearance of having “made it”.

What motivated Esther to do things like take a receptionist job at a film company, pick up her life and move to San Francisco, and risk her savings on her startup was something far more personal and idiosyncratic: a conception of the interests she wanted to explore, the people she wanted to meet, the products she wanted to create, the life she envisioned and wanted to build for herself—and, yes, the proof that she really could count on herself to do it.