4 weeks, 3 cofounders, and 15 interviews on mental health

On pivoting, being picky, not settling, therapy, and the fear of being forever alone

People outside of Entrepreneur First have trouble understanding that pairing up with a co-founder at EF…doesn’t actually mean very much.

We’re encouraged to form teams as soon as we feel like we might want to work with someone, and encouraged to break that team up as soon as we feel like it’s not working.

In my case, my shortest co-founder “relationship” lasted 72 hours. The fit looked great on paper, and we were very productive in terms of booking customer discovery interviews, but it became super clear that…we just didn’t like each other very much. And that won’t stand for 5-10 years, if not forever. If I just wanted to be productive with someone, any of us could, quite frankly, just pick up a job and be paid 5x more.

The justification for this is not that we’re all commitment-averse assholes who are constantly optionality-chasing; anybody who has ever lived in New York City post-graduation knows that this is a shitty way to live. The very real justification is that the opportunity cost of being in the wrong team and building the wrong company is enormous. It’s more a matter of valuing your own potential than it is about running away from commitment. Though of course, it’s very easy to use the “co-founder hookup” culture of the program as an excuse for never working through your own deep attachment issues.

So what have I worked through and where have I landed in four weeks? Here’s a whirlwind tour:

I started off with mental health, and specifically, the problem that I wanted to fix was matching between smart, high-performing people and smart, high-performing therapists. Think a hush-hush, invite-only, verified community of high achievers and heavy-hitting therapists, similar to Luxy for therapist matching. Luxy is a gate-kept dating app for wealthy, successful people only; the website is somewhat lacking in class and reads a bit like a dumping ground for sociopaths and narcissists. But I also know people who unironically use this app in real life and are genuinely grateful to no longer be wasting time on people who simply don’t match them in terms of ambition, financial means, and values.

Here are some deep truths that I’ve discovered through about 15 interviews with therapists and therapy seekers of all stripes, skewed towards the high-achieving end because of where EF’s personal networks tend to lie:

• A therapeutic relationship predicated on trust and respect is necessary for any progress to be made.

• A person with high intellectual horsepower cannot be vulnerable in front of a therapist who is not smart enough to understand what they are saying.

  • One of the most emotionally damaging things in the world is to express yourself fully and then to feel unseen. This is how it feels to try and explain your feelings to someone who does not understand you.

  • On the flip side, one of the most powerful aspects of therapy is giving someone the knowledge, perhaps for the first time in their life, that it is possible to fully express their emotions in front of someone and have it be seen and heard without judgement. Just knowing that this is possible tends to flip something very positive in the brain.

• High-achieving clients don’t just want an empathetic ear and emotional presence: those are necessary but not sufficient conditions. They want a productive path to fixing the problem, not a friend.

• Stigma is the single biggest force holding us back from real progress in mental health.

  • On the therapist side, stigma prevents people from allocating the necessary time, money, energy, and legitimacy into the idea of seeking help. Genuinely effective therapy is one of the most challenging forms of emotional labour in the world; it simply doesn’t make sense to expect therapists to excel at it unless they are also well compensated on the dimensions of money, prestige, etc. We should think about rockstar therapists (i.e. Brené Brown, Esther Perel, Jordan B. Peterson) the same way that we think about football players, supermodels, or famous actors. People post openly about their CrossFit routine or their expensive Peloton bike; there are entire Instagram accounts dedicated to workout videos, vitamins, nutrition, etc. Imagine a world where everyone talks as openly about mental health as they about about physical health. Imagine changing the narrative from “successful people don’t need therapy” to “successful people are very good at therapy”.

  • On the client side, stigma prevents people from reaching out in the first place, from disclosing to their friends, and from forming communities around mental health issues. (Alcoholics Anonymous stands as an impressive and effective exception to this rule, and there’s no reason why the concept shouldn’t be extended to all forms of psychological suffering). It means we all post bullshit on LinkedIn and Instagram about how happy and awesome and successful our lives are, contributing to someone else’s false belief that everybody is crushing it except them. Stigma creates a shitty Nash equilibrium for us all, except for perhaps genuinely well adjusted people. Given that trauma begets trauma, and most of our parents had something wrong with them, there simply aren’t that many of such individuals around.

I was speaking to a family friend who does alot of tech and angel investing; her feedback is that the mental health space is very crowded. I say this is a good sign for anyone who wants to innovate in the space; despite a million cuts at the problem, we still haven’t solved it. Not even close. People who seem to have it all - money, looks, fame, power, success - still kill themselves. People risk it all to defend the paths to agency and power that they know. People watch their parents’ livelihoods destroyed and spend the rest of their life waging institutional, cultural, and intellectual war against the thing that destroyed it. I’m not being facetious at all when I say that all of the world’s problems are caused by scared and hurt children who are still defending themselves with whatever mechanism they’ve learned how.

So I say, it’s a good thing that the space is crowded. It means we’ve tried a million things and there is still more to be done. Human trauma comes in infinite forms, because human lives come in infinite forms. If you’re doing some kind of building in the mental health space, whether it’s:

• A solo therapist in private practice, doing an hour at a time of high quality work;

• A professor or supervisor training the next generation of therapists;

• A life coach offering your unique perspective on Instagram and TikTok;

• An engineer working on the next Headspace, Insight Timer, etc etc…

Know that mental health is unique as a field because here, “industry experience” and “competition” doesn’t mean very much. I’ve had incredible therapists who were barely in the first year of their masters; I’ve been let down by therapists with PhDs from Oxford and decades of experience with Olympic athletes and federal prisoners. Insight and wisdom are not correlated with badges of prestige; the brilliant insider trading strategy of, say, McKinsey partner Puneet Dikshit, who risked it all for an extra $450k (did he need another yacht?) is surefire evidence of this.

So if you’re building in the mental health space - people will poo-poo you. As long as you really mean it, and you feel it deep from the heart, I say - ignore them.

The world is in pain, and it desperately needs your best shot at the problem.

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Book Review

I’m going to test out a section of this newsletter where I make book recommendations that have informed the article, with a few short notes on each.

I will never make a book recommendation unless I’ve actually read the book and feel prepared to engage in a deep conversation about it with anyone who cares to.

No affiliate links or bullshit - not now, not ever. Go ahead and buy one of these books if you care to - they are all excellent.

Since we’re on mental health, here are some of the most profound and helpful books that I have read on the topic:

Depression / Suicide: The Noonday Demon: An Atlas of Depression by Andrew Solomon

I found this book very comforting in a period of feeling down because unlike self help books (or well-intentioned friends), it doesn’t attempt to fix anything. Solomon simply describes depression and suicide in the many myriad forms that he has observed around the world. For someone going through depression, it can help (or at least, not make things worse) to simply see your feelings articulated in words. And I mean human words - not the stupidly rigid and sterile DSM-5 criteria for depression, which reads more like a badly written tech spec than a description of a deeply human experience.

Insecure/anxious attachment, for women: Women Who Love Too Much by Robin Norwood

Explains the whole “I can fix him” meme way better than I ever could. 🥲

Trauma and physiology: The Body Keeps the Score by Bessel van der Kolk

Necessary reading for everyone who is affected by trauma. And all childhood is trauma, so I guess that’s everybody.

Passion (or lack thereof) in long term relationships, and infidelity: Mating in Captivity and The State of Affairs by Esther Perel

For anyone who has ever loved. This TED Talk is a good start, if you want a taste.

Shame: The Upside of Shame by Vernon C. Kelly and Mary Lamia

This is a book aimed at clinical practitioners, actually, so the language is a little less accessible. But I think any reasonably intelligent human being could parse it and benefit from it. I don’t think I absorbed 100% of the clinical verbiage, though I did find a few helpful mental models in it - i.e. Silvan Tomkins' affect theory. What I found most compelling, however, was the very human case studies that relate shame to anxiety, depression, narcissism, borderline, ADHD, and couples.

Narcissism: Rethinking Narcissism by Dr. Craig Malkin

For anyone who has built armor around themselves (via badges of achievement, excelling at some kind of art / sport / craft / career, physical appearance, etc) - as a defense mechanism against feeling fundamentally not enough.

Anxiety / fear / selfishness: Fear by Thich Nhat Hanh

“As we talked, I was able to communicate that the war had created alot of victims, not only Vietnamese but also Americans. The soldier calmed down as well, and we were able to talk… If I had acted out of fear, he would have shot me out of his fear. So I don’t think that dangers come only from outside. They come from inside. If we don’t acknowledge and look deeply at our own fears, we can draw dangers and accidents to us.”

On playing the right game: Finite and Infinite Games by James P. Carse

Not quite a psychology book, but helpful for reframing decisions to create better outcomes, which is all that Cognitive Behavioural Therapy really is. Some mathematician can prove me wrong, but I’m pretty convinced that long-run enlightened self interest, played out on long enough of a time scale, is actually identical to genuine love and caring.

East Asian philosophy: Tao Te Ching by Lao Tzu (Stephen Mitchell translation is best)

“Things arise and she lets them come / things disappear and she lets them go / When her work is done, she forgets it / and that is why it lasts forever”.

A super aspirational life philosophy that I fail to live up to all the time, but that doesn’t mean it’s not worth trying. 🥲

A fun side fact about Stephen Mitchell: he translates many religious and philosophical texts, but doesn’t “speak or read a word of Chinese” - or most of these underlying languages. Instead, he reads all the other existing translations, and synthesizes them into his own version which tends to be more poetic, less literal, and somehow captures the original essence of the text in a way that a more literal translation simply does not. For my fellow machine learning nerds: think of him as a human ensemble method. 😉

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Thanks for joining me this week on But First, Entrepreneurs. Till next time! ❤️

If you liked this, you can find more of my personal writing at casey.li, or find me on Twitter at @sometimescasey.