Coaching for Demo Day
My week in SF with a batch of badass builders
Recently I got to spend a week in intimate coaching conversations with a batch of brilliant, young, insanely ambitious, insanely stressed-out founders as they prepared to pitch a room full of San Francisco’s most formidable investors at Entrepreneur First (EF)’s inaugural US Demo Day.
They all rocked their pitches. I’m still reeling from the sheer elation—one part maternal-ish pride and two parts childlike wonder—of watching them rock their pitches. Beyond the sheer delight of seeing them channel their stage nerves into the glorious recognition of what those 90 seconds could unlock for them, I knew I was getting a front-row seat to the future. A future that is “brighter, and [more] full of ‘tech magic’, than we can probably imagine right now”; a future built by immigrants from around the world, catalyzed by the culture and capital of Silicon Valley; a future that is magnificently, mind-blowingly, uncontroversially good.
Watch the whole event here (starting with Reid Hoffman’s inspiring intro) anytime you need a re-infusion of hope and optimism. Seriously, I highly recommend it.
But all of that is just preamble to what I really want to share about my week with these founders: a short sampling of some of the work they and I did together, as distilled into one fictionalized vignette (with details altered and aggregated for anonymity).
Stripping down to your “why”
Jack is a 21-year-old founder and CEO. His company is an AI startup that’s poised to transform the music industry. He has left behind his friends, family, and a high-paying job in his native country for a chance to build and fundraise in Silicon Valley. He’s already launched an MVP and his user base is growing exponentially. Yet, he tells me, the pressure to perform is constant and unrelenting, and while he’s pretty good at “putting on a show” for investors, it’s starting to take a toll.
I ask why he needs to “put on a show” at all? Because, he tells me, “you have to come off as super-confident to the point of arrogance” or VCs (venture capitalists) won’t invest.
But isn’t there something he is, in fact and not for show, genuinely confident about? Yes, he says: he did have some genuine conviction at one point about the future of AI and how it can save rather than destroy the music industry. But now that’s been buried under the “crushing fear of failure that’s been with me all the time since I got pre-seed funding and the stakes went up.”
Interesting. After some back-and-forth, it became apparent that he had linked his sense of self-worth to the standard of “not failing” in the eyes of some vague entity that amounted to “the world,” as currently represented by the median attitude of SF’s investors. Reflecting on why he cared so much, Jack recalled getting teased at school, and being a middle child with an inferiority complex; “isn’t this the sort of thing that drives every founder? The chip on your shoulder, needing to prove you’re not a failure, etc?” he asked, almost in resignation.
No, I said, not in my experience (though this is a common narrative in Silicon Valley and elsewhere). What drives the greatest and most enduring founders is that they love to build. So what motivated him, in particular, to build the things that got him to the point of attracting VC attention in the first place? Could he remember a time, however brief, when he wasn’t focused on trying to prove anything to anyone, but just on the joy of building things?
This was when Jack went quiet for a few beats. I noticed the first subtle hint of misting in his eyes as he said, “Yeah, as a kid sometimes; I would just make games or other cool stuff with code and share it with my friends.” As he recalled these moments, his back and his cheekbones visibly relaxed, as if he were setting down a heavy weight.
Wasn’t it that version of him that so impressed his first VCs (the EF team) that they decided to invest? Wasn’t it precisely that un-self-conscious kid with an audacious conviction about the future of AI, and with such an irrepressible love of building that he might just see it through?
Jack sat in quiet wonder for a moment, then said, “Yeah, wow… that really resonates.” But, he continued, what about all the other VCs—the ones who really are all about the show?
So then I asked him: what kind of VC does he actually want on his cap table (that is, owning a portion of his company)? What would be true of the sort of investor who really gets him and resonates with what he’s building? The same question applies here as on a first date, I pointed out: do you want them to fall in love with you, or with a fake version of you that you now either have to maintain—at the expense of the person you actually are and want to be—or else face irreconcilable conflict and disapproval when you finally drop the facade? You want to reach the investors in the room who want to flame-spot audacious and idealistic young upstarts like you; who’ve staked their careers and reputations on the thesis that the world needs more of just the kind of company you’re building; who resonate so hard with your story and are so wowed by your talent that they’ll be willing to invest in, nurture, and protect your agency as a founder.
Jack and I then built his “ideal investor avatar” together, and Jack rewrote his pitch for that investor. Suddenly, his story had a lot more “heart,” and—to Jack’s surprise—a much clearer financial upside, since it was suddenly much easier to see (and feel!) what Jack’s solution could be worth to music-lovers everywhere.
Then we wrapped up our coaching session and he went off to practice his Demo Day pitch, a barely perceptible bounce in his step. Several days later, I asked how he was doing, and he said: “I’m at peace with myself. The anxiety is gone.”
Come Demo Day, his pitch was electrifying and irresistible—precisely because it wasn’t “just for show.” Two weeks later, he informed me that he had successfully raised from one of the most prestigious, respected VC firms in the Valley.
My “why”
I held office hours and coached a couple dozen founders that week. There were some common denominators, given the looming Demo Day, such as anxiety about public speaking—with which I gladly have ample professional and personal experience. And the normal range of founder issues also came up: cofounder communication, managing one’s mind and work under extreme uncertainty, pushing against the limits of one’s own current competencies, and so on.
But every founder was unique. And it was my unique pleasure to focus on each person’s agency and psychology, to guide and advise and unlock, and to do so in person, in San Francisco, with a very specific near-term goal. Therapy and coaching often (with considerable justification) get a bad rap as indefinite and interminable, but, just like most work, they actually function best with clear goals and timetables.
A week of doing such work, with such a stellar batch of founders, was a concentrated reminder of why I’ve built my life around doing it.
❤️