Why it was a great idea to rebuild a talk the night before presenting to 30+ intimidatingly successful founders

And what doing so taught me about leadership

Welcome entrepreneurs. I’m so glad you’re here.

Thank you to those of you who reached out after last week’s article about consciously resisting your phone’s agenda. I always love to hear from you, and it was really cool to hear your strategies for navigating this most intimate of relationships. I’m not ready to throw my phone in a dumpster, but perhaps a drawer from time to time :)

I had a pretty meta experience a couple weeks ago, giving a talk to the VC-backed founders in On Deck Scale. It started as a terrifying gauntlet being thrown down, and ended in an incredibly powerful conversation, with a whole lot of ambiguity and uncertainty in between.

It’s a fun story to tell, so I won’t spoil any more. Hope you enjoy.

Why it was a great idea to rebuild a talk the night before presenting to 30+ intimidatingly successful founders

“Life imitates Art far more than Art imitates Life." — Oscar Wilde

At 4:15pm the day before I was to give the talk, they asked me to redo the whole thing. 

In all the rules of giving presentations, "don't change the whole thing the night before" is right up there with "practice," and “know your audience.”  It's not something that you do, and I knew that.  But I also had a hunch.

I told them I'd give it a shot. 

---

My talk, called "The Dark Side of Crushing It," was about leadership. Using my own experiences as examples, the talk was about the way that many founders feel like they need to present themselves as 100% certain and confident about everything, and the issues that sustaining that type of persona can create in their business. The talk explores how trying to sustain a persona of success and certainty throughout the inherently uncertain process of building a business burned me out and nearly destroyed my business, and concludes with my hard-won learning that leadership is more about asking the right questions, rather than having all the answers.

My talk was about how leading through uncertainty requires leaning into that uncertainty, owning the fact that you don't always know what will happen, and instead asking the right questions to unlock your team's best performance. I’d given the talk to founders around the world to great reviews, and by this point had honed it to a fine point.  Good thing, I had thought, because this time I was presenting to 30+ entrepreneurs who'd raised collectively close to half-a-billion dollars in VC.  It was stupid to change everything the night before.  

But they said they wanted it to be more interactive. They'd gotten feedback from the entrepreneurs after previous talks that they were looking to be more involved with the speakers, and so my invitation was to turn a talk — a talk-talk, as in the kind in which I stand on stage telling a story, with no audience participation until the Q&A at the end — into an interactive workshop.  I had no idea how I would do it.  But I had that hunch, and over the last year I'd learned to listen to those feelings

I banged my head against the presentation for 90 minutes that afternoon before leaving it for the night, in precisely the same state as it was before my headache.  I still had no idea what I'd do. 

But I woke up the next morning and I knew.  I knew what I needed to do because it was obvious, once I'd seen it.  It was poetic.  It was also a big risk, and I was very nervous. 

I made the necessary changes, finishing the final tweak 16-minutes before showtime.  I took a quick walk around the block to clear my head, but my heart was still pounding as I logged into Zoom.  I had a sense that I was doing the right thing, but I had no idea how it would go.

-—

Three personal stories made up the meat of the talk, each the kind that I used to be scared to share with people. 

  1. How I'd lead our company into a boneheaded strategic move because I was too blind to listen to our team (lesson: "crushing it" leads to bad strategic decisions).

  2. How I'd boxed our team into the safe course of action by selling a very specific plan to our investors (lesson: "crushing it" stifles innovation).

  3. How, to keep up appearances in the face of serious problems, I eventually strapped on a mask to go to work each day (lesson: "crushing it" leads to imposter syndrome, and burnout).

I'd told those stories to audiences of founders before, but each time it felt raw.  Like I was sharing something that would cause the audience to think less of me. I knew intellectually that my story wasn't uncommon, but it was still agonizing to be the one taking that first step. I'd have to go first again this time, only this time, as I got to the point in the talk where I'd typically tell my story, if all went well I wouldn't be the one sharing.  This time, the talk would be interactive.  I hoped.  Either that or the voice in my head was right, and sharing my stories really did make me look incompetent.  

I explained the concept, how portraying an image of success and competence can lead to a leader making bad decisions because they don't listen to their team, instead focusing on being "right." I said this was the type of thing that happened to a lot of founders, and then instead of sharing my story, I asked what I hoped was the right question.  "Has anyone experienced this? Anyone want to share a story about being so convinced they were right that they missed what their team already knew?"  

And I waited.

Science says most humans can comfortably withstand four seconds of silence.  After five seconds everyone was still just looking at me, or down at their hands, or off screen at what was hopefully a monitor of my talk and not their email.  Everyone was not sharing a story like mine.  I felt exposed. 

I felt panic building in my chest.  I was almost ready to give in, to get it over with by telling my story as I had before.  But I knew if I did that the rest of the talk would be one way, and I'd be all alone.  I almost did it anyway.  

"I have a story like that," a founder said.

-—

When later I asked for someone to share their experiences around stifling innovation, I only waited a second.  And I had to choose between volunteers to share their story about wearing a mask to work.  Each story they told was very different from mine, but each fit perfectly, as if it were my own. 

During Q&A, a founder asked me if it was contextual. He said he felt like he'd become more successful as he stopped being open and instead intentionally curated an image of himself and his company as a rocketship.  But that along the way he'd also begun to feel more isolated and lonely.  He asked me, the speaker, what I thought.  And I said "it's a good question.  What do you guys think?" This amazing group of founders spent the next 20 minutes debating crushing it versus vulnerability, and I learned from their stories just how grey it all really is. 

In his book Crossing the Unknown Sea, workplace poet laureate David Whyte says that leadership “can never be legislated or coerced.  It is based on a courageous vulnerability that invites others by our example to a frontier conversation whose outcome is yet in doubt."  Building a company is an outcome which is yet in doubt. Rearchitecting a presentation, banking its success on a hope that an audience of uber-successful founders will volunteer to be vulnerable in front of their peers, is an outcome that is yet in doubt.  In the face of that doubt, I was scared.  I wanted to play it safe. 

But I was there to talk about leadership.  The kind of leadership that doesn't have all the answers, but rather leads from a worthy question.  So I asked the question, my reputation as a founder, coach and human being hanging in the balance (at least in my head).  I asked the question and had no idea what answers would come.

And it turned into the best talk I've ever given.

(HT: Nanya S, John Lanza, Kushaan Shah, and Compound for editing!)


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Who is Ryan Vaughn? 

I’m an executive coach for startup founders, a role in which I get to help high-performing founders expand into extraordinary leaders. I’m a 3x Founder/CEO who’s raised $20m+ in VC and built a market-changing company, as well as two other companies that taught me things. I’m an avid writer, meditator, reader, athlete, father, husband, amateur physicist, student of leadership, and adventurer. I’m also none of those things. But I am glad that you’re here.  If that’s not enough, here’s a more detailed bio.


FIVE THINGS I READ THIS WEEK

One: Capital gains, carried interest, and ordinary income (AVC.com)

This. This, this and a million times this. GP of Union Square Ventures and very public VC Fred Wilson going on record suggesting that the capital gains tax rate should be the same as income taxes of all kinds (lower income, raise CG). It would be so much simpler, and so much more equitable. Private Equity, VC and hedge funds have prevented this for a long time, but when the leaders of the VC community are starting to champion this change, it’s time.

LINK >>

Two: In search of amusement (Seth’s Blog)

“I’m not sure there’s an intrinsic reason that watching Avengers: Endgame ($400m budget) is more satisfying than solving an endemic problem (hunger, poverty, etc). We’ve simply evolved our culture to be focused on the business of amusement instead of the journey toward better.”

What if we started to value, with our dollars, things that mattered a bit more than movies?

LINK >>

Three: Why entrepreneurs need “inner work” (The Drama of the Gifted Child)

“Without therapy (or some type of intervening “inner work”), it is impossible for the grandiose person to cut the tragic link between admiration and love. He seeks insatiably for admiration, of which he never gets enough because admiration is not the same thing as love. It is only a substitute gratification of the primary needs for respect, understanding, and being taken seriously—needs that have remained unconscious since early childhood. Often a whole life is devoted to this substitute”

LINK >>

Four: Close (David Whyte)

I’ve found myself quoting Irish poets a lot recently. I wanted to share one with you this week. One that hits me right in my core, which found me by way of Brain Pickings (there’s a gem of a video at the link, if you’re poetically minded and adventurous).

CLOSE — by David Whyte

is what we almost always are: close to happiness, close to another, close to leaving, close to tears, close to God, close to losing faith, close to being done, close to saying something, or close to success, and even, with the greatest sense of satisfaction, close to giving the whole thing up.

Our human essence lies not in arrival, but in being almost there, we are creatures who are on the way, our journey a series of impending anticipated arrivals. We live by unconsciously measuring the inverse distances of our proximity: an intimacy calibrated by the vulnerability we feel in giving up our sense of separation.

To go beyond our normal identities and become closer than close is to lose our sense of self in temporary joy, a form of arrival that only opens us to deeper forms of intimacy that blur our fixed, controlling, surface identity.

To consciously become close is a courageous form of unilateral disarmament, a chancing of our arm and our love, a willingness to hazard our affections and an unconscious declaration that we might be equal to the inevitable loss that the vulnerability of being close will bring.

Human beings do not find their essence through fulfillment or eventual arrival but by staying close to the way they like to travel, to the way they hold the conversation between the ground on which they stand and the horizon to which they go. What makes the rainbow beautiful, is not the pot of gold at its end, but the arc of its journey between here and there, between now and then, between where we are now and where we want to go, illustrated above our unconscious heads in primary colour.

We are in effect, always, close; always close to the ultimate secret: that we are more real in our simple wish to find a way than any destination we could reach: the step between not understanding that and understanding that, is as close as we get to happiness.


Leadership is more than grand gestures. Bold vision statements and keynote speeches. I learned through the experience above that leadership is found in the small moments we get everyday. Every time we get to give a talk, or write a blog post or an email, or every time we have a meeting, all of these are opportunities to practice our version of leadership.

In each of these moments we can choose to give the talk we’re comfortable giving, or we can step into our role as a leader. I feel like I chose the latter in this situation, and am so grateful I did.

Ryan

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