Founders are embracing executive coaching like never before (but not everywhere)
Welcome Entrepreneurs. I’m so glad you’re here.
Our camping excursion was the last trip of the Summer, and my work seems to be picking up on all fronts at once. I’m balancing a full client load of awesome founders (including two pro-bono early stage founders — a practice I plan to maintain moving forward), with the kickoff of the second cohort of On Deck Scale, with a new project in the intersection of entrepreneurship and racial equity.
Even though school doesn’t start for another three weeks, it feels like I’m mentally transitioning into Fall mode. I like the beach as much as the next guy. But more than that I’m damn grateful about the impact I get to make every day, and nearly giddy to see how all these projects unfold.
Let’s get to this week’s essay.
Founders are embracing executive coaching like never before (but not everywhere)
Last month, marketing Godfather Seth Godin wrote about why so few business leaders have coaches, despite the fact that at the highest levels of almost any other endeavor, most (if not all) of the top performers do. The article hit home for me, not only as a coach but as a former founder who for too long resisted the idea that I wasn’t already the perfect person to lead my company.
The good news is that I see every day how the resistance to coaching, to “talking about our challenges...setting goals...acknowledging that we can get better...eagerly seeking responsibility,” as Seth puts it, is changing. More and more founders and top VCs recognize the unfair advantage that coaching presents, and as a result, nearly half of all founders above seed stage (anecdotally, from my work with 100+ founders at On Deck Scale, and from spending any amount of time on tech Twitter) are working actively to improve their performance with an executive coach. The resistance to becoming intentionally uncomfortable with another human in service of becoming who you want to be is changing.
The bad news is that it’s not changing everywhere at the same pace.
Living in the Midwest and working on the coasts
I was born and raised in Michigan, an hour from where I write this. My favorite teams are the Lions and the Pistons, and it’s not close. I believe that Sleeping Bear Dunes is the most beautiful place on Earth (not only because I proposed to my wife there, in a full sweat after mistakenly thinking there was only ONE dune we’d have to summit, rather than 13). I appreciate people being kind to one another as a rule. From my perspective (don’t @ me), my home state is the soul of the Midwest.
I am invested in creating an amazing startup community in Michigan, and am dedicating much of my creative energy to projects in my local community. And yet the vast majority of the actual coaching work I do is with founders on the East or West coast.
At first I was surprised by this imbalance, but as I’ve dug deeper it’s started to make more sense. It seems to have a lot to do with culture.
How our culture determines what we see
Ask a fish “how’s the water?” and it will have no clue what you’re talking about. The water it swims in is as invisible to it as the air we breathe is to us. As invisible as our culture often is to us.
On the coasts, the West coast in particular, there is a culture of innovation. I recently wrote about how to build such a culture, and could have been describing (the good parts of) Silicon Valley. For any faults it may have, the startup culture on the West coast is undeniably innovative. Founders and VCs have managed as one to embrace failure in the startup journey unlike any other culture I’ve seen. And within a culture of innovation, a culture that embraces failure, surfacing your weaknesses to deal with them directly, is the obvious fastest path to growth.
On the other hand, in the Midwest we have a culture of hard work. You see it in our founders, our industries, and you see it in our sports teams. Our most successful basketball teams are the “bad boys” and the “goin’ to work” team, and our football team is built around biting people’s kneecaps. We have a chip on our shoulder, something to prove. We may not have the pedigree or the capital of the coasts (in fact it seems to me there’s an engrained assumption that we’re perpetual underdogs, whatever our actual status), but we will outwork everyone to make up for it. We’re used to getting the short end of the stick, but we won’t be stopped by it. We will overcome.
I speak from experience. The unrelenting workhorse ethos of Midwest founders is a superpower, and I wouldn’t trade it. But like all superpowers, it has a cost. And the cost of our Midwestern hustle shows up often when founders ask me about coaching.
When talking about coaching with a SV founder, they ask: “Will it improve my odds of getting the outcome I want?”
They’re always on the lookout for an edge, anything they can exploit to gain an advantage, and everything is on the table to get where they want to go.
When talking with a Midwest founder, they ask: “Do I need it?”
I know exactly where that skepticism comes from because I’ve felt it myself: “I don’t need help. I’m fine. Whatever it is, I’m up to the challenge, and I’ll prove it. I’ll overcome.”
And concealed underneath, if we’re being honest: “If I admit I need help, people will think that I wasn’t up to the task on my own. Better to muscle through than admit I don’t have it all figured out.”
So, do you need a coach?
The truth is that Midwest founders are right when we say we don’t need it. We don’t need coaches, or therapists, or any other personal support structures to succeed. We’re infinitely resourceful and capable, and the fact that we’ve built companies successful enough to make executive coaching relevant and accessible, in and of itself, proves we can do hard things. We as Midwest founders can and will overcome.
But — and I say this as a Midwesterner who ran a 100+ person company without any EA support because it seemed too posh — you don’t get any extra points in business for degree of difficulty. You don’t need help. But maybe it’s worth stealing from the folks out in SV, and asking yourself whether you’ll get to your goals faster by acknowledging that you’re not perfect and actively seeking ways to improve, or by burying the sensitive spots behind a wall of “I’m fine.”
(HT: Julie Mosow, Sarah Ramsey and Foster for editing)
THINGS I READ THIS WEEK
One: Letter on finding purpose and living a meaningful life (Hunter S. Thompson)
I wonder if this happens in other creative pursuits. The other day I read something that was so incredible it made me feel like a hack as a writer. A friend asked Hunter S. Thompson how to find purpose in his life, and what Hunter replied, in his mid-twenties, puts everything I’ve ever written to shame. The whole thing is even more complex given the fact that Hunter shot himself at 67-years old. But either way, the writing itself is electric.
While my own insight is similar, here, leave it to HST to remind me that there are levels to this shit. This might be one of my favorite pieces.
Two: When Buddhism goes bad (Dan Lawton)
Most everything you read about meditation frames it as a cure-all for whatever ails you. I think the meditation industrial complex plays a big role in this framing, as meditation is poised to be a $2bn market this year and meditation teachers are apparently not exempt from the desire to make money. But as a longtime meditator, I can say from experience that the experiences aren’t all as Zen as pop-culture would have you believe.
Here’s a first hand account of the wacky shit that can happen when you mess with your brain too much.
(Note: On balance, I think people should still meditate, but just maybe give yourself a Sacred Pause before you decide to go HAM.)
Three: Metrics needed to raise a series A (Annelies Gamble, Scribble VC)
Here’s a thing I wish I’d had when raising a Series A financing — an investor’s open book perspective on the metrics other companies are hitting at that stage. All companies/financings are different, but this is an awesome look at what your prospective investor’s other options are.
Four: The Bad Marriage Problem (AVC)
Speaking of fundraising, one thing that first time fundraisers often don’t consider is that the incentives are organized around shotgun marriages. As a founder your goal is to drive the most efficient process possible so you can get back to running the company, and as an investor your goal (when you want to invest) is to do so as quickly as possible to avoid too much competition.
So in each financing, both parties want to get hitched ASAP. I got into a bad shotgun marriage in this way circa 2012. Here’s one of the preeminent early stage investors saying it’s getting worse nowadays.
Be careful out there. A little time spent getting to know an investor outside your fundraise never hurt anyone.
WANT TO DIVE DEEPER?
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Executive Coaching for Entrepreneurs
There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.
I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency supporting founders to rapidly scale themselves as leaders, so they can thrive professionally and personally as their company changes the world. Leveraging 15-years as a founder/CEO and a decade of meditation & mindfulness training, I have helped leaders from companies across the world, funded by some of the world’s top venture funds, to design a more conscious life and make key changes to improve their performance and satisfaction. I coach entrepreneurs how I want to be coached:
Focused on the person, not the role.
Focused on results, without the fluff.