Welcome, Derek!
Welcoming Derek Haswell as Partner and Founder Coach
Welcome entrepreneurs! I’m so glad you’re here.
It was so much fun to hear from so many of you after my last post (I’ll peg the novel at 70% done with draft #2). Reminds me why I dedicated so much time to this newsletter in the first place. I’ll be back eventually, promise.
In the meantime, I’m very excited to announce some big time Inside-Out news: we’re welcoming Derek Haswell into the fold as a partner and Coach!
Derek co-founded the meditation company 10% Happier, where he spent a decade working alongside world-class meditation teachers (including Joseph Goldstein, Sharon Salzberg, and the Dalai Lama) while scaling the company to an 8-figure ARR. That experience — building a company while being surrounded by people who saw through every mask he wore — shaped how he coaches now. He blends outer work (strategy, goals, accountability) with inner work (self-awareness, resilience, what's actually driving the stuckness).
I’ve known Derek for years, as a coach, a builder, and a wonderful human being, and I’m so excited to get a chance to co-create Inside-Out with him, and support our founders in scaling consciously.
For those of you who haven’t yet met him, I’ll leave it to Derek to introduce himself. And if you want to reach out to Derek, the link is at the bottom.
Welcome Derek!
Derek Haswell
You don’t have to choose between building a world-changing business and becoming who you want to be.
I’ve lived that trade-off as a founder and it sucked… for everyone.
Then I discovered they could be part of the same path, and it changed everything.
Now I help founders make the same shift.
Here is my story:
In 2013, I accidentally co-founded a meditation company (10% Happier). We built an award-winning product, scaled to an 8-figure ARR, and worked with some of the best meditation teachers in the world (including the Dalai Lama).
I’m proud of what we built. But for most of that decade, I was quietly fueled by a need to be “enough”, and it cost me more than I knew.
In the early startup days, a burning drive to prove my own worth helped us toward early product-market fit. I was hungry for the right answers, so I dug them up. I wanted to look impressive, so I learned how to play the game. I added mask after mask to my trunk, and incessantly rummaged through them to find whichever one I needed to keep the show going.
Part of my role at the company was leading content, which meant working alongside some of the most highly-regarded meditation teachers in the world: Joseph Goldstein, Sharon Salzberg, Tara Brach, Jack Kornfield, Joan Halifax, and more. I characteristically threw myself into the work — reading their books, going on their retreats, and spending time with many of them in-person. I found them to be incredible people, unlike any I had met before, and their simple authenticity and powerful compassion left a mark.
While all of this was going on, my wife and I decided to start a family. First one, then two, and eventually three kids entered our family. It was life-changingly beautiful… and, at first, it was yet another surface area where I had to “do it all” and “get it right.”
With increasing clarity, though, the mix of company-building, meditating, wise elders, and parenthood held up mirrors where I couldn’t escape the uncomfortable truth: that no matter what I did or how well I did it, I still didn’t feel like I was “enough”
THEN I FELL APART
Eight days into a silent meditation retreat, I saw clearly for the first time just how deep it all ran.
The bigger themes were easy to spot. Work, family, school, sports. Accomplishments wherever I could garner them. Interesting, for sure, but nothing new.
It was a subtler awareness of my moment-to-moment experience that revealed something far more confounding. I was holding my belly in even through no one was looking. I couldn’t stop thinking of what I would say when the retreat was over. “Should I climb that tree over there? That would be funny.” My entire mental landscape was colored by the frame: “never enough, never enough.
At first it was amusing. Then it was harrowing. And then I fell apart.
For months after the retreat, while barely holding it together at work and at home, I wandered and I wondered what to do if I weren’t driven by an insatiable need to prove myself. The ever-optimizing mindset that previously gave me a sense of purpose now felt like holding a hot coal.
I was ready to re-orient toward a new path, but I had no idea how to find it.
THE ONLY WAY OUT WAS THROUGH
What followed wasn't a clean transformation. Parts of it were slow, meandering, and often confronting. Even with the support of my own coach, therapist, and teacher, it wasn't easy to take off masks that had been on for a few decades.
But parts of it went faster than I expected, and the benefits started showing up everywhere:
Having hard conversations got easier. Without needing to prove or defend myself, I could tell people what was true for me. And they could do the same in return.
My mind felt clearer. At work and at home, it was easier to find signal without all the noise. Decisions I was wrestling with became straightforward. Places that felt stuck moved more freely.
I cared more deeply. My aperture of concern more readily widened to embrace my family, my colleagues, our mission, our community — something I previously thought might dilute my energy and render me less effective had the opposite effect.
During this season, I remember letting go of all my “shoulds” — I should meditate every day, I should cook more meals at home, I should read that book, etc. It felt like a weight had lifted and, much to my surprise, the things that mattered the most to me felt easier to get done. Instead of having to push a rock uphill, I could finally let go and let the snowball roll itself downhill.
Both at work and at home, the last several years have been some of the most productive and aligned of my life. And this time, I’m actually enjoying the process.
I consider myself incredibly lucky, now, to coach other high-agency founders on a similar path.
MY WORK AS A COACH
My approach blends outer work (strategy, goals, hiring, accountability) with inner work (self awareness, inner harmony, resilience, values). I believe that addressing sticking points in both, and not focusing exclusively on one or the other, helps you become more integrated and authentic while moving towards your goals with more speed, energy & conviction.
I work with 20 founders at a time and what I’ve seen is that some of this happens gradually, but some of it goes fast.
The hard stuff doesn’t magically evaporate, but it becomes part of the developmental journey rather than the price of admission.
If this resonates, let’s talk.