Grant Winns: What Four Successful Exits Taught Him About Self-Doubt
Every founder deals with self-doubt, but most never tell anyone.
In the very first episode of The Founder Exhale, I sit down with Grant Winns, an 8-time founder with 4 successful exits, including the globally recognized brand BYLT Basics, and CEO of Yuna Health, an AI-native mental health platform built to fill the gap between crisis care and traditional therapy.
Grant gets real about the mental health challenges across two decades of entrepreneurship, what self-doubt actually looks like from the inside, and why he built Yuna Health for a version of himself that needed it most.
In this episode:
We get into self-doubt and how it showed up for Grant from the very beginning, when he dropped out of school, moved to California, and bet on himself with his first company. We talk about the difference between your startup happening because of you, of you, and through you, and why that third level changes everything for your mental wellness.
Grant shares why he kept his self-doubt completely private for the first three quarters of his career, what he was afraid would happen if people found out, and why he now believes sharing it is the move.
We also dig into confidence, what it means to wear it as armor versus build it as a muscle, and how, as a kid, Grant had a wrestling match while terrified and still won. And Grant shares something he says he's never said out loud on a stage or in an interview: that even after his biggest wins, he still felt like a failure.
What you'll hear:
Grant's framework for moving from self-doubt to action, starting with your inner circle and working outward. Why journaling your fears is one of the most underrated tools a founder has. The three levels of entrepreneurial identity, and why "this thing is coming through me" is the one that protects your mental health. Why the unspoken, unclarified fear is the dangerous one. Mike Ma's chapter in Burn Bright, Not Out, "You Are Your Startup. You Are Not Your Startup." and why it hits different after hearing Grant's story. The Gain and the Gap by Benjamin Hardy, and why Grant thinks founders spend too much time staring at what's ahead instead of how far they've come.
And Grant's final message to any founder sitting alone right now, dealing with self-doubt and not telling anyone.
The gift:
Yuna donated 300 free licenses to the Kabila Founder Mental Health Fund for founders in my ecosystem. That's $60,000 worth of access to an AI mental health companion, at no cost to you. Go to yuna.io/founderexhale to activate yours.
Timestamps:
02:05 Grant's journey and the personal story behind Yuna Health
04:05 How I use Yuna daily and what it's done for my mental wellness
05:40 Self-doubt as a founder: Grant takes us back to the beginning
08:25 Do I have what it takes? The imposter syndrome nobody talks about
11:14 The three levels: because of me, of me, and through me
12:52 Who did you tell? Grant's honest answer for the first three quarters of his career
16:06 Wearing confidence as armor vs. building it as a muscle
18:29 The wrestling match, fear, and acting as if
22:52 Succeeding on paper while feeling like a failure inside
29:40 Therapy, Yuna, and what finally moved Grant from clinical back to functional
33:15 What to do right now if you're a founder sitting alone in self-doubt
35:05 The dad joke (it's founder-specific, I'll let you decide if it lands)
37:22 How to connect with Grant and claim your free Yuna license
Resources and links:
Yuna Health: Free Yuna licenses for founders
Grant Winns on LinkedIn
Grant's email: grant@yuna.io
James' book: Burn Bright, Not Out
The Gain and the Gap, by Benjamin Hardy
Kabila Founder Mental Health Fund
The Founder Exhale website
Support the work:
The Kabila Founder Mental Health Fund has awarded nearly 90 mental therapy grants to founders who need support but can't afford it. If this episode meant something to you, please consider being a donor at kabilamentalhealth.com. Every dollar helps a founder get the support they deserve.
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Be well, y'all. 🤠
