Escaping the Wonder Bread Experience: Executive Coaching for Entrepreneurs
The Case for Bringing Your Soul to Work in a World Obsessed with Professionalism
I spent years hiding my true self in tech, not realizing there was another way. As a female, 20-something businessperson in tech, I had all the excuses to hide. All the reasons to fit in. But when I started to abandon that need to conform, that’s when success started coming.
I remember the moment I took a stand as a loving leader. I had just attended the Reboot CEO Bootcamp, where Jerry Colonna expertly asked me one important question: "Why did you start your company?"
We skipped the standard investor-friendly response about market opportunity and instead dove into my experience of being bullied at school when I was 10—the times when it was so painful I had to eat lunch alone in the bathroom.
That’s when it clicked: I started a group meals company to ensure no one ate alone.
The love from that memory informed not just the founding of my company but the way I led it. I’ve always cared about people’s emotional experiences. I’ve always wanted them to feel included and important—probably because I was excluded as a child and felt insignificant.
But this care for people’s emotions did not translate to the textbook tech founder. The origin story of bullying was not something most investors were used to hearing.
Who cares? It was my story.
The Problem with Standardized Advice
I’m personally tired of the standardized advice about how to raise money or best practices for a "good culture." What even is a good culture? Culture is a reflection of the leader. It has its good, bad, and ugly. Some skew less healthy than others. But to have one playbook for all tech cultures is… well, it’s boring. It’s homogenous.
Tech is prone to a Wonder Bread experience because founders are afraid to deviate from the norm and fail. "The odds are already against me," they say. "Why risk it?"
You risk it because your company is default dead. Start with the assumption of failure. The majority of the smartest, brightest minds in the industry have failed. That’s where you’ll likely end up. Let that be soothing. Nowhere to go but up.
Death is guaranteed, life is not.
Do you want to go to the graveyard without actually swinging for the fences?
The Pressure to Conform—Even as a Coach
Even now as a coach, I feel the pressure to fit in. To showcase that I’m a "serious" coach, with proven experience and accolades to make myself look like other master coaches. But I don’t fit the mold—I’m not the standard ethnicity, gender, or even age of what you imagine when you think of a coach (a la Trillion Dollar Coach). I never coached a sports team and I suck at sports analogies (unless it involves surfing).
I believe workaholism is as dangerous as any other addiction. I’m scared to say it because I have this belief that, as an executive coach for entrepreneurs, I’m supposed to help founders work more! I’m supposed to feed that success.
But I don’t want to be a coach that fuels that unhealthy external validation from work. I’ve seen that path end in burnout, shame, and disease (I’m raising my hand to all of these).
I’m not trying to make founders work less, but I am trying to help them build a healthier relationship with work—one where it isn’t their only source of validation and worth. Where they work in alignment with their values and dreams.
Success Without Soul is Meaningless
What’s missing for founders are coaches who lovingly challenge professionals to stop being… well, so damn professional! I get it: we all want success, achievement, that next round of funding. But most advisors, investors, and mentors who counsel founders take the path of the known, the "best practices."
What about the soul? At some gut level, employees, investors, and customers flock to leaders with soul, with that sense of passion, that sparkle in the eye that fuels tenacity and the desire to build big.
That’s why executive coaching for entrepreneurs needs to go beyond traditional success metrics. Go be successful. Go rock your industry. But don’t forget your soul while you do it.
Soul-driven, emotional founders often feel they have to hide. And I’m here to help you reveal more of that soulful, creative side. My coaching practice reflects a core philosophy: authenticity breeds success. It is in embracing who we truly are and leading from that place that we make our voices known.
Embracing Soul Encounters
Those who support founders cannot neglect the soul. We must nurture and embrace soul encounters—moments when a leader comes into contact with something unknown, mysterious, and uncontrolled. Moments where something inside their world emerges to the surface, in ways that surprise and can cause chaos. I sometimes see my work as "surfacing" work—finding situations that open up the window of self a little wider, so you can know yourself a little deeper.
Take the Swing
Take the risk of being you. You’ll experience rejection; some people won’t like who you are and what you represent. But that’s well worth the genuine loyalty—and even love—of those teammates and customers who adore you and what you stand for. Those supporters will never have the opportunity to know you if you don’t show up.
Show up. Be weird. Wave your freak flag. It makes the journey interesting and energizing for others, but most importantly, for you.