I'm Tobey Wyatt

Why I Do This Work

I've walked into too many organizations hemorrhaging money on solutions that don't stick—because no one bothered to diagnose what was actually broken first. Band-aids on top of band-aids, each one more expensive to unwind than if they'd just found the root cause from the start.

I get fired up helping founders stop the bleeding and fix what's actually broken.

I think in systems. I honor complexity. And I know that drives some people crazy because they want "5 easy steps" or a simple answer. But business isn't simple—because people aren't simple. If you're struggling in your relationships, your marriage, your friendships, you don't suddenly become a functional leader just because you walked into the office. We're whole humans, and our dysfunction comes with us.

I'm not someone who "figured it out" and now teaches from the mountaintop. I'm doing this work alongside you—constantly learning better coping mechanisms, better strategies, more tools for the toolbox. Leadership is messy because humans are messy.

And it's lonely.

If you vent to your executive assistant, you create an unsafe dynamic. If you vent to your spouse, they might not have the context to help you be productive. If you vent to your friends, they'll take your side without challenging you fairly—because that's what friends do.

You need a space that's safe, judgment-free, AND productive—all three.

• • Safe: You can be fully yourself without creating psychological risk for anyone.
• • Judgment-free: I don't judge you for being frustrated, and I don't judge others based on your biased version of events.
• • Productive: I have the context and expertise to actually help you move forward, not just validate your feelings.

That's what I build. That's why I do this work.

Founders don't need to stay stuck in operator mode or give up their CEO seat to scale their companies. They need someone who can see what's actually broken, honor the complexity of fixing it, and walk alongside them while they lead.

Beyond Business

I live in Chicago's West Loop with my three daughters (4, 6, and 13). Weekend carpool karaoke around Chicagoland is a regular thing—we geek out on musicals like Hamilton, SIX, EPIC: The Musical (the Odyssey retelling that's not on stage yet), and we're constantly rotating through the KPop Demon Hunters soundtrack.

I'm a fantasy/sci-fi nerd at heart: Lord of the Rings, Fifth Element, The Witcher, superhero everything. I love escaping into stories. I also geek out over podcasts—SmartLess and Armchair Expert are on constant rotation—and I've learned a ton from Brené Brown, Adam Grant, and Simon Sinek.

I previously volunteered as a digital crisis counselor with The Trevor Project, providing overnight crisis support to LGBTQ+ youth. I had to step back to preserve my own mental bandwidth, but it's work I hope to return to when I have the capacity again.

My core value is authenticity—everything else flows from there. Integrity, compassion, candor—they all stem from being authentic to who I am and who I want to be. When I act out of alignment with that, I feel it immediately. I'm naturally an empath who's built my logical thinking over time through study and experience, balancing feel with think. I'm an E/INFP, and while I don't believe in astrology, I'll admit the Libra descriptions tend to resonate.