"After 20 years of dancing around it, I finally gave myself permission to become an entrepreneur - launching my venture studio: Riptide Holdings."

Peter GuySenior Tech Executive to Venture Studio Founder
Case Study

The Challenge

I was laid off in January 2024. On paper, it looked like a setback but in reality, it was a wake-up call. I'd been a senior tech and product executive for decades, moving from role to role every few years, never quite finding the perfect fit. Deep down, I knew what I wanted: to be an entrepreneur. But I'd been dancing around it for 15 to 20 years without taking the plunge.

What was stopping me? Three things. I lacked a clear vision—just a fuzzy, fragmented roadmap. I didn't have the right support network. And my limiting systems around time weren't working. While I didn't know what came next, I knew one thing for certain: I didn't want to go back to the same corporate setup. My 50th birthday was looming. The clock was ticking. And I had real work to do; work that, despite my immersion in self-help books and courses, I'd never actually done.

The Goals

CAREER: I wanted a new career that is more creative, entrepreneurial, and spread across various activities and businesses—not a single job.

NETWORK: I'm extremely extroverted and get my energy from people, so I wanted to engineer my life to spend more time with like-minded people to unlock energy, advance ideas, surface collaborators and partners.

HOW I THINK & FEEL: I wanted to trust myself and the process, allow myself to fumble and be human, take action (not just stay in my head), and be authentic.

The Journey

I started with a coach because I had this venture studio idea, but I felt paralyzed. Part of me was afraid of committing and taking a risk. I also recognized that I'd had deeply embedded patterns of being an employee, of comfortable, low-risk careers. I knew there was hard work I had to do that I'd never done before, and I needed help.

The coaching had a lot more inner and emotional work than I expected, but it provided a good balance. Most importantly, it helped provide clarity that I was missing about where I wanted to go and what mattered to me. I discovered a disconnect: the stuff I read and consumed frequently had no overlap with the work I’d been doing with enterprise software. For the first time I started to give myself permission to consider a more creative, entrepreneurial career.

The program taught me to chase the sparkle—the stuff that excites me—even if it's not obvious today how it makes economic sense. It taught me to trust myself and the process, that it's not going to be a linear process to just execute. I need to allow myself to fumble and be human. What's critical is that I'm taking action, not just in my head, and that I'm being authentic.

Through this, I developed a North Star that captures my mission and allows me to evaluate different jobs and career ideas. One of the biggest insights for me was the role that I play as a connector. Whenever somebody has said this about me, I've dismissed it as shallow praise. But now, I finally see it as something I do well, effortlessly, and not everyone can do this and this has been an unlock for how I think about my work going forward.

The Results

MY CAREER: Launched Riptide Holdings, my venture studio and reframed my professional identity from corporate executive to creator, investor, and advisor to my own businesses and ideas. In discussion with film executives to turn a favorite book, An Honest Man, into a movie. Created Rice Pudding, a personal growth AI prototype.

HOW I THINK & FEEL: Moved from paralyzed and afraid to actually doing it. I gave myself permission to be an entrepreneur and started taking action. I’m leaning into my connector superpower. And I’m following a responsibly focused plan instead of trying to do everything at once.

The Summary

Anne is doing her life's work by helping you discover yours. I was first drawn to her program's thoughtful and comprehensive structure, and I believed her corporate background would help her understand mine. That was true—but what surprised me most was the emotional and spiritual depth of her approach. Anne quickly saw through my unhealthy deflection patterns and gently guided me to a new place. By the end of our work together, I had unblocked myself, could see myself in a new light, and walked away with an inspiring roadmap, the tools, the conviction and courage to pursue what my heart wanted but my head had previously feared. That's Anne's superpower: bringing your head and heart onto the same beautiful page.

Want this for yourself?

Your Character is your compass to your best career and life.