What if you saw your vulnerability as a superpower rather than a sign of weakness?

Mike Krupit spent decades as a Silicon Valley daredevil, launching eight startups and handling millions without flinching, but he admits his most important Bold Move wasn't in business; it was finally taking off the mask he’d worn for 35 years.

In this episode, Mike peels back the layers on how he used professional risks to shield himself from personal vulnerability, and why dismantling the "tower" he built around his emotions was the only way to live an authentic life.

If you are projecting perfection, but underneath, you're really living behind a mask, you are likely causing your own setbacks and dissatisfaction.

We also dive into a tool called Autocratic Coaching to explain how micro-instructions can short-circuit the panic that comes with being vulnerable. Plus, we tackle the Sunk Cost Fallacy and why pivoting from something you've invested years in can actually be a great victory.

Tune in now to hear why vulnerability is the key that unlocks a whole lot more of your potential and how to start, one step at a time.

And over on Substack, we’re dropping the masks and building our "Bold Moves" muscle —one messy step at a time. Join us as we figure it out together: kristenrocco.substack.com.

Connect with Guest Mike Krupit:

Website: www.trajectify.com

Connect with Host Kristen Rocco

On Substack: kristenrocco.substack.com

On LinkedIn: www.linkedin.com/in/kristenrocco

Take the listener feedback survey: https://forms.gle/hBBKkKFVfbfzCFREA

Happy New Year, Bold Movers! I hope your 2026 is off to an incredible start. As we step into this fresh chapter, we’re setting intentions, resolutions, and goals, often relying on that inner voice to steer us right. But today, I want to flip the script on a piece of advice we usually accept as a universal truth. This is a vital conversation because it challenges a well-known convention, particularly if you struggle with anxiety.

You’re told constantly to trust your gut. It is the golden rule of intuition—if something feels wrong, don't do it. But what happens when your gut is driven by anxiety instead of wisdom?

For Rachel Lipson, founder of Blue Balloon Songwriting School and Brooklyn Family Travelers, learning not to trust your gut was the key to her bold move. As a child battling agoraphobia, Rachel’s intuition screamed at her to stay safe and stay home. If she had listened to that feeling, she never would have left Michigan or her reputable teaching job for something more that was calling to her.

In this episode, Rachel shares how she rejected the instinct to seek safety and moved to New York City to force herself out of her comfort zone. She reveals why “trust your gut” might be problematic advice for anyone with anxiety, and how she learned to proceed with caution instead of paralysis.

Rachel also walks us through her 17-year journey of entrepreneurship, sharing her brilliant metaphor for sustaining a business. Plus, we cover her latest pivot into Brooklyn Family Travelers, where she teaches families how to use credit card points to explore the world.

Hit play now and learn why you might need to stop trying to trust your gut to finally make your bold move!

Like this episode? There's a whole community of Bold Movers over on Substack. Join us and build your bold moves muscle with us! https://kristenrocco.substack.com

Connect with Guest Rachel Lipson:

Brooklyn Family Travelers: brooklynfamilytravelers.substack.com

Blue Balloon Songwriting School: blueballoonschool.com

Connect with Host Kristen Rocco

On Substack: https://kristenrocco.substack.com/

On LinkedIn: https://www.linkedin.com/in/kristenrocco/

Take the listener feedback survey: https://forms.gle/hBBKkKFVfbfzCFREA

Do you need a wake-up call to start following your dreams? And a roadmap for building a business that supports them?

Then let me tell you about my guest today, Erin Fortin.

In July 2024, Erin was in the prime of her life. She was healthy, active, and focused on building a thriving business. But during a routine jog with her husband, her world went black.

At just 37 years old, Erin suffered a stroke—a moment that stopped her in her tracks and completely reshaped her perspective on what it actually means to make a bold move.

Today’s episode is about that wake-up call. It’s about the shift from feeling invincible to realizing that we don't get a vote on when our time is up. This conversation of building her business is viewed through the lens of the urgent, new philosophy she now lives by: Don't Wait.

Before her health scare, Erin made a massive pivot from a "corporate robot job" as a chemist at Intel Corporation to building a business from the ground up: Erin Fortin Photography.

We discuss exactly how she navigated that transition and the systems required for building a business that could survive—and even thrive—during her six-month medical recovery.

We dive deep into:

• The Wake-Up Call: Erin’s candid story of surviving a stroke and discovering a hole in her heart she never knew existed.
• The "Corporate Robot" Job: How Erin knew it was time to trade her lab coat for a camera lens.
• The Math of the Leap: How she reverse-engineered her expenses and runway before quitting corporate life.
• Systems & Scaling: The specific tools and delegation strategies that kept her bicoastal business running while she was in the hospital.
• 📸 The Full-Circle Moment: A behind-the-scenes look at photographing an event in Gloria Steinem's living room.

Erin’s Bold Moves Advice: "We don't get a vote as to when and where and how we go. So do it now. Do it scared. Don't wait."

Like this episode? There's a whole community of Bold Movers over on Substack. Join us and build your bold moves muscle with us! https://kristenrocco.substack.com

Connect with Guest Erin Fortin:

• Website: erinfortinphotography.com
• Instagram: @erinfortinphoto

Connect with Host Kristen Rocco

On Substack: https://kristenrocco.substack.com/

On LinkedIn: https://www.linkedin.com/in/kristenrocco/

Take the listener feedback survey: https://forms.gle/hBBKkKFVfbfzCFREA

Mentioned in this Episode:

• Bold Moves: How Did You Know episode: The Real Cost of Low (And how to Fix It) with Confidence Coach Simone Knego