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Bold Moves: How Did You Know?

Bold Moves: How Did You Know?

Di: Kristen Rocco
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Welcome to Bold Moves: How Did You Know podcast! This is the podcast about the real stories behind the courageous, bold moves that change everything.

From building or rebuilding your career, launching or growing a business, or making a personal transformation to write your own story with intention, we explore what it takes to make a bold move and keep the momentum going.

Join host Kristen Rocco as she gets curious with guests who've navigated it all. In unfiltered conversations, they unpack the "click" moments that sparked their Bold Move and what it takes to maintain momentum.

Each episode centers on the question "How did you know?" to provide the inspiration and playbook for your Bold Moves journey. This is your permission slip to become the main character in your own life by making bold moves that align with your authentic self.

Connect with host Kristen Rocco on Substack: https://kristenrocco.substack.com/

Disclaimer: This podcast is presented solely for educational and entertainment purposes. I’m just your bold-moves-encouraging friend. I’m not a licensed therapist and this podcast is not intended as a substitute for the advice of a physician, psychotherapist, medical professional, accountant, lawyer, or other qualified professional.

Kristen Rocco 2023
Economia Gestione e leadership Leadership Successo personale Sviluppo personale
  • Bold Moves: Momentum-Building Strategies for the Year of the Horse
    Feb 19 2026

    In this Season 4 finale, I (host Kristen Rocco here!) explore four essential strategies that will help you create momentum for your bold move in 2026—the Year of the Horse.

    In the Chinese zodiac, the Horse represents unbridled speed and power, making this the perfect year to stop over-calculating and finally accelerate your bold move. However, even a horse at full speed can stumble if it loses its footing; this episode is your guide to surviving the "messy middle" of a bold move where the initial rush fades and the daily work begins.

    Bringing together the best insights from Season 4’s entrepreneurs, corporate leaders, and a former CIA strategist, this finale provides a tactical roadmap for generating momentum when the road gets rough. Whether you're building early momentum for a new bold move or need to break through a moment of paralysis, you’ll learn how to take the reins and turn potential stumbles into breakthroughs.

    Get the Bold Moves Momentum Audit

    Make your plan for maintaining momentum through the messy middle of a bold move. Find it on my Substack here: https://open.substack.com/pub/kristenrocco/p/momentum-building-strategies-for?

    What You'll Learn In This Episode

    Strategy 1: Building Early Momentum

    • Learn what Bold Movers do before they make the bold move to fuel momentum from the get-go.

    Strategy 2: Maintaining Momentum

    • Discover the internal tracks–the pre-built rails of systems, mindsets, and habits that allow your work to continue moving forward, even when your initial energy begins to fade.

    Strategy 3: Borrowing Momentum

    • Learn how others can help you generate forward progress in your bold move, as well as the difference between "Supporters" and "Elevators"—and why you need the latter to reach the next level.

    Strategy 4: Restarting Momentum

    • Explore what to do when you hit the "Valley of Trials" and your initial motivation completely disappears—including a 90-second biological hack for breaking through paralysis.

    0:00 Year of the Horse Energy

    4:08 Building Early Momentum

    10:38 Maintaining Momentum

    20:37 Borrowing Momentum

    28:20 Restarting Momentum

    35:45 Bold Moves Momentum Wisdom

    Featured Guests This Season

    Each guest’s full episode is waiting for you in this podcast's back catalog.

    • Erin Fortin - Process Engineer turned Bicoastal Photography Studio Owner
    • Sherehan Ross - Digital Marketing & AI Expert
    • Rachel Lipson - Founder, Blue Balloon Songwriting School
    • Genevieve Dozier - Corporate Leader & Entrepreneur
    • Michelle Beyo - Future of Finance Disruptor and Entrepreneur
    • Tyler Hakes - Entrepreneur & Growth Strategist
    • Ashley Cheretes - Corporate AI Marketing Leader
    • Simone Knego - Confidence Coach
    • Mike Krupit - Executive Coach
    • Kelly McGannon - Former CIA Strategist

    Love the Show?

    If these stories of bold moves have inspired you, please leave a rate and review on Apple Podcasts or Spotify. Your support helps other Bold Movers find this show and join our community!

    Connect with Kristen

    Stay connected between seasons on the Bold Moves Substack for behind-the-mic lessons and insights from my Bold Moves journey.

    Join me here: kristenrocco.substack.com

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    42 min
  • A Portfolio Career Identity: How to Be an Exec AND Entrepreneur + Rejecting the Career vs. Family Binary + Writing a Book at 30,000 Feet (feat. Genevieve Dozier)
    Feb 5 2026

    You might be asking yourself the question that haunts so many of us: “Is this it?”

    You’ve checked all the boxes. You have the title, the stability, and the resume. But internally, there is a restless voice asking if you are meant to grind this out for another 20 years, or if there is something more you’re meant for.

    The problem is, the idea of burning it all down and starting over feels terrifying. So we do nothing. We stay stuck in the safety of the known because the unknown feels reckless.

    Genevieve Dozier is here to prove that you don’t have to choose between two fulfilling choices.

    Genevieve is a Fintech leader who refused to accept the binary choice of "Corporate Executive" OR "Creative Entrepreneur." Instead, she built a Portfolio Career, simultaneously climbing the ladder at major financial institutions like BB&T and Fiserv while building her own business, Warpaint Consulting.

    In this episode, Genevieve challenges the "What if?" anxiety with a powerful new question: "Why not?"

    • Why not build an "insurance policy" for your career? Learn how a side business can be more than a passion project; it can be a safety net against layoffs and corporate volatility.
    • Why not be a C-Suite leader and a creative entrepreneur? Discover how to write books, speak on stages, and consult without losing your status as a respected executive.
    • Why not start right now, exactly where you are? See why you don’t need to wait for the "perfect time." Genevieve wrote her book on airplane tray tables while traveling for work, proving that boldness happens in the margins of your busy life.

    This episode has it all: Genevieve challenges conventional career wisdom, normalizes that it's okay to step in and out of a career, and shares exactly why it's important to build a portfolio career that serves you.

    She was able to become a portfolio career trailblazer because she sought out mentors and advice that opened her mind to what was possible. Now, she’s paying it forward to be that example for you.

    Join the Bold Moves Community

    Genevieve proves you don’t have to choose between your corporate career and your creative soul. Over on Substack, we’re exploring exactly how to make your 'something more' possible. Join the community: kristenrocco.substack.com

    Connect with Guest Genevieve Dozier:

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

    Website: https://warpaintconsulting.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

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    56 min
  • He Hid a Secret for 35 Years. How Vulnerability Changed His Life (feat. Mike Krupit, CEO, Trajectify)
    Jan 22 2026

    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.

    0:00 - Meet Mike Krupit, CEO of Trajectify

    1:52 - Personal Risk-Taking Leads to His Boldest Move

    7:44 - Mike's Professional Career

    15:27 - The Catalytic Moment that Changed Everything

    16:47 - Vulnerability Requires Courage

    25:11 - Sunk Cost Fallacy

    33:24 - If Not Now, When?

    Join the Bold Moves Community

    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

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    38 min
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