Bold Moves: How Did You Know?

Kristen Rocco
  • 5.0 (23)
  • SELF-IMPROVEMENT
  • UPDATED BIMONTHLY

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.

  1. 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

    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)

    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

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

    JAN 22

    He Hid a Secret for 35 Years. How Vulnerability Changed His Life (feat. Mike Krupit, CEO, Trajectify)

    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

    38 min
  3. When NOT to Trust Your Gut + Leaving the Safety of Your Comfort Zone with Rachel Lipson, 2x Founder

    JAN 6

    When NOT to Trust Your Gut + Leaving the Safety of Your Comfort Zone with Rachel Lipson, 2x Founder

    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

    54 min
  4. Surviving a Stroke, Leaving Intel, and Building a Business with Erin Fortin

    12/16/2025

    Surviving a Stroke, Leaving Intel, and Building a Business with Erin Fortin

    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.comInstagram: @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

    42 min
  5. The Real Cost of Low Confidence (And How to Fix It) with Confidence Coach Simone Knego

    12/02/2025

    The Real Cost of Low Confidence (And How to Fix It) with Confidence Coach Simone Knego

    Did you know that women typically apply for jobs only when they meet 100% of the qualifications, while men apply when they hit just 60%? Even more concerning, nearly 80% of women struggle with low self-esteem and shy away from self-advocacy at work. This isn’t a competence gap. It’s a confidence gap. I sat down with Confidence Coach Simone Knego to discuss how women can start chipping away at these statistics by building unshakeable self-confidence. Simone is a best-selling author, two-time TEDx speaker, and the co-host of the podcast Her Unshakeable Confidence. But her journey wasn't a straight line. For years, she battled her inner critic of self-doubt rooted in past trauma and the pressures of comparison. From raising six children to summiting Mount Kilimanjaro, Simone discovered that confidence isn't something you are born with; it’s something you build in the messy, chaotic moments of everyday life. In this episode, she shares the raw truth about the cost of under-confidence and the practical tools she used to go from unsure to unshakeable. Simone teaches us: The REAL Method: A four-step framework (Respect yourself, Embrace your failures, Ask for what you want, Live without limits) to build lasting self-esteem.The "Control-Alt-Delete" Hack: A mental strategy to identify false narratives.How to rewire your brain: Why positive affirmations work scientifically and the specific "5 I's" Simone uses every morning.Reframing Imposter Syndrome: How to stop justifying your existence by dropping the word "just" (e.g., "I'm just a mom") and why feeling underqualified is often a sign of growth. 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 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 Connect with Guest Simone Knego Website: simoneknego.com Book: Real Confidence: A Simple Guide to Go from Unsure to Unshakeable at realconfidencebook.com Simone's reflection on how climbing Mount Kilimanjaro changed her life: https://simoneknego.com/how-climbing-a-mountain-can-change-your-life/

    51 min
  6. How We Built It: Content Marketing in the Age of AI

    11/18/2025

    How We Built It: Content Marketing in the Age of AI

    I'm so excited to be joined by a special co-host for this episode, Tyler Hakes. Tyler is the principal at the content marketing agency, Optimist, and we’ve been collaborating on a new project! In this “How We Built It” episode, Tyler and I pull back the curtain on our recent collaboration, where we launched a new methodology for content marketing called the Authority Moat Model. We show you how you can turn industry chaos—like the disruption we've all seen from AI—into a new market opportunity. Listen in to get the practical, three-part framework I developed from our process. We'll walk you through how to spot a trend, diagnose the real problem or unmet need it creates, and architect an innovative solution. This is a real-world case study for making a bold move inside of your bold move, whether you're an entrepreneur or an intrapreneur. And if marketing is your business, you’re in luck. We explain how our Authority Moat Model builds compounding authority and tangible ROI for your brand, inspiring trust with your audience in a way that AI never can. 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 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 Connect with Co-host Tyler Hakes On LinkedIn: https://www.linkedin.com/in/tyler-hakes/ Read our Authority Moat Model Transformation Narrative: https://www.yesoptimist.com/authority-moat-model/

    52 min
  7. Failing Forward with Michelle Beyo, CEO of Finavator

    11/04/2025

    Failing Forward with Michelle Beyo, CEO of Finavator

    Most people learn the rules and play the game. But what happens when you reject the rules everyone else accepts? For Michelle Beyo, CEO and founder of Finavator, rejecting convention started early. In this episode, Michelle shares the pivotal moment her entrepreneurial parents told her they didn't believe in university and wouldn't pay for it, advising her to “go work somewhere and learn something practical" instead. This bold rejection of a standard path led her to a year in Australia, taking jobs from barista to marketer to working on a camel farm. That experience taught her to be agile and fail forward —a lesson that would define her career. Michelle walks us through the rollercoaster of entrepreneurship, including the "trough of sorrow". She reveals how the catastrophic Silicon Valley Bank crash in 2023 became the catalyst for her biggest pivot: creating the "Future of Finance Masterclass." Join us to learn how to ride the highs and lows of any Bold Move journey and find the courage to fail forward. 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 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 Connect with Guest Michelle Beyo On LinkedIn: https://www.linkedin.com/in/michellebeyo/ Get a discount on Michelle’s “Future of Finance Masterclass” with code: BoldMoves25 https://www.finavatorfuturefinancemasterclass.com/offers/moerwgYe?coupon_code=BOLDMOVES25

    46 min
  8. Ex-CIA Analyst’s Top Secrets: Mind-Body Intelligence & Bold Move Intel, Revealed

    10/21/2025

    Ex-CIA Analyst’s Top Secrets: Mind-Body Intelligence & Bold Move Intel, Revealed

    Imagine your workday begins by delivering the world's most sensitive intelligence directly to the president of the United States. Sounds like a job for fictional characters like Jack Ryan, Carrie Mathieson (Homeland), ​​Owen Hendricks (The Recruit). But no. That was the reality for my guest, Kelly McGannon, during her 20-year career with the CIA. She delivered sensitive intelligence to two US presidents. Kelly's work profoundly shaped US policy, earning her the National Intelligence Meritorious Unit citation twice. More than an intelligence strategist, Kelly bridges her high-stakes career with a deep physical intuition honed through years of martial arts and practicing in high-stakes scenarios at the CIA. Kelly is one of the most exceptional storytellers I’ve met, and these are juicy! She shares how she got recruited to the CIA (does the gray man actually exist?), her boldest, hallmark moment leading to historic changes at the Agency, the myths surrounding the CIA, and how she initiated significant wellness programs within the Agency to cope with the psychological toll of her role. Kelly teaches us: How to remain anchored in your core values while navigating a demanding career and making bold moves.A practical technique you can use today for maintaining your calm in high-stress situations.How to tap into body intelligence for decision-making around your bold move.Why – not how – you should make a bold move. Push play now to be debriefed on bold moves from a former CIA analyst. I promise, you can't miss this one! 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 Connect with Guest Kelly McGannon On LinkedIn: https://www.linkedin.com/in/kellymcgannon/

    1h 4m
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About

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.

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