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. 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." 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: The Nonprofit: She's the FirstBold Moves: How Did You Know episode: The Real Cost of Low (And how to Fix It) with Confidence Coach Simone Knego

    42 min
  2. 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. 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
  3. 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. 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
  4. 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. 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
  5. 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
  6. What It Takes To Be First: Ashley Cheretes on Leading Prudential's AI Revolution

    10/07/2025

    What It Takes To Be First: Ashley Cheretes on Leading Prudential's AI Revolution

    We're live on Substack! Join us: kristenrocco.substack.com Being the first is bold. No one has gone before you. There is no playbook. You are charting the course, sometimes confidently because of your immense conviction and sometimes courageously because your gut sense is leading you. Being the first… that’s the theme of this episode with Ashley Cheretes, Director of Gen AI at Prudential Financial. When Ashley applied for a new director of Gen AI role at her organization, this is exactly what she confronted: an interesting job description in an emerging space that no one in her organization–or anywhere else for that matter–had ever done before. When you make your bold move, you’re going to be the first in some capacity. The steps to achieve your vision will look blurry. I asked Ashley how she is navigating being the first to help us all in our Bold Move firsts. From keeping a "kudos folder" to overcome bad days to figuring out how to overcome her stakeholders’ hesitations about a new technology, she shares practices you can embrace to help you confidently lead and navigate the path when no one has gone before you. Ashley teaches us her tips for: Overcoming imposter syndrome.What to do when you don’t have all the answers.How to break through the status quo to influence changeAnd much more This episode is a powerful two-for-one. You'll get actionable advice on the skills needed to be first in your bold move, alongside critical insights into AI from one of the industry's foremost experts. Ashley shares the same expertise she's brought to stages at Adobe Summit, The AI Leaders Forum, Boston University, and Vanguard, making this a can't-miss conversation. Stay tuned until the end for her rapid-fire answers to your pressing questions about AI: Where do you see AI being the most effective? What problems is it solving for businesses?What are AI’s limitations?What are the AI courses you recommend?What’s the predictive capability of gen AI?What’s Agentic AI? 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 Ashley Cheretes On LinkedIn: https://www.linkedin.com/in/ashleycheretes/

    52 min
  7. How to Execute Your Bold Vision in the First 90 Days of Your Bold Move with Sherehan Ross

    09/23/2025

    How to Execute Your Bold Vision in the First 90 Days of Your Bold Move with Sherehan Ross

    We're live on Substack! Join us: kristenrocco.substack.com Bold Movers, I am excited for you to meet Sherehan Ross, VP of Marketing at Modus Planning in this episode! As we transition into exploring a new question this season, how do you continue to be bold inside of your bold move, I knew Sherehan would be the perfect guest to kick off this season’s interview series! She has just started her next bold move, transitioning from fractional marketing consulting in her solo business to an in-house role where she’s leading the full marketing function from A to Z. She’s made the leap, and now it’s game time. How does she keep her bold vision in focus? Reflecting on our conversation, it struck me that Sherehan laid out a universal playbook for the first 90 days of any bold move, whether you're in a corporate role, an entrepreneur, or on a personal journey. In this episode, you’ll discover: The foundational framework that elevates her vision: “Learn, Plan, Do.” It’s a roadmap to guide clarity, focus, and decisionsWhy true boldness is about delivering value, not always being polarizing.How Sherehan's commitment to upskilling guides her to new bold thinking and ideasThe mindset you need to keep the momentum going And lots more, so tune in now! Did you hear our big announcement? I'm so excited to officially launch our new community and resource hub, The Bold Moves Substack channel! This is where we’ll connect, support, and elevate each other as we navigate our bold moves together! Join me and over 100 other Bold Movers there: 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 Sherehan Ross On LinkedIn: https://www.linkedin.com/in/sherehanross/ Take Sherehan’s course on “Using AI to Create Buyer Personas”: https://www.linkedin.com/learning/using-ai-to-develop-buyer-personas

    39 min
  8. What It Really Takes to Level Up

    09/09/2025

    What It Really Takes to Level Up

    We're live on Substack! Join us: kristenrocco.substack.com Hey Bold Mover! It’s your host, Kristen Rocco, and welcome to the Season 4 premiere! For three seasons, we’ve asked the question, “How did you know?” We focused on the toolkit, characteristics, and mindset it takes to make a bold move. But what happens after? What happens when you find yourself in the messy, unglamorous middle of your bold move, wondering, “Okay… what now?” “How do I navigate my bold move now?” That feeling is why, in this season, we’re going deeper. We're talking about how to build and maintain the momentum that keeps you going when the initial excitement fades and the real work begins. In this season premiere, I’m sharing the powerful mindset for keeping your momentum going when you’re in the thick of it: the decision to Rise to the Occasion. I’m also taking you behind the mic to share how I’ve been applying this framework in my own business—from navigating a new collaboration to leveling up my own skills to meet my ambitions. Tune in to discover the three-part framework for rising to the occasion in your bold move! In this episode, you’ll learn: How to apply a 3-part framework for Rising to the Occasion to keep your momentum going inside your bold moveWhy preparedness is the thing that helps you overcome self-doubt.How to put fear in the passenger seat to drive closer toward your goalsWhy embracing a growth mindset is more powerful than waiting for perfection. PLUS, a huge announcement! I'm so excited to officially launch our new community and resource hub, The Bold Moves Substack channel! This is where we’ll connect, support, and elevate each other as we navigate our bold moves together! If you’re dreaming of, planning, or already navigating your bold move and need the tools and community to keep going, this episode is your starting point! Connect with Host Kristen Rocco On Substack: https://kristenrocco.substack.com/ On LinkedIn: https://www.linkedin.com/in/kristenrocco/

    36 min
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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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