Best Brett Trainor Podcasts (2025)

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What Happens When You Quit Corporate Without a Plan with Brett Trainor | RR324 39:37

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13d ago39:37

39:37

You don’t need a plan if you’ve got the right people in your corner. I loved this chat with Brett Trainor, who walked away from corporate life and found something even better—freedom, purpose, and a community of support. Brett shares how his journey unfolded not through strategy, but through relationships. From his first freelance gig to building t…

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Nail Your Messaging and Master the 6 Questions Every Client Will Ask w/ Tom Freedman 50:22

6d ago50:22

50:22

One of the biggest challenges GenX escapees face after leaving corporate isn’t expertise—it’s business development. How do you find customers, create clarity in your message, and grow without getting stuck in trial-and-error mode? In this episode, I sit down with Tom Freedman, a lifelong entrepreneur who has built six businesses and now helps solop…

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Reading the Inner Profile Picture: Body Language, Tone, and Authenticity in Sales Conversations 30:07

5d ago30:07

30:07

In this episode, Jake explores how to decipher a prospect’s true feelings by reading beyond their words... tuning into posture, cadence, tone, and microexpressions to uncover their inner profile picture. You’ll learn: Why the outward profile we show can mask deeper motivations, needs, and desires. How skilled salespeople read urgency and excitement…

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Why B2B Relationships Start Before the First Pitch with Michael Haynes | RR325 44:48

6d ago44:48

44:48

Are your client relationships strong enough to earn their trust before the first pitch? Michael Haynes, a B2B market specialist, author and speaker, joins me from Sydney. He guides us on how to unpack what it truly takes to win and keep business clients today. It’s not just about being client-focused anymore—it’s about becoming buyer-centric. We ta…

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From Corporate Stress to Strength Training: A Dual Playbook for GenXers 29:34

11d ago29:34

29:34

Dual Takeaway: This episode is a two-for-one: inspiration for escaping corporate and practical fitness guidance for living longer, stronger, and on your own terms. What happens when you realize corporate life just isn’t for you—before it consumes decades of your career? Greg Bogdanski found out early. After stints in investment banking and consumer…

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Laid Off After 27 Years—And Finding Fulfillment Beyond Corporate w/ Thea Watkins 36:26

11d ago36:26

36:26

After 27 years in corporate—including an executive role—Thea Watkins never imagined she’d end up running her own business. A layoff forced her to pause, reflect, and rethink what she really wanted. Instead of jumping back into another corporate job, Thea leaned into her passions: leadership, people development, and inclusive workplaces. Today, Thea…

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Choosing Your Network Wisely With Nancy Fox 34:23

13d ago34:23

34:23

In this episode, Jake chats with Nancy Fox, a seasoned fractional executive coach and author who specializes in helping professionals make smooth entrepreneurial transitions. Nancy shares her insights on the myths fractional executives face and the reality of building a quality network focused on decision makers. You’ll learn: Why your network is y…

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Portfolio Life: Building Purpose and Freedom After Corporate with Joy Levin 40:40

17d ago40:40

40:40

What does “retirement” really look like for Gen Xers—and why do so many struggle with it? In this episode, I sit down with Joy Levin, market research consultant turned retirement coach, who helps Gen X professionals design their encore years with purpose, connection, and freedom. We dive into: Why retirement is no longer a five-year chapter but a 3…

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Summer of STRATA - Action: Closing the Sale by Making It Their Idea 25:17

20d ago25:17

25:17

In this episode, Jake unpacks the final step in the STRATA framework: Action. You’ll learn how to get prospects to naturally follow through on the ideas and excitement you have cultivated throughout the sales process. You’ll discover: Why the best sales pitches make the idea feel like the prospect’s own. How a thoughtful call to action is a gentle,…

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The Secret to Building Real Trust in Business with Carl Walsh | RR323 41:03

21d ago41:03

41:03

Great leadership starts with backstage conversations, not just center-stage charisma. I had the best time talking with Carl Walsh—award-winning actor turned business coach—about how the principles of theater can shift the way we build teams, lead people, and run companies. Carl’s path from the Royal Academy of Dramatic Arts to working at Disney and…

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UGC for Gen X: How to Make Money Creating Content (No Followers Needed) W/Megan Collier 40:38

25d ago40:38

40:38

Episode Summary: Think UGC (User Generated Content) is only for 20-somethings? Think again. In this episode, I’m joined by Megan Collier—UGC creator, coach, and champion for Gen Xers and Boomers who want to turn their creativity into a revenue stream. Megan shares how she went from scrolling TikTok with just 200 followers to replacing her six-figur…

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The Integrated Entrepreneur - Embracing the Whole Self with Raeanne Lacatena 34:47

27d ago34:47

34:47

In this episode, Jake welcomes Raeanne Lacatena, holistic business coach, Reiki master, and author of "The Integrated Entrepreneur." Raeanne shares her unique approach to blending personal development with business growth, helping entrepreneurs embrace their whole selves... not just their professional personas. You’ll learn: What it means to be an …

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Trevor Turnbull’s Wake-Up Call: Why Hustling Wasn’t Working | RR322 43:56

28d ago43:56

43:56

Burnout can be the wake-up call that shifts everything. I loved reconnecting with Trevor Turnbull, a long-time entrepreneur who’s done it all—from building a seven-figure agency to living off the grid in Costa Rica. We talked about what happens when business success no longer feels fulfilling and how that realization sparked a full reset. Trevor sh…

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Summer Of STRATA: Transfer - Making Your Idea Their Idea 27:16

1M ago27:16

27:16

In this episode, Jake dives into the “Transfer” step in the STRATA framework and reveals how the best sales pitches make the idea feel like it’s the prospect’s own. Y ou’ll discover why leading the prospect to their own conclusion dramatically reduces resistance and buyer’s remorse. You’ll learn: Why pushy, scripted sales pitches back prospects int…

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The Secret to Getting Clients from Your Content | RR321 49:32

1M ago49:32

49:32

What if your content could build real trust instead of just chasing likes? If you’ve been putting in the effort but not seeing results, Josh Spector wants to change that. He’s a content strategist, creator of For the Interested, and an expert in turning content into client relationships. Josh shares how to stop spinning your wheels with low-impact …

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Clarity, Connection, and Confidence with Paden Squires 32:21

1M ago32:21

32:21

In this episode, Jake welcomes Paden Squires, a dynamic CPA and podcast host breaking the mold with a unique blend of social charisma and financial expertise. You’ll learn: How Paden’s journey from rural beginnings to thriving entrepreneur blends personality with precision. Why clarity and focus in your messaging and network are essential to attrac…

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Kelly Sinclair’s Authentic Approach to AI-Powered Marketing | RR320 35:23

1M ago35:23

35:23

You don’t need to be tech-savvy to build authentic visibility with AI. Kelly Sinclair, brand visibility coach and host of the Entrepreneur School podcast, returns to share how she’s helping entrepreneurs use AI tools without losing their human voice. We talk about time-saving strategies, keeping messaging true to your values, and how something as s…

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Summer of STRATA: Anchor - Shifting Perspectives to Win Sales and Build Trust 34:23

2M ago34:23

34:23

In this episode, Jake dives deep into the “Anchor” layer of the STRATA framework, exploring how shifting anchors can transform sales conversations and help both sellers and buyers make better decisions. You’ll learn: Why everything we make important can become the anchor for ourselves and others, and why price is often the default anchor in sales. …

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Turning Small Talk into Business Gold | RR319 39:24

2M ago39:24

39:24

You don’t need hours to build trust. You just need 15 seconds and the right words. I recently sat down with Jen Mueller, an Emmy-winning sports broadcaster and founder of Talk Sporty to Me, who’s built a career turning lightning-fast locker room chats into meaningful connections. Jen shares how her experience interviewing athletes in 15-second wind…

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From Burnout to Purpose: Escaping Corporate and Building a Life That Works 48:45

2M ago48:45

48:45

In this special episode, Brett flips the mic and joins John Browning on the Building Your Life Podcast. They dive deep into what it really means to escape corporate life and build something better—on your terms. Brett shares: • His journey from 25 years in corporate to solo consulting and fractional work • Why GenX is waking up to the reality that …

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Market Eminence and Professional Sales Wisdom with David Newman 35:41

2M ago35:41

35:41

In this episode, Jake hosts David Newman, founder of Do It Marketing and a seasoned expert in professional services marketing and sales. David shares his journey from corporate consultant to influential author and coach who helps entrepreneurs build market eminence and master sales. You’ll learn: Why having people love you... and hate you...is a si…

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How to Turn Small Stories into Big Results | RR318 35:38

2M ago35:38

35:38

Your story isn’t fluff. It’s the foundation of trust, connection, and business growth. Renee Lynn Frojo, brand storyteller and founder of A Good Reputation, shares this and more with me in this episode. Renee helps purpose-driven entrepreneurs discover the power in their personal stories and how to use them as a business strategy. We explored how t…

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Summer Of STRATA: Reframe - Changing The Lens To Create Opportunity 28:28

2M ago28:28

28:28

In this episode, Jake explores the critical STRATA layer called Reframe and how shifting perspective on pricing, objections, and value can transform your sales conversations. You’ll learn: Why it’s never about price alone, but about the perceived value and the cost of inaction. How to separate the concepts of worth, price, and value and charge acco…

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Self-Awareness and Style that Moves Business Forward | RR317 36:56

2M ago36:56

36:56

The parts of you you’ve been hiding might be the key to your boldest moves yet. I had the pleasure of talking with Danielle Mohr and Shelby Eloria, the women behind Black Sheep Co, about something we don’t talk about enough—the relationship we have with ourselves. We dug into what it means to reclaim your voice, rediscover your identity, and stop s…

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Building Genuine Connections and Taking Action with Brett Trainor 37:41

2M ago37:41

37:41

In this episode, Jake sits down with Brett Trainor, a leading name in the fractional community, who shares his journey from corporate life to entrepreneurial freedom and how he built an authentic, engaged network from scratch. You’ll learn: How shifting mindset from “what am I going to get out of this call” to “how can I add value and learn” change…

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Breaking the Cycle: Letting Go of Money Beliefs That No Longer Serve You with Sloan Wilkins | RR 316 36:39

2M ago36:39

36:39

What if talking about money felt more like connection than conflict? My guest today, Sloan Wilkins, brings a calm, thoughtful approach to something that often feels heavy—money. Drawing from his own experience with childhood financial loss and a long career in banking, Sloan shares how mindfulness and intention can reshape the way we manage, talk a…

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Summer of STRATA: Trigger – Activating the Right Responses to Connect and Convert 24:33

3M ago24:33

24:33

In this episode, Jake explores the power of Trigger, the second layer in the STRATA framework, and how understanding and leveraging triggers can dramatically improve your sales and business development. You’ll learn: Why selling the results and the life your client will have with your product beats selling features and benefits. How to spot the sig…

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The Storytelling Shift That Will Make Your Clients Say Yes | RR315 35:52

3M ago35:52

35:52

Sometimes the simplest changes make the biggest impact—and that’s exactly what Kris Jones shows us in this episode. She breaks down the power of storytelling in a way that instantly makes you rethink your website, your LinkedIn profile, and how you're connecting with clients. It's not about you; it’s about the story you're inviting your clients int…

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Communicating Your Value as a Fractional Leader with Jason Jones 38:42

3M ago38:42

38:42

In this episode, Jake chats with communication coach and fractional leadership specialist Jason Jones about how totally different the game is when shifting from corporate job interviews to authentic business development conversations. Jason breaks down why success isn’t about blasting generic pitches, but about getting deeply relevant to the client…

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Redefining Success on Your Own Terms with Kym Insana | RR314 33:38

3M ago33:38

33:38

Let’s be real. Scaling a business while parenting isn’t easy, but, believe it or not, it is possible when you create it on your own terms. Kym Insana didn’t start out trying to build an agency, she just wanted a life that worked for her and her family. What happened next was a business that grew from word-of-mouth relationships, smart strategy, and…

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Escape Without Breaking: Shelley McIntyre’s 3-Phase Framework for Leaving Corporate 38:25

3M ago38:25

38:25

She’s back for part two! Shelley McIntyre returns to break down the exact framework she uses to help burned-out GenX professionals escape corporate life—without hitting rock bottom first. If part one was about why we escape, this one is about how to do it—mentally, emotionally, and tactically. We cover: • Why grief is a part of every transition (ye…

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Signal: The First Layer of STRATA and Its Power in Business Development 28:33

3M ago28:33

28:33

In this episode, Jake digs into the critical power of Signal, the first and arguably most important layer of the STRATA framework. Signal is all the tiny but impactful cues we give off long before we say a word, from punctuality to posture, phone usage to tone, our vibe sets the stage for every interaction. You’ll discover: How unconscious signals …

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Breakthroughs for the Overwhelmed Brain with Barb Hubbard | RR313 36:41

3M ago36:41

36:41

Just because you feel scattered doesn’t mean something’s wrong with you. You might just need a new way to make things work for you. Barb Hubbard, ADHD coach, educator, and author of Quit Chasing Squirrels and Start Chasing Your Dreams, brings a fresh, compassionate approach to helping high-achieving professionals and solopreneurs stop spinning and …

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The LinkedIn Escape Plan: How Joe McKay Left Government and Built a Life in France 51:27

3M ago51:27

51:27

Joe McKay left a government job in Australia to raise his family in rural France—and stumbled into the solopreneur life along the way. In this episode, Joe shares how one consulting gig turned into a thriving ghostwriting business and agency, all built on the back of his personal brand on LinkedIn. We talk about: • The “fork in the road” moment tha…

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The Anti-Hustle Guide to Doing Better Work with Paul Shirley 53:48

3M ago53:48

53:48

This isn’t a future-of-work episode. It’s a how-to-work-differently episode. Paul Shirley returns for his third appearance on the show—and this time, we go deep. We’re talking focus, structure, guilt, failure, personal infrastructure, and why GenX escapees need systems more than strategies. If you’ve ever felt like: • You “should be able to do more…

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Building Trust and Relationships with Todd Wilkowski 31:18

3M ago31:18

31:18

In this episode, Jake welcomes longtime friend and fractional general counsel Todd Wilkowski to the show. Todd’s journey from commercial litigator to trusted problem solver in the business world reveals the power of relational sales and the importance of genuine connection over transactional hustle. Todd dives deep into: Why understanding who you a…

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Why Midlife Is the Perfect Time to Pivot with Beverley Glazer | RR312 30:40

3M ago30:40

30:40

The rules you followed to get here don’t have to be the ones you follow next and that’s where the magic begins. Beverley Glazer, transformational coach and founder of Reinvent Impossible, joined me for a powerful conversation about what it really means to thrive in midlife and beyond. With decades of experience as both a therapist and coach, she he…

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STRATA – The Six Layers of Neurostrategic Influence 24:37

3M ago24:37

24:37

In this episode, Jake unpacks the fresh concept of STRATA, the six-layer framework embedded in neurostrategy that revolutionizes how you communicate and persuade. Far from just another sales acronym, STRATA maps exactly how your prospect’s brain filters trust, emotion, bias, and decision-making in a precise sequence. You’ll learn why most communica…

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The Salary Gap Illusion: Why Going Solo Isn’t as Risky as You Think 16:31

3M ago16:31

16:31

Feeling stuck between your 6-figure corporate salary and the dream of going solo? You’re not alone—and the fear is real. But the risk? It’s not as big as you think. In this Cliff Notes solo episode, Brett breaks down “The Salary Gap Illusion”—why so many GenXers stay stuck in jobs they’ve outgrown, and how to start building your bridge to freedom t…

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Chris Bogue Shares the Secret to Authentic Content That Converts | RR311 43:29

3M ago43:29

43:29

Video isn’t just about showing up—it’s about showing who you really are. I had the opportunity to sit down with Chris Bogue, improv performer, video coach, and creator of The Pattern Breaker. Chris brings a fresh, comedic edge to business videos on LinkedIn, helping people ditch stiff scripts and start making real, human connections through short, …