Ep. 256: From Nuclear Submarines to Financial Freedom: Gary Pinkerton's Wealth Playbook

What does it actually mean to lead with extreme commitment—and to follow through on your word, every single time? In this episode, Will sits down with Steve Farber, founder and CEO of The Extreme Leadership Institute, bestselling author, and one of the most respected voices in leadership development today.Steve's team has helped more than 25 companies earn spots on Best Places to Work lists, and his ideas have shaped leadership conversations far beyond the boardroom. He's the author of six acclaimed leadership books, starting with The Radical Leap, which won Fast Company's Readers' Choice Award and was named one of the 100 Best Business Books of All Time. His book Greater Than Yourself debuted as a Wall Street Journal and USA Today bestseller, and Love Is Just Damn Good Business has been featured everywhere from Wharton Radio to the World Economic Forum. He even teamed up with Twisted Sister's Jay Jay French to write Twisted Business, pulling leadership lessons straight from a career in rock and roll.This conversation comes at a perfect moment—Steve's newest book, The Radical Promise: Mastering the Art of Doing What You Say You Will Do, co-written with leadership legends Jim Kouzes and Barry Posner, launches the very day this episode is being recorded. Will and Rick dig into what it takes to build a culture of real accountability, why "doing what you say" is harder—and more radical—than it sounds, and how love and leadership intersect in ways most business books never touch.You can get Steve's book the Radical Promise here: https://www.amazon.com/Radical-Promise-Mastering-Doing-What-ebook/dp/B0HF4T8DPS/ref=books_amazonstores_desktop_mfs_author_smart_catalog_unrecognized_0?_encoding=UTF8&pd_rd_w=MtBjT&content-id=amzn1.sym.47218010-ccda-4098-a91e-bc39e6d446f4&pf_rd_p=47218010-ccda-4098-a91e-bc39e6d446f4&pf_rd_r=133-2963950-0619343&pd_rd_wg=7Tc5H&pd_rd_r=a368e788-2454-4548-ad09-d063b282ef87Get your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog

On this episode of the WillPower Podcast, Will sits down with co-host Rick Segal and special guest Anya Cheng, Founder & CEO of Taelor, an AI-powered clothing subscription service reimagining how men shop for and wear clothes. Before launching Taelor, Anya spent over a decade in Silicon Valley leading product and growth at companies like Meta, eBay, Target, and McDonald's — including a pivotal role in building Facebook and Instagram Shopping.Anya shares her journey from corporate tech leadership to startup founder, the story behind Taelor's AI-driven approach to personal styling and sustainable fashion, and what she's learned building a company at the intersection of AI, data, and consumer behavior. We also dig into the unique challenges of being a female founder in tech, and how Anya thinks about the future of AI-powered personalization.Whether you're into startups, AI, fashion tech, or entrepreneurship stories, this conversation is packed with insight from someone who's built at scale — both inside big tech and out on her own.Get your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog

In this episode, we welcome Arti Finn, co-founder of Orijin, alongside co-host Rick Segal, for a conversation about reimagining opportunity for individuals impacted by the justice system. Arti shares the story behind founding Orijin in 2014 with a bold mission: creating pathways to living-wage employment for justice-impacted individuals and helping break the generational cycle of incarceration.We dig into how Orijin has become a driving force in correctional edtech — building programming that's now active in 21 states and reaching hundreds of facilities nationwide. Arti discusses the challenges of scaling innovation inside one of the most overlooked corners of the education system, what real workforce readiness looks like for people reentering society, and why this work matters far beyond the walls of a facility.Whether you're interested in social impact, education innovation, or the intersection of business and justice reform, this episode offers a compelling look at what's possible when purpose drives a business model.Get your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog

What happens when getting fired turns out to be the best thing that ever happened to you? For Ramon Ray, it was the spark that launched an entrepreneurial journey most people only dream about.Ramon spent years working a stable job at the United Nations, juggling two young kids and a growing family — until he was let go for being too entrepreneurial. Instead of seeing it as a setback, he took it as a sign. Since then, he's built five businesses, successfully sold three of them, authored five books (including his latest, The Celebrity CEO), and become a go-to voice for small business owners looking to grow without losing themselves in the process.In this episode, Ramon joins us to talk about what it really takes to build a business from scratch — the mindset shifts, the hard lessons, and the proven strategies that separate businesses that survive from those that thrive. We dig into how he balances aggressive growth with actually enjoying life, why simplicity beats complexity when it comes to strategy, and what he's learned from being featured in outlets like Forbes and hosting his own show, The Rundown with Ramon, on the USA Today Network.Whether you're just starting out or already deep in the entrepreneurial grind, Ramon's insights on consistency, team-building, and giving back will leave you with practical takeaways you can apply right away.Tune in for a conversation packed with real talk, hard-won wisdom, and the kind of encouragement every founder needs to hear.Connect with Ramon Ray: ramonray.com | @ramonrayGet your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog

What if you could skip the property altogether and buy the debt instead? In this episode, we sit down with Scott Carson — known throughout the industry as "The Note Guy" — to unpack the world of mortgage note investing.Scott has spent years teaching investors how to buy distressed and performing notes directly from banks, effectively stepping into the bank's shoes. Instead of managing tenants, toilets, and turnover, note investors earn income when a borrower pays — or create profit by restructuring the loan when they don't.We dig into how note investing actually works, the difference between performing and non-performing notes, how to source deals directly from lenders, and why Scott believes this is one of the most misunderstood asset classes in real estate. Whether you're a seasoned operator looking to diversify or a newer investor curious about creative paths into the space, this conversation opens up a side of real estate most people never think to explore.Get your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog

What do commanding a nuclear submarine and building lasting wealth have in common? More than you'd think. In this episode, Rick and I sit down with Gary Pinkerton — a Navy veteran who spent over 30 years as a nuclear submarine officer, including commanding the USS TUCSON, before pivoting into a second career as a Wealth Strategist.Gary opens up about the wake-up call that changed his financial trajectory: losing half his wealth during the 2010 recession. That experience sent him down a path of studying financial strategy in depth, eventually leading him to The Perpetual Wealth Strategy — an approach he now uses to help entrepreneurs, business owners, and real estate investors build certainty and confidence into their financial decisions.We talk about what it's like transitioning from a highly structured military career to entrepreneurship, why so many capable people hesitate to make bold financial moves, and how Gary helps clients get past the fear of "insufficient capital" to actually take action. Whether you're a real estate investor looking to leverage your portfolio, a business owner trying to protect what you've built, or just someone who wants to make smarter financial moves, Gary's perspective — equal parts disciplined submarine officer and empathetic advisor — is one you'll want to hear.Get your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog

What if you could buy and sell real estate without ever walking into a bank? Chris Prefontaine, Chairman and Founder of Smart Real Estate Coach® and 4x best-selling author, has built an entire movement around exactly that. A 3-time Inc. 5000 honoree and former Forbes Business Council Member, Chris has guided his community to hundreds of successful creative finance transactions across North America — and he's breaking it all down on today's episode. We dig into subject-to deals, lease options, owner financing, and why the "terms business" might be the most underrated edge in real estate right now. If you've been waiting on rates to drop before making your next move, this episode will change how you think about the game.Get your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog

What happens when a technology leader who's helped scale a therapy organization from 70 to 180 clinicians decides to build the tool he always wished existed? You get Ambiki — and you get Kevin Dias.Kevin is the founder of Ambiki, an EMR and practice management platform built specifically for pediatric speech, occupational, and physical therapy practices. Before launching Ambiki, Kevin served as CTO at Sidekick Therapy Partners, where he played a pivotal role in growing the organization from 70 to 180 clinicians in just three years. He knows firsthand what it takes to scale a therapy business — the operational chaos, the tech gaps, and the very real cost of using tools that were never designed with pediatric clinicians in mind.In this episode, co-host Rick Segal joins the conversation as Kevin pulls back the curtain on why he built Ambiki from the ground up, what makes pediatric therapy practices uniquely complex to run, and how the right technology can free clinicians to focus on what matters most — their patients. We also get into what it's like to build a U.S.-focused healthcare startup while living in Japan, the lessons he carries from his days as a CTO, and his vision for where pediatric therapy technology is headed.Whether you're a clinic owner, a therapist, or just someone fascinated by the intersection of healthcare and technology — this episode is packed with insight.Get your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog

What does it take for a high-achieving executive to step off the traditional path, relocate to Spain, and build a life of true freedom — without sacrificing success? Billy Keels has done exactly that, and he's made it his mission to help other ambitious C-Level leaders do the same.Billy is a national bestselling author, the host of the top 1% globally ranked podcast Going Long, and an executive-level coach who works with driven leaders ready to grow beyond the boardroom. With a background in corporate leadership and real estate investing, Billy brings a rare combination of real-world experience and strategic clarity to every conversation.In this episode, we dig into what it really means to lead at the highest level — not just professionally, but in life. Billy shares how he helps C-Suite executives break through the invisible ceilings they've unknowingly built, why so many high performers are quietly unfulfilled, and the mindset shifts that change everything. Plus, we talk real estate, building wealth with intention, and what life looks like when you design it from the outside in — from sunny Spain.If you're ambitious, driven, and ready for more, this one's for you.Get your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog

Jon Ostenson has seen both sides of the business world — 15 years climbing the corporate ladder, including a VP of Sales role at Carter's overseeing $350M in revenue, and then a full pivot into franchising. Now, as Founder of FranBridge Consulting and a top 1% franchise consultant in the US, Jon spends 90% of his time helping everyday people discover the freedom and wealth that come with owning the right business. In this episode, we dig into how to evaluate franchise opportunities, what most people get wrong before buying in, and why non-food franchises might be your best-kept secret.Download his book 'Non-Food Franchising' here:https://franbridgeconsulting.com/#contact Get your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog