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WillPower Podcast

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Rating
★★★★★
5
from
37 reviews
This podcast has
267 episodes
Language
English
Explicit
No
Date created
2019/05/31
Latest episode
2026/11/02
Average duration
36 min.
Release period
11 days

Description

Introducing the WillPower podcast, hosted by a young author and accredited businessman, Will Holdren. Each week, he sits down with some of the top entrepreneurs in the industry to discuss their journey to success, the challenges they faced, and the insights they've gained along the way. From startups to Fortune 500 companies, Will delves into the stories of entrepreneurs who have made a significant impact in their field. Join him as he explores the mindset, strategies, and experiences of the most successful business leaders of our time.

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Podcast episodes

Check latest episodes from WillPower Podcast podcast


Ep. 267: The Unshackled Owner: How Entrepreneurs Build Wealth Without Being Trapped by Their Business, with Aaron Scott Young
2026/11/02
On this episode of the WillPower Podcast, Will sits down with Aaron Scott Young, Chairman and CEO of Laughlin Associates. Over 50 years, the firm has helped more than 200,000 entrepreneurs start, grow and protect their businesses. Aaron has spent more than four decades in the trenches with business owners, and he’s built several multimillion-dollar companies of his own. He started his first business at 18: a recycling company in Portland that he grew to 5,000 customers and sold. Aaron explains why protecting what you’ve built matters as much as growing it. He covers how real estate investors and business owners should think about entity structure, asset protection and keeping their personal wealth separate from business risk. He also shares the thinking behind The Unshackled Owner, his program for helping owners stop being trapped by their businesses and start running them on their own terms. Whether you own one rental property or are building a portfolio or a company, this conversation will change how you think about structuring and protecting your wealth. https://laughlinusa.com/ 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
Ep. 266: Selling Wine Country: Napa Valley Real Estate, Resilience and Writing Your Story with Michelle Wagner
2026/10/30
On this episode of the WillPower Podcast, Will sits down with Michelle Wagner, a Napa Valley Realtor and published author of several books. Michelle has built her career in one of the most distinctive real estate markets in the country, where vineyard estates, wineries and luxury homes all trade hands, and she’s seen firsthand what it takes to serve buyers and sellers when the stakes and the expectations are high. Michelle shares how she built her business in wine country, what makes Napa Valley real estate different from almost anywhere else, and how resilience and a clear sense of purpose have shaped her career. She also talks about becoming an author: why she wrote her books, what she hopes readers take from it, and how telling her story has strengthened her business. Whether you’re an agent, an investor or someone looking to build a career with meaning, this conversation is full of practical lessons and inspiration. https://www.theagencyre.com/agent/michelle-wagner 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
Ep. 265: Eat the Pudding First: Building, Scaling & Exiting 30+ Companies with Gary Ashworth
2026/10/25
What does it take to start a business at 21, take it public, and sell it for a tenfold return before turning 40? In this episode of the WillPower Podcast, Will sits down with British serial entrepreneur, investor, and mentor Gary Ashworth, who has founded or backed around 30 companies across recruitment, healthcare, and property in the UK and Dubai. Gary walks through his path from accountancy recruitment in London at 18 to founding Abacus Recruitment, floating it on the London Stock Exchange, and selling it. He then built and sold the tech staffing firm InterQuest Group, and today he chairs Albany Beck Consulting. He also shares the core ideas from his Amazon bestseller Eat the Pudding First: why failure is a feature rather than a flaw, how to think about exit strategy from day one, and why there’s rarely an unachievable goal, only an over-ambitious timeline. Whether you’re launching your first venture, scaling a real estate business, or planning your eventual exit, this conversation is full of hard-won lessons from someone who has done it again and again. 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
Ep. 264: Build a Sales Team That Doesn't Need You | Marcus Chan, Venli Consulting
2026/10/05
Most founders hit the same wall: every deal still runs through them. In this episode of the WillPower Podcast, I sit down with Marcus Chan, founder of Venli Consulting, a sales training and revenue consulting firm whose 700+ clients have generated over $950 million in revenue. Marcus specializes in helping CEOs build sales teams that can run without them, so the business keeps growing even when the founder steps back. We break down why founder-led sales eventually caps your growth, what it takes to hire and train people who can close without you, and how to build systems that make revenue predictable instead of personality-driven. Whether you're raising capital, scaling a portfolio, or running any business where you're still the top salesperson, this conversation will show you how to get out of the weeds and into the CEO seat. 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
Ep. 263: Keeping Our Nation's Promise: Honoring Veterans with Chris Meek & Dave Jarecki
2026/09/28
This week, Will and co-host Rick Segal sit down with Chris Meek and Dave Jarecki, the duo behind the new book Keeping Our Nation's Promise. Chris spent more than 30 years in finance, including time at Goldman Sachs, before turning his focus to service. He is now CEO of Soldier Strong, a charitable organization that uses medical technology to help American veterans take their next steps forward. He also founded the 9/11 Foundation, a nonprofit that honors the memory of those lost on September 11th. Dave has been a ghostwriter since 1999 and helped Chris bring this story to the page. We talk about Chris's move from Wall Street to philanthropy, the mission behind Soldier Strong and the 9/11 Foundation, and what it takes to turn a life's work into a book. We also get into what our country owes the people who have served it, and how business leaders can use their experience to make an impact that lasts. 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
Ep. 262: Launching Hotels the Smart Way – Kyle Fugatt on STRs, Boutique Hospitality & $30M in AUM
2026/09/23
On this episode of the WillPower Podcast, Will sits down with Kyle Fugatt, founder of Hotel Launch and a short-term rental and boutique hotel operator with over $30 million in assets under management. Kyle has built his business at the intersection of hospitality and real estate, both operating his own properties and coaching investors on how to launch and scale their own boutique hotels. Kyle breaks down what separates a profitable STR from a struggling one, why boutique hotels are drawing more investor attention, and the key steps to moving from single-unit rentals to full hospitality assets. Whether you're running your first Airbnb or eyeing a small hotel conversion, this conversation is packed with practical insight on operations, guest experience, and building a hospitality portfolio that lasts. https://www.hotel-launch.com/ 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
Ep. 261: Extreme Leadership: A Conversation with Steve Farber
2026/08/28
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-d063b282ef87 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
Ep. 260: From Big Tech to Big Fashion: Anya Cheng on Building Taelor
2026/08/17
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
Ep. 259: The Orijin Story: Turning Incarceration into Opportunity
2026/08/17
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
Ep. 258: Five Businesses, Three Exits: Ramon Ray's Playbook for Small Business Success
2026/08/02
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 | @ramonray 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
Ep. 257: Becoming the Bank: Scott Carson on Buying Mortgage Notes Instead of Property
2026/07/12
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
Ep. 256: From Nuclear Submarines to Financial Freedom: Gary Pinkerton's Wealth Playbook
2026/07/06
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
Ep. 255: Terms, Not Banks: How Chris Prefontaine Built a Real Estate Empire Without Traditional Financing
2026/06/29
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
Ep. 254: From CTO to Founder: How Kevin Dias Is Revolutionizing EMR for Pediatric Therapy Clinics
2026/06/08
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
Ep: 253: Beyond the Boardroom: Billy Keels on Coaching Ambitious Leaders to Think Bigger and Live Freer
2026/06/08
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

Podcast reviews

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5 out of 5
37 reviews
★★★★★
diasks2 2026/06/09
Great interviewer
Will does a great job of asking questions that help bring to light the stories that have led entrepreneurs on their paths. Highly recommend his show.
★★★★★
Giuseppe Grammatico 2026/06/03
Great conversation and real value
I really enjoyed being on the WillPower Podcast. Will does a great job making the conversation feel natural, thoughtful, and easy to follow. He comes ...
★★★★★
bigmickeyvits 2026/02/12
excellent host
was just interviewed on Will’s podcast. I loved the structure of the show, the conversational nature, the ability to answer a question thoughtfully an...
★★★★★
QuestFusion 2025/11/24
Packed with Info and Insights
I really enjoyed my interview on the WillPower podcast and found Will to be well informed, prepared, and insightful. He has a great style, and has som...
★★★★★
@Yamz 2024/12/16
Amazing platform
Love this podcast! If you are an entrepreneur or aspiring you will feel right at home here
★★★★★
Doty Rock 2021/10/29
Motivating and insightful!
WillPower is a must listen for anyone involved in sales or entrepreneurialism. Will interviews accomplished business leaders from across the country i...
★★★★★
In Rhythm Sports Podcast 2021/03/10
Willpower | mindgrowth
Really inspired me to do something with my life. Great content. Recommend highly. Great listen
★★★★★
TBarrz 2021/03/06
TBarrs review
The inspiration and insight that your program platform offers is very valuable on a personal growth and self developmental level. Obtaining the knowl...
★★★★★
Alex Sanfilippo | PodMatch.com 2021/03/03
Will brings the right CEOs!
Will does a great job bringing on the guests we all want to hear. Great conversations! A+
★★★★★
IsaacTheGreat@12345 2021/02/25
Great Podcast!
Truly incredible podcast. Sensational in scope and depth. The points outlined in each episode seem to build and develop further in subsequent ones. Wh...
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