Ready, Set, Startup! - Strategies from Founders, Funders, and Beyond

Ready, Set, Startup! - Strategies from Founders, Funders, and Beyond

Let’s pull back the curtain on what really goes down in the Startup world. Every episode offers honest, off-the-cuff chats with founders, investors, analysts, and other Startup insiders as they share the hard-earned wisdom you can't find in a business textbook. We break down the wins, the disasters, the risky bets, and the lessons learned along the way, delivered with zero intimidation and a lot of practical takeaways. If you’re building, dreaming, or just curious about how Startups actually work, you’re in the right place. Ready? Set…let’s get STARTed!

Episodes

Therapy Without Compromise: A Founder’s Fight for Quality Care w/ Doug Polster of Thriving Center of Psychology

October 13, 2025 • 45 mins
Doug Polster was deep into clinical work when a conversation with a former classmate sparked something bigger. What started as a way to keep his private practice afloat during COVID slowly turned into a cross-state mental health network rooted in accessibility and real care. In this episode, Doug unpacks the lessons behind Thriving Center of Psychology’s growth, from sunsetting a failed tech platform to rethinking how founders defi...
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Getting Out of Your Own Way: Unlocking Your Impact w/ Stavros Michailidis

September 29, 2025 • 50 mins
Stavros Michailidis didn’t plan to become a founder. He simply grew up around it. From revitalizing his family’s construction business to landing Fortune 500 clients with an innovation consultancy, his path has been shaped by experimentation, reinvention, and a deep curiosity about what makes businesses actually work. In this episode, he reflects on the difference between an A-plus idea and a B-plus outcome, why most hiring mistake...
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Built to Sell: How to Scale with Exit Intention w/ Ryan Estes of Kitcaster

September 15, 2025 • 38 mins
What if your biggest success came from a total collapse? For Ryan Estes, that moment came when the pandemic wiped out his agency’s entire client list. Instead of folding, he doubled down on a side project—Kitcaster—and turned it into a thriving podcast booking service that would eventually be acquired. In this episode, Ryan opens up about his scrappy start, the mindset shift that fueled his growth, and why building a culture rooted...
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Content is the Cheat Code: an Organic Growth Playbook w/ Steve Young of App Masters

September 1, 2025 • 35 mins
After years of side hustles and self-doubt, Steve Young made one decision that changed everything. He began his entrepreneurial journey selling cassette tapes in grade school, but it wasn’t until he launched a niche podcast about apps that things finally clicked. In this episode, Steve shares how fear nearly held him back, how he landed his first client, and how he built a profitable agency without outside funding. It's a story abo...
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Founder Finances: Wealth, Life, & the Meaning of “Enough” w/ Chris Girbés of Five Oceans Advisors

August 18, 2025 • 53 mins
When Chris Girbés left a steady job to start his own wealth practice, he wasn’t chasing scale. He was chasing meaning. In this episode, he shares what he’s learned from working with startup founders: the myth of the perfect exit, the danger of unclear goals, and the burnout that comes from tying your identity too closely to your business. Whether you're scaling or still scrappy, this conversation is packed with grounded insight on ...
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Building with Purpose: Lessons for the Long Run w/ Erik Stanley of Trail Roots

August 4, 2025 • 46 mins
When Erik Stanley left the comfort of a steady paycheck and the familiarity of a running store, he didn’t just launch a business, he built a movement. In this episode, Erik shares how Trail Roots was born from a desire to coach differently, build genuine community, and carve out space on Austin’s untamed trails. He opens up about the emotional hurdles of breaking ties, the real cost of hiring wrong, the power of purpose, and why ha...
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The Intuition Advantage: Using Gut and Grit to Bet Big and Bounce Back w/ Tom Williams of ELEASE

July 21, 2025 • 54 mins
At just 25, Tom Williams launched his first lending business with $5,000, a dream, and a San Francisco office he secretly lived in. In this episode, Tom walks us through his unorthodox journey from boat-washing teenager to fintech founder, revealing the pivotal moments, early sacrifices, and bets that shaped his entrepreneurial path. He opens up about navigating failure, weathering the dot-com bust from inside Silicon Valley, and r...
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From Long Jump to Leap of Faith: Starting Solo and Scaling Smart w/ Neil Cameron of Sport Works

July 7, 2025 • 40 mins
Neil Cameron’s entrepreneurial journey didn’t start in a boardroom—it started on a beach in Australia after a career in athletics came to an unexpected end. In this episode, Neil reflects on the leap from solo founder to seasoned leader, revealing the struggles of bootstrapping, the power of listening to your customers, and the hard-earned wisdom behind building the right team. With honesty and humility, he shares what it really ta...
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Betting the Farm: Navigating the Risks & Rewards of Family Business w/ Tiffany Bailey of Bayside Sod

June 23, 2025 • 55 mins
When Tiffany Bailey stepped into her family’s sod farming business, she didn’t see herself as an entrepreneur, just someone grinding to get the work done. But nearly two decades later, she’s redefined the company, the culture, and herself as a leader. In this episode, Tiffany shares the raw truth about running and growing a business with family: the trust, the tension, and the tough calls. Hear how she navigated succession, scaled ...
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Can AI Give Our Kids Emotionally Intelligent Friends? w/ Peter Fitzpatrick of Fawn Friends

June 16, 2025 • 37 mins
Can a robot become your child’s best friend? Peter Fitzpatrick thinks so. In this episode, Peter, co-founder of Fawn Friends, shares the personal story that led him to build emotionally intelligent AI companions for kids. From pool party hustles in grade school to raising millions in venture capital, Peter opens up about the emotional challenges of leadership, the power of character-driven products, and why putting truth first migh...
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Elevating an Industry: Empowering the Business of Podcasting w/ Bryan Barletta of Sounds Profitable

June 9, 2025 • 49 mins
What happens when someone who loves being the #2 decides to take the lead? Bryan Barletta, founder of Sounds Profitable, joins the show to talk about his unlikely journey to building one of the most influential organizations in podcasting. From calling out broken systems to creating real solutions, Bryan shares how he’s challenging industry norms, creating momentum without investors, and building a business that lifts the entire sp...
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Validating Your Startup Idea w/ Iñaki Gonzalez of Climatta

June 2, 2025 • 46 mins
Iñaki joins the show to share how he turned a no-code prototype and one powerful ally into his fast-growing climate-tech startup, Climatta. He dives into the power of starting lean, why building with customer feedback is everything, and how trust—not just traction—wins investors. From co-founder dynamics to bootstrapping with nothing but a Figma file and a favor, this is a raw, insightful look at what it really takes to build somet...
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Making Data-Empowered Decisions w/ Lucia van den Brink of Increase Conversion Rate

May 26, 2025 • 46 mins
What if your biggest competition isn’t the market—but yourself? In this candid conversation, Lucia Van Den Brink recounts her journey from coding a webshop at age 11 to leading a thriving CRO agency. She shares what it was like to pause everything during maternity leave, why her first hire failed, and how embracing rejection shaped her entrepreneurial resilience. It’s a powerful exploration of self-doubt, personal values, and redef...
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Inside the World of Deep Tech Investing w/ James Wang of Creative Ventures

May 19, 2025 • 59 mins
How do you spot, then evaluate, the breakthrough technologies of tomorrow? In today’s episode, I sit down with James Wang — a deep tech investor who helps unpack the truths behind venture capital, startup success, and the gritty realities of building frontier technology companies. From founding a startup with his wife to investing in AI, robotics, and synthetic biology, James shares hard-earned insights on what separates funded fou...
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Demistifying Angel Investing w/ Marcia Dawood

May 12, 2025 • 51 mins
Angel investor, author, TEDx speaker, and SEC advisor Marcia Dawood joins me to pull back the curtain on what angel investing really is—and why you don’t need to be a millionaire or a finance expert to get started. She shares what most founders get wrong in their pitch, how to evaluate a startup beyond the hype, and why obsessing over the problem is more important than selling the solution. Whether you’re a founder raising capital ...
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From Bark to Bottle: Reinventing a Caribbean Tradition w/ Ana Bautista of Bayjoo

May 5, 2025 • 40 mins
Ana left a decade-long career in ad tech to build a beverage brand inspired by Mabí — a traditional Caribbean drink brewed from tree bark. In this episode, she shares how nostalgia sparked innovation, how she bootstrapped her way through formulation fails and supply chain setbacks, and what it really takes to launch a CPG product solo. No funding, no co-founder — just grit, Google, and a vision to bring a forgotten flavor to the ma...
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From Collapse to Comeback: How to Learn from Defeat on the Road to Success w/ Ben Brownback of B2Group

April 28, 2025 • 58 mins
After building a fast-growing production company from the ground up, Ben Brownback lost everything—money, team, confidence, and direction. In this episode, he shares the raw, unfiltered story of what really happens when a business collapses, how he found the courage to start again, and why he’ll never build the same way twice. Ben opens up about leadership, failure, fear, and what it means to rebuild smarter the second time around....
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Playing the Long Game: A Masterclass in Building, Scaling, and Exiting w/ Bob Knorr of Timeless Tartans

April 21, 2025 • 48 mins
What does it take to walk away from a $15M term sheet? Bob Knorr did just that — choosing ownership, control, and vision over outside capital. He built that company (then 2 others) with a poignant blend of business sense, ethics, and intuition. In this episode we discuss how he built a medtech company from the ground up, bootstrapped it with creativity (and a Costco credit card), and ultimately exited to a publicly traded company. ...
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Engineering the Shift Your Industry Needs w/ Katie Brinkley of Next Step Social

April 14, 2025 • 54 mins
In today’s episode I sit down with Katie Brinkley of Next Step Social to candidly explore the realities of entrepreneurship—how to price your services, when to hire, and some of the tough lessons learned along the way. We discuss the importance of scaling with intention, and how to use your business to actually create the change you believe needs to happen in your industry. We also dig into years of Katie’s expertise to understand ...
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The Startup Spectrum: Lessons from 200+ Founders w/ Arjun Sharma

April 7, 2025 • 37 mins
In today’s episode I talk with Arjun Sharma, a seasoned product & project manager who’s worked with over 200 founders across a variety of technical industries. Arjun shares invaluable insights from his experience guiding startups through the entire product lifecycle—from idea to market. Discover the key traits successful founders share, the importance of balancing vision with flexibility, and why having the best product means nothi...
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