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
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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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March 31, 2025 • 41 mins
What do successful entrepreneurs have in common? They ask the questions no one else is asking. Today, I sit down with Daniel Yeboah—founder, problem-solver, and challenger of the status quo. From his first paper route to successfully exiting multiple startups, Daniel has always seen opportunities where others see roadblocks. Now, he’s tackling one of the toughest industries—healthcare—with AI-powered, real-time insights for provide...
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March 24, 2025 • 65 mins
“Eyelids are gross—people should wash them.” That’s the message that today’s guest, Tom Chapman, is on a mission to share with the world. In our interview, we talk about how his experience as a serial entrepreneur is helping him tackle a problem most of us don’t even realize we have. Dry eye disease is exploding, thanks to our screen-heavy lifestyles, and yet almost no one is doing anything about it. Tom and his co-founders started...
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March 17, 2025 • 38 mins
What if life insurance didn’t just protect you financially but actually helped you live longer? In this episode, we sit down with Ben Mason, co-founder and CEO of Athlete, a startup that’s disrupting the insurance industry by pricing based on fitness, instead of based on risk level. Ben shares his journey from advertising to entrepreneurship, the hard lessons he learned about chasing ideas vs. listening to customers, and why he bel...
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March 10, 2025 • 42 mins
In today’s episode I talk with Kelly Iannone, an experienced full-time investor who’s built a diverse portfolio across real estate, public stocks, and most recently, early-stage startups. She shares why one of the biggest misconceptions about investing is that you have to do it all yourself, how to spot a founder worth betting on, and why trusting the right people is the real key to hedging risk and achieving 10x returns. If you’ve...
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In today’s episode I talk with Martijn Smit, a serial entrepreneur who’s mastered the art of rapidly getting new products to market. Martijn shares his journey from early coding experiments to building multiple startups, including how he balances efficiency with perfection. We dive into why shipping fast beats waiting for the product to be fully-baked, the myth of “if you build it, they will come,” and the power of testing ideas th...
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