Tag: Strategy

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 rebuilding from scratch to ultimately create a sustainable, values-driven business that’s thrived for over two decades. This is a story about resilience, conviction, and what it really takes to build a business from the ground up. --- Episode Resources “The Man in the Glass” by Anonymous (https://allpoetry.com/The-Man-in-the-Glass) “The Man in the Arena” by Theodore Roosevelt (https://www.theodorerooseveltcenter.org/Learn-About-TR/TR-Encyclopedia/Culture-and-Society/Man-in-the-Arena.aspx)

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 or someone curious about investing in early-stage companies, this episode is packed with unfiltered insights you don’t want to miss. --- Episode Resources Marcia’s Podcast: The Angel Next Door (https://www.marciadawood.com/angelnextdoor) Marcia’s Book: Do Good While Doing Well (https://www.marciadawood.com/dogood) “Venture Deals” by Brad Feld & Jason Mendelson: (https://a.co/d/eZTwdZy)

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. --- Episode Resources - “Good to Great: Why Some Companies Make the Leap...And Others Don't” by Jim Collins (https://a.co/d/d13leDe) - “The Contrarian's Guide to Leadership” by Steven Sample (https://a.co/d/bMpm7gr)

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. We discuss his other ventures and what he’s learned along the way about hiring the right early employees, developing a go-to-market strategy, and how to stay true to a vision while adapting to reality. Throughout every topic we cover, Bob shares hard-earned wisdom for founders at every stage. --- Episode Resources Check out what Bob is currently building with his company “Timless Tartans” (https://timelesstartans.com)

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 why social media success isn’t about posting more, but posting smarter. If you’re an entrepreneur looking to build a business that works FOR you, this conversation is packed with a ton of actionable insights you’ll want to hear. --- Episode Resources Keep up with Katie (http://www.katiebrinkley.com) (https://www.instagram.com/iamkatiebrinkley) (https://facebook.com/iamkatiebrinkley) (https://linkedin.com/in/katiebrinkley) Learn More About Next Step Social (https://www.nextstepsocialcommunications.com) Learn More About Katie’s Book, “The Social Shift” (http://www.katiebrinkley.com/book) Listen to Katie’s Podcast, “Rocky Mountain Marketing” (https://www.youtube.com/@rockymountainmarketingpodcast) Tools Discussed In This Episode (https://www.loom.com) (https://toggl.com)

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 nothing without a strong go-to-market strategy. Whether you’re a new founder or a seasoned entrepreneur, this episode is packed with practical advice for building and scaling your product. --- Episode Resources Steal Like an Artist by Austin Kleon (https://a.co/d/1AT07NP)

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 providers. We cover so much in this episode. We break down the myths of building a business, the realities of fundraising, and why running lean is critical in a company’s early stages. There’s a ton in here to chew on, and anyone in the Startup space will take something practical and insightful away from his perspective. --- Episode Resources Check out what Daniel and his co-founder are building at Ravella Health (https://www.revellahealth.com) “Startup Success” by Gordon Daugherty (https://a.co/d/b50Xzn5)

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 believes mental health doesn’t have to be a sunk cost for founders. We dive into the challenges of launching a product in two countries at once, the myths that hold startups back, and how Athlete is planning to navigate data privacy concerns for its customers. Ben’s experience and skillsets are extensive, and I took away so much even from our short time together. You don’t want to miss this one! --- Episode Resources Check out what Ben and his co-founder are building at Athlete (https://lifeathlete.co)

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 through MVPs. He also reveals his process for filtering ideas, fighting distractions, and overcoming challenges in marketing and sales. If you’re ready to launch smarter and faster, this episode is packed with actionable insights you won’t want to miss! --- Episode Resources Check out a few of Martijn’s projects (https://whatpulse.org)(https://mutedeck.com) Atomic Habits by James Clear (https://a.co/d/akrywzm)