Tag: B2B

What happens when you jump into entrepreneurship without a co-founder and without a safety net? Vijay Rajendran has done just that, and more. In this episode, he shares his journey from launching Hungry Globetrotter to leading digital innovation at global banks and advising hundreds of startups. We dig into the emotional weight of solo founding, the value of structured support, and why your “path to moat” matters more than having one on day one. Vijay also talks about his approach to hiring, staying in your zone of genius, and increasing your surface area for opportunity. Packed with practical wisdom and honest reflections, this one is for anyone building from zero to one. --- Episode Resources “The Hard Thing About Hard Things” by Ben Horowitz (https://a.co/d/5sivXFO)  “Zero to One” by Peter Thiel (https://a.co/d/8q4Dut7)  “Venture Deals” by Brad Feld and Jason Mendelson (https://a.co/d/brj0OO0)  “How Will You Measure Your Life?” by Clayton Christensen (https://a.co/d/8l6kqb7)  “Never Split the Difference” by Chris Voss (https://a.co/d/ir3M1YX)  “The Funding Framework” by Vijay Rajendran (https://a.co/d/7szE3tu)  “The Illusion of Invincibility or Why Cannons > Moats” article by Vijay Rajendran (https://open.substack.com/pub/startupsystem/p/the-illusion-of-invincibility-or?r=1z3bi1&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false) 

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 the business, embraced B2C, and built a culture rooted in clarity and care. This is a masterclass in leadership, learning, and legacy. --- Episode Resources Check out what Tiffany is building at Bayside Sod (https://baysidesod.com) Read more about the Full Focus Planner (https://fullfocusstore.com) Learn more about the Culture Index (https://www.cultureindex.com)

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 something that matters. --- Episode Resources “Only the Paranoid Survive” by Andrew Grove (https://a.co/d/acCH658) “Predictable Revenue” by Aaron Ross (https://a.co/d/iFC7efW) “The Mom Test” by Rob Fitzpatrick (https://a.co/d/drMFDyi) “Crossing the Chasm” by Geoffrey Moore (https://a.co/d/9tq5mlq)

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 mainstream. --- Episode Resources Try some Bayjoo! (https://bayjoo.com)

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)

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)

“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 Peeq Pro to address the issue by revolutionizing eyelid hygiene. We dive into what it takes to build a business in an industry that’s still waking up to its own problem, the hard truths of entrepreneurship, and why taking bigger swings is the key to real impact. Tom transparently shares invaluable perspective on everything from starting a company with your spouse, to navigating the challenges of building hardware vs. software. There’s something here for everyone. Let’s dive in! --- Episode Resources Check out what Tom and his co-founders are building at Peeq Pro (https://peeqpro.com)

In today’s episode I talk with Tom Griffiths, co-founder of Gale Payments, as we uncover the realities of startup life and accelerators. Tom shares his journey through multiple ventures, including lessons learned from building without customers, balancing speed with craft, and why accelerators like Techstars were crucial for his company’s growth. He dives deep into the power of networks, the importance of traction when applying, and how founders can overcome common pitfalls. Whether you’re considering an accelerator or just curious about the startup process, this episode is packed full of valuable insights anyone can learn from. --- Episode Resources Check out what Tom and his co-founder are building at Gale Payments (https://www.withgale.com) The Underdog Founder by Adrezio de la Cruz (https://a.co/d/gD2GnaI) The Founder University "Pre-Accelerator" Course by Jason Calacanis (https://www.founder.university)