Tag: Early-Stage

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) 

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 mistakes start with ego, and what it means to build something because it matters, even if it never scales. --- Episode Resources “The Surrender Experiment” by Michael A. Singer (https://a.co/d/0OPRKar)  “The Aspirational Investor” by Ashvin B. Chhabra (https://a.co/d/4zw97dQ)

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)

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 takes to grow a business—and yourself—along the way. --- Episode Resources The E-Myth by Michael E. Gerber (https://a.co/d/2ARcl6J)

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 might be the most underrated startup strategy. If you’ve ever questioned whether you’re crazy to dream this big, this one’s for you. --- Episode Resources Stay up to date with what Peter and his team are building (https://www.fawnfriends.com) Learn more about Vernon Howard (https://www.anewlife.org)

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 redefining success on your own timeline. --- Episode Resources Get more info on Lucia’s company (https://increase-conversion-rate.com)

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 founders from the rest, why the best product doesn’t always win, and how momentum — not just money — makes or breaks a startup. Whether you’re pitching, investing, or just curious about how it all really works, this conversation offers valuable perspective from a thought-leader in the niche but fascinating world of deep tech investing. --- Episode Resources Subscribe to James’ Blog (https://weightythoughts.com) Get more info on Creative Ventures (https://creativeventures.vc)

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)

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 ever wondered how to get involved in startup investing—or how to avoid the biggest mistakes—this episode is for you. --- Episode Resources Keep up with Kelly (https://www.linkedin.com/in/kelly-iannone-waypointcip)