Tag: Bootstrapping

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) 

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 define their roles. He reflects on the quiet wins, the tough calls, and what it really means to build with intention. --- Episode Resources “The Confidence Gap” by Russ Harris (https://a.co/d/jbAY54D) 

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)

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 in clarity (not chaos) made all the difference. --- Episode Resources “The Origin of Consciousness in the Breakdown of the Bicameral Mind” by Julian Jaynes (https://a.co/d/8gKcq1r)

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 about persistence, clarity, and the freedom that comes from betting on yourself. --- Episode Resources “Extreme Ownership” by Jocko Willink and Leif Babin (https://a.co/d/e1Wvgug) “Do Things That Don’t Scale” by Paul Graham (https://www.paulgraham.com/ds.html)  EO Fire by John Lee Dumas - A daily podcast featuring interviews with successful entrepreneurs, focused on their journeys, lessons learned, and tactical advice for aspiring founders. (https://www.eofire.com/podcast/)  Smart Passive Income by Pat Flynn - A podcast that explores how to build online businesses and create multiple streams of passive income, featuring strategies, case studies, and personal experiments from Pat Flynn and his guests. (https://www.smartpassiveincome.com/spi/)

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 building a business while you build the life you actually want to live. --- Episode Resources Registered Life Planner (RLP) -  A certification focused on life-first financial planning. (https://www.kinderinstitute.com/rlp-designation/) 

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 having a clear mission is the cornerstone of long-term success. Whether you’re a founder, a runner, or somewhere in between, this is one you don’t want to miss. --- Episode Resources “Start with Why: How Great Leaders Inspire Everyone to Take Action” by Simon Sinek (https://a.co/d/548A9oO)  “Slicing Pie” by Mike Moyer (https://slicingpie.com/) (https://a.co/d/ceQJmgs)  The Dave Ramsey Show by Dave Ramsey / Ramsey Solutions Financial advice podcast covering entrepreneurship, debt, budgeting, and leadership. (https://open.spotify.com/show/5exfRPDNCBHmntEkJrlLmX?si=0e9911336ac64f3f) 

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)

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)