Reuben Levinsohn, professional investor and founder coach behind Exit Quotient Ventures and Flying with Founders, argues that clarity and discipline win. He shares how starting from an “exit first” mindset sharpens founder focus, the early signals he listens for like EQ, leadership quotient, paid pilots, and a clean path to $1M ARR, and when to graduate beyond founder-led sales. We unpack the red flags that kill momentum, practical ways to earn a second meeting, and the founder-wellness routines that keep you in the game. Along the way, Reuben breaks down what he saw in Pavewise and Protein Pints, and how to turn traction into a real go-to-market engine. --- Episode Resources Flying with Founders: Founder Coaching, Meetups, Retreats. (https://www.flyingwithfounders.com/) Flying with Founders Youtube Channel (https://www.youtube.com/@FlyingWithFounders/videos) Reuben’s Venture Capital: Exit Quotient Ventures (https://www.exitquotient.com/) Webinar event series: “Inside the Mind of a VC / Investor” (https://www.flyingwithfounders.com/fwfevents/inside-the-mind-of-a-vc-customer-satisfcation) Pavewise: AI-assisted planning for paving in relation to weather. (https://www.pavewisepro.com/) Protein Pints: High-protein ice cream startup that Reuben angel-backed. (https://proteinpints.com/) Catalina Crunch: Exec talent the Protein Pints founders recruited from. (https://us.catalinacrunch.com/) “Lift Others as You Climb” by Scott D. Idle (https://scottidle.com/ , https://a.co/d/hvRFPYv) “The Founder’s Survival Guide” by Rachel E. Turner. (https://www.thefounderssurvivalguide.com/ , https://a.co/d/8BkG46M)

Jule Salem turned a panicked request to staff 200 call-center reps into the foundation of Salem Solutions. In this episode she shares how “smiling and dialing” became a scalable system, why call centers require highly skilled technical talent, and the playbook she uses to fill high-volume roles without sacrificing quality. You’ll hear her early scrappy origins, the mindset that converts urgent problems into opportunity, and practical tactics for building a staffing agency that lasts. --- Episode Resources Salem Solutions Company Site (https://www.salemsolutions.com/about/)

Dawn Haynes is the CEO of Stardust Studio, a nonprofit accelerator for early-stage tech startups. In this episode, Dawn shares her journey from pioneering transatlantic leisure travel to leading a team focused on helping founders build scalable, sustainable businesses. She discusses the importance of problem-solving, resilience, and embracing feedback, along with the challenges of finding the right co-founders and navigating the world of venture capital. If you're looking for practical advice on building a business and leading with purpose, this episode offers valuable insights from a seasoned entrepreneur. --- Episode Resources University of Toronto Entrepreneurial Self-Assessment (ESA) (https://www.studocu.com/en-ca/u/26265481?sid=01761601462) “Leadership is not about being in charge. Leadership is about taking care of those in your charge.” - Simon Sinek, Start with Why: How Great Leaders Inspire Everyone to Take Action (https://a.co/d/0O5KQLW)  “The Servant: A Simple Story About the True Essence of Leadership” by James C. Hunter (https://a.co/d/e2S0RB4)

Marc and Gina Kalaunin built Healing Hands from a love story into eight thriving clinics. They reveal the scrappy moves that sparked their first surge, the “four clinic wall” that almost broke them, and the systems that protected quality while they scaled across borders. Expect hard-won playbooks on hiring for heart, SOPs that actually stick, and the mindset that kept their marriage strong while the business leveled up. If you are scaling a service brand, this is your blueprint. --- Episode Resources Healing Hands Chiropractic (https://healinghands.com.sg/) “Serenity Prayer” (https://en.wikipedia.org/wiki/Serenity_Prayer) “The Alchemist” by Paulo Coelho (https://a.co/d/3cbwOH5)

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) 

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)

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)

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 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 space. This is a masterclass in clarity, conviction, and community-driven growth. --- Episode Resources Superhuman Email App (https://superhuman.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)

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)