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.

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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.

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Episode Resources

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.

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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 Calaunan 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.

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Episode Resources

Cheryl Kellond has built startups from the ground up, survived the crash of a hardware business, raised millions in venture capital, and walked away with battle scars. In this episode, she pulls back the curtain on what it really takes to lead a company through chaos. We get into why hiring fast can backfire, how funding can trap you, and what founders often overlook when chasing growth. Cheryl talks candidly about ignoring her gut, managing burnout, and staying true to the reason she started in the first place. It’s a sharp, honest look at the difference between building a business and building one that lasts.

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Episode Resources

“The Hard Thing About Hard Things” by Ben Horowitz (https://a.co/d/9j9DMya) 

Tyler Denk’s Beehiv Newsletter (https://www.beehiiv.com/blog/newsletter-behind-the-scenes) 

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.

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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.

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Episode Resources

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.

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Episode Resources

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.

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Episode Resources

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.

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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/)