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Healthy Founders, Healthy Exits: The Human Side of Startup Success w/ Reuben Levinsohn of Washington Advisors & Ventures
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)
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Serve First, Scale Second: How to Turn Passion Into Purpose w/ Marc & Gina Calaunan of Healing Hands
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.
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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)
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Therapy Without Compromise: A Founder’s Fight for Quality Care w/ Doug Polster of Thriving Center of Psychology
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
“The Confidence Gap” by Russ Harris (https://a.co/d/jbAY54D)
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Building with Purpose: Lessons for the Long Run w/ Erik Stanley of Trail Roots
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.
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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)
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From Bark to Bottle: Reinventing a Caribbean Tradition w/ Ana Bautista of Bayjoo
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.
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Episode Resources
Try some Bayjoo! (https://bayjoo.com)
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