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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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Inside the Entrepreneurial Mind: What Successful Founders Do Differently w/ Dawn Haynes of Starter Studio
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)
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Can AI Give Our Kids Emotionally Intelligent Friends? w/ Peter Fitzpatrick of Fawn Friends
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.
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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)
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Demistifying Angel Investing w/ Marcia Dawood
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.
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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)
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The Truth About Early-Stage Investing w/ Kelly Iannone
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.
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Episode Resources
Keep up with Kelly (https://www.linkedin.com/in/kelly-iannone-waypointcip)
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