Your Startup Soundtrack
From breakthrough moments to hard-earned lessons, every Ready, Set, Startup! episode has actionable insights you can use to fund, build, scale, operate, or exit your startup. Start exploring the archive and find fresh perspectives that move you forward.
Episodes
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How Data-Informed Structure Can Turn Chaos Into Scalable Growth w/ Marcio Goncalves of WiseVAs
Marcio Goncalves, founder of a fast-growing virtual assistant agency (a team that handles admin and day-to-day tasks for busy founders) and a fully remote podcast production company, argues that scale comes from structure, not luck. He shares how his first taste of entrepreneurship started at 12, raising pet-store hamsters and finding homes for the new litters, and how that early instinct evolved into launching a podcast in 2012 before most people knew what a podcast was. He walks through leaving a steady salary after a quick real estate win, then building toward the businesses he runs today, including a virtual assistant company growing 10 to 15 percent month over month. We unpack how he turns getting new customers into simple math, the hiring order that helps founders stop being the bottleneck, and the kitchen-table low point that pushed him to adopt the Entrepreneurial Operating System framework plus personality assessments to steady the team and the metrics.
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Episode Resources
• EOS (Entrepreneurial Operating System) – A simple operating framework for running a business with clear priorities, weekly meetings, and a few key numbers to track. (https://www.eosworldwide.com/what-is-eos)
• “Traction” by Gino Wickman (https://a.co/d/3Ox5Q9d)
• Ninety – An EOS software (https://www.ninety.io/)
• Culture Index – A personality tool mentioned for hiring and team alignment. (https://www.cultureindex.com/)
• The Predictive Index, PI Behavioral Assessment – A personality tool for understanding how people are wired at work. (https://www.predictiveindex.com/assessments/behavioral-assessment/)
• Gatekeeper for Spark Mail – Screens and blocks senders to keep inbox clean. (https://sparkmailapp.com/features/gatekeeper)
• “The E-Myth Revisited” by Michael E. Gerber (https://a.co/d/11bO4lH)
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Simplicity Wins: Inside the Mind of a Professional Investor w/ Matthew Stafford
Matthew Stafford, professional investor and co-founder of Nine Others, argues that simplicity wins. He shares how starting on the Venture Capitalist side sharpened his founder’s empathy, the early signals he listens for, and how one dinner became a global peer network. We unpack the pre-boom London fundraising scene, practical ways to cut noise from your pitch, and the community mechanics that actually move founders forward.
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Episode Resources
– Nine Others – Official Website (co-founded by Matthew Stafford) (https://9others.com/)
– “What’s Keeping You Up at Night?” by Matthew Stafford & Katie Lewis (https://a.co/d/hMhyJBI)
– Overview of Matt & STAFFORD VC (https://www.stafford.vc/?pvs=143)
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Finding Your Funding Fit w/ Cheryl Kellond of Play Money Studios
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)
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When Core Values Beat Venture Capital: Building a Bootstrapped Business w/ Jesse Mecham of YNAB
Jesse Mecham, former accountant and creator of You Need A Budget, argues that your real money problem is worry, not math. He shares how a tiny spreadsheet he built to fix one household cash crunch became a calm, profitable business, and what he learned from building his software and methodology: YNAB (You Need A Budget) at night while working full time, botched early hires, and the moment he stopped playing small. We unpack the myths around raising money, co founders, and five year plans, how to grow slowly on purpose without feeling behind, and practical ways to feel in control of your money again. Along the way, Jesse shows how changing your relationship with money can reshape how you think about risk, work, and the life you are building.
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Episode Resources
You Need A Budget (YNAB) – Jesse’s budgeting software and methodology that he created. (https://www.ynab.com)
True Alignment: Linking Company Culture with Customer Needs for Extraordinary Results, by Edgar Papke. (https://www.truealignment.com/true-alignment/)
“Antifragile: Things That Gain from Disorder” by Nassim Nicholas Taleb. This book speaks about how systems and people can benefit from volatility and stress.(https://a.co/d/hWw7TJW)
“Titan: The Life of John D. Rockefeller, Sr.” by Ron Chernow. (https://a.co/d/gUs7qXn)
“Washington: A Life” by Ron Chernow. (https://a.co/d/bzkS3F0)
“Goals! ” by Brian Tracy. This book is a classic goal-setting and personal development book. (https://a.co/d/9wnWUi4)
“Rich Dad Poor Dad” by Robert Kiyosaki. A Personal finance book. (https://a.co/d/aSFlfOq)
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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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Smiling, Dialing, and Scaling: Building a Staffing Agency for Call Centers w/ Jule Salem of Salem Solutions
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
Salem Solutions Company Site (https://www.salemsolutions.com/about/)
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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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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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The Founder’s Focus: Culture, Capital, & Conviction w/ Vijay Rajendran of Startup System
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)
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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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