Aaron Schwartz has built and sold startups, advised 30+ founders, and helped raise millions. Now he’s back in the trenches as co-founder and president of Orita.ai - a platform helping brands fix email deliverability and segment smarter using AI.

In this wide-ranging episode, Aaron opens up about the chaos of early-stage founding, what most people get wrong about go-to-market, and why he’s more focused than ever on building for durability, not just scale.

This is a masterclass for any operator, advisor, or founder figuring out how to go pro without losing their mind.

Jon Laster is a stand-up comic, MC at the Comedy Cellar, and now founder and CEO of Blapp, an app that maps and sells Black-owned businesses.

In this powerful episode, Jon shares how the murder of George Floyd led him to shift gears from punchlines to product-building. What started as an idea during lockdown is now a growing tech platform with real impact: helping Black-owned businesses get discovered, generate revenue, and stay alive.

Jon opens up about what it really takes to build a startup with no traditional tech background, how he convinced names like Chris Rock and Tiffany Haddish to invest, and why he sees comedy as the ultimate founder bootcamp.

This is a conversation about resilience, reinvention, and staying scrappy — no matter how many nights you bomb on stage.

Bobby Shmurda (real name Ackquille Jean Pollard) is a musician, entrepreneur, and cultural force who joins us to unpack his radical transformation from the streets to the boardroom. Best known for his explosive rise in hip-hop and time behind bars, Bobby is now all-in on building wealth, investing in startups, and giving back through hands-on community work.

In this episode, Bobby opens up about how prison gave him the structure to run multiple businesses, why he refuses traditional managers to maintain control, and how he’s applying street smarts to venture capital. He breaks down the moment he got serious about generational wealth, the lessons he learned reading contracts inside a jail cell, and why he proudly calls himself a “pimp nerd” obsessed with equity, margin points, and capital gains.

This is Bobby Shmurda like you’ve never heard him before.

Max Crowley, host of The Early Podcast, joins us to unpack his wild career journey - starting as employee #25 at Uber, launching a mobile-first coffee startup that was later acquired by GoPuff, and stepping into the high-stakes world of startup fundraising and operations at scale.

In this episode, Max breaks down what it was like building Uber’s early operations from the ground up, why scrappy talent always wins, and how Bandit, his app-based coffee shop, pivoted and sold during the height of COVID. He shares what he learned in the trenches as Chief of Staff to GoPuff’s founders, how he thinks about hiring A+ players, and why his new obsession is building in public through storytelling.

He also opens up about imposter syndrome, the art of reinvention, and what it means to stay in the game long enough to find your next thing.

00:00:00 – Introduction: Meet Max Crowley, Host of The Early Podcast

00:03:49 – Reinvention Mode: What Max Learned from Taking a Step Back

00:13:13 – The Invisible Contract: Why Consistency Builds Trust

00:14:21 – Early Days at Uber: Max Was Employee #25

00:23:13 – Uber Began with Just a Text Message

00:40:19 – Founding Bandit: The Idea Behind the App-First Coffee Shop

00:58:49 – Don’t Feel Like a Founder? Go Join a Rocket Ship

01:00:39 – Max’s Turning Pro Moment: Joining Uber at Age 24

Allie Egan, founder and CEO of Veracity, joins us to unpack how her personal health journey led to launching one of the most innovative brands in holistic wellness. After stints in banking, private equity, and high-growth DTC fashion, Allie built Veracity to help people get to the root of their health issues, starting with hormone and biofactor testing.

In this episode, Allie shares the story behind reversing her own Hashimoto’s diagnosis, how she balances building a venture-backed business with raising two kids, and the systemic issues in modern healthcare that inspired her to act. She also dives into practical wellness advice, the business of building trust in supplements, and why education, not hype, is the real growth engine.

00:00:00 – Introduction: Meet Allie Egan, Founder & CEO of Veracity

00:04:04 – The Health Scare That Changed Everything: Diagnosed with Hashimoto’s

00:09:17 – Why Founders Need to Question Everything - Even Their Doctors

00:21:29 – No Such Thing as Balance: How Allie structures work, family, and focus

00:29:35 – Why Wellness Is Broken: A fresh take on preventative health and biohacking

00:37:29 – The Most Overhyped Wellness Trend (and what to do instead)

00:39:21 – Why You Shouldn’t Use Mouthwash (and other gut health surprises)

00:46:09 – From Operator to CEO: The future of DTC and what’s changing in e-commerce

00:51:10 – Why She Runs Marathons: The mindset behind endurance - at work and in life

Ben Buaron, founder and CEO of Windmill Growth, joins us to unpack his incredible leap from Israeli combat officer and aspiring lawyer to running a 7-figure bootstrapped startup in New York City.

In this episode, Ben breaks down how his military background shaped his leadership mindset, what it took to scale Windmill from zero to $1M+ ARR in under a year, and why personal growth became the foundation for business success.

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#EntrepreneurPodcast, #FounderAdvice, #BusinessGrowthTips, #Selfimprovement #Entrepreneurs #BusinessStrategies #PersonalDevelopment #Advice #TurningProPodcast #BenSharf #AdrianAlfieri #Podcast #Founder #Growth

Ben Buaron, founder and CEO of Windmill Growth, joins us to unpack his incredible leap from Israeli combat officer and aspiring lawyer to running a 7-figure bootstrapped startup in New York City.

In this episode, Ben breaks down how his military background shaped his leadership mindset, what it took to scale Windmill from zero to $1M+ ARR in under a year, and why personal growth became the foundation for business success.

00:00:00 – Introduction: Meet Ben Buaron, Founder & CEO of Windmill Growth

00:10:30 – Redefining Purpose: Realizing he had to live life on his own terms

00:13:38 – Moving to NYC: The story behind a one-way ticket and an unexpected roommate

00:16:16 – Windmill Origins: From growth hack idea to full-fledged company

00:17:32 – First Revenue to $1M ARR: How Ben scaled Windmill in under 12 months

00:21:51 – Personal vs Business Growth: The emotional journey behind the numbers

00:24:39 – Turning Pro Moment: Realizing he couldn’t tie his self-worth to revenue

00:26:04 – The 3-Hour Morning Routine: How journaling, prayer, and structure changed everything

00:31:00 – Custom vs Cookie-Cutter: Why self-care should be personalized

00:34:13 – The 2-Day Rule: Ben’s go-to system for staying consistent

00:39:05 – The Accent Myth: Letting go of limiting beliefs around language and sales

00:42:10 – Combat Leadership to Company Culture: Why his employees love building Windmill

00:47:10 – Why Israeli Founders Hit Different: The startup advantage of real-world intensity

00:49:21 – Lessons from War: What the army taught him about staying calm under chaos

00:52:26 – No Such Thing as Failure: How setbacks drive iteration and progress

00:56:29 – Helping Other Men Turn Pro: Why he’s building his next project around personal development

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Learn more about Windmill Growth: https://www.windmillgrowth.com/

Connect with Ben Buaron: https://www.linkedin.com/in/ben-buaron/

Learn more about Turning Pro Podcast: https://www.turningpropod.com/

Subscribe to the weekly newsletter for entrepreneurs: https://turningpropodcast.beehiiv.com/subscribe

Follow Ben Sharf: https://hoo.be/bensharf

Follow Adrian Alfieri: Instagram: https://www.instagram.com/adrian.alfieri/ Twitter: https://twitter.com/adrianalfieri Linkedin: https://www.linkedin.com/in/adrian-alfieri/

#EntrepreneurPodcast, #FounderAdvice, #BusinessGrowthTips, #Selfimprovement #Entrepreneurs #BusinessStrategies #PersonalDevelopment #Advice #TurningProPodcast #BenSharf #AdrianAlfieri #Podcast #Founder #Growth

Jacob Catalano, founder and entrepreneur, knows what it takes to push boundaries in tech and entrepreneurship. After selling his first startup to Snapchat, where he worked on game-changing projects like "My AI", Jacob co-founded Flock*, a product studio revolutionizing content creation with conversational AI. Their flagship product, dubbed an “AI ghostwriter,” helps users express their ideas effortlessly through natural dialogue.

In this episode, Jacob opens up about iterating on startup ideas, building a dynamic partnership with his co-founder, and the lessons from Snapchat that shaped his approach to entrepreneurship. He also dives into early-stage investing, balancing vision with pragmatism, and why persistence is the ultimate tool for success.

*This episode of Turning Pro Podcast was filmed in 2024.

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#EntrepreneurPodcast, #FounderAdvice, #BusinessGrowthTips, #Selfimprovement #Entrepreneurs #BusinessStrategies #PersonalDevelopment #Advice #TurningProPodcast #BenSharf #AdrianAlfieri #Podcast #Founder #Growth

Alex Song, founder and CEO of Proxima, joins us to share his remarkable journey from the high-stakes world of finance to revolutionizing customer acquisition with cutting-edge data intelligence. Drawing from his experience as a DTC brand operator, Alex built Proxima into a transformative platform that helps brands navigate the complexities of the post-iOS privacy landscape.

In this episode, Alex opens up about the emotional highs and lows of entrepreneurship, the key decisions that shaped his leadership style, and the hard-won lessons on resilience. He shares how he inspires his team with a unified vision, maintains momentum through uncertainty, and stays laser-focused on his mission while balancing personal growth with the demands of scaling a groundbreaking company.

Taylor Brandt, newly appointed Partner at Headline, joins us to unpack the nuances of venture capital through the lens of an operator-turned-investor. With a career that spans leading growth at Rockets of Awesome to navigating the challenges of early-stage VC, Taylor brings a wealth of knowledge and practical insights. In this episode, Taylor discusses the shifting dynamics of the VC landscape, the traits of founders who succeed, and the art of balancing portfolio management with sourcing new deals. She also dives into the value of storytelling, the importance of understanding venture capital as an asset class, and the evolving role of infrastructure businesses.*Taylor was a Principal at Headline when this episode was filmed.