The Steve Weiss Journey

Your $1M Business Sells at 2x. Their $10M Business Sells at 10x. Here's Why That Gap Destroys Sellers.

Most business owners think they understand how private equity works. They don't. A $1M EBITDA business sells at a 2x multiple. A $10M EBITDA business sells at a 10x multiple. That gap isn't random — it's the system. And if you don't know how it works before you walk into a deal, you're already losing.In this episode, Chapin Newhard — founder of 48 North Partners and a former PE buy-side advisor — breaks down exactly what private equity firms look for when they acquire a company, the three things every seller must do before taking a meeting, and why most founders walk into the biggest financial decision of their lives completely blind.This is your business exit strategy masterclass. Whether you're building toward a sale or just starting to think about your company's future, this conversation changes how you see your business's real value.⸻⸻⸻⸻⸻⸻⸻⸻⸻Connect With Me!⸻⸻⸻⸻⸻⸻⸻⸻⸻🎙️ Subscribe for weekly conversations with entrepreneurs who've done it the real way.📩 Newsletter: the-next-chapter-today.beehiiv.com💼 LinkedIn: linkedin.com/in/stevejweiss📱 TikTok: @thesteveweissjourney0

Blake Mycoskie Built TOMS, Gave It All Away, and Almost Didn't Make It.

Blake Mycoskie built TOMS Shoes from a vacation idea into a global movement — 100 million pairs of shoes given away, a company worth hundreds of millions, and a name that redefined what business could be. Then he sold it. And nearly lost everything inside. For almost seven years after the exit, Blake quietly fell apart. No company. No community. No identity. What looked like freedom was actually entrepreneur burnout in slow motion — until he hit a moment where he thought about taking his life. What rebuilt him wasn't a new startup. It wasn't another exit. It was two words on a bracelet. This is the story of what success actually costs — and what one of the most recognized entrepreneurs of his generation is building now that he's finally stopped running from himself.⸻⸻⸻⸻⸻⸻⸻⸻⸻Connect With Me!⸻⸻⸻⸻⸻⸻⸻⸻⸻🎙️ Subscribe for weekly conversations with entrepreneurs who've done it the real way.📩 Newsletter: the-next-chapter-today.beehiiv.com💼 LinkedIn: linkedin.com/in/stevejweiss📱 TikTok: @thesteveweissjourney0⸻⸻⸻⸻⸻⸻⸻⸻⸻Chapters⸻⸻⸻⸻⸻⸻⸻⸻⸻0:00 [https://www.youtube.com/watch?v=vucjpzq2ifk] Intro4:33 [https://www.youtube.com/watch?v=vucjpzq2ifk&t=273s] The moment that almost broke him: Blake on hitting rock bottom after the exit5:29 [https://www.youtube.com/watch?v=vucjpzq2ifk&t=329s] "You are enough" — the bracelet, the wound, and the movement7:06 [https://www.youtube.com/watch?v=vucjpzq2ifk&t=426s] When vulnerability goes both ways11:50 [https://www.youtube.com/watch?v=vucjpzq2ifk&t=710s] Advice for post-exit founders who've lost their purpose21:47 [https://www.youtube.com/watch?v=vucjpzq2ifk&t=1307s] How to build something that actually matters: purpose + profit23:28 [https://www.youtube.com/watch?v=vucjpzq2ifk&t=1408s] Life as a video game: Blake's daily growth mindset26:05 [https://www.youtube.com/watch?v=vucjpzq2ifk&t=1565s] Why empowering your competitors makes you stronger27:12 [https://www.youtube.com/watch?v=vucjpzq2ifk&t=1632s] The case for vulnerability in business and in life29:33 [https://www.youtube.com/watch?v=vucjpzq2ifk&t=1773s] The people behind the mission: Blake on Jill and the Enough org31:31 [https://www.youtube.com/watch?v=vucjpzq2ifk&t=1891s] Blake's #1 concern about the world today: screen time

O'Shea Jackson Jr. on Playing His Dad & The Moment Everything Changed

O'Shea Jackson Jr. had one shot to play his father, Ice Cube, in Straight Outta Compton. In this episode, O'Shea opens up about the crushing pressure of the "Legacy," the moment he thought it was all over, and what his dad never actually asked him to do.What you'll hear: * The grueling audition process for Straight Outta Compton * Why he felt like he was "ruining his life" during filming * His real relationship with Ice Cube (The "No Choice" mentality) * His obsession with the Clippers and life as a "Girl Dad" 🎙️ Subscribe for weekly conversations with entrepreneurs and icons. 📩 Join the Newsletter: the-next-chapter-today.beehiiv.com

The Real Cost of Being an Entrepreneur | Lauren Kleinman

Most entrepreneurs talk about the "win." Lauren Kleinman talks about the trade-offs. From her early days in import-export to leading marketing at Ritual and Scopely, Lauren has been at the center of some of the fastest-growing brands in the world. Now, she's the co-founder of Dreamday and Quality Media, where she’s pioneered a new category: Performance PR. In this episode, we go beyond the "hustle" to discuss the actual strategy behind performance pr, the power of whitelisting marketing, and the personal toll of high-stakes entrepreneurship. What you'll learn: - How performance pr bridges the gap between traditional media and direct sales. - The whitelisting marketing strategy that is driving millions in revenue for top brands. - Why Lauren left a stable VP role to start her own agency. - The "Real Cost" of being an entrepreneur and how to manage the pressure. 🎙️ Subscribe for weekly deep dives into the minds of elite entrepreneurs. 📩 Join the Newsletter for exclusive insights: the-next-chapter-today.beehiiv.comTimestamps:00:00 — Intro: The Real Cost of Being an Entrepreneur 04:15 — The Ritual Story: Scaling a brand from zero 12:30 — What is Performance PR? (The Dreamday Model) 22:45 — The Power of whitelisting marketing and Influencer ROI35:10 — Making the Leap: From VP to Founder Let's connect on LinkedIn:linkedin.com/in/stevejweiss See you next episode! Let's Rock n' Roll

22 Years in Prison Changed This Man Forever

From the streets to a prison cell, Quan Huynh's life took a dramatic turn at just 17 when he was convicted for conspiracy to commit a crime. But that was just the beginning of a darker path that led him to a 15-years-to-life sentence for second-degree murder. For over two decades, Quan navigated the brutal realities of California's toughest prisons, initially embracing a life of crime behind bars. This raw and gripping 30-minute interview dives deep into the pivotal moments that changed everything. Discover how a simple letter and a photo of his young niece shattered his hardened exterior, forcing him to confront his past and the man he had become. Quan shares the harrowing details of his journey, from his first criminal act to finding profound purpose in the most unlikely of places. Today, after serving 22 years, Quan runs a thriving nonprofit, proving that true redemption is possible. This is a story of accountability, self-discovery, and the incredible resilience of the human spirit. Tune in to hear Quan Huynh's unbelievable path from convict to changemaker, and find out how 22 years in prison truly changed him forever. Don't forget to subscribe to the newsletter for more stories just like these: the-next-chapter-today.beehiiv.com Let's connect on LinkedIn:linkedin.com/in/stevejweiss