The Real Cost of Being an Entrepreneur | Lauren Kleinman

He Left a 6-Year Finance Career to Build an E-Commerce Brand. Here's What Happened.

His parents thought he'd lost his mind. Zach Goldstein had spent six years building a career in finance — the safe path, the one his family understood — when he quit to sell sweatpants. He had zero apparel experience, zero manufacturing contacts, and exactly one conviction: that men deserved pants that actually fit. He spent 18 months perfecting a single product before launching a Kickstarter that would either validate everything or prove his parents right. That product was the Olney Everyday Pant. It became Public Rec. A decade later, he sold it to Noble. But this isn't a story about a lucky Kickstarter. Zach spent ten years navigating inventory nightmares he had no business surviving, hiring the right people at the wrong time, and watching his first retail store — opened on Bleecker Street in November 2019 — get swallowed by a global pandemic five months later. Dead rent. No foot traffic. No plan B. He paid his Facebook ads agency in gift cards for years because cash was too tight to write a check. He learned that delayed gratification isn't a virtue — it's the only skill that separates builders from dreamers. Most founders who sell never talk about what comes after — the strange silence of watching ads for a brand you built but no longer own. Zach did. This is the story of a finance guy who bet on a problem he could feel in his own skin, built a clothing brand from nothing, and walked away. What he built. What it cost. And what it takes to bet on yourself when nobody else will.⸻⸻⸻⸻⸻⸻⸻⸻⸻ 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

He Joined AppLovin at 18 — No Degree, No Background. Here's What He Found.

Rafael Vivas's dad told him the internet was a fad. Then kicked him out of the house for believing otherwise.Rafael was 18 years old — no degree, no safety net, no plan B — when he walked into a startup nobody had heard of and took a bet most people wouldn't have taken at twice the age. He told himself he would die before he let it fail. That startup was AppLovin. Today it's worth over $180 billion.But this isn't a story about being in the right place at the right time. Rafael Vivas was the first salesperson through the door — sleeping on a bunk bed in the office, grinding in a market that was moving faster than anyone could track, inside a company that was one bad quarter from disappearing. He watched AppLovin survive wars with billion-dollar competitors, lose a $1.4 billion acquisition deal, and bet everything on a pivot that shouldn't have worked.Most people who were there still haven't talked about what it was actually like. Rafael did.This is the story of a blue-collar kid who got kicked out of his house at 15, built a digital business before most people knew what that meant, and ended up on the inside of one of the greatest tech comebacks of the last decade. What he saw. What it cost. And what it actually takes to survive a rocket ship from day one.⸻⸻⸻⸻⸻⸻⸻⸻⸻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

How Suja Juice Went From $60M in Debt to a $400M Exit

He was running a nightclub empire when 2008 hit. Checked himself into rehab. Nearly filed for personal bankruptcy. Then he co-founded a juice company in a San Diego kitchen — and scaled it to nearly $100M in revenue.But the real story starts after that.Coca-Cola and Goldman Sachs bought 49% of Suja Juice with a promise to acquire the rest. They met the employees. They started transition plans. Then a new CEO walked in and walked away from the deal — leaving Suja $60 million in debt and hours from bankruptcy.This is the story of James Brennan — a blue-collar kid from Rockaway Beach who built, lost, rebuilt, and then had to do it all over again. The near-death of Suja Juice. The midnight deal that saved it. And the decision to buy Coca-Cola out of his own company before taking it public on NASDAQ.This isn't a founder highlight reel. It's what actually happens when everything is on the line.⸻⸻⸻⸻⸻⸻⸻⸻⸻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

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