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The Steve Weiss Journey

Steve Weiss
Pacific Palisades, United States
Los Angeles, United States
Generative Engine Optimization
Palisades Fire
Suja Juice
Chatgpt
S&P 500
Straight Outta Compton
Private Equity
Coca-Cola
Exit & Valuation Multiples
O'shea Jackson Jr.
Gemini
Google
Taxes
Fee-Only Wealth Management
Performance PR
Entrepreneurship
Goldman Sachs

The highest ROI is in helping people win. On this podcast, Steve Weiss shares hard-earned lessons on building businesses, handling pressure, and living with standards.

PublishesTwice monthlyEpisodes10Founded4 months ago
Number of ListenersCategory
Business

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Artwork for The Steve Weiss Journey

Latest Episodes

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 ... more

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 th... more

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... more

YouTube

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 i... more

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... more

YouTube

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. No... more

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-degre... more

Is SEO dead? John Zacharias, founder of Grow Marketing, believes the future is "GEO"—Generative Engine Optimization. In this deep dive, we explore how marketing is shifting from Google to ChatGPT and why your old strategies won't work in the AI era. ... more

YouTube

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Recent Guests

James Brennan
Entrepreneur, hospitality/beverage investor and former Suja collaborator
Suja (investor/partner)
Episode: How Suja Juice Went From $60M in Debt to a $400M Exit
Chapin Newhard
Founder/CEO of 48 North, specializing in buy-side advisory for private equity and portfolio companies
48 North
Episode: Your $1M Business Sells at 2x. Their $10M Business Sells at 10x. Here's Why That Gap Destroys Sellers.
Blake Mycoskie
Founder of TOMS, advocate for social entrepreneurship
TOMS
Episode: Blake Mycoskie Built TOMS, Gave It All Away, and Almost Didn't Make It.
Steve Weiss
Host of The Steve Weiss Journey
Episode: Blake Mycoskie Built TOMS, Gave It All Away, and Almost Didn't Make It.
O'Shea Jackson Jr.
Actor who played his father in Straight Outta Compton
Actor, son of Ice Cube
Episode: O'Shea Jackson Jr. on Playing His Dad & The Moment Everything Changed
Lauren Kleinman
Founder/CEO involved in two agencies (Quality Media and Dreamday); expert in performance PR, influencer integration, and brand partnerships
Quality Media; Dreamday
Episode: The Real Cost of Being an Entrepreneur | Lauren Kleinman
Quan Huynh
Author of Sparrow and the Razor Wire; founder of DeFi Ventures
DeFi Ventures
Episode: 22 Years in Prison Changed This Man Forever
John Zacharias
SEO expert, founder of Grow
Grow
Episode: SEO is Dead? How to Master Generative Engine Optimization (GEO) | Jon Zacharias
Gabriel Shaheen
CEO and founder of Falcon Wealth
Falcon Wealth Planning
Episode: Beating the S&P 500: Tax Loopholes & Wealth Strategy

Host

Steve Weiss
Host guiding the interview and drawing out lessons for listeners from guest stories

Talking Points

Recent interactions between the hosts and their guests.

22 Years in Prison Changed This Man Forever
Q: How did you stay positive in prison when the parole process was harsh and full of setbacks?
Initially it was not easy, but a gradual shift came from reading, therapy, and building groups that connected people, which helped me see a path beyond anger and despair.
22 Years in Prison Changed This Man Forever
Q: What was going through your mind when you were being tried for the death penalty?
I was emotionally disconnected, believing it was life or theirs, and I justified the violence as part of the lifestyle I lived, which showed how far I had fallen from any sense of control or empathy.
The Real Cost of Being an Entrepreneur | Lauren Kleinman
Q: What advice would you give that entrepreneur that's listening to this and saying, hey, Lauren, how do I become like you?
Start with two solid clients, do outstanding work for them to build your reputation, and grow incrementally rather than attempting a massive leap. Focus on delivering passion-driven, high-quality work and let that momentum carry you to more opportunities. Also, decide if entrepreneurship is truly right for you, as it requires sacrifices and a willingness to adapt.
Your $1M Business Sells at 2x. Their $10M Business Sells at 10x. Here's Why That Gap Destroys Sellers.
Q: What are the most common challenges sellers face in private equity transactions?
Misaligned expectations and poor communication early in the process, inaccurate data or due diligence, and choosing the right buyer structure; having the right advisors is crucial to avoid missteps and ensure favorable outcomes.
Your $1M Business Sells at 2x. Their $10M Business Sells at 10x. Here's Why That Gap Destroys Sellers.
Q: What does private equity mean, and who are the typical PE players you work with?
PE firms raise money from limited partners, then invest in private companies with the aim of growing them and exiting at a higher value, typically via added leverage, organic growth, or add-ons; they partner with buy-side advisers like 48 North to source and structure deals.

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Frequently Asked Questions About The Steve Weiss Journey

What is The Steve Weiss Journey about and what kind of topics does it cover?

This show centers on high-stakes entrepreneurship, leadership under pressure, and strategic growth across consumer brands, services, and wealth management. Episodes often feature founders and operators sharing firsthand experiences—from rescuing failed ventures and navigating exits to building agency MOUs, mastering growth through data and partnerships, and balancing purpose with profitability. A notable throughline is practical lessons for scaling, risk management, and long-term value creation, with guests ranging from serial entrepreneurs and investors to marketers and wealth professionals. The format tends to blend personal journeys with actionable takeaways for listeners aiming to build resilient businesses, optimize strategy, and manag... more

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Which podcasts are similar to The Steve Weiss Journey?

These podcasts share a similar audience with The Steve Weiss Journey:

1. Moneywise
2. My First Million
3. Founders
4. Prof G Markets
5. All-In with Chamath, Jason, Sacks & Friedberg

How many episodes of The Steve Weiss Journey are there?

The Steve Weiss Journey launched 4 months ago and published 10 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on The Steve Weiss Journey?

Recent guests on The Steve Weiss Journey include:

1. James Brennan
2. Chapin Newhard
3. Blake Mycoskie
4. Steve Weiss
5. O'Shea Jackson Jr.
6. Lauren Kleinman
7. Quan Huynh
8. John Zacharias

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