Beyond A Million

Dan Brisse won back-to-back X Games gold medals as one of the most dangerous urban snowboarders on the planet—jumping off parking garages, rooftops, and rails for a living. But while he was at the peak of his career, he was watching his heroes lose their homes, their wives, and their minds.

So he did something different. He started investing.

In this episode, Dan breaks down how he went from living on peanut butter and jelly sandwiches to co-founding Granite Towers—a real estate company that manages nearly $500M across 3,300+ apartment units. We get into how he protects downside in every deal, why multifamily real estate quietly compounds wealth, and what his exact investing criteria looks like today.

We also get into hiring on core values, why urgency is a red flag in any investment, and the one piece of advice he's giving his 13-year-old son about building wealth.

Key Takeaways with Dan Brisse

(00:00) Intro (02:25) From Gold Medals to $500M AUM

(02:41) The Snowboard Lesson That Saves Him Millions

(03:40) His Mental Checklist Before a Crazy Jump

(06:10) How Risk in Sports Translates to Real Estate

(9:15) Why Most Pro Athletes Go Broke

(14:19) Why Losing Is the Best Motivator

(16:51) The Passive Income Mindset Shift

(20:10) From Duplex to Real Estate Empire

(24:39) Lessons in Real Estate Investing

(35:56) Understanding Cap Rates & NOI

(41:43) Criteria for Evaluating Real Estate Deals

(49:40) Analyzing Real Estate Submarkets

(53:45) What to Look for in a General Partner

(58:43) How to Attract A-Players

(01:04:47) Business With a Purpose

(01:07:12) The #1 Habit Every Pro Athlete Needs

(1:08:26) Advice to New Entrepreneurs

(1:09:32) Would He Do It All Over Again?

Watch on YouTube: https://youtu.be/5E1FQNZDPWM

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I'm sitting down with Jonathan Ronzio, who scaled Trainual from an idea to $30M ARR—while building a company known for its culture and still finding time to climb mountains, run marathons, and live a full life outside of work.

What stood out to me in this conversation is how intentional he's been about building systems—not just in the business, but in his life. We talk about why most founders document the wrong things early, how structure actually creates freedom, and how AI is completely reshaping how companies build, sell, and operate.

We also get into how he thinks about balance versus alignment, what changes (and what doesn't) after raising capital, and why the most defining moments in business are usually the ones you never planned for.

If you're trying to scale without becoming consumed by your business, there's a lot here worth paying attention to.

Key Takeaways

(00:00) Introduction

(01:28) Summiting Aconcagua vs Closing a Series B

(03:01) What Is Trainual and Why It Exists

(03:52) The #1 Thing SaaS Founders Document Too Late

(04:59) When to Create Company Core Values?

(06:48) Why Structure Actually Creates Freedom

(09:57) Which Processes Deserve SOPs?

(11:43) How AI Transformed Trainual's Product Roadmap

(15:16) Will AI Kill SaaS? His Honest Take

(18:49) Figure Out How to Disrupt Your Business

(20:38) Agentic AI and the New Outbound Playbook

(22:34) The Exact AI Tech Stack His Team Uses

(26:05) Data Security in the Age of AI (30:11) $400K in Credit Card Debt for FB Ads

(32:27) Balance vs. Alignment

(34:31) Why Daymond John Joined the Cap Table

(38:05) Cultural Practices That Actually Work (39:48) Project Management & Communication Tools

(43:36) How to Define Culture at Scale

(46:30) Mountaineering Lessons That Made Him a Better Leader

(53:08) Living an Adventurous Life

(58:50) Obsessive Compulsive Creative Disorder

(59:43) Advice for Founders Torn Between Focus and Exploration

Watch on YouTube: https://youtu.be/q17qPXHSEC0

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You don't need to create demand if demand is mandated.

That's the insight Will Caldwell used to build and sell his company.

Will discovered that inside the mortgage industry, banks are legally required to buy flood certificates on every loan. So, he started Snap — a platform that makes it faster and cheaper for banks to do exactly that.

Then he partnered with Intercontinental Exchange, the $95 billion company that owns the New York Stock Exchange, plugged into their existing infrastructure, scaled quickly, and eventually sold 51% of the company for 10x.

In this episode, we break down how to build within regulated industries, tap into existing demand, and scale without chasing customers.

Key Takeaways

(00:00) Small Teams Beat Large Companies

(01:52) Why "Fat Cats Don't Hunt"

(03:13) Starting His First Tech Company

(06:09) Knowing When to Shut Down a Business

(06:51) Turning a $100 Compliance Headache Into a Startup

(09:03) Finding Opportunity in Regulated Industries

(16:58) AI Underwriting

(21:09) Scaling via Strategic Partnerships

(24:00) Selling 45 Banks in One Month

(30:56) Selling to Intercontinental Exchange for 10x

(32:31) Why He Sold Only 51% of the Company

(36:10) Don't Build the Tech Until You Have THIS

(37:44) What Post-Exit Life is Like

(38:41) What Will is Investing In Right Now (40:00) Advice for Entrepreneurs Starting Today

(40:27) Books That Have Shaped His Thinking

Watch on YouTube: https://youtu.be/UmihuBdZByU

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Today I'm talking with Chris Taylor, an entrepreneur who turned a consulting engagement with Nissan into a software company serving half the automotive industry—then sold the business for multiple eight figures without ever raising outside capital.

In this conversation, Chris shares how a consulting project with Nissan became the foundation of his company, how that journey ultimately led to an acquisition, and the earn-out lessons every founder should understand before selling their business.

We also talk about building culture, why founder communities like YPO and EO can accelerate growth, and how AI is changing the economics of software and services.

Key Takeaways with Chris Taylor

(00:00) Intro

(01:23) Bootstrapping vs Venture Capital

(02:17) Is Every Growth Stage Equally Hard?

(04:26) Why Founder Communities Change Everything

(09:41) Is SaaS Dead in the Age of AI?

(12:30) Why Outcome-Based Billing Could Kill SaaS Seats

(15:28) How Chris Got Nissan to Fund His Next Startup

(23:09) Turning Consulting Into a Scalable Product

(33:11) Why Everything in Business Is Negotiable

(40:43) The Real Path to Getting Acquired

(48:30) Building Culture in an Unconventional Office

(59:20) Earn-Out Lessons Every Founder Should Know

Watch on YouTube: https://youtu.be/Vca63g-kq7k

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Today I'm talking to Dan Demsky, who turned the frustration of trying to pack light while traveling into an 8-figure e-commerce business.

He discovered that merino wool clothing lets you pack far fewer items for a trip. The problem was, most of the brands were focused on outdoor gear—not something everyday travelers would actually wear.

So Dan and his buddies built Unbound Merino, a fully remote apparel brand doing $32M a year.

In this episode, you'll hear how they used crowdfunding to validate product-market fit and scale without investors, how tariffs nearly wiped out their business overnight, and what it actually takes to run a fully remote team.

Key Takeaways with Dan Demsky

(00:00) Starting an Apparel Brand

(04:23) Crowdfunding as Product-Market Validation

(05:27) Ecommerce's Hardest Problem

(06:52) When Tariffs Nearly Killed their Business

(13:09) 30% Repeat Buyers in 30 Days

(15:29) Using Crowdfunding as a Growth Engine

(28:20) Running a Fully Remote Team

(39:41) Should You Do Business with Best Friends?

(51:17) Advice to New Entrepreneurs

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Suneet Agarwal got raided by federal marshals in his underwear, lost everything from his cannabis business, sat on the couch breeding bulldogs for two years, and then built the #1 real estate team in California, selling more than $1B in a single year.

In this episode we unpack that journey. We dig into the realities of building culture in a commission-based business, why personal brand is the biggest opportunity right now, and how AI-driven content helped Suneet build and sell a high-ticket coaching business.

Key Takeaways with Suneet Agarwal

(00:00) Intro

(01:41) From Hippie Dispensary to Real Business

(05:50) The Federal Raid That Took Everything

(08:06) Home Invaded With a Gun to His Head

(12:12) From Breeding Bulldogs to $1B in a Single Year

(17:47) Are Real Estate Agents Overpaid?

(22:44) Building Culture With 1099 Contractors

(25:01) Leading from the Front

(28:12) Are Real Estate Brokerages Dying?

(30:22) Will AI Replace Real Estate Agents?

(30:28) Launching One Of The First ChatGPT Courses

(34:27) Using AI To Scale Content Creation

(37:53) Will AI Kill the Coaching Industry?

(38:43) Selling a Coaching Company Built on Organic

(42:25) Straight To High-Ticket Offers

(47:00) The Personal Brand Gold Rush

(48:41) 95% AI Content That Doesn't Feel Like Slop

(51:22) Advice for New Entrepreneurs

Watch on YouTube: https://youtu.be/FfcKI7VQgJQ

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Opening a night club or restaurant looks fun from the outside, but behind the scenes it's one of the most operationally complex businesses you can start.

That's why I was interested in speaking with Jack Zimmermann. After managing a team of over 200 people at XS in Las Vegas during its $100M peak, he returned to Austin to build Nova Hospitality, a portfolio of hospitality concepts including TenTen, Devil May Care, The Well, Mayfair, Neptune Sushi, LZR, and Coffee & Chill Austin.

Most founders in this space struggle to make even a single concept work, and somehow Jack's been able to start and scale 7.

I wanted to find out how he decides which concepts to launch, how he funds them, and how he manages the risk and pressure that comes with leading hundreds of people.

You don't have to be a restaurateur to get value from this one. Let's get into it!

Key Takeaways with Jack Zimmermann

(00:00) Running A $100M Vegas Nightclub

(06:16) Why Clubs Must Constantly Find New Customers

(07:00) Running Multiple Hospitality Concepts Successfully

(11:02) The Shift In Alcohol Consumption

(13:11) Taking Big Swings in Austin

(15:07) New Locations vs Brand New Concepts

(19:58) Using Partnerships To Expand Faster

(22:27) Why Hospitality is So Hard

(25:04) Staying Healthy in the Hospitality Industry

(26:20) Letting Your Team Put Out the Fires

(28:06) Funding Through Strategic Partnerships

(31:42) How To Build A Hospitality Concept

(36:47) What He Personally Refuses To Delegate

(40:50) Leadership Advice That Stuck

(41:45) Non-Negotiable Operating Principle

(42:55) Where Austin Hospitality Is Headed

(47:05) Advice For New Entrepreneurs

Watch on YouTube: https://youtu.be/qAsdI6N1vrE

Let's Connect:

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Today, I'm joined by Michael Chu — a five-time 7-figure founder who's built over $100M in sales by focusing on one thing: retention.

He believes churn isn't a marketing problem, it's a transformation problem. If you don't change who your clients become, they won't stay.

In this episode, we break down the identity shifts, expectation gaps, and retention frameworks that turn short-term customers into long-term profit.

And stay to the end, because we also unpack why retention in the AI era won't be built on information, but on something far harder to replicate.

Key Takeaways

(00:00) Intro

(01:13) Who Is Actually Qualified to Coach Anybody?

(03:57) Why Great Sales Reps Fail As Managers

(07:28) Teaching to Learn vs. Teaching Once You've Learned

(09:57) Will AI Kill the Coaching Industry?

(13:24) How He Went from 2 Clients to $250K/Month with No Ads

(21:17) The First 72 Hours That Determine Customer LTV

(26:20) Why McDonald's Never Gets Chargebacks

(31:53) The Somatic Session That Unlocked $100K Months

(38:18) LTV Built on Transformation, Not Revenue

(44:01) The Framework for Employee and Client Retention

(46:27) Why Belonging Beats Curriculum in the AI Era

(50:45) The Framework Behind Every Great Training

Watch on YouTube: https://youtu.be/eWbDOmSPHH8

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Ben Rubenstein has built and sold two companies: Yodle for $342M and OpCity for $210M.

In this episode, we break down the operating decisions behind those outcomes.

We talk about when venture capital accelerates growth and when it can quietly kill your business. Ben explains why ideas are worthless without execution, how he scaled a 1,000-person sales organization, and the hiring filters that consistently produced top performers.

We also get into culture, retention, speed-to-lead systems, and the strategic decisions that position companies for 9-figure exits.

If you're building and thinking about capital, hiring, churn, or long-term optionality, this conversation is a masterclass in how experienced operators think.

Key Takeaways

02:10 When to Raise VC?

04:25 Ideas Are Worthless

09:36 The 3 Traits of Elite Salespeople

14:13 Culture Doesn't Happen by Accident

24:35 How to Sell – Scripts vs Talk Tracks

25:17 Yodel – From Air Mattress to $342M

29:27 Op City – Selling for Real Estate Brokerages

32:41 Are Real Estate Agents Overpaid?

38:45 Calling Leads within 4 Seconds

42:57 The Algorithm That Became their Competitive Moat

45:25 Why Most Founders Can't Scale

46:43 Setting Expectations with Your Team

48:38 Hiring Top Talent

53:34 9-Figure Exit Strategies

58:30 The 80/20 Rule That Saves Startups

01:01:02 Setpoint – Private Capital for Asset-Backed Innovators

01:06:45 Advice to New Entrepreneurs

Watch on YouTube: https://youtu.be/wyPSp0_RV3g

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Private equity doesn't scale the way most founders do. They buy growth.

They acquire profitable businesses, combine them, and increase the value of the whole thing so they can sell at a much higher multiple.

Today's guest, Tom Shipley, is a serial entrepreneur and M&A strategist who built acquisition platforms applying that same strategy to founder-led businesses.

In this episode, we unpack the mechanics behind scaling through acquisitions and rollups, how combining businesses can dramatically increase enterprise value, and why so many founders stall at $1–2M in EBITDA without positioning their companies for a meaningful exit.

If you've ever wondered whether buying businesses is a distraction or a legitimate growth lever, this episode will change how you think about scale. Let's dive in.

Key Takeaways

(00:00) Intro

(01:54) The Two Biases That Destroy Acquisitions

(05:00) The 4 Foundations of Business Growth

(07:12) The AVA Roll-Up Story (Lessons Learned)

(15:27) How to 4X Your Business Value (Multiple Expansion Explained)

(19:11) How Acquisitions Outperform Organic Growth

(21:26) The Roll-Up Mistake That Kills the Model

(27:43) Add Zeros: How to Think Exponentially

(30:51) When to Use Acquisitions as a Tool for Growth

(39:27) Tom's Playbook for Acquiring Businesses

(54:55) What Is DealCon?

(58:49) Turns $1–2M EBITDA Owners Into PE Deals

(01:05:14) Advice to New Entrepreneurs

Watch on YouTube: https://youtu.be/oJu1sy9B6d4

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