In this week’s episode of Business Lunch, Roland Frasier and Ryan Deiss continue breaking down the “Bottlenecks” framework—the 11 proven playbooks that billionaires use to grow, protect, and multiply wealth.

From AI-driven acquisitions to tax-optimized exits, this conversation dives into the strategies that separate ordinary entrepreneurs from long-term empire builders. You’ll hear how the world’s wealthiest think about capital allocation, scaling “boring” businesses, and structuring companies for massive, tax-efficient exits.

Whether you’re scaling your first venture or managing a growing portfolio, this episode is a tactical deep dive into how to think—and act—like a billionaire.

Key Takeaways

• Tech Is Not a Moat: With AI making innovation easy to copy, your real advantage is distribution and users.

• The QSBS Advantage: How the Qualified Small Business Stock exemption can eliminate up to $10M (or more) in capital gains per shareholder.

• DAFs & Charitable Strategy: Donor Advised Funds can combine tax savings with long-term impact—if structured correctly.

• Boring Businesses, Billionaire Results: Logistics, energy, and real estate can quietly create generational wealth when value is added and scaled.

• Capital Cycling: Why the world’s best investors (like Blackstone and Berkshire) act like banks—recycling capital and compounding returns.

Episode Highlights

[00:02:00] – Why tech is easy to copy—and why users, not code, create real enterprise value.

[00:10:00] – The billionaire tax play: how QSBS and DAFs legally minimize or eliminate capital gains.

[00:18:00] – When to start thinking about tax strategy (hint: usually not before $10M net worth).

[00:25:00] – Logistics, land, and “boring” businesses that create quiet fortunes.

[00:33:00] – The ESG arbitrage: adding sustainability to raise valuations.

[00:40:00] – Network effects and marketplace rollups: creating compounding flywheels.

[00:55:00] – The rise of “edge retail”: micro-brands, coffee chains, and inversion models that scale fast.

[01:05:00] – Capital cycling and other people’s money (OPM): how billionaires play the funding game.

Memorable Quotes

“If all you are is a feature that someone else could build, you don’t have a business—you have a countdown clock.”

“Boring businesses aren’t boring when they compound quietly into billions.”

“It’s not what you make—it’s what you keep.”

“Billionaires don’t think like operators; they think like capital allocators.”

Mentioned in This Episode

• Qualified Small Business Stock (QSBS) – U.S. tax exemption strategy
• Donor Advised Funds (DAFs) – Philanthropic and tax planning vehicles
• Ross Perot Jr. – Logistics real estate
• Dutch Bros – Scalable retail model example
• Blackstone & Berkshire Hathaway – Capital cycling and compounding models

Listen If You’re

• A founder or investor learning to structure smarter deals.
• A CEO or operator ready to scale beyond execution into capital allocation.
• A strategic thinker who wants to play the long game in business and wealth creation.

Connect

• Hosts: Roland Frasier & Ryan Deiss
• Podcast: Business Lunch with Roland Frasier
• More at: businesslunchpodcast.com

Mentioned in this episode:

Join Roland & Ryan at Get Scalable Live

If you’re a founder, CEO, or operator running a 7- or 8-figure business, Get Scalable Live was built for you. This is not your typical business event. It’s 3 days of hands-on strategy, real-world frameworks, and next-level networking with the smartest operators in the game. 🗓 November 18–20, 2025 📍 San Diego, CA 🎉 Hosted by Ryan Deiss,...

In this episode of Business Lunch, Roland Frasier and Ryan Deiss explain how the classic four-stage buying journey has collapsed into one moment—and why trust is the lid that keeps prospects “popping” in your pot. They unpack three forms of trust—Identity, Competence, and Proximity—with sharp wins and public flops (Nike, Sephora, Peloton, DSW, Starbucks, Apple, United). You’ll get simple creative frameworks to turn short-form content into instant, in-channel conversions and a 14-day sprint to prove it on a small budget.

• “It’s not a funnel anymore—it’s a popcorn popper. Your audience are kernels heating at different speeds. Trust is the lid that keeps them popping for you.”
• “Competence trust means the brand ‘gets me’—often better than I can describe myself.”
• “Employees outperform celebrities for reach and credibility—because most buyers are employees.”
• “Frictionless is forgettable. Add desirable friction that helps buyers name their pain and act.”
• “If you can’t pivot your model, bolt trust into your media: mirror-micro-media, why-what-where, people-place-proof.”

Three Trust Types (MAP mnemonic):

• M – Identity trust: Mirror → Micro → Media
• A – Competence trust: “Answer” with Why → What → Where
• P – Proximity trust: People → Place → Proof

Competence wins & misses: Nike’s “Why do it?” repositioning; Sephora tutorials lifting AOV; Peloton’s 2019 holiday ad backlash.

Proximity plays: DSW AR try-ons; Starbucks barista TikToks; Apple retail specialists; cautionary tale—United Airlines viral incidents.

Localization tactics: regional currency/sites, geo-specific visuals (city skylines), and micro-influencers by market.

KPI effects: higher AOV/retention/loyalty from competence; higher LTV from proximity; employee posts driving outsized reach.

• 00:00 – The collapsed customer journey: from funnel to popcorn popper (trust as the lid)
• 04:00 – Recap: Identity trust (mirror, micro, media)—and why episodes stand alone but compound
• 07:30 – Competence trust: the brand that “gets me” (Nike shift, Sephora demos) + Peloton misread
• 14:20 – Framework for competence: Why → What → Where (myth-bust, demo, direct CTA)
• 17:30 – Example: 30-sec tax advisory myth-buster → LinkedIn/Reels → consult link → track AOV
• 20:10 – Proximity trust: employees, in-place context, show real proof (DSW AR, Starbucks, Apple)
• 24:10 – Employee content > celebrity polish; make it authentic, even shot on phone
• 26:00 – 14-day Trust Sprint and MAP recap; why proximity is overlooked yet most scalable

• Stop chasing linear funnels; engineer trust in-channel so action can happen immediately.
• Use Why → What → Where to collapse steps: name the pain, show the fix, drop the link.
• Turn staff into a media network: People → Place → Proof with incentives and simple tracking.
• Localize by currency, domains, visuals, accents, micro-influencers—it quietly multiplies conversion.
• Run a 14-day sprint: baseline CAC/AOV → recruit 3 customers + 3 insiders → record shorts →...

In this episode of the Business Lunch podcast, Host Roland Frasier and guest Richard Lindner break down the subscription trap and why recurring revenue isn’t always the ultimate solution it’s made out to be.

From the outside, subscription models look like a dream: predictable cash flow, higher valuations, and a business that doesn’t start at zero each month. But as Roland and Richard reveal, the reality can be far more complicated.

They dive into real stories from their portfolio companies, showing how recurring revenue can backfire through hidden churn, customer support debt, and endless innovation demands. You’ll hear how even big players like Netflix constantly battle to keep customers engaged, and why smaller businesses often underestimate the true cost of service.

This episode is a must-listen if you’re considering shifting to a subscription model—or if you’ve already launched one and want to make sure it’s sustainable.

HIGHLIGHTS

“Recurring revenue is great… until you’re losing more members each month than you know how to gain.”

“There’s voluntary churn, where people cancel. But the killer is involuntary churn—declined payments, expired cards—that can quietly eat your business alive.”

“If you’re creating content subscriptions, pair them with community. Access is the real value that keeps people sticking around.”

“Don’t fall in love with the model. Define your business by who you serve, not just how you charge.”

Mentioned in this Episode

The difference between breakage vs. consumption models (think Netflix vs. gym memberships)

Why AI in customer support is changing the economics of subscription businesses

How to tell if your business should pursue a bolt-on subscription or avoid it altogether

🎧 Whether you’re launching your first subscription offer or scaling an existing one, this episode will help you see beyond the hype and make smarter decisions for long-term growth.

Timestamps:

00:00 – Intro & The Subscription Trap

02:10 – Should Every Business Go Subscription?

04:58 – Understanding Churn & Retention

07:52 – The Innovation Challenge

10:23 – Cost of Service & Support Debt

13:35 – Smarter Models: Community + Content

19:31 – Key Questions Before You Launch

CONNECT

• Ask Roland a question HERE.

RESOURCES:

• 7 Steps to Scalable workbook

• Get my book, Zero Down, FREE

To learn more about Roland Frasier 👉 https://msha.ke/rolandfrasier/

Connect with me on social:

🎵 TikTok: https://www.tiktok.com/@rolandfrasier

📸 Instagram: https://www.instagram.com/rolandfrasier/

📱 Facebook: https://www.facebook.com/RolandFrasierPage/

💼 LinkedIn: https://www.linkedin.com/in/rolandfrasier/

Subscribe to Roland Frasier 👉 https://www.youtube.com/channel/UCkHnnFgdaTCg8KBd7W_LGSw?sub_confirmation=1

Mentioned in this episode:

Join Roland & Ryan at Get Scalable Live

If you’re a founder, CEO, or operator running a 7- or 8-figure business, Get Scalable Live was built for you.

This is not your typical business event. It’s 3 days of hands-on strategy, real-world frameworks, and next-level networking with the smartest operators in the game.

Event Link: https://business-lunch.captivate.fm/gsl

🗓 November 18–20, 2025

📍 San Diego, CA

🎉 Hosted by Ryan Deiss, Roland Frasier, and Richard Lindner

🎧 As a Business Lunch listener, you get 25% off your ticket.

Use code LUNCH at checkout.

Get Scalable Live

Mentioned in this episode:

Join Roland & Ryan at Get Scalable Live

If...