Business Lunch

By Roland FrasierBusiness Entrepreneurship Investing

Business Lunch episodes

September 17 The Estate Planning Mistake That Tears Families Apart (Jimmy Buffett's $275M Lesson)
In This Episode Of Business Lunch: Jimmy Buffett left a 275 million dollar trust, and now his widow and his longtime business manager are suing each other in two states while the legal bills run into the millions. Roland Frasier, who practiced estate law for about 12 years, and Ryan Deiss use that fight to make a case most advisors never make: the estate plan that saves the most tax is often the one that tears the family apart. They cover who actually needs complex trusts (almost nobody under 30 million dollars), what they each plan to leave their own kids, what should happen to the business, and the few simple moves that protect a family without giving anyone you love the right to sue anyone else you love. This is a conversation about what they do themselves, not legal advice.
Chapters:
0:00 Welcome back, Ryan Deiss, and a business that keeps running when life happens
1:58 Today's topic: structuring things for when you are not there
3:08 Jimmy Buffett's 275 million dollar trust fight and the James Brown estate
9:30 Under 30 million dollars, you do not need the complex structures
12:39 What Roland wants for his kids: education, a house, shared experiences, no control from the grave
16:41 Ryan Deiss on stewardship and deciding who gets what
21:04 Never create an estate plan that gives people you love standing to sue each other
24:29 Tell your kids to expect nothing, and spend on experiences while you are alive
27:33 What happens to the business, and do the kids have to be treated equally?
34:05 Two simple tools: 14 years to pay estate tax on a business, and life insurance trusts
36:30 Give your beneficiaries the right to remove the trustee
39:27 The one box on the estate tax return that can cost a surviving spouse 6 million dollars
42:23 Six figure trust setups on small estates, and the human side advisors miss
47:09 Recap: the three moves to make, and the question to ask every advisor
Listen to Business Lunch:
Apple Podcasts: https://podcasts.apple.com/us/podcast/business-lunch/id1442654104
Spotify: https://open.spotify.com/show/0iWSA89TaD263zhXETdSvZ
Follow Roland Frasier:
Instagram: https://www.instagram.com/rolandfrasier/
LinkedIn: https://www.linkedin.com/in/rolandfrasier/
TikTok: https://www.tiktok.com/@rolandfrasier
Facebook: https://www.facebook.com/RolandFrasierPage/
Everything else: https://msha.ke/rolandfrasier/
Follow Ryan Deiss:
Instagram: https://www.instagram.com/ryandeiss/
LinkedIn: https://www.linkedin.com/in/ryandeiss/
X: https://x.com/ryandeiss
Visit: https://www.scalable.co
49 min
September 10 Retire Early or Live Fully? The FIRE Debate
In This Episode Of Business Lunch: We take on the FIRE movement, financial independence and retiring early, and ask the question most of its followers skip: what are you retiring to? They separate financial independence from retirement, walk through the 25 times rule and the 4 percent rule, explain the buckets of money approach that funds the future and the present at the same time, and share the stories behind their view that life is short and life is long, and you never know which one you get. It ends where every owner thinking about an exit should start: sell your business on a good day, and know what comes next before you go.
Chapters:
0:00 Cold open: the belief at the core of the FIRE movement
0:55 Welcome, and what retired actually means
2:42 Lean FIRE, fat FIRE, index funds, side hustles, and deferring big life events
5:13 Is working for someone else really the enemy?
6:04 Parents who missed their kids, and why deferring life is risky: 125 million dollars in bearer bonds
8:48 Waiting on kids, Lamborghinis, and the beach house that was a stretch
11:09 What to tell a young couple going all in on FIRE: support first, then buckets of money
14:52 All your eggs in one basket, in money and in time
16:03 Financial independence and retirement are two different things
18:23 The 25 times rule and the 4 percent rule
19:57 Not what you are retiring from, but what you are retiring to
23:10 Retiring from what you love, and selling your business on a good day
Listen to Business Lunch:
Apple Podcasts: https://podcasts.apple.com/us/podcast/business-lunch/id1442654104
Spotify: https://open.spotify.com/show/0iWSA89TaD263zhXETdSvZ
Follow Roland Frasier:
Instagram: https://www.instagram.com/rolandfrasier/
LinkedIn: https://www.linkedin.com/in/rolandfrasier/
TikTok: https://www.tiktok.com/@rolandfrasier
Facebook: https://www.facebook.com/RolandFrasierPage/
Everything else: https://msha.ke/rolandfrasier/
Follow Ryan Deiss:
Instagram: https://www.instagram.com/ryandeiss/
LinkedIn: https://www.linkedin.com/in/ryandeiss/
X: https://x.com/ryandeiss
Visit: https://www.scalable.co
Mentioned in this episode:
Build Your CEO Dashboard
Get one report every week of the key metrics you need to know with the CEO Dashboard!
CEO Dashboard
27 min
September 03 From Passion Project to Corporate Casualty: The TNC Saga
Roland Frasier and Ryan Deiss tell the whole story of Traffic and Conversion Summit: a marketing event that started in 2009 with 289 people and no profit, grew to thousands of attendees, and sold to Clarion Events in 2018 at the highest multiple the buyer had ever paid for an event. Then they walk through what happened after the sale: the 80 percent rollover deal, the earn out, the put and call option that paid out zero after the pandemic, and why the corporate owners could not keep the soul of an event built by marketers for marketers. Real deal structure lessons from their own exit, including how to carve off the one asset a buyer actually wants and keep everything else.
0:00 Cold open: the vision behind the best event people ever attended
0:30 Welcome, a fire alarm night, and why Traffic and Conversion Summit is officially over
3:52 2009: 289 people, no profit, and a rule against pitch fests
6:24 Year three: the event becomes a business and launches DigitalMarketer
7:54 Sponsors, production value, and no more selling from stage
12:02 Clarion Events comes calling with a global vision
14:58 The event was a product line, not a company: thin slicing the deal
17:01 Air rights and bundles of sticks: sell only what the buyer wants
19:53 Deal structure: 80 percent sold, cash plus an earn out, the goose and eggs, the put and call
24:45 Having your cake: programming control, free booth space, the only offer from stage
26:34 How it all went wrong: the pandemic, a multiple of zero, bought out for nothing
34:52 Why TNC failed: the business model changed hands
Listen to Business Lunch:
Apple Podcasts: https://podcasts.apple.com/us/podcast/business-lunch/id1442654104
Spotify: https://open.spotify.com/show/0iWSA89TaD263zhXETdSvZ
Follow Roland Frasier:
Instagram: https://www.instagram.com/rolandfrasier/
LinkedIn: https://www.linkedin.com/in/rolandfrasier/
TikTok: https://www.tiktok.com/@rolandfrasier
Facebook: https://www.facebook.com/RolandFrasierPage/
Everything else: https://msha.ke/rolandfrasier/
Follow Ryan Deiss:
Instagram: https://www.instagram.com/ryandeiss/
LinkedIn: https://www.linkedin.com/in/ryandeiss/
X: https://x.com/ryandeiss
Visit: https://www.scalable.co
39 min
August 27 How Equity Consulting Can 10X Business ROIs
In This Episode Of Business Lunch: We open our consulting for equity playbook right after wrapping a real $50,000 half day consult. They walk through the exact process step by step: getting the leadership team aligned on the problem to be solved, the 1 3 1 framework, the report of findings, and how to get buy in without losing the room. If you consult, this is a process you can run tomorrow. If you own a company, it works just as well as a self consult.
Chapters:
0:00 A real consult opens the playbook
1:00 Consulting for equity and the half day consult model
2:24 The client and the four times sales goal
5:21 Step one is alignment on the problem to be solved
6:25 Keep doing, stop doing, start doing
10:22 Value drivers and the theory of constraints
17:22 The 1 3 1 framework and the report of findings
22:26 Send recommendations before the meeting
24:52 Leads, conversion, and the ICP trap
34:18 The awareness scale and where the ads were aimed
38:36 Handling pushback without attacking the person
44:15 Agree, disagree and commit, or recuse
Listen to Business Lunch:
Apple Podcasts: https://podcasts.apple.com/us/podcast/business-lunch/id1442654104
Spotify: https://open.spotify.com/show/0iWSA89TaD263zhXETdSvZ
Follow Roland Frasier:
Instagram: https://www.instagram.com/rolandfrasier/
LinkedIn: https://www.linkedin.com/in/rolandfrasier/
TikTok: https://www.tiktok.com/@rolandfrasier
Facebook: https://www.facebook.com/RolandFrasierPage/
Everything else: https://msha.ke/rolandfrasier/
Follow Ryan Deiss:
Instagram: https://www.instagram.com/ryandeiss/
LinkedIn: https://www.linkedin.com/in/ryandeiss/
X: https://x.com/ryandeiss
Visit: https://www.scalable.co
Mentioned in this episode:
Build Your CEO Dashboard
Get one report every week of the key metrics you need to know with the CEO Dashboard!
CEO Dashboard
49 min
August 20 Can You Build a Business for Both Cash Flow and a Big Exit?
In This Episode Of Business Lunch: We tackle a question every founder faces: do you build your business for cash flow now or for a big exit later, and can one company really do both? They dig into why bootstrapped owners have far more options than funded ones, how cash left sitting in a company quietly turns into bloat, and how to pay yourself regular distributions without hurting a future sale.
Chapters:
0:00 Cold open
0:36 Welcome and where this question came from
0:55 Can one business deliver both cash flow and a big exit
1:57 The path VC funding locks you into
3:45 Why bootstrapped owners have more flexibility
9:19 How cash left in the company creates bloat
11:35 The cash flow waterfall and budgeting for distributions
12:34 How VC backing changes the exit itself
14:06 Building reserves for refunds and emergencies
16:20 Regular distributions or waiting for the big exit
18:54 Wrap up
Listen to Business Lunch:
Apple Podcasts: https://podcasts.apple.com/us/podcast/business-lunch/id1442654104
Spotify: https://open.spotify.com/show/0iWSA89TaD263zhXETdSvZ
Connect with Roland Frasier:
Instagram: https://www.instagram.com/rolandfrasier/
LinkedIn: https://www.linkedin.com/in/rolandfrasier/
TikTok: https://www.tiktok.com/@rolandfrasier
Facebook: https://www.facebook.com/RolandFrasierPage/
Everything else: https://msha.ke/rolandfrasier/
Connect with Ryan Deiss:
Instagram: https://www.instagram.com/ryandeiss/
LinkedIn: https://www.linkedin.com/in/ryandeiss/
X: https://x.com/ryandeiss
Site: https://www.scalable.co
22 min
July 30 Why 75% of Founders Regret Selling (and How to Exit Without Losing Yourself)
In This Episode Of Business Lunch: A Hartford Financial study found that 75% of business owners regret selling their company. Roland Frasier and Ryan Deiss have both lived it, and they get personal about what the wire does not fix: the identity you give up with the business, the buyer promises that rarely survive the close, and why more than half of sellers wind up swooping back in. Then the way out: fulfillment continuity, the threads you build before the exit so you are not adrift after it.
If you have exited a business, share in the comments what surprised you most about life on the other side.
Chapters:
0:00 The telescope and why founders exit unhappy
1:57 The Hartford study: 75% of owners regret selling
4:22 Roland's identity shift after leaving law
6:02 Ryan on exiting Traffic and Conversion Summit
9:10 What buyers promise vs the post exit reality
13:52 Why due diligence pulls the two sides apart
19:46 Business partnerships are marriages: extending grace
23:45 The threads that save you from being adrift
27:02 Fulfillment continuity: Roland's framework
32:14 Find the part of the business that fulfills you
40:47 Reallocating your time as seasons change
48:20 The miserable rich person trap
49:04 Fire and rehire yourself every year
Listen to Business Lunch:
Apple Podcasts: https://podcasts.apple.com/us/podcast/business-lunch/id1442654104
Spotify: https://open.spotify.com/show/0iWSA89TaD263zhXETdSvZ
Roland Frasier:
Instagram: https://www.instagram.com/rolandfrasier/
LinkedIn: https://www.linkedin.com/in/rolandfrasier/
TikTok: https://www.tiktok.com/@rolandfrasier
Facebook: https://www.facebook.com/RolandFrasierPage/
More: https://msha.ke/rolandfrasier/
Ryan Deiss:
Instagram: https://www.instagram.com/ryandeiss/
LinkedIn: https://www.linkedin.com/in/ryandeiss/
X: https://x.com/ryandeiss
Scalable: https://www.scalable.co
Mentioned in this episode:
Build Your CEO Dashboard
Get one report every week of the key metrics you need to know with the CEO Dashboard!
CEO Dashboard
52 min
July 23 When to Let the Dumpster Fire Burn (and Why AI Is Breaking Hiring)
Not every problem in your business is yours to fix. Roland Frasier and Ryan Deiss break down how to tell a seasonal slump from a fire you actually started, why the easy and obvious moves matter most when the numbers dip, and how AI written resumes are quietly breaking hiring for small businesses. Plus the internal recruiter role they think every growing company is about to need.
0:00 Welcome back from a 30 day vacation
1:46 Why rest is actually productive work
3:20 When do you let the dumpster fire burn?
4:52 Internal vs external: what you can and cannot fix
6:00 Control what you control: lead flow and double booking
6:51 Do the easy and obvious things well
10:07 Red vs yellow metrics on the scorecard
15:46 Theory of constraints: which fire to fight first
17:47 Why small businesses aren't hiring: the AI resume problem
20:01 How to interview when AI writes every resume
25:20 The pre interview email that filters out a third of applicants
26:53 The rise of the internal recruiter
Listen to Business Lunch:
Apple Podcasts: https://podcasts.apple.com/us/podcast/business-lunch/id1442654104
Spotify: https://open.spotify.com/show/0iWSA89TaD263zhXETdSvZ
Roland Frasier:
Instagram: https://www.instagram.com/rolandfrasier/
LinkedIn: https://www.linkedin.com/in/rolandfrasier/
TikTok: https://www.tiktok.com/@rolandfrasier
Facebook: https://www.facebook.com/RolandFrasierPage/
More: https://msha.ke/rolandfrasier/
Ryan Deiss:
Instagram: https://www.instagram.com/ryandeiss/
LinkedIn: https://www.linkedin.com/in/ryandeiss/
X: https://x.com/ryandeiss
Scalable: https://www.scalable.co
36 min
July 16SEO vs AEO: What Every Business Needs to Know
In This Episode of Business Lunch: We explore the evolving landscape of search engine optimization (SEO) versus answer engine optimization (AEO), and how businesses can adapt their strategies to stay ahead in AI-driven search environments. They discuss practical tactics, the importance of evidence and authority, and how to leverage paid and organic channels effectively.
Chapters:
00:00 Introduction and Episode Overview
00:17 Challenges with Technology and Setup
00:30 Introduction to ChatGPT Ads and Platform Insights
00:58 SEO vs AEO: What's the Difference?
01:26 Understanding Search Engine Optimization and Answer Engine Optimization
02:02 Should You Invest in SEO Now?
02:30 Clarifying SEO, GEO, and Generative Engine Optimization
03:06 How Answer Engines Are Replacing Search Engines
03:42 The Shift from Rankings to Recommendations
04:15 Using Search Engines for Direct Source Verification
04:56 The Changing Role of Search in Customer Awareness Levels
05:36 Branded Search and Its Importance
06:01 The Evolving Nature of Search Optimization
06:19 Optimizing for Recommendations, Not Rankings
07:15 Bidding Strategies on Competitors and Trademark Terms
08:40 Cost-Effective Strategies for Competing in Answer Engines
10:00 Practical Approach for Business Owners
11:00 From Rankings to Recommendations: New Optimization Goals
12:08 The Role of Evidence and Proof in AI Recommendations
13:15 Creating Credibility and Authority for Search Engines
14:06 Content Strategy for AEO Success
15:29 Schema and Technical SEO for AI
16:29 Building the Neural Network: Assets and Relationships
17:32 Practical Steps to Optimize for AI and Answer Engines
18:36 Focusing on Questions, Not Keywords
19:10 Gathering Evidence to Prove Authority
20:39 Distribution, Freshness, and Uniqueness in Content
21:26 The Importance of Original and Contrarian Content
22:29 Using the Skyscraper Strategy for AI Optimization
23:46 Reverse Engineering Top Sources and Cited Content
25:38 Prioritizing Strategies Based on Business Needs
26:09 Shifting Budgets from SEO to AEO
27:05 Content and Embedded Influencers for Organic Growth
28:14 Paid Search and Branded Terms for Immediate Impact
29:41 Balancing Organic and Paid Strategies
33:02 The Role of Authority and Evidence in AI Rankings
36:34 Starting with Paid Search and Organic Content
37:49 The Future of Search and Business Strategy
40:13 Encouragement to Experiment and Share Results
42:22 Final Thoughts and Wrap-up
Connect with me on social:
TikTok: Check out my TikTok Here
Instagram: Check out my Instagram Here
Facebook: Check out my Facebook Here
LinkedIn: Check out my LinkedIn Here
Subscribe to my YouTube 👉 Here

Resources:
• 7 Steps to Scalable workbook
• Get my book, Zero Down, FREE
Mentioned in this episode:
Build Your CEO Dashboard
Get one report every week of the key metrics you need to know with the CEO Dashboard!
CEO Dashboard
44 min
July 09Breaking Free from Founder Identity Debt
In This Episode of Business Lunch: We explore the concept of founder identity and how legacy identity debt can hinder business growth. They discuss practical strategies for recognizing and overcoming identity lag to scale effectively.
Chapters:
00:00 Introduction to founder identity and role evolution
00:30 The five stages of role evolution in business
00:58 Understanding identity lag and its effects
01:28 The concept of identity debt in business
02:24 Sleep debt analogy and identity debt
02:51 Impact of legacy identity debt on scaling
03:22 Recognizing when you're in the wrong role
04:05 The importance of role clarity and job descriptions
08:06 How to get consciously competent and fix identity debt
09:44 Defining your current role and responsibilities
10:14 Using time studies to identify role mismatches
11:52 Addressing comfort work and role reversion
12:24 Resetting roles and accountability with team members
13:19 The importance of honest communication and ownership
14:38 Handling time constraints and delegation
16:29 Hiring the right roles and using AI tools
17:12 Recognizing and overcoming identity debt in business
17:43 Summary: Overcoming insidious identity debt
Connect with me on social:
TikTok: Check out my TikTok Here
Instagram: Check out my Instagram Here
Facebook: Check out my Facebook Here
LinkedIn: Check out my LinkedIn Here
Subscribe to my YouTube 👉 Here

Resources:
• 7 Steps to Scalable workbook
• Get my book, Zero Down, FREE
Mentioned in this episode:
Build Your CEO Dashboard
Get one report every week of the key metrics you need to know with the CEO Dashboard!
CEO Dashboard
21 min
July 02Micro CEOs: The Future of Agile Business Teams
In This Episode of Business Lunch: This episode explores the myth of hiring A players, the concept of micro CEOs, and how to structure teams for maximum agility and profitability in the AI era. Ryan Deiss and Roland Frasier discuss the pitfalls of traditional hiring and the advantages of outcome-based roles.
Chapters:
00:00 The A-Player Debate
02:52 Hiring Owners vs. A-Players
05:57 Understanding Micro CEOs
08:51 The Role of Metrics in Hiring
11:58 Compensation Structures for Micro Owners
14:55 The Future of Leadership in Business
Connect with me on social:
TikTok: Check out my TikTok Here
Instagram: Check out my Instagram Here
Facebook: Check out my Facebook Here
LinkedIn: Check out my LinkedIn Here
Subscribe to my YouTube 👉 Here

Resources:
• 7 Steps to Scalable workbook
• Get my book, Zero Down, FREE
Mentioned in this episode:
Build Your CEO Dashboard
Get one report every week of the key metrics you need to know with the CEO Dashboard!
CEO Dashboard
37 min

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How much more successful would you be if you had lunch once a week with an insanely successful entrepreneur who shared their biggest secrets on how they think and achieve success? Well, now you can!…