Navigating Wealth

Latest Episodes:

Why Disney is Licensing Characters to OpenAI (And What Happens Next) - Michael Sapherstein Mar 04, 2026

Show notes

Today we're thrilled to welcome Michael Sapherstein, the former in-house counsel at Major League Baseball, Marvel Entertainment and The Walt Disney Company.

Mike takes us behind the scenes of the "billion-dollar business you've never heard of" (MLB Advanced Media) and explains how he navigated the legal frontiers of the digital revolution, from the first iPad comic books to the looming impact of generative AI on creative ownership.

Key Topics Covered:
• The Streaming Blueprint: How MLB Advanced Media centralized rights to become the technical backbone of Disney+.
• The Marvel Licensing Machine: Why Marvel was a "pure profit" powerhouse and how the iPad changed their business model overnight.
• The AI Anathema: A veteran lawyer’s take on the "unfair" ingestion of IP and why Disney is now licensing characters to OpenAI.
• The Legal Wealth Gap: Why Big Law partners often miss out on the "ownership economy" due to ingrained risk aversion.
• Career Resilience: Advising the next generation on majoring in "thinking" rather than just "coding" in the age of Claude and Sora.

Links:
• Apply to Join Long Angle (no membership fees): https://www.longangle.com/apply-now-nw
• Learn More About our Sponsor - Daily Body Coach: http://www.dailybodycoach.com/navigatingwealth

Long Angle is a private, vetted global community of accomplished entrepreneurs, executives, and professionals who have reached meaningful financial milestones and want to navigate wealth with peers who understand their challenges, opportunities, responsibilities, and ambitions.

#NavigatingWealth #LongAngle #MichaelSaperstein #Disney #Marvel #AITrends #IPLaw #GenerativeAI #Sora #Licensing #HighNetWorth #InvestorOperator #OwnershipEconomy

Inside $22B Airline Loyalty & Getting Your First Board Seat - Tom O'Toole Feb 25, 2026

Show notes

Today we're thrilled to welcome Tom O’Toole, a seasoned executive and Long Angle member who previously served as the CMO of Hyatt Hotels and United Airlines. In this episode, Tom pulls back the curtain on the multi-billion dollar business of airline loyalty programs and shares his strategic roadmap for building a successful "portfolio life" after retiring from the C-suite.

Key Topics Covered:

The Economics of Loyalty: Why United’s Mileage Plus was valued at $22B and how airline miles function as the world’s third most used currency.
Dynamic Pricing & Inventory: An inside look at how airlines engineer award availability and the shift toward rational, demand-based pricing.
The Boardroom Roadmap: Critical advice for securing public and private board seats, including why you need a two-year lead time.
Designing a Portfolio Life: How to balance board service, senior advising for firms like McKinsey, and teaching at top-tier universities like Northwestern.
Intentional Career Design: Why a post-corporate career must be an "engineered outcome" rather than an accidental retirement.

Links:

Learn More About Daily Body Coach: http://www.dailybodycoach.com/navigatingwealth
Apply to join Long Angle’s Community: https://www.longangle.com/apply-now-nw

Hosted by the founders of the Long Angle community, Navigating Wealth is a podcast for founders, executives, and investor operators who have built significant wealth. Each episode features a guest with an unusual career journey and deep expertise across some aspect of the economy, investing, family, health, or lifestyle.

How to Invest in a Franchise Business - Andy Louis-Charles Feb 18, 2026

Show notes

Today we're thrilled to welcome Andy Louis-Charles, a seasoned operator, "refounder," and self-described franchise maximalist. After serving as the Chief Strategy Officer at Custom Ink and navigating a major liquidity event, Andy shifted his focus from chasing a "satisfying number" to playing an infinite game.

In this episode, Andy breaks down his "Inter-Opus" philosophy—the idea that true fulfillment isn't found before or after a goal, but while you are in the flow of meaningful work. He also demystifies the world of franchising, explaining why it is a superior alternative to traditional employment and a powerful vehicle for white-collar workers to transition into the ownership economy.

Links:

• Apply to Join Long Angle's Community: https://www.longangle.com/apply-now-nw

• Learn More About Daily Body Coach: http://www.dailybodycoach.com/navigatingwealth

Key Topics Covered:

• Andy introduces the "Inter-Opus" philosophy, explaining that true fulfillment is found during the process of meaningful work rather than before or after reaching a milestone.

• The conversation explores why Andy shifted from angel investing to franchising to focus on underwriting execution risk rather than product-market fit.

• Andy defines the "refounder" role as a specialist who identifies plateaued businesses and applies new systems to help them scale to the next level.

• The discussion details why franchising acts as a superior growth and financing model by flipping the traditional employer-employee relationship on its head.

• Andy predicts a massive displacement of white-collar workers and advocates for a transition into an ownership economy through scalable franchise units

Travel Hacking Credit Cards - Chris Hutchins Feb 11, 2026

Show notes

Today we're thrilled to welcome Chris Hutchins, host of the All the Hacks podcast with over 1 million listeners. Chris is a serial entrepreneur who co-founded companies acquired by Google and Wealthfront, served as a Partner at Google Ventures, and has accumulated over 14 million credit card points while helping people optimize their finances, travel, and health without turning it into a second job.

Key Topics Covered:

Why two credit cards is the optimal number for most busy professionals
How AI tools like ChatGPT and Claude can cut through financial noise
When to splurge on business class and when economy makes more sense
Teaching kids about money and value when you travel in premium cabins
Two quick wins: checking for unclaimed money and emailing hotels before arrival
How to know when optimization is worth your time vs. when to take the 80/20 approach

Links:

All the Hacks Podcast: https://www.allthehacks.com
Long Angle Community: https://www.longangle.com/apply-now-nw
Learn More About Daily Body Coach: http://www.dailybodycoach.com/navigatingwealth

#ChrisHutchins #AllTheHacks #CreditCardStrategy #TravelHacks #FinancialOptimization #TravelRewards #ParentingAndWealth #LongAngle #NavigatingWealth

Selling Your SaaS Business? Use This Checklist to Get the Highest Valuation - Diamond Innabi Feb 04, 2026

Show notes

Today we're thrilled to welcome Diamond Innabi, Principal at Software Equity Group.

Diamond has spent 15 years at the front lines of SaaS M&A, guiding founders through exits from first unsolicited offer to multi-million dollar closes. She shares practical insights on timing your exit, running competitive deal processes, and navigating the complexities of earnouts, rollover equity, and post-acquisition transitions.

Key Topics Covered:
• What investment banking actually means for SaaS founders
• The 4-6 month M&A timeline and when to start preparing
• Why founders hire investment bankers vs. running the process themselves
• Strategic buyers vs. private equity: different motivations and evaluation criteria
• Valuation factors that matter most in today's market
• How to position companies with customer concentration or complex technology
• Earnouts and rollover equity: what makes them acceptable vs. problematic
• Managing employee and leadership transitions post-acquisition
• SEG's 20 Factor Valuation Scorecard framework
• The current M&A market environment and what buyers want right now

Links:
• Learn More About Daily Body Coach: http://www.dailybodycoach.com/navigatingwealth
• Apply to Join Long Angle's Community: https://www.longangle.com/apply-now-nw
• Software Equity Group: https://softwareequity.com

The Billion Dollar Question: When Do You Actually Need a Family Office? - Ilka Gregory Jan 28, 2026

Show notes

Today we're thrilled to welcome Ilka Gregory, President and CEO of a seventh-generation single family office that's been managing wealth since 1866. With two decades of experience across Goldman Sachs, Bessemer Trust, Lazard Family Office Partners, and Third Avenue Management, Ilka brings rare insight into what it takes to steward family wealth across multiple generations and navigate the complex decisions that come with substantial assets.

Key Topics Covered:

• What a family office actually is and when you need one

• Managing wealth across seven generations and 80+ family members

• The reality of the "shirtsleeves to shirtsleeves" wealth cycle

• How to prepare the next generation without paralyzing them

• State tax policy impacts on family office location decisions

• Integrating spouses and stepchildren into family governance

• Practical guidance for first-generation wealth creators

• Building trusted advisor relationships and peer networks

Links:

• Connect with Ilka Gregory: https://www.linkedin.com/in/ilka-gregory/

• Learn More About Daily Body Coach: http://www.dailybodycoach.com/navigatingwealth

• Subscribe to our free newsletter: https://www.longangle.com/navigating-wealth-podcast

• Apply to join Long Angle’s Community: https://www.longangle.com/apply-now-nw

Private Equity Exit Strategy. What Happens After Selling? - Eric Wiklendt Jan 21, 2026

Show notes

Today we're thrilled to welcome Eric Wiklendt. Eric is a Managing Director and Partner at Speyside Equity, where he leads middle-market manufacturing investments. With experience as a former manufacturing CEO at Kelix Heat Transfer Systems and leadership roles at Eaton and Hilti, Eric brings an operator's perspective to private equity. He holds a BBA from Notre Dame and an MBA from Wharton, focusing on turning complex manufacturing businesses into high-performing assets.

Key Topics Covered:
• The three exit scenarios every founder should understand (full exit, transition, continuation)
• What to actually expect when selling to private equity vs. a strategic buyer
• How operator-led PE firms differ from traditional investment banking-driven firms
• Why the shift from growth-focused to EBITDA-focused can surprise founders
• Current manufacturing trends: tariffs, reshoring, and workforce challenges
• The impact of AI and automation on manufacturing jobs
• The K-shaped economy and what it means for middle-class manufacturing jobs

Links:
• Learn More About Daily Body Coach: http://www.dailybodycoach.com/navigatingwealth
• Speyside Equity: https://www.spacesideequity.com
• Eric Wiklendt on LinkedIn: https://www.linkedin.com/in/ericwiklendt
• Long Angle Community: https://www.longangle.com/apply-now-nw

How Novel Research on Worms Lead to an ALS Treatment Breakthrough - Eric Green, M.D., Ph.D. Jan 14, 2026

Show notes

Today we're thrilled to welcome Eric Green, M.D., Ph.D., CEO and Co-Founder of Trace Neuroscience. Eric is a physician-scientist and entrepreneur who has spent over a decade building genetics-focused biotech companies, including MyoKardia and Maze Therapeutics. At Trace, he's developing the first targeted genomic medicine for ALS in nearly a century, using human genetic insights to restore a critical protein that enables nerve-muscle communication.

Key Topics Covered:

• How sequencing thousands of human genomes reveals which genes matter for disease

• Why people with ALS lose the same protein that makes worms uncoordinated

• How genetic medicines work at the molecular level to target specific RNA

• The role of contract manufacturers in enabling biotech innovation

• Designing clinical trials for severe diseases where patients only get one chance

• Lessons from COVID-19 on balancing speed and safety in drug development

• The economics of drug pricing and why generics matter for long-term affordability

Links:

• Trace Neuroscience: https://traceneuro.com

• Learn More About Daily Body Coach: http://www.dailybodycoach.com/navigatingwealth

• Apply to join Long Angle's Community: https://www.longangle.com/apply-now-nw

Why Most Cybercrime Is Opportunistic, Not Targeted - Jason Passwaters Jan 07, 2026

Show notes

Today we're thrilled to welcome Jason Passwaters, co-founder and CEO of Intel 471, a leading cyber threat intelligence company. Jason is a 12-year U.S. Marine Corps veteran who specialized in counterintelligence and interrogation before transitioning to the private sector. He worked as an FBI contractor tracking cyber criminals through network forensics, then co-founded Intel 471 in 2014, growing it to $20 million in ARR without outside funding before partnering with private equity firm Thoma Bravo. Today, Intel 471 employs 250+ people globally and provides threat intelligence to Fortune-level enterprises and governments.

Key Topics Covered:

• Practical cybersecurity steps for individuals with $10-20M+ in assets

• Why most financially motivated cybercrime is opportunistic, not targeted

• How modern ransomware operations function like professional SaaS companies

• The professionalization of cybercrime with affiliate programs and customer support

• Real stories of tracking cyber criminal crews in Russia and Eastern Europe

• How corruption undermines international law enforcement efforts

• What Intel 471 does: exposure monitoring, threat intelligence, and threat hunting

• Why AI is Jason's biggest concern—lowering barriers for attacks at scale

• The journey from Marine Corps interrogator to bootstrapped cyber CEO

Links:

• Jason Passwaters on LinkedIn: https://www.linkedin.com/in/jspasswaters/

• Intel 471: https://intel471.com

• Long Angle Community: https://www.longangle.com/apply-now-nw

How to Invest in Music Royalties - Jason Peterson Dec 31, 2025

Show notes

We're thrilled to welcome Jason Peterson, Founder, Chairman & CEO of GoDigital Media Group. Jason started his career producing a Sundance film at 19, went to law school, and founded his company while still a student.

Today, GoDigital manages several hundred thousand music copyrights globally, working with artists like Janet Jackson, Jason Derulo, and Daddy Yankee. Jason shares how he navigates wealth and relationships, why music is a compelling non-correlated asset class, and his perspective on AI's impact on the entertainment industry.

Key Topics Covered:
• How wealth changes friendships and family relationships—and strategies for maintaining authentic connections
• Building GoDigital from coffee meetings during law school to managing hundreds of thousands of copyrights
• Why music is a non-correlated asset class with 7-15% yields and appreciation potential
• The economics of streaming royalties and catalog acquisitions
• Why Latin American and African music represent major growth opportunities
• AI-generated content and the "post-truth era" in media
• Overcoming imposter syndrome at the highest levels of business

Links:
• GoDigital Media Group: https://godigitalmg.com
• Long Angle Community: https://www.longangle.com/apply-now-nw

#wealth #entrepreneurship #musicindustry #investing #podcast

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