Why The Best Philanthropy Doesn't Start with a Check - Brent and Kyle Pease

Why The Best Philanthropy Doesn't Start with a Check - Brent and Kyle Pease

Today we're thrilled to welcome Brent and Kyle Pease, co-founders of the Kyle Pease Foundation and co-creators of 29029, the endurance event where participants climb the vertical equivalent of Everest in 36 hours. Brent and Kyle built a $3 million nonprofit from zero while working other jobs on the side.  In this episode they share how they think about mission-aligned hiring, why the overhead ratio is the wrong way to evaluate a nonprofit, how donors deepen their giving over time, and what the time, talent, and treasure framework actually looks like in practice. Key Topics Covered • Why the overhead ratio misleads even sophisticated donors, and what to ask instead • How mission-aligned hiring works at a nonprofit built around athletes with disabilities • The donor who gave zero for two years and now gives $50,000 annually • Revenue structure across crowdfunding, grants, and major gifts • Why Brent and Kyle kept their own salaries low to protect the mission • The earn-and-donate question: when writing the check creates more impact than showing up • How 29029 used purposeful scarcity to protect the experience as it scaled • A practical framework for giving: time, talent, and treasure Valuable Links • Subscribe to Navigating Wealth Newsletter: https://www.longangle.com/navigating-wealth-podcast • Apply to Long Angle HNW Community: https://www.longangle.com • Kyle Pease Foundation: https://kylepeasefoundation.org/ • Connect with Brent Pease on LinkedIn: https://www.linkedin.com/in/brent-pease-781a884/ Socials • LinkedIn: https://www.linkedin.com/company/long-angle • Twitter/X: https://x.com/LongAngleHNW • Instagram: https://www.instagram.com/longanglehnw/ • Facebook: https://www.facebook.com/longanglehnw 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. Hosted by the founders of the Long Angle community, Navigating Wealth explores how experienced investors, founders and operators approach the real questions wealth creates — from private markets and capital allocation to business exits and life design. #KylePeaseFoundation #Nonprofit #Philanthropy #CharitableGiving #NonprofitLeadership #NavigatingWealth #LongAngle #SocialImpact

The Controversial Asset Class Historically Outperforming the Stock Market - Jason Bertoldi

Today we're thrilled to welcome Jason Bertoldi, litigation finance veteran and Managing Director at Alliant. He has spent his career on every side of the asset class — as a plaintiff's attorney at one of the firms that helped build commercial litigation funding, as an investor at D.E. Shaw, and now as a broker of litigation insurance.  Jason breaks down how outside capital funds legal claims, why historical returns in the 30% range are giving way to a more structured capital stack, how insurance is solving the duration problem, and what sophisticated allocators need to understand before entering the space. Key Topics Covered • What litigation finance actually is: how a lawsuit becomes a contingent receivable and a financial asset • Why litigation funding exists alongside contingency fee arrangements and when each is appropriate • The history of the asset class and how institutional capital entered over the past two decades • Who the typical participants are on both the plaintiff and capital sides • How information asymmetry and adverse selection shape the underwriting process • How settlements interact with funding structures and what that means for investor returns • The ethics debate and why the economics of underwriting independently check against frivolous litigation • International litigation finance, including the UK Competition Appeal Tribunal and investor-state arbitration • Where in a portfolio litigation finance belongs — credit sleeve, equity sleeve, or its own bucket • The correlation question: why legal outcomes are independent of public markets, with the honest COVID caveat • Historical IRRs in the 30s, how insurance is changing the return profile, and what maturation means for new entrants • Secondary markets, refinancing dynamics, and how hedge funds and private credit players are entering the space Resources Mentioned • Apply to Long Angle HNW Community: https://www.longangle.com/apply • Subscribe to Navigating Wealth Newsletter: https://www.longangle.com/navigating-wealth-podcast • Connect with Jason Bertoldi on LinkedIn: https://www.linkedin.com/in/jason-bertoldi/ Socials • LinkedIn: https://www.linkedin.com/company/long-angle • Twitter/X: https://x.com/LongAngleHNW • Instagram: https://www.instagram.com/longanglehnw/ • Facebook: https://www.facebook.com/longanglehnw • Youtube: https://www.youtube.com/@LongAngle Streaming • Apple Podcasts: https://podcasts.apple.com/us/podcast/navigating-wealth/id1848166539 • Spotify: https://open.spotify.com/show/074oa2E0nnJygruIqonRVG?si=4959bcd409854a6a • Amazon Music: https://music.amazon.com/podcasts/54d4ccd0-c308-4388-81ca-abfef12fadf4/navigating-wealth 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. Hosted by the founders of the Long Angle community, Navigating Wealth explores how experienced investors, founders and operators approach the real questions wealth creates — from private markets and capital allocation to business exits and life design.

Earnings Calls Decoded by a Former Coinbase IR Executive - Anil Gupta

Today we're thrilled to welcome Anil Gupta, former Head of Investor Relations at Coinbase and eight-year veteran of Meta's IR team.  Anil breaks down how investor relations works, why a first-day IPO pop is a wealth transfer rather than a success signal, what Coinbase's direct listing decision actually meant for employees, and how to read an earnings call when you understand how the other side prepares for it. Key Topics Covered • What investor relations does: the finance-communications hybrid that shapes everything investors see • How IR teams prepare for earnings calls and what the most rehearsed answers actually signal • Why a first-day IPO pop means existing shareholders left money on the table • How a direct listing differs from a traditional IPO and why Coinbase chose it • Why the best companies (SpaceX, OpenAI, Anthropic) are in no hurry to go public • Quarterly vs. biannual earnings reporting and the case for giving management their time back • Founder-CEO vs. hired CEO dynamics and who can actually think long-term • Bitcoin's correlation with the NASDAQ and why it doesn't break the store-of-value thesis • Stablecoins, ETFs, and where the crypto regulatory environment is heading • The convergence of stocks, crypto, and prediction markets on a single platform Resources Mentioned • Apply to Long Angle HNW Community: https://www.longangle.com/apply • Subscribe to Navigating Wealth Newsletter: https://www.longangle.com/navigating-wealth-podcast • Connect with Anil Gupta on LinkedIn: https://www.linkedin.com/in/anilgupta Socials • LinkedIn: https://www.linkedin.com/company/long-angle • Twitter/X: https://x.com/LongAngleHNW • Instagram: https://www.instagram.com/longanglehnw/ • Facebook: https://www.facebook.com/longanglehnw • Youtube: https://www.youtube.com/@LongAngle Streaming • Apple Podcasts: https://podcasts.apple.com/us/podcast/navigating-wealth/id1848166539 • Spotify: https://open.spotify.com/show/074oa2E0nnJygruIqonRVG?si=4959bcd409854a6a • Amazon Music: https://music.amazon.com/podcasts/54d4ccd0-c308-4388-81ca-abfef12fadf4/navigating-wealth 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. Hosted by the founders of the Long Angle community, Navigating Wealth explores how experienced investors, founders and operators approach the real questions wealth creates — from private markets and capital allocation to business exits and life design. 01:04 - Introduction: Anil Gupta's Career in Investor Relations 02:50 - Understanding Investor Relations (IR) 05:20 - Defining Success in Investor Relations 07:14 - Private vs. Public Cap Tables 09:02 - How Institutional Investors Evaluate Public Companies 11:44 - How Retail Investors Can Access Management Insight 13:42 - Quarterly vs. Biannual Earnings 20:00 - Impact of Management Dynamics 21:48 - Direct Listings vs. Traditional IPOs 26:33 - Market Psychology & Stock Fluctuations 29:50 - Insider Buying, Share Buybacks, and What They Signal 31:37 - Why the Best Companies Are Staying Private Longer 33:07 - How to Read an Earnings Call Like an IR Professional 34:28 - The Looming Mega-IPO Wave and What It Means for Retail 39:35 - Bitcoin, Coinbase, and the Crypto Market Today 41:58 - Stablecoins, ETFs, and Where Crypto Is Heading 44:56 - The Convergence of Stocks, Crypto, and Prediction Markets 47:05 - Bitcoin Treasury Companies: Bubble Signal or Rational Access Vehicle 48:19 - Regulatory Considerations 49:13 - Learn more about Anil Gupta 49:29 - Apply to Long Angle’s Community - No Membership Fees

Proactive Genetic Testing Has a Life Insurance Problem — Sam Raha

Today we're thrilled to welcome Sam Raha, CEO of Myriad Genetics. Sam has spent 25 years at the intersection of genomics and commercial medicine.  In this conversation he explains what precision medicine actually delivers today, how AI is being embedded into diagnostic tests at three distinct levels, and why proactive genetic testing carries a real insurance risk many individuals never think to ask about. Key Topics Covered • What precision medicine is and why it is already operating at scale across cancer treatment today • How companion diagnostics work and why the business model is more durable than traditional pharma • How diagnostics companies protect their IP when human genes cannot be patented • The three layers of AI integration in diagnostics companies  • How insurance companies deployed AI to automate claim denials, and how Myriad built AI to fight back • Why individuals need to take ownership of their own health data and what that looks like in practice • What GINA covers and where it leaves individuals exposed on life, disability, and long-term care insurance • Australia's landmark legislation restricting insurer use of genetic data and what it signals for US policy • What genetic tests a proactive executive should consider  Resources Mentioned • Apply to Long Angle HNW Community: https://longangle.com/apply • Subscribe to Navigating Wealth Newsletter: https://www.longangle.com/navigating-wealth-podcast • Myriad Genetics: https://www.myriadgenetics.com • GINA — AMA Overview: https://www.ama-assn.org/public-health/population-health/genetic-discrimination Socials • LinkedIn: https://www.linkedin.com/company/long-angle • Twitter/X: https://x.com/LongAngleHNW • Instagram: https://www.instagram.com/longanglehnw/ • Facebook: https://www.facebook.com/longanglehnw 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. Hosted by the founders of the Long Angle community, Navigating Wealth explores how experienced investors, founders and operators approach the real questions wealth creates - from private markets and capital allocation to business exits and life design.

Dinner Parties Are Overrated. This 2-Hour Cocktail Party Framework Works Better - Nick Gray

Today we're thrilled to welcome Nick Gray, a two-time founder who sold a family avionics business to private equity and built Museum Hack into a multimillion-dollar experiential company before exiting operating life entirely.  After two exits, Nick found that financial freedom and social infrastructure are not the same thing. He spent years testing event formats to build a repeatable system for making friends as an adult.  He's the author of The 2-Hour Cocktail Party and writes about the friendship recession at friendshiprecession.com. Apply to Long Angle HNW Community: https://www.longangle.com/apply Daily Body Coach: https://dailybodycoach.com/navigatingwealth Key Topics Covered: • Why the structural scaffolding of adult friendship collapses after a business exit — and why financial independence doesn't replace it • The NICK framework: Name tags, Introductions, Cocktails only, Kick them out at two hours — and the specific reason each element exists • Why the dinner party is the wrong starting point for building adult friendships and what to do instead • The single language change that gets more people to show up: "Can I send you the invite?" vs. "Do you want to come?" • How Nick approached rebuilding his network from scratch after moving from New York to Austin • Nick's investment approach after exit: why passive beats active for most founders, and the 2% minimum position sizing rule he uses for high-conviction stock picks • The friendship recession by the numbers — and why it hits post-exit founders and executives the hardest Resources Mentioned: • Subscribe to Navigating Wealth Newsletter: https://www.longangle.com/navigating-wealth-podcast • Nick Gray's PersonalWebsite.org and PersonalWebsites.net • Nick Gray's Patron View donor database: https://patronview.com/ • Nick Gray's Website and Blog: https://nickgray.net/ • The 2-Hour Cocktail Party by Nick Gray: https://party.pro/book/ • Patron View Patron Leaderboards: https://patronview.com/patrons • Nick's Friends Newsletter: https://nickgray.net/signup-for-email-updates/ Socials • LinkedIn: https://www.linkedin.com/company/long-angle • Twitter/X: https://x.com/LongAngleHNW • Instagram: https://www.instagram.com/longanglehnw/ • Facebook: https://www.facebook.com/longanglehnw 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. Hosted by the founders of the Long Angle community, Navigating Wealth explores how experienced investors, founders and operators actually approach the real questions wealth creates — from private markets and capital allocation to business exits and life design.