Navigating Wealth

A bigger net worth doesn’t automatically translate into a better life. Economist Dan Altman explains why financial decisions should account for what your money actually buys you: time, experiences, relationships, and well-being.

Tad Fallows and Sriram Gollapalli is joined by Dan Altman to discuss why the value of spending can change throughout retirement, how to calculate what your free time is worth, and when saving a few dollars costs more than it’s worth.

Drawing on his book, The Best Decisions You’ll Ever Make, Dan Altman explains how economics can help you assess what a choice adds to your life alongside its financial return, from the process of decision paralysis to shifting your perspective to what matters most.

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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.

#finance #retirementplanning #personalfinance #videopodcast #podcast #buildingwealth

Tad Fallows and Sriram Gollapalli pressure-test the new wave of AI personal assistants: Instinct, Meta's Muse, OpenAI's Dots, Town and GrokBot. Sriram has spent a month running Instinct inside WhatsApp with access to his Gmail and calendar, and he walks through what it has handled so far: prepping the call to move his daughter's doctor's appointment, emailing a teacher while he brushed his teeth, pushing a vendor into a full refund on a forgotten app subscription, and finding a garage-floor quote about 30 percent cheaper than the first one. Tad, who still uses Gemini as a search engine, presses on the trust questions: what you hand over to get the help, which company you trust with it, and where the line sits on your credit card and your bank accounts.

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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.

Learn what an AI personal assistant can take off your plate today, and what it costs you in access to get there. Treat it like a new hire: give it context, start with low-stakes tasks, and widen its permissions only as it earns them.

Most people think of AI as a chatbot you visit, but these assistants live inside your messages and your inbox and act on your behalf. If you have been using Gemini or ChatGPT as a search engine, this conversation shows what changes once an agent can read your email, manage your calendar and contact vendors for you, and what you give up when it can.

We cover the two setup prompts Sriram brought home from a Long Angle retreat session, the garage quote that came back about 30 percent cheaper, the 657 newsletter subscriptions his assistant found in his inbox, the feature that lets his assistant coordinate with his wife's, where he draws the line on payment information and bank accounts, and the often-overlooked security step of routing two-factor codes to a second phone number that nobody else knows.

Subscribe for weekly conversations on wealth and the decisions that come with it, and comment below if you want a walkthrough of the setup prompts Sriram used.

#aiassistant #aiagents #productivity #dataprivacy

How does private placement life insurance work, and when does it beat a taxable account? David Valcourt, VP of Business Development at Financial Architects Partners and a life insurance broker with nearly 20 years in the private placement market, returns for part two with hosts Tad Fallows and Matt Shechtman.

In this conversation, David explains what PPLI is (a protection product whose engine is the investment inside it), walks through the math of trading a 5% annual tax bill on private credit and hedge funds for a smaller fee bill, and makes the case for what belongs inside a policy and what does not, starting with the S&P 500. He covers why so many whole life buyers end up disappointed, who the players are (broker, carrier, reinsurer, investment manager, and the insurance dedicated fund or separately managed account), why the IRS investor control doctrine means you cannot pick the holdings, what the insurance itself costs, what happens if a carrier fails and how a 1035 exchange works, and how borrowing against the policy really works, including why it is not free money.

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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.

Learn how private placement life insurance works from a broker who places it: what goes inside the policy, what the insurance and the fees cost, why you cannot direct the investments, how the policy survives a carrier failure, and how policy loans give you access to the money during your life.

Most people hear "life insurance" and think of whole life and a disappointing dividend. This conversation makes a different case: for investors already holding tax-inefficient assets like private credit and hedge funds, the policy is a wrapper, and the question is whether the tax you save is worth the fees you pay.

How do you beat decision fatigue and decide when the data is incomplete? Former CIA analyst Rupal Patel spent six years briefing the four-star general running the Afghanistan war, sometimes contradicting his own intelligence apparatus. With host Sriram Gollapalli, she walks through how analysts cut signal from noise, why the perfect data set does not exist, and how the same decision-making framework carried her from the CIA to business school to building a real estate business on an 18-month runway — a story she tells in her book From CIA to CEO.

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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.

Learn how a CIA analyst makes high-stakes decisions with incomplete information: separate signal from noise, name the gaps out loud, and decide when enough is enough instead of waiting for certainty.

Most people believe more research means better decisions. This conversation makes the opposite case: past a point, more inputs feed decision fatigue and analysis paralysis, and the discipline that matters is knowing what to ignore.

We cover the briefing style that won over a skeptical general, the 18-month runway behind her real estate business, treating family investors like institutions, rebuilding leaner after COVID, her first keynote in Spanish, an allocation of index funds and real estate, and the three-priorities exercise she uses against decision fatigue.

Subscribe for weekly conversations on wealth and decision-making, and comment below if you want a deeper dive on the three-priorities exercise.

#decisionmaking #decisionfatigue #cia #leadership

Where do millionaires keep their money? Tad Fallows and Matt Shechtman break down Long Angle's survey of 165 high-net-worth households grading every financial product they use: the most-carried credit cards rank near the bottom of their categories, brokerages beat banks at banking, and spreadsheets are still the number one way wealthy households track their portfolios.

The full 2026 High-Net-Worth Financial Products: Benchmark Report is available at https://www.longangle.com/research.

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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.

Learn where high-net-worth households keep, bank, track, and protect their money. Stop assuming the most popular financial products are the ones their users would recommend.

Most people think the biggest banks and best-known cards are where wealthy families keep their money, but this survey shows the opposite: Fidelity and Schwab earn banking recommendation scores the big banks do not come close to, and the most-carried credit cards rank near the bottom of their categories.

We cover credit cards, banking, brokerages, portfolio tracking, mortgages, and insurance, including the umbrella policy math many households skip, roughly $10 million of coverage for under $3,000 a year, and the revocable-trust distribution move a bank's own mortgage broker suggested for underwriting.

Subscribe for weekly personal finance breakdowns, and comment below if you want a deeper dive on the trust-distribution mortgage strategy.

#personalfinance #investing #millionaire #banking

Is AI a bubble? Tad Fallows and Sriram Gollapalli break down how to invest in AI in 2026 — starting with the warning Warren Buffett gave the tech elite at Sun Valley in July 1999: a transformative industry and a rewarding investment are not the same thing. Eighteen months later the dot-com crash proved him right, and his warning is being repeated today. Ten stocks now make up nearly 40 percent of the S&P 500, and $18 of AI infrastructure spending goes out for every dollar of AI software revenue. The greatest buildout in market history, or the most expensive echo of 1999?

This conversation started as a thread inside Long Angle: a member asking whether he'd missed the Anthropic trade. Tad and Sriram follow the AI money through the stack — natural gas and power stocks, data centers, NVIDIA and the revenue-recognition accounting behind chip profits, frontier models and where vendor lock-in lives — and what each of them is buying today. They close with how private investors reach pre-IPO deals like the Anthropic SPV, and the fee traps to check before you invest.

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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.

Learn whether the AI boom is a bubble and where the money goes whoever wins. Stop trying to pick the winning model company and look at the layers underneath instead.

Most people think playing the AI trade means betting on a frontier model, but if you own an S&P 500 fund, you have already made the AI bet - ten stocks are a record share of the index. The conversation walks through the picks-and-shovels layers trading at reasonable multiples: natural gas and power, chips and networking, and the revenue-recognition disconnect flattering today's earnings.

We cover the $30 trillion question both Anthropic and SpaceX have put in front of investors, including what each host is buying today and the two checks that keep private-market investors from getting burned: are you on the cap table, and what are the total fees? If you want exposure to the next Anthropic without the lottery-ticket odds, this breakdown shows how members approach it.

Subscribe for weekly conversations on navigating wealth, and comment below if you want the full list of infrastructure plays discussed in this episode.

#aibubble #investing #wealthmanagement #artificialintelligence

Tad Fallows breaks down the best credit cards for high-net-worth spenders: a set-it-once system built on asset thresholds instead of annual fees, worth more than $20,000 a year to him, tax-free, with no signup bonuses or rotating categories to manage.

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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.

Today we're thrilled to welcome Dave Valcourt, VP of Business Development at Financial Architects Partners, part of NFP, one of the largest insurance brokers in the country. Dave has spent almost twenty years in life insurance as an independent broker who supports the full spectrum of policies, from term life to whole life to private placement life insurance, and canvasses more than twenty carriers to match each product to each client's situation.

In this conversation, Dave explains where the industry's pushy reputation comes from and why commissions on a traditional permanent policy can reach 90% of a first-year premium, maps what term, whole life, GUL, IUL, VUL, and PPLI are each built for, and walks through premium financed life insurance - the strategy where a private bank lends the premium directly to a trust, so the money arrives without gift tax and whole life cash value serves as collateral at a 95% advance rate.

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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.

Today we’re thrilled to welcome Kartik Singapura, partner and trial attorney at Bell Nunnally. We discuss a working litigator’s view of AI tools for lawyers: what they genuinely speed up, where they still fail, and why he calls AI an average intelligence.

The conversation covers how AI inverted the way lawyers build a case, whether the billable hour survives, and what happens when clients arrive with ChatGPT legal advice that is confident but wrong.

Kartik also answers the question on every desk - will AI replace lawyers? - and shares his warning about what you type into a chatbot.

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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.

Today we’re thrilled to welcome David Stein, former chief investment strategist at institutional advisory firm FEG and host of the Money for the Rest of Us podcast. David spent close to two decades advising endowments, foundations, and institutional clients before turning to teaching individual investors how markets work and building the market analysis tool Asset Camp.

In this conversation, David makes the case that a 60/40 portfolio is too risky when the goal is preserving generational capital, explains how the S&P 500 has drifted toward a concentrated, AI-heavy benchmark trading near record valuations, and walks through his own “asset garden” - a portfolio of roughly 20% stocks alongside gold, crypto, private capital, preferred stocks, closed-end funds, and catastrophe bonds.

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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.

Evergreen funds promise private markets access without decade-long lockups. StepStone's Michael Elio covers semi-liquid fund liquidity, secondaries pricing and how to evaluate a fund before you buy.

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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.

Alex Branton runs NAV lending at Nodem Capital, one of the few firms financing the illiquid end of private wealth, where he sees roughly 150 portfolios a year and underwrites about 20.

He breaks down why banks won't lend against private equity and venture no matter how large the portfolio, and how to weigh borrowing against a private book versus selling it at a steep secondary discount.

If you're holding illiquid assets you can't easily sell, he lays out what separates a facility worth taking from one that quietly turns debt into equity risk.

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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.

Max Artz leads the search fund strategy at Peterson Partners, where he screens roughly 300 searchers a year to back 10 to 15.

He breaks down why this asset class has returned in the mid-30% range for three decades without compressing, and how the best searchers win deals against buyers writing bigger checks.

If you're weighing search as an allocation or the operator path yourself, he lays out what separates a sponsor worth backing from one riding the trend.

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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.

Today we welcome Emila Damjanovic and Evan Skorpen, Partners at Lead Edge Capital, a growth equity firm with 100+ company partnerships and 60+ exits. The conversation covers how growth equity works, why software cash margins have tripled while valuations compressed, and how to identify which software businesses are actually durable when AI is reshaping the category.

This episode gives investors a cleaner way to evaluate software positions right now.

🔔 Please Subscribe and Hit the Bell: https://www.youtube.com/@NavigatingWealthPodcast?sub_confirmation=1

Discover More From Long Angle
👉 YouTube: https://www.youtube.com/@NavigatingWealthPodcast
👉 Beyond Wealth Newsletter: https://langle.co/bwnews
👉 Research & Studies: https://www.longangle.com/research
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Resources & Links
👥 Become a Member: longangle.com/navigatingwealth
📤 Get Episode Release Notifications: https://www.longangle.com/navigating-wealth-podcast
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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.

He spent nearly a decade at Meta, got laid off, looked at his accounts, and realized he never had to go back. Three years into semi-FIRE, Andre Nader writes the FAANG FIRE Substack — helping tech workers turn equity compensation and high income into financial independence and optionality.

In today's episode, Andre breaks down the full FAANG FIRE framework: how to calculate your enough number using the 33x rule, why your RSU selling strategy is probably emotional rather than mechanical, the tax misconception that keeps tech workers holding stock longer than they should, and why the biggest obstacle to FIRE isn't the math — it's giving yourself permission to spend.

🔔 Please Subscribe and Hit the Bell: https://www.youtube.com/@NavigatingWealthPodcast?sub_confirmation=1

Discover More From Long Angle
👉 YouTube: https://www.youtube.com/@NavigatingWealthPodcast
👉 Beyond Wealth Newsletter: https://langle.co/bwnews
👉 Research & Studies: https://www.longangle.com/research
━━━━━━━━━━━━━━━━━━━━
Resources & Links
👥 Become a Member: longangle.com/navigatingwealth
📤 Get Episode Release Notifications: https://www.longangle.com/navigating-wealth-podcast
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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.

The highest inflation in three years has the market pricing in rate hikes. A 38-year Wall Street monetarist thinks that's exactly backwards, and that the Fed is clear to cut.

Today we welcome Jay Hatfield, founder, CEO, and portfolio manager at Infrastructure Capital Advisors, where he runs nine income ETFs. A CPA and Wharton-trained monetary economist with 38 years on Wall Street, Jay makes the contrarian case that the recent inflation spike is a near-term oil-price illusion about to reverse, not the start of a wage-price spiral.

He breaks down why he ignores the labor report, why deficits and strong employment don't drive inflation, and the four or five indicators he actually uses to forecast rates and the business cycle.

This conversation is for investors trying to separate signal from consensus on interest rates, oil, the AI earnings boom, and where to position before the next move. Jay also walks through his DCF on the SpaceX IPO and the "Musk premium" that could push it far above fair value.

🔔 Please Subscribe and Hit the Bell: https://www.youtube.com/@NavigatingWealthPodcast?sub_confirmation=1

Discover More From Long Angle
👉 YouTube: https://www.youtube.com/@NavigatingWealthPodcast
👉 Beyond Wealth Newsletter: https://beyondwealthnewsletter.com/
👉 Research & Studies: https://www.longangle.com/research
━━━━━━━━━━━━━━━━━━━━
Resources & Links
👥 Become a Member: longangle.com/navigatingwealth
📤 Get Episode Release Notifications: https://www.longangle.com/navigating-wealth-podcast
━━━━━━━━━━━━━━━━━━━━
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.

Today we're thrilled to welcome Kristin Keffeler, Chief Learning Officer at the JFG Family Office, co-author of Wealth 3.0, and one of the leading practitioners in rising generation development.

Kristin has spent 20 years working with families navigating the psychological and structural challenges of raising children with significant inherited wealth — and is herself a second-generation inheritor who lived the dynamics she now helps others understand.

In this episode, Kristin walks through the well-intentioned messages that stall a child's development, the trust structures that accidentally produce dependent adults, and the disclosure decisions that parents get wrong in both directions.

She introduces the trampoline framework for thinking about inherited wealth — why it lifts children higher when structured correctly, and why it sinks them lower than if they had nothing when it isn't.

Key Topics Covered

• Why the message "I earned this so you don't have to" is more damaging than the wealth itself
• The trampoline framework: how inherited wealth amplifies effort or replaces it
• False scarcity vs. permissiveness — why both extremes backfire
• Self-determination theory applied to parenting: autonomy, competence, and relatedness as a diagnostic framework
• The age-by-age disclosure framework — what to share, when, and what to build before you share anything at all
• The four biggest mistakes wealthy parents make with their children
• The apprenticeship model for trust design — a staged path from beneficiary to co-trustee across the 20s and 30s
• What to include in a letter of wishes that actually works
• How overly controlled trusts can infantilize adult children well into their 60s
• Spending modeling: housekeepers, travel, and what to be thoughtful about as children observe family lifestyle

Episode Resources

• Apply to Long Angle HNW Community: http://longangle.com/navigatingwealth
• Subscribe to Navigating Wealth Newsletter:https://www.longangle.com/navigating-wealth-podcast
• Connect with Kristin Keffeler on LinkedIn: https://www.linkedin.com/in/kristin-keffeler-msm-mapp-245a21/

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.

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

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.

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