Navigating Wealth

Latest Episodes:

How Evergreen Funds Pick Winners in Any Market - Michael Elio Jul 22, 2026

Show notes

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.

Illiquid Assets You Can't Sell? Borrow Against Them - Alex Branton Jul 15, 2026

Show notes

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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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
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Search Funds: Winning the Deal Without the Highest Offer - Max Artz Jul 08, 2026

Show notes

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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How Growth Equity Firms Pick Software Winners in an AI Market — Emila Damjanovic and Evan Skorpen Jul 01, 2026

Show notes

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.

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He Turned His FAANG Salary Into Early Retirement - Andre Nader Jun 24, 2026

Show notes

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.

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Market Rate Hikes? This 38-Year Monetarist Disagrees - Jay Hatfield Jun 17, 2026

Show notes

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.

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Discover More From Long Angle
👉 YouTube: https://www.youtube.com/@NavigatingWealthPodcast
👉 Beyond Wealth Newsletter: https://beyondwealthnewsletter.com/
👉 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
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The Unexpected Parenting Mistakes That Arrive With the Money - Kristin Keffler Jun 10, 2026

Show notes

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: 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/

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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.

Why The Best Philanthropy Doesn't Start With A Check - Brent and Kyle Pease Jun 03, 2026

Show notes

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
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#KylePeaseFoundation #Nonprofit #Philanthropy #CharitableGiving #NonprofitLeadership #NavigatingWealth #LongAngle #SocialImpact

The Controversial Asset Class Historically Outperforming the Stock Market - Jason Bertoldi May 27, 2026

Show notes

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/

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

Earnings Calls Decoded by a Former Coinbase IR Executive - Anil Gupta May 20, 2026

Show notes

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

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

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