Podcast Summary: Educational Alpha — S3: Conversation with Matt Shechtman and Tad Fallows, Long Angle (Nov 26, 2025)

Main Theme and Purpose

This episode of Educational Alpha, hosted by Bill Kelly, explores wealth management and peer learning with guests Matt Shechtman and Tad Fallows, co-leaders of Long Angle—a private community for high net worth individuals. The conversation covers their entrepreneurial backgrounds, the challenges of managing significant wealth post-liquidity event, peer-driven approaches to investing in private markets, collective access strategies, and the importance of health and wellness (including mental health) in high net worth circles. They dive into peer learning, asset allocation, mitigating single-asset risk, and navigating estate and tax planning complexities.

Key Discussion Points & Insights

1. Introductions & Backgrounds

• Tad Fallows: Bootstrapped and exited a software company, thrust into complex wealth management post-exit.
  • “On one day went from having very little money to having a fair amount of capital to manage.” [02:32]
• Matt Shechtman: From real estate law to founding/exiting health & wellness businesses, then focused on portfolio diversification.
  • “I was heavily concentrated in real estate and looking for…diversification…started working with some family offices and that is where the entire asset allocation bundle came into play.” [03:58]

2. Responsible Access to Alternatives

• Alternative Investment Gatekeeping:
  • Current accreditation requirements are blunt and exclusionary, but removing them causes risks (sophistication, suitability).
  • “The current rules…are pretty arbitrary and have been fodder for a lot of debate on whether or not that’s the right tool…” (Matt, [05:37])
  • Long Angle’s high net worth bar ensures sophistication; access is responsibly gated.

3. Health, Wellness & Mental Health

• Community as a Mental Health Support:
  • Demand for belonging is intertwined with mental wellness, especially after exits or life events (e.g., COVID).
  • “Even for those that are highly successful…mental health…is probably one of the number one things that we deal with in the community.” (Matt, [10:05])
• The Impact of Technology on Children:
  • Limiting children’s exposure to tech/social media is crucial.
  • “The better somebody knows technology, the less they want their kids having exposure to it…” (Tad, [12:45])

4. The Long Angle Community: Purpose & Approach

• Creating a Peer-to-Peer Safe Space:

  • Target demographic: first-generation high or ultra-high net worth, sub-family office.
  • Focus: candid conversations about complex wealth, estate, and life issues—free from solicitations or hidden sales pitches.
  • “Just people connecting—‘I’m having this challenge, my cousin’s asking for money… what do you do?’” (Tad, [16:32])

• Collective Access to Alternatives:

  • Members pool resources to access private funds with high minimums.
  • Peer due diligence is invaluable: “There’s not an investment out there that somebody doesn’t have an unbiased opinion on…” (Matt, [21:12])
  • “Basically allows people to get…institutional caliber access to alternative assets, but on a person choosing on a case by case basis…” (Tad, [17:45])

5. Asset Allocation, Concentration & Diversification Strategies

• Surveys & Member Behavior:

  • Members generally conservative with leverage; little debt; focus is on equity risk, not smoothing returns.
  • “The portfolios are within less than a percentage point different from the members who work with a wealth manager and those who don’t.” (Tad, [26:09])
  • De minimis bond allocations; heavily weighted to equities (public & private), alternatives, real assets, crypto.

• Relationship with Wealth Managers:

  • Many self-manage, but acknowledge value in using managers for estate/tax coordination and behavioral coaching.
  • “I think that is crucially important [estate planning]…the wealth manager, that’s probably in that category of a good reason to use one if you don’t want to figure it all out yourself.” (Tad, [28:00])

• Managing Concentrated Wealth Post-Liquidity Event:

  • Use of donor-advised funds, exchange funds, and direct indexing to mitigate single-stock/tax risk.
  • “The risk that people are probably most interested in hedging is that single asset risk.” (Tad, [35:39])

6. Risk, Hedging, & The “40” in 60/40 Portfolios

• Addressing Volatility and Hedging:

  • For those with significant wealth, sequence risk and drawdowns are less critical—focus is on non-correlated strategies, real assets, private equity, not “hedging” in the traditional sense.
  • “When you’re getting past the 10 million plus…you don’t need to be pulling from your assets…in the event of a significant drawdown…” (Matt, [32:09])
  • Preferences toward non-correlated assets (e.g., industrials, litigation finance).

• On the “Credit” Side of Asset Allocation:

  • “If anything, people are quibbling on the 40…” (Matt, [48:15])
  • Private credit is rising to prominence versus traditional fixed income; manager selection is critical.

7. Inflation Concerns

• Why Bonds Feel “Uninteresting”:

  • “If the bond’s yielding 4% nominally, I’m basically guaranteed over the long term to get 4%. And that’s just not interesting.” (Tad, [40:49])
  • Real assets and equity risk are attractive inflation hedges.

• “During COVID I was very much in this thesis of, hey, the government’s spending money like a drunken sailor and I can borrow money at 2%—why on earth would I not lock in as much 30-year fixed debt as I possibly can and turn around and invest that in real assets…” (Tad, [41:15])

8. Long Angle’s Access Model

• Joining the Community:

  • No membership fees; application & peer interview required.
  • Seeks diversity—industry, geography, demographics.
  • “Really people who are coming out with a peer-to-peer learning mindset, not seeing this as a place to attract new clients.” (Tad, [44:20])

• Role in the Marketplace:

  • Unique blend: not a direct competitor to any single group, but overlaps with several.
  • Open benchmarking reports and research for public consumption.

9. The Democratization of Alternatives & Cautions

• Nuanced Views on Widespread Access:
  • Private markets have delivered for institutions due to illiquidity, complexity, and information advantages.
  • “Part of the reason that some people have had very good success…is because of this information premium and the complexity premium…that is firmly not true in the private markets.” (Tad, [45:53])
  • Caution against widespread retail access without proper diligence/education.

Notable Quotes & Memorable Moments (with Timestamps/Speaker)

• On sudden wealth and life changes:
  “On one day went from having very little money to having a fair amount of capital to manage.”
  — Tad Fallows [02:32]

• On mental health and the role of community:
  “Even for those that are highly successful…mental health…is probably one of the number one things that we deal with in the community.”
  — Matt Shechtman [10:05]

• On peer learning’s power:
  “Just people connecting—‘I’m having this challenge, my cousin’s asking for money… what do you do?’”
  — Tad Fallows [16:32]

• On investment diligence in the Long Angle network:
  “There’s not an investment out there that somebody doesn’t have an unbiased opinion on…”
  — Matt Shechtman [21:12]

• On asset allocation and risk tolerance:
  “If I think I’ve got a 50 year horizon ahead of me, I don’t want to just settle for 4% returns. I want to get 10% equity like returns for the next 50 years because it’s going to compound to a far different number.”
  — Tad Fallows [39:15]

• On inflation as top risk:
  “If there’s anything that can really be destructive to wealth, it is inflation.”
  — Bill Kelly [40:08]

• On the 60/40 portfolio viability:
  “If you go all the way back to the 1930s, 100 years, you cannot find a rolling 10-year period where that 60/40 was not in the positive territory.”
  — Bill Kelly [47:22]

Noteworthy Segments (Timestamps)

• [02:27] Tad and Matt’s entrepreneurial journeys and personal transitions to wealth management.
• [05:37] The issue of access, regulation, and responsible participation in alternatives.
• [09:00] Mental health, COVID, and the role of community for high net worth individuals.
• [15:29] Deep dive into Long Angle’s membership, purpose, and unique “no solicitation” ethos.
• [17:45] Mechanisms for collective investment in alternatives—access, member diligence, manager selection.
• [23:44] Discussion of asset allocation survey: conservative leverage, preference for equity, approach to wealth managers.
• [35:39] Detailed strategies for concentrated risk: exchange funds, direct indexing, charitable giving.
• [40:49] Views on inflation, real asset bias, and borrowing to invest in inflationary environments.
• [43:07] Joining Long Angle—process, philosophy, how to apply.
• [45:49] Democratization of alternatives: information premium, risks, and public policy questions.

Closing Observations

• Peer empowerment is central: Long Angle’s success lies in facilitating candid, bias-free information sharing among accomplished individuals facing similar life transitions.
• Alternatives are a means to diversification, not a panacea: Access is valuable, but caution and collective wisdom are essential.
• Wealth beyond investing: Issues of health, wellness, intergenerational wealth management, and peer support are as pressing as asset allocation.
• Manager selection and due diligence is paramount in private markets—don’t just “fall in love with yield.”
• The 60/40 isn’t dead, but its components are evolving—the big debate is on “the 40,” i.e., the credit/yield side.

For those interested in learning more or applying to Long Angle, visit longangle.com for public reports and information on the application process.