May 22, 2026 · 57m · sourcery
CIO of Marc & Ben's Multi-Family Office: SpaceX IPO, Anthropic & OpenAI · Sourcery with Molly O'Shea
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In this episode of Sourcery, host Molly O'Shea interviews Michel Del Buono, Chief Investment Officer at a16z Perennial, to examine comprehensive wealth management strategies for founders facing pre-liquidity events. The discussion covers tax-loss harvesting, trust structures, secondary market SPVs, private credit risks, real asset depreciation, and wealth psychology.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Molly holds 28.2% of the talking time here. How this is scored →
Molly as informed peer 3.3 Guest teaching 5.6 Guest disagreement 1.3 Molly pushing back 1.3
speaking balance: gold is Molly, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 23:26 Qualified purchasers cannot complain about unfair contracts
Michel firmly dismisses any notion of unfairness in bad SPV deals, arguing that accredited investors explicitly waive regulatory protections when signing private agreements.
Hardest push from Molly ▶ 34:10 Molly defends VCX cap table structureMolly pushes back against Michel's skepticism regarding public venture wrappers by explicitly clarifying that VCX holds direct cap table positions rather than layered SPVs.
Biggest teaching moment ▶ 49:24 Masterclass on real asset tax sheltering and step-up in basisMichel explains how depreciation offsets active cash flows in real assets and how the step-up in basis eliminates accumulated capital gains upon generational transfer.
Molly holds their own ▶ 36:40 Molly introduces primary source data center energy bottlenecksMolly demonstrates strong industry expertise by citing direct operational insights from ExoWatt regarding stalled hyperscaler and data center infrastructure buildouts.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Molly as informed peer | Guest teaching | Guest disagreement | Molly pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome and Pre-Liquidity Event Framework | 3 | 6 | 1 | 1 | Molly frames general questions about pre-liquidity planning and what happens if a founder does not optimize. Michel takes the lead systematically breaking down the three pillars of pre-liquidity (trusts, tax loss harvesting, donor-advised funds) and explaining the baseline math of capital gains taxation. | |
| QSBS Tax Exclusion and Trust Stacking Strategies | 2 | 7 | 2 | 1 | Molly asks how QSBS stacking works while openly admitting lack of familiarity with the legal nuances. Michel gently educates her on QSBS dollar limits, trust multiplication, and the psychological hurdles families face when deciding inheritance distribution terms. | |
| Managing Concentrated Equity Positions Post-Liquidity | 4 | 6 | 1 | 2 | Molly prompts Michel on managing concentrated positions, secondary sale dynamics, and nested SPVs. Michel breaks down L1, L2, and L3 structures, hidden carry hurdles, and loan-pledge risks in private secondary transactions. | |
| Sponsor Break: Brex and Turing | 2 | 5 | 2 | 0 | Following the mid-roll ad read, Molly references a fraud case involving an SPV manager absconding with capital. Michel explains the cold reality of qualified purchaser exemptions and the lack of regulatory protection in private custom contracts. | |
| Macro Risks, Private Credit, and BDC Redemption Gates | 3 | 7 | 2 | 1 | Molly inquires about broad macro risks and headline liquidity panics. Michel explains BDC redemption gates, distinguishes semi-liquid structures from evergreen funds, and emphasizes that illiquid underwriting details were clearly telegraphed in fund documents. | |
| Portfolio Construction and Institutional Endowment Allocations | 4 | 5 | 1 | 2 | Molly demonstrates domain knowledge by citing Yale lowering its allocation to venture capital despite retail demand rising. Michel agrees with the observation and details endowment cash flow requirements and university operational liabilities that dictate liquidity rebalancing. | |
| Retail Venture Vehicles, Public Tickers, and Valuation Risks | 5 | 4 | 1 | 2 | Molly brings up public closed-end venture vehicles like VCX and AngelList retail products, noting direct cap table access. Michel probes the implied valuations, nested fees, and valuation premiums retail investors pay when chasing AI FOMO. | |
| AI in Private Equity Operations and Data Center Infrastructure | 5 | 4 | 1 | 2 | Molly brings direct insight from her interview with an energy provider to data centers to question the reality of hyperscaler buildouts. Michel builds on her point, distinguishing operational PE AI implementations from physical power bottlenecks and capex depreciation rules. | |
| Global Tax Havens, Expat Regimes, and Property Taxes | 4 | 5 | 2 | 2 | Molly brings up New York pied-a-terre taxes and London neighborhood hollowing mentioned on All-In. Michel contextualizes the tax impact, contrasting local real estate surcharges with structural UK non-dom inheritance tax overhauls. | |
| Sponsor Break: VCX, Public, Merge, and Deel | 2 | 6 | 1 | 1 | Following the sponsor read, Molly asks how to evaluate wealth managers across disciplines. Michel reiterates that standard legal or accounting silos fail to integrate tax-loss harvesting with estate planning, requiring multidisciplinary cross-examination. | |
| Tax-Shielding Real Assets: Real Estate and Oil Wells | 3 | 7 | 1 | 1 | Molly expresses surprise at investing in oil wells, prompting Michel to explain depreciation tax credits across real assets, passive loss limitations for non-real estate professionals, and step-up in basis upon death. | |
| Wealth Psychology, Spending Rates, and Cultural Inheritance | 3 | 5 | 1 | 1 | Molly references Sam Parr's viral wealth tier comparisons and asks about private jet ownership and spending discipline. Michel explains European forced heirship rules, business asset write-offs for aviation, and wealth depletion psychology. |
Statements from this episode (23)
Del Buono: Pre-Liquidity Planning Rests on Trusts, Tax Investments, and Philanthropy
“So there's kind of three elements
To preparing yourself for a liquidity event, right?
Structuring your trust and estate, thinking about how to sort of make key investments that help offset taxes to some degree, and then donating into a donor advice fund or som…”
Del Buono: Donor-Advised Funds Separate Tax Timing From Philanthropic Decisions
“The beauty of the donor advised fund is that you can sort of detach your decision when to give with your decision of when to sort of tax optimize, right?
So you can donate things into a DAF and immediately get a tax benefit, but if you're young and still worki…”
Attorneys and CPAs ignore tax-loss strategies that rival complex trust structures
“Where I find that people have difficulty is you hire attorneys, right, and they're going to tell you everything about, or CPAs, about these trusts, but they're not going to have the knowledge
To compare that and contrast that to an investment strategy that gen…”
Del Buono: Family decisions, not trust mechanics, stall wealth planning
“If you don't have those basic things thought out, trying to structure the trust itself is not the difficult bit. It's these things you define inside a very difficult bit.”
Wealth managers push diversification strictly to earn fees on founder stock
“Wealth managers, asset managers, It's very self-serving for them to say, hey, you should liquidate everything because obviously they can't, they're not going to charge you fees on your concentrate position. It's your stock. You brought it to the table, but the…”
Winning concentrated startup stock usually continues to perform well post-liquidity
“History has shown that hanging onto your stock Generally speaking, not always. There are counter examples, of course, to everything. Generally, you know, that stock that got you to the liquidity point will probably continue to do pretty well.”
Del Buono: Most founders should keep company stock while actively engaged
“But I'd say the vast majority of people should keep it for a while at least as long as they're engaged in the company, right?”
Nested L2 and L3 SPVs introduce severe, compounding counterparty risk
“So you see things L one, L two, you even see L three nested structures each time you're further and further away from the stock. And so there's more and more risks that you don't get, You know, what you thought you would, right? Because who's to say that the o…”
Del Buono: Secondary SPVs frequently charge 1/10 or 2/20 fees at marked-up valuations
“The other thing, of course, is that people layer in a lot of fees, carry, so it's not unusual to see one in 10, two in 20 type structures, or a five percent transaction fee, and often it's not done at the last round. It's done a significant, you know, increase…”
Pre-IPO secondary SPVs take carry from the first dollar without hurdles
“And in some spaces, like in private equity, carry usually has a minimum return before the carry accrues to the person. So, you know, might have a six, seven, eight percent Return to the investor before the SPV owner gets the carry, but in these situations I've…”
Del Buono: In private investing, signed contracts override notions of fairness
“Whenever you're doing a private investment, the contract you know, you're sort of excluded from the regulatory oversight by saying that it's a special contract only for qualified people that don't, that meet certain income thresholds. So those contracts are cu…”
Del Buono: Semi-liquid evergreen funds can gate redemptions below five percent
“Some evergreen structures have what's called this sort of semi-liquid character, so that every quarter, the company that's running this structure will say, hey, if five percent of the total investors redeem, we'll meet that, but if it's more than that, we won'…”
Del Buono: Young investors can hold up to 100% alternative assets
“If it's for a very young person, it's okay to have 80, 9000% alternatives, because they don't need the cash immediately. So let the stuff grow, you know, at the highest risk possible.”
Del Buono: Weak distributions affect all private asset classes, not just venture
“In the last few years, the distributors have been pretty weak from all private asset costs. It's not specific to venture.”
O'Shea: AngelList launched a private market fund for $500 minimums
“AngelList just came out with their private market fund that you can buy into for just 500 dollars today.”
Retail private market funds risk massive fee leakage through layered SPVs
“You just have to look at the underlying pieces and understand them, except that there's the additional complexity. How did they get this thing? Is it through an SPV? Is it through an L two SPV? What did they pay for that? How much of the sort of return is goin…”
Del Buono: Clients are experiencing a 'fever' demanding direct private investments
“More and more people want access to these directs. They're clamoring for it. And they'll come and they'll say, oh, I've got these, you know, these six different things I'm looking at. What do you have? Let me compare across this. It's a complete fever around t…”
Taxable investors can immediately depreciate 100% of data center capital expenditures
“The beauty of the recent tax changes is that for a taxable investor you have accelerated depreciation on data centers, so you can depreciate a hundred percent of your capex immediately and get a huge tax benefit. So there's some tailwinds to the sector because…”
Del Buono: Several countries offer flat-tax regimes of $100k–$200k annually
“A lot of, so a lot of these countries have sort of a flat tax. You pay a hundred or 200,000 dollars a year, and then that's it for 10 years, 20 years, whatever it might be.”
UK expat tax reform triggered flight by exposing full global balance sheets
“In London though when they sort of got rid of the expat sort of benefits and a hundred percent of your wealth could come under the 40% inheritance tax they have in the UK, that caused the problem because the entire balance sheet of someone's life or worth woul…”
Del Buono: Standard Funds Skip Tax Structuring Due to Non-Taxable Clients
“A lot of the standard funds out there don't do the structuring because most of their clients are not taxable.”
Real asset depreciation and basis step-up can completely shield generational taxes
“If structured properly, you can offset Almost all the income from the property. And then because of something called a step up in basis, a death when you sell that asset after you pass away, you don't owe tax on that either. So you, along the way, all the inco…”
Del Buono: Business private jets can be depreciated like real estate
“If you use it for business purposes now you can sort of depreciate and take advantage of the same tax credits that you do with real estate and oil wells. Right. But you have to be able to prove that you, it was used for business purposes and all that.”