Mechanics of Money
Stop saving. Start allocating.
Mechanics of Money is the technical manual for high-net-worth individuals moving from "High Earner" to "Sophisticated Allocator."
Hosted by Sam Silverman (Silverman Capital), this show strips away the "get rich quick" hype to focus on the operational and financial mechanics of wealth preservation. We sit down with founders, fund managers, and tax strategists managing billions in assets to decode exactly how the ultra-wealthy structure their capital.
We cover:
• Private Markets: Deep dives into Multifamily Syndications, Private Credit, and PE.
• Tax Strategy: Advanced frameworks like 1031 Exchanges, Bonus Depreciation, and Opportunity Zones.
• Risk Management: How to vet operators and protect your downside.
Whether you are looking to place your first $50k into a syndication or managing an 8-figure family office, we provide the blueprint.
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Mechanics of Money
Why a Full-Time LP Is Still Holding Cash | Jeremy Roll
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Putting capital to work can feel productive. But when a private deal locks that capital away for five years - and possibly ten - patience may be the more active decision.
Jeremy Roll is President of Roll Investment Group and a full-time passive investor who began moving his savings from public markets into cash-flowing private investments in 2002. He has participated in more than 200 LLCs over that period and remains invested in more than 60 today.
Jeremy joins Sam Silverman to explain why he has become more defensive despite decades of experience in real estate syndications and alternative investments. Their conversation moves from Jeremy's path out of Disney and Toyota into full-time LP investing to the practical questions investors should ask about liquidity, cycle timing, sponsor history, leverage, fees, and alignment. Jeremy also explains his personal thesis on AI spending and the next market reset, while repeatedly distinguishing his approach from financial advice.
In this conversation:
- How cash-flowing investments allowed Jeremy to leave the corporate world
- Why he would not recommend his original 100% illiquid allocation
- How technology and public solicitation changed private real estate investing
- Why a business exit can create pressure to reinvest too quickly
- How Treasury liquidity changes the opportunity-cost calculation
- Why private-market returns must compensate investors for illiquidity
- What Jeremy wants to see before redeploying capital
- Why a downturn can give LP capital more negotiating power
- How a sponsor's foreclosure can affect future borrowing costs
- What conservative underwriting and underpromising look like in practice
- How acquisition fees, AUM fees, and deal volume can weaken alignment
- Which real estate sectors Jeremy finds more predictable
- Why new LPs should learn one asset class before diversifying
- Why Jeremy would rather enter a real estate recovery late than catch a falling knife early
Topics covered: passive investing, real estate syndications, limited partners, alternative investments, market cycles, liquidity, Treasury bills, sponsor due diligence, underwriting, illiquidity premium, syndication fees, AI infrastructure, defensive investing
Guest: Jeremy Roll, President of Roll Investment Group - https://www.linkedin.com/in/jeremy-roll-655107/
Newsletter: https://www.mechanicsofmoney.co
Website: https://silvermancapital.com
This conversation is for educational purposes only and does not constitute investment advice.
Subscribe to Mechanics of Money for weekly conversations about private markets, alternative investments, and the mechanics behind building real wealth.
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