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 blue

Mechanics of Money is a business podcast hosted by Sam Silverman | Silverman Capital, with 122 episodes on record and a Required Pod Score of 80.

Sam Silverman | Silverman Capital hosts Mechanics of Money, a business show with 122 episodes published.

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  Episode #31

  The Tax Break Every Founder Should Know Before Selling | Brian Lamb

  Sep 29, 202629 minS1

  Years at a startup do not necessarily mean years holding qualifying stock. For founders and employees with equity, that distinction can matter long before a business is sold. Brian Lamb is the founder and CEO of Promissory and a co-founder of Trust & Will. His experience planning around his own equity led him to focus on QSBS and the trust structures founders consider before a liquidity event. In this conversation with Sam Silverman, Brian explains how company eligibility, stock acquisition, and the eventual deal interact. They discuss the difference between vested options and purchased shares, the changes to QSBS rules for newer stock, LLC conversions, and why the number in an acquisition announcement may tell a founder very little about the personal outcome. They also examine the control tradeoff in Brian's approach to non-grantor trusts and the cash demands employees can face when leaving a company. In this conversation: Why Brian's own equity planning led to Promissory How everyday estate planning differs from pre-exit trust planning What QSBS means and why company eligibility is only part of the question Why option vesting and stock acquisition are different events How acquisition dates affect holding-period and exclusion rules Why federal and state tax treatment can differ How company growth can affect newly issued stock What founders weigh when converting an LLC to a C corporation Why acquisition consideration and deal structure matter personally Why Brian encourages individual counsel for founders When Brian prefers to begin trust planning How gifting shares changes ownership and control Why vested options can still require cash at departure What employees can ask about early exercise Topics covered: QSBS, qualified small business stock, Section 1202, stock options, holding periods, founder exits, non-grantor trusts, trust stacking, LLC conversions, 83(b) elections, equity compensation Guest: Brian Lamb - Founder and CEO, Promissory ; Co-founder, Trust & Will https://www.promissory.com/ https://www.linkedin.com/in/brianlambco Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe to the Mechanics of Money for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. Eligibility and tax consequences depend on individual facts, acquisition dates, and the transaction. Federal and state treatment can differ. #qsbs #founderexits #stockoptions #estateplanning #equitycompensation #mechanicsofmoney

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  Episode #30

  Why He's Cutting Back on Angel Investing After 200+ Deals | Adam Spector

  Sep 22, 202644 minS1

  A startup investment can look successful long before it produces spendable cash. Adam Spector has backed more than 200 early-stage companies, and he is reducing how much of his own portfolio he wants in that world. Adam is a four-time founder and the Founder & CEO of Chore, which supports startups with back-office operations. He also hosts Entrepreneurial Excellence. His perspective combines building companies, investing alongside founders, and waiting to learn what those investments are actually worth. Sam and Adam examine a secondary sale that Adam says repaid an entire fund, the long silence that followed, and the limits of treating a strong founder network as an investing advantage. They discuss his move toward later-stage opportunities and public equities, while separating his personal choices from a universal allocation formula. The second half turns to a different balance sheet: the time, stress, and family tradeoffs that can disappear inside the pursuit of a bigger net worth. In this conversation: Why Adam regrets shutting down his first company How an acquisition can benefit founders and investors differently How his first syndicate pooled smaller checks Why distributions matter alongside paper valuations How a secondary sale repaid one fund in Adam's account Why investor communication changes the ownership experience Why he is reducing his personal early-stage allocation How he approaches later-stage SPVs and trusted introductions Why business expertise does not automatically transfer to investing How frugality can become difficult to turn off Where spending buys useful time and reduces household friction How Sam and Adam weigh ambition against personal financial stress Topics covered: angel investing, startup secondaries, liquidity, venture capital, SPVs, public equities, founder finances, opportunity cost, time, sustainable entrepreneurship Guest: Adam Spector, Founder & CEO of Chore Chore: https://www.hirechore.com/ Adam on LinkedIn: https://www.linkedin.com/in/adamspector2/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe to Mechanics of Money for weekly conversations on private markets, alternative investments, and the decisions behind building and using wealth. #angelinvesting #venturecapital #startupinvesting #founderfinances #capitalallocation #entrepreneurship #mechanicsofmoney

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  Episode #29

  Deferred Sales Trusts After a Business Sale: Who Controls the Money? | Brett Swarts

  Sep 15, 202628 minS1

  A founder can sell a business and still have important limits on how the proceeds are accessed and invested. What changes when the exit produces a promissory note instead of unrestricted cash? Brett Swarts is the Founder & CEO of Capital Gains Tax Solutions and the author of Building a Capital Gains Tax Exit Plan. His background in commercial real estate informs his work with entrepreneurs and their advisors on exit planning. In this conversation with Sam Silverman, Brett explains his Deferred Sales Trust model through a hypothetical $10 million business sale. Sam follows the money: who holds it, who approves investments, what happens if returns fall short, and how payments reach the seller. They also discuss a separate estate-planning structure, the distinction between basis and estate tax, and the investing blind spots that can follow a successful exit. In this conversation: Why an exit may require additional expertise alongside an existing CPA How the founder’s next business or lifestyle affects the exit plan How Brett describes the seller-to-trust-to-buyer sequence Why the seller becomes a lender under the note structure How investment approvals divide control What happens in Brett’s example when assets underperform the note rate How principal and interest affect the payment discussion Why lifetime cash needs and inheritance goals can pull in different directions Why a basis adjustment and estate tax address different issues How Brett frames creditor protection and diversification Why entrepreneurial success does not establish investing skill How one pair of founders kept capital available for future opportunities Topics covered: Deferred Sales Trust, business exit planning, installment sales, promissory notes, trust control, founder liquidity, estate planning, capital allocation Guest: Brett Swarts, Founder & CEO, Capital Gains Tax Solutions https://capitalgainstaxsolutions.com/ LinkedIn: https://www.linkedin.com/in/brett-swarts Book and background: https://capitalgainstaxsolutions.com/our-ceo/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe to Mechanics of Money for weekly conversations on private markets, alternative investments, and the decisions behind building and managing capital. #brettswarts #deferredsalestrust #businessexit #exitplanning #capitalgainstax #estateplanning #mechanicsofmoney

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  Episode #28

  Franchise Investing: Own the Locations or Own the System? | Andy Louis-Charles

  Sep 8, 20261h 7mS1

  A franchise location and a franchise brand can participate in the same customer sale while carrying very different costs, responsibilities, and incentives. That distinction is where this conversation starts to get useful. Andy Louis-Charles is Managing Partner at Ranchos Ventures, which focuses on the franchise asset class. A former Chief Strategy Officer at Custom Ink and investment analyst at The Motley Fool, Andy has also owned multiple tax-franchise units. He brings both the capital-allocation perspective and the experience of executing inside an operating business. Sam Silverman and Andy work through the mechanics of company-owned expansion, franchisor revenue, and multi-unit franchise ownership. They explore why owners can resist growth once a business supports their lifestyle, why scale can change the buyer pool at exit, and why Andy is interested in services sold to restaurants rather than restaurant ownership itself. The conversation also examines his ownership thesis for white-collar professionals facing AI disruption, with a practical close on challenging assumptions before buying a business. In this conversation: How operating experience can inform capital allocation Why investing after an exit can feel unfamiliar How Andy combines broad venture exposure with active private ownership What separates a franchisor investment from franchisee ownership Why taking cash out can compete with funding expansion How royalties and service fees change a brand’s economics What a hypothetical 100-unit expansion requires in capital and people How operating scale can change a franchise portfolio’s buyer pool Why property ownership and business ownership need separate analysis How owner incentives and franchisee profitability interact Why Andy sees an ownership opportunity in white-collar disruption What attracts him to recurring B2B services and care businesses How franchise comparisons and operator calls can test acquisition assumptions Topics covered: franchise investing, franchisor versus franchisee, multi-unit ownership, capital allocation, business expansion, unit economics, recurring B2B services, business acquisition, franchise due diligence Guest: Andy Louis-Charles, Managing Partner at Ranchos Ventures LinkedIn: https://www.linkedin.com/in/andylc Ranchos Ventures: https://ranchos.com/ Ranch Advisors: https://ranchadvisors.com/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe to the Mechanics of Money for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #franchising #franchiseinvesting #businessownership #capitalallocation #smallbusiness #privateinvesting #mechanicsofmoney

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  Episode #27

  Why $100M Can Still Feel Empty: The Psychology of Enough | Brian Portnoy

  Sep 1, 202640 minS1

  What is money still supposed to do after it has already bought financial security? A larger balance sheet can expand your options, but it cannot decide which options make a life meaningful. Brian Portnoy, PhD, CFA, is the founder and CEO of Shaping Wealth, a global expert on the psychology of money, and the author of *The Geometry of Wealth*. After more than two decades across mutual funds, hedge funds, portfolio management, research, and investor education, Brian came to a blunt conclusion: investing is not only a math problem. It is a psychology problem. Sam and Brian examine "funded contentment", the ability to underwrite a meaningful life, and the four sources Brian uses to make that idea practical: connection, control, competence, and context. They discuss the moving definition of enough, what retirement can feel like when work supplied identity, and why experiences and relationships tend to outlast the pleasure of expensive objects. In this conversation: Why Brian left complex investment analysis for behavioral finance The difference between being rich and being wealthy How funded contentment turns meaning into a financial question The four C's: connection, control, competence, and context Why many of life's most valuable experiences carry a modest price tag Retiring from a career versus retiring toward a next chapter How a $100 million portfolio can coexist with an empty life Why the payoff from a luxury purchase often moves beyond the object The missing complexity premium in alternative investments Why doing nothing may be the hardest part of compounding Illiquidity as both behavioral guardrail and portfolio risk What volatility laundering hides in private-market reporting Why investing outside a plan is speculation The advisor's role as planner and behavioral coach How social comparison turns everyone into your financial neighbor Topics covered: psychology of money, behavioral finance, funded contentment, rich versus wealthy, financial planning, retirement purpose, alternative investments, complexity premium, private-market illiquidity, volatility laundering, investor behavior, wealth management Guest: Brian Portnoy, PhD, CFA, founder and CEO of Shaping Wealth - https://www.shapingwealth.com/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe to Mechanics of Money for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #behavioralfinance #psychologyofmoney #fundedcontentment #financialplanning #alternativeinvestments #privatemarkets #wealthmanagement #investorbehavior #mechanicsofmoney

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