Mechanics of Money

Sam Silverman | Silverman Capital
  • 5.0 (35)
  • Investing
  • Updated Weekly

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. Subscribe to the weekly newsletter: https://www.mechanicsofmoney.coInvest with Silverman Capital: https://silvermancapital.co

  1. 5d ago

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

    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 PromissoryHow everyday estate planning differs from pre-exit trust planningWhat QSBS means and why company eligibility is only part of the questionWhy option vesting and stock acquisition are different eventsHow acquisition dates affect holding-period and exclusion rulesWhy federal and state tax treatment can differHow company growth can affect newly issued stockWhat founders weigh when converting an LLC to a C corporationWhy acquisition consideration and deal structure matter personallyWhy Brian encourages individual counsel for foundersWhen Brian prefers to begin trust planningHow gifting shares changes ownership and controlWhy vested options can still require cash at departureWhat employees can ask about early exerciseTopics 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

  2. Sep 22

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

    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 companyHow an acquisition can benefit founders and investors differentlyHow his first syndicate pooled smaller checksWhy distributions matter alongside paper valuationsHow a secondary sale repaid one fund in Adam's accountWhy investor communication changes the ownership experienceWhy he is reducing his personal early-stage allocationHow he approaches later-stage SPVs and trusted introductionsWhy business expertise does not automatically transfer to investingHow frugality can become difficult to turn offWhere spending buys useful time and reduces household frictionHow Sam and Adam weigh ambition against personal financial stressTopics 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

  3. Sep 15

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

    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 CPAHow the founder’s next business or lifestyle affects the exit planHow Brett describes the seller-to-trust-to-buyer sequenceWhy the seller becomes a lender under the note structureHow investment approvals divide controlWhat happens in Brett’s example when assets underperform the note rateHow principal and interest affect the payment discussionWhy lifetime cash needs and inheritance goals can pull in different directionsWhy a basis adjustment and estate tax address different issuesHow Brett frames creditor protection and diversificationWhy entrepreneurial success does not establish investing skillHow 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

  4. Sep 8

    Why Franchises Could Win the AI Economy | Andy Louis-Charles

    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 allocationWhy investing after an exit can feel unfamiliarHow Andy combines broad venture exposure with active private ownershipWhat separates a franchisor investment from franchisee ownershipWhy taking cash out can compete with funding expansionHow royalties and service fees change a brand’s economicsWhat a hypothetical 100-unit expansion requires in capital and peopleHow operating scale can change a franchise portfolio’s buyer poolWhy property ownership and business ownership need separate analysisHow owner incentives and franchisee profitability interactWhy Andy sees an ownership opportunity in white-collar disruptionWhat attracts him to recurring B2B services and care businessesHow 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

  5. Sep 1

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

    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 financeThe difference between being rich and being wealthyHow funded contentment turns meaning into a financial questionThe four C's: connection, control, competence, and contextWhy many of life's most valuable experiences carry a modest price tagRetiring from a career versus retiring toward a next chapterHow a $100 million portfolio can coexist with an empty lifeWhy the payoff from a luxury purchase often moves beyond the objectThe missing complexity premium in alternative investmentsWhy doing nothing may be the hardest part of compoundingIlliquidity as both behavioral guardrail and portfolio riskWhat volatility laundering hides in private-market reportingWhy investing outside a plan is speculationThe advisor's role as planner and behavioral coachHow social comparison turns everyone into your financial neighborTopics 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

  6. Aug 25

    Why Ownership Beats a Bigger Sales Paycheck | Sam Jacobs

    High income is not the same thing as wealth. For a revenue leader, the bigger question is whether the next five years should be spent maximizing cash compensation, or whether the next 20 should be spent building and owning an asset. Sam Jacobs is the founder and CEO of Pavilion, co-host of the Topline podcast, and author of Kind Folks Finish First. He has spent his career building and leading go-to-market organizations, from early-stage companies to global sales and customer-success teams. In this conversation, Sam Jacobs and Sam Silverman unpack the economics behind revenue leadership: the short tenure of a CRO, the value created between $1 million and $10 million in revenue, the practical limitations of employee stock options, and the lifestyle pressure that often follows a breakout year in sales. They also compare short-term cash optimization with long-term career development, outline a diligence process for evaluating sales roles, and consider what AI changes - and does not change - about complex human buying decisions. In this conversation: Why senior revenue roles become less secure as their impact growsHow operators can create enterprise value without sharing proportionately in the upsideWhy fast-growing AI companies and slower-growth software businesses face radically different valuation marketsWhy there is no separate set of unit economics for AIHow stock-option exercise costs and taxes complicate employee equityWhy lifestyle inflation can turn exceptional income into a higher break-even pointHow a large annual commission can mimic some of the discipline of a liquidity eventWhy ownership becomes more attractive as the time horizon expandsHow to diligence a sales team before accepting an offerWhy a difficult product can sometimes teach more than an easy quotaHow compensation plans change after a seller breaks themWhy AI may increase productivity without removing the human saleHow Pavilion is being built as an enduring, cash-generating institutionTopics covered: revenue leadership, sales compensation, CRO tenure, employee equity, stock options, lifestyle inflation, business ownership, entrepreneurship, B2B SaaS, unit economics, go-to-market strategy, AI and sales, career planning, wealth creation Guest: Sam Jacobs, founder and CEO of Pavilion  https://www.joinpavilion.com/ https://www.linkedin.com/in/samfjacobs/ 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. #salesleadership #revenueleadership #businessownership #entrepreneurship #equity #b2bsaas #futureofwork #mechanicsofmoney

  7. Aug 18

    Why a Full-Time LP Is Still Holding Cash | Jeremy Roll

    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 worldWhy he would not recommend his original 100% illiquid allocationHow technology and public solicitation changed private real estate investingWhy a business exit can create pressure to reinvest too quicklyHow Treasury liquidity changes the opportunity-cost calculationWhy private-market returns must compensate investors for illiquidityWhat Jeremy wants to see before redeploying capitalWhy a downturn can give LP capital more negotiating powerHow a sponsor's foreclosure can affect future borrowing costsWhat conservative underwriting and underpromising look like in practiceHow acquisition fees, AUM fees, and deal volume can weaken alignmentWhich real estate sectors Jeremy finds more predictableWhy new LPs should learn one asset class before diversifyingWhy Jeremy would rather enter a real estate recovery late than catch a falling knife earlyTopics 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. #passiveinvesting #realestateinvesting #syndications #alternatives #privatemarkets #marketcycles #limitedpartners #mechanicsofmoney

  8. Aug 11

    From $500M on Paper to 8 Unicorn Investments | Martin Tobias

    What happens when your net worth reaches $500 million, but exists almost entirely on paper? For Martin Tobias, watching that concentrated position fall roughly 90% became a lasting lesson about liquidity, risk, and the difference between appearing wealthy and possessing durable wealth. Martin is the founder and managing partner of Incisive Ventures, a pre-seed venture capital firm focused on B2B software companies that reduce friction at scale. A three-time venture-backed CEO, Martin raised more than $500 million across his companies and completed two IPOs. His career also includes Accenture, Microsoft, and a venture partner role at Ignition Partners. He has since invested in eight companies that reached unicorn status. In this conversation, Martin joins Sam Silverman to trace his progression from corporate employee to founder, angel investor, and professional venture manager. He explains how early Microsoft equity created life-changing wealth, why delaying that opportunity carried an enormous cost, and how his experience with concentrated IPO stock shaped the way he protects capital today. Martin and Sam also examine the power-law economics of venture capital. They discuss why most early-stage investments may fail, why a 10x outcome may still be insufficient within a diversified fund, and how a small number of 100x outliers can determine the performance of an entire portfolio. In this conversation: How Microsoft equity created founder-level wealth for a corporate employeeWhy delaying Microsoft’s offer by one year carried a $20 million opportunity costWhy a $500 million paper net worth was not the same as accessible cashHow IPO lockups and concentrated stock complicate personal liquidityWhy Martin placed most of a major win into conservative, cash-flowing assetsHow AI is changing entry-level careers and traditional training groundsWhy Martin focuses on capital-efficient, pre-seed B2B softwareWhat he looks for in founding teams and their distribution advantagesWhy his angel portfolio underperformed his professionally managed venture portfolioHow deal flow, selection bias, and adequate runway affect investment outcomesWhy venture funds depend on extreme outliers rather than consistent moderate winsHow aspiring venture managers can build credibility before raising a blind poolTopics covered: Martin Tobias, Incisive Ventures, venture capital, pre-seed investing, B2B software, startup equity, founder liquidity, concentrated stock positions, angel investing, power-law returns, portfolio construction, wealth preservation, AI and careers Guest: Martin Tobias, founder and managing partner of Incisive Ventures https://incisive.vc/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Follow the Mechanics of Money for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #venturecapital #preseed #startupinvesting #b2bsoftware #angelinvesting #wealthstrategy #privateinvestments #mechanicsofmoney

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5
out of 5
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About

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. Subscribe to the weekly newsletter: https://www.mechanicsofmoney.coInvest with Silverman Capital: https://silvermancapital.co

Information

  • Creator
    Sam Silverman | Silverman Capital
  • Years Active
    2024 - 2026
  • Episodes
    124
  • Rating
    Explicit
  • Copyright
    © 2026 Mechanics of Money
  • Show Website
    Mechanics of Money

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