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 119 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Sam Silverman | Silverman Capital hosts Mechanics of Money, a business show with 119 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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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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  Episode #26

  Why Ownership Beats a Bigger Sales Paycheck | Sam Jacobs

  Aug 25, 202645 minS1

  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 grows How operators can create enterprise value without sharing proportionately in the upside Why fast-growing AI companies and slower-growth software businesses face radically different valuation markets Why there is no separate set of unit economics for AI How stock-option exercise costs and taxes complicate employee equity Why lifestyle inflation can turn exceptional income into a higher break-even point How a large annual commission can mimic some of the discipline of a liquidity event Why ownership becomes more attractive as the time horizon expands How to diligence a sales team before accepting an offer Why a difficult product can sometimes teach more than an easy quota How compensation plans change after a seller breaks them Why AI may increase productivity without removing the human sale How Pavilion is being built as an enduring, cash-generating institution Topics 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

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  Episode #25

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

  Aug 18, 202644 minS1

  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. #passiveinvesting #realestateinvesting #syndications #alternatives #privatemarkets #marketcycles #limitedpartners #mechanicsofmoney

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  Episode #24

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

  Aug 11, 202649 minS1

  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 employee Why delaying Microsoft’s offer by one year carried a $20 million opportunity cost Why a $500 million paper net worth was not the same as accessible cash How IPO lockups and concentrated stock complicate personal liquidity Why Martin placed most of a major win into conservative, cash-flowing assets How AI is changing entry-level careers and traditional training grounds Why Martin focuses on capital-efficient, pre-seed B2B software What he looks for in founding teams and their distribution advantages Why his angel portfolio underperformed his professionally managed venture portfolio How deal flow, selection bias, and adequate runway affect investment outcomes Why venture funds depend on extreme outliers rather than consistent moderate wins How aspiring venture managers can build credibility before raising a blind pool Topics 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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  Episode #23

  The Psychology Of Money, Marriage, And Raising Wealthy Kids | Megan McCoy, Ph.D.

  Aug 4, 202636 minS1

  How much of your financial life have you never said out loud to another person, and what is that silence actually costing you? Sam sits down with Dr. Megan McCoy, the first Certified Financial Therapist and Acting Chair of the Personal Financial Planning program at Kansas State University. Megan knew she wanted to be a therapist as a kid. She was midway through a doctorate in family therapy when the Great Recession hit, and her faculty started cross-training marriage and family therapists alongside financial planning students. Sitting next to a financial planner while treating clients changed her practice permanently, and she never stopped taking the finance coursework. She now runs the financial planning program at K-State, co-edits the Financial Planning Review, and researches the intersection most financial plans ignore entirely: money and well-being. In this conversation: What a financial therapist actually is, and how the discipline came out of the Great Recession Why the emotional case for a paid-off mortgage can beat the math on paper The shame that followed 2008, and why self-forgiveness is a financial step How retirement takes your identity along with your title, and who it hits hardest Why your ten-year dream stays vague, and the questions that force it into focus The quarterly lottery ticket date she runs with her husband The $20 experiment proving giving beats spending, even when people are forced into it Why 70% of people have not talked to a living soul about money in a year Financial infidelity, and why it damages a marriage close to the level of actual infidelity The prenup reframe that takes money off the table instead of putting it on Why charitable giving is one of the biggest fights couples have about money How spenders and savers slowly push each other to opposite extremes The money story parents pass to their kids without ever saying it out loud Making a 12-year-old earn a $400 bat, and where enabling actually comes from Whether college still makes sense, and the two-plus-two path she recommends Topics covered: financial therapy, money psychology, behavioral finance, money and marriage, financial infidelity, joint accounts, prenuptial agreements, divorce planning, spending and happiness, charitable giving, financial socialization, raising kids with wealth, enabling adult children, retirement identity, college ROI, one income households, wealth psychology Guest: Megan McCoy, Ph.D., Acting Chair of Personal Financial Planning, Kansas State University | https://www.linkedin.com/in/megan-mccoy-phd Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Subscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #financialtherapy #moneyandmarriage #wealthpsychology #behavioralfinance #financialinfidelity #moneymindset #raisingwealthykids #privatemarkets #personalfinance #mechanicsofmoney

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