Mechanics of Money

Sam Silverman | Silverman Capital
  • 5.0 (1)
  • 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. 4 days ago

    Franchise Investing: Own the Locations or Own the System? | 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

  2. 1 Sept

    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

  3. 25 Aug

    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

  4. 18 Aug

    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

  5. 11 Aug

    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

  6. 4 Aug

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

    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 RecessionWhy the emotional case for a paid-off mortgage can beat the math on paperThe shame that followed 2008, and why self-forgiveness is a financial stepHow retirement takes your identity along with your title, and who it hits hardestWhy your ten-year dream stays vague, and the questions that force it into focusThe quarterly lottery ticket date she runs with her husbandThe $20 experiment proving giving beats spending, even when people are forced into itWhy 70% of people have not talked to a living soul about money in a yearFinancial infidelity, and why it damages a marriage close to the level of actual infidelityThe prenup reframe that takes money off the table instead of putting it onWhy charitable giving is one of the biggest fights couples have about moneyHow spenders and savers slowly push each other to opposite extremesThe money story parents pass to their kids without ever saying it out loudMaking a 12-year-old earn a $400 bat, and where enabling actually comes fromWhether college still makes sense, and the two-plus-two path she recommendsTopics 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

  7. 29 Jul

    How to Turn Business Spending Into Free Business Class Flights | Colin Stroud

    You're sitting on a pile of credit card points and no real idea what they're worth. What if the same balance that gets you a $600 hotel room could get you an $1,800-a-night suite instead? And what if the reason you can never find award availability has nothing to do with your points at all? Sam sits down with Colin Stroud, founder of Go Somewhere, a credit card rewards consultancy for high-spending business owners and people sitting on large point balances. Colin got into points out of necessity: he'd taken a low-paying job, had a wife and a baby, and realized the only vacation his family could afford was a $400 Airbnb in the woods in rural Ohio. He went down the rabbit hole from a boring corporate desk, started booking trips for friends, and turned it into a full-time business in 2023. He's since helped 500+ families take trips they assumed were out of reach, from transatlantic business class for a family of nine to $30k+ luxury Caribbean stays during peak dates. In this conversation: How Colin went from no travel budget to consulting on points full timeWhy flexible bank points beat co-branded airline and hotel cards for most travelersThe $6,000 flight to Italy Sam booked for 70,000 points, and what that works out to per dollar spentHow to match a card strategy to where your business actually spends, even when your categories earn no bonusWhy airline status is close to worthless if you were already going to fly up frontWhich hotel statuses you can buy and which you can't: Marriott Ambassador vs. Hilton vs. HyattThe $30,000 Christmas week in St. Kitts a client got for points and nothing out of pocketMarriott's fifth-night-free rule and why points only redeem well at the top endThe $10-a-month tool that hunts premium cabin deals for you in plain EnglishRepositioning flights: paying $200 to reach a hub and unlocking thousands in award valueThe planning reframe that turns "there's never availability" into a $1,700-a-night room for 30,000 pointsTopics covered: credit card points, travel rewards, points and miles, business class, award travel, flexible points, transfer partners, airline status, hotel status, Marriott, Hyatt, Amex, Chase, Capital One, seats.aero, luxury travel, business owners, high spenders, travel hacking Guest: Colin Stroud, Founder, Go Somewhere | https://www.gosomewhere.world 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. #creditcardpoints #pointsandmiles #travelrewards #awardtravel #businessclass #luxurytravel #travelhacking #mechanicsofmoney #businessowners #smartmoney

  8. 21 Jul

    Why Founders Get Depressed After Selling Their Company | Jerome Myers, CEPA

    What happens when you sell your company, deposit more money than you've ever had, and immediately feel worse than before? Sam sits down with Jerome Myers, Certified Exit Planning Advisor, founder of Exit to Excellence, and author of Your N.E.X.T.: Finding Fulfillment After Your Exit. Jerome built a $20 million division from zero in a single year inside a Fortune 550 company, walked away on principle, then later discovered what he calls the Founder's Exit Paradox: founders who win on paper and quietly fall apart afterward.  He now coaches founders through what comes after the transaction: the identity loss, the relationship collapse, and the spending paralysis that no advisor prepares them for. In this conversation: Jerome's origin story and the $2B founder who said he still hasn't beaten his crisisWhy 60% of the people you spend the most time with vanish after an exitThe Transaction Illusion and why money only solves two levels of Maslow's hierarchyThe mountain metaphor: ascent, summit, and the descent nobody talks aboutWhy $15M in cash can feel smaller than $3M a year in incomeWhat happens when operators become capital allocators overnightJerome's Five Scars of Success and the $44M client who wouldn't take a vacationWhy Die with Zero changed how his clients think about spendingThe scholarship text on Mother's Day and what fulfilled founders actually spend onThe purpose formula founders already know but forget to apply to themselves Topics covered: exit planning, founder psychology, post-exit depression, identity crisis, transaction illusion, hedonic treadmill, capital allocation, Maslow's hierarchy, private equity, founder fulfillment, giving policy, buy box, accredited investors, wealth management, entrepreneurship Guest: Jerome Myers, CEPA, MBA, Founder, Exit to Excellence | https://www.linkedin.com/in/jeromemyers 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. #exitplanning #founderpsychology #postexitlife #transactionillusion #mechanicsofmoney #wealthmanagement #privatemarkets #entrepreneurship #founderexit #capitalallocation

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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
    121
  • Rating
    Explicit
  • Copyright
    © 2026 Mechanics of Money
  • Show Website
    Mechanics of Money

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