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. 22h ago

    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

  2. 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

  3. Aug 4

    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

  4. Jul 29

    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

  5. Jul 21

    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

  6. Jul 14

    Turning $2M Into a $20M Tax Loss: Inside the Strategies of the Ultra Wealthy | Noah Rosenfarb, CPA

    What's the difference between the entrepreneur who pays full capital gains tax on a $20M exit and the one who pays almost none? Usually, it's not income. It's whether anyone on their team was hired to plan ahead. Sam sits down with Noah Rosenfarb, a third-generation CPA who's spent his career inside the financial lives of the ultra wealthy. Noah started as an expert witness in high-net-worth divorce cases, built and sold a family office for affluent divorced women, syndicated close to $1B in real estate, and watched much of that portfolio get crushed when rates doubled.  Today he leads Wealthrive, a tax strategy firm for entrepreneurs with seven-figure incomes and eight-figure exits, built on a simple thesis: your tax preparer files history, but a strategist plans the future. In this conversation: From forensic accountant to expert witness in divorce court, and why acrimony paid the billsThe $100M family that skipped the prenup on purpose, and what the wife discovered in the divorceWhy the ultra wealthy own nothing but control everythingWhat exit tax planning is worth: typically 10-30% of the purchase priceThe proprietary structure that turns $2M invested into a $20M paper lossWhat tax "risk" actually means: audit odds by income bracket, case law, and opinion lettersPhantom gains, partnership allocations, and depreciation arbitrageNoah's real estate arc: a decade of 27% IRRs, then deals returning 40 cents, 20 cents, or zeroLosing tens of millions of investor capital, and rebuilding with gratitudeWhy his new capital only goes into his operating business and public marketsHis advice for founders years before an exit: hire a tax strategist, not just a preparer Topics covered: tax strategy, tax planning, capital gains tax, exit planning, selling a business, family office, trusts, asset protection, prenuptial agreements, IRS audits, real estate syndication, depreciation, cost segregation, phantom gains, partnership structures, high net worth, private markets, entrepreneurship, wealth building Guest: Noah Rosenfarb, CPA, Founder, Wealthrive | https://www.linkedin.com/in/noahrosenfarb 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. #taxstrategy #taxplanning #exitplanning #wealthbuilding #familyoffice #privatemarkets #mechanicsofmoney #entrepreneurship #capitalgains #realestateinvesting

  7. Jul 7

    Running a US Real Estate Fund From a Costa Rica Surf Town | Sarah Miskelly

    How do you run a US real estate fund, SEC-regulated, entirely US-based investors, from a surf town in Costa Rica, and still turn down most of the deals you're offered? Sam sits down with Sarah Miskelly, founder and fund manager of Hylee Capital, a firm that helps accredited investors access carefully selected US real estate and alternative investments. Sarah grew up in her family's real estate business in Toronto, built a multi-six-figure brokerage, and then walked away from it at its peak, burned out and planning an exit from the start. She'd been quietly investing as an LP on the side, so she shut the brokerage down, moved her family to Costa Rica, and rebuilt as a fund manager she can run from her laptop. To date, Hylee Capital has deployed over $16M alongside roughly 100 investors. In this conversation: The full origin story, from managing family multifamily properties to running a fundWhy she walked away from a multi-six-figure brokerage business at its peakWhat relocating a family abroad actually costs, and why "it's cheaper" is a mythWhether managing capital remotely helps or hurts credibility with investorsDiversifying across verticals and the capital stack, not just asset classesMatching deals to an investor's actual buy box and stage of lifeWhy fund-manager compensation weighted toward exit keeps interests alignedWhat real due diligence looks like: underwriting, whisper networks, background checksThe large-name sponsor deal she passed on, and what the capital stack gave awayWhy she turns down almost everything sent to her inboundHer one piece of advice for relocating and for breaking into the space: bet on yourselfTopics covered: real estate, fund management, private real estate, due diligence, capital stack, preferred equity, common equity, LP investing, portfolio diversification, alternative investments, accredited investors, real estate syndication, passive income, relocating abroad, Costa Rica, expat life, lifestyle design, women in finance, private markets Guest: Sarah Miskelly, Founder & Fund Manager, Hylee Capital | https://hyleecapital.com 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. #realestateinvesting #fundmanagement #privatemarkets #alternativeinvestments #duediligence #accreditedinvestor #mechanicsofmoney #lifebydesign #passiveincome #wealthbuilding

  8. Jun 30

    Lifestyle by Design After Building a Multiple 8-Figure Business | Arman Taheri

    How did a COVID-era face mask business become the launchpad for an 8-figure service company, and a life built entirely by design? Sam sits down with Arman Taheri, co-founder and CEO of TalentPop, a talent solutions company serving over 750 e-commerce brands with customer service management, executive assistants, and marketing support. Arman started in e-commerce, pivoted to face masks during COVID, scaled to eight figures in under a year, and used that momentum to build TalentPop into a multi-eight-figure platform, all while deliberately designing his life around the business rather than the other way around. In this conversation: The full origin story, from medical scrubs to face masks to discovering the CX staffing gapWhy mastering one core solution before diversifying was the catalyst for scaleThe "water faucets" framework for predictable, repeatable growthHow picking the wrong market size can quietly kill your ambitionsIncome tiers from $10K/month survival to generational wealth, and what changes at each levelMapping out what your dream lifestyle actually costs, then reverse engineering toward itWhy Arman chose a strategic partner over private equity, and what an 18-month search process looks likePersonal capital allocation: real estate, alternatives, managed wealth, and letting money compoundWhy investing in your primary residence might be the single best lifestyle investmentThe case against grind culture, and how to build ambitiously without burning outTopics covered: e-commerce, customer service, service business, scaling, COVID pivot, entrepreneurship, life by design, income tiers, generational wealth, strategic partnerships, private equity, personal finance, capital allocation, alternative investments, real estate, Dubai, lifestyle design, anti-grind culture Guest: Arman Taheri, Co-Founder & CEO, TalentPop | https://www.talentpop.co 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. #entrepreneurship #ecommerce #servicesbusiness #wealthbuilding #lifebydesign #privatemarkets #mechanicsofmoney #capitalallocation #alternativeinvestments #generationalwealth

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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
    118
  • Rating
    Explicit
  • Copyright
    © 2026 Mechanics of Money
  • Show Website
    Mechanics of Money

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