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 117 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 117 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 #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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  Episode #22

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

  Jul 29, 202629 minS1

  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 time Why flexible bank points beat co-branded airline and hotel cards for most travelers The $6,000 flight to Italy Sam booked for 70,000 points, and what that works out to per dollar spent How to match a card strategy to where your business actually spends, even when your categories earn no bonus Why airline status is close to worthless if you were already going to fly up front Which hotel statuses you can buy and which you can't: Marriott Ambassador vs. Hilton vs. Hyatt The $30,000 Christmas week in St. Kitts a client got for points and nothing out of pocket Marriott's fifth-night-free rule and why points only redeem well at the top end The $10-a-month tool that hunts premium cabin deals for you in plain English Repositioning flights: paying $200 to reach a hub and unlocking thousands in award value The planning reframe that turns "there's never availability" into a $1,700-a-night room for 30,000 points Topics 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

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  Episode #21

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

  Jul 21, 202636 minS1

  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 crisis Why 60% of the people you spend the most time with vanish after an exit The Transaction Illusion and why money only solves two levels of Maslow's hierarchy The mountain metaphor: ascent, summit, and the descent nobody talks about Why $15M in cash can feel smaller than $3M a year in income What happens when operators become capital allocators overnight Jerome's Five Scars of Success and the $44M client who wouldn't take a vacation Why Die with Zero changed how his clients think about spending The scholarship text on Mother's Day and what fulfilled founders actually spend on The 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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