Mechanics of Money

Sam Silverman | Silverman Capital
  • 5.0 (35)
  • Investing
  • 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. 19h ago

    He Sold His Companies. Then Had to Learn How to Invest. | Shane Neman

    A business can pay you for years. Once you sell it, the proceeds have to do a different job. How do you turn a lump sum into a portfolio you can actually live with? Shane Neman is the founder of JoonBug and EZ Texting and a family office investor at Neman Ventures. He tells Sam Silverman how he went from running companies to learning how to invest, starting with commercial real estate and gradually adding managers, public equities, private equity and venture. Shane explains how he separates his search for income from the early-stage investments he makes for growth. He also shares what he had to unlearn as an operator, including the impulse to make a move every time something goes against him. In this conversation: Why an early cloud software startup ran into an infrastructure problemHow nightclub ticketing and marketing led to a business texting platformHow bootstrapping changes the economics of a sale for the founderWhy Shane looked for wealth managers who would teach himWhy commercial property was his first stop for incomeHow direct ownership changed the way he evaluates managersWhy frontier technology and familiar consumer needs can sit in the same venture portfolioWhat working a sales call and a delivery revealed about a startupWhere income comes from outside his venture investmentsHow family offices share operating responsibilities, fees and carryWhy reacting to every portfolio loss can compound the damage Topics covered: investing after a business exit, founder dilution, portfolio income, commercial real estate, venture capital, startup diligence, family office co-investment Guest: Shane Neman, founder of JoonBug and EZ Texting and family office investor at Neman Ventures · Official Website: https://www.shaneneman.com/ Mechanics of Money: https://www.mechanicsofmoney.co Silverman Capital: https://silvermancapital.com Follow Mechanics of Money in your podcast app for weekly conversations on private markets, alternative investments and building wealth. #mechanicsofmoney #businessexit #familyoffice #venturecapital #privateequity #realestateinvesting

  2. Oct 27

    The 9 Money Habits Keeping You Poor

    Making a lot of money and becoming wealthy are two different skill sets. If every increase in income brings another increase in spending, you can earn a great living and still depend on your next paycheck. In this short solo episode, I break down nine money habits that keep high earners from building wealth, including lifestyle inflation, confusing monthly payments with affordability, and measuring net worth without considering liquidity and cash flow. I also share how I approached earning more, turning the gap between income and spending into assets, and deciding what I wanted that money to make possible. For me, the goal was autonomy. More control over my time, my work, and the life I wanted to live. Because eventually, you have to decide what all that money is actually for.

  3. Oct 20

    He Sold His Company for Equity. Then Bought It Back. | Colin Hodge

    A company sale can leave you with shares instead of spendable proceeds. What changes when the founder later buys the business back and starts building around income, control, and a different quality of life? Colin Hodge is the co-founder and co-owner of DOWN, the dating app originally known as Bang with Friends, and the author of Outrageous Startup Growth. His career includes serving as chief growth officer at 17Live and launching its U.S. platform as its first U.S. CEO. In this conversation with Sam Silverman, Colin explains how an investment proposal became a multimillion-dollar equity acquisition, why liquidity was more difficult than he expected, and how he later reacquired DOWN from an intermediate buyer at a low-six-figure price. He now runs the business with a friend and without outside investors. The discussion follows the practical consequences: testing willingness to pay, retaining ownership, delegating operations, and knowing what a future transaction needs to deliver for the founder. In this conversation: How the original investment offer became an equity acquisitionWhy receiving shares did not make liquidity straightforwardHow DOWN passed to another buyer before Colin bought it backWhy dating apps can lose both happy and unhappy customersHow early monetization tests whether customers value the productHow Colin describes his accountant-advised changes in company structureWhy ownership, dilution, and investor preferences change founder outcomesHow delegation and remote work support the lifestyle Colin wantsWhy personal priorities belong in acquisition and partnership decisionsHow resilience draws on difficulties the founder has already survivedHow a decision rubric can clarify both parties' priorities and red linesWhy Colin walked away from a potential acquisition involving a smaller appHow a company that operates without its owners may appeal to future buyersWhy Colin prefers spending on shared experiences and connectionsTopics covered: selling a business for stock, founder liquidity, equity acquisitions, business buybacks, founder ownership, startup monetization, customer retention, founder psychology, negotiation, exit readiness Guest: Colin Hodge - co-founder and co-owner of DOWN; author of Outrageous Startup Growth Website: https://colinhodge.com/ Book: https://colinhodge.com/book/ LinkedIn: https://www.linkedin.com/in/ckbhodge/ Newsletter: https://www.mechanicsofmoney.co Website: https://silvermancapital.com Follow Mechanics of Money in your podcast app for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #entrepreneurship #businessexit #founderownership #startupmonetization #founderpsychology #mechanicsofmoney

  4. Oct 13

    How Does Your Real Estate Sponsor Survive a Bad Deal? | Aleksey Chernobelskiy

    A lower fee can improve the terms of an investment. But does the person managing the deal still have a viable business, and an incentive to keep working, if the expected profit disappears? Sam Silverman speaks with Aleksey Chernobelskiy, co-founder and CEO of GP-LP Match and author of LP Investing Lessons. Before his work with private investors, Aleksey led underwriting and portfolio management at STORE Capital. They examine how limited partners evaluate the sponsor behind a deal, not just the return in a presentation. Aleksey describes the shift toward more investor-favorable terms in the opportunities he sees. Sam adds a hypothetical sponsor-business example showing why acquisition-fee revenue can be uneven and why the timing of compensation matters. Their discussion connects those economics to co-investment, communication, cash-flow preferences, and the preparation required before committing illiquid capital. In this conversation: Why deal flow still needs to fit an investor’s criteriaHow GP–LP terms have shifted in Aleksey’s experienceHow co-investment expectations affect sponsorsWhat a first-year cash-flow filter can excludeWhy existing investor relationships deserve attentionWhat a pitch deck should explain about the operatorHow experience and integrity enter manager selectionWhy sponsor-company revenue is different from personal incomeHow low fees and a lost promote can affect incentivesWhy different asset classes create different income patternsWhat diligence practice requires before investingWhy illiquidity raises the stakes of the initial decision Topics covered: real estate syndications, limited partner due diligence, sponsor economics, acquisition fees, preferred returns, profit splits, co-investment, investor relations, cash-on-cash returns, private-market investing Guest: Aleksey Chernobelskiy, co-founder and CEO of GP-LP Match https://gplpmatch.com/ LP Investing Lessons: https://www.lplessons.co/ LinkedIn: https://www.linkedin.com/in/chernobelskiy 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 them. #realestateinvesting #limitedpartners #duediligence #syndications #privateinvestments #investorrelations #mechanicsofmoney

  5. Oct 6

    You Bought a Business. Why Aren't You Getting Paid? | Blake Harber

    Buying a company gives you ownership. It may also give you a repair job, an unfamiliar sales cycle, and a long wait before you can take cash home. Blake Harber, founder and managing partner of StudioGTM, previously held sales leadership roles at HireVue, Lucid, and Workstream. After leaving corporate sales leadership, he moved into consulting and small business ownership, including vending and hardware distribution. In this conversation with Sam Silverman, Blake works through the gap between an attractive acquisition on paper and a business you can actually operate. He shares what reinvestment did to his vending cash flow, what he underestimated about a seller transition, and why his experience building sales teams did not transfer neatly to an unfamiliar industry. The conversation also explores the less obvious alternatives to buying outright, the personal runway required to learn, and how AI is changing the support work behind a human sales team. In this conversation: Why startup growth and personal equity outcomes can divergeWhy vending income was far from passive after the purchaseHow repairs, staffing, and reinvestment delay owner distributionsWhy Blake reconsidered the personal risk of acquisition financingHow a short seller handoff exposed knowledge and relationship gapsWhy customer contact turnover mattered after closingHow seller involvement and deal incentives affect a transitionWhy building within your expertise may fit better than buyingHow a general manager role can help you test business ownershipWhy an outbound sales hire still needs a system and a managerHow AI support can leave more room for human buyer contactWhy selling a business creates a cash-flow replacement decisionHow Blake thinks about time, trusted operators, and personal runway Topics covered: small business acquisition, vending operations, seller transitions, owner dependence, cash flow and reinvestment, acquisition financing, buy versus build, general manager roles, founder-led sales, AI-assisted outbound, personal runway Guest: Blake Harber, founder and managing partner of StudioGTM LinkedIn: https://www.linkedin.com/in/blakejharber Blake's newsletter: https://blakeharber.substack.com/ Mechanics of Money newsletter: https://www.mechanicsofmoney.co Silverman Capital: https://silvermancapital.com Subscribe to the Mechanics of Money for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth. #businessacquisition #smallbusiness #entrepreneurship #cashflow #businessownership #founderledsales #mechanicsofmoney

  6. Sep 29

    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

  7. 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

  8. 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

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5
out of 5
35 Ratings

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
    129
  • Rating
    Explicit
  • Copyright
    © 2026 Mechanics of Money
  • Show Website
    Mechanics of Money

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