Mechanics of Money

Hosted by Sam Silverman | Silverman Capital

Business Entrepreneurship

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Episodes

126

Latest episode

Oct 2026

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EN-US

About the show

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.co Invest with Silverman Capital: https://silvermancapital.co

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October 20, 2026Episode 3438 min

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 acquisition Why receiving shares did not make liquidity straightforward How DOWN passed to another buyer before Colin bought it back Why dating apps can lose both happy and unhappy customers How early monetization tests whether customers value the product How Colin describes his accountant-advised changes in company structure Why ownership, dilution, and investor preferences change founder outcomes How delegation and remote work support the lifestyle Colin wants Why personal priorities belong in acquisition and partnership decisions How resilience draws on difficulties the founder has already survived How a decision rubric can clarify both parties' priorities and red lines Why Colin walked away from a potential acquisition involving a smaller app How a company that operates without its owners may appeal to future buyers Why Colin prefers spending on shared experiences and connections Topics 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

October 13, 2026Episode 3329 min

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 criteria How GP–LP terms have shifted in Aleksey’s experience How co-investment expectations affect sponsors What a first-year cash-flow filter can exclude Why existing investor relationships deserve attention What a pitch deck should explain about the operator How experience and integrity enter manager selection Why sponsor-company revenue is different from personal income How low fees and a lost promote can affect incentives Why different asset classes create different income patterns What diligence practice requires before investing Why 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

October 6, 2026Episode 3246 min

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 diverge Why vending income was far from passive after the purchase How repairs, staffing, and reinvestment delay owner distributions Why Blake reconsidered the personal risk of acquisition financing How a short seller handoff exposed knowledge and relationship gaps Why customer contact turnover mattered after closing How seller involvement and deal incentives affect a transition Why building within your expertise may fit better than buying How a general manager role can help you test business ownership Why an outbound sales hire still needs a system and a manager How AI support can leave more room for human buyer contact Why selling a business creates a cash-flow replacement decision How 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

September 29, 2026Episode 3128 min

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 Promissory How everyday estate planning differs from pre-exit trust planning What QSBS means and why company eligibility is only part of the question Why option vesting and stock acquisition are different events How acquisition dates affect holding-period and exclusion rules Why federal and state tax treatment can differ How company growth can affect newly issued stock What founders weigh when converting an LLC to a C corporation Why acquisition consideration and deal structure matter personally Why Brian encourages individual counsel for founders When Brian prefers to begin trust planning How gifting shares changes ownership and control Why vested options can still require cash at departure What employees can ask about early exercise Topics 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

September 22, 2026Episode 3044 min

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 company How an acquisition can benefit founders and investors differently How his first syndicate pooled smaller checks Why distributions matter alongside paper valuations How a secondary sale repaid one fund in Adam's account Why investor communication changes the ownership experience Why he is reducing his personal early-stage allocation How he approaches later-stage SPVs and trusted introductions Why business expertise does not automatically transfer to investing How frugality can become difficult to turn off Where spending buys useful time and reduces household friction How Sam and Adam weigh ambition against personal financial stress Topics 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

September 15, 2026Episode 2928 min

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 CPA How the founder’s next business or lifestyle affects the exit plan How Brett describes the seller-to-trust-to-buyer sequence Why the seller becomes a lender under the note structure How investment approvals divide control What happens in Brett’s example when assets underperform the note rate How principal and interest affect the payment discussion Why lifetime cash needs and inheritance goals can pull in different directions Why a basis adjustment and estate tax address different issues How Brett frames creditor protection and diversification Why entrepreneurial success does not establish investing skill How 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

September 8, 2026Episode 281 hr 7 min

Why Franchises Could Win the AI Economy | 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 allocation Why investing after an exit can feel unfamiliar How Andy combines broad venture exposure with active private ownership What separates a franchisor investment from franchisee ownership Why taking cash out can compete with funding expansion How royalties and service fees change a brand’s economics What a hypothetical 100-unit expansion requires in capital and people How operating scale can change a franchise portfolio’s buyer pool Why property ownership and business ownership need separate analysis How owner incentives and franchisee profitability interact Why Andy sees an ownership opportunity in white-collar disruption What attracts him to recurring B2B services and care businesses How 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

September 1, 2026Episode 2739 min

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 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

August 25, 2026Episode 2645 min

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 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

August 18, 2026Episode 2543 min

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 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