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.

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#passiveinvesting #realestateinvesting #syndications #alternatives #privatemarkets #marketcycles #limitedpartners #mechanicsofmoney

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/

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Website:
https://silvermancapital.com

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#venturecapital #preseed #startupinvesting #b2bsoftware #angelinvesting #wealthstrategy #privateinvestments #mechanicsofmoney

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

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#financialtherapy #moneyandmarriage #wealthpsychology #behavioralfinance #financialinfidelity #moneymindset #raisingwealthykids #privatemarkets #personalfinance #mechanicsofmoney

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

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Website: https://silvermancapital.com

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#creditcardpoints #pointsandmiles #travelrewards #awardtravel #businessclass #luxurytravel #travelhacking #mechanicsofmoney #businessowners #smartmoney

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

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#exitplanning #founderpsychology #postexitlife #transactionillusion #mechanicsofmoney #wealthmanagement #privatemarkets #entrepreneurship #founderexit #capitalallocation

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 bills
• The $100M family that skipped the prenup on purpose, and what the wife discovered in the divorce
• Why the ultra wealthy own nothing but control everything
• What exit tax planning is worth: typically 10-30% of the purchase price
• The proprietary structure that turns $2M invested into a $20M paper loss
• What tax "risk" actually means: audit odds by income bracket, case law, and opinion letters
• Phantom gains, partnership allocations, and depreciation arbitrage
• Noah's real estate arc: a decade of 27% IRRs, then deals returning 40 cents, 20 cents, or zero
• Losing tens of millions of investor capital, and rebuilding with gratitude
• Why his new capital only goes into his operating business and public markets
• His 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

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#taxstrategy #taxplanning #exitplanning #wealthbuilding #familyoffice #privatemarkets #mechanicsofmoney #entrepreneurship #capitalgains #realestateinvesting

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 fund
• Why she walked away from a multi-six-figure brokerage business at its peak
• What relocating a family abroad actually costs, and why "it's cheaper" is a myth
• Whether managing capital remotely helps or hurts credibility with investors
• Diversifying across verticals and the capital stack, not just asset classes
• Matching deals to an investor's actual buy box and stage of life
• Why fund-manager compensation weighted toward exit keeps interests aligned
• What real due diligence looks like: underwriting, whisper networks, background checks
• The large-name sponsor deal she passed on, and what the capital stack gave away
• Why she turns down almost everything sent to her inbound
• Her one piece of advice for relocating and for breaking into the space: bet on yourself

Topics 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

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#realestateinvesting #fundmanagement #privatemarkets #alternativeinvestments #duediligence #accreditedinvestor #mechanicsofmoney #lifebydesign #passiveincome #wealthbuilding

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 gap
• Why mastering one core solution before diversifying was the catalyst for scale
• The "water faucets" framework for predictable, repeatable growth
• How picking the wrong market size can quietly kill your ambitions
• Income tiers from $10K/month survival to generational wealth, and what changes at each level
• Mapping out what your dream lifestyle actually costs, then reverse engineering toward it
• Why Arman chose a strategic partner over private equity, and what an 18-month search process looks like
• Personal capital allocation: real estate, alternatives, managed wealth, and letting money compound
• Why investing in your primary residence might be the single best lifestyle investment
• The case against grind culture, and how to build ambitiously without burning out

Topics 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

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#entrepreneurship #ecommerce #servicesbusiness #wealthbuilding #lifebydesign #privatemarkets #mechanicsofmoney #capitalallocation #alternativeinvestments #generationalwealth

What do 8,000 millionaires actually do with their money, and what can you learn from the patterns?

Sam sits down with Tad Fallows, co-founder of Long Angle, a community of over 8,000 high- and ultra-high-net-worth members focused on managing wealth without anyone trying to sell them something. Tad bootstrapped a SaaS company to ~100 employees and a successful exit, then built Long Angle from a few dozen friends into one of the largest private wealth communities around, and he's been benchmarking how its members invest, spend, and think for years.

In this conversation:

• Why most companies shouldn't raise venture capital — and the quiet power of bootstrapping
• The net-worth tiers where life actually changes, and where it surprisingly doesn't
• How the wealthy really spend: buying back time vs. flexing, travel, and quiet wealth
• Rent vs. buy, 2.5% mortgages, and why the housing market is frozen
• How members allocate: roughly half public equities, a third in PE and alternatives, the rest in home equity, bonds, and cash
• What makes a great fund manager — investing alongside institutions, GP skin in the game, fees, and specialization
• The ladder for emerging managers, from friends-and-family capital to institutional checks
• Where Tad sees opportunity now: co-investments, secondaries, and upstream oil & gas
• Why being a smart, educated client beats handing it all to a manager

Topics covered: high net worth, wealth management, bootstrapping, SaaS exit, venture capital, private equity, asset allocation, alternative investments, secondaries, oil and gas, real estate, rent vs buy, estate planning, family offices, emerging fund managers, fundraising, roll-ups, financial independence

Guest: Tad Fallows, Founder, Long Angle | https://www.longangle.com

Newsletter: https://www.mechanicsofmoney.co
Website: https://silvermancapital.com

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#highnetworth #wealthmanagement #investing #privateequity #alternativeinvestments #privatemarkets #mechanicsofmoney #financialindependence

Mathew Owens is a CPA who quit his corporate job in 2006, got hit by the 2008 crash, lost everything, and paid back every investor before rebuilding from scratch. Today, he's flipped over 1000 houses, raised $200M+ in private capital, lent $500M+ to flippers, and runs a cannabis farm in Maine alongside litigation finance and alternative investment strategies.

In this episode, Matt breaks down how he allocates capital across real estate, alternatives, and direct business operations, and why he believes diversification across uncorrelated asset classes is the key to long-term stability. He also shares his CPA-level tax strategies for W-2 earners and high-net-worth investors, including cost segregation, the short-term rental loophole, and why California is the worst state for taxes.

🔗 Mathew Owens' 200-Point Due Diligence Checklist: MatthewOwens.com

We cover:

• How Matt went from CPA firm burnout to flipping 1000+ houses and raising $200M+
• The mindset shift that got him through losing everything in 2008
• Why he diversifies across real estate, litigation finance, cannabis, and promissory notes
• Velocity of money and why redeploying capital fast matters during wealth-building
• How litigation finance works and why it's uncorrelated to real estate
• His 200-point due diligence checklist for vetting sponsors and operators
• Tax strategies for W-2 earners: cost segregation, RE professional status, and the STR loophole
• Why California is the worst state for taxes and what you can (and can't) do about it
• Inside the Ellipse cannabis farm: the business plan, team, and growth strategy
• What asset classes excite and concern Matt right now, including AI's impact on real estate