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

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Website: https://silvermancapital.com

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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

Everyone makes content about buying businesses. But once the deal closes and you actually have to grow the thing? That's where the real playbook starts, and almost nobody talks about it.

In this episode of the Acquisitions & Asphalt series, Sam Silverman and Chris Wirthlin break down exactly what it took to prepare Nationwide Paving for aggressive growth: the systems they overhauled, the employees they had to get bought in, and the processes that would've completely broken at scale if they hadn't fixed them first.

They cover:

• Why growth fundamentally introduces risk into a business, and how to map out those risks before you start scaling
• The employee buy-in problem: Why pushing for growth without bringing your team along can cost you 10-15% of your workforce overnight
• Career pathing in blue-collar businesses: How showing a rake man the path to foreman to superintendent changes retention completely
• Why quality control via FaceTime calls works at 5 jobs a day but completely falls apart at 25
• The 6-month preparation framework: 3 months identifying broken processes, 3 months optimizing, then pushing growth as hard as possible
• Proactive maintenance plans: How free inspections and planned capex turn reactive property managers into sticky recurring revenue clients
• The real cost difference between preventative maintenance and full repaving, roughly $20K vs. $100-150K
• Organic growth vs. acquisition: The tradeoffs, why Phoenix didn't respond to the same playbook as 30 other states, and why the best strategy combines both
• IT infrastructure reality: Getting acquired companies off pen and paper when your chief estimator's "software" turns out to be a literal yellow legal pad
• How to systematize "founder magic" in bidding, turning unconscious competence from 25-year veterans into repeatable, accurate estimating software

Learn more about The Pave: https://thepave.co/
Learn more about Silverman Capital: https://silvermancapital.com

What if the best market signal didn't come from Wall Street — but from 3,500 retail traders on social media?

Sam sits down with Vuk Vuković, co-founder of Oraclum Capital, a systematic hedge fund that uses crowdsourced intelligence and network science to trade weekly S&P options. Vuk and his co-founders originally built their methodology to predict elections — calling both Brexit and Trump in 2016 — before applying the same framework to financial markets.

In this conversation:

• How wisdom of crowds and network analysis extract signal from noise in elections and markets
• Why weekly options over prediction markets like Kalshi or Polymarket
• Using network science to filter echo chambers and identify whose opinion actually carries weight
• Building a fund designed to be uncorrelated to the S&P during market drawdowns
• The fundraising grind as an emerging manager with no traditional finance background
• European vs American incentive structures and why they produce different kinds of entrepreneurs
• Vuk's blunt one-word advice for aspiring options traders

Topics covered: hedge funds, options trading, prediction markets, wisdom of crowds, network science, echo chambers, S&P 500, emerging fund managers, fundraising, EU vs US business culture, risk management, Kalshi, Polymarket

Guest: Vuk Vuković, Co-Founder & Fund Manager, Oraclum Capital | https://www.linkedin.com/in/vuk-vukovic-oraclum/

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

Subscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth.

#hedgefund #optionstrading #predictionmarkets #alternativeinvestments #crowdintelligence #privatemarkets #mechanicsofmoney #investing

Most high earners are told the same thing: your W-2 salary can't be sheltered. Tait Duryea built a firm proving otherwise.

In this episode of Mechanics of Money, Sam Silverman sits down with Tait Duryea: third-generation airline pilot and founder of Turbine Capital, now the largest airline pilot investor network in the world. They unpack why oil & gas is one of the few asset classes that lets W-2 earners offset active income, why the "industrial vacancy crisis" is mostly a measurement error, and why Tait believes the next decade belongs to owners of hard assets, not holders of dollars.

In this conversation:

• Why a narrow niche beats a broad audience when you're raising your first capital
• The real story behind industrial vacancy, and where the sub-2% pockets actually are
• Senior housing and the demographic "silver tsunami" almost nobody is building for
• How non-operated working interests create year-one tax write-offs
• The macro case for hard assets in an era of money printing
• Why Tait is rotating toward private debt as net worth grows

Topics covered:
Tait's background as a third-generation pilot • building a niche investor network • the LP-to-GP path in real estate • industrial real estate and the vacancy myth • senior housing and demographic tailwinds • operating vs. partnering on deals • the case for oil & gas • tax treatment of working interests • building an investment team in-house • money supply and the dollar • interest rates and real estate values • the future of Turbine Capital • private debt and cash flow • travel and life off the clock

Guest: Tait Duryea, Turbine Capital
https://www.linkedin.com/in/taitduryea/

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Website → https://silvermancapital.com

If you're an accredited investor or family office, subscribe for new conversations every week.

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Alec Todd is the co-founder and CFO of Cove, the lifestyle apparel brand you've probably already seen all over your Instagram feed. He and his twin brother Sean built Cove from a $3,000 investment into a $100M/yr revenue machine, fully bootstrapped with zero outside money.

In this episode, Alec breaks down exactly how they did it: the mindset, the financial discipline, and the unconventional moves that got them there.

What we cover:

• How Cove went from $3K and a heat press to $100M/yr in revenue
• Why they turned down investors for 7 years, and why that's changing now
• The twin-run financial structure behind Cove's growth
• Why hunting for the exit is the wrong play, and what to do instead
• How Alec thinks about building and protecting wealth as a founder
• "Memory dividends" and the Die with Zero philosophy

Follow Alec on Instagram: @alec_todd
Learn more about Cove: coveusa.co

Risk tolerance isn't about bravery. It’s a mathematical formula based on your life stage, your sunk costs, and your monthly overhead.

In this solo session of Mechanics of Money, Sam Silverman explains why a 22-year-old often has a much higher capacity for risk than a 50-year-old professional making $600,000 a year.

If you’ve ever felt like you can’t afford to quit your high-paying job to build the business you actually want, or if you're wondering how to adjust your portfolio as you age, this episode is a reality check on the "Golden Handcuffs."

What we discuss in this session:

• The Zero-Obligation Advantage: Why your early 20s is the absolute best time to take massive, "selfish" risks before lifestyle creep sets in.
• The Sunk Cost Profile: How years of education, medical debt, and high lifestyle costs drastically lower the risk tolerance of established professionals.
• Calculating Your "Spread": If you earn a dollar and spend 50 cents, that 50-cent delta is your true risk capital.
• The Optionality Buffer: Why Sam intentionally kept his cost of living at $7,000/month while climbing the corporate ladder, and why replacing a $25,000/month burn rate is a nearly impossible hurdle.
• The Retirement Shift: Why your strategy must pivot toward liquidity and short-term yield as you near retirement.

Silverman Capital is a private markets allocation platform built for cash flow and risk clarity. We solve the yield and diversification needs of family offices, accredited investors, and sophisticated W-2 earners.

Connect with Silverman Capital:
Website: https://silvermancapital.com/
YouTube Channel: https://www.youtube.com/@SamSilvermanOfficial

Wall Street suits think they can roll up blue-collar businesses with just a spreadsheet. But without true boots-on-the-ground experience, they usually end up buying a fleet of broken equipment and alienating the entire workforce.

In this episode of the Acquisitions & Asphalt series, Sam Silverman brings on Jeff Livingston (CEO/Operating Partner of Nationwide Paving) and Chris Wirthlin (CFO of The Pave) to break down what actually happens when you pair a sharp financial team with a 30-year paving veteran.

They break down the "Anti-PE" approach to acquiring service businesses, and pull back the curtain on how to find massive hidden margins that financial due diligence completely misses.

They cover:

• Why traditional private equity fails at service-based roll-ups, and how to actually win the trust of legacy founders
• The psychology of acquisitions: How taking over back-office billing turned an "I'm retiring in 6 months" founder into an "I'll stay 'til I'm 80" partner
• Due diligence secrets: Why the crew in the field will tell you the truth about a company long before the owner's financials ever do
• Equipment reality checks: How to spot "junk" machinery that standard financial appraisals completely miss
• Finding hidden cash: How bringing subcontractor work and traffic control in-house instantly saved $10,000 a day
• The power of geographic density: Building economies of scale by sharing yards, equipment, and corporate infrastructure across regional footprints
• Dominating corporate contracts: How to win national accounts (like Wells Fargo and CVS) with 24-hour proposals and insane operational speed
• The Buffalo CVS case study: The logistics of flying a single operator 1,000 miles to fix a pothole and still maintaining high margins

This is a weekly series. New episodes every Tuesday.

Learn more about The Pave: https://thepave.co/
Learn more about Silverman Capital: https://silvermancapital.com

Climbing the Big 4 partner track is supposed to be the ultimate career goal. But for those on the inside, it often just feels like pledging a 10-year corporate fraternity.

In this episode of the Acquisitions & Asphalt series, Sam Silverman brings on Alex Loebig, Head of Corporate Development for The Pave, to discuss why she walked away from a 12-year career at GE Capital and Deloitte to dive into the gritty world of blue-collar M&A.

They break down the psychological shift required to leave the Fortune 100, and pull back the curtain on what Post-Day 1 integration actually looks like when you acquire a 30-year-old Mom-and-Pop business.

They cover:

• Why the corporate partner track is changing, and why the delayed gratification may no longer be worth it
• The "MBA Dilemma": Is business school actually worth the time and opportunity cost?
• How to slowly flex your "risk muscle" without blowing up your personal life or bank account
• The reality of Post-Day 1 integration: Why your shiny new CRM means nothing without employee buy-in
• How to build immediate trust with blue-collar founders when you are the "corporate outsider"
• The low-hanging fruit of M&A: Moving acquired companies from personal piggy banks to GAAP compliance
• How taking back-office stress off a founder allowed them to double their paving bidding capacity
• Spotting red flags during due diligence: Work In Progress (WIP) and the hidden impact of safety protocols
• The "Suits" Illusion: Why buying a business isn't just glamorous negotiations (and why ego kills partnerships)

This is a weekly series. New episodes every Tuesday.

Learn more about The Pave: https://thepave.co
Learn more about Silverman Capital: https://silvermancapital.co

Retail buyers fight to the death over the multiple. Institutional buyers obsess over the deal structure.

In episode 3 of the Acquisitions & Asphalt series, Sam Silverman and Chris Wirthlin explain why the price you pay for a company matters far less than the terms you dictate. 

They break down the five structural levers that actually determine if an M&A deal survives its first year, and share the exact capital stacks behind their latest multi-million dollar acquisitions.

They cover:

• Why buying a business based only on the EBITDA multiple is a trap
• The 5 critical levers of M&A: Debt, Earn-outs, Seller Carries, Investor Capital, and Working Capital
• The reality of SBA loans vs. Regional Banks, and why credit agreements matter
• Why they avoid earn-outs in blue-collar businesses (and what they use instead)
• The "Working Capital Trap" that secretly raises your purchase price after closing
• How a seller tried to pass off broken, painted equipment as operational assets
• Real deal breakdowns: The exact math and leverage used to fund their Texas and new $12M acquisitions
• Q&A: How to negotiate a 0% interest seller note, deal sizing, and off-market sourcing

This is a weekly series. New episodes every Tuesday.

Learn more about Silverman Capital: https://silvermancapital.co