You buy equity. You're last in line. Your money is committed for three to five years, and what you make depends on what the asset is worth when it sells. You get a projection and a wait.

That seat is fine. I own plenty of it. But it's one seat out of several, and the reason you keep getting shown it is that it's the seat sponsors need filled, not the one that necessarily fits you best.

Here are three others. I'll use what we're actually doing this year as the example, because made-up examples teach badly.

SEAT ONE

Be the bank

Every business you've ever admired had a stretch where it needed money faster than a bank would move. The bank isn't wrong to be slow. It's underwriting a five year relationship. The business needs an answer this week.

That gap is a business. Somebody funds it, and they get paid for speed rather than for taking a view on where the economy goes.

The thing to understand about lending to small businesses is that the whole game is spread. One borrower going bad is not a risk, it's a certainty at some volume. What matters is whether you've done enough of them, across enough industries, that the bad ones are already priced in. This is why a book of a hundred and fifty loans across eighty industries behaves nothing like a book of ten.

It's also why the honest question to ask any lender isn't what they yield. It's how many loans they've made and what happened to the ones that went wrong.

SEAT TWO

Own the boring business

Here's a number worth sitting with. A software company trades at twelve times earnings or more. A paving company trades at three to four.

That gap isn't a reward for taking more risk. It's a reward for showing up somewhere nobody else wants to be. The seller is 63, has no succession plan, and there are three plausible buyers instead of thirty. Price follows the number of bidders far more reliably than it follows quality.

The part people underestimate is what comes after. Buying cheap is the easy half. The hard half is that these companies usually run on the founder's memory. No systems, no reporting, no second layer of management. We spent the last twelve months building operations, accounting, IT, finance, and go to market across the platform. None of that is fun to write about, and it's what separates a group of acquired companies from a platform.

If you take one thing from this section: the multiple you buy at is decided by how few people want the deal. The return you get is decided by what you do in the twelve months after.

SEAT THREE

Sell time, not money

This one most people have never heard of, and it's the most interesting of the three.

A sponsor has a property under contract. The lender is ready. They need ten million of equity and they've raised eight. Closing is in three weeks.

Miss that date and the deposit is gone, the seller moves on, and the rate lock expires. All three cost more than the money does. So the sponsor has three options. Call every investor again and hope. Give up a piece of the promote they spent a year earning. Or borrow the gap for ninety days, close on time, and finish the raise from a position of strength.

The third option is usually the cheapest, even at a rate that sounds expensive, because it's paid in months instead of in a permanent slice of the deal. That's the part worth internalizing. A high monthly rate on a short clock is often cheaper than a small percentage of forever.

We've done more than a hundred of these. The lesson that took the longest to learn is that you aren't underwriting the property. You're underwriting whether the sponsor can replace the capital on schedule. Those are completely different questions, and the second one is far more knowable.

The three side by side

Stacked by how long your money is committed:

Read down the last column. Three different things have to go right, and none of them is the same thing. That's what people mean by non correlated, and it's a much more useful definition than the one that involves charts of gold prices.

None of the three needs rates to fall or cap rates to compress. That isn't luck. It's the filter we run everything through.

All three of these are open right now. I'm not putting terms in a newsletter, because what fits depends on what you already own and what's already paying you.

If you want to see how one of them actually gets underwritten, I'm happy to walk you through a real deal. What we looked at, what we passed on, and what has to go right for it to work. Grab time here.

- Sam

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Megan McCoy is the first Certified Financial Therapist. She runs the personal financial planning program at Kansas State, co-edits the Financial Planning Review, and is a licensed marriage and family therapist. She got into this during the Great Recession, when her faculty started training family therapists alongside financial planning students. She sat next to a planner while treating clients and never went back.

Most of what we cover on this show is structure. Deals, terms, tax. This one was the other half, and it was more useful than I expected.

Here are the parts worth your time.

The $20 experiment

Researchers go to a college campus. They hand half the students $20 and tell them to spend it on themselves today. They hand the other half $20 and tell them to spend it on someone else. They call everyone that night. The students who spent it on someone else are happier.

That part I would have guessed. Here's the part I wouldn't have.

They run it again. This time they tell the students up front that the giving group ends up happier. The students say that's fine for other people, not me, I'd rather keep it. So they force them to give it away anyway. Same result. Knowing the trick didn't break the trick.

Then they put people in an MRI. Think about giving to charity, the happiness center lights up. Get handed $20 to give to charity, it lights up. Get told you're being forced to give against your will, it still lights up.

Megan's version: $20 on a beer for a friend beats the same $20 on a beer at home.

Her three categories for spending that actually moves the needle are small purposeful splurges, experiences, and spending on other people. And she made a point about experiences I liked. An experience isn't a category, it's a function. She's not a video game person, so a video game would be a dead purchase for her. Her brother plays online with friends every week, so his video game is an experience. Same receipt, different thing entirely.

Nobody is talking about this

Her own research found that 70% of people hadn't talked to a living soul about money in the past year. Not a spouse, not a friend, not an advisor. A full year.

That number explains a study she cited: financial planners accidentally make marriages better. Not financial therapists. Regular planners. The mechanism is that a planning meeting is the only room where a couple is required to say out loud what they want and what they're afraid of.

Her one directive piece of advice, and she was clear she doesn't like giving directives, is to get a joint account. Two reasons. People make fewer purchases they quietly know they shouldn't. And transparency goes up.

What's behind it is financial infidelity. Hiding wealth, hiding debt, hiding a purchase, lying about when you bought something. She says it damages a relationship at close to the level of actual infidelity. That one landed.

And the sharpest thing she said all episode: if you want a separate account because you don't feel you have enough power in the relationship, that's a canary in the coal mine. The account isn't the problem. Wanting it is the signal.

The prenup argument I'd already made in business

Megan reframed prenups in a way I hadn't heard. Most people hear prenup and think it takes the romance out, or that it means someone's in it for the money. She flips it. Once the prenup exists, money stops being a reason you're together. It becomes a consequence of the relationship instead of the glue holding it up.

I'm pro prenup and I'd add the operational case. We recently mapped out the full breakup terms of a business partnership while everything is good. Nobody's hurt, everybody's rational, eyes are open. That document probably saves seven figures in legal fees and a lot of stress. You can't negotiate well from inside a fight.

She also flagged something I didn't know. There's a group training financial planners specifically for divorce work, because lawyers routinely split retirement accounts without accounting for pre-tax versus post-tax. They divide the number, not the value. Real money gets destroyed in that step.

Her closing note was about unseen labor in a skewed-income household. She quoted Buffett, the best financial decision you make is who you marry, and her point is that the support has a value even when it never shows up on a statement.

Nobody has priced out their own dream life

Megan's point is that the future stays vague on purpose. Ask someone about their dream and you get the Eiffel Tower and a safari. No detail. Detail is what makes you realize what you actually want.

She does this with clients who say they can't wait to retire and buy the lake house. Okay. How often are you actually there? What happens in winter when you're worried about the pipes freezing? How many mosquitoes? What's the hidden labor you're not counting?

I hear the same thing in a different form. Someone tells me they need six or seven million a year. That's half a million a month. Try to actually spend that. What you find is you can live exactly the way you want for a fraction of it.

I've run the math on my own version. If I had 10 or 20x what I have now, the only real change is a better primary residence where I can host people. Flying private is the next step up and it's still a bad trade on dollars per unit of happiness.

Her fix is smaller goals you can actually hit instead of one plan ten years out. She and her husband do a quarterly lottery ticket date. They buy a Powerball they know they won't win and spend the night on what would be different if money were no object. What chores would go. Who they'd see more of. What they'd pursue. Most of the answers turn out to be things they could do tomorrow for very little.

I'd add my own version of this. Try before you buy. I was sure I wanted to live a month at a time in different cities. I have two dogs. It was miserable. Crossing things off is most of the work.

What you teach your kids without saying anything

Two things here.

The first is congruency. Megan's view is that the worst thing you can do as a parent is believe one thing about money and do another. Kids read the behavior, not the lecture. Get your own story straight, and get on the same page as your partner, before you try to teach anything.

The second one stuck with me. In a lot of families we socialize boys to earn and girls to save. Nobody decides to do it. It shows up in small stuff. And she thinks it's part of why women often invest less aggressively later; they were taught to protect, and men were taught to earn.

Her practical example was good. Her oldest wanted a new bat. $400, which is insane for a twelve-year-old's bat, and that's youth sports now. They didn't make her earn $400. They wrote out a list. Practice this much. Clean this much. A few other things. All of it written down and clear. We're supporting you because we want you to succeed, and you have skin in the game.

On enabling adult children: she's written papers on it, her read is that it almost always traces back to the parent rather than the kid. Fear that they can't do it on their own, or guilt about not having been around enough. The more you actually believe your kid can handle it, the less you enable.

I asked her at what age living at home becomes a problem. She wouldn't give me a number, and her answer was better than a number. It isn't age, it's whether there's a plan. You can be 35 and starting law school in three months and that's fine. You can be 18 and playing video games all day and that's a problem.

The part that hit close to home

We got into what happens to your identity when the job goes away. Megan sees it most with people nearing retirement. It's voluntary, they chose it, and it still takes their confidence with it. The whole structure of self-worth was built on the title, the performance, and the number.

I lived a version of that. I was an executive at a tech company with a 50-plus person team, a title, real cash coming in, and a clear place in the pyramid. Then I left to build my own thing and went back to ground zero. Not an expert. Low ranking. Starting over.

If you're taking that kind of risk you have to be genuinely okay being bad at something again. Megan's addition is that you can do the prep work, build the other sources of esteem before you need them, rather than discovering you don't have any the week after you walk away.

Give the full episode a listen. Megan is the rare academic who answers a direct question with a direct answer, and she was willing to use her own marriage and her own kids as the examples.

— Sam Silverman
Silverman Capital

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Colin Stroud runs Go Somewhere. He got into points and miles because he couldn't afford to travel. He had just gotten married, taken a low-paying job, and worked out that real travel with a wife and a baby was not happening. So he went down the rabbit hole. Now he does it full time for business owners and people sitting on large point balances.

I went deep on this myself four or five years ago. I still learned things in this one.

Here are the parts worth your time.

The $30,000 Christmas nobody paid for

A client came to Colin wanting a luxury hotel in the Caribbean over Christmas and New Year's. That is the week hotels can charge whatever they want, and they do.

He got them two rooms at the Park Hyatt in St. Kitts. Thirty-five thousand points per night, per room. The cash rate for those two rooms across the week was north of $30,000.

These were standard rooms. Not suites. The hotel had just tripled the price because it could.

They paid nothing out of pocket.

It cost a real pile of points. But it is a pile that any high earner running spend through the right card can build in a year.

Status is mostly a waste, and I have the receipts

Colin's take on airline status lines up with mine. If you are going to buy the front cabin no matter what, status does almost nothing for you. There is no way to guarantee an upgrade. And on long-haul international, the airlines do not do complimentary upgrades at all. That is exactly the flight where you want one.

His line: it is nice to get upgraded from Atlanta to Indianapolis, but that is not a big deal at the end of the day. That is where the upgrades actually happen.

The exception is the person running $200,000 a month through cards. At that level, buy status with one or two airlines and still earn flexible points on everything else.

Hotels are a different animal, and the programs are not the same.

Marriott Ambassador cannot be bought. Colin's point is that you could put $100 million a year on a Marriott card and they still will not give it to you. You have to stay the nights. He likes that, because it means nobody can fake it. Hilton is the opposite. You could open a credit card and land near the top of their ladder. If everyone has it, nobody has it. Hyatt sits in the middle, and he thinks it is the most valuable status that a normal person can actually reach.

This is the part where I will be honest about my own experience. We had Ambassador. It takes $23,000 of spend a year. Last year we missed it by about $500 and they would not honor it. Marriott is strict.

So now I book the cheapest room in the hotel and negotiate my way up at the front desk. I am fine living with that outcome in a hotel. On a twelve-hour flight I am not.

You are probably earning the wrong kind of points

This is the one that costs people the most and gets the least attention.

Delta SkyMiles and Marriott points are locked. They are only good in one place. Flexible bank currencies from Chase, Amex, and Capital One are not. A hundred thousand Chase points can become a hundred thousand United miles, or Southwest, or Hyatt, or Marriott. You decide later, based on what is actually available.

Colin walked through a client in construction spending about $70,000 a month with two suppliers. None of it in a bonus category. No four-times-points on drywall. They want Europe three or four times a year.

He put them in Capital One. Unlimited two points on every purchase no matter how small, and transfer partners that get them out of Orlando or Tampa on Virgin Atlantic to London or Air France direct to Paris.

The right card is downstream of two things: where your money actually goes, and where you actually want to fly. Most people pick on branding and then wonder why the points do not go anywhere.

The back end is where this stops being a rounding error. I am flying to Italy out of San Diego for 70,000 points on a ticket that prices at $6,000. Measured against two percent cash back, that is somewhere around nine cents per dollar spent.

Do not burn points on a room you could just pay for

Marriott only redeems well at the top of the range. A room running a few hundred dollars, even $600 or $700 a night, is rarely a good use of points. Pay cash for those.

We bank ours and spend them in five-night blocks, because Marriott gives you the fifth night free on points. Stack that with a high-end property and you are getting three, four, sometimes five cents per point.

Colin generally steers people away from Marriott's program. But he agrees that if you only ever spend those points at the St. Regis and Ritz-Carlton end, the value holds up. He knows someone who does a week at the St. Regis Deer Valley every year and gets a consistent one and a half cents a point out of it.

You are searching in the wrong order

If you constantly look for award availability and find nothing, Colin thinks you are asking the question backwards.

Most people ask how to get to the British Virgin Islands on January 16th, landing by four. Fine. You will find nothing.

Flip it. You want somewhere very nice in the Caribbean, sometime in January. Now ask what the best deal in the entire region is.

That is how Colin ended up in St. Kitts in the first place. He was scanning Hyatt properties across the Caribbean, found the best deal by a mile, paid 30,000 points a night, and got upgraded. The cash rate on the room he slept in was $1,700 a night. Call it $300 of points for a $1,700 room.

Two tools make this a lot easier. Seats.aero aggregates award space across the airline programs so you are not opening six websites at midnight. In the last year they added an AI assistant on top of their data for about $10 a month. You can type in that you have 400,000 Amex points, you live in Dallas, and you want your family in business class to Italy, and it will find it and then explain why it is telling you to book a Turkish Airlines flight through Air Canada.

If you are starting from nothing, dailydrop.com has a free course. Colin says twenty minutes with it puts you ahead of almost everyone.

Buy the second flight

If you do not live in a major hub, you will keep losing award value before you even start.

Book the main leg on points. Pay cash for the hop to the hub.

We flew ANA business class from Chicago to Tokyo last year and paid out of pocket for a separate Miami to Chicago ticket to get there. That saved somewhere in the range of $12,000 to $13,000. You do have to leave security, collect your bags, and check them again with a different airline. It is annoying. Do it anyway.

Colin had a client in Kansas City do the same thing for a $200 ticket to Chicago and fly direct to Germany from there.

Get comfortable with the itinerary not being perfect. That is the whole trade.

Give the full episode a listen. Colin is one of the few people in this space who will tell you that you are overcomplicating it and that the answer is on Google, instead of selling you something.

— Sam Silverman
Silverman Capital

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Jerome Myers is a Certified Exit Planning Advisor, the founder of Exit to Excellence, and probably the only person in the space who introduces himself as "the product of bad exits." He built a $20 million division from zero in one year, watched half his team get cut, walked away, and then spent years trying to understand what happened to him psychologically.

He now helps founders navigate what he calls the Founder's Exit Paradox, winning on paper and falling apart in person.

This was a different episode for us. We didn't talk about deal structure or portfolio construction. We talked about what happens to people after the check clears.

Here are the parts worth your time.

The $2B founder who still couldn't answer the question

Jerome was standing in a conference room in Carlsbad, California when a founder who had exited for $2 billion started describing the exact same feelings Jerome had been carrying. Loss of meaning. Loss of relationships. An existential crisis he couldn't name until that moment.

When Jerome asked him how he got out of it, the guy said he'd let him know when he did.

That was the moment Jerome realized nobody was solving this problem. The only resource he could find was a Harvard Business Review article that basically said: congratulations on selling your business, now prepare to be depressed. He decided that couldn't be the reward for 15 to 50 years of building.

Why $15M in cash feels worse than $3M a year

This one stuck with me. Say you're making $3 million a year running your company. You sell for $20 million. After taxes you take home maybe $15 million. On paper, you should feel rich.

But Jerome says most founders feel the opposite. You went from a stream of deposits hitting your account to nothing. You only see the balance go down. And the question that plays on repeat is: how long before I run out?

He calls this the “Transaction Illusion”, the belief that the money is going to make you happy, fulfilled, and free. But money only solves the first two levels of Maslow's hierarchy. Shelter and safety. It doesn't touch love, belonging, purpose, or impact. When the exit doesn't deliver those things, and it never does on its own, the gap between expectation and reality is where depression lives.

60% of your life vanishes overnight

Jerome runs workshops where he has founders list the five people they spend the most time with. Three out of five are almost always people they work with.

Now imagine exiting. Sixty percent of the people you spent your days with are gone. And most of them were what Jerome calls "dear friends", or the people you're close to because of proximity, not because of a deep relationship. Men especially make friends this way. You work next to someone for years, you consider them a friend. But when the proximity ends, the friendship ends too. A lot of founders don't find that out until it's too late.

The Five Scars of Success

Jerome has identified five experiences that shape how founders behave after a liquidity event. The one with the most impact is total financial ruin: not growing up poor, but having lost everything as an adult.

He told me about a client who exited for $44 million. The guy went through bankruptcy earlier in his career. Private credit from personal connections was the only reason he was able to rebuild. After the exit, Jerome couldn't even get him to book a trip to Destin, Florida. He was driving a 15-year-old car. Jerome eventually got him to buy an $80,000 Lexus, and the guy's first reaction was "what are people going to think about me?"

The approach was small steps. Not trying to change the mindset overnight, but showing through small experiments that things won't fall apart if you spend a little. Jerome sends clients like this the book Die with Zero, and he says it's had real impact on how they think about delayed gratification turning into something that actually works against them.

What fulfilled founders actually spend on

I asked Jerome what he's seen people spend money on post-exit that actually made their lives better. The answer wasn't material stuff. It was experiences with people they care about.

He told me about a scholarship he funds at his alma mater. One of the recipients was about to drop out because her parents couldn't afford tuition. She finished her engineering degree debt-free, stayed for a master's, and texted Jerome on Mother's Day to thank him. He said that text meant more to him than any car he could have bought, and he's a car guy. His dream purchase was a Nissan GT-R because his dad's first car was a Nissan Maxima.

The research backs this up. Jerome referenced a longitudinal study that found doing things with people you enjoy is the single strongest driver of life satisfaction. Not doing things alone. Not buying things. Experiences, with the right people.

The purpose formula founders already know

This is the part I want every founder listening to sit with. Jerome says the question you need to answer is simple: who are your people, and what problem do you solve for them?

If you can answer that with clarity and specificity, you're on the right track. If you can't, everything sounds like a good idea, you become a target for other people's agendas, and you end up a supporting character in somebody else's story instead of the main character in your own.

The irony is that founders already know how to do this. It's exactly how you build a business. Who's the customer? What's the problem? How do you solve it? They've done it professionally for decades. They just forget to apply it to themselves.

Give the full episode a listen. Jerome is one of the most thoughtful people I've talked to about what happens on the other side of a big exit, and this conversation goes places we don't usually go on the show.

— Sam Silverman
Silverman Capital

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Noah is a third-generation CPA who has seen money from every angle. He testified in high-net-worth divorce cases, built and sold a family office for divorced women, syndicated close to a billion dollars of real estate, and now runs Wealthrive, a tax strategy firm for entrepreneurs doing seven figures of income or staring down an eight-figure exit.

Here are the parts worth your time.

The family that skipped the prenup on purpose

Noah's client married into a family whose name you would recognize. Hundreds of millions behind them. No prenup. She assumed that was good news.

It wasn't. The family had every asset wrapped in trusts before the marriage. The house she lived in was owned by a trust. The income funding her lifestyle came from a trust. When the divorce came, none of it counted. She expected tens of millions and walked with one or two.

And the missing prenup was the tell, not an oversight. A prenup requires financial disclosures. The family did not want to disclose. As Noah put it, the ultra wealthy own nothing and control everything.

Your accountant is not your strategist

This is the core of what Noah does now, and the frame is simple. Your tax preparer files history. A strategist plans the future. Most entrepreneurs find out what they owe when the draft return shows up in Q1, sometimes on income they never received in cash.

The gap gets expensive at exit. Noah says planning is worth at least 10% of the purchase price on most deals, often 15 to 30%. On the eight and nine-figure deals his firm works on, that's millions left on the table for skipping the conversation.

One example: a structure where a seller with a $20 million gain puts in $2 million and generates a $20 million paper loss in the same tax year. The money inside grows tax-free and comes out tax-free. In one recent deal, the seller kept equity and the ongoing dividends came out untaxed too.

What "risk" actually means

I pushed him on this, because aggressive structures make people nervous. His answer was more useful than the usual hand-waving.

About 15% of returns reporting $10 million or more of income get audited. Under half a million of reported income, it drops below 2%. Most of his clients report under a million because of the strategies themselves, so they sit in the 2% bucket.

Then he walked through the track record on that leveraged-loss structure. Twenty-five years in use, hundreds of returns, part of seven audits. Six closed with no change. The seventh lost in lower court, won on appeal, and the structure was amended so the contested issue no longer exists. That's the homework he wants everyone to do: how long has the strategy existed, how often has it been audited, and what does the case law say.

The decade that ended at zero

This is the part I respect Noah most for sharing. He spent 2011 to 2021 syndicating heavy value-add real estate with high leverage and variable-rate debt. Averaged a 27% IRR for a decade. Then rates doubled in a few months and the same model got crushed. Deals returning 40 cents on the dollar. Some at 20. Several at zero.

He lost tens of millions of dollars of money from people who trusted him, many of them friends. No spin on it. His takeaways were the ones that stick: he could have pulled back the throttle and didn't, because the model was all he knew and it still felt right. And the thing that saved his family was never betting the balance sheet on any single strategy.

His filter now is one question. Does this risk my family's financial security? New capital goes into his operating business and public markets. Nothing else. His reasoning echoes something I believe about hiring: a good hire in your own company produces a return almost nothing passive can match.

The advice for anyone still building

If you're earning half a million or more, Noah's take is you should have a tax strategist you talk to every year, separate from your preparer. Not a one-off trick like the Aspen short-term rental that works for exactly one season, but an actual multi-year plan that fits where your income and your exit are heading.

Give the full episode a listen. Noah is unusually candid for someone who has won and lost at this scale, and the divorce court stories alone are worth it.

— Sam Silverman
Silverman Capital

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Two episodes went out in the last two weeks. Both landed on the same theme from very different directions. What does it actually look like to build something real and then design your life around it, not the other way around.

Here are the parts worth your time.

ARMAN TAHERI

Arman is the co-founder and CEO of TalentPop, a talent solutions company serving e-commerce brands. He and his brother started the business during COVID out of a problem they had to solve in their own company first.

The pivot nobody planned for

Arman and his brother were launching a medical scrubs company right before COVID hit. Production shut down. Instead of waiting it out, they pivoted to selling face masks using the same cut-and-sew contacts in downtown LA. They bought up almost every yard of fabric in the city. That business did eight figures in under a year.

But they never treated it as the real play. It was short-term cash. They took what they learned about scaling a customer service team under pressure and turned it into TalentPop. One solution, one market, for years before adding anything else.

That discipline is what got them to scale. His take is that most people fall into the trap of chasing the next thing the moment they get a little traction. If you are building something with real enterprise value, you need to stay in one lane long enough for it to compound.

The income levels nobody maps out

Arman broke down how he thinks about personal income in stages. The first target is getting to a point where you cover your expenses and still have something left to invest every month. For him that was $10,000 a month as a baseline.

Once you get past that, the question shifts. What does the life you actually want cost? Most people never sit down and answer that. They just keep earning more and spending more. His point is that if you map it out, the number is usually lower than you think. And once you know the number, you can reverse-engineer what the business needs to produce to get there.

The third level is when you are earning enough that the focus shifts from funding your own lifestyle to building generational wealth. Different team, different advisors, different allocation approach entirely.

Why he chose a strategic partner over PE

TalentPop brought in a strategic investor after an 18-month process of evaluating both PE firms and strategic partners. Arman's view was that PE would have meant playing by someone else's rules full time. The strategic partner gave them operational guidance, particularly around budgeting, account management, and growing within their existing client base, while still letting them run the day-to-day.

His logic was straightforward. He wanted to take some risk off the table, protect his family in case of a downturn, and bring in a partner who could teach them things they had not learned yet. Not just capital. Perspective.

The part that applies to most people listening

Arman is not a fan of grind culture. He thinks the heads-down, no-social-life, sacrifice-everything narrative is mostly for show. His version is simpler. Know what season you are in. If you are building, build. But map out what you are building toward, understand what it costs, and do not blow every dollar during the peak years of your earning potential just to end up on the hamster wheel permanently.

He and his brother are planning to buy a home for their parents. That is the kind of goal that sits at the end of being intentional about every stage before it.

SARAH MISKELLY

Sarah was a real estate broker in Toronto. She grew up in the business with her dad managing multifamily properties, went into sales, and built a multi-six-figure brokerage working seven days a week. Then she shut it down, moved to Costa Rica with three kids, and started over in fund management.

Golden handcuffs and the exit nobody plans

Sarah saw the trajectory. She was building a million-dollar brokerage. But she also saw the ceiling. There is no equity in a sales business. You trade time for commissions, and no matter how good your systems are, the business does not sell for a meaningful multiple when you leave.

So she did two things while she was earning. She invested her commission checks into real estate as an LP and into private lending. And she always had a plan to exit. Not an exit from a company. An exit from the model itself. That cash flow from her investments is what gave her the optionality to walk away and rebuild on her own terms.

The deal she passed on that blew up

This one is worth the listen on its own. A large multifamily sponsor reached out to Sarah directly. Class A property, impressive pitch deck, strong reputation, and they were offering attractive terms to get her capital in.

She dug into the underwriting. The debt service coverage ratio was tight, barely above one. And there was a large preferred equity position sitting above the common equity her investors would be coming in at. The capital stack told a story the pitch deck did not.

She passed. Six months later, multiple deals from that sponsor were losing investor capital. Part of the reason they were pushing so hard to bring in new capital was that the GPs themselves wanted out of their own positions.

Her takeaway is simple. Look beyond what you are being offered. Look beyond the deck. Dig into what could go wrong and ask why this deal needs your money right now.

What it actually takes to run a business abroad

Sarah is clear that living in Costa Rica is not cheaper. Her town has quality schools, good amenities, and a strong expat community, but you pay for it. She still pays into the Canadian tax system. Her family had to set up private medical care. Her son got airlifted to a hospital a few weeks ago because they are in a small town.

The part most people miss is that it is possible if your business runs from a laptop and you can sustain income remotely. Her entire investor base is US-based and SEC-regulated. The Costa Rica part does not show up in the business operations. It shows up in the fact that she surfs before work and her kids speak Spanish.

Her read is that most people do not see it as a possibility for themselves. That is the real barrier. Not logistics.

Both episodes are worth going deeper on. Give them a listen.

— Sam Silverman
Silverman Capital

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Tad built Long Angle, a private community of over 8,000 people worth $5 million to $100 million and up. Most of them are first-generation wealth. He sees how this whole class actually handles money, and he shared the real numbers with us.

Here are the parts worth your time.

The bootstrap math nobody talks about

Tad bootstrapped a SaaS company to 100 employees and sold it. No big venture round. His point was simple. Most companies are not VC companies. If your market caps out at a few hundred million, a giant raise just buries you under liquidation preferences. You exit for $60 or $70 million and walk with $3 or $4 million after the pref eats the rest.

A $10 million personal exit puts you in the top 1% of this country. And it is far more reachable than a $150 million exit that nets you the same $10 million after everyone else gets paid. His rule is that the longer you can wait to take money, the better the terms when you finally do.

What people worth $5M to $50M actually buy

The savings rate surprised me. On average his members save about 50% of their post-tax income. Somebody earning $2 million in California keeps a million after tax and still banks half of that.

They do not spend it on cars or houses. Housing runs 10 to 20% of net worth for most of them. The big discretionary bucket is travel.

The stuff people agree on buying is time. A CPA, a nanny, a personal trainer, anyone who hands hours back. The stuff that gets no love is the flex. Ferraris, Rolexes, branded clubs. Most of this group finds it gross. They want the convenience and the service. The logo does nothing for them.

The US wealth gap is wild

To sit in the top 1% in America you need about $12 to $13 million. In France or the UK, $3 million gets you there. The only European country that matches the US is Monaco, which is basically a tax shelter the size of half a borough.

How his community picks managers

This section is gold if you invest as an LP. Here are a few of the filters he uses:

• Invest alongside institutions. If the Stanford and Duke endowments are in the fund, someone with real leverage already beat the manager up on fees and diligence. If a fund is chasing doctors and dentists instead, ask why the pros passed.

• Skip fund 1 and fund 2. Too much variance, not enough track record. He wants to see cycles.

• Watch the GP's own check. When the operator has a quarter of a billion of his own money in an oil and gas fund, he drills carefully.

• Hold the line on fees. He passed on a deal where the “80/20 split” turned out to be 80% to the GP. Real number. Real pitch.

• Back specialists. The energy guys who grew up in Houston, studied petroleum engineering, and live in the Permian post 40 to 70% IRRs. The generalist dabbling in energy on the side does not.

Where the money is moving now

Here are three areas Tad likes right now:

• Co-invests. Getting into names like Anthropic and SpaceX through a fund's overflow allocation, at low fees and low carry, with a higher hit rate than early venture.

• Secondaries. Buying out LPs who need liquidity, sometimes at 50 to 70 cents on the dollar in real estate. You skip the J-curve and often get your capital back faster.

• Upstream oil and gas. Fracking took most of the guesswork out of the geology. Good operators are seeing sub-year breakevens, closer to six or seven months right now.

The part that hit close to home

We got into boring businesses. The “guys in trucks” world. Med spas, HVAC, plumbing, paving. Tad's honest read is that the roll-up trade has gotten more crowded, and returns that used to look like 6x might compress to 2 or 3x.

He still likes the model. And when I told him paving is our world, he made the point that matters most. Paving is defensible. Hard to compete away with AI. The edge comes down to discipline. You buy well and operate, or you overpay just to collect a management fee.

Give the full episode a listen. Tad is one of the sharpest and most straightforward operators I have had on.

Join us next Tuesday

I am moderating a live panel on investing in debt to build cash flow. The four panelists have raised over $500 million across asset classes in the last five years, a good chunk of it in debt and credit. Chris Larsen, Mathew Owens, Chris Wirthlin, and Patrick Grimes.

July 7th at 7pm EST. All are welcome. Register below and bring your questions.

— Sam Silverman
Silverman Capital

P.S. Planning more of these. If there is a topic you want covered, or you think you belong in one of these seats, reply and tell me. I want to pull future panelists from this community.

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Two quick wins from the platform this quarter, and one new development behind them. Cornerstone just posted its strongest quarter on record. Nationwide is stringing together record months back to back with most of its runway still ahead. And we are under LOI on our fourth acquisition, a concrete company in Dallas. Here is the detail on each, plus what we are building to fund the next leg.

Cornerstone Paving

Q1 revenue came in at $9.21M against $6.86M in the same quarter last year. That is 34% growth, on audited books. We added a fifth crew and grew headcount to get there, which compresses margin for a quarter while new capacity ramps.

The new sales team changes what that capacity can chase. Cornerstone's backlog is heavy in DOT work, which is steady but lower margin. As the sales hires open up more commercial opportunities, we can be more selective, working through the DOT backlog while layering in higher-margin commercial jobs when they are available. Same crews, more profitable revenue. That is margin expansion without adding a dollar of fixed cost.

Nationwide Corporate

Nationwide keeps setting records. May came in around $2M, a record month at the time. June is tracking to $2.8M, another record. July is set up for $4.5M and higher if the weather holds. That is more than 2x in ninety days.

What makes that climb matter is how little of our runway it uses. Nationwide books about two weeks out, so these records are coming off near-term work, not a long backlog we are grinding through. The calendar ahead is still open, and we are already setting records against it. To press that, we hired four additional salespeople, two of them in Texas ahead of our growth there. We doubled capacity to get this far, and the anchor of the platform is producing like the anchor.

The Cost of Growth, and What We Are Building For It

Here is what those record months do not show on their own. We paid for all of it up front. The crews, the materials, and the fuel behind May's record, June's bigger record, and July's bigger-still record all went out the door before a single invoice from those months came back.

Our terms run net 90. We finish the work, send the bill, and wait three months for the cash. That is the mechanic behind everything above. Each record costs more than the last to produce, at roughly the same ratio of expenses, so the faster we grow, the more we are fronting and the longer it sits out before it comes back. We have grown more than 2x in ninety days and have not collected a dollar from those record months yet. That is not a problem with the business. That is the business working exactly as designed. It is also the single biggest call on our cash.

So what are we doing about it?

We are standing up a structured finance division to fund our receivables. Rather than wait out that net 90 to collect, we finance those receivables and put the cash back to work on the next job. It turns the cost of growth into a managed line instead of letting working capital set our speed limit.

The division is built to be conservative by design. It only advances against work that is already complete and accepted, and every advance is secured on both sides:

• The receivables themselves, acquired at a discount to face value, and only once the jobs are completed and signed off on by the client

• The mechanics liens behind the completed work

The added liquidity does something else worth naming. When we can pay our vendors early, we earn early-payment discounts on materials, which lowers our cost on every job. The facility does not just close the timing gap. It makes the underlying work cheaper to produce.

This is the next piece of the platform we are building, and it is built to do two things at once: keep our own growth fully funded, and create a place for investors to put capital to work alongside us against real, completed receivables. We are finalizing the structure now and will share the details soon.

— Sam Silverman
Silverman Capital

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A guy in our industry has spent years buying paving companies.

On one deal the appraisal said two million dollars of equipment. He closed. He walked the yard. The equipment was junk.

He spent close to eight hundred thousand dollars fixing machines just to get through work that was already sold. That cost never showed up in the model. It showed up in the field, after the money was gone.

I think about that story constantly.

The thing that carries you through it is having someone on your team who has actually done the work. We paused our own buying for six months to make sure we had that, and I want to walk through everything it protects you from.

Start with what you are buying.

On paper a roller is a number with a dollar value beside it. In the yard it is either a machine that lays a clean mat or one that breaks down every afternoon and quietly drains your cash.

I cannot tell those two apart by looking, and neither can my partner Chris. We both came up in finance. Jeff can. Jeff has been paving since 1995 and built Nationwide, the operating company we partnered with to do this. He walks a yard and within minutes he knows what is solid and what got cleaned up for the sale.

So we bring our own mechanic to diligence now. We stopped trusting an appraisal with a name on it we have never heard of. That one habit is the only reason we are not the guy who wired the money and inherited the junk.

The next thing expertise buys you is the money the last owner left sitting in the business.

You will not see it in the financials, because on the financials it just looks like the company is running a little thin. You see it by understanding how the work gets priced and done.

When we bought Cornerstone in Texas the margins were lower than they should have been. I could see that much in the numbers. I could not tell you why. Jeff found it in about a day.

They were doing six million dollars a year in concrete work and subbing every bit of it out at zero markup, because that was how the old owners had always won the paving attached to it. Jeff put twenty percent on it and nobody pushed back. One of the original owners said he wished he had done it years ago.

Same story with traffic control. They were paying an outside crew around fifty-five hundred a day across four or five sites for work we already handle in house everywhere else. We pulled it in and the cost dropped to about twenty-four hundred a day.

None of that was hidden. It was sitting in plain view for anyone who had run these jobs before.

The biggest risk in buying a small company is that you are really buying one person's judgment, and that person can quit.

A private equity shop almost forces them to. They put the numbers on the table and make it obvious they do not care who stays.

But the seller has guys who have been with him twenty and thirty years. He knows their kids. He has to run into these people at the grocery store on Saturday. So he either refuses to sell or he mentally checks out the day the wire clears, and the knowledge you actually paid for walks out behind him.

Jeff sells the opposite, because he is one of them. When he sits across from a seller, the guy can tell in five minutes that Jeff respects what he built. We take the back office these owners always hated off their hands, the billing and the insurance headaches, and we tell them to keep doing the part they love out on the job.

David at Cornerstone is seventy-two. The first thing he told Jeff was that he was out in six months. Last week he said he talked it over with his wife and he is staying until he is eighty. He is doing about a third of what he used to and having more fun than he has had in years.

The guy we were most afraid of losing still shows up every day.

Say you clear all of that. You buy well, you keep the people, you fix the obvious leaks.

Then you decide to grow, and a completely new set of things starts to break.

Chris repeats a line that took me a while to really hear. Growth equals risk.

The team that took a company from one million to ten is not automatically the team that takes it to twenty. The process that held up at two million a month will not hold at five.

When you push, you upend how people work and how they feel about being there, and if you do not bring them with you, you can lose ten to fifteen percent of your people at the exact moment you need them most.

The fix is simple and almost everyone skips it. You tell people where the company is going and why.

At Nationwide the operations team got up in front of the whole crew and laid out the plan to double the division's revenue in one month. We bought everyone Chick-fil-A and walked them through it.

By the end the rake man could see a path to running equipment. The operator could see himself as a foreman. People stopped guessing about what was happening above them and started asking how they get there.

Then there is the duct tape.

Every small operation is held together by a few informal habits that work fine until the day they don't. Cornerstone ran quality control by having the ops manager and the project managers FaceTime crews to eyeball the work.

That is fine at four or five jobs a day. At twenty-five jobs a day, half of them running at two in the morning to finish a parking lot before the store opens, there is no FaceTiming your way through it.

The job costing was the same kind of thing. The old system could not cleanly tell us what one crew on one job actually cost us, which is exactly how margin leaks out while everyone swears the company is healthy.

We spent three months finding what would break before we leaned on it, rebuilt those pieces, and ran them in practice before the real push.

The version of this that scares me most is what Chris calls founder magic.

A guy who has bid twenty thousand jobs can glance at a parking lot and call it a thirty percent margin, and he is usually right within a point or two. Ask him how he got there and he goes quiet. He cannot teach it to anyone.

He is a great estimator. The problem is he is the only one who can do it.

So we pulled what was in his head into data and built it into software, and now someone without twenty-five years of instinct can put out a bid that is fast and consistent. Then we track every job against the estimate and adjust when we are off.

How you grow is its own trap. Buying is fast, and you inherit every problem you did not create along with people who never chose you. Building from scratch is slower and far less predictable.

We opened up Phoenix and the playbook that works in thirty other states just did not land the same. It took a couple of months to figure that market out.

Nothing here is copy and paste, and assuming it is will leave a yard full of expensive equipment and a payroll with nothing to do.

This is why we stopped buying for six months and put the time into people and systems first.

The model was always the easy part. Whether a roll-up turns into a real company gets decided after the money leaves the account. It happens out on the job and in the operations, by people who knew the work long before we did.

If you are looking at buying into an industry you do not know cold, that is the seat you fill before anything else.

— Sam Silverman
Silverman Capital

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Some of the worst financial advice I've ever gotten came from men over 50.

They meant well. That's the thing. But a lot of what older guys hand down to men in their twenties and thirties was solid in 1985 and stopped being true today. The one I heard most went like this.

I've heard some version of that my whole adult life. It might be the most repeated money advice in the country. And for where I sit right now, it's just wrong.

I left my corporate job in September 2022 to build companies. Since then I think about money differently than I used to. So let me walk you through why I rent, and why I plan to keep renting for a long time.

I can leave whenever I want

Start with the thing nobody bothers to price. Flexibility.

If I want to move next year, I give 60 days notice and I'm gone. I don't have to list the place, stage it, or sit through months of showings hoping the right buyer turns up before the market turns.

My whole life right now runs on being able to move when I need to. A new deal pulls me somewhere, I go. Renting keeps me light. The day I sign a mortgage, I'm anchored to one zip code and a decision I made years earlier.

Rent is cheaper. Every single month.

Here's the part people get backwards. They assume renting is the expensive option.

And I'm not talking about the starter place you grab for a couple of years. Picture the house you'd actually want to own. The one in the good neighborhood with the schools and the big trees, the home you'd still be happy in ten years from now. Call it $2M.

Twenty percent down is $400k in cash on day one. Finance the other $1.6M at today's rate, around 6.6%. Add property taxes near $25k a year (way more in Florida - for now), insurance at $5k, maintenance running another $12k or so.

All in, owning that house lands around $13,500 a month.

Renting the same house? Closer to $8,000.

I'd pay roughly $5,500 more every month to own it. That's $66k a year. And that's before the $400k I had to wire over just to get the keys.

Here's what most people don't see. That gap gets wider the nicer the home gets. In the expensive areas, the ones you'd actually want to raise a family in, rents stay low relative to what the houses cost to buy (yes, inventory in those areas can be hit or miss for rentals.) The price-to-rent ratio sits firmly in the renter's favor. A $2M home almost never rents for anything close to what it costs to own one. And that's exactly the kind of house most of the people reading this are eyeing.

Now flip it. Buy a modest house in a cheaper market and the gap tightens up fast. Owning and renting end up costing about the same month to month. That's where buying earns its keep, because the mortgage forces you to save without ever deciding to. Every payment knocks down the balance whether you felt like saving that month or not, and for a lot of people that's the only reason they ever build any net worth at all.

That's a real benefit and I won't pretend it isn't. It's just not the math I'm running, and probably not yours either if you're this far down the page.

That $400k could be working

Which brings me to the part that actually keeps me renting. The opportunity cost.

The day I wire that down payment, it's frozen. I can't touch it. I can't move it when something good shows up. And something good always shows up. I run an investment firm. Right now I'm buying paving companies with a partner. Every dollar I keep liquid is a dollar I can put into a deal that pays me back.

$400k sitting in drywall earns me nothing while I live there. That same $400k compounding at even 10% turns into real money fast. That gap is the whole reason I rent.

Now run it out ten years

This is where it gets fun. Play both versions forward a decade.

I put $400k down and pay around $13,500 a month to own. The renter pays $8,000 and invests everything left over. That's the $400k that never got locked up, plus the $5,500 a month they're not handing to the bank. We spend the exact same amount out of pocket. The only thing that changes is where the money lands.

Say it compounds at 10%, roughly what the S&P has averaged for decades.

After ten years the renter is sitting on about $2.1M, all of it liquid. The owner has maybe $1.4M in equity, and that's assuming the house appreciated the whole way, and it's locked up tight. Pulling it out means selling the place and paying to do it all over again somewhere else.

Same money in. The renter comes out around $700k ahead, and every dollar of it can move.

Now here's the part that gets me. That $2.1M is enough to walk up and buy the $2M house in cash. The one in the good neighborhood. The one I actually wanted the whole time. Paid for, with money left over.

That's the whole play. Rent now, invest the spread, and a decade in you buy the house you actually want outright, on your terms, when you're ready.

And selling costs a fortune

Now say I buy anyway. A few years in, something changes and I have to sell.

Realtor commission, closing costs, transfer taxes. On a $2M home that's easily $120k to $160k, gone at the closing table. I'd need serious appreciation just to climb back to even after everything I already paid month to month.

Unless you're planting roots for ten years or more, the math rarely gets the time it needs to work. And appreciation isn't a sure thing anymore. Texas and Florida have already turned into buyer's markets.

Here's where it gets complicated

Everything I just told you is true. Renting is cheaper and it keeps my money free to move. By the numbers it isn't close.

And I'm still going to buy a house one day.

A home was never really a math problem. There's something a spreadsheet can't hold about a place that's actually yours. Where your kids grow up. Where the door is the color you picked and nobody can tell you to leave.

I'll go further than that. Someday I want a house that's paid off all the way. No mortgage. Nobody to pay.

Every principle I just laid out says that's a bad use of money. A paid-off house is a couple million dollars sitting idle, earning nothing, when it could be out working. I know that better than almost anyone. I've built a career on knowing that.

And I still want it.

There's a peace in owning your roof outright that no rate of return really touches. The business can go sideways and the market can drop, and the house still stands and it's still yours. I've watched what that security does for people. It's worth a lot.

So that's the honest version. I rent because it's the smart move, and it'll stay the smart move for a long time. Then somewhere down the road I'll buy, I'll pay it off, and I'll do it with my eyes wide open, knowing every number on the page says don't.

Now I want yours. Hit reply and tell me the worst money advice anyone ever handed you. I'll go first.

— Sam Silverman
Silverman Capital

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