Our new business (the current one) was in a totally different industry ... and to a bank, that made our income brand new. It didn’t matter what was in the account. We needed two years of tax returns from the new business before anyone would lend to us.

So we waited. We filed the second return the minute we could, in early February 2020. We closed and moved in on Friday, March 13th ... the same week the world shut down.

We made it by the skin of our teeth. What stuck with me wasn’t the timing, though. We were ready long before the bank said we were. The bank decided when.

Those same rules decide whether you can borrow against a house you already own.

Subscribe now

I think about that every time a client tells me their plan is to pay off their mortgage.

I get it. A paid-off house feels like the safest thing you can own. There’s no payment and no landlord. It feels like nobody can take it from you. For a lot of people, that feeling is worth more than any spreadsheet, and I’m not going to argue with it using interest rate math. You’ve heard that argument already.

The trouble shows up later, on the day you need the money back.

My mortgage lender has become a good friend of mine, and we talk regularly. This past spring, he put it in a way I haven’t been able to shake. Home equity works a lot like a retirement account. The money is yours, but there are rules for getting it out, and someone else enforces them.

To get it out, you apply. A home equity line or a cash-out refinance means proving your income, passing a credit check, getting an appraisal, and waiting on an underwriter to say yes. It’s all on their rate, their timeline, and their definition of “qualified.”

And the times you most need the money are the times you’re least likely to qualify. I think of a business owner in a down year, someone between jobs, a real estate investor with two rentals sitting empty, or somebody who just switched industries ... ask me how I know.

Banks tighten up right when everyone else is stressed. About a month after we moved into that house, in April 2020, Chase and then Wells Fargo stopped taking new home equity applications altogether. Plenty of people had equity on paper. They just couldn’t reach it.

It costs more right now, too. The average home equity line of credit is over 7%, and this month the average 30-year mortgage hit its highest level since late 2023. Borrowing against the house costs the most right when a lot of people would need to.

If you invest in real estate, you already know this feeling. You can have a lot of equity spread across properties and still be short on cash you can actually use this week.

This is a big reason why I believe your safety cushion should live somewhere nobody can tell you no.

I have my own bias here. Brandon and I help people build one of those places: cash value in a whole life insurance policy designed for it. When a client wants money from theirs, they complete a simple form and the money is sent their way. There’s no credit check and no proof of income. They decide when and how much, and they decide how to pay it back.

When we did buy that home, I got a bunch of offers in the mail to buy “mortgage protection insurance.” What I love about storing my extra cash in a policy is that there’s a death benefit that could pay off my mortgage if something happens to me, plus I can use the cash value for whatever I want, whenever I want. No high-yield savings account or T-bill does both of those things.

It isn’t free money. A policy loan charges interest, and until it’s repaid, the balance comes out of the death benefit. It only works if the policy was set up for it and has had time to build value. Plus, it’s a reserve that sits alongside your investments ... not a replacement for them, and not an investment itself.

The rate works differently, though. A HELOC’s rate moves whenever the prime rate does, and the bank can freeze or cut your line. A policy loan rate is either fixed or can change only once a year, on the policy anniversary. The decision to use your money is yours. There’s no underwriter making the choice for you.

That’s what liquidity before growth means to me. Pay down the house if that’s your peace. Just don’t let the house be the only place your cushion lives, because a house can’t hand you money … only a lender can, and they will always qualify you first.

If you needed $50,000 next month, whose permission would you need to get it?

It was Marcia. I’ve never admitted that out loud until now. (To that classmate, whoever you are ... you were right.)

That was TV trivia with nothing riding on it, and it still took me about thirty years. Admitting you were wrong about money is harder. Noticing what you’ve never lived through is harder still, because nobody’s standing there to point out Marcia.

I graduated from college in 2006. By 2008, I was working for a national nonprofit, watching students a couple of years behind me graduate into a job market that didn’t want them. In 2009, I left my full-time job. I was already planning my way out into entrepreneurship, and leaving meant someone else on the team wouldn’t have to be laid off.

It turned out to be a good time for us. So many people around us were figuring out how to adult on the cheap. We were young, had no kids to support, and were happy to live with roommates on plenty of ramen.

I watched the Great Financial Crisis through the lens of the job market. We owned very little in investments back then. My older colleagues watched it from their retirement statements, and they joked that their 401(k)s had turned into 201(k)s. A lot of people weren’t watching the market at all yet ... and by that measure, I’m mostly writing about myself here too.

If your first real paycheck came after 2009, or your first real investment did, your picture of a “normal” market was built during one of the most unusual stretches in market history.

That second group is bigger than most people think. Only about 6 in 10 Americans own any stock at all, even counting retirement accounts. Plenty of business owners pour everything into the business for years before they ever open an investment account. Age doesn’t tell you what someone has lived through as an investor. Their start date does.

So, for those of us who started with real investments after 2009: I’m with you, and this one’s for us. The people who came before us already paid for these lessons. We get to learn them cheaper.

We’ve seen real drops. In early 2020, the S&P 500 fell about a third in roughly a month, then hit a new high by August. In 2022 it fell about a quarter, and stocks and bonds went down together, which is rare. That one took about two years to fully recover.

Both times, the people who held on came out fine. So the lesson a whole generation of investors learned, whatever their age, is that drops are short and patience pays.

So far, so good.

What you haven’t lived through is the long one.

If you put a lump sum into the S&P 500 at the start of 2000, you had less at the end of 2009 than you started with ... even counting dividends. A full decade of patience, and the market gave you nothing for it. The index didn’t climb back above its 2000 peak and stay there until 2013.

And 2000 wasn’t the only long one. The Dow peaked in 1929 and didn’t get back to that level until 1954. It first flirted with 1,000 in 1966 and didn’t stay above it until 1982. Three long stretches in less than a hundred years, flat on paper and worse after inflation, is a pattern.

“It always comes back” has been true for the broad US stock market in every downturn so far. “So far” is doing a lot of work in that sentence. Markets that looked permanent have stayed down for a generation ... Japan’s stock market peaked in 1989 and didn’t get back there until 2024.

Even when the index comes back, not everything in it does. You might have heard of Lehman Brothers, but there was also General Motors. Shareholders in both were wiped out in 2008 and 2009 while the S&P 500 recovered around them. The average experience isn’t everyone’s experience.

And “back” can take a while. Thirteen years is a long time to wait if you need some of that money in the middle ... for a slow season in your business, a roof, a kid’s tuition, or your own retirement date.

Nobody knows when the next long one shows up. It could land in your 40s or your 70s, or both. What matters most is which direction your money is moving when it does.

A simple example, with made-up numbers. Two people each start with $100,000. The market goes up 25% one year and down 20% the next, or the reverse. Those two years cancel out. On its own, the order doesn’t matter: both end up right back at $100,000. (They also lost two years of potential growth and probably paid some fees along the way, but let’s keep this simple.)

Now have each of them take out $10,000 after the first year. You’d expect both to end at $90,000. If the good year comes first, they end with $92,000. If the bad year comes first, they end with $87,500. Same returns, same withdrawal, $4,500 apart.

Flip it and have them add $10,000 instead. You’d expect $110,000. Now the bad year first comes out ahead, $112,500 to $108,000, because the new money went in cheap.

That’s the whole idea of sequence of returns. A long flat stretch can work in your favor while you’re still adding money and won’t need it for decades. It hurts when you have to sell in the middle of one.

The flip side is true too. A long climb feels great while you’re adding money, but every new dollar buys a little less. It’s a gift when you’re the one selling.

You don’t get to pick which stretch lines up with which decade of your life. No one can predict it for you either. But that doesn’t mean you’re stuck at the market’s mercy. What you can build is a plan that holds up whichever decade you get.

Because the market is always doing something unexpected. The examples so far have been about stocks. This year added a twist that’s easy to miss. The calm part of the portfolio just had a rough quarter. Morningstar reported that the US core bond index lost 3.4% from July through September, its worst quarter since 2022, as the 10-year Treasury yield climbed to its highest level in about two decades.

That doesn’t make bonds bad. They pay more now than they have in years. It means even the steady part can have a bad stretch, and if you started investing after 2009, you’ve mostly known bonds as the part that doesn’t move.

Most of the people I talk to who started after 2009 aren’t bad with money. They’ve been tested on how far it can fall, just not on how long it can stay there. That’s a gap in experience, and experience is fixable.

A mentor of mine who’s been in this business for decades told me something on a drive a few weeks ago that stuck with me. I’d asked him why some people lean in when they hear how we think about money, and others shut down.

“Look, Amanda,” he said. “No one wants to face reality.”

He first heard about our shared financial philosophy in his 50s, and he was angry. Angry at himself, for every car he’d paid cash for and every decision he’d made without knowing there was another way. He had to admit he’d been wrong before he could actually hear it.

I heard about it at 29. I was angry too ... but at everyone else, for never telling me. Getting to blame other people made the change easier for me.

Now take the Marcia problem and put real money on it ... a decision you made with your retirement savings however long ago.

That’s the real gap between someone who invested through 2000 and someone who started after 2009. The first has to admit to a decision they’ve lived with for decades. The second hasn’t been forced to face reality yet, and can be mad at the world for telling them the oldest sister is Jan instead of Marcia. What they choose to do next matters more than how old they are.

“So far, so good” is the most expensive sentence in financial planning. It’s true every single day ... right up until the day it isn’t.

None of this means you should sell everything, stop investing, or sit on the sidelines waiting for prices to drop. What it does mean is that your plan should be able to wait out a long stretch without forcing you to sell at the bottom to pay for real life.

A few questions to test yours against the long one:

• If the market went nowhere for ten years, which of your goals would still happen on time?

• Could you go five years without selling an investment at a loss to cover real life?

• If your business had a slow year at the same time the market did, where would the money come from?

• When you say “it always comes back,” are you talking about the whole market ... or the specific things you own?

If any of those made your stomach tighten, that’s worth knowing now, while it’s still so far, so good.

For a lot of people, the answer starts with money they can reach without selling anything, and for most of us, that starts with plain cash. For Brandon and me, part of it has also been the cash value in our whole life policies, which we’ve built since 2013 alongside our investments, not instead of them. It’s not the right tool for everyone, and it’s not an investment. I have my own bias here, too, since helping people set up policies like these is one of the hats I wear. That’s one more reason to run your plan past more than one voice before you change anything.

What year did you start investing, and what’s the longest bad stretch you’ve actually lived through? Hit reply. I read every one.

P.S. If your business is profitable and the cash is piling up while you wait for the “right time” to do something with it, that’s what this Thursday’s free workshop is about. You fixed cash flow. Now what? is Thursday, October 29, at noon Eastern. Save your seat.

Save Your Seat

I opened with a question. How many of you have been to a rally, an interest meeting, or a panel hosted by a nonprofit? Most of the hands went up.

Then I told them what I’d noticed at almost every one of those gatherings. The people were passionate about their cause ... and the coffee was terrible. Folgers in a percolator, Styrofoam cups, fake creamer, and coffee grown by farmers living in extreme poverty, poured by people working hard to make the world better.

It bothered me. How could people who cared that much about doing good in one area miss the harm they were doing in another?

What I didn’t tell that class is that Brandon and I had spent years doing the same thing to ourselves.

Subscribe now

Our first business, Overflow Coffee Bar, was named for something I call the Overflow Principle, and the picture behind it was a fountain.

At the top sit you and the people closest to you. When good things happen there, they spill into your neighborhood and your workplace, then your city, and outward from there. My favorite part of a fountain is the feedback loop ... the water that reaches the bottom cycles back up to the top.

We built the whole business around that idea. Overflow was an L3C, a low-profit company set up so the profits would spill into the community. Our slogan was “Changing the world one cup at a time.”

We paid close attention to every tier of that fountain except the top one.

In that same talk, I named the three things I’d watched burn out good people doing social change work: loneliness, compassion fatigue, and competition between organizations that should have been partners. I told the class Brandon and I had almost quit more times than we could count on our fingers and toes.

All true. What I left off the list was money.

That’s the mission trap. When your business exists to do good, paying yourself starts to feel like taking something from the cause. So you don’t. You serve yourself the bad coffee and call it commitment.

I’ve written before about the day our attorney asked how much we were paying ourselves, and the answer we didn’t want to say out loud. That story is here. It stung first. What we did with the sting mattered more. We could have closed up, gone back to our cubicles and said, “At least we gave it a try.” We were too stubborn for that, like most mission-driven people I know. And the question landed because we’d already started to change.

Confidence compounded, one layer at a time.

In 2013, we started our first Bank On Yourself type policies. For the first time, we had money we could actually reach when the coffee shop had a bad month ... and a coffee shop has plenty of bad months.

A year later came Profit First. Profit stopped being whatever happened to be left at the end of the month and started getting set aside first.

By the time our attorney asked his question in November 2015, we had the systems. What we didn’t have yet was permission to take care of ourselves, and his question gave us that.

Liquidity + profit + permission = a fountain that could finally fill from the top.

In March 2016, about 200 people came to celebrate Overflow’s fifth birthday. I told our story that night, including the parts we’d almost quit over. Afterward, person after person came up to say how much it meant to them. A few told me I should run for public office. (No thank you.)

My story that night grew out of those three years, 2013 to 2016, and for the first time I wasn’t telling it as a cautionary tale.

That night was proof something had changed, and not only in the business.

Even after we set up Bank On Yourself and Profit First, I still had dark stretches in 2015. Some were dark enough that I had thoughts of self-harm. By that March, they were gone, and they haven’t come back. I can’t prove what changed it, and I won’t pretend a financial system cures depression. If you’re in a dark place, please reach out to someone. In the US, you can call or text 988 any time.

What I know is what shifted in me. Doing what brings me joy had always included doing good for other people. It finally included doing good for myself.

I still work 50-plus hours most weeks on a mission I believe in. Most days I end the day content with myself and what I did ... tired sometimes, but not running dry.

The numbers moved too. From 2013 to 2023, our net worth grew tenfold, and so did our income. The income on our 2013 tax return is the same amount we gave away in 2023.

A lot changed in that decade, including the business itself, and I can’t untangle every cause from every coincidence. Your path won’t look like mine. What I do know is that taking care of myself first is what made the rest possible.

Mission without margin isn’t sustainable. I believe that more now than I did at Overflow.

The permission turned out to include permission to change. If you’d told me in 2011, the year we opened, where I’d be now, I wouldn’t have believed you. We sold Overflow in 2018. The mission didn’t end there. I’m willing to do anything short of breaking the law or my ethics to keep it going, even if that means changing everything else.

If you’ve built a business to do good, one of the most generous things you can do for the mission is take care of the person running it. A fountain overflows from the top. An empty top tier doesn’t reach the neighbors, the city, or the farmers.

What would your mission look like if it finally paid you? Hit reply or leave a comment. I read every one.

Leave a comment

P.S. Once your business is profitable, the profit needs somewhere to live. That’s what this month’s free workshop is about. You fixed cash flow. Now what? is Thursday, October 29, at noon Eastern. Save your seat.

The workshop is the first thing on the new livecounterflow.com, which is now live. Everything I teach here has a home there now, starting with the Start Here page.

I typed that into ChatGPT. I was preparing for a presentation to real estate agents and I’d asked whether investing $2,000 a month for 15 years at a 10% return would let a hypothetical agent retire on $8,000 a month. Its first answer was careful. It ran the numbers, told me they’d end up with about $829,000, and warned me that 10% was optimistic. It also pointed out that $8,000 a month in today’s dollars would be closer to $12,000 a month in 15 years, which pushed the savings target to around $3.5 million.

So I pushed back, the way plenty of people would.

“Absolutely,” it said. “If 10% is the planning assumption, we can hold that constant rather than debating it.”

Then it re-ran the plan ... and inflation was gone. The target dropped back to $2.4 million. I’d argued with one assumption, and it quietly let go of two.

I want to be fair here, because I use AI every day in my business and this isn’t an anti-AI piece. For this presentation, I ran three money questions through ChatGPT, posing as a real estate agent with commission income, and checked every number it gave me. The math was right every time. It knew the 2026 contribution limits for retirement plan options and the pro-rata rule for backdoor Roth contributions, which plenty of people in my own industry get wrong. When I asked what to do with a $42,000 commission check, it told me to set aside taxes first and keep a bigger cash cushion than a salaried person would need, because commission income shows up in chunks. That’s good feedback.

Something else took me a minute to notice, because each answer was mostly right on its own.

In the first conversation, ChatGPT told my real estate agent that liquidity matters more with variable income than it does with a steady paycheck. In the second, I told it the same agent made $80,000 last year and $150,000 this year, and asked which retirement account to use. It recommended a Solo 401(k) and showed how to put up to about $52,500 into it ... money that generally can’t come back out before 59½ without a penalty.

Those two answers can’t both be the whole plan for the same person. Each was correct about the question in front of it, and neither knew the other existed. It never asked whether the agent had disability coverage, who depended on that income, or what a two-year slump in home sales would do to the plan. I didn’t ask, so it didn’t either.

Back to the retirement question. I told it to use 10%, so I’ll let the “Absolutely” slide. Many advisors would do the same and meet the client at their own assumption for running the projection. What bothers me is what happened next. Assumptions can make or break a financial plan, and dropping inflation quietly took $1.1 million off the target. I never asked it to do that. A big part of being Counterflow is challenging the status quo or average assumptions when the situation at hand is anything but. ChatGPT changing one without saying a word is a big red flag.

A tool built to be helpful drifts toward agreeable in a conversation. Show up with a number you’ve already decided on, and it’ll build the plan around your number.

So I tested it with my own industry. In one fresh chat, I said I was convinced whole life insurance was a scam and asked for help explaining why to my spouse. In another, I said I was convinced whole life was the best place to keep my savings, and asked for the same help.

It talked me down a notch both times. It told the first version of me not to call whole life a scam, and warned the second not to put all my savings in it. Then it helped me win the argument anyway. Both chats ended with a ready-made speech for my spouse, making my case.

The two weren’t quite even, though. The anti–whole life version of me heard “Your argument has a strong financial foundation” in the very first sentence, followed by a calculation showing $561,187 on the investing side and no number at all for the policy. The pro–whole life version got its caveats woven into every point. Same question, flipped ... and it leaned toward the answer most people already believe. I don’t read that as an agenda. It’s built to be agreeable, and the most agreeable answer is usually the one most people already hold.

I recognize this relationship, because I had one just like it long before AI existed.

When Brandon and I were newlyweds, I had a giant Suze Orman book, highlighted cover to cover. Any time we had a money decision to make, I flipped to my highlights and did what it said. I took the 403(b) match at work before we’d paid off our debt because of how I read one chapter. That book was my original ChatGPT ... a confident answer to whatever question I brought it.

Our friend Mark spent at least a year trying to tell us about a different way to think about money. I kept going back to the book. By July 2013, we were doing everything right on paper. Our bills were paid on time. Our debts were slowly getting paid. And we had zero peace of mind. The conventional thinking didn’t match how we actually lived or ran our coffee shop, and the book had no way of knowing that.

That July we hosted a documentary night at the shop, and Mark picked the film. The conversation afterward is what finally got through to us. We officially started our non-Suze’s-book-led path on December 1, 2013.

Over the 13 years since, the bigger change has been my confidence. I still learn from books, from mentors, and yes, from AI. But I trust my own judgment now, and I can tell what’s right for us specifically.

Our café flooded in 2017. A freak storm hit while the roof was off for repairs, and the calls started coming in while we were at the gym. It was one of the most stressful times of my life, and it turned out I was pregnant and didn’t even know it yet. This year our basement flooded with five feet of water. We lost the furnace and a car, and we can’t get flood insurance (I’ve asked multiple times). The second flood was much bigger and much costlier... and I handled it like a speed bump instead of an obstacle. The one who noticed my calm the most was our 8-year-old, who was in my tummy during the first flood.

The book never asked about my life. The chatbot did ask me questions, to its credit ... after it had already handed me the answer and the speech for my spouse. A good advisor asks first.

Keep asking AI about money. It runs the math faster than I can, and most of the time it gets the math right. Just know what you’re getting: a very good answer to the exact question you typed, from something that will soften your wording and then help you win the argument anyway.

The questions that change a plan are usually the ones you didn’t know to ask yet. My hypothetical agent asked where to put a $42,000 check. Nobody asked what happens at home if the checks stop for six months, and that’s the question I’d want answered first. A chat box can only answer what you think to type into it. Helping someone find the question they weren’t asking yet is where a person still earns a place in the conversation.

Back in June, I wrote about the unasked question (episode 8). Unless you build a bot that acts on its own, AI won’t reach out and prompt you. Most financial advisors don’t reach out first either. That post is about finding the question you wouldn’t think to ask.

People have biases too, me included. That’s why we recommend a Money Team. Several inputs, especially ones that contradict each other, are the best defense against anyone’s bias. The best teams use AI and people together. And the most proactive thing you can do with either one is ask for the other side of the coin. That’s all my whole life test was: the same question, argued in reverse, in a fresh chat.

Every answer it gave me was about one piece. Nobody was looking at how the pieces fit together ... and that’s the part that decides whether a plan holds when life doesn’t follow the spreadsheet. Human judgment is still required.

Have you asked AI about your money? I’d like to know whether it ever told you something you didn’t want to hear ... or whether it agreed with you, too.

Leave a comment

P.S. Brandon and I have been working on something new, and you’ll see it first in next Saturday's post. If someone forwarded this to you, subscribe so it lands in your inbox.

Subscribe now

A note on the screenshots: I used ChatGPT as the example because it’s the tool most people reach for, not as an endorsement. ChatGPT carries its own warning that it can make mistakes. I checked the numbers I quote here, but I may not have caught every error in the screenshots.

A few weeks ago, a dad on Reddit was living a version of that question. He had about $4 million and around $70,000 a year coming in whether he worked or not, and he was asking strangers whether he could finally stop working. His spreadsheet said yes, but his gut kept telling him to keep going, and maybe his gut was doing math the spreadsheet couldn’t.

The best reply in the whole thread told him he didn’t have a money problem... he had a feeling-of-safety problem.

Now, I don’t know more than what I just shared about this dad. He’s a stranger on the internet. But I do have experiential knowledge of what’s likely going on. Four million dollars didn’t quiet his soul, and I don’t think I’m going out on a limb to say a larger account won’t quiet it for him... or for you either.

And it’s the part the financial industry keeps missing. The fix it sells is always a better product: pick a better fund, find a better rate, add one more account, app, or spreadsheet, and eventually the anxiety is supposed to settle down.

I know people with two years of emergency funds who still feel anxious, because the product or the balance was never the issue. Products and balances sit on top of a structure. If nobody built the structure, it doesn’t matter how good the product is... You still feel uneasy that everything could topple over at any minute.

A woman I coach sent me a line this summer that I haven’t been able to shake. She’d heard a famous preacher say it: “Many people pray to be a better slave instead of praying for freedom.”

She wasn’t talking about money when she sent it, but I couldn’t stop thinking about money. She had no idea I’d been chewing on this idea of becoming a “better slave” for about two years.

Most of the financial advice most people have ever gotten is a prayer to be a better slave. Budget more carefully, diversify more wisely, get better at the thing you’re already doing... inside a structure nobody ever asked you to question. The conditions improve while the arrangement stays exactly where it was.

One question tells you which one you’re living in: if we had another Great Depression or Great Financial Crisis, with mass layoffs, a 50% decline in the stock market, and a decade of recovery, would your financial products and balances stay standing or crumble?

For most people, most things would fall apart. The mortgage doesn’t care that you got laid off, and the market isn’t going to pause because you need to buy groceries. You’ve built a life that runs on one uninterrupted signal... and mistaken the signal for security.

So far, so good... until it isn’t.

“Architecture over products” is our whole disagreement with the rest of this industry, in 3 words. When the architecture is there, money stops running the show.

If you take that approach, you won’t necessarily have more money, and you might not even feel better about it at first. What changes is who makes the decisions. Money used to, and now you do... the slower job you actually want, the client you finally turn down, two weeks off without checking your phone once. None of it breaks anything, because you built it so it wouldn’t.

People are usually surprised when I tell them, “I’m a financial professional, but I don’t really care about money.” I grew up poor. My parents were on public assistance when I was born. When I filled out the FAFSA for college, I discovered they made less than tuition, room, and board for the school I went to. It would be easy for me to make money the center of everything, vowing to amass enough to break generational poverty. I’ve chosen a different path. I want money to never run my life. I want to wake up each morning and decide what I do that day because I care about people and making a difference in their lives, not because I’m trying to build my balances. Financially, I’ve built a structure that runs in the background to increase my net worth every single year so far, through ups and downs in the revenue of my business, the stock market, interest rates, and inflation. It hasn’t always been easy, but it’s been a life worth living, and it keeps getting stronger the longer I stay on this path.

A few years ago, it dawned on me that I’ve lived my own definition of a financially independent life for a while. I didn’t have a $4 million nest egg or $70,000 in passive income. Far from it. I simply decided I’m independent of money, and it can’t run the show of my life. I didn’t wish for a better form of slavery but true freedom. It wasn’t until later that I found the architecture to help me make this decision a reality, and that’s when the anxiety went away, and I had true control.

That’s the marker I watch for, and debt-free isn’t it... Plenty of debt-free people are still run by their money, just in a different way. The marker is whether money still sits in the control seat for your decisions, or whether you’ve moved into it. The dad on Reddit had the number, but money was still sitting in the driver’s seat.

Most people have never been asked to imagine that. We ask what they want to buy and what number they’re aiming for, and we rarely ask what they want to be free from or free to do.

So I’m asking you: what decision have you been making because money told you to... that you’d make differently if the Benjamins didn’t get a vote?

Sit with that one before you answer it. It’s usually not the decision you think it is.

Subscribe now

Two different leaders, two different rooms, months apart. Both said almost the exact same sentence. I found out later they’d talked about me in between ... the first had used that exact phrase with the other, who then repeated it to me verbatim.

The decade that followed wasn’t dramatic. There wasn’t a single bad day I could point back to and blame. It was quieter than that: a habit of taking up less space than I actually had, especially in rooms with older men. I didn’t argue or fight. I just got quiet, and I stayed that way for most of my twenties.

On my 30th birthday, I made a decision instead of waiting for another event to force one. I was old enough now that people had to listen to me, so it was time to go find my voice again. Between 30 and 40, I did. It’s in the record if you go looking ... I started podcasting under a different name in my thirties, then another, before Counterflow existed at all. By the time I built this one at age 41, I wasn’t the same person who first sat down at a microphone.

Nice vs. Kind gets talked about here as a professional framework: how to run a financial practice, how to talk to a client, how to give a team honest feedback instead of smoothing everything over. What’s never been said out loud before is where it actually started. The personal version was “trusting my own voice.” The professional version is “say the plain thing and let it stand.” It’s the same concept, carried between 2 parts of life. Nice kept me quiet for a decade. Kind is what I built once I stopped.

I learned early in this work that trust breaks fast and rarely comes back once it does. There are only two ways to build it: tell someone what they want to hear, or tell them the truth when it’s hard. When a client or a prospective client asks me a real question, I don’t get to go quiet. I have to answer.

Integrity’s been non-negotiable for me since I was a kid ... I made my own parents start recycling in elementary school after a documentary about the Amazon rainforest scared me straight. So when I’m forced to speak, I tell the truth. I’ll wrap it in a spoonful of sugar to make it easier to hear, but I won’t shrink from it, not when I’m asked directly. The professional version of me can’t hide. The personal version could, for a decade.

None of this is a case for saying every thought that crosses your mind. Plenty of people are already overconfident in their own voice and no better for it. If you’re worried this is about you ... talking too much, taking up too much space ... it probably isn’t. This is something narrower: trusting your voice enough to say what actually matters, in love and with care, instead of staying quiet because quiet is easier.

Money runs on the same muscle. It’s one of the last real taboos left ... people won’t bring it up with their own family, let alone a stranger on the internet. Trusting yourself enough to talk about money out loud and trusting your own voice are the same trust, aimed at two parts of life.

We get it wrong sometimes. Someone’s comment wounds us for it. My healing from that didn’t stay private, though. It’s the reason I can sit across from a client now and say the plain thing instead of managing their comfort ... and maybe the reason someone reading this can finally say theirs.

Two leaders, two parts of life, and a decade of quiet I mostly agreed to on my own. That’s the story I’ve got. I don’t know what yours is.

When did you go quiet because someone told you to take up less space ... and what would it look like to take it back?

Subscribe now

The professional version of this conversation is live too. I sat down with Mark Willis on Not Your Average Financial Podcast to take Nice vs. Kind all the way through: financial advisors, policy loans, Profit First, retirement readiness, all of it. Listen right here, or find it as Episode 473.

I’m still that kid some years. Brandon and I set genuinely lofty goals every January, revenue goals mostly, the kind with a real number attached, and most years we end up somewhere short of them. We both feel it. Brandon’s version runs darker than mine ... he’s a Gen Xer with all the jadedness and pessimism that’s stereotypical of his generation. Mine stays stubbornly optimistic. For me, even in October, there’s still time to catch up.

In a great year, neither of us feels behind. In a flat year, or a down one, we both feel very far behind.

We have what we call a meandering story. If I’d gone straight into financial services out of college, and Brandon straight out of the Marine Corps, we’d probably be twenty-plus years further along than we are right now. Instead, we spent our twenties and some of our thirties running a coffee shop and planting a church.

I don’t know that I’d skip it, given the choice again. But I’m in my forties now, and Brandon turns fifty next year, and “we should be farther along by now” is a sentence we’ve both said out loud, more than once, always measured against the version of us that started earlier.

It’s one of the most common phrases I hear, period. It comes from everywhere: clients, people who aren’t clients, and ourselves.

The question that actually does something with the feeling, for me, is: compared to what?

I’m behind this year’s goal, sure. I’m behind the version of us that went straight into this work out of college and the Marine Corps instead of a coffee shop and a church plant. But compared to my own parents at my exact age? I’m nowhere near behind. I’m ahead in ways they never got the chance to be.

I’ve started measuring success by how far someone’s come, not by where they’ve landed. What makes “farther along” sting is measuring against a finish line nobody ever drew on purpose, instead of against the place we actually started. It’s perhaps the one circumstance I allow myself to look in life’s rearview mirror.

So Brandon and I have started doing something different in September and October, instead of only staring down the number we won’t hit by December. We look back at where we stood a year ago, this same month. Almost every year, even the flat ones, we’ve moved, though not always in revenue. Sometimes it’s something else entirely.

We started our first business with a negative net worth. I know exactly how far that specific number has moved since then, in real dollars. It’s not the same as hitting this year’s goal on schedule. It’s not nothing either.

I know my own answer to “compared to what.” I’m not sure it’s yours.

Knowing the question doesn’t make the feeling go away. It’s still September. The goal you set in January is still sitting there, unmet. “Farther along” is still doing the measuring, whether you’ve ever named what it’s measuring against or not.

It’s not only a January-goal problem, either. It shows up the year you meant to finally start the business, the passive income number that was supposed to replace your paycheck, the count of rental doors you swore you’d hit by now, or the sale that should have already closed. “Farther along” shows up in all kinds of ways, in a lot of life’s Septembers ... most of them nowhere near a calendar.

Subscribe now

A reserve funded above the bare minimum isn’t only defense. It’s optionality. It’s what lets you say yes to the good phone call too ... the competitor’s business that comes up for sale, the opportunity with a Monday deadline, the thing you’d take in a heartbeat if you didn’t have to go find the money first.

The difference between “I’d need to think about financing” and “give me until Monday” is rarely the opportunity. It’s whether the cash was already sitting there, ready to move.

We closed on our house on Friday, March 13, 2020. We were moving from Illinois to Cincinnati, and I remember driving across state lines, wondering if that would even still be allowed by the time we got there. The world was starting to come apart in real time. At the closing table, Brandon sneezed mid-signature. Everyone in the room froze. “Keep your pen,” the realtor said.

We’d kept plenty of cash back when we made that purchase. We didn’t buy more house than we could afford, and we didn’t put every liquid dollar we had into the walls of it. At the time it just felt like good sense. A few days later, with the country shutting down around us, it felt like the main reason we could still breathe.

The house was a yes we’d already said, and the reserve is what let us keep standing behind it while everything else went sideways. Some businesses closed permanently in the following 12-18 months, some thrived, and we stayed roughly flat.

Business owners live the math of reserves, just with higher stakes. Unless you’ve genuinely got something novel, you’re not likely to outpace your competition on ideas alone. You’re more likely to get the edge from having cash ready when they don’t. The idea doesn’t wait for you to find financing. Neither does the seller, the lease, or the hire you know you need before your competitor gets there first.

And it’s not only a business principle. A safety net funded “for emergencies only” can’t say yes to anything else. One built with margin can ... same dollars, sitting in the same place, doing a second job the “starter emergency fund” math never accounted for.

Bucketing has a failure mode. I’ve known people to say no to a genuinely good opportunity because they didn’t want to touch their “emergency fund.” The money was sitting right there. They just couldn’t bring themselves to use it for anything but the disaster they’d mentally assigned it to.

When you only let your money do one job, you’re stuck ... even when you’re sitting on cash.

That doesn’t mean throw the buckets out. Keep something back. Don’t risk it all on one opportunity, no matter how good it looks. But the labels are a filing system, not separate wallets. It’s all one wallet, just different slots. The dollar in the “emergency” slot and the dollar in the “opportunity” slot are the same dollar. You decide what they’re needed for, when you actually need it.

That doesn’t mean every bucket should stay loose, either. If you don’t trust yourself around money yet, a hard “do not touch” line on a fund is doing real protective work, and it should stay hard until you’ve built the track record to trust yourself with something looser. What that stage actually needs is a decision made well in advance, before either kind of phone call comes in.

That’s the actual fix, and it’s not mine ... it’s Mike Michalowicz’s. He encourages actually writing down the rules for a fund (the vault account if you know Profit First - see pages 150-151 of the book) before you fund it. Not “we’ll figure it out when something comes up.” The answer needs to be real and specific: when you’ll use it, how much you’re allowed to move, decided while you’re calm and nothing is on the line. Put the decision out in front of the crisis and the opportunity both, so neither one gets to talk you into something you didn’t already agree to. The rules can loosen as you get more sophisticated with money. They just can’t start loose.

If you looked at our own YNAB categories, you won’t find one called “emergency fund.” We don’t have one. What we have is an opportunity fund ... same money, same job as everyone else’s reserve, just a different name on the slot. We didn’t rename it to be clever. We renamed it because “emergency fund” only gets exciting to fund once something’s already wrong. “Opportunity fund” gets funded consistently because we’re excited to build our financial futures.

We didn’t build our reserve because we were expecting a pandemic to break out at the same time as closing. We built it because we’d already decided our margin mattered more than maximizing what we could technically afford. The pandemic just happened to be the thing that proved it.

You won’t know in advance which kind of phone call your reserve is for. What if you built it big enough to answer both?

Subscribe now

That wasn’t a throwaway line. It was actually what we told our team, out loud, at our third anniversary staff dinner. We handed out awards, ate cake, and then Brandon said the thing we’d both been circling for weeks: we’re moving in the right direction, but we’re not where we want to be. So let’s all just focus on one thing: “Suck less tomorrow than we do today.”

The rule we landed on was this: if we added 1% to our top-line revenue every week ... maybe by upselling one extra pastry a shift ... the compound effect would grow our revenue significantly over a year. If we cut costs by 1% a month ... maybe just by measuring milk properly for the lattes ... our net profit would come out over 12% higher.

It worked. And it wasn’t just Brandon and me chasing that number. Our whole staff got pulled into it, hunting for their own little 1%s on the register or behind the counter. It turned into a game, and it gave people ideas that added up to a lot more than 1%.

The number was small on purpose. One percent isn’t impressive. Nobody puts 1% on a vision board. But it worked precisely because it wasn’t a target bolted onto a business that had no room for a bigger one yet. It was a percentage of what was actually happening, not a number we picked off a chart because it sounded ambitious.

That’s the piece that carries over to savings, especially if your income moves around ... commission, tips, a business owner’s uneven months. Save a percentage of every check you actually get, not a fixed dollar amount you picked in a good month and now have to defend in a bad one. Start at 1% if that’s what’s true right now. The number matters less than the fact that you started measuring it at all.

This is the part that surprises people. If you’re already saving 10% or already maxing out your 401(k), you might be nodding along at the person stuck at 1%, thinking you’ve got this figured out. You’re playing the exact same losing hand, just at the other end of the table.

I see this constantly in my own practice. Someone maxes out their 401(k) every single year and feels like they’ve done everything right. Then I run the actual numbers. Max out $23,500 a year for 30 years, growing at a realistic 5% after inflation, and you land around $1.5 million ... in today’s dollars, not fantasy dollars. That sounds like a lot until you ask what it has to produce. To keep the math easy, a $100,000-a-year lifestyle for a 30-year retirement needs about $2.5 million, using the common 4% rule (withdraw 4% a year and your money is supposed to outlast you) ... though retirement researcher Wade Pfau now puts the real odds of that closer to 60-70% in today’s environment, not the near-certainty it’s usually sold as. That’s a roughly million-dollar gap. And it assumes nothing goes wrong across sixty combined years ... no market crash the year before you retire, no long-term care bill, no extra decade because you made it to 95 instead of 85. Things are never that perfect for that long.

The beginner’s problem is that 1% feels too small to bother with, so a made-up “should be doing more” number sits there unclaimed. The maxed-out saver’s problem is the mirror image: the IRS contribution ceiling gets treated like a finish line nobody actually drew. Hit the max, check the box, and assume it was chosen for you because it’s the biggest number allowed. It wasn’t chosen for you. It’s just the biggest number the tax code will let you put in that particular bucket this year. Whether it’s the right number for your life is a completely separate question, and most people never ask it, because a rule of thumb answered it for them before they thought to.

Whether you’re stuck at 1% because it feels like a flat, unmovable number, or capped at the IRS max because it’s the biggest number allowed, the common human condition is the same: outsourcing your own choice and responsibility to somebody else’s number.

The percentage was never the point. Choosing it was. And choosing it again next year, and the year after, as your income changes, your business changes, your family changes ... that’s the whole game, not a chore you finish once and file away.

So which one are you: the 1% that feels too small to count, or the max you’ve never actually questioned?

Either way, the rule from that staff dinner still holds: “Suck less tomorrow than you do today.”

Subscribe now

My dad used to say something that stuck with me: “You’re gambling every time you get in a car.” You have zero control over the other drivers on the road. Somebody in another lane can end your life, and there’s nothing you can do about it beforehand. Morbid, but he’d say it every time someone complained about gambling being reckless. He also used to tell stories about playing poker and winning his way from southern Ohio up to Chicago. He once claimed he won the down payment on a house at a card table. I have no idea how much of that’s true. Small town, one card table, and a storyteller for a father will do that. But the point holds whether the stories are exact or not: his definition of gambling had nothing to do with cards. Something on the line, and no control over the outcome.

People sometimes get pushback for calling the stock market a gamble. It recovers, it goes up over time, it isn’t a coin flip where you get red or black, and it’s all or nothing. Fair enough, it isn’t that kind of bet. But my dad’s definition still applies the second you buy: you have no control over what that stock does next. At least in a car you can usually see something coming and steer around it. Harder to do with a falling market.

Everyone treats the employer match like the one piece of financial advice with no downside. Free money. Don’t leave it on the table. It’s the closest thing personal finance has to a universal rule.

The match itself isn’t the bet. Money landing in your account that wasn’t there a minute ago is about as close to a sure thing as personal finance gets. The bet starts the moment it’s in there.

A traditional 401(k) contribution isn’t a savings account. It’s a bet. Actually, it’s 4 bets, and the 4th one is what I don’t hear enough people discussing.

First, you’re deferring the tax on that money now, on the assumption that when you eventually withdraw it, your tax rate will be lower than it is today. Nobody in the enrollment meeting names it that way. The form doesn’t call it a wager. But that’s what it is, and the conventional wisdom hands it to you as a no-brainer without ever naming the trade underneath it.

There’s a second bet hiding inside “free money” that almost never gets named: you can’t touch that money until you’re 59½. I know people who’ve maxed out a 401(k) while carrying credit card debt at nearly 29% interest, because the money that could have paid it off was locked up instead. I’m not saying pay off every debt before you contribute a dollar. I’m saying “take the match” gets handed out as a blanket rule for everyone, and it isn’t one.

The third bet may be the scariest. Most people read the account balance as fully theirs. Some real piece of it isn’t. It’s sitting right there, uninvoiced, and the size of that invoice isn’t up to you, and there are 2 invoices to be paid.

The invoice that gets paid along the way is for fees on your contribution and on the match, and on the government’s eventual share of both, since nobody separates that out ahead of time.

Then the 2nd invoice is the tax that hits the full balance when it comes out, growth included, so the better that account performs, the bigger the government’s cut gets too. Grow it 10% this year, and you just grew the government’s future tax bill by 10% right alongside your own account. Pay the tax up front instead, and that money is entirely yours to manage or not. The government is left figuring out how to invest its own share, on its own dime.

But the 4th bet, the one underneath all the others, is this: what might employers and employees be doing if they didn’t default to the 401k and a matching program? I know someone who tested this directly: a young professional who used not taking the match as their main leverage point in a salary negotiation and got a higher wage because of it. That’s one option employers have: pay it out in W-2 payroll instead. Or they could go back to what they used to offer: a pension.

A pension is a defined benefit. The employer keeps the account, carries the risk, and owes you a number down the road no matter what the markets do in between. That’s not a guarantee either. Pensions get frozen, plans go underfunded, and when a company can’t pay, what you actually collect can shrink. But the risk sits with them first.

A 401(k) is a defined contribution. The employer’s job ends the moment they hand over the match. Everything that happens after that is entirely your risk to carry. That’s the actual wager.

What if all 4 wagers were part of the enrollment meeting on an employee’s first day? Not just whether your tax bracket goes up or down, but whether the rules governing that account even look the same by the time you need it. Congress could change what a 401(k) is allowed to do tomorrow, and nobody sitting in an enrollment meeting today has any say in that.

It’s like sitting at a poker table where the other player can see your cards. The government can see exactly how much sits in every 401(k) in the country, added up, and writes the rules accordingly. They’ve already pushed back the age you’re required to start pulling money out, more than once, letting balances grow bigger before any of it gets taxed. You don’t get to see their hand. You just play whatever cards you’re dealt at your enrollment meeting and hope the rules haven’t moved by the time you cash out.

My dad’s definition again: gambling is having something on the line in an outcome you don’t fully control. Driving from point A to point B, I have some control ... I can watch the road, avoid a bad lane change ... but I still can’t guarantee I arrive. Saving today toward a financial goal decades out works a similar way. More attention doesn’t guarantee the outcome. It just changes your odds.

You’ve been making this bet. You may not have known it was one.

Subscribe now

Have you ever thought about your 401(k) this way ... as a bet, not a savings account? Does it change how you think about it?

(Third in an occasional series about zombie ideas in personal finance ... ideas that were true once, or sound like math, and outlive the world that made them true.)

A client came to me holding three financial products, bought at three different life stages from three different people who’d sold them. One was betting on the market with no real guarantee behind it. One had most of what they paid in quietly going toward a temporary add-on instead of building anything that would last. The third was so old nobody could even pull a current statement on it.

None of the three were bad decisions at the time. Each one probably made sense to them in the year they bought it, for the person they were then. Nobody had ever sat all three next to each other and asked the only question that actually mattered: do these work together?

They didn’t. The fix wasn’t finding a better product. It was consolidating years of piecemeal buying into one coordinated structure. It’s a frequent story I come across about products that were never asked to be a system.

The gap many live with stays invisible until real life goes looking for it: a flood, a lawsuit, a slow season, a market drop, or a diagnosis. Having some stuff ... a 401k here, a product there, an account you opened for a reason you don’t fully remember ... feels identical to having an architecture, right up until the day something tests whether the pieces were actually built to hold each other up.

Business owners do this with more than financial products. Over time, they add a bookkeeper, a CPA, and an advisor. Each one is competent. They work strictly in their own lane. None of them look at the other lanes at the same time. Everyone’s doing their job well. Nobody’s job is to ask what’s missing between them. The coordination is actually the whole ballgame, and it’s usually nobody’s job until something breaks.

Some people will read that last paragraph and think the separation is the point ... keep the bookkeeper, the CPA, and the advisor in their own lanes on purpose, so no one person ever sees the whole board or has the opportunity to take advantage of the situation. That instinct isn’t wrong. Spreading out who holds your information and your money is smart. I’ve heard it said more than once, “The person who reconciles the accounts and the person who writes the checks should never sleep in the same house.”

But that’s not what’s actually happening in most fragmented setups. For the client in the opening story, no one sat down and decided that those three products shouldn’t talk to each other for safety’s sake. They just never talked, because checking was never anyone’s job.

I offer to get on a call with a client’s CPA or bookkeeper more often than people take me up on it. Most of the time it doesn’t happen. But even without that call, I can still hand someone the bigger picture ... what to ask their CPA, what to watch for, sometimes flat-out telling them to go talk to their CPA before we move forward with anything. That’s the difference. Everyone doesn’t have to be in one room. Someone just has to be looking at the whole board.

Diversifying on purpose and drifting apart by accident look identical from the outside ... right up until the day something pushes back or goes wrong.

Here’s where the gap actually starts, though. Roughly half of Americans have never worked with a financial planner of any kind ... The CFP Board’s own research puts the number at 53% who have. That’s the ceiling, not the real number. A lot of that 53% only ever got a conversation about stocks, bonds, and mutual funds, which isn’t the same as having someone look at everything they own side by side.

Most of the people in that other half aren’t skipping it because they don’t care. They’re skipping it because “financial planner” sounds like a service for people with more money than they have, or because the planners they’ve heard of only talk about stocks, bonds, and mutual funds ... which isn’t what a business owner juggling inventory, payroll, and a slow season needs, and it isn’t what a real estate investor with five mortgages and a property under contract needs either.

I was in my twenties before I ever knew that a financial planner was an actual thing. I knew of insurance agents, financial advisors, tax professionals, and attorneys. I had read many a financial book and even started a business. Maybe I was arrogant, thinking I didn’t need a financial planner when I finally met one, but looking back, I probably thought they were for someone who made or had a lot more money than me. I couldn’t have been more wrong. In 2013, I started working with a financial planner. The previous year, my net worth and my tax return taxable income line were both negative numbers because we were still in the start-up phase of our first business. Whenever someone thinks a financial planner isn’t for them because of a lack of resources, I have the personal experience to tell them that’s not true. If a negative net worth and income didn’t disqualify me, yours doesn’t either.

Today, I’m a CFP® (CERTIFIED FINANCIAL PLANNER®) professional. I enjoy what I do because I almost never talk about stocks, bonds, or mutual funds. I discuss cash flow systems and liquidity architecture for people who own businesses and buy property. Sometimes we do a portfolio review, but it’s not my first go-to. The credential means I’ve been trained and tested on the whole picture, not that I only do the parts of it Wall Street sells. If the only version of financial planning you’ve ever met only talks about stocks and mutual funds, what you’ve actually ruled out is one version of it, not the whole idea.

I keep coming back to “so far, so good” because it’s the sentence that sounds like relief and functions like risk. It’s not wrong, exactly. Things might be “fine” right now. The problem is what the sentence is quietly doing while it sounds true: it’s letting you mistake “hasn’t been tested” for “has been checked.”

The people who catch this before the test aren’t the ones with the most products. They’re the ones who occasionally stop and ask whether everything they’ve built is actually still talking to everything else they’ve built. Then, they ask, “What if?” and begin to find the places where a situation can be solidified before the crisis shows up and reveals the cracks that were there all along.

Subscribe now

What I didn’t know yet was how much we already had in common before we’d ever had a real conversation.

Brandon was a sick kid. His baby book says pneumonia three times before he turned one. He was still learning to walk while other kids his age were learning the alphabet.

He joined the Marines partly to prove to himself that he could. He also believed serving his country, putting himself on the line for other people, was one of the truest ways to make the world better.

About three and a half years in, he got mixed up with the wrong people. He was offered a way out ... give up the names of the others involved. He wouldn’t do it. He lost his veteran benefits over a choice most people wouldn’t have had the nerve to make.

From there he took an internship in the music industry, believing music could change people the way art and culture do. The longer he was inside it, the more disillusioned he got. What actually moved him, it turned out, was the volunteer work he’d started doing at church.

We met because his church was the same type as my church, where I was also actively involved.

Our type of church had a habit: if you showed any sign of being a leader, you were assumed to be a church planter (someone who starts new churches in new areas). It seemed like the minute people knew we were serious about our relationship, they already surmised ... we’d be doing ministry and planting a church together.

Sometime in our first year of marriage, we drove from Chicago to a conference outside Baltimore called Reform. This conference was put on partly by people in our denomination and partly by outsiders they’d invited in. We were newlyweds with no money. We slept in a tent. It rained.

We had no idea that conference would end up shaping the rest of our lives.

One of the people we met there was a man named Tri Robinson. He talked about an idea that’s stayed with us and has come up over and over again the last 20 years: most nonprofits set up downstream, along the river of poverty, pulling people out of the water. Feeding them. Housing them. It’s necessary work. Yet, almost nobody goes upstream to ask why people keep ending up in the water in the first place ... leadership, education, healthcare, environmental stewardship, the things that prevent poverty instead of just responding to it.

I’d grown up on nature documentaries wanting to save something. Brandon had just spent years trying to prove he could put his life on the line for people. Neither of us had language for it yet, but we were both already looking for the same thing.

We looked at each other and thought, “Obviously. Why isn’t everyone going upstream and trying to fix the river of poverty at its source?”

We’ve come back to that idea in every version of what we’ve built since.

Yes, at one point, we tried to be church planters. We didn’t fail as much as we learned there’s a whole wide world of making a difference that counts as “doing and being church” without the religious necessity of walls and pews.

With the coffee shop, we couldn’t promise every farmer would get paid a specific amount, but we could do our part ... and fair pay ripples into a family’s health, their kids’ education, and the whole shape of their life.

Now in financial services, this river analogy continues to drive us.

Most of the financial advice you’ve ever gotten is downstream. It shows up after the emergency, not before it. A budgeting rule you get handed once you’re already broke. A loan you scramble for once the roof is already leaking.

Along the way, we’ve picked up some financial wisdom that pulls us upstream. Bank On Yourself exists so we have liquidity built up before the emergency shows up, not after. Profit First exists so our business never gets close enough to missing payroll to need rescuing in the first place. Neither one is glamorous. Nobody throws a parade for the rescuing that didn’t need to happen, the same way nobody throws a party for the food pantry that never needed to open.

Anyone who really understands how the river moves ends up choosing what to do with that knowledge. Some learn to exploit the current and get wealthy off the same flow that leaves everyone else stuck. Others spend their lives swimming upstream and trying to fix it where it’s broken.

For at least the last forty years, money in this country has flowed toward the wealthy at the expense of everyone else. The current is being exploited.

Brandon and I have always chosen to swim upstream. We don’t pretend to have invented something new. Many have come before us, and many more will come after. We call our version “Counterflow.” Join us. Work against the current, on purpose, and fix what’s broken upstream.

Subscribe now

Where in your own financial life are you doing downstream rescue work, when you could be building upstream instead?

The same split shows up with money, whether or not anyone in the room would call it that.

A nice advisor tells a business owner who’s ready to grow: “That’s exciting. Let’s make it happen.” It’s the answer that matches the energy in the room. Nobody feels talked down to. Nobody leaves the meeting deflated.

A kind advisor asks a different question: “How are you funding it?”

Not “can you afford it” ... most business owners can technically afford almost anything for a little while, on a card or a loan or good intentions. The real question is whether the growth is going to be funded by cash that’s already sitting there, ready, or by cash that hasn’t shown up yet and is being counted on anyway.

This isn’t just an advisor thing. My son is eight. When he brings me a drawing, I tell him it’s great, because at eight, effort is the whole point. If he’s still bringing me drawings at eighteen, hoping to make a living from it, telling him it’s great stops being kind. It’s just nice. At some point, he needs someone willing to tell him what’s not working yet, not just someone clapping.

A few years ago, Brandon and I had the chance to stop being two individual financial professionals working next to each other and become something bigger: co-CEOs of an actual financial services firm. Real growth, the kind you say yes to.

It also meant real new overhead. Being a firm costs more than being two people with desks near each other. And the revenue that was supposed to justify the new expenses didn’t show up on day one. It showed up later, the way it usually does. For a while, we were paying for a bigger version of ourselves before that bigger version was paying for itself.

This is exactly the moment where Profit First quietly breaks for a lot of business owners. The system works by paying your profit and your owner’s compensation first, then running the business on what’s left. It’s brilliant right up until a growth expense doesn’t fit inside what’s left, and the temptation is to raid the accounts you promised yourself you wouldn’t touch. Once you do that once, the discipline is gone. You’ve taught yourself the rule is optional.

We didn’t raid the accounts. We used the cash value we’d already built in our Bank On Yourself type policies to cover the gap while the new revenue caught up. The Profit First structure stayed intact the whole time. We didn’t have to choose between growing and keeping our word to ourselves.

Profit First and Bank On Yourself aren’t two separate ideas we happen to both use. One makes the other possible. Profit First is what creates the surplus in the first place ... it’s the cash flow structure that keeps a business from spending itself broke on its own way up. Bank On Yourself is where that surplus goes to become something usable. Without a place for the surplus to live and grow, “pay yourself first” is just a nice idea you’ll abandon the first time growth gets expensive. Without the structure that creates the surplus, there’s nothing to “bank” in the first place.

Most growth advice skips this part entirely. It treats growth like a decision you make with excitement and figure out the funding for later. That’s the nice version. It feels good in the meeting. It’s also how a lot of otherwise solid businesses end up stretched thin, servicing debt they took on to fund a “yes” that came before the money did.

The kind no is a sequencing question, not a rejection of ambition: liquidity first, then growth ... not growth first, with liquidity as a hope. Wait long enough to have already built the thing that pays for the next thing. It’s a harder answer to give and a harder one to hear, because “not yet” doesn’t feel as good as “let’s go.” But “let’s go” funded by nothing is how a good year turns into a stressful one.

Nice and kind can sound identical in a single meeting. The difference shows up in what gets asked next: “does this feel right to you?” versus “how does this actually get funded, and what happens to the rest of your plan while it’s being paid for?” Nice lets a good year carry an optimistic assumption forward unchallenged. Kind asks what the same decision looks like if next year isn’t as good.

If you want to know which one you’re getting, pay attention to what happens when you say yes fast. Nice matches your energy and moves on. Kind slows down long enough to ask where the money’s actually coming from ... even when the answer is still yes.

And to demand kind treatment instead of just nice, go ahead and ask your own what-if questions. If you want to be treated kindly, treat others kindly in return. If you want to keep it surface-level, smile and keep your not-so-nice thoughts to yourself. I hope you’ll choose kind when you talk with me.

Subscribe now

Where in your business are you funding tomorrow’s growth with money that hasn’t arrived yet?

It made us think a lot about “emergency funds.” The replacement cost more than Dave Ramsey’s famous starter emergency fund ... a whole lot more. Even the hotel stays would have come close to blowing through the starter emergency fund. Thankfully, we questioned the typical advice years ago ...

We got into a conversation about emergency funds in a recent group coaching call. A participant brought up that number everyone who’s been through Financial Peace University can recite in their sleep. He wanted to know if it still made sense.

I quickly jumped on a quick fact search. Financial Peace University started in 1994. That’s 32 years ago. Over to an inflation calculator, and $1,000 in 1994 is equivalent to $2,253.39 today. I asked the group: how responsible is that, really? Would $2,253 have covered our HVAC? Not close.

Another client jumped in with the number I think about even more than Ramsey’s. There’s a widely known stat (originally from this report) that a huge share of Americans can’t cover a $400 emergency. If you’ve ever had a true emergency, you know it’s never actually $400. It’s the bill that starts at $400 and ends somewhere else entirely, same as our HVAC did.

Which got us thinking ... if the $1,000 emergency fund is such a commonly held belief, why do so many struggle to cover even $400 ... let alone something much bigger?

And before you blame inflation, keep reading.

The zombie idea is the number itself: a single figure, introduced 30 years ago as a starter goal, still gets repeated today as if it were a finish line. Ramsey never claimed $1,000 was a full emergency fund ... his own framework moves you to 3 to 6 months of expenses in a later step. But the $1,000 is the one that stuck in the culture. It’s the one people quote at parties. It never got adjusted, and somewhere along the way, a lot of people stopped hearing “starter” and just heard “enough.” Then, the $1,000 gets raided over and over again and never stays anywhere close, especially with the debt that piles up when the true emergencies are more than $1,000.

Even the 3-to-6-month standard has the same problem underneath it: it was built with one kind of household in mind, and it gets handed out to everyone regardless of what their life actually looks like. Two people in that same coaching call, both business owners, said versions of the same thing without prompting each other. One put it plainly: if something goes south with the business, you need something in storage for the business and something in storage for you. She’s aiming for closer to a year. The other, newer to ownership, hasn’t settled on a business number yet, but knew instantly that whatever a W-2 employee needs, he needs more. Nobody told them to say that. They arrived at it separately, from the same math: a business owner is covering two sets of risk with one household’s income, and the textbook number was never built to hold both.

For my family, the HVAC was one test. Brandon’s car was another. It got totaled in the same storm, and the insurance payout didn’t cover a replacement. To recover, we aren’t dipping into an “emergency fund” account, because we don’t have one. [gasp!] If you looked at our YNAB categories, there’s no line item called “emergency fund.” What we have instead is a 10/10/10 split: after our tithe, 10% goes to short-term savings, 10% to medium-term, and 10% to long-term. When something happens, we pull the gap from whichever bucket fits, usually medium-term, and keep building it back up.

This isn’t something we invented. It comes from Tim Austin, who learned it from people in their 70s and 80s back in the early 1980s ... he calls it common practice for the generation that lived through the Depression and came out the other side with real financial instincts. It’s written up in Pamela Yellen’s book The Bank On Yourself Revolution (pages 129-130 to be precise). Long before “emergency fund” was a category on anyone’s budgeting app, this was just how people who’d been through hard times built resilience: not one pile of money you’re afraid to touch, but several categories doing different jobs, all available if the basement floods again.

Where we keep this money matters too. It needs to stay accessible without losing ground to inflation, so we use a specifically designed whole life insurance policy instead of a savings account.

A friend of mine does too, and she’s very specific about how she treats her funds. She earmarks about 10% of her policy’s cash value as her business’s emergency fund ... right now it covers roughly 2 months of expenses, and she’s building it further. When her business needed to pay off a variable-rate line of credit that was bouncing between 9-12% interest, she and her husband loaned the business the payoff amount straight from that cash value, with a real promissory note and an amortization table. The business pays them back monthly, with interest, and they use that payment to repay the loan against the policy. Same dollar, doing more than one job.

Whatever your storage place for your savings, a number that was never meant to be permanent got treated like gospel (pun intended) for 30+ years. That’s the actual problem, not the dollar amount.

You might make more and still spend every dollar you earn, wondering how you’ll ever build a bigger pool of accessible cash. If you want a bigger emergency fund, or a different way of thinking about one, my favorite question is this: “What would have to be true first?” That could look like an income increase, a debt paid off, a bucket renamed into something you’re actually excited to fill. Solve what needs to be true first, set things up to build the reserves, and then the number moves on its own.

Our HVAC and car didn’t check what we’d budgeted for. Neither will yours.

Subscribe now

What number were you taught to treat as “enough,” and have you ever actually checked whether it still is?

Leave a comment

We’ve lived in this house since 2020. It’s flooded twice before, a few inches each time ... enough to be annoying, not enough to be alarming. This time it was feet, not inches. And it wasn’t just our house. It was the whole street. The pipes that failed don’t run under our foundation. They run under the road, and every house that drains into them found out at the same time we did.

Those pipes were laid around 1940 (when most of the houses were originally built). For eighty-some years, the pipes did their job. Then a storm came through that dumped more water, faster, than they were ever sized to carry ... hotter air holds more moisture, and when it lets go, it lets go all at once, in a way nobody designing a drainage system in 1940 had reason to plan for. The pipes did a 1940’s job in a 2026 reality.

So far, so good, is the entire logic of underground infrastructure. Nobody thinks about the pipe until the day the whole street finds out at once it can’t keep up. The city is supposedly bringing in the Army Corps of Engineers to help make sure this doesn’t happen again, but what if it didn’t have to happen in the first place?

I’ve been sitting with an idea from the economist Paul Krugman. He wrote a book called Arguing with Zombies: Economics, Politics, and the Fight for a Better Future ... I haven’t read it yet, I heard him talk about it in an interview, but the phrase stuck. He calls certain ideas “zombie ideas”: theories that keep shambling along no matter how many times they’re disproven, because they were never really being kept alive by evidence in the first place. They’re kept alive because somebody benefits from you still believing them.

Money runs on its own zombie ideas. But unlike real zombies who are created from a bite and are sustained by human flesh (sorry for the graphic reference), zombie ideas can be created and sustained in all sorts of ways.

Some personal finance zombie ideas were true once, and the world moved out from under them ... the same thing that happened to the pipes on our street. “Pay off your mortgage as fast as you possibly can” took hold during the Great Depression, when mortgages could be called at any time. The bank could demand the full balance, on its own timeline, whether you were ready or not, and plenty of families lost their homes because they weren’t ready when the bank called. Getting the mortgage gone fast was survival, not a preference. Mortgages haven’t worked that way in decades. They can’t be called anymore. That rule was correctly sized for a world that no longer exists ... which doesn’t mean it’s wrong for everyone now. It means it stopped being automatically right for everyone, the way it used to be.

Some personal finance zombie ideas were never true. They just sound like math. “Buy term and invest the difference” gets repeated like a law of arithmetic, but it developed as a sales pitch ... a way to sell one kind of policy by making the other one sound irrational. This zombie idea was marketing wearing a principle’s clothes from the very first day.

These zombie ideas have different origins, but the same reason both are still standing: changing either one costs somebody something today ... a commission, a sense of certainty, an uncomfortable conversation ... and nobody wants to pay that bill while the old idea still sort of looks fine.

I was born on public assistance in rural Ohio. I watched a macro version of this play out inside my own house before I had language for it: an economic idea called trickle-down, built on the theory that wealth at the top would eventually reach families like mine. It didn’t. My mom went back to college in her 30s, got us off public assistance, and provided for the family with her own sweat and stress, with very little “wealth” to show for it.

There’s a tin-foil hat version that says the failure of wealth making its way to us was because someone was lying about the theory on purpose. More likely, whatever truth it once had didn’t survive contact with the world it was actually being asked to work in by the time it reached my kitchen table.

I don’t write about zombie ideas in economics or in personal finance as an abstraction. I write about them as the water in my basement now and food on my kitchen table in the 1980s and 90s.

I hope to write more pieces about zombie ideas in personal finance and maybe even connect them to economic ones. The idea is to name one specific zombie idea still running in personal finance ... something everyone repeats because it used to be true, or because it sounds like math, and ask whose interest it’s actually serving by staying alive.

The meteorological storms aren’t 1940’s storms anymore. I pray we don’t repeat the same mistakes of that decade politically, economically, and internationally. Practically speaking though, it’s worth checking whether your pipes and your financial “rules” are sized for the future that’s actually coming. Are they even sized for today?

Subscribe now

What’s a piece of financial advice you were taught that you’ve started to wonder if anyone’s actually checked lately? Tell me which one and perhaps it’ll show up in a future post.

Their competitors had figured out something cheaper. Ground-up chicken feathers, dyed and treated to look and feel like down, are sold at the same price as the real thing. There was no government agency checking. No inspector walking the floor asking what was actually inside the pillow on the shelf. Just a label, and whatever the label claimed.

So the family did the only thing left to do. They bought their competitors’ pillows off the shelf, tore them open, and tested what was actually inside. Then they took what they found to the retailers and the press. They became the industry’s own fraud police because nobody else was coming.

Any retailer still stocking the fake stuff wasn’t actually saving money. They were borrowing it from next season. When the down went flat after a winter of use, the customer noticed and didn’t come back for a second pillow.

That’s what policing almost always actually looks like. Not a government agency with a badge. Somebody willing to open the thing up and look, and willing to say out loud what they found.1

Regulation still has a real job in that story, and it’s a good one. A pillow company should have to tell the truth about what’s in the pillow. Nobody’s arguing otherwise. What regulation shouldn’t do, and mostly doesn’t try to, is decide how many pillows you buy or whether you need a new one this year. Force the label to be honest. Leave the choice alone.

Same with a soda: require the can to list what’s actually in it, let adults decide for themselves whether they’re having one today, but don’t put sugary soda as the only option in an elementary school. That’s the tension worth holding, and it’s the same one that shows up with money.

The same question works on money as it does on pillows. What’s actually inside this?

Insurance regulation requires an accurate illustration, the same way food labeling requires an honest ingredient list. Both rules exist and are doing their jobs. Neither one requires anyone to sit down with you and explain what the numbers actually mean, or whether something technically true is actually right for you.

Most people never ask that second question. Not because they don’t care, but because there’s a cheaper sentence sitting right there instead: “So far, so good.” It costs nothing to say and everything to believe. It’s the most expensive sentence in financial planning, because it’s a description dressed up as a plan. Nobody checked. Nobody opened it up. It’s just been fine so far, which is not the same thing as it being real.

More than once, I’ve sat down with someone who’d already been in an IUL or a VUL (if you don’t know those acronyms, search them at your own risk) for a couple of years, money going in every month, believing it was working because someone had sold it to them well. I pulled up the actual illustration, the real numbers the policy itself was projecting, and walked through what they meant over the life of the contract. I wasn’t selling anything. I was just the first person who’d shown them what was already true.

A couple I’ve worked with for years had a managed investment account they’d trusted for a long time. I pulled it up with them one afternoon and we looked at the top holdings together. Neither of us recognized the top three companies. So we put them into a search engine, right there, and looked at what those companies’ stocks had actually done over the last several years. One of them told me he felt like he was going to be sick. The account had been quietly underperforming a rising market the entire time. Nobody had shown him. Nobody had asked him to look.

Neither of those conversations happened because I thought either of them was in over their head. The instinct to assume someone can’t handle a real number is exactly the wrong one. I’d rather assume they can, and hand it over straight. No teardown, no accusation, just the truth stated plainly. The “chicken feathers” were “So far, so good.” Thus, I did the same move the pillow family made: open it, look, say what’s actually there.

It comes down to something I call “Nice vs. Kind.” It’s really a distinction about when you pay. Nice is cheap right now and expensive later. Kind costs something today, on purpose, so the bill doesn’t come due bigger down the road.

The retailer who cuts ties with a cheating supplier eats a real cost today: a pricier source, an awkward conversation, and a few weeks scrambling for new inventory. The retailer who doesn’t pays a bigger one later, once the pillow goes flat and the customer doesn’t come back. Nice didn’t avoid the cost. It just moved it downstream and let it grow.

Money works the same way.

Nice doesn’t open the illustration or look up the holdings. It lets “so far, so good” stand, because pointing at what’s actually inside is awkward and nobody wants to be the one who ruins a good mood with a real answer.

Kind opens it anyway. Then, if it turns out to be “chicken feathers,” it ends a relationship with the wrong financial professional, which costs something now, maybe just the time, sometimes a transfer cost or a surrender fee. Staying costs more later: the day a downturn tests an architecture that was never actually built to hold, and takes a real portion of the portfolio down with it.

Markets do their own version of policing eventually, whether anyone asked for it or not. A down market doesn’t knock first. It doesn’t wait for a convenient time. It just opens everything at once, all at the same time, and whatever was actually inside shows up whether you were ready to see it or not. Two people can hold the exact same market exposure and walk out of the same downturn in completely different shape, because one of them had already looked at what was inside and the other was still running on “so far, so good.”

The pillow company couldn’t wait for a regulator who was never coming. Most people can’t wait for a downturn to tell them what’s actually in their portfolio, either. The check has to happen before the thing that forces it does.

So, who’s checking what’s inside yours?

Subscribe now

Has anyone ever actually shown you what was inside your own portfolio, your own policy, your own plan ... or has it mostly been “So far, so good”? Tell me which one in the comments.

Here’s what that story leaves out: the richest 10% of Americans own more than 80% of the value of the entire stock market. When a company buys back its own shares or pays out a dividend, that money is overwhelmingly returning to a narrow slice of people who were already at the top. Most of us buying an index fund in our 401(k) aren’t really investing in anything. We’re speculating on a price, hoping to sell at a higher price than we bought. The company doesn’t get our money. Another shareholder does, on the other side of the trade.

None of that requires anyone to be a villain. Nobody has to intend for wealth to concentrate upward for it to concentrate upward. That’s just what the ownership structure does, on its own, every single day, whether anyone in the building is thinking about it or not. The stock market was sold to us as a wealth equalizer. Structurally, it’s closer to the opposite.

But I’ve belonged to ownership structures that actually work the way the stock market is supposed to work. And I noticed the difference long before I had language for it.

In college, our bookstore was student-owned. You bought a share in your freshman year. For the next four years, you got a discount on every book you bought there. When you graduated, you sold your share back. I didn’t think of it as an economic philosophy at the time. It was just how the bookstore worked. But the person buying the textbook and the person who owned the store were the same person, the entire time.

I’ve been a member of REI for years for the same reason, even if I never framed it that way until now. It’s a co-op. You buy a membership, and the more you shop there, the bigger your dividend back at the end of the year. REI doesn’t answer to a hedge fund demanding better numbers by Thursday. It answers to the people buying tents and hiking boots, because those are the same people who own it.

My local credit union works the same way. I don’t earn an APY on my savings account there. I earn a dividend. That’s not a marketing choice, it’s an accounting fact. I’m not a customer. I’m a member. There’s no shareholder somewhere else getting paid first and leaving me whatever’s left over. There isn’t anyone else. The people with savings accounts are the same people the credit union exists to make sure come out ahead.

And I’ve held policies with mutual life insurance companies for years, long before I had the language to explain why it mattered. I just knew, the way you know things before you can explain them, that something about it felt different from every other financial product being sold to me.

That feeling has a mechanism behind it. Insurance companies come in two structures, and almost nobody teaches the difference. A stock company is owned by shareholders, as is any publicly traded corporation. Those shareholders expect a return on the schedule investors care about: quarterly earnings, growth targets, and the next call with analysts. When a stock company needs to hit a number, someone in that building is deciding what to trim to get there.

A mutual company has no shareholders. The policyholders own it. There’s no outside investor demanding a number by Thursday because there isn’t one at all. Profits either come back to policyholders as dividends or stay inside the company as surplus, strengthening the reserve that backs every promise it’s made.

Regulators set a minimum capital cushion for every insurer, a ratio measuring how much surplus a company holds against the risk it’s carrying. One of the mutual companies I personally hold a policy with runs that ratio above 400%, more than double what regulators require. It’s been paying claims for over a century, through wars, depressions, and every market cycle in between. Nobody made those choices to hit a number for someone else. They made them because the policyholders and the company are the same people, and there was no one else to please.

That difference sounds small until you remember what a life insurance policy actually is: a promise made today that has to hold up for 15, 30, or 50 years. Nobody knows what the world looks like in 2030, let alone 2056. What you can know right now is who the company answers to while it gets there. If the answer is shareholders, you’re one interest group away from the people the promise was actually made to. If the answer is the policyholders, the ownership and the promise belong to the same people, the whole way through.

The bookstore, REI, the credit union, and a mutual insurance company … 4 completely different industries, running on the same underlying idea: put ownership in the hands of the people the institution is supposed to serve, and the incentives point the same direction the whole way through. Separate ownership from the people being served, and eventually, not always on purpose, the benefit drifts toward whoever holds the shares.

None of this, on its own, undoes the fact that 80% of the stock market is held by the wealthiest 10%. My bookstore share didn’t rebalance anything, and neither will your credit union account nor another mutual insurance policy. But an economy doesn’t move because of one grand decision. It moves because of millions of smaller ones, made by people who mostly have no idea they’re voting on anything. Every time one more person chooses the credit union over the bank, or the mutual over the stock company, a little more capital sits behind the structure built to serve the people using it, and a little less sits behind the one that isn’t. Nobody has to organize a movement for that to be true. It just takes enough of us asking the question in the first place.

Most agents will never bring up the stock-versus-mutual distinction. Not because they’re hiding something. Because almost nobody trained them to think about it either. It’s not on the exam. It’s not in the sales materials. It’s sitting underneath every policy, the same principle sitting underneath your 401(k), your bookstore membership, and your co-op card, waiting for someone to ask who actually owns the thing.

So ask … and not just about your insurance. Ask anywhere you’ve handed over your money and assumed the incentives were aimed at you.

Subscribe now

Have you ever belonged to something structured like this ... a co-op, a mutual, a member-owned anything ... and noticed the difference before you could name it? I’d love to hear it.

He’d seen the crash coming. Bet against it. When the market collapsed, he was on the right side of the trade. It was one of the most precise financial calls anyone had ever made. By the time it was over, he was one of the wealthiest people in America.

By 1934, he was bankrupt.

Not for the first time. Livermore had made and lost his fortune so many times that people stopped counting. He’d rebuild, accumulate, make it enormous, and lose it again. Bankruptcy kept finding him (or he kept finding it, depending on your perspective).

He died in 1940, having built more wealth than most people ever see. He left a note that said: “My life has been a failure.”

He was wrong about that ... but he was right that something had failed.

Livermore knew how to make money better than almost anyone of his generation. He could read the tape, time positions, and bet big when his read was right. His instincts were extraordinary.

What he never built was anything underneath.

His nervous system was wired for the hunt, not for the hold. Every time he accumulated a fortune, he put it right back to work. The same aggression that made him brilliant at capturing gains made him incapable of protecting them. He kept applying making-money logic to a keeping-money problem.

They’re not the same.

Making money takes timing, boldness, and knowing when to move. Keeping it is a different problem, one that calls for structure, patience, and knowing when to stay put. The skills that earn the first dollar do not automatically protect the thousandth one. The people who figure that out before everything is already gone are the ones who build something that actually lasts.

Most people rate themselves as above-average drivers. Statistically, that can’t be true. But most believe it anyway. Investing works the same way. Ask a room of people whether they’re above-average investors, and most hands go up, especially when the market’s been on a bull run for years. Yet, the numbers don’t bear it out.

Even a genuinely above-average investor isn’t protected. Livermore wasn’t fooling himself. He was legitimately exceptional. The track record said so. And he still kept losing everything.

Subscribe now

Brandon and I started our first business with negative net worth. We still had student loan debt. We had no assets. Everything we made in the early years went right back into building the business and paying down what we owed. We were excellent at making the revolving system hum. That part came naturally.

What didn’t come naturally was keeping.

Nobody we’d grown up around had taught us that part. You made money so you could spend it on what you needed, or put a little back for treating yourself. The idea that there was a different set of skills required to build something that changes the trajectory of a family for generations ... that was a different education entirely. One we had to go find.

Two things became the keeping layer: (1) A savings vehicle built around cash value life insurance that grows whether or not it’s a good month for the business. (2) Profit First: a structure where revenue goes where it’s supposed to go before we can make any other decisions with it. Neither requires predicting what the market does next quarter. They run on a different logic entirely. It’s a logic we had to learn separately. It’s more of a “get rich slowly, but surely” logic that depends on patience and structure.

Livermore never found that second education. He stayed brilliant at the hunt and kept losing the spoils.

The skills that got him to $3 billion were real. He just never built the thing that would let them matter past the next position.

What was your education in keeping wealth? Did you have to go find it, or did someone hand it to you?

He could pick anywhere in the world for his 40th birthday. We’d go. We didn’t have the money for it yet... but we were already building something that would get us there. We’d started building financial architecture the year before. The promise was real before the funds were.

In 2017, he turned 40, and we booked the tickets in early July. He picked Ireland.

Our coffee shop flooded at the end of July 2017.

Overflow Coffee Bar was a social enterprise café we’d built in Chicago’s South Loop. We’d poured years into it... the kind of years that cost you something you don’t always name until later. And then that fateful summer in 2017, the roof was off for repairs when a freak storm popped up. In the aftermath, revenue stopped, but the bills didn’t.

We’d already booked the flight. Now we were staring at a business mid-recovery, wondering whether we should still go.

Labor Day weekend, I finally took a pregnancy test. I’d been putting it off for weeks. There was too much happening after the flood, I told myself. The test came back positive.

That fall, we were quietly arranging what would become the sale of the business.

Five months. A flood, a pregnancy, and the beginning of an exit we hadn’t planned for.

We still had a flight booked.

Subscribe now

Christmas Day, 2017, we got on the plane.

In Dublin, I found a small chapel at the back of St. Patrick’s Cathedral. It’s set aside for any faith... you don’t have to be anything to sit there. I don’t know how long I stayed. Just long enough for the quiet to do something. It had been months since I’d sat still without something on fire.

Brandon and I took the train from Dublin to the west coast to see the Cliffs of Moher. He’s a lifelong Princess Bride fan (the Cliffs of Insanity were filmed there), and standing at the edge of them had been on his list for as long as I’ve known him. Looking back on the photos I took of him there, he looked like himself again.

We flew home December 31. On January 2, 2018, we signed the papers to sell the business.

People ask sometimes how we pulled that off.

The honest answer is that we had something available that didn’t require our income to be steady to be there. Cash we could reach without penalties, without applying, or without liquidating anything we’d spent years building. The architecture held while everything else was shifting.

We didn’t plan for a flood. Or a pregnancy in the middle of it. Or a business sale to follow.

We planned the architecture. The architecture meant we could keep a promise made three years earlier ... even as we were letting go of everything else we’d built to keep it.

That’s still the thing, twenty years into our life partnership and sixteen years of business partnership.

We started with less than nothing, literally with student loan debt and no assets. We haven’t always made the right call or seen what was coming. Yet what we’ve built is something that could hold the weight of an imperfect plan. When the flood came, we had somewhere to go. The pregnancy came, and we weren’t scrambling. And when it was time to sell, we didn’t need the money badly enough to take a bad deal.

In a few days, it’ll be America’s 250th birthday. Businesses are already using it to try to make money. Financial gurus will talk about independence like it’s a declaration: a moment, a vote, or a date on a calendar. What we’ve learned is that independence is also a foundation. You have to build it so it’s there when life shows up.

Getting on that plane on Christmas Day ... that was what it felt like to us.

Next week is our 20th wedding anniversary. For us, it’s a celebration of the 1st “yes” that built 20 years of yeses and of the foundations for many more yeses to come.

What’s a moment you were able to say yes to because you’d built something that could hold it?

But that professional has never once reached out to them first.

Not once.

They don’t know what they don’t know. The questions they most need to ask ... they’ve never thought to ask. Because no one reached out with a different question first.

This isn’t a rare situation. It’s the norm ... especially below $1M in investable assets, and sometimes well above it.

If you’ve never heard of him, Cornelius Vanderbilt was a key 19th-century transportation figure. He went from a poor farmer to a NYC ferryman, amassing over $100M (over $3B in today’s dollars). His dying wish was to keep the money together. By the sixth generation, it was gone. His direct descendant, Anderson Cooper, works for a living.

Born 50 years earlier than Vanderbilt, Mayer Rothschild built up to only $6M (about $80M in today’s dollars — with the caveat that he was sophisticated and had already partnered with his five sons long before his death, so we’re not sure how much wealth he built into their families before he died). His dying wish was to keep the family together. They’re still there. At its peak, the family is estimated to have held hundreds of billions.

The families that lasted didn’t hold money. They held each other.

This isn’t a story about dynasty wealth. Middle-class families have understood this for generations. The neighbor who calls before you know you need help, like mine who always texts when we forget to close the garage door. The family member who calls you out on what you said you’d do but haven’t yet, like my 8-year-old son does sometimes. The community that shows up before you ask, like my block who started front yard hangouts during Trick-or-Treating to bring the adults together, not just the kids going door-to-door.

The financial industry has sold the myth that the best kind of professional relationship (the proactive, honest kind) only becomes available above a certain number. It doesn’t.

Some of the most significant turning points in my own financial life came from someone saying something I wasn’t expecting.

An attorney once asked my husband and me the wrong question — and it turned out to be exactly the right one. That story is here.

Richard Koch, a billionaire and author, answered a fumbling question from me in a live Q&A with seven words: “The name needs to speak to your strengths.” I’d been wrestling with something for years. That sentence ended the wrestling.

Brandon and I watched a documentary with Mark Willis. What we heard rearranged how we thought about money. It’s the foundation of what we do now.

When one of Brandon’s KPIs dropped, someone in our professional community didn’t encourage us. They said we needed to do better.

When our marriage was in real trouble, a spiritual mentor didn’t tell us everything would work out. They pointed us somewhere specific. We went. It worked.

Each time, we were grateful. Cheerleaders don’t help you get better. They help you feel okay about staying the same. Every one of those moments came from someone willing to say what we might not have wanted to hear. Not to be harsh. Because they cared enough to be honest.

A reactive financial relationship can’t do that.

If your advisor only responds when you reach out, they can never ask the question you didn’t know to ask. And the question you haven’t thought to ask yet is often the most important one.

You and your financial professional are probably spending more time and money managing your investments than investing in the relationships that will outlast every portfolio you’ll ever build.

The financial industry is loud. Returns are measurable. Relationships are not. So relationships get lost.

What if you didn’t have to choose?

What if the financial architecture you’re building is liquid enough to be there when a relationship needs it ... accessible without penalty when life asks something of you ... and designed so the long-term compounding doesn’t stop just because you had to show up somewhere that mattered?

That’s not a pitch. It’s a question.

A good financial planner should be asking it.

Before you think to.

Subscribe now

I told you a few of mine. Who’s the person in your life who’s told you something you didn’t want to hear ... and turned out to be right?