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In May 2016, a couple of months after our first business turned five, I spoke to a class at a local university. 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. ... 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. ... What would your mission look like if it finally paid you? Leave a comment at https://livecounterflow.substack.com/. I read every one. 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. Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

“No, let’s plan around 10%. That’s what I’m going to assume.” 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. ... 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. Comment and subscribe at https://livecounterflow.substack.com/. 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. 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. Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

If you had $4 million in assets, no debt, and $70,000 a year of truly passive income, would you feel financially free? Maybe not as much as you’d think. ... 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 and comment at https://livecounterflow.substack.com/ Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

I was 21 the first time I was told I talked too much for how young I was. Then, 22 the second time. 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. Participate in the comments at https://livecounterflow.substack.com/ When did you go quiet because someone told you to take up less space ... and what would it look like to take it back? 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. Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

I wanted to be president of the United States. Not in the vague, anything’s-possible way kids get coached into saying ... I actually believed it, the way you believe things before anyone’s gotten around to telling you no. 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. Subscribe and comment at https://livecounterflow.substack.com/ What are you actually comparing yourself against when you feel like you should be farther along? Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

Most people build a safety net for one kind of phone call: the lawsuit, the client who walks, the equipment that dies on a Tuesday. That’s not wrong ... it’s just half the story. 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. Subscribe and Comment at livecounterflow.substack.com What opportunity have you had to pass on ... not because it was wrong, but because the cash wasn’t ready to move? Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

We were a small coffee shop making less than a thousand dollars a day, some days a lot less. Compared to Starbucks, we sucked. 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.” What’s the number in your financial life you never actually chose ... you just inherited it from a rule of thumb? Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

I’m not much of a bettor. As a kid, I made small bets and lost almost every one, until I just stopped making them. I remember losing one and having to walk about a mile over it. Nothing terrible ever came from any bet I lost. I just don’t like giving something up when I have no real control over how it turns out. 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. ... You’ve been making this bet. You may not have known it was one. 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? Comment at https://livecounterflow.substack.com/ (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.) Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

“So far, so good” is the sentence people say right up until the test arrives. Nothing going wrong feels like proof the system works. It’s actually just proof the crisis hasn’t hit yet. If you haven’t had someone look at everything you own side-by-side, what would it take for you to actually do that? Seriously, I want to hear your criticism and pushback. I’ll respond to each comment at https://livecounterflow.substack.com/ Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

In October 2004, Brandon hosted a bonfire that almost burned a house down. That’s the night we met. I grew up in the country. I love a bonfire. I went. I was dating someone else at the time, so when Brandon started calling afterward, I didn’t answer. We ran into each other again months later, and that time it stuck. What I didn’t know yet was how much we already had in common before we’d ever had a real conversation. Participate in the comments at https://livecounterflow.substack.com/ Where in your own financial life are you doing downstream rescue work, when you could be building upstream instead? Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

Mary Poppins was my favorite movie as a kid. I loved her the way kids love a good babysitter ... fun, a little magic, doesn’t yell. I understand her better every year I get older. She never flattered the Banks children or told Mr. Banks what he wanted to hear. She gave whichever medicine each of them actually needed, said the hard thing when it needed saying, and left the moment she wasn’t needed anymore instead of staying around for the thanks. That was never nice. It was kind. It took me over 30 years to notice the difference. 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?” Where in your business are you funding tomorrow’s growth with money that hasn’t arrived yet? Comment at https://livecounterflow.substack.com/. Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

In July, we experienced 5 feet of water in our basement. It put our entire HVAC system totally out of commission. In 90-degree weather with a 77-year-old living with us, we stayed in a hotel while we waited for the cleanup and new system to be installed. 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 ... What number were you taught to treat as “enough,” and have you ever actually checked whether it still is? Get the links and participate in the comments at https://livecounterflow.substack.com/ Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

Our basement flooded last Friday. 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? ... 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? 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. Comments are open at https://livecounterflow.substack.com/. Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

Years ago, a small family business made pillows. Real goose down, the good stuff, priced accordingly. 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. ... 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? 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 at https://livecounterflow.substack.com/. Get full access to Live Counterflow at livecounterflow.substack.com/subscribe

We’re told the stock market is the great equalizer. Buy shares, and you’re an owner. Put money in your 401(k), and you own a piece of corporate America right alongside the people running it. Everybody wins together. 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. Comment at livecounterflow.substack.com - 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. Get full access to Live Counterflow at livecounterflow.substack.com/subscribe