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The other day, I got a message from a reader named Akiva: “Yours is one of the few emails I get that I have to go back to later on my computer because I don’t have a browser on my phone. Always a good read.” Akiva built a system to avoid distractions — no browser on his phone. And somehow, my emails made the cut for “worth coming back to.” That message? It made my day. It reminded me why I write these emails in the first place. It also got me thinking: why do people like my emails? HERE’S MY SECRET (HINT: IT’S ABOUT NOT HAVING SECRETS) I wasn’t born with good money genes. I’ve bounced checks. I’ve spent emergency money on beer in Jamaica. I’ve felt that sinking feeling when I logged into my bank account and saw less than I expected. So when I write these emails, I’m not writing from a pedestal. I’m writing as someone who’s been through it. HOW THESE EMAILS HAPPEN I listen. Clients say things that stop me cold. I write them down. Readers send emails that stick with me. Conversations with family and friends spark ideas. I steal from everywhere. From […]

I was 19. Jamaica. I was traveling with an older friend, Rino. My mom was a flight attendant, so I was flying standby on her employee pass. Free flight — if there was a seat. No seat, no flight. A few days before heading home, I checked the flight. Looked wide open. It’ll be fine. So, naturally, I did what any 19-year-old would do: I spent my emergency money. More Red Stripe. Souvenirs. Whatever else seemed like a good idea at the time. Then I got to the airport. Overbooked. That means I’m not getting on the flight. ZERO My brain went into a spiral. Avraham, you’re so stupid. Why did you do that? Then the panic: What am I going to do? I’m all alone in Jamaica. Where am I going to sleep? The resort might not even take me back. What is my mother going to think? And finally: Those pilots better say yes. I’ll beg if I have to. I had zero money. Not “low on cash” — zero. And I was stuck in a foreign country with no way home. Rino? He had a confirmed ticket. Paid in full. He shrugged. “I’m sure it’ll be fine.” […]

Someone called me a “self-made man” the other day. I’ll admit — it felt good to hear. But here’s the truth: it’s completely wrong. THERE’S NO SUCH THING AS SELF-MADE I didn’t make myself. And I definitely didn’t get here alone. Let me tell you about some of the people who got me here. CHRIS REYNOLDS I was 17. He was starting an investment company. Thirty people. He gave me a shot. He used to call me “Junior.” Said he saw himself in me. I wasn’t the most responsible kid. One day, I smashed the company car. Couldn’t pay for it. He gave me another shot. That company now has over 1,000 people. And because he gave me a second chance, I got to witness that. I still think about what it meant that he believed in me when I didn’t deserve it. SETH GODIN He let me lead his community — 25,000+ people from the circle he built up over the decades. But more than that, he taught me something I still carry: Pick yourself. Don’t wait to be picked. That one idea changed how I move through the world. MY RABBI I had a mentor a few years […]

Today was one of those days with my kids. The kind where every interaction feels like a negotiation—and I was losing every single one. By the afternoon, I was fried. And when I’m fried, I do what a lot of people do: I start thinking about food I don’t need. Specifically, salmon lover’s sushi. There’s a spot in Toronto I love. $17 for a little tray of the good stuff. I wasn’t hungry—not really. But I wanted it. Because when I’m stressed, I reach for something that feels like relief. So there I was, standing in line, about to order. And then I caught myself. Wait. I have a choice here. I didn’t have to buy it. I wasn’t hungry. I was just stressed. And buying that sushi wasn’t going to fix the stress. Sure, it would taste amazing for about four minutes. But after that? I’d feel… kind of bad. Seventeen dollars poorer. Still stressed. So I didn’t buy it. And here’s the surprising part: I felt better not buying it than I would have felt eating it. 🍣 $17 ISN’T LIFE-CHANGING—BUT THE PATTERN IS I know. It’s just sushi. Not a car. But here’s the thing: I do […]

I was fifteen. Riding shotgun in a Chevy Astro. Pitch-black back roads. No streetlights. And the gas tank? Empty light on. Somewhere between ‘we might make it’ and ‘we’re going to die out here.’ Danny was driving — my cousin’s cousin. Eighteen. Built like a linebacker. This was my first big trip without Mom. Two weeks of relentless begging before she finally said yes. Wasaga Beach. Freedom. Except I spent half the trip staring at the fuel gauge. At one point, we were scraping together coins. Just enough to keep going. The needle taunted us the whole way. We made it. Barely. When I got home, I noticed something I’d never paid attention to before:My mom’s tank was full. It was always full. She never let it drop below half. Forty-plus years as a flight attendant. Emergency drills weren’t just something she knew — they were drilled into her. “If there’s a crisis, you need fuel. Don’t wait for the empty light.” Half tank to full tank. Always. Just in case. Fast forward ten years — August 14, 2003. I was 25. And Mom’s lesson was about to pay off. The lights went out… Fifty million people lost power that day. Detroit. New York. […]

I’ve seen this story play out hundreds of times. And I’ve lived it. (Just ask my wife.) Here’s how it goes: Your car’s service light came on two weeks ago. You’ll deal with it next week. Your kid’s sneakers are hanging on by a thread — he needs new ones before the weather turns. The Hulu subscription renewed again, even though you’ve been meaning to cancel it since November. And that budget you swore you’d make on January 1st? It’s now the end of February. One spouse brings it up. Cue a week of marital tension. That heavy, unspoken “we really need to figure this out” energy hanging over the house. So you sit down. You open the spreadsheet. This time, you mean it. You really do. But then… Your brother-in-law needs help moving on Sunday. A client email can’t wait until Monday. You’ve had a brutal week, and honestly, you’ve earned a night on the couch with a novel that doesn’t require brainpower. All reasonable. And the can gets kicked. Here’s the part no one wants to hear: You’re not just avoiding your finances. You’re avoiding the truth. That you’ve been underperforming with your money — for years. You […]

I’ve only seen it happen twice in 15 years. A client sits down. I show them the numbers. They look at the spreadsheet, make a decision, and execute. Cold. Logical. Done. One of those clients? He realized the math didn’t work. He was living in a country where taxes were too high, pay was too low, and his dream lifestyle was a pipe dream. So, he got a new job. In a different country. Within two weeks. Six weeks later, he and his family had relocated. Hundreds of thousands of dollars gained. No hand-wringing. No “let me think about it.” Just: this is the logical move, so I’m making it. His family followed. That was it. I sat there thinking: That’s how it’s supposed to work, right? See the numbers. Make the change. But here’s the thing: that’s not how it works. Not for most people. Not even for me. When I started as a financial coach 15 years ago, I came from the financial advisor world. I believed the answer was tools. Systems. Tracking. Show people where their money is going, and they’ll fix it. So, I built an app. Not just any app — a 12-month projection tool. […]

My wife doesn’t let me mop. It’s not that I don’t offer. I do. And yet every time the floor needs mopping, she takes over. On the rare occasion she lets me mop, I catch her re-mopping after. “I already mopped,” I say. “I know,” she says. “But you always miss spots.” She’s not wrong. Her mopping is a 10/10. Mine? A generous 7/10 (she says 5/10, but I’m sticking with my score). Here’s the kicker: she doesn’t even like mopping. It’s a big job — tile floors, kids, and a week’s worth of spills. Every Friday, she’s wiped out. But she can’t let it go. Why? Part of it is speed. She’s fast. I’m slow. “By the time I explain what you’re missing, I could just do it myself.” Part of it is standards. She sees grape juice stains and crumbs I don’t. But the biggest part? Identity. She told me, “I feel like I accomplished something. If I give it to you, it feels like something’s wrong with me.” Letting go isn’t just about trust. It’s about who she is. (By the way, she reads these emails. So: thank you for all the mopping. I see you. And […]

My wife has been on me for months.“You should do a speaking tour,” she says. “You’re great at this. People need to hear it live.” She’s not wrong. Speaking is how I’ve landed most of my best clients. And yet, here I am. Writing you an email instead of standing on a stage somewhere. Classic me. Let me tell you where this one started. My dad was 35 when he was diagnosed with leukemia. He lived another ten years — but I was only 12 when he passed. Old enough to understand what was happening. Old enough for the lesson to stick. He wanted to protect us. So he made some big moves. Bought a motel in Kissimmee, Florida — 15 minutes from Disney, where the parking lots are bigger than some countries. It never really took off. He also bought a farm to develop into office buildings. Then the market tanked. We got stuck with both properties. Huge mortgages. When my dad passed away at 45, the life insurance didn’t even come close to covering it. My mom — a widow in her 40s — was staring at ten thousand dollars a month in negative cash flow. In the […]