Live Counterflow

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 dividen...

In October 1929, while the rest of the country watched their savings disappear, Jesse Livermore made what would be worth $3 billion today. 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,...

Join the conversation at https://livecounterflow.substack.com/ . In 2014, I made Brandon a promise. 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,...

A family came to me recently. They have a financial professional. They ask good questions. They get answers. 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 ... es...

You built the thing. Scaled it. Maybe you even built systems so the business doesn’t need you every day. Maybe you’re on a list somewhere. And you still can’t step away. You can’t take a week off without your phone going off. You can’t survive a bad month without it becoming a personal crisis. You can’t take a season when life pulls you somewhere else — a health scare, a family emergency, the thin...

Our attorney sat across the table from us and asked one question. “Are you paying yourself what you’re really worth?” Brandon and I looked at each other, then looked down. We weren’t paying ourselves minimum wage from our own business, the one we’d moved five people into a three-bedroom apartment to fund, opened on credit cards with a negative net worth, and poured seven years of our lives into. W...

He kept stirring his coffee long after the sugar had dissolved. He had a solid business, a family, retirement accounts he’d built carefully for years. “If I had one bad quarter hit, the whole thing wobbles,” he said. Not collapses. Wobbles. That word stayed with me because I know exactly where it comes from. I’m the youngest of 11 children in a blended family, the one my parents moved in with, the...

In my early 20s, I learned about labor exploitation in the apparel industry. Not from a headline I skimmed. From sitting with the full weight of what the supply chain actually looked like: who made the clothes, under what conditions, and what their options were. It changed how I thought about getting dressed. I’ve never shopped the same way since. The financial equivalent of fast fashion is the co...

The people I hear this from aren’t reckless. They’re the responsible ones. They contributed consistently for 20 years, asked for advice, trusted professionals, and didn’t log in during market dips. Every review meeting ended the same way: “You’re on track.” Technically, they were. Right up until they weren’t. Almost half of all retirees leave the workforce earlier than planned. That number hasn’t...

I was in middle school the first time I sat down at the kitchen table with my mom and worked through every dollar of credit card debt our family carried. She didn’t ask me to. I just knew it needed to happen, and I figured I could help. That’s who I’ve always been ... the one who shows up when the numbers get hard. So I did everything right. I bought term insurance and invested the difference. We...

I recorded this episode for a friend of mine. He’s 25, smart, proactive, thoughtful ... and completely stalled on his own financial story. Two competing voices have him frozen: skip-the-latte gurus making him feel behind with shame, and hustle culture whispering that more income fixes everything. So he waits. Technically, he has time. That’s the most dangerous part. During long stretches of stabil...