Essays

Essays on entrepreneurship, AI, M&A, disruption, and investing from the founder of Tatango. Straight talk on what it actually takes to build and grow.

Stop Comparing Autonomous Robotaxis to ATMs July 4, 2026 The two-question test that tells you which jobs automation kills and which ones it just changes.
The Math Says Keep Your Mortgage. I Paid Mine Off Anyway. July 2, 2026 Everyone runs the calculator. Almost nobody tells you how it feels.
When You Come Into Money, Only Make Decisions You Can Undo June 27, 2026 The version of you a year from now will know things you don't. Don't lock them out.
Cheaper, Faster, Better. But Mostly Cheaper June 18, 2026 Of the three ways to disrupt an industry, one does most of the winning. Here's the data from my own book, and how to actually use it.
ETA's Dirty Secret: You Can't Change the Business You Just Bought June 17, 2026 Entrepreneurship Through Acquisition (ETA) is the hottest path in business right now. Here's the biggest risk nobody warns you about, and it has nothi…
When the Money Lands, Stop Thinking in Monthly Payments June 16, 2026 The payment is built to make a big purchase feel small. Right when you can't afford to feel small.
Get Ready for the Retrade June 15, 2026 The buyer who agreed to your number in the LOI will try to move it right before closing, when you have the least power to say no.
Sell, Then Build June 15, 2026 Building has never been easier. That's exactly why so many founders are building things nobody pays for.
A Windfall Is a Math Problem, Not a Returns Problem June 12, 2026 Come into a big lump sum and you'll be tempted to fix the wrong problem. Here are the only two honest answers, and the one that ruins most windfalls.
The Best Dividend Isn't Money June 11, 2026 The one idea from Die With Zero that changed how Jessica and I plan our lives.
When You Get a Windfall, Pay the Taxes Immediately June 10, 2026 I did it both ways. One felt terrible. The other didn't. Here's what I'd tell anyone who comes into money.
How I Got Sober June 9, 2026 No willpower, no meetings, no recovery. Just a book.
I Asked Claude Which Industries It's About to Disrupt June 8, 2026 I went to the source. Here's the list, the three waves, and what survives.
Are we investing in the SpaceX IPO? June 7, 2026 Never bet against Elon, but does that mean we're buying SpaceX at IPO?
One Bidder Is No Bidder June 6, 2026 One offer feels like winning. It's the weakest hand you can hold.
I'm Betting on the End of Car Ownership June 6, 2026 Why Tesla is the only stock I own
Run a Sale Process, Even If You Never Plan to Sell June 5, 2026 A failed attempt to sell my company handed me the exact playbook to make it sellable a year later.
You Keep Judging the First iPhone June 4, 2026 You're rating AI on version one. Every industry that laughed at the first iPhone did the same thing, right before it ate them.
I Owned the Majority of My Company. I Almost Couldn't Sell It. June 3, 2026 Selling Tatango taught me that voting control and the power to actually close a deal are two very different things.
Why I Make Entrepreneurs 10X Their Goals June 2, 2026 Why setting a bigger goal forces you to do less, not more
The Second Bite of the Apple Is a $70M Deal June 1, 2026 What private equity's rollover equity pitch really pays founders, and the number you should actually anchor on.
Why Entrepreneurs Should Value Their Earnout at Zero May 31, 2026 Why you should value every deal at the cash up front—and ignore the rest.
Beware the Banker With the Biggest Number May 30, 2026 When the banker anchors too high, fair offers start to feel like insults, and great deals quietly die.
How Barrett Ersek Disrupted Lawn Care — and Changed My Life May 29, 2026 A man named Barrett Ersek rewired how I think about business. So I'm giving away the entire introduction to my book. My only ask is at the bottom.
The AI Chasm: Why Most Businesses Won't Survive the Jump to AI-First May 27, 2026 Why transitioning a traditional business to an AI-first model is nearly impossible, and what to do instead.
The Four Stages of AI in Business May 26, 2026 Coding lived through this in five years. Every other white-collar industry is next.
Two Ways To Protect Yourself When Raising VC May 25, 2026 If the odds of a founder payout are this bad, here's how to hedge.
You Just Raised VC? Sorry to Hear That. May 23, 2026 The founder payout math no one runs before signing the term sheet.
Founder Mode or Sell May 15, 2026 If you own a business and you don't want to fight, sell now. AI is coming for you either way.
How a $5 cup of coffee becomes $1.50 May 11, 2026 The deflationary case for humanoid robots, one latte at a time.
My Customers Don't Want to Talk to AI May 9, 2026 Maybe today. But you're answering the wrong question.
The Human Touch Is Not Going to Save Your Job From AI May 8, 2026 Every profession is telling me the same thing. They can't all be right.
Your Apps Are About to Disappear April 1, 2026 The fastest way to understand what AI will disrupt next
I Built an AI Team. Then Realized I Wasn’t Needed. March 30, 2026 I used AI to build a product, then watched it manage the work. I’m not sure where that leaves me.
Who Really Disrupts? October 10, 2025 Disruption usually comes from the outside. Here’s what to do if you’re on the inside.
What are your upsells? October 3, 2025 Most business owners work way too hard to get a new customer — and then stop at the first sale.
Is Your Customer Acquisition a Gumball Machine? October 2, 2025 The test of a real system is simple: put something in, get something out—every time.
Disruption Isn’t Luck. It’s a Formula. September 30, 2025 How one lawn care entrepreneur uncovered a repeatable framework for disruption—and how you can apply it too.
Flying Blind Without a Proforma September 29, 2025 If you wouldn’t trust a pilot in the clouds without a plan, why would you run your business that way?
Why Your Business Model Needs to Be Scalable (Even If You Don’t Plan to Scale) September 27, 2025 The secret to freedom isn’t growth—it’s structuring your business so it runs profitably, with or without you.
Why Second-Time Entrepreneurs Obsess Over Distribution September 25, 2025 The hard truth: great products rarely win on their own—distribution is what makes or breaks a business.
The Reciprocity Hack Every Business Owner Should Know September 23, 2025 The overlooked sales strategy that flips pennies into dollars.
Too Many Choices Is Killing Your Sales September 20, 2025 The counterintuitive science of selling more by offering less
AI is Quietly Killing Your Next Fundraise September 10, 2025 Don’t let AI misread your pitch—one OCR error could cost you the deal.
Why 10X Isn’t Enough for VCs September 5, 2025 What every entrepreneur needs to know about VC return expectations before raising money
Drill Baby Drill: The Boring Secret to Scaling a Business September 1, 2025 Stop chasing shiny objects—double down on what’s already working and watch your results multiply.
Why I Rarely Invest in Private Asset Classes August 27, 2025 From real estate to crypto, here’s why I now treat private deals as gambles, not investments.
Founder Vesting is Critical August 13, 2025 How a Missing Founder Vesting Agreement Cost Us 11 Years and Over $100K in Interest
Stop Betting the Farm on a “One Last Push” August 5, 2025 Why risking your last dollar on marketing, sales, or ads is the fastest way to sink your business—and how to test smarter instead.
The 50% Rule for Staying Sane in Business July 29, 2025 Why founders should dial down their highs and lows to protect themselves and their team.
Subtract to Multiply July 22, 2025 How narrowing your focus can boost revenue, profits, and referrals overnight
Small Tweaks Won’t Save a Sinking Ship July 15, 2025 I’m always amazed at how many struggling businesses I speak with. After laying out exactly how bad things are, I check back a couple weeks later and f…
Stop Planning. Start Testing. July 8, 2025 The 24-Hour Test That Can Save You Years of Work and Thousands of Dollars
Step Aside and Let Someone Better Lead July 5, 2025 Why Letting Go Could Be the Best Move You Ever Make