Newsletter

After my last exit, I found myself drawn to coaching. I wanted to help founders avoid the struggles I’d faced while building my businesses. But there was a problem. Every time I introduced myself as a coach, I saw that look – “Oh, one more coach.” I was being lumped in with many others. And

Most founders have a solid product. But they can’t seem to close deals fast enough. The problem isn’t the product. It’s the offer. The $100k Question Would you pay $10K today if I guaranteed you $100K in 90 days? You’d say yes in a heartbeat, right? That’s an irresistible offer in its purest form. Your

“We need you to stay for a year after acquisition.” That sentence is every founder’s exit nightmare. When I sold my tech company, I heard those exact words. Buyers were nervous—what if my business collapsed without me? But something unexpected happened. During 80 days of intense due diligence, my post-sale commitment shrank from 1 year

In 2011, JCPenney made a bold move. They hired Ron Johnson, the mastermind behind Apple’s retail success. JCPenney, a 120-year-old American retail chain with over 800 stores, was struggling with declining sales and an outdated brand. Shoppers saw it as a discount retailer, dependent on coupons and sales to drive foot traffic. Meanwhile, Ron had

Last week, I wrote about the biggest trap founders find themselves in: Waiting for more time.  The responses I received were overwhelming – this challenge clearly struck a chord with many of you.  Turns out, the real problem isn’t time. It’s staying trapped “in” the business. Trapped in My Own Business If you’re feeling trapped

Just last month, three different founders came to me. Each had everything needed for growth: Clear vision. Great potential. Ready to invest. But they all ended our conversations the same way: “I’ll come back when I have more time.” After hundreds of conversations with founders, here’s the painful truth I’ve discovered:  These talented entrepreneurs are

📌 Note: This is Part 3 of our Operating Model series. For best results, read Part 1 and Part 2 first. They lay the foundation for this implementation guide. Over the last two weeks, we explored: Why org charts can’t keep work flowing (Part 1) The 4 elements that make up an Operating Model (Part

Last week, we explored why work gets stuck even with a perfect org chart (read Part 1 here). If you did the exercise, you probably noticed that the same bottlenecks appears across your company. I have been here. As my company grew, I found myself in endless meetings, constantly being pulled into decisions, and feeling

What used to take 2 hours now takes 5. What used to be a quick decision now needs 3 meetings. What used to be instantly clear now gets “stuck in communication.” You’ve probably tried everything: better tools, more processes, and endless documentation. And when those didn’t work, you tried reorganizing your org chart — moving

The ancient banyan tree towered above me, its aerial roots reaching toward earth like fingers of time. Beside it lay its fallen brother. Once mighty. Now, returning to soil. Nature’s oldest lesson was playing out before me. Everything is temporary. In 7 days, I’ve walked over 60 kilometers through Singapore and Bali. Through manicured gardens

Micromanaging? It kills trust. But ignoring problems? That kills your business. I’ve been coaching dozens of founders over the past 18 months. Every time they avoid stepping in, small issues grow into big problems.  When operational issues or performance drops, the solution is obvious: The founder needs to step in. Yet, almost every time I