Follow Gregory Scott Henson

A founder texted me last week at 11 PM. He was frustrated, said his startup had “a great product, no customers, and zero idea where to start.” Classic. We hopped on a call the next morning. His pitch deck had 14 slides on positioning. His CRM had three contacts. Three. I told him to close the deck and open his phone. That’s where his first 100 customers actually live. The Niche Conversation Misses the Point Every founder eventually gets the “narrow your niche” lecture. It’s g

You crushed the pitch. The investor leaned in. Asked the right questions. Told you they were excited. You walked out already mentally spending the money. A week later, they passed. No real reason. Just a polite no. Here is what nobody tells you. Investors do not fund startups. They fund people. And before a single wire hits your account, they are running two evaluations on you. I call them The Room Test and The Backstage Test. I have sat across from hundreds of investors. I h

A founder called me last week, ready to shut his company down. He had built a software product. He was doing the work. Sending the emails, making the calls, taking every meeting he could get on the calendar. He just wasn't getting the result he wanted. "Greg, I'm lucky if one out of fifty people I reach out to actually buys," he said. "At this rate, I'm wondering if I should just shut the whole thing down. Maybe the idea is bad." I laughed. "A 2% conversion from cold outreach

I watched a founder blow a room full of investors last month. Beautiful deck. Polished slides. Clear problem, clean market size, “rockstar team” in the upper right corner. He had rehearsed the handoff between slides. He even had a clever transition into the TAM/SAM/SOM breakdown. His product was “revolutionizing multi-cloud data governance.” Whatever that means. During Q&A, I asked one question. “What have you done to get customers?” The confidence left the room. Then came th