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Three deals, five months, all dead inside the same week. The founder telling me this sells enterprise software with sales cycles long enough to require somewhere between ten and ten thousand meetings. He had been working those three deals since spring. The first died because his champion took a job somewhere else, and her replacement had a preferred vendor from a previous company. The second died because the buyer got acquired and every discretionary purchase froze. The third

In 2002 I ran a company out of a one-bedroom apartment in New York. For the first nine months, I was the only employee. The motion was simple. I found companies that had been knocked flat after 9/11, and I migrated their systems for free. When they got back on their feet, they hired me to build and run their infrastructure. It worked. Revenue came in. Clients told other clients. From the outside it looked like a company. It wasn't. It was me. For almost a year, the entire go-

A founder in my Startup Kings WhatsApp group asked me for advice on promoting his startup on social media. I spend what is, for a C-suite exec, an unhealthy amount of time thinking about content strategy. So I was happy to help. I walked him through what a real strategy looks like. Identifying content his target audience actually cares about. Building a production schedule so he posts consistently instead of sporadically. The AI tools that speed it up. Learning editing softw

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

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

A founder I know built something great. I used it and sent it to a few people I trust. Every single person said the same thing: “This is exactly what I needed.” A few months later, he shut it down. I asked what happened. “We couldn’t get it to travel.” That word stuck with me. Because most startups don’t fail because the product is bad. They fail because it never leaves the room it was built in. We talk a lot about product-market fit like it’s the finish line. After twenty ye

I sat through a pitch competition recently and saw the same mistake over and over again. Founders walked on stage, clicked to their first slide, and started performing. You could tell they had practiced. The transitions were smooth, the lines were polished, and everything sounded impressive. And yet nothing landed. Every pitch sounded the same. We are redefining the future of something. We are democratizing access to something. We are revolutionizing the way something works.

Yesterday, I sat down with seven founders back-to-back. Different ideas, different industries, different stages. Same exact mistake. I’ve seen this pattern for over 20 years, whether it was mentoring founders, scaling Henson Group from a one-bedroom apartment after 9/11, or advising startups today. It doesn’t change. Everyone starts with what they want to build. Almost no one starts with who they’re building for. Each founder walked me through their product. Features, roadmap

Most founders think startups begin with a product. Someone has an idea. They design the technology. They build the platform. Then they launch and hope customers show up. It sounds logical. But after building companies, investing in startups, and watching thousands of founders attempt the same journey, I have learned something that surprises many first-time entrepreneurs. The hardest part of a startup is almost never building the product. The hardest part is getting customers.

I spent six months building my first “big” digital product in a dark room, fueled by caffeine and a “perfect” business plan. I didn’t talk to a single soul because I was terrified someone would steal my “genius” idea. When I finally launched, the only sound was the chirping of crickets and the notification of my Shopify subscription renewing. I had executed a flawless plan for a product nobody wanted. Steve Blank and Bob Dorf’s The Startup Owner’s Manual is the 600-page “bibl

Most startups don’t fail because of bad ideas—they fail because they build too soon. Before you code, validate. Talk to real customers. Launch a landing page. Test assumptions early. Build smarter, not harder. — Gregory Scott Henson | Startup Advisor | 50x Angel Investor | 20x Founder | 4X CEO