Follow Gregory Scott Henson

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

The last decade of SaaS made you do the work. The next decade does the work for you. The average knowledge worker switches between apps 1,200 times a day. That is not productivity. That is a tax we all quietly agreed to pay. We built the last decade of SaaS by going deep, not wide. Specialize. Reduce scope. Sell to procurement. Configure with an admin. Every product solved one slice and handed the user a new login. The result sits on every sales rep's screen right now. Fiftee

Most companies treat AI agents like software. The winners treat them like staff—giving each agent an owner, a defined outcome, and the same honest feedback they give their human team.

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

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

After watching dozens of hours of AI tutorials and checking what people are actually recommending in 2026, here is my list of ten channels that actually teach you something useful. YouTube has quietly become the best place to learn artificial intelligence without spending thousands on courses or going back to school. You can find everything from mathematical breakdowns to practical coding tutorials, and most of it is actually free. The problem is not finding content but findi

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.

Most people talk about AI assistants like Claude Cowork as productivity tools for work. Organizing spreadsheets. Drafting emails. Summarizing documents. All useful. But I think people are missing the bigger opportunity. Because the same operational work that runs a business also exists in your personal life. And AI is incredibly good at operations. For the past few weeks I’ve been using Claude Cowork not just for my companies, but for what I call the other 16 hours of the day

AI is coming for a huge share of human work. And most people, including many leaders, are not prepared for what that actually means. Behind closed doors, the conversation about AI and labor sounds very different from the public messaging. Public messaging: “AI will remove boring work. Humans will be more creative. More fulfilled.” Private framing, as Tristan Harris (former Google design ethicist) put it: “AI represents productivity without the tax of human labor.” Huma

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

I’ve been testing Anthropic’s new desktop agent, Claude Cowork. It’s the first AI tool I’ve used that actually feels like delegating work instead of chatting with software. A few weeks ago I gave Claude access to a test folder called CoworkDownloads (300+ random files, duplicate PDFs, screenshots, receipts, and “Image.png” chaos). I told it: organize this, rename everything clearly, flag duplicates, and create a structure that makes sense. I left for coffee. Twelve minutes la

After watching dozens of early-stage SaaS companies struggle to gain traction, a few clear marketing patterns stood out. These weren’t subtle mistakes. They were repeatable, expensive, and often fatal. While building my own B2B SaaS, I deliberately avoided those traps. Here are the three marketing growth lessons that mattered most, not theory, but practices that actually moved things forward. Failure 1: They Built First, Marketed Later One of the most common SaaS mistakes is

Building a SaaS company looks glamorous from the outside. In reality, most days feel like controlled chaos: tiny wins, loud failures, and a constant battle between confidence and doubt. As the founder of SocialPost.ai, I’ve stopped chasing hacks, frameworks, and overnight success stories. Instead, I’ve narrowed my focus to four growth factors that consistently compound across stages, funding levels, and market conditions. I’m sharing these openly as part of building in public