People ask me which AI tools I use across my companies more than almost any other question right now. And I get why - the landscape is overwhelming, there are hundreds of tools being marketed to entrepreneurs, and most of them are designed to look impressive in a demo and disappoint in actual use. So here's what I've actually learned going through this across a portfolio of twelve companies: the specific tool matters a lot less than most people think. What matters is the filter you use to evaluate every tool before it enters your operation.
The Filter Every Tool Goes Through
Before I add any AI tool to any of my companies, it has to answer yes to at least one of four questions. Does it directly reduce a cost that's currently showing up on my books? Does it help my team produce more without burning them out? Does it help me reach more of the right people with less time and money? Does it give me better information faster so I can make better decisions?
If the answer is no to all four, I don't use it. Doesn't matter how impressive it looks. Doesn't matter what the demo showed. Doesn't matter if somebody I respect told me I had to have it. A tool that can't answer yes to at least one of those questions is a distraction dressed up as productivity, right?
Now, most entrepreneurs I talk to have the opposite problem. They've added tools without running any filter at all. They're paying for subscriptions they barely use, their teams are confused about which tool to use for what, and the AI overhead is creating more complexity than it's eliminating. That's a guarantee of waste - and it happens because they went looking for tools before they got clear on the problems.
Where AI Creates the Most Leverage in My Companies
I look at all of my companies through four pillars: Revenue, Reach, Relationships, and Organization. And the area where I've gotten the most return from AI is Organization - the internal systems, processes, and operations that run the business behind the scenes.
Research that used to require most of a day from a team member now gets done in under an hour. Competitive analysis that used to require an outside vendor and a week of waiting gets produced on demand. First drafts of internal documents, summaries of data, initial structures for anything that requires thinking and writing - all of that gets handled by AI before a human touches it. That compression of time and cost compounds, right? And over twelve companies, it adds up to something real.
Reach is the second area where AI creates significant return. If you're creating content - articles, emails, video scripts, social media - AI can compress your production timeline significantly. But I want to be specific about this because most people get it wrong. AI handles the research, the structure, the first draft, and the editing pass. What comes from me - the stories, the perspective, the specific things I've learned building and investing in companies for thirty years - that has to come from me. Your core competency as an entrepreneur is not something you outsource to a tool. You use AI to scale what you already know, not to substitute for knowing it.
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Here's what I've learned that nobody talks about: the specific tool matters a lot less than the quality of direction you give it. And what matters even more than that is whether the process you're plugging it into is actually solid.
I've watched entrepreneurs get excited about the same tool I use, plug it into their operation, and get nothing out of it - while we're getting real return on the same tool. The difference is almost never in the tool. It's in the process the tool is plugged into, right? A weak process accelerated by AI is still a weak process. A strong process accelerated by AI becomes a real competitive advantage.
The other thing I'll say: don't build your operation around any one platform. Build the process first. Document it. Make sure it works. Then plug in whatever AI handles that process best right now. Because the landscape changes - what's the best option today may not be the best option next year. But your documented, working process? That outlives any platform. That's what you're actually building when you build the business right.
The entrepreneur who has mastered three AI tools and integrated them into working processes is running circles around the one who has subscriptions to twenty tools and hasn't committed to any of them.
What I Stopped Using (And Why)
I've cancelled more AI subscriptions than I've kept. Most of them were tools I tested because they looked impressive in a demo, or because someone told me I had to have them, or because I thought they were solving a problem that wasn't actually a constraint in my business.
The pattern was the same every single time: I added the tool before I was clear on the specific problem I needed it to solve. That's a guarantee of waste. AI tools don't create clarity. You bring the clarity. The tool executes. If you can't name the specific process the tool is running and the specific output it's producing, you don't need that tool yet.
So if you're currently paying for AI tools and not seeing a clear return, go back to first principles. What specific process is this tool supposed to improve? Is that process currently working? If not, fix the process first. If yes, is the tool actually making it better? If not, either it's not the right tool or you're not directing it well enough. Either one gets resolved faster than most people think - once you're willing to ask the question directly.
The One Thing That Separates Real Results From Expensive Experiments
The entrepreneurs getting the most out of AI right now are not the ones with the most tools. They're the ones who learned how to direct AI like they direct a talented team member - with specific expectations, clear outputs, and a willingness to iterate until the standard is met.
That's not a technology skill. That's an operator skill. And if you can build companies, lead teams, and make decisions under pressure - you already have it. You just have to apply it to AI the same way you apply it to everything else.
The North Star I use across all of my companies hasn't changed: focus on the few key actions that move the needle the most. That applies to AI just like it applies to every other decision. Keep the stack lean. Go deep on what's working. And don't let the noise of what's new pull you away from the fundamentals that actually build a business.
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