I have spent more than twenty years around investing — most of it managing portfolios in traditional asset management — and I now spend my days doing two things at once: partnering with AI management teams through Fifth Turn Capital and building AI products myself at Flowlinx. That dual seat shapes how I read a company. So if you are an owner or operator wondering what an investor like me is actually looking for, this note is written directly to you. The short answer: I am not underwriting a spreadsheet alone. I am underwriting a small number of things I believe will still matter in three years — whether the technology is real, whether the market is real, and whether the team is the one to keep building it.
AI at the core, not bolted on
The first question I ask is simple: if you removed the AI, would there still be a company? For the companies we partner with, the answer is no — intelligence is the product, not a feature stapled onto a familiar workflow. That does not mean you need a novel model or a research lab. It means the hard, valuable part of what you are building is inseparable from the AI itself, and you understand it well enough to explain where it is strong, where it breaks, and why that gap is closing. I am far more persuaded by a leader who can talk honestly about the limits of their approach than by a polished demo that avoids them. Demos are easy now. Conviction about the underlying technology — earned by actually building with it — is not.
A real market
The most impressive technology in the world does not become a business until someone needs it badly enough to pay for it. We invest in established companies, so I expect revenue — but more than the number itself, I expect evidence that you have found a real problem worth real money — a customer whose day is genuinely worse without you. Show me that you have talked to those people, that you understand what they do today instead, and why your product is not just better but better enough to switch. Markets forgive a rough first product. They rarely forgive a product that solves a problem nobody urgently has.
An exceptional team
In an established company, the team is most of the decision. I am looking for leaders who are technical or close to it, resourceful under constraint, and unusually clear about the problem they have chosen. I pay attention to how fast you learn, how you handle a question you cannot yet answer, and whether you have the resolve to keep building when the work is unglamorous — because much of it will be.
- •AI at the core — The technology is the product. You understand its edges as well as its strengths.
- •A real market — A concrete customer with an urgent problem, not a demo in search of a use.
- •An exceptional team — Leaders who learn fast, ship, and can carry the unglamorous middle.
On choosing a partner
A few honest things about the partnership itself. First, organize around a milestone, not a headline number — decide what you need to prove next, structure the deal to get you there with room to spare, and be able to say out loud what 'there' looks like. Second, aim for the capital and structure that lets you hit that milestone without straining the company; over-reaching early can lock in expectations you then have to grow into. Third, treat the process as a filter, not a popularity contest. You are choosing a partner for the next decade, and the investors who ask the sharpest, most uncomfortable questions are often the ones worth having. And do not let the search for the perfect partner become an excuse to stop building. The best leverage you will ever have is a product that is quietly getting better every week you are in conversation with us.
What a good investor relationship looks like
Once the deal closes, the money is the least interesting thing on the table. What you actually want from an investor is honest counsel, fast answers, and someone who has sat in the operator's chair and shipped real product. We keep our portfolio focused for exactly that reason — so a management team can call and get a real conversation, not a name on a cap table who resurfaces at board time. A good relationship is candid in both directions. You should feel able to bring us the bad news early, and you should expect us to disagree with you plainly when we think you are wrong — and then get behind the decision you make.
If you are building, reach out
None of this requires you to have it all figured out. The leaders we most want to meet run real businesses, are honest about what is unfinished, and are completely serious about the problem in front of them. If that is you, do not wait until everything looks polished — the most useful conversations tend to happen well before then. You can learn more about me and how I work, and if you are building an AI-native company, I would genuinely like to hear from you.
