Rory O'Driscoll

AI (duh). I think in venture investing, you have to be broadly thematic without letting it entirely dominate your thinking. The reality right now is that the major mega trend is the move to add intelligence to software and the physical world, and most investments will be oriented around that. 

However, I have also learned to be open-minded. There are no hard-and-fast rules in investing, except that you have to make money for your investors. I’ve made money in client-server land, then Cloud and SaaS in the last two decades. Now it's AI, but if something is working, exciting, and not AI, I am absolutely open to that. 

I think the pace of change is what makes this different from anything in my prior experience. From a technical perspective, the capabilities of AI are beyond interesting in terms of how much the market is changing. In AI, you have to be comfortable with a large amount of product and tech change through the entire lifecycle. In prior days, there wasn’t as much product fluidity. You’d start with a market and an idea, nail product-market fit, then sell the hell out of it. Now, you have to stay on offense on product and underlying technology from seed to IPO and beyond. I don’t think that’s going away.

I don’t look for any particular profile in founders. I believe (and the data shows) that all types of founders can make it. I’ve invested in 22-year-olds and 60-year-olds, and both have had wildly successful outcomes. There is no one way to succeed.

What is true is that what a founder has achieved so far in their career and in the company (especially if “founder” is their first job) is by far the best "tell" as to what they are likely to achieve going forward.

From a skills perspective, I have observed that with self-knowledge and a willingness to get help, there are no fatal founder skill gaps. But without that willingness to get help, founders are doomed to fail.

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I like structure. Walk me through a presentation. Don’t make me guess at what the important things are. Tell me and then I can respond. I am also known for being an interrupter, but hopefully not in a rude way. There’s just no point in spending time on the things we agree on. You have a belief that caused you to found this company, and I am trying to figure out if I believe it, too. We’re all trying to make it work here. So, let’s get to the two or three things that matter.

For different investments you can weigh attributes of opportunities differently, but every investment should have at its core a founder with a vision for something exciting that should exist in the world that does not exist today and is now possible (or nearly possible). That vision should be exciting to me, as if I invest I am going to be spending ten years working with the founder to help make it happen. More importantly, it should be exciting so that it can attract the employees, customers, and capital to make it possible.

I have been a board member for 30 years and 60+ investments. I actually like that part of the work the most. I think I have decent pattern recognition and a willingness to give my opinion honestly even when it is not good news. I try to be direct—founder honest, not founder friendly.

It’s always a good time to found a good business and never a good time to found a bad business.