AI Challenge Part 1: How AV Went All-In on AI

In a matter of weeks, AI technology has gone from sci-fi trope to seemingly the topic of every other business meeting and conversation. Witnessing this rapid transformation, many of us probably experienced a case of the 3 AMs. If you don’t know what I mean, then you haven’t been a founder or CEO.

I’ve been through similar technological shifts before — the microcomputer, the internet, the smartphone — though those were dismissed early on as toys or niche solutions. That’s not the case with AI. Almost daily, AI bounces between being the savior of our failed education and healthcare systems to posing an existential threat.

That high-level talk is fine, but my priority was to determine how this tech would impact my company, a retail venture capital firm. I needed to decide how my company should approach AI. Should I wait and see? Cautiously experiment? Or try something more aggressive?

I chose to go “all-in.”

Here’s my story of why I made this move and how we went about it.

The All-in Decision

So first, why did I opt to go all-in? Partly my background. As a student of Clayton Christensen, I’ve studied the power of disruption. And I’ve lived the “before and after” results of powerful technologies that simultaneously wipe out and spawn careers, companies, and whole markets.

AI is at least on this level of transformation, with the potential to be the most disruptive of all. I’ve learned — sometimes gratifyingly, sometimes painfully — you want to be on the right side of epoch-defining tech disruptions.

I care deeply about our customers, owners, teammates, and portfolio companies (including many in the AI sector). It’s my job to ensure we’re on the right side of this historical trade. Reflecting on my 35-year career, I realized my best decisions have been carefully considered “all-in” moves. That’s the approach I concluded I’d take regarding AI for our company, Alumni Ventures.

Another fundamental reason: I believe that AI can make a huge difference given the context of our company. In the world of venture investing, Alumni Ventures is unique in volume and complexity. We are retail VC (versus institutional), with almost 10,000 individual customers. We also invest a lot — 1,100+ portfolio companies, adding another ~300 per year. In fact, PitchBook ranks us as the third-most active VC on the planet (2022 Global League Tables). Another marker that charts our explosive growth is that we have grown from a single $1M fund in 2015 to raising over $1.2B.

All that translates into lots and lots of data to process, analyze, and use, plus many repetitive processes that need to scale. Spread that need across 50 investment professionals and ~100 support staff from various departments (engineering, finance, customer service, OOI, marketing, P&C, legal), and you can see why AI seems heaven-sent to us.

Setting a Clear Vision and Goal

Decision made, I had to rally our people. I generally believe in a barbell approach to management, which balances top-down and bottom-up approaches. And building consensus is often the best approach to align a company around a goal. But in this case, I knew the decision, goals, and plan needed to be unequivocally communicated by me.

I called an All Hands: Within 12 months, our firm would become the most AI-powered VC in the industry. The statement was ambitious, provocative, and a definite stake in the ground. My goal was to have every single person — from me to our interns — to use AI daily in meaningful ways.

In support of that message, we created several special Slack channels, plus hosted numerous brainstorming and planning sessions. We also put resources behind the drive, ensuring that everyone in the company had access to ChatGPT, tutorials, and consultants. Initially, we just wanted folks to play with AI tools.

Next, we began sharing experiments (things that worked and those that didn’t), prompt suggestions, and industry developments. Leadership also modeled use cases, offered guidelines, and cautioned folks about tool limitations and safety issues. Employees were starting to find the tools not only fun but helpful.

After getting teammates acquainted with AI tech, we wanted to home in on very practical ways it could impact daily work. Our focusing mechanism was the creation and launch of AV’s AI Challenge.

To learn more, click here to read part 2 of my op-ed, or see below to watch an overview of the competition.