The AI Gold Rush and the Erosion of the Founder/Investor Relationship

The AI Gold Rush and the Erosion of the Founder/Investor Relationship

Image by Gerd Altmann from Pixabay

Jake Crowley of Crowley-Capital spoke at our Online Investor Insights last week and focused, in part, on how transactional the investment process has become. It wasn’t all that long ago that, when  when he was our investor guest at the event, David Arcara of Laconia Capital , asked, “How often do you hear that getting into bed with an investor is like a marriage? It’s not. If a marriage goes south, you can get a divorce. When you get into bed with an investor, there is no divorce. You are stuck with that investor for the life of your company.” He advised that founders get to know the investors before signing on the dotted line, and to do due diligence on them as well.

”When you meet a founder for the first time and they tell you they want a term sheet by Friday, I always respond with, “Really? Aren’t you at least mildly curious if I’m a complete A-hole or not?” commented Tom Lazay in a LinkedIn piece.

Times have changed and on the heels of Jake’s remarks, Micah Rosenbloom of Founder Collective made the same observation and offered his insights in LinkedIn post, commenting that “VC used to be a marriage between an investor and a founder. Now, for some, it’s a series of one-night stands;-)

“Loyalty seems to be at an all-time low in venture right now. Everyone feels a bit more transactional. A bit more short-term. A bit more… mercenary.

“I hope it’s just Gold Rush behavior…I’m starting to wonder if the social contract in venture is eroding on both sides of the table.”

True that, in some cases, from what we’ve observed, and precisely how heated is the space? We recently learned of a startup that raised a $20M pre-seed round from a well-known VC based on a back-of-the-napkin idea presented by an Adam Neumann-level charismatic founder. What’s that expression: the more things change…It seems that even in the AI Era, some things never change. Time will tell.

There’s no doubt that the AI Era has contributed to, if not accelerate,d bad behavior, but that’s not where it started. It began when young founders and their C suite employees who were (often) acquired with outsized exits decided that they, too, could now be investors. It’s not that they earned their stripes by taking analyst spots at VC firms or even became LPs in more established funds in order to learn the process, meaning what to look for in a company and/or founder. Some turned to angel investing, usually in verticals with which they were familiar. Others put up their own shingle and voila, with no background in either investing or finance. they were VCs.

“But it’s not just VCs. Founders are behaving differently too,” Rosenbloom continued. “More and more, startups feel like 12-18 month experiments. If it doesn’t hit quickly, people move on. Less loyalty to the original idea. Less loyalty to co-founders and teams (more founder acquihires). Less loyalty to the investors who took the early risk. I’m seeing more founders with 2-3 companies behind them in just a few years.”

While we do live in a short attention span world, we’ve said it before: starting a company is easy. Building one is hard. Everyone pivots, and that’s when frustration, depression, tough decisions and a lot of hard work come in. It’s also what separates the true entrepreneurs from the dilettantes. And since the overall timeline has been condensed, or as Rosenbloom put it, “A 10-year asset class operating in markets that now reset every 12-24 months,” the dilettantes bail and the true believers tough it out and hopefully, have investors who still understand the long game.

“In my experience Investors often ask founders to focus, but also push for pivots toward whatever narrative the market rewards at the moment. That creates a strange incentive: if capital behaves opportunistically, founders eventually start behaving the same way. I wonder whether the real issue isn’t loyalty disappearing, but that the system rewards short cycles more than long conviction,” suggested Miles Litteral in the comments.

“Also, both entrepreneurs and VCs that act in this short minded mentality threaten their own long term success. Acting with integrity is so important,” offered David Brown.

“Regardless, I still think there’s alpha in the opposite approach. Things often go wrong before they go right, especially at seed. One of the fund-returners from our Fund I back in 2009 struggled for years to crack a category that didn’t exist yet and was on the brink of shutting down. But the founder refused to jump ship. So did FC. That company is now the most valuable in its category,” Rosenbloom noted.

In fact, we worked with a startup that was on the brink of collapse when the founder did a major pivot that was basically a reinvention of the company, resulting in a billion dollar plus exit.

Get to know your investors on a human level, Crowley advised. After all, getting into bed with an investor is a relationship, not a transaction, and when the going get touch – and we promised you that it absolutely will – you may need your investors’ help. Which is why it’s also critical to choose an investor who is familiar with your space, aka, choose ‘smart money.’ They may be able to help on many levels and do make sure to communicate when you first encounter those roadblocks, not after you’ve driven off the cliff. Also critical is choosing the right advisors/board members and ever wonder why they’re also considering something of your steering committee?

And there you have it.

One final suggestion, as we know founders tend to seek out investors who focus on their space and neglect to do a deeper dive to see if there is a similar company to the founder’s already in the firm’s portfolio. We’re not talking about a possible symbiotic relationship between the two: we mean that yours is potentially a direct competitor to that portfolio company, and the investors might take the meeting simply to see what you’re doing that their current investment might benefit from. In other words, they have no intention of investing but are happy to appropriate your super power.

So let’s be careful out there and do keep in mind that getting into bed with an investor is a marriage, but as far as we know, to date, they don’t appear to be polyamorous or bigamists. Onward and forward.

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