11 Signs To Predict If a Venture Investment Will or Won’t Work Out

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Q: What was your failed investment experience and where will you never invest funds again? Why?

I’ve made about 30 material investments. More on them here. Most have been successful, but of course not all have and I’ve been reflecting on the ones that didn’t, because they still had attractive elements when I invested.

My learnings:

What Works — That You Might Think Wouldn’t Work:

High employee/VP churn. You’d think turning over lots of VPs would impact growth — and it does. But some CEOs get through this as long as they are super committed to bringing in the next group of VPs. This can be especially common during hyper growth.
Solo founder, too many founders, co-CEOs. Solo founders can work (Zoom proves this). 5+ cofounders can work (I think of that as too many cooks, but now I see it can work). Co-CEOs can work, even though many investors think this is a flag and confusing. It works for Atlassian. It works for others, too.
Taking a long time to get to $1m-$2m ARR. I used to think if you didn’t get to Initial Traction fast enough, the team would burn out. But now I’ve learned that’s not always the case. Some of my best investments had zero revenue the first 2 years or even longer.
Cofounder conflict. I hate to see it, and personally, it held me back. But now I’ve seen many unicorns make it even with significant cofounder conflict in the early and middle days. Some of the best CEOs just push through it, one way or another.

Signs, With Hindsight, Of An Investment That Probably Won’t Work Out:

CEO hides things and/or is misleading. If the metrics don’t make sense, don’t invest. I can think of one exception that is a unicorn now, but otherwise, if the metrics are a bit baloney (e.g., claiming bookings are ARR, or using Quarterly MRR, or claiming team members are full-time that aren’t) … then pass.
If a CEO surprises you with things, do not invest. Hiding the ball I’ve seen 100% of the time leads to a mediocre outcome. Not always a failure, but always a mediocre outcome. This is really just the prior point amplified. The best CEOs are direct with the good, the bad and the ugly. At least by the second meeting.
Great CEO But Mediocre CTO. Sometimes, you can grow quickly at $1m-$2m+ ARR even with a mediocre CTO. Because that one 10x feature might be enough up to that point. But then … things get complicated. You have to scale, and add 10x the workflows. A mediocre CTO can’t keep up. These ones, even with a great CEO, hit a wall somewhere. It may be as late as $10m-$15m ARR, but somewhere.

Things That Are Super Risky You Might Not Think Are:. These are flags of likely issues to come, but they aren’t dispositive:

Taking the First VC Money Offered. The best CEOs take their time. The ones that immediately take the first Series A term sheet offered out of a bit of panic, I’ve seen that decreases the odds of success.
Secondary Liquidity Too Early. Selling some founders shares later, as the valuation passes $100m, makes a ton of sense. It helps you go long as a founder. I should have done it. But selling too early, at too low a valuation, is a risky sign the founders don’t 100% believe. This isn’t 100% correlated to failure, but there is a strong correlation here in my experience. It also can lead to substantial co-founder conflict down the road when an underperforming co-founder expects more and more of their stock to be cashed out.
A Burn Rate Even a Smidge Higher Than Normal. This is super risky — because it only grows from there. A burn rate that is even 30%-40% higher than similar companies is a flag. It’s a flag the burn rate will continue to expand at this rate. For me, any start-up that has burned more than say $3m on the way to $1m+ in ARR, that’s too much. That they need to burn too much for each new $1 they bring in. The meta-learning is more money makes it worse. They ratchet up the burn, and then burn even more than similarly situated companies. Even a slightly-higher-than-normal burn rate compounds. Into a too-high burn rate.