What attracted you to invest in Automile?

Every investor takes different types of risks.

Risks I won’t take:

  • CEO that isn’t great & going for it.
  • CEO that isn’t better than me.
  • CEO I wouldn’t work for.
  • Great founder, but she isn’t the CEO.
  • Product-market fit risk. I won’t invest unless you have at least 10 Unaffiliated Customers.
  • A space where getting The Next Investor feels hard even if the company hits its growth plan for next 12–18 months.
  • Not intuitively clear to me how company can get to $300m ARR, in theory.
  • Founders too tired.
  • Founders don’t like sales.
  • Crappy software that still has a lot of traction.

but

Risks I will take:

  • Founder new to U.S., or coming to U.S.
  • Founder has no network in U.S. and maybe even knows no one here.
  • No management team at all, no idea — yet — where to find one.
  • First-time CEO, even first-job CEO.
  • Looks like there are 100 competitors — from the outside.
  • Looks like the product isn’t innovative — from the outside.
  • Founders don’t understand sales, or marketing.
  • I don’t need social proof or co-investors. I don’t care who else has invested, if anyone. I can deliver the next round investor — if you hit the plan.

Every investor is different.

So when I finally was lucky enough to invest in Automile.com, the company had a great CEO and founders with product-market fit who was really going for it. In a market that, by growing it, could easily get to $300m+ in ARR. Bonus: super-happy customers, and net-negative churn with SMBs (which is rare).

Risks I took: CEO had just come from Sweden, a lot of revenue then was still in Europe (>50% in U.S. today), no management team, product superficially looked similar to a lot of other high-profile B2C and adjacent investments.

Fast forward today, we’ve almost quadrupled in less than a year, we have a great management team, a best-in-class product starting to dominate its core market segment, revenue that is accelerating, Salesforce as a strategic investor, and a majority of revenue in U.S.

But other investors, many far better than me, take different risks.

View original question on quora

Published on March 23, 2017

Pin It on Pinterest

Share This