In 2010, our seed raise was a breeze. We were young, arrogant, and deeply technical — a recipe for an oversubscribed round in 2010. We confidently handwaved away questions like "how will you get customers?" and spent most of our time building product.

In 2011 we started getting approached by Sand Hill funds to talk about a potential Series A, in the way that Sand Hill funds approach startups: They're excited, they're ready to fund, but actually they just want to learn more. Suddenly, we found ourselves fundraising again.

We were building an enterprise product but still didn't really have any paying customers (we had some free users). This time around my handwaving didn't work as well. Some investors politely nodded and then passed, but one AAA Sand Hill partner meeting went particularly poorly.

My first two meetings with this fund went well, and so I found myself in a full partner Monday meeting. It was a complete disaster. Once again, I was unprepared for the "how will you get customers?" questions, except this time the partner wouldn't let me off the hook.

We had users, and we even had some users who loved the product. But, ultimately, we were building a B2B/Enterprise product, and in 2010/2011 I knew nothing about sales and go to market. I made the naive mistake of believing that if we build it, they will come.

The partner and I sparred back and forth for a few minutes, until he suddenly interrupted me and said: "Yuri, hope isn't a strategy." He then got up and left the room, leaving me to awkwardly finish the final 20 min of the meeting with his other partners.

I left the meeting shell-shocked. Got into my Ford Fiesta, and just drove aimlessly west on Sand Hill towards Halfmoon Bay. Eventually I parked my car, composed myself and drove back to the office.

I spent a lot of time being offended and angry at how that partner behaved in that meeting. And while I continue to think he could have acted nicer — he was also right. We *didn't* have a plan on how to get customers at that point, and we weren't ready to raise our next round.

I think of this incident every demo day cycle when I meet founders who are crushing their raises. I remember what that was like, and I also remember what followed. Don't be like me — have a plan. And, if you're doing a B2B/Enterprise business, learn to sell ASAP🙂

@yuris @ValaAfshar Thanks for sharing. 🙂

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@yuris Sadly, in the current environment, many founders don’t get that lesson that you got 😞

@yuris Ikr! This makes a lot of sense when I look at this lesson from my journey. Product building is an iterative process and can run parallely while sales are happening.

@yuris @GregKeal

@yuris Thanks for sharing such an awesome insight. Loved it.

@yuris Thanks for sharing! If he had acted nicer, you might not have heard the message you needed to hear. Seems what you did with it paid off well.

@yuris If you look around the room and don’t see a salesperson, it’s you 😁 (paraphrased from a Peter Theil book)