Non-obvious learnings in launching current startup, after co-founding 2 startups that were acquired and 1 IPO

I posted on here before when we first launched, I wanted to update you guys on some of the learnings we’ve had.

I feel compelled to share this. I'm addicted to building products people want to use. Most people think that once you have a few wins under your belt, it's easy sailing for the next startup. I think that's only partly true. Here's some context and what I think of as non-obvious learnings. I built my last venture-funded startup to $18M in revenue a year and was acquired. We then took the acquirer public (NYSE: TRMR). I'm now back building my next startup Cyclops.io.

Team-building - This gets easier, as you know who the good people are at early stages and who you have chemistry with. However, if you work with the same people you have been successful with, the strengths of having the flow and chemistry sometimes might translate into the weakness of not being paranoid. You don’t want to be stuck on a certain wavelength of thinking and not add fresh blood into key conversations. I have seen this occasionally and it’s subtle. This way of thinking brought us success before, so it’ll work again this time. Not necessarily true.

Finding Product / Market fit - Experience and calcified assumptions can be a bad thing. You tend to think less disruptively if you are not as wide-eyed. One of the learnings we had early on when starting the current company was to find a space with problems we were intimately familiar with as users and passionate about solving, but not a domain we knew much about in terms of how things were done. This way, we didn't feel shackled by assumptions. Our pain point for remote collaboration. We weren't as productive as we wanted to be on existing video conferencing systems. A lot of innovation was in supporting as many users as possible in a session. We thought for teams looking to get things done, there was little innovation in amplifying team's productivity. So we built Cyclops.io, a video conferencing platform with productivity tools on top. What was a bit non-obvious was that we have to reset ourselves to have a lot of humility in testing assumptions and re-building our network of contacts.

Fund-raising - This gets easier too since we are credible entrepreneurs with wins. That said, the surprising thing is sometimes we get questions around if we were too experienced and not wide-eyed enough. Raising too much money can turn into a downward spiral as you might be tempted to spend too much too quickly and lose the discipline that comes with a small budget.

Distribution Model - This was probably the biggest learning. Our current business was very different than our last one. How we get to customers is extremely different. The times have also changed - how users buy certain types of software have also started to transition from field sales to inside sales and self-service. Getting up to speed here took time. We used to have a field sales driven organization that was expensive to build. Now, we are innovating on self-service to make cost of sales much lower.

Mindset - This is probably the most important. Thematically, you just have to have a scrappy mindset again. You have to fight every dollar spent and get every dollar in. Question every assumption. Vet every investor and potential hire.

Overall, there’s a little grain of truth to the old line “the more experience you have, the less you know”, especially in a fast-changing segment. You just gotta keep your head steady and assume nothing.

Submitted August 02, 2017 at 09:34PM by joaopedroo http://ift.tt/2howR3z via TikTokTikk