From 0 to 10: Making the “right” decisions

By Ben Congleton, Chief Executive Olarker

This post is the fourth in our 10 year anniversary series. Want to catch up? Read the series intro, Olark’s origin story, and our road to a co-created culture.

A few years after graduating from YCombinator, Olark walked away from what could potentially have been a very lucrative acquisition offer.

We were in the midst of partnership discussions with a larger tech firm. In one late-stage meeting, the conversation about our technical capabilities turned into a presentation on their product vision, and I realized that our potential partners were actually interested in buying Olark.

I reacted instinctively. I told them I wasn’t selling.

As soon as the words were out of my mouth, I felt the tension rise in the room. The other company’s representatives were a little taken aback, of course, but my co-founders were truly alarmed. We hadn’t discussed the possibility of an acquisition offer, and others on our founding team were (justifiably) excited and wanted to hear them out.

I knew that many founders in my position would jump at an opportunity like this one. But I also believed strongly in Olark’s future as an independent company; I loved the culture we were building, and I felt like our product and vision were just starting to gain momentum. I knew that if we were acquired at our small size, we’d simply be absorbed, and our unique little spark would fade out in a corporate blaze.

I knew that many founders would jump at an opportunity like this one. But I also believed strongly in Olark’s future as an independent company; I loved the culture we were building, and I felt like our product and vision were just starting to gain momentum.

Over the weeks, months, and years that followed, plenty of people would second-guess that choice. And the fallout certainly wasn’t all good. Ultimately, two of our four original co-founders decided to move on from Olark, in part (though not entirely) due to disagreements around the acquisition decision. Our would-be acquirer ultimately became a competitor. And, of course, we walked away from what might have been a fairly sizable chunk of cash.

Despite all that, though, I’ve never doubted that I made the right call. I started Olark to create freedom, and I wanted to build an organization where I’d be excited to be either CEO or the next hire. Some of the things I said in that meeting were impulsive, but they were voiced from a place of uncompromising alignment with Olark’s values, and with my own.

The “right” call isn’t always what everyone else thinks. More often, it’s the decision that moves you one step closer to your vision of the world and the work you want to do in it — even if you can’t see the entire path that follows.

The “right” call moves you one step closer to your vision of the world and the work you want to do in it.

  • We went full remote. Remote work was one of our potential acquirer’s major concerns, and it almost certainly would have gone away if we’d been bought. As an independent company, we were able to go all-in on learning to hire, onboard, manage, and build culture remotely. The option to bring in the best person for every role, regardless of where they live, has been an enormous competitive advantage — and has given me the opportunity to work with amazing Olarkers from around the world.
  • We demonstrated that small companies can have a big social impact. Our remote, 35-person team made national news for our stances on mental health and unplugged vacation. We’ve set an example by starting conversations and living our values, and our stories have touched people and companies around the world.
  • We emphasized #Chill. Olark has never been a “typical” 60-hour-a-week tech startup. Bootstrapping and staying independent meant that we needed everyone to be energized for the long term — and that meant creating space for flexible work, parental leave, unplugged paid vacations, breather weeks between quarters, and laid-back time together as a team. We’ve figured out how to work sustainably, which is something far too many companies never learn.

We’ve figured out how to work sustainably, which is something far too many companies never learn.

  • We failed a lot. And we learned a lot. In declining acquisition, we reserved the right to make our own decisions by our own values. More often than not, we chose something that didn’t work at all. That’s humbling. But it’s also how we’ve gained perspective and grown. I’m still often wrong, but I have developed greater confidence as a leader; I know I can make informed choices and cope with failure when it happens.
  • We built Olark to last. Olark now serves over 11,000 businesses, and we’ve created an organization and a culture that can continue even when both founders are out on parental leave at the same time, while weathering ups and downs as we continue to innovate. That doesn’t happen overnight — it really has taken a decade, and the opportunity to build something that lasts a decade doesn’t come along very often.

So — what if? What if we’d sold Olark, taken the money, and re-invested it in our next big idea? What if we’d risen to leadership positions in a larger corporation with more social influence? Those other possible outcomes would not have been bad, or wrong. I’m not sharing this story to say that you should never sell your company — I’m saying that you should align your decisions with your values first and foremost. If you can do that, even when people question you, you’ll have few regrets.

I’m not sharing this story to say that you should never sell your company — I’m saying that you should align your decisions with your values first and foremost.

Now, I’ll open it up to you. What decisions are you facing in your business? How do you weigh the pros and cons, and how do you gut-check possible directions against your values? Let’s talk about the “what if’s?” and unanswered questions. Uncertainty, after all, is only human.

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