From 0 to 10: Making the “right” decisions

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.

I walked back to our office in the dark, feeling vaguely sick to my stomach. I fielded questions and listened to my team’s frustrated objections, and ultimately sent a conciliatory email that left the door open, ever so slightly, for further discussion. I knew I’d made my decision, though. Olark wouldn’t pursue acquisition in 2013 (or since, for that matter).

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.

Because Olark remained independent, we’ve been able to evolve in the ways that matter most to our team. Some of these have been things we expected and planned for, and some have happened organically. In particular:

• 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 developed talent internally. The decision to build a unique and independent company was also a decision to build a leadership team that understood our product, culture, and vision. Prioritizing Olark-specific knowledge and alignment has meant that the people who fit our leadership profile may not have decades of corporate experience or degrees from top universities — what they often do have is a history of creating impact at Olark, often starting as individual contributors and developing skills in multiple areas until they’re ready to head up a team or take ownership of a product area. This focus on internal growth has helped us hire and retain talented people who would likely have hit a ceiling at many bigger companies.
• 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.

I’ll never know where we’d be today if we’d been acquired. But I know Olark is a company I’m excited to lead for another decade or two — and also that it’s a company that Olarkers are excited to work for. I have a balanced life, great customers, and a happy team, and I think that means that even if there was no one “right thing to do”, I at least did do right by my teammates, customers, and our shared values.

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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