Don’t Delay the Tough Decisions

What is the biggest failure you've had in your life either professionally or personally?

You know at TaskRabbit, I feel like there were definitely some decisions that I would make differently if I could go back.

Such as?

One of those decisions was you know, we solved it later on by completely overhauling the entire site in 2014, but the problem was we didn't get to our mobile platform fast enough. And in 2008, we created a web experience that was this auction-bidding based model. It was high friction. And at the time it worked. It was very close to the eBay model, but over the course of the next you know, 5, 6, 7 years it wasn't scaling. It wasn't scaling with the customer base, particularly the new consumer that was used to the instant you know, Lyft, Uber, Instagram, Twitter. And we took way too long, I think, too kind of morph the experience into something that was more on demand.

And that was really hard for us. I mean it included me having to cut 30% of the team, and go through a whole round of layoffs. We had to completely reorganize and restructure the organization. We had a lot of money in the bank, so it wasn't really monetary related, but it was more like, this isn't working and this isn't sustainable. And so those were really, really tough decisions. And as I look back, do I see ways we could have avoided that? Yes, I do.

What could you have done? How would you deal with adversity now? What did you learn from that?

I think what I learned was at that point, we had scaled the team faster than where the business was. And so we had hired too fast, and the business hadn't really caught up with where our hiring was. And then the people that were there, that we had hired were still working on what I would call the old platform now, which was you know, more web-based, more auction and bidding. And I think realizing that, that platform wasn't going to be the platform that took us to scale faster would have been key, because we wouldn't have overhired. We would have been able to restructure things in a more graceful way, but I think we let it, I let it run too long, the course that it did. And so then it was about turning, not just a ship, and not just tacking a sailboat, it was like turning this massive tanker into a new direction. And that was really, really painful for everyone involved.