How to Move On When Your Business Fails, with Roee Adler

Today, we’re focusing on the things that don’t work or haven’t gone our way. Failure is an inevitable part of every founder’s journey — scary as it may be. But as this episode teaches, how we move through those failures can inspire our next success.

This week, we sit down with Roee Adler — former Chief Product Officer of WeWork and Soluto, who was part of 4 successful startup exits — but also 3 startup failures. His experiences run the gamut, making his story a masterclass in resilience, leadership, and the realities of pivoting when things don’t go according to plan.

Welcome to Unfinished Business, the podcast where we dig into the whys, hows, and WTFs of building and thriving in business — hosted by longtime founder friends Alex Schinasi and Lee Rotenberg. Read on to learn how to spot, handle, and bounce back from potential failures. You’ll be stronger for it.

Alex: There’s obviously a lot that has gone well for all of us, but our listeners are really interested in what happens when it doesn’t. To go back to your journey, is there a specific company you want to talk about?

Roee: I've failed so much it's difficult to choose. Maybe I'll start by quoting a friend. She said, “If you don’t know how to lose, you don’t know how to win.” It’s such a powerful statement because the best way to never fail is to never try. Some people want a job to make a salary and do other stuff, which is amazing. But some people are entrepreneurs. They wake up in the morning and want to drive change.

If you don’t take risks, the change you make is small. If you want to make a big change, you need to take a big risk, and big risks mean there’s a likelihood of failure. I’ve tried many things, some small, some big, some succeeded, some failed. I always try to take failures with a smile, wonder what I could have done better, and let it shape my journey.

Lee: I was thinking about your previous startup, Santa. It was a rocket ship in terms of PR blitz. But when it came time to pivot, how did you manage that failure with your team?

Roee: Santa was a difficult episode. We had a big idea in late 2020 when money flowed like water from VCs. We launched within 10 months of raising money, reached $1 million in annualized revenue within 6 months of launching, and had a large group of happy customers.

But the unit economics were horrible. As we analyzed it, there were factors we didn’t consider. The company was burning a lot of money because it was a logistics-heavy business. We tried to pivot, but when it became clear to me that it was never going to make money, I felt the weight of responsibility to our investors.

From that moment, I knew any day we kept operating was burning good money that could go to a company with a chance to succeed. So I used that spiritual energy to shut it down quickly and return the money to our investors. Most of the money we raised was still in the bank account. Shutting down a company of that size and parting with so many amazing people was heartbreaking, but it was the right thing to do.

Alex: How did you turn that ‘failure’ into a positive experience for your entire team?

Roee: I didn’t, and I also don't think it was my place to. There's a non-reciprocal relationship between a founder/CEO and team members. When one side fires the other, it's extremely important to respect the tragedy of the situation.

The last thing I wanted to do was make excuses or explain why it's “actually good for them.” What we wanted to do was tell our truth, explain the rationale from a business perspective. And it may sound weird, but to leave room for grief. There is a sort of grief in being let go from a company. And there’s a different kind of grief when something that you worked on, that you loved, is just gone.

Alex: What tips can you share on bouncing back? Any steps that worked for you?”

Roee: Tactically speaking, it's important to acknowledge that failure takes time to bounce off of. I remember sitting with one of our lead investors and a good friend for many years, Michael Eisenberg. He said, ‘I'm with you, Roee, but you have to take at least two weeks and do nothing—just spend time with family and friends.’

Reflecting on what went wrong is also very healing. You ask, ‘What could I have done differently so that I would have not reached that point?’ Sometimes the answer is, ‘I should have never started this.’ Sometimes it’s about specific decisions.

Lee: How do you not drink the Kool-Aid for too long? How do you realize when to stop selling the dream to yourself and be realistic?

Roee: If you’re about to run out of money and you don’t have strong enough signals to convince investors to put in more, then there's a high likelihood that your idea doesn’t have justification to exist.

But sometimes, like in Santa, this is not the case. On the top-line, you should have goals and metrics that represent success. If you're not getting even close, that’s one big signal internally. The second is if you’re burning a lot of money. If so, you should have a much lower threshold for answering the hard questions quickly because, for the most part, it’s not your money.

Lee: What are the red flags when you see a company that’s not going to happen? And what signals tell you a company will succeed?

Roee: There’s a truism in the startup industry: Ideas are meaningless, execution is everything. It’s easier to spot red flags than know if something will succeed.

Number one is the lack of founder-market fit. I’ve heard so many entrepreneurs have ideas in healthcare but don’t understand how the world works.

Number two is not thinking about the complexities of go-to-market. My partner and I got excited about the world of physical experiences like amusement parks, but we couldn’t figure out the go-to-market strategy. That killed the idea.

The last red flag is thinking too small. I always ask, ‘If you reach all your goals tomorrow, what’s next? How can this be a first step toward something bigger?’

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