Managing anxiety with Hipmunk's Co-Founder

Rho Team
March 5, 2020
read time
1 minute
Reviewed by
February 9, 2024

Six years into running Hipmunk, the travel booking startup Adam Goldstein co-founded with Steve Huffman in 2010, Goldstein made an observation: He was anxious. Really anxious.

By all metrics, things were going well. Hipmunk had raised a series of capital rounds totaling $55 million, it had dozens of employees, a drove of loyal users, and was on its way to being acquired by SAP Concur in 2016. But as Hipmunk’s revenue grew, so did Goldstein’s anxiety. Success didn’t bring contentment, it brought heightened emotions, irrational fears, skipped meals, and self doubt.

“Even though you’re happy with the traction, you’re feeling less happy as a person,” Goldstein tells Ali at Rho. “That is a profound, repeated pattern that does not easily lend itself to explanation.”

Today, as a visiting partner for Y Combinator and mentor to other founders, Goldstein is spending time reflecting on the role of anxiety, and using his personal experience to help others mitigate its negative effects.

“There were moments that felt like it couldn’t get any more stressful,” he says of his eight year tenure at Hipmunk.

Some of the moments you might expect — fundraising frustrations or close calls with running out of money — but even everyday occurrences at the company had the power to raise his blood pressure.

For example, when Hipmunk’s first employee quit, Goldstein says his initial reaction far outpaced the amount of worry actually needed.

“I was devastated by it,” he says. “I wondered if there was something fundamentally wrong with our company, or our culture, or if we were doomed, or if it was going to precipitate a bunch of employees quitting. All of those things went through my head. We didn’t have any employees quit for the first two years. It was a long time. I certainly had in my mind, ‘Hey, maybe we’ve built such a great company that no one will ever quit!’”

The anxiety had an impact on his ability to manage effectively: “I was less open to new ideas in the company,” he says. “I was more set in my mindset of what we needed to do. I was acting like a CEO of a company that was in deep trouble, as opposed to one that has just experienced what every company goes through.”

Goldstein is now coaching founders and managers to be more selective about the anxieties they indulge. In an essay called “The Anxiety Algorithm,” Goldstein shares a framework to manage stress more intentionally, and reduce the counterproductive, pervasive worries keeping you awake at night.

Here are five strategies Goldstein shared with Rho to manage anxiety more effectively.


“A lot of anxiety comes from people having expectations that are out of line with reality,” Goldstein says. “Expecting that no one would ever quit was completely unrealistic. If I told myself, ‘Come on. Every company, even the greatest companies in the world, have had employees quit,’ that would have helped to put things in perspective.”

Making an effort to gain perspective — by reframing your thinking or having conversations with other seasoned experts — helps prevent the ‘sky is falling’ narrative. Understanding the inherent relationship between increased traction and increased stress can also be helpful.

When Goldstein first teamed up with Steve Huffman, a co-founder of Reddit and Reddit’s current CEO, it felt creative, interesting, and low stakes.

“I was super excited to convince this well known guy to start a company with me,” Goldstein says. “We had an agreement that he would work on my idea for the duration of Y Combinator’s batch in the summer of 2010, basically three months. If at the end of three months it wasn’t working, then he would get to pick the next idea.”

“Everything had to come together quickly and that was energizing and cool, but it also wasn’t that anxiety producing,” Goldstein remembers. “It was like, ‘Hey if it didn’t work, we had a Plan B.’ It was just the two of us, and we knew that we could build other stuff if we needed to. It felt low stakes.”

Compare that to a few years later: “After we raised our Series A round and we burned through a few million dollars and were looking to raise our Series B round, then the stakes felt enormous,” Goldstein says. “We had a team of more than a dozen people at that point. When the fundraising got tough, we wondered if we would be able to raise money at all. We started to worry, ‘Are we going to have to lay people off? Are we going to have to do some really bad stuff to our product, and pepper it with advertisements just to break even?’”

At the beginning, the number of ways to fail is small. You can imagine all of the potential outcomes. As a company, project, or team scales, the potential ways to fail become increasingly exponential.

That’s why perspective is important. Just because you can imagine potential failure points doesn’t mean they’re destined to come true. “The things that we think are not necessarily reality,” Goldstein says.


“I see a lot of founders lock up under uncertainty and stress, and that’s the worst thing to do,” he says.

Let’s say a situation like this occurs: At a company with three customers, if one customer cancels a contract, executives may jump to emergency action to keep the other two customers happy. The sales team may suggest giving the two customers a big discount, or making a trip to take them out to dinner.

“That’s a reasonable thing to think about,” Goldstein says. “But a lot of the time, when a customer cancels a contract or when a deal falls through, it’s actually a signal that what the company was offering was not what the market wanted. And that’s really important to know and react to. Holding on too tightly to an idea that isn’t yet proven is really dangerous.”

In those situations, the right approach is to say, “Hey, we just got a signal from the market. Nothing in life is certain. It sounds like the thing that we thought was the best is not the best. So either we’ve got to make it the best, or we’ve got to do something different,” he explains.

Taking action will also reduce undue anxiety.

“There’s no worse feeling than being stressed out and helpless,” he says. “Making that decisive choice not only increases the likelihood of the startup succeeding, but also just feels better.”


Setting consistent habits and building some structure into your day is a simple way to reduce stress.

“Founders who get into a routine of talking to customers or talking to employees tend to have more resilience in the face of change or surprises than founders who each day are going through a wildly different pattern,” he says. “They feel like there’s no structure to their life and no structure to their company and everything is being done by the seat of their pants.”


An honest evaluation of your relationships might be more revealing than you think.

“One of the patterns I’ve noticed within startups is that when things are just good, people don’t make a change. When things are awful people make a change, because it’s so obvious that it’s bad. But when things are just kind of bad, people don’t make changes,” Goldstein says. “It takes a tremendous amount of bravery as a CEO or as a manager to say, ‘This is going okay, but it could be better. I’m deciding to make a change.”

He sees this often with early stage employees. Founders might say, “There was this person on the team and they were a great person, but what they had was just not what we needed at that moment in time in the company’s life. I wish that I’d realized that sooner.”

“I think most of the time that founder did realize it sooner, but they didn’t want to listen to themselves,” Goldstein continues. “They convinced themselves that it was going to be okay, until it just slowly ground down on themselves and their coworkers.”

It can happen in all kinds of relationships.

“I see this a lot with founders who are dating someone they’re not really in love with, but the idea of being single terrifies them,” he says. “Or they’ve got like an advisor to the company who’s well known and they’re not getting great advice from that person, but they’re just afraid to stop working with them.”

“It is super under appreciated how easy it is to fall into the trap of settling for something that’s not that good,” he adds.

You’re not alone

Lastly, it’s important to remember the feelings you’re experiencing are not unique to you.

“It’s really hard for founders to appreciate the fact that everyone else is stressed out and anxious,” Goldstein says. “Founders are just consistently seeing stories in Tech Crunch and in The New York Times and Wall Street Journal about how everyone else is doing great. And even when those companies aren’t doing great, they’re still bigger than them.”

“Even when you hear about unicorns laying people off or having a down round, it’s still a multi-billion dollar company,” he continues with a laugh. “A lot of founders think, ‘I would kill to be in that person’s situation. They must be so happy to have this big company.’ But really, probably not. Probably they’re just as stressed as you, if not more.”

The solution? Being open and honest about your experience.

“The sooner people can realize [everyone else feels the same way], the less it is going to feel like a unique failure as a manager,” Goldstein says. “Founders have to experience that first hand, talking vulnerably with other founders about what it’s really like.”

Related Posts

Join thousands of top business leaders today.

No personal guarantee or personal credit check required.
Rho is a fintech company, not a bank. Checking and card services provided by Webster Bank, N.A., member FDIC; savings account services provided by American Deposit Management, LLC and its partner banks. Conditions apply.