If you’d asked Brett Hellman, CEO of Matter, what his weekend plans were years ago, his response would have been this: work, work, and work. Now, you’ll probably find him walking his dog down the streets of San Francisco, digging into Barack Obama’s A Promised Land, and planning a trip with his wife (pre-covid of course). Only after taking what seemed like a risky career move, shedding over 100 pounds, and prevailing detrimental tech norms — he’s forged some of the best work of his life.

This realization of a work-life balance wasn’t something that came easy to Brett. And that’s the case for many tech professionals in the Bay Area. According to Brett, the very idea of admitting burnout was “taboo.” For our Silicon Valley natives, you know what Brett’s talking about. And for those who are new to the scene, the tech industry wasn’t always breezy.

Part of our new series is uncovering the depths of what it means to be a founder, CEO, and trailblazer. While this isn’t Brett’s first rodeo, he has stories, advice, and feedback that’s changed his approach to work-life balance for the best.

“Your facial expressions are making other people feel that you think they're stupid.”​

14-Year-Old On A Mission

Many of us can picture the 14-year-old version of ourselves. Flying through school, entertaining futile drama, and half-assing household chores. But Brett and his friend were busy cold-calling startups from the Yellow Pages at that time. At 14, he got his first job at LA.com and Hawaii.com. High school and college became a blur of various startup experiences until Brett landed his first major gigs at Yahoo and Intuit.

These were monumental moments for Brett’s career. Not only were these his breakthrough jobs into Silicon Valley, but it’s where he received his first piece of constructive feedback that he carries with him to this day.

“I’d casually say [to my boss], ‘Hey, you know, this is a problem, what do you want to do?’ Luckily he responded saying, ‘You know, whenever you present these problems, you should always come with a recommendation and explain why.’”

No one had ever told me that before, but looking back on it now, it's really helpful. [Especially] now that I'm also a people manager. It makes a lot of sense. When you present these problems provide a recommendation along with reasoning to make your boss’ life easier. That’s your job."

Brett 🤝 Feedback

Feedback can be a hard pill to swallow sometimes. To be clear: Feedback is hardly ever personal, but many professionals do take it to heart. That’s only natural. Like any other skill, the more you practice the easier it gets. Brett felt that shift from seeing feedback as an attack on his character to constructive advice to help him grow professionally at Intuit.

“I got the feedback that did kind of knock the wind out of me. I was a product manager running a fully distributed team. I wasn't connecting with people, and I was completely overwhelmed. Luckily my boss said, ‘Hey Brett, your facial expressions are making other people feel that you think they're stupid.’”

“If he had not been so direct, I probably wouldn't have understood how important it was. He unleashed this valid, helpful nugget of feedback. It's still something I think about pretty much every second while I'm on Zoom or even talking to my wife.”

We tend to forget how feedback allows us to contribute our unique, growing talents to a common good. And the source of that feedback usually comes from someone who is personally invested in our professional growth. When Brett realized how feedback from his closest teammates was helping (and not hindering) his growth, receiving feedback became a lot easier. The key is to find people who care about you beyond your job title. And in Brett’s case, your peers that provide radical candor may become some of your closest friends.

No Room For Toxicity

After Brett sold his first startup, Hall, to Atlassian in 2015 it was time for a much-needed break. We say much-needed because Brett found that during his time at Yahoo, Intuit, and Hall, his health was placed on the back-burner.

“There used to be a very toxic culture in Silicon Valley. I think people used to believe that the more you work, the more likely you are to be successful.”

“There were repercussions of working yourself to death in my last company. One, my health has suffered. I put on a ton of weight because you're not eating healthier, sitting all the time. You're not getting exercise. I was working every single weekend. For five years, no vacations, no sick days.”

“For five years, no vacations, no sick days.”​

With low retention rate, high burnout, and employees quitting left and right, it was apparent how unproductive hustle culture had become. With this second venture, Brett’s been able to transform his previous career regrets into core values. At Matter, has brought health to the forefront of the company’s values. Especially amid a pandemic, mental health days are encouraged among his team.

“I learned a lot of hard lessons that way. As the leader of a company, people follow you. If [I’m] working 18 hours a day [and I] don't leave the office, other people aren’t going to leave. I'm practicing what I preach. During the height of the pandemic, we were giving out mental health days when we could tell people needed a break.”

The Takeaways

There is a great deal to learn when it comes to pursuing your career goals. With decades worth of experience, Brett is a treasure trove of advice. If you’re starting in your career or building your own company, here’s what Brett has to offer.

Stop talking and just do it

“At Intuit, I was scared to start a company especially when I had family members that were working at big companies. I knew if I didn't try it, I would regret it.” Brett’s advice is clear: You’ll always be able to land a job at a big company. But you won’t always have the time to pursue your passions. Take risks in your career. If you fail, dust yourself off and try again.

“I used to think coding 24/7 equaled success. I was really keeping myself busy to avoid thinking through the real challenges [that] I needed to solve strategically."​

The presence of greatness

“Surround yourself with people who are smarter than you so you are constantly learning. You should never feel too comfortable in a job. If you do, then you aren't growing and challenging yourself.” It was famously said that we are the average of the five people we spend time with. For Brett, surrounding himself around growth-minded individuals created some of his pivotal career moments. It allowed him to embrace any uneasiness when taking on new challenges. So, why not surround yourself with greatness? It will only make you more ambitious.

Bake in time to think

“I used to think coding 24/7 equaled success. I was really keeping myself busy to avoid thinking through the real challenges [that] I needed to solve strategically. If you just keep building and building, nothing will happen. Dedicate time to think.” In December of 2020, Barack Obama shared his 3-part trick to making tough decisions. Can you guess one of his approaches? Bingo, letting ideas marinate. To make sound decisions, you have to step away. Whether you’re walking your dog, grabbing dinner with family, or strolling around the White House pool — “savor the quiet moments” and let your thoughts run wild.

Get To Know Brett

At the end of every interview series, we ask our guests a series of rapid-fire questions to get to know them better as a leader. Their quirks and habits that have led them to where they are today.

Q: What are you reading at the moment?
A: A Promised Land by Barack Obama.

Q: Who’s a leader you look up to?
A: Stewart Butterfield. His confidence in trusting his instinct is inspiring. To call an enterprise company "Slack" in 2013 — that took hutzpah.

Q: Night owl or morning bird?
A: I used to be a night owl, but I’m a morning person now. I get more done, fewer interruptions, more creative thinking, and I eat healthier.

Q: If you could win an Olympic medal for any sport, real or fake, what would it be
A: Pole vaulting. You work for 10 seconds, and you’re done. And what a view!

Q: If you could instantly become an expert in something, what would it be?
A: Vocab wiz. I would love just to be an expert in the English language.

Q: If you can be anywhere right now, where would it be?
A: Wherever my wife is or Japan.

Conversation Starters

Now’s Your Turn

Like Brett said, stop talking about it and just do it. Ask for that feedback.

​>> Go to Matter​ <<

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Cover Photo: Brett Hellman

Matter: The Future of Feedback

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