Sentry CEO Milin Desai On What Leaders Can Learn From Marvel’s Ant-Man

Welcome to CEO Rapidfire, fast-paced questions with today’s most successful founders and CEOs. Be sure to look for these special Q&A editions of my newsletter, where I’ll share insights from the amazing leaders in my network.

My latest guest is Milin Desai, whose favorite life hack is best served hot. (For more, keep reading!)

Milin is CEO of Sentry , an observability platform that helps software developers quickly identify and fix code issues — by telling them exactly what the problem is and what’s affected. Used by 4 million developers and 100,000 organizations in 146 countries, Sentry processes 790 billion events each month. The company, whose customers include Disney and Microsoft, has raised more than $200 million in funding.

Milin joined Sentry in 2020 from VMware , where he was GM, cloud services. He earned a master’s in computer science from the University of Southern California, before starting his career at what is now Veritas Technologies and rising to senior engineer. He also served as product manager at Riverbed Technology .

Monitoring code will become critical to observability in the AI era, Milin argues . “Everything around us is becoming software,” he says. “Software is changing faster than anything else. What we are starting to see is this need to help developers who write the software understand how it’s doing in production from a user standpoint.”

Sentry, which has passed $100 million in annual recurring revenue, reflects that shift, Milin says: “We are starting to see the momentum of monitoring your code.”

Here’s what Milin shared in our CEO Rapidfire interview:

The one secret to succeeding as a leader, in 5 words or less: Be curious.??

What was the most exciting “minute” of your leadership journey? It was midway through my career at VMware, when folks I looked up to for advice started coming around to “pick my brain.” I vividly remember the first time this happened.??

One truth you wish you knew about leadership before starting? Take your time to hire the right person. It requires a lot of patience, but if you build the best team, you can overcome any obstacle.?

If you had to do battle with a giant, what weapon would you use? There is merit in David vs. Goliath or the fact that Ant-Man is an Avenger. One’s size is only a limitation when one makes it a limitation. I wake up every morning trying to unseat giants. My best weapon is grit — no one will outwork me. I will learn what I need to, surround myself with people who are smarter than me and grind harder than anyone else could.

Your worst mistake as a leader (and what you learned from it): Communicate what is important not once, but over and over. Do not assume everyone is listening the first time or is getting all the context.?

Top 3 websites, blogs or podcasts you can’t imagine your day without: Basketball channels on social media, Hacker News and Syntax.fm .

What popular leadership advice do you disagree with? “Fake it till you make it” can be a great aphorism early in your career as you are learning, growing and fighting self-doubts. But too often, people take this advice literally. There’s a lot of pressure on leaders to always have the right answers, to portray an infallible persona. Instead, be humble. This allows you to be in learning mode all the time. Be honest and authentic about what you do and don’t know. People will help you, and you’ll build trust along the way.??

One life hack you can’t live without: My wife’s cup of chai in the morning or after a long day. It’s magic.

One soft skill that you’ve realized is supremely important: The best ability is adaptability. If you want to work in tech, particularly at a startup, you better learn to be flexible in all aspects.??

The one thing that makes a good leader great is: When people know you believe in them. I know it sounds cheesy, but I have a small team, and when they know I have their back, we make good things happen. So a good leader, IMO, is someone that can work for their team and not the other way around. And it’s really tough to do that. I’m lurking in several Slack channels, DM-ing everyone, and sometimes people freak out that the CEO is messaging them. But in reality, I’m trying to cover their blind spots, share missing context and connect the dots. And that’s the one thing everyone cannot do. I can bridge the company together. So while it may be hard to break the CEO stigma, a good leader connects the company. I’m a very expensive router, and that’s what I try to be great at.

Your secret to building a great team is: Look for humility (with just enough of the right kind of arrogance), and folks unafraid to make timely decisions.???

The key to navigating hypergrowth is: I will always come back to adaptability. Product-market fit is fleeting. Your product changes, the market changes. Company processes that worked with a team of 100 will not work when you hit 200. You can never get complacent — lean on first principles and ask yourself, “Why are we doing it this way?” a few dozen times a day. Also, don’t forget to enjoy yourself. Hypergrowth is fun!?

Look for humility (with just enough of the right kind of arrogance), and folks unafraid to make timely decisions.???

Every leader must read… Amp It Up: Leading for Hypergrowth by Raising Expectations, Increasing Urgency, and Elevating Intensity by Frank Slootman, a fantastic distillation of leadership principles along with practical advice.?

What are you most excited about at work right now? It’s incredibly exciting when your company enables millions of developers to ship quality software, at a time when a) more code than ever before is being shipped and b) software — and software quality — has never been so important to the global economy. Being on the frontlines of this ever-shifting landscape is thrilling, and to have a part in shaping the future of how software is made is the honor of a lifetime.

Your one “non-negotiable” in business (or life) is… Pessimism. If you can’t see the potential of a world that’s better tomorrow than it is today, then what’s the point of anything we do? We are motivated by the positive changes we wish to see. If we fail, we are optimistic that we’ll learn and get better the next time we try, and there always is a next time.?

Thank you, Milin, for sharing your leadership thoughts this week. To learn more, follow Milin on LinkedIn .

Thank you for reading! I'm interested in hearing your thoughts in the comments below. For more insights from my experience as a serial entrepreneur and how we can harness the power of software to change the world, be sure to subscribe to Entrepreneurship and Leadership.