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Navigating Product Careers & Angel Investing with Mike Oliinyk (ex-Uber, Wise, Wolt)
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Navigating Product Careers & Angel Investing with Mike Oliinyk (ex-Uber, Wise, Wolt)

How to Pick Your Next Product Gig Without Leaving Money on the Table.

I met Mike in 2023 while visiting Tallinn, Estonia, for work. A friend organizing a product conference messaged me, mentioning that Mike had been invited to speak. Since he was in Tallinn and I had some free time, I invited him for coffee. We've stayed in touch ever since!

Mike has built an incredible product career. He led product teams at Wise and Wolt (acquired by DoorDash) and was an early employee at Uber. It seems like he has a knack for spotting great companies before they become obvious.

What did I learn from Mike?

"Your manager is the most important person in your early career—the difference between a good and bad manager can define you for years."

  • Mike strategically moved from larger, more stable companies to smaller, riskier startups to take on bigger roles.

  • He recommends prioritizing learning opportunities over company prestige when picking a first PM role.

  • A good manager in the early career stages can have a 10x impact on career growth.

"If you realize early that a company isn't the right fit, it's better to leave quickly than to waste a year trying to make it work."

  • Leaving a company too soon, too often can hurt your CV.

  • However, staying too long in a bad fit can stall growth—it's okay to move on if the environment isn’t right.

  • Hiring managers may overlook one or two short tenures, but multiple short stints raise red flags.

"When I joined Wise, I wasn’t thinking about exits or equity—I was sold on the culture and the ability to grow fast."

  • Mike didn't expect Wolt and Wise to grow as much as they did but recognized strong founders, culture, and market potential early on.

  • Wise had global ambitions from day one, while Wolt started in the Baltics but scaled rapidly by focusing on operational excellence.

"One day you feel rich, the next you realize you’re spending 80% of your time in meetings that don’t improve the product."

  • Wolt’s acquisition by DoorDash was one of the biggest VC-backed exits in Europe.

  • Initially, there was euphoria, but later, corporate bureaucracy slowed down decision-making.

  • Large acquisitions often mean process-heavy environments that slow down high-performance teams.

"If you believe in the company, negotiating more equity can be life-changing. It’s a bet, but one worth taking."

  • Equity is often easier to negotiate than salary, as companies see it as a long-term incentive.

  • Mike prioritized equity over cash when joining Wolt, which paid off significantly.

  • Understanding vesting schedules, dilution, and company growth potential is critical when evaluating stock options.

"Most job applications look the same. If you don’t put effort into standing out, you’re already behind."

  • The job market for PMs has slowed down, and companies have introduced longer career paths with extra IC levels.

  • Networking is key—attending in-person events and building relationships gives a competitive edge.

  • Standing out in job applications is crucial—most candidates fail to write strong cover letters or tailor applications properly.

"Most angels aren’t making crazy returns. They invest because they want to be part of something bigger."

  • Successful exits (like Wise and Wolt) created a new wave of angel investors in Europe.

  • Many operators see investing as a way to stay connected to startups and give back to the ecosystem.

  • Investing is not a reliable way to get rich—most angels lose money compared to traditional investments.

"I fell for the hype. The tech was cool, but the problem didn’t really exist."

  • He once invested in a hyped mixed reality startup without fully validating the real-world problem they were solving.

  • Another bad investment came from ignoring red flags in the founder's knowledge and approach.

  • Following trends blindly in investing often leads to failure—understanding the problem deeply is key.

"I invest in founders who deeply understand their problem—not just those with a cool idea."

  • Founders who lack a deep understanding of their industry or fundraising process are major red flags.

“The best way to future-proof your career? Keep learning and build relationships that matter."

  • PM roles are evolving—fewer managerial positions and more senior IC roles are emerging.

  • Angel investing is growing in Europe, but it’s still high-risk, low-liquidity.

  • The best way to grow in both product careers and investing is to build strong relationships and focus on long-term learning.

Tune in!

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