What does it take to go from a curious nine-year-old tinkering with computers to leading product strategy at some of the world’s most powerful tech companies?

In this episode, Gabe Monroy reflects on his path through the tech world. Raised by a single mom who ran her own bookkeeping business, Gabe got his start helping set up computers for her clients. That hands-on experience sparked a lifelong passion for technology.

Over the years, Gabe would go on to sell two startups (including one to Microsoft), serve as a leader in cloud innovation, and hold the role of Chief Product Officer at DigitalOcean, where he helped shape tools built specifically for the world's small businesses. His experience at the company offered a powerful look at how product strategy and purpose can align.

The episode explores what made DigitalOcean different, including its commitment to small businesses underserved by larger cloud providers, and its remote-first team spanning nearly 1,000 employees across 185 countries.

One of the most compelling parts of the conversation is Gabe’s approach to creativity and focus. Living on a farm with goats and chickens, he shares how unplugging from technology helps him find clarity—and even his best ideas. His take on “flow state” and the Japanese concept of Ikigai offers a fresh way to think about success, especially in an industry where learning never stops.

Whether you're just getting started or rethinking your path, Gabe's story is full of insight and serves as a reminder that innovation can come from the most unexpected places.

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