3 Powerful Lessons from Redfin CEO Glenn Kelman

I recently had the privilege of sitting down with Redfin CEO Glenn Kelman to talk about his personal journey. Glenn opened up about his upbringing, his challenges, and the defining moments that shaped the leader he is today.

Here are my top 3 takeaways from that conversation:

1) You Can’t Please Everyone

Even though Glenn grew up in a loving family, he always felt a little different. With a twin brother who constantly competed with him and an older brother who found his way into the news for the wrong reasons, Glenn stood out—and not always in a comfortable way.

At school, he felt like he didn’t quite fit in. And early on, he learned a powerful truth: trying to please everyone is a losing battle. If he had focused on what others thought of him, he says, he wouldn’t have made it. He had to stay true to who he was.

Are you spending too much time trying to fit in?

2) Entitlement Is the Enemy

Glenn attended Interlake High School, where many of his classmates came from wealthy families. He wasn’t one of them. He and his twin brother shared the most beat-up car in the parking lot.

At the time, it was tough—but today, Glenn calls it a gift. That experience sparked a decision that changed everything: he was going to outwork everyone else, no matter what.

No excuses. No shortcuts. Just grit.

Are you letting entitlement or excuses hold you back?

3) Don’t Settle for the Status Quo

As a young adult, Glenn didn’t have everything figured out. He felt the pressure to find his purpose—and fast. If you’re feeling that same pressure today, you’re not alone.

His advice? Experiment. Try different things until something clicks. And when you do find what lights you up, don’t settle. Raise your standards—for your career, your relationships, your goals, and your life.

Why play it safe when you can dream bigger, aim higher, and actually enjoy the process?

Are you pushing yourself to grow, or just staying comfortable?

Glenn’s story is a reminder that success isn’t about fitting in, having it easy, or following a straight path. It’s about staying true to yourself, working harder than expected, and refusing to settle for less than you’re capable of.