Rad Dad Podcast by Kirill Zubovsky

Greg Gottesman

Pioneer Square Labs and the Family Life of a Venture Capitalist

Pioneer Square Labs and the Family Life of a Venture Capitalist
October 16, 2018
Seattle, WA
Subscribe in your favorite podcasting app. It's free.
Smash Notes Top 10 Podcasts of the Week

Episode Summary

Greg is not your average VC. He is smart, hard-working, down to earth, and full of ideas. He has been investing in companies for over 20 years, all while raising three kids. A few years ago he took a leap of faith while founding Rover.com, which sparked an idea for Madrona Labs and now PSL, a startup studio in Seattle. Since the studio was founded, they’ve spun out a number of startups, raised a large venture round, and hired an amazing team of local talent.

On this episode we dive into Greg’s history and talk about why he chose to become a VC, what led to his founding of Rover.com, and why Seattle is a fabulous place for a startup studio.

As someone who holds a joint JD MBA degree from Harvard, with an undergrad from Stanford, and now a part-time professor at The University of Washington, Greg has a lot to say about college and how students (and parents) could think about education given the ever-rising costs of attendance, and often unclear prospects post-graduation.

College is still a great choice, if you can afford it. But, it is important to make a decision as to what you want to study and what future that profession would hold. We need to rethink education, and the kind of financial burden it puts on the society. Don’t go bankrupt, be thoughtful and smart about it.


As far as dad life, Greg was fortunate that his wife chose to leave her work fairly early on and to focus on raising their children. He is the first to admit that she is a better parent, and their family’s success is largely dependent on her. Meanwhile, he supports and encourages her in any way he can, and that keeps their family and marriage on track.

Greg’s got a great philosophy on life, which enables him to work hard and to spend time with kids. That said, he would also tell you that no matter how great of a parent you are, you will make mistakes and you are going to screw up your kid a little bit; that's just part of the process.The goal is to try to do as little damage as you can and be as supportive as you can.

Admit your mistakes, and explain your reasoning to your children. Most importantly, you have to meet them where they are. Your kids are going to be different, so when it comes to spending time with them, focus on what makes them happy. It takes some practice to figure out what works best for each kid.

This logic also applies to studying and eventually jobs. It was a little hard for Greg to admit, he does have a stellar education, after all, but even in choosing your kids’ future it is important to meet them where they are, and to see things from their point of view. Twenty years ago, for example, no one would have thought that `designer` would be a high-paying job, but today, it’s a skill in the highest demand. Who knew?! However, there are many artists, but the ones making top-dollar are the ones who went an extra step and learn cross-platform skills. That’s the key, to encourage your kids to learn more than required.

When asked whether he would recommend becoming a father, Greg gave it a five-star rating. Although challenging in the short run, fatherhood is extremely rewarding, and an experience unlike any other. He recommends thinking of it as a marco event and considering the long-term (positive) impact on your life.

As far as our future is concerned, Greg is bullish. With advancements in Artificial Intelligence and Machine Learning, we will see a huge boost to our lives, a lot of things will become easier. Luckily for us, Seattle is also fortunate to be in the middle of the best talent in these fields.

p.s. During our interview, Greg talked a lot about the awesome early Rover.com employees, as well as his friends at PSL. He is not the one to take credit, but I had to cut it to basics. You know who you are. Keep on doing what you're doing!

Episode Notes

Links from this episodes

About Rad Dad

Rad Dad is a podcast about the lives, decisions and view of successful, intelligent, and peculiar parents. Fun stories, insights, and of course, occasional parenting advice.

How to listen
Subscribe in your favorite podcasting app. It's free.
You May Also Like
Rad Dad Podcast is created and hosted by Kirill Zubovsky