Jason Shellen and I overlapped at Google but for some reason, our best conversations always happened outside of the Plex – like on a bus heading to Google’s pre-TED dinner in Monterey, or some random startup event in San Francisco. Jason joined Google when Pyra Labs (the company behind Blogger) was acquired. We’re now both out of Google for enough to time to sit back and reflect on our careers, and the most important question of course, WHO KILLED GOOGLE READER (Jason was its founding PM).

Hunter Walk: So Jason, now that we’re old and can reflect a bit, what have you found – for better or worse – as a common thread in the career decisions you make?

Jason Shellen: I’ve always tried to work on problems I can’t stop talking about. Early in my career, I was compelled by clichéd notions of “changing the world thru technology,” but it was true! My last year of college, I took a class called “Web Publishing”, and I was transfixed. I thought everyone should have the ability to publish to the web. When the opportunity to work on Blogger came along, my values lined up so well that I essentially volunteered for a while because it was so satisfying to see it come to life. Getting to work on a product you love is motivating.

I’m incredibly fortunate to be able to choose what I work on now. Sometimes that means building an exciting idea into a product and sometimes a company. Often, it means selling that product or company to join a larger company. In those cases, I usually ask myself “Am I going to be able to make a positive impact on the company?” and “Can I get into trouble?”. Good trouble: new products, prototyping the future and defining a new way to build products. I like having room to grow and develop in whatever I do.

I’ve had opportunities come up in gaming, banking or the gig economy but when I don’t connect with the core problem, I usually move along even if it’s not in my financial best interest. Recognizing that I have a “Not To Do” list makes it easier to pass those along to friends who are a much better fit.

HW: We were fortunate enough to “grow up” in tech around a bunch of people who are now Bold Face Names – you know, magazine covers, lots of wealth, etc. Is it weird seeing people you know get famous in that way?

JS: I grew up in Silicon Valley and had always found technology fascinating, but I never thought we would be at this point of stardom for founders and tech execs. Now I get to play “Who does Dad know?” at the magazine rack with my kids. A lot of it is refreshing to see since it’s a more inclusive and diverse crowd than just “People that look like Dad.”

The wealth is fascinating because many times the folks who have the most outsized successes are the least likely people to have been doing it for the money. The most impressive of these are the ones who recognize that they should put tech (and their wealth or notoriety) to work for traditionally under-represented voices and lay the groundwork for the next generation of philanthropy.

HW: It’s 11 years since you left Google. Should you just have stayed?

JS: During the harder parts of startup life, I asked myself that question more than a few times. I still have a soft spot in my heart for Google (especially the days of under 1000 employees). It was a launch pad for many pivotal points in my career and an intellectually stimulating place to spend my time.

Before I left, I had a moment of realization that Larry & Sergey had their time in the garage and I wanted the same thing. I wanted to go back to building with a handful of people committed to solving problems in new ways. I have been able to do that a few times over, and it’s rewarding. I wouldn’t swap that for the last eleven years.

When I was forming a new company, I wondered “who do I want to work with?” and a considerable amount of former Google collaborators and colleagues had all moved on to start their own companies. It’s a weird problem to have. It felt like we had all traded to different teams.

HW: You’ve raised VC funding a few times, and I know always had multiple investors interested in backing you. How’d you choose who to work with?

JS: The honest answer is the first time I raised money after I left Google I didn’t know how to choose a VC. I didn’t talk to a lot of the usual suspects because I thought that my ideas were too small or not ambitious enough. I had a lot of inbound interest, and luckily some of those people turned out to be great business partners.

I’ve found that a smart investor is someone you’ll spend a lot of time talking with about your core principles and how you see the world. Your idea may change, the product may change, the company may change so you’ll need to be able to pick up the phone and talk with someone you trust about what comes next. It’s not just about the money. It’s whether they provide sound advice, ask great questions and make helpful connections.

HW: Seriously though, who killed Google Reader?

JS: I wasn’t consulted! I left Google and then five years later they retired it. I heard it might have been a Google Plus executive but he’s not there anymore. From what I understand, by the time Reader was killed, the usage numbers were not on an upward trajectory. Pair that with blogging on the decline in the face of Facebook and Twitter and you have a murky situation. It was also at a time when Google Plus had been given a lot of resources and then hadn’t lived up to internal expectations, so maybe it just drew the shortest straw.

Reader never had an easy time. It was nearly killed before launch in the annual product priorities process. I think it was on a list of “Top 100 projects that should probably not launch” in the summer of 2005. In October 2005, after the beta launch, my manager told me that I should probably disband the team and stop hurting the careers of the engineers involved and find a new project to join. I did not disband the team, and things improved quickly with rapid product iterations (and lots of users).

I’m still proud of the team behind Reader and have fond memories of that time in building a new product at Google. It would be amazing to see what Reader would have become if it made it through the chasm like Google Photos was allowed to do.

Thanks Jason – follow him on the Twitter.