One Day, You Too Can Work from the Dog Park

Dogster founder Ted Rheingold waxes nostalgic about the site's early days.


Scotia Bank / Dogster “Rich Moments” from SAY: Content on Vimeo.

Starting Dogster was the dream of my life. I always wanted to work on something I was passionate about; something that brought joy to people’s lives and allowed me the flexibility to feel like I was living my life as opposed to having my life live me.

What’s amazing is I never expected that Dogster could do that for me. It started as a hobby project, something I thought people might like. I never dreamed it would become bigger than that. When it did take off, I suddenly got to play an avuncular role to hundreds of thousands of dogs, as I wasn’t able to have a dog where I lived at the time. I hardly knew all the dog breeds out there and barely understood just how many dog issues existed. All I knew was that people have profound connections to dogs, as I did with mine growing up, and that joy hadn’t been brought to the Web yet.

And then a funny thing happened. I started leaving my home office mid-afternoon to clear my head, and I would go to nearby dog parks. I realized for the first time that small dogs were pretty great. That senior dogs were pretty great. That lazy dogs, slobbery dogs, hyper dogs, agile dogs, and handicapped dogs were all not just pretty great — they were absolutely great. They were also charming, smiling, and loving creatures, and I loved them all right back.

As Dogster started to become a real business, the joy I received from being able to bring joy to our readers grew. It also meant we could have our own offices where we could bring our dogs. Once my wife and I married, we found our own dog, Moxie, at the SF SPCA. We made sure we went to the park. The humans would play soccer and our dogs ran with us. Having been locked in cubeland jobs earlier in my life, I’d pinch myself thinking something so fun was actually a significant professional advancement.

Yet, I have to say that running a 20-person company was more stressful and challenging than I ever imagined. Weeks would go by where I felt I barely left my desk. I became completely at the mercy of my life in complete contradiction to my original goals, and it put great strains on my health, my marriage, and my dog’s walk schedule.

I tried pushing through even harder, thinking that success in business meant such a level of sacrifice. But what I finally learned was that life is simply too short. I down-ratcheted my expectations and pressures I had put on myself, stopped taking everything so seriously (the business was about sharing passions for dogs on the Internet after all!), and made it a priority to get back in control of my life. We found a new partner who relished doing much of the boring work of sales, legal, and HR, and who wanted us to simply focus on making the best, most enjoyable experience we could for our audience.

Now we get to work from the park again, so to speak, and the team was able to resume the pleasure one gets from working their dream jobs instead of having to doubt their own passions. It took a lot of work to cross that chasm, but I’m so glad we’ve put everything back in perspective. The best part is that the product we make, the experience our customers have, the satisfaction we take from doing our jobs have all improved since those early days.

So, anyway, who wants to meet up at the park? I’ve got a frisbee and a tennis ball and some treats.

About the Author: Ted Rheingold is the founder of He is currently VP of Social at Dogster’s parent company, SAY Media.

Sponsored by Scotia Bank. Richness is everywhere.

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