Stayhound and Portland pet sitters, sitting in a tree…

I’ll be honest – reactions to Stayhound have been mixed when I talk to Portland pet sitters. While many are excited about having a new way to find and retain clients, some are skeptical or even downright hostile. Usually, the objection is that they don’t want to be lumped in with amateurs – regular schlubs who have no liability insurance or professional standing.

They’re right. And I totally get that.

Stayhound isn’t looking to supplant Portland pet sitters – or pet sitters anywhere – who are professionals with existing client bases. We couldn’t if we tried.

Talking to enthusiastic and engaged pet parents here in Portland, I was struck with the dedication many of them have to their dog walkers, pet sitters, and kennels. But the problem that kept being mentioned was the need for a “backup” – someone you could call if you have a last-minute trip, or your regular pet sitter is booked, or you just plain forgot to get a pet sitter. That’s the problem – well, one of the problems – we’re trying to solve.

That said, I’ve also had great conversations with Portland pet sitters, dog walkers, and other pet professionals who see how Stayhound can help them grow their business and delight their existing clients. Every week, I talk with professional pet sitters here in Portland as well as other cities who are thrilled to tell me what features we can develop to help them not only promote their businesses through social accountability and discovery, but also to differentiate themselves.

I’m always excited to talk to Portland pet sitters about your business, so please feel free to email me at – whether you love Stayhound or hate it. At the very least, I’ll buy you a coffee and we can swap stories about crazy dogs.


The day I became everyone’s pet sitter

Back in June, I started talking to people about an idea I had for a site where pet owners could connect online and trade pet sitting. Some people thought I was crazy. Others thought it was a great idea. As of this weekend, both have asked me to pet sit.

A lot has happened between then and now. We got into a tech incubator for one. Some really cool people at Wieden + Kennedy let me interview them about how they care for their pets when they travel. And I’ve been asked to pet sit. A lot.

Both the skeptic and the enthusiast had known me for several months before my announcement that I was going full time with Stayhound. Neither had ever asked me to pet sit before.

Then, on Thursday night, I got a panicked text message from a buddy:


He’d been working late hours the past week on a business presenation he was going to give out of town on Friday. Between the work distraction and the fact that it was a short trip (he left Friday morning and returned Saturday night), calling his usual pet sitter had totally slipped his mind.

Fortunately for him, he lives less than half a mile from me, and on my regular morning running route. I picked up Augie on my way back from my run with Jake, and I had a fun day and a half being a two-dog household.


What did this experience tell me? That all our furry friends need a backup plan. And that the best people to provide that backup are probably people you already know… you just didn’t know that they loved taking care of pets until they start a company about it.

Side note: the buddy with the pet sitting emergency above? Was one of the ones who told me Stayhound wouldn’t work. When he offered to buy me a bottle of scotch in repayment for taking care of Augie, I told him he should just use Stayhound.