5 things you learn raising a puppy that will help you succeed in a startup

Catherine Guarnieri
Upside Team Blog
Published in
7 min readJun 6, 2019
Belly rubs are good for puppies, not so much for coworkers.

From in-office snacks and cold brew on tap to unlimited PTO and flexible working hours — startups are constantly raising the bar when it comes to new work perks. When my own company, Upside Business Travel, announced a new “Pawrental Leave” program (one full week of paid time off when you bring a new pet into your life) I knew it was the perfect opportunity to fulfill my lifelong dream of owning a dog. Throughout my twenties I had built enough savings (and responsibility) to feel confident enough to raise my very own pup.

I’ll spare you the saga of how we (my boyfriend and I) came to own Mosey but suffice to say in early 2019, we had a 10-week-old puppy on our hands.

(Day 2 of Mosey)

In the last six months, I’ve learned so much about patience and selflessness. I’ve also learned that a lot of the lessons Mosey taught me were strangely applicable to my professional life at Upside.

Here are the top five things I learned while raising a puppy that can help you succeed in a startup:

  1. Respect is earned

There is a lot of information out there about ‘pack mentality’ in dogs. I won’t pretend to be an expert in the science. What I do know is that Mosey and I had a bit of a power struggle once she made it into adolescence. She certainly didn’t care where I went to college, what my advanced degree was in or who my last employer was. None of these things mattered to her — and they won’t to your colleagues in a startup either.

Most startups are chaotic — more work than working hours, more challenges than solutions. Your goal is to achieve what you can, to the best of your ability, with the resources you have. Relying on your background to earn favor won’t get you very far. Even if it does initially, it likely won’t last long. To truly earn respect, show up, work hard, and celebrate others’ achievements as much as your own.

zero respect

2. Positivity always triumphs

Most dog trainers will tell you that positive reinforcement training is an absolute must to raise a healthy and well-adjusted dog. The American Kennel Club promotes positivity training “because it is more rewarding and fun.” That’s in reference to the dog, but from my perspective it’s far more fun and rewarding for the human too. Many dog trainers agree that training dogs to behave out of fear isn’t in their best interest (or their owners’). There is nothing that upsets me more than seeing Mosey’s tail between her legs. Why? Because I know she hasn’t learned anything, she’s just scared.

Failure is a natural part of being in a startup but it can be easy to fall into a culture of CYA (cover your a$$). At Upside, we embrace failure for what it is — an opportunity to learn. We make a sincere effort to focus on the positives over the negatives. We never assign blame (though most everyone is quick to own it) or chastise. Why? Because a culture of fear breeds long term negative impacts for a corporation.

(Mosey loves Upside’s pup-friendly office space — and her rawhide bone!)

While having a company culture that is encourages positivity is helpful. I have also found that applying positive reinforcement training to my own habits is an excellent way to stay motivated in a startup environment. As a Type A personality, experiencing failure or even just days without a ‘win’ is taxing on my psyche. A 2018 Stanford study showed that having a positive attitude actually correlates with achievement and performance. So when I find myself in a failure-driven funk, I take on a task that will help alleviate that stress. Some simple but effective ways to feel accomplished? Write a weekly recap of your teams’ action items, or even finalize an expense report that’s gone undone for too long. If you’re like me, you’ll feel an immediate positivity-boost.

3. Be willing to ask for help

Three months into having Mosey, my boyfriend took her out for a jog. Twenty minutes later, Mosey was spent and stubbornly refusing to budge about a mile from our apartment. So he picked her up (all 35lbs of her) and turned back, only to discover he’d lost his keys somewhere along the way. Knowing he couldn’t carry her while backtracking their run, he did the next best thing he could think of. He found a kind woman enjoying a day in the park with her own dog and asked if she would watch Mo while he retraced his steps.

Joe & Mo ( in her lighter months)

There have been a number of times we’ve had to ask for help with Mosey. We have asked friends to watch her for a weekend. We’ve asked fellow dog walkers to borrow poop bags. Most commonly we’ve sought advice from family, friends and colleagues. The fact of the matter is we would have gone crazy (and broke) raising Mosey without our network to call on.

Asking for help seems so simple and yet so often in a startup it can be the hardest part of your day. Whether it’s because you don’t want to admit defeat or you don’t want to burden coworkers with additional work — asking for help is difficult. I’ve had to quiet my ego and ask for help plenty of times at Upside. My requests have ranged from the simple (“Please help! I cannot get this SQL query to return anything”) to the more complex (“I feel very overwhelmed right now”).

Every time that I’ve raised my hand and sought the help I need, I’ve received it. Your colleagues (more often than not) will say yes, but you need to ask the question first.

4. Embrace the chaos

Your dog isn’t going to be the #goodestboy after one puppy training session. It is unrealistic to think you’ll have a well trained dog even after your pup ‘graduates’. It takes time and commitment to get your pup in top form. So along the way I learned to embrace the chaos that came with puppy ownership. My new rug? Slightly less ‘new’ looking now. My leopard-print shoes? A few bite marks too many to wear now.

I once locked myself out of my apartment while walking Mosey on a lunch break. Instead of falling into a state of panic, I took that as a sign to spend a few extra minutes with my new pup. Work would still be there when I returned.

When I first started at Upside I found the chaos startling. I had begun my career in a very structured marketing agency and the (breakneck) speed at Upside was a lot to get used to. Over time I learned to embrace it — and having Mosey only accelerated the learning curve. I could control a lot but not everything. I had to make decisions with imperfect information. I had to be willing to fail (see #2). I’m now far better at maintaining my cool when it feels like fires are popping up everywhere at work.

5. The shine will wear off but the hard work is worth it

Puppies are cute — case in point:

swoon — she’s totally worth the work

But when the initial endorphin boost of having this adorable ball of fur wears off — you’ll learn very quickly how much work is really involved.

The same is true of joining your first startup. With all the perks of being part of something new, startup life is a good life — but it is not without its challenges. Sometimes it’s long working hours. Sometimes it’s playing five different roles at once. Sometimes it’s being faced with a problem that has an overwhelming number of webs to untangle. Whatever the case may be, there will come a time in your first startup where the newness wears off and the realities hit hard.

But it’s worth it.

Startups give you the chance to build something from nothing. At Upside, I see my work come to life in days and then get to watch it have an immediate impact. I get to talk with customers about how we’ve made a difference in their lives. I get to work alongside some of the smartest people I’ve ever met. I get to grow in my strengths and my weaknesses. I get to help solve big problems. That’s powerful stuff.

So embrace the challenges as they come. Recognize that while the ping pong table is cool, the real perk of working in a startup (to paraphrase President Theodore Roosevelt) is getting to work hard at work worth doing.

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We were named one of Rover’s Best Dog-Friendly Companies, 2019! Do you and your pup want to join our team at Upside? Check out our career page for current postings.

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