When losing your biggest love inspires entrepreneurship 🐾

“It was truly important for us to do this. It wasn’t like, ‘Oh, this is a great idea to make money.’ This is something we’re really passionate about because we care. We care about animal welfare, and we care about people being able to have pets in their lives. There are so many studies showing just how beneficial having a pet can be for people.” — Garrett

For many founders, the big “ah-ha” moment doesn’t come from a trending idea or a late-night conversation… It comes from personal hardship and a desire to address the problem.

Brad and Garrett Bewkes–co-founders of PetHSA–have always adored the pets in their life. But until their dog Mia, they had never experienced just how quickly unexpected costs can stack up.

While Mia was a happy pup, she was also very sick. And until her last days, Brad and Garrett did everything they could for her to be as healthy and comfortable as possible.

Many families who are faced with the same difficult decisions often can’t choose their pet over financial obligations…

And Brad and Garrett wanted to make sure no one would ever have to pick one over the other.

Everything aligned to a new direction

“While we were both pursuing our MBAs, we realized there were bigger and better things in the world we could be doing. I was excited about so much of what I was learning and thought, ‘I could really do something I’m passionate about and have a greater impact on the world.’” — Garrett

When Brad and Garrett decided to go back to school for their MBAs, they weren’t actually new to the business world.

Brad had already explored entrepreneurship through various avenues over the years, growing a small fashion company, owning a real estate business, and working with various startups. He had also started writing a forthcoming memoir, documenting their experience with Mia.

While Garrett had never started a business of his own, his role as a Media Executive at a major political publication meant he was ultimately running the business operations for the company. This allowed him to gain arguably more experience than a grad school program could even offer.

He initially loved his work, but as the political climate was shifting and becoming more toxic, he decided it felt best to step away and move on.

It was the perfect moment to invite something new and exciting into their lives. Together, they decided an MBA could provide them both with some fresh perspectives and insights around current trends and best practices in business.

What they didn’t realize is this experience would be a major catalyst for change.

Along with the changes happening at Garrett’s company, he was also dealing with some hardships in his personal life.

And when they sat and thought about everything that was going on, both amongst themselves and through conversations with their MBA cohort, something kept coming up: Their passion for pets.

It was time to follow a new dream.

A pivot in the name of pets

“I realized I had started making a lot of my decisions around Mia so I could be with her when she needed me. It was the first time I really felt like my pet came first. Then, after business school, Garrett pivoted out of his work and I reduced some of the volunteer activities I was involved with. It just made sense to bring my experience together with Garrett’s and start PetHSA.” — Brad

With Garrett’s executive-level experience (plus, a family history in finances) and Brad’s long-established entrepreneurial spirit–paired with this new sense of excitement from their MBA–they knew they had a strong foundation to start with.

Even with a solid idea and a loose plan in place, a lot of those first moments still felt like they were jumping in with both feet, open to where the experience would take them.

That’s because they already knew that without data, they wouldn’t have a clear direction. And to get data, you have to go all in.

“As much as you make the plan and do all the work, you really have to test it out in the market. Then, if you feel like there’s something there and you’ve built enough of a business case—whether the goal is to attract investment, eventually sell, or something else—you can start to attract the broader business community.” — Brad

Instead of getting too caught up in planning and waiting until things were “perfect,” they went for it.

And when the fears and challenges started to come up, they knew they just had to push through.

Working through the less-than-ideal moments

“I had concerns about getting in too deep with self-funding and then not being able to get out if it didn’t work. You can always eventually shut something down, but that can cost you tens or even hundreds of thousands of dollars. But for us, we could never just shut things down overnight. We can’t simply detach our users from their records. It’s really important to us that we do things the right way. Because at the end of the day, this isn’t just an idea to make money—it’s something we’re genuinely passionate about. We care.” — Garrett

Whether you’re self-funding or seeking investors, finances never seem to come easy. For many founders, it’s one of the biggest concerns or stressors.

But as they got the ball rolling, some more personal challenges started to surface.

For one, Garrett was used to working around people and managing a team. Now, he’s working (mostly) solo.

“I've always loved spending time with my teams and feeling like I’m part of something bigger—a group of people working hard together toward something.” — Garrett

Thankfully, between Brad and their support network, no one is ever truly alone.

And it’s that support that really helped them feel more confident as they began developing their product too.

“It was a little nerve-wracking going into our very first conference with an idea that was still being built and wasn’t live yet. There really wasn’t much to show people. But we got some amazing validation from the industry, and now we have some really important people telling us, ‘We can’t wait for you guys to launch.’” — Brad

With a solid support system and validation, it would seem like everything would be a breeze from there on out.

But because of what they’re building, they faced a tricky chicken and egg situation.

Without a high volume of existing transactions, potential partners weren’t interested in committing.

And without financial partners, they couldn’t run a platform that helped people with… HSA finances.

That alone could be a big enough hurdle to cause people to throw in the towel. But with persistence, they’re currently working through that obstacle.

It’s easy to keep going when pets are involved

“I was a panelist at a youth conference, and as I was getting to know the other panelists before we went on stage, we all connected over our dogs. Pets are just such a natural way for people to connect. Every time we talk to someone who’s as passionate about their pets as we are, it really validates why we want to keep doing this.”— Brad

Besides being able to bring their dog to work (who doesn’t love that!), their desire to make sure every pet parent can experience a long life with their pet, regardless of what comes up, will always keep them going.

And because this deep love for pets is what drives their work, even the draining moments don’t seem so bad.

For Garrett, the endless process of working through user acceptance testing, product reviews, and quality assurance can easily make him feel burnt out.

But then, he starts to see progress and how what they’re building will actually help people and their pets.

“It feels like almost every week, I’m getting rejuvenated and excited all over again.” — Garrett

And because the pet industry is booming, and filled with tons of like-minded pet-loving humans, the constant communication with others in the industry feels reassuring too.

The random check ins or words of support can serve as a nice little reminder that together, they’re building something great.

The perks behind building with your partner

“Because we’re doing this as a team, we bring two different skill sets and mindsets to the table. Sometimes that creates conflict, but I think that’s actually good for the business. At the end of the day, having different opinions is healthy. If you only have one perspective, you’re not necessarily looking at other ways to approach a problem or do things differently.” — Brad

For Brad, there’s always been a desire to build something with the person he’s married to.

Besides the logistical, business side of it, it’s a way to build a stronger connection with the most important person in his life. And of course, it’s to benefit the pets they love so much.

When it came time to start PetHSA, the partnership just made sense to Garrett too.

Brad was already joining him on business trips and was a natural networker.

“We’ve always done things together, and we’ve always been a good team. So I think there was a natural point where I didn’t even really think about it that much. It’s really important to have the right person to co-found with. For me, there was definitely a trust factor in knowing that if I brought Brad in—even if he didn’t stick around for the entirety of it—I could trust him to protect the data, protect the information, and protect the mission.” — Garrett

Key takeaways from building together

Though they’re still early in their founding journey together, Brad and Garrett have already realized some pretty important factors that make the experience more successful and enjoyable.

🌱 Don’t burn old bridges

“I had a lot of cheerleading on the sidelines, whether that was from my husband, my family, or my sisters. I also had a ton of business colleagues and contacts from my last job who were really cheering me on—and some of them even helped me get things rolling.” — Garrett

🌱 Allow yourself to make mistakes, and pivot

“I love that we ran into a major challenge, found our pivot, and went for it. But in that pivot, I allowed myself to repeat some mistakes from the past. I let myself get distracted by this shiny object over here or that shiny object over there. It’s good to remember that when you find your pivot, don’t treat it as a necessary evil. It’s your next product. It’s the thing you’re most excited about. So how do you really hone in on that and make sure the product stands on its own and provides real value?” — Garrett

🌱 Be open to continuous learning

“I think a lot of it is continuing to ask questions, ask people for favors, and try everything. When you’re a startup, you don’t know what’s going to stick, so you really do have to put yourself out there and see where it takes you. You have to manage your expectations, but still be excited about the future.” — Brad

When’s the last time you audited your own wellness?

You get plenty of advice. What you rarely get is a pause. Each month, we’ll share a simple prompt to help you step out of execution mode and consider what “founding well” looks like in your world right now.

Many founders are skilled at pushing through. So skilled, in fact, that they often don't notice how depleted they've become until they're running on fumes. This isn't a test or a diagnosis, it's simply a chance to check in with yourself honestly. No judgment. No action plan. Just a moment to notice where you are today.

The burnout spectrum

Where do you find yourself today?

Rested → Feeling replenished, present, and capable.

Functioning → Managing responsibilities, but operating mostly on momentum.

Foggy → Struggling to focus, prioritize, or access clarity.

Wired → Productive on the surface, but fueled by stress, urgency, or adrenaline.

Brittle → Feeling stretched thin, reactive, or close to your limit.

Numb → Disconnected from motivation, joy, or even your own needs.

Feel free to pull out old fashioned pen and paper, or create a new doc just for journaling, and spend a few focused moments thinking about the following:

• What clues helped me choose this spot on the spectrum?
• What have I been normalizing that might actually be a sign I need support?
• If someone I cared about felt exactly as I do right now, what would I want for them?
• What am I carrying today that doesn't actually belong to me?
• When was the last time I felt genuinely rested?

There’s no right or wrong answer. If nothing comes up, that’s okay too! Use this as space to notice what is real for you today. A few messy lines are enough.

If you're comfortable sharing your insights with us, let us know at foundingwell@vallelegal.com.