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October 06, 2025 By Jessica Peguero

Working with Your Partner: 7 Lessons from the Field

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Twelve years of marriage isn’t a lifetime, but it’s something I’m proud of. Yesterday, my husband and business partner, David Moore, and I celebrated that milestone. We also happen to be co-owners of OnPar Automation, our newest adventure.

If you’re building something with your spouse, partner, friend, or family member, I hope this resonates. This isn’t expert advice, just reflections from someone living the messy, meaningful blend of entrepreneurship, family, and partnership.

A Little Getaway and a Big Reflection

We escaped to the mountains for a short anniversary trip. No kids, no meetings, no Slack pings. In that space, away from our routines (and the small humans who occupy 80% of my brain), I found some clarity.

Despite the chaos of running a business, parenting, and trying to be a decent human, I realized something simple: we’re happy. Not perfect, just genuinely happy.

That’s when I started reflecting on why we work well together, and where that foundation came from.


Our Puerto Rico Chapter: The Storm Before the Calm

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Before OnPar Automation, before robotic ball pickers and business meetings, there was a wild, beautiful, and humbling chapter that taught us almost everything we know about resilience and teamwork.

In 2015, we quit our jobs, packed up our lives, and moved to Culebra, a small island off Puerto Rico, to take over and expand a vacation and dock rental business.

It was equal parts thrilling and terrifying. At this point, our hotel management experience consisted of booking and sleeping in hotels, but mostly AirBnB's. Our Denver friends thought we’d lost it. David, ever the visionary was confident we could make it work. I was excited but cautious, leaving behind a job I truly loved at TEGNA Media, where I’d been thriving in the urgency and community connection of the news world.

But my empath-self was exhausted by the constant pulse of information, and the promise of slower island living was tempting. So I agreed to sink or swim with David.


Sink, Swim, and Everything in Between

We worked hard. Really hard.

Within months, the property went from #8 to #1 on TripAdvisor. We built systems, improved operations, connected with guests and locals, and started to feel at home.

Then life threw us a surprise: one month after arriving, I found out I was pregnant.
Zika was in the headlines. There were no hospitals on the island, and travel to the mainland wasn’t easy. It wasn’t in the plan, but then again, nothing about our life was following a script.

As the months went on, David carried more of the load. He learned some Spanish, managed guest relations, maintained the docks, and built relationships with locals. He’ll tell you those were the best years of his life. For me, it was transformative but also isolating. We were experiencing the same adventure, but from two different vantage points.

Then came the hurricanes.


When Everything Changed

In September 2017, Hurricane Irma hit Puerto Rico, followed two weeks later by Hurricane Maria, one of the most powerful Atlantic hurricanes on record.

Blog - Working with Your Partner Hurricane Maria NOAA

Shown above is an image of Hurricane Maria as it passed over the island. Puerto Rico is not visible under the storm.

Our daughter was 10 months old. She learned to walk in those two weeks between storms.

We hunkered down in one of our one-bedroom villas, no power, no running water, eaten alive by mosquitoes, sweating through every layer. We were lucky compared to many, but those days left an imprint.

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After the storms, no guests were allowed back on the island. Tourism stopped completely. For a while, we had only small windows of light and power each day, thanks to the island’s generator. Income was almost nonexistent.

That’s when we learned something humbling: no matter how independent or strong we think we are, we still need people.

Puerto Rico stole our hearts forever—not just for its beauty, but for its people. Even when everyone around us was facing their own challenges, they found ways to help. We were embraced with kindness and community at a time when everyone had reason to pull inward.

That same year, I found out I was pregnant again.

It became clear we couldn’t stay. We returned to the mainland with no jobs, no home, and two babies to care for. We bounced between friends and family for a while before finding our footing back in Colorado.

David rejoined Range Servant America, and we were deeply grateful. It gave us time to rebuild. But his entrepreneurial spirit never quieted for long—and eventually, it was time to take another leap.

Cue OnPar Automation.


What We Learned (and Keep Learning)

Out of all those storms, literal and metaphorical, came lessons that continue to shape how we work and live together.

I’m not a psychologist or business coach. I’m just someone who’s learned a lot about partnership under pressure. Here’s what’s helped us stay married and build something meaningful together:


1. Earn Trust

David had a plan and it worked. Watching him handle language barriers, business curveballs, and natural disasters turned my quiet skepticism into genuine faith.

Shared core values make trust easier. When your deal-breakers align, the rest feels lighter.


2. Share the Load

We divided work by strength, not preference. I thought I’d be front-of-house, but newborn life shifted me to systems and customer communication. David wanted to catch every “first” but did what the business needed.

Partnership means taking turns carrying the heavier load without keeping score.


3. Protect Respect

Stress shows up in tones and side-eyes. You can disagree, debate, or even get loud, but don’t cross the lines you can’t uncross.

Mutual respect has to stay intact, especially when the pressure’s on.


4. Set Boundaries

Our business is like a third child. It demands constant attention. But even third children need bedtime.

My dad told me early on, “Don’t take your business into the bedroom.”
He was right.

Have fun together. Talk about something other than the business. Remember the you that existed before the partnership.


5. Keep It Positive

Celebrate small wins. Catch each other doing something right.

I can be a “waiting for the other shoe to drop” person, with a side of hope, but I’ve learned that staying optimistic (and mindful of my words) creates a healthier space for both of us.


6. Talk About Money (Calmly)

Money is one of the most common stress points for couples and it doesn’t get easier when you’re in business together.

We agreed early to keep our business finances separate from personal ones and to avoid borrowing from friends or family. It wasn’t always easy, but it helped us sleep at night.

Check in weekly. Don’t let silence grow around financial stress.


7. Practice Gratitude Daily

This one’s everything.

Gratitude resets perspective. Whether it’s a record sales week or a slow month, saying thank you—out loud, daily, keeps the focus on what’s working instead of what’s missing.

Appreciating what your partner carries (even if it’s different from what you carry) creates momentum that criticism never will.

We also try to stay grateful for every customer interaction, every handshake, every small LinkedIn “like.” The tiny things add up.


Still Learning, Always Grateful

I don’t pretend to have it figured out. This is the most learning I’ve done in my entire adult life.

My background in communications and marketing helps; I’ve just had to add business management, accounting, and robotics to the mix.

David brings decades in the golf industry and the kind of entrepreneurial drive that keeps us moving forward. We’re also lucky to work with an incredible team. Jon, our regional sales manager on the East Siiiiide, and Tyler, our installation and support lead, who bring both experience and humor to every day.

Our meetings? Never boring.


The Big Picture

Running a business with your partner is one of the greatest growth opportunities there is. It’s also one of the hardest.

Start with a solid foundation. Keep checking in. Remember your “why.”

The hurricanes still come, sometimes literal, sometimes emotional, but if you hold onto trust, boundaries, and gratitude, you can weather anything together.


If you’re building a business (or a life) with your partner, I’d love to know:
What helps you stay grounded at work and at home?

About Author

Jessica Peguero

I’m a designer, marketer, and business owner who thrives on innovation, storytelling, and coffee. As co-founder of OnPar Automation, I’m passionate about creating solutions that help businesses grow. Inspired by purposeful ideas, people doing good, and the beauty of nature, I channel these influences into both my work and life—where my two little girls constantly remind me of what truly matters.

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