Stride Stories: From a Helping Hand to a New Home

Jeremy is an entrepreneur, real estate agent, and the founder of Squatch Trading

Hi, Jeremy! Can you tell us a bit about your background? What peaked your interest in real estate?


Jeremy: I've been an entrepreneur since 2005 or so, but I did not get into real estate until about a year ago. I got here by way of doing some real estate investing, and I could see the need for getting my real estate license so that I could branch into other types of real estate. It opened up a whole other world of being able to help others. That's my ultimate passion and what my life revolves around. I came from an IT background where I excelled because I love helping others and engaging with technology, so it was a great fit. My doing real estate is just another extension of that, as I get to help others with some pretty large purchases!

You mentioned that you had other business ventures that you had tried before your current career. Would you mind speaking a little more about that?

Jeremy: Absolutely! I ran my own residential PC repair business several years ago, and it was quite successful, but at the time I was starting a young family. I decided that it would be too much for me to take on the demands of a new business while starting a family as well.  

My wife and I started managing a few Airbnbs in early 2018. That's been really fun. It's been awesome doing something together with my wife, whom I love.

Most recently, I just started another company, and this has been a creative idea in the back of my mind for awhile: an outdoor clothing brand. It’s called We use the sasquatch as our mascot of sorts, with the premise being that everybody has a big hairy idea in the back of their mind, and we want to push people towards pursuing those goals and dreams. It’s been fun—a little crazy at times, but definitely not boring, that’s for sure!

Even when operating my own business or in-between ventures, I’ve helped others with their own business ideas. I love seeing people’s ideas come together and be successful.


You clearly have a lot of experience starting businesses. What have you learned about how to best prepare for starting your own business and the pitfalls to avoid?

Jeremy: Each business is its own adventure, right? You’ll always need to do your paperwork and think about LLCs, corporations, taxes, marketing—stuff like that. There are also learning curves with those things, since you have to wear a whole bunch of hats, especially with sole proprietorships or even smaller businesses. You are the marketing team, the finance team, the sales team, and the creative team. That’s the challenge.

There’s another thing that I’ve learned. A friend once showed me the “one page business plan”: a concept that helped me quickly determine if an idea was worth pursuing. With it, I can decide whether to quickly move on to other ideas or even temporarily shelve them. This ability has allowed my brain to push certain ideas to the side and move on to other priorities.

You mentioned that you started one of your businesses, the Airbnb business, with your wife. How has that experience been?

Jeremy: It’s actually gone exceedingly well in my case. She’s my best friend and I love spending time with her. She also balances me perfectly. I’m the kite and she’s the string: neither works without the other! She keeps me grounded, but at the same time, I’m able to show her new business ideas and opportunities. For AirBnB specifically, things have worked out great. I like envisioning the big picture, and she’s a lot more detail-oriented.

What type of skills or personality do you think is best suited for people considering real estate? 

Jeremy: One of the biggest issues—I heard about this before I got started—was the problem of getting “commission breath”. You should be there to help people, and then the money will come. I find this advice to be so true. There are great real estate agents out there, but as the housing market has improved, it’s attracted others who’ve jumped in to get their real estate license. A lot of real estate agents are doing really great and are helping many people, but some agents are in it just for the money, and people can sense that.

As a real estate agent, you’re offering a skill-set during a stressful period in someone’s life—they’re either selling or buying a home. You also take on different roles in the process: you can be a confidant and even a counselor at times. However, it’s worth it once everyone gets to the other side. The main thing is bringing them through this stressful process and minimizing problems the best you can.


How do you prepare for the first few months where business may be slow because you're just getting started? Are there ways to reduce this time?

Jeremy: Absolutely. I have to give kudos to my wife on this one. When we got married, I had some debt from student loans, and she’s a strong proponent of no debt. I quickly realized that no debt was indeed the better way to go! Now we have no debt from student loans or cars or revolving credit cards. We try to maintain as little debt as possible in our lifestyle. That allows us to get really small and tighten up the belt in the case that someone loses a job or is transitioning into a new venture that we really want to pursue.

What's been the most rewarding part of working for yourself?

Jeremy: The biggest reward for me is a recurring theme in all the businesses that I’m in: helping others. With my little IT company, I’d help people who were really aggravated because of the wifi issues at their home. In my real estate work, I’m dealing with people who are worried about this huge purchase or sell that they’ve got going on, and I’m able to step in with a smile and friendly face and help them through that. With my clothing line, I’m helping to push people towards their goals and dreams. With Airbnb, I’m offering a great place to stay and a friendly customer service attitude.

Being helpful really resonates with people—it’s something innate and others feed off of that. People leave extremely appreciative, and because of that, they’re likely to return. And that’s the goal.