Christopher Jackson shared their story and experiences with us recently and you can find our conversation below.
Christopher, we’re thrilled to have you with us today. Before we jump into your intro and the heart of the interview, let’s start with a bit of an ice breaker: Have you ever been glad you didn’t act fast?
Being humbled by the plethora of mechanical, electromechanical, software, and other technological challenges that I at times have to “sit in the same room” as the problem to truly understand, yes! I am glad that I did not immediately react to address certain scenarios with speed. In the fields I often have to deal with, this would be observed as “intermittent problems”, or problems that are not consistent enough to make immediate judgement calls based upon the available data in that moment.
Even in business, I am glad that I am deciphering when it is best to make swift decisions vs. when it is not. That has come over the years with experience, but in hindsight, has saved me from rushing into domino effect problems or certain situations that would have manifested into “bait-and-switch” type motions.
Can you briefly introduce yourself and share what makes you or your brand unique?
Sure, and thanks for having me back on the platform for a second time! It’s great to catch up on what’s been happening with me and the businesses since I was first welcomed to the CanvasRebel platform to tell my entrepreneurial story back in 2024. When we last connected, I was navigating the commercial real-estate realm, figuring things out one property at a time since owning Ready Lock Go Self Storage, Flying Frog Car Wash, and a single-family home investment property in Katy, Tx. Since then, things have grown in a pretty big way! The company is now on its third commercial property, Flying Bubbles Car Wash-Kuykendahl, that sits in Spring, Texas off of 17307 Kuykendahl Road, where re-vitalization and market stabilization efforts have taken place since August 2025.
Thinking back over the years, what started with leveraging the equity in my first home by 2022 to start what has now evolved into Dwellinghouse Investments LLC and its commercial subsidiaries, I have now seen my brand truly establishing itself in ways where commercial and SBA lenders are acknowledging and forming trust in our strategic direction through building solidified relationships and experiences together. Furthermore, the continuous motion of building trust based on integrity, and not lip-service, has served me well within our local customer bases across the entire Houston community. I once started Dwellinghouse Investments as a small, individually-ran company focused on taking overlooked, underperforming, distressed properties and transforming them into their real potential as consistent, long-term, cash‑flowing assets. The vision has only grown bigger! Thankfully, my companies are progressing in execution and outcome alike to a point where I am able to professionally advise others who are breaking into the space, scaling their emerging businesses, or looking to pivot strategic directions based upon my experience and how I have grown in the various industries as an owner-operator. My staff and team are now to a total headcount of 3 employees at Flying Frog Car Wash, 2 attendants at Flying Bubbles Car Wash-Kuykendahl, and last, two helping hands at Ready Lock Go Self-Storage for maintenance needs.
I’ve expanded thus far in the commercial real estate realm through the self‑storage industry via Ready Lock Go Self Storage in 2023 and diversified into the commercial car‑wash sector via 8 bay self-serve facility, Flying Frog Car Wash in 2024, and 6 bay self-serve and one bay – in bay automatic (IBAS), flex-serve, Flying Bubbles Car Wash- Kuykendahl in August of 2025. Along the way, I’ve balanced a full‑time tech career since 2019 at Rockwell Automation and currently, Microsoft since 2022, while also handling sporadic life curveballs as I remained laser-focused on a portfolio that now sits north of $2 million in commercial assets. Within my future endeavors, I’m targeting improvements on operations for long term sustainability, tightening up system efficiencies, looking to convert data into outcomes from my background as an engineer, and purposefully accelerating growth in ways that I feel are intentional and sustainable for both my facilities and teams. If there’s one theme to my journey since we last talked, it remains to be this: I stopped waiting for the “right time” and started building the opportunities I wanted to see.
Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. What breaks the bonds between people—and what restores them?
What a great question. In my view, bonds start to break when we drift away from the values that make us human and allow us to live well alongside one another. When trust is breached, when integrity slips, when security, honor, or hope are compromised, the foundation that relationships rest on begins to crack. Those aren’t small things — they’re the very pillars that hold human-connection together!
The restorative way to repair those bonds are through intentionally doing the opposite of whatever damaged them to begin. It’s through consistent, steady work of rebuilding trust, showing integrity, creating safety, and choosing actions that realign with the values that were lost that allow relationships to find their way back.
What did suffering teach you that success never could?
Suffering reminds you of the integrity of your values that success never could, as there is no greater filter. In suffering, we tend to question ourselves, others, our purpose, and the extent to which we operate. We get frustrated with the lack of success so much that we begin to look for alternative solutions, side-routes, succumb to false realities, not live in our truths, and other factors because of the outright pain that it welcomes.
However, I would encourage all to see suffering instead as your stomping grounds. It welcomes clarity, teaches clairvoyance, and builds wisdom that would be otherwise overlooked if success came first. While success is always the desired outcome, suffering teaches us how to sustain success over the long term. Conclusively, suffering grounds us within where we currently are before success accelerates us to where we desire to be.
So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. Is the public version of you the real you?
Without a doubt! I am not one to bite my tongue on transparency of hardships, tough trials, tribulations, or uphill battles to get to where I would like to be. I do not have it all together and am humble enough to admit that. I believe that this openness of showing that I am just as human as the next person, make common mistakes and have, at-times, negative tendencies, hold onto fears just as anyone else, and so much more is what draws me closer to people, as opposed to operating as a robot. It takes a lot to remain both positive and postured at times since having the public eye and perception on me often. However, I am learning in the process how to still remain myself regardless of what direction the public eye would like to steer me and have no regrets about that.
Okay, so before we go, let’s tackle one more area. Could you give everything your best, even if no one ever praised you for it?
Yes, as my willpower was never dependent upon others’ approval ratings to begin. To have the vision, drive, tenacity, and motor to get things done when everyone else strives to disprove, denounce, degrade, and turn down your dreams and ambitions due to their own circumstances, must come solely from within. I learned very early on along my business journey, especially as a small business, that you have to have tough skin and be willing to go against the grain to get to where you are looking to go. The same individuals today who discredit your work are the same individuals tomorrow who often praise your credibility once you have reached certain levels of success they once doubted you on,
Contact Info:
- Website: https://dwellinghouseinvestments.com
- Instagram: https://www.instagram.com/_onlythat1/
- Linkedin: https://www.linkedin.com/in/christopher-jackson-36085076/
- Facebook: https://www.facebook.com/ChrisxMichaelJackson/
