We’re looking forward to introducing you to Jake Huddelston. Check out our conversation below.
Good morning Jake, we’re so happy to have you here with us and we’d love to explore your story and how you think about life and legacy and so much more. So let’s start with a question we often ask: What are you most proud of building — that nobody sees?
I’m most proud of building the habit of showing up consistently and trying to spread the word of how business can unlock levels of freedom most only dream about, even though I have no audience yet. I’ve been creating some long form and short form content on YouTube knowing full well that almost no one is watching right now. There’s something humbling and oddly freeing about that. It’s forced me to focus on clarity, honesty, and a craft instead of the validation piece. I’m proud that I’m building that habit before there’s any applause. And knowing that applause is not guaranteed.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m a small business owner based in Texas, building businesses at the intersection of real estate, finance, and technology. I started out working in med device sales and slowly built my way into ownership by focusing on the boring, durable fundamentals like land, cash flow through note payments, and systems that work without constant supervision.
Today, my work spans real estate investing and a software platform called Terra Notes that helps people manage and collect payments on owner-financed loans. What makes it interesting to me is that we are less focused on flashy growth and more focused on building something that lasts and what our customers actually value. Personally I want a businesses that supports real life, not one that consume it. I’m in a season of quietly compounding, refining systems, and sharing what I’m learning along the way.
Outside of work, I’m a husband and a pretty new dad. And with that new lens, it shapes almost every business decision I make.
Great, so let’s dive into your journey a bit more. What’s a moment that really shaped how you see the world?
A defining moment for me was realizing that doing everything “right” didn’t necessarily lead to ownership, autonomy over my time and income, or more freedom. I had a stable high paying job, was checking the boxes, and still felt constrained by time and upside. My time wasn’t my own. My income potential wasn’t my own. Even my territory and customers weren’t really mine, they were the company’s. That realization forced me to rethink how value is created and who ultimately controls it. Since then, I’ve viewed work less as something you do for security and more as something you can design intentionally; around ownership, leverage, and long-term optionality and my favorite word: Freedom.
What did suffering teach you that success never could?
Failing with my first two businesses taught me things success never could because it forced me to confront myself without any protection. I poured everything I had into a company that didn’t work. I ended up about $30,000 in debt and moved back in with my parents at 27. There was no spin, no narrative to justify the failure – just the reality that effort alone isn’t enough, and belief doesn’t replace fundamentals.
That season was humbling in a way success never is. It stripped away ego and exposed how little I understood about business, cash flow, risk, and sustainability. More than that, it forced me to sit with discomfort instead of distracting myself with blind optimism. I had to rebuild my confidence quietly, through the small, unglamorous decisions, rather than big visions.
What that suffering and humility taught me is that responsibility is actually freedom. When there’s no one else to blame and no momentum to hide behind, you either grow up or repeat the same mistakes. That experience reshaped how I operate today. I’m much slower, methodical, more intentional, and always grounded in reality. Trust your gut and look at your bank account daily. Those things don’t lie.
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. What important truth do very few people agree with you on?
Consistency beats intensity every day, and twice on Sundays. Consistency matters far more than intensity, even though intensity gets all the attention. Most people want the massive breakthroughs, rely heavily on motivation, and area alway seeking the shortcuts.
However, in my experience, the people who actually change their lives are the ones who show up when it’s boring, uncomfortable, and quiet. That’s not a popular message, but it’s the only one I’ve seen reliably work.
Everyone wants the profits today, the followers today, the limelight today. But none of that comes without the consistent effort that’s put in every yesterday.
Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. Are you doing what you were born to do—or what you were told to do?
I think most people get stuck asking the wrong question. Instead of asking what they were “born to do,” I think it’s more useful to ask what they can reliably stand to do on the average Tuesday afternoon. I have followed passion and what I felt called and born to do previously, and it left me in a world of hurt. I think following your passion can kill your passion and leads to many failed businesses.
Passion is unpredictable, but assessing what works is honest. My life changed when I stopped chasing what sounded inspiring and started committing to what actually worked. For me that was buying raw land, investing in mortgages, and buying a business. I don’t have a passion for land or owning debt, it’s just what I found works for me and it helps shape the life I want to live outside of work.
My believe is that purpose tends to follow competence, but not the other way around.
Contact Info:
- Website: https://www.terranotes.com
- Instagram: @jakehuddelston
- Linkedin: https://www.linkedin.com/in/jakehuddelston/
- Facebook: https://www.facebook.com/jakehuddelston
- Youtube: https://www.youtube.com/@JakeHuddelston
- Other: https://www.huddelston.com
