Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Jack Delehey, Founder of Delehey College Consulting, LLC, located in Denver, CO, USA.

What's your business, and who are your customers?

I help high school students (and their parents) navigate the college search & application process in a holistic, start-to-finish manner. I work with families over multiple years to ensure their path after high school is right for them!

Tell us about yourself

My story dates back to 2010, when I was a high school senior myself. As the oldest child in my family, I didn’t have any older siblings to ask about the college planning process. And it seemed a LOT had changed since my parents went through it. It was sink-or-swim for me… and I struggled with college planning a lot.

Once I finally got to college (and felt very lucky to end up where I did), my goal was simple: to create a company that gave students all they needed to know about college planning… in one single, streamlined location. Thus, Delehey College Consulting was born.

Motivation is easy–when I see the smiling faces of my students and their parents, not just when they are accepted to the colleges of their dreams, but even as they accomplish small goals along the way, I feel a tremendous sense of pride.

What's your biggest accomplishment as a business owner?

In 2020, I had a problem: not enough hours in the day! I started to reject families who wanted to join my program. Then I had an idea: could I somehow streamline my teachings or restructure my coaching so I could take on more families?

From 2020 to 2022, I restructured my coaching program in a hybrid model. I still offer the exact same one-on-one personalized coaching to each of my families… but now there is a component they can go through on their own time (via course form) that simultaneously keeps them on track. This transition wasn’t easy but has been tremendously effective. My students have experienced a more streamlined planning process, and I’ve been able to take on more families.

What's one of the hardest things that come with being a business owner?

The hardest part is also the most fun, in a way: it’s the realization that this is all on me. There’s no boss to go to if I need help. I’ve got to figure out creative solutions to problems daily. And to me, that’s hard… but it’s also fun & rewarding.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Understand that “business” is just solving a problem for someone…that’s truly it! When you think of business this way, it becomes much less daunting. In my case, the problem I am solving is many high schoolers feel lost when it comes to college planning. I give them a plan! That solves their problem.
  2. If you can, “scratch your own itch.” This comes from Tim Ferriss, but I think it’s really powerful. The reason I have become good at what I do is because it wasn’t that long ago I could have really, really used a college planning coach! When you “scratch your own itch,” it becomes a lot easier to take the next steps because you have empathy for your eventual customer.
  3. At the start, say “yes” to everything. When you’re just getting going, I think it’s vital to realize you never know when/where you’ll catch your break. Say yes to that random coffee date. Say yes to going to that networking event. Sure, later down the road, you’ll hit a point where you absolutely should start saying “no” to more and more opportunities as you hone your craft. But at the start, just say “yes”!

Is there anything else you'd like to share?

I really couldn’t do this without my incredible students. You can check out many of them here (

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.