House Notes: Starting Over

For the past few weeks, I’ve been sharing coffee-focused newsletters because, well, the Guesthouse is a coffee company.  So I figured I should be talking about coffee. But truthfully, I don’t enjoy writing about coffee nearly as much as I enjoy drinking it. What I do enjoy is writing about my journey.

So while the Guesthouse is still very much a coffee company, I hope these personal reflections help shed light on why it means more to me than just the products we sell.

Onwards. 

Starting over is hard. I’ve done it more times in the past two years than I have in my entire life. After working in pharmaceutical research for over eight years, I was laid off. That moment changed the course of my life when I took the leap into something completely different by starting The Guesthouse.

There’s an excitement that comes with being a beginner. Every bit of effort feels like progress, every attempt feels like learning. People cheer you on when you’re starting something new because in the beginning, there’s no pressure to be perfect. But being a student forever isn’t enough to grow a business.  At some point, you have to become the operator. You put in more effort, but the rewards seem to keep getting farther away. Selling your first bag of coffee to a friend? That’s a rush. “I DID IT! MY COMPANY IS REAL! I MADE $5!” But selling to that same customer month after month, in a market full of other options? That’s where loyalty becomes actually becomes the commodity and a new type of hard takes over. That initial excitement is only a temporary fuel.  At a certain point, the learning curve flattens. What was once fun and novel becomes routine. And now, to actually grow, you have to execute at a high level - again and again.

Last month, The Guesthouse turned one. One whole year.  At the beginning, I approached the business with as wide of a lens as possible.  What began as a coffee-cocktail concept eventually become a mobile event bar and wholesale company focused on trying to take a mindful approach to coffee.  That shift happened slowly, making small changes along the way based on new things I’d try, as well as changing in tandem with my personal life.  The Guesthouse gave me an opportunity to reconnect with Lizzie by using my mobile coffee bar as a unique way to welcome visitors to her open houses.  That small idea sparked our SAME SAME BUT DIFFERENT collaboration when we ran 17 coffee and real estate events all over Denver together and collected over 500 winter coats for our community.  That partnership ultimately created the foundation of our relationship now and my ability to call her the love of my life.  We now co-own the Guesthouse together.  

If I hadn’t started over with the intention of being open to new things with this business, I’m not sure that our relationship would be what it is today. And I couldn’t be more thankful for what it has become.  Here’s us. 

Now, I’m starting over again as a licensed real estate broker in Colorado so that Lizzie and I can continue building something meaningful.  We’ll co-run both the Guesthouse and our real estate businesses, working side by side to build our life together on our own terms.  While Lizzie is several years into her real estate journey, I’m back in beginner mode again: visiting every open house I can, letting my creativity run wild, asking a million questions. But I’ve learned how to start over now, which I do think is a skill.  I’ve done it enough to know that while being the new kid on the block and dreaming big can be fun, that can also distract me from the real objective: build the core business.  

I’m not taking the same “let’s try everything and see what sticks” approach that I took with the Guesthouse. This time around, our model is very simple: deliver as much data-backed value as possible and give our clients the absolute best experience we can.

We already have an incredible knowledge base from our training at the Armbrust Real Estate Institute, and we’re pairing our hospitality values that we take from the Guesthouse with the passion and heart we’ve always had.  I’m still giving myself a chance to enjoy the beginning phase, but I’m more focused this time around on closing the gap to excellence as quickly as possible. 

I think back on the different chapters of my life and I’m pretty amazed how each time I’ve started over has led me to something amazing.  I lived in Mexico playing professional soccer, I surfed every day in San Diego in my 20s, I worked remotely and woke up in a new city every week just a few years ago, and now own two businesses and am planning a life together with the woman I love.  Each chapter entirely different than the other; each incredibly impactful on who I am today.  

For those of you who have had the courage to start over, I salute you.

And for those thinking about it, consider this: you’ll never know how a change will turn out. That’s life.  

But you’ll never forget what it felt like to bet on yourself. 

Starting over isn’t about losing what came before; it’s about building on it with new eyes, new courage, and a deeper sense of who you are. 

If you feel the pull toward something different, don’t ignore it. 

It could be the beginning of the most meaningful chapter of your life.

Stay curious,Ian

P.S. If you know someone who could benefit from a real estate team that truly cares—we’d love to connect with them here.

P.P.S. Feels right for a Monday.