What Does Seattle Have to Do With a Chicago Startup?

James Y Kim
ILLUMINATION’S MIRROR
4 min readSep 2, 2023
Photo captured by the article’s author

I was in Seattle this past weekend visiting friends. It was my first time in the Pacific Northwest and the scenery that I’ve heard so much about certainly met my expectations. I don’t consider myself an outdoorsy person but I definitely appreciated the endless evergreen tree and mountain landscape. As a Midwestern, I often long for a change in scenery. I need that time away from Chicago to recharge my energy and experience a different perspective and culture.

During my time in Seattle I’ve spent a lot of time thinking about this next phase of my startup. We recently received an invitation to join a Chicago based startup accelerator program that will help us prepare to pitch in front of investors for our next round of funding. In a number of ways, this invitation has become a catalyst to progress forward for us. It’s gotten the ball rolling for us to convert the startup to a Delaware C-corp and all that goes into becoming a more structured company. From setting up a board to setting aside an employee option pool, things are starting to feel much more real now.

Photo captured by the article’s author

As a first-time startup founder, every experience is new and uncharted territory. Over time, I’ve realized that the ideation and product development stages have come more natural to me. Since launching our beta student loan management platform several months ago, I’ve shifted much more of my attention and energy from product development to finding ways to attract new customers. However, this marketing component has been more challenging to figure out.

Initial validation and product market fit have always been a part of the process in our journey. However, after our beta launch, the realization has set in that both targeted reach in building brand awareness and succinct messaging need to be tightened up. This is the most important piece of the puzzle right now to gain traction.

Photo captured by the article’s author

The conversations with my Seattle friends have helped me realign the spotlight on this component of the business. As I write this article, I’ve concurrently reached out to the alumni relations for the community college I’ve taken my initial business courses before attending Booth for business school. We need to go where the potential customers are but with a targeted approach. I know we can’t go too broad. Otherwise, the net we cast is not going to reach the right audience.

So, what does Seattle have to do with our Chicago based startup? Spending the past 3 and a half days there have exposed me to a different city vibe. The architecture is totally different, where the newer and more modern buildings have taken over older Seattle. In some ways, these new buildings give the impression of the new Seattle as being a bit sterile. However, this contrasts the young and hip vibe the people give off. I sense there’s a lot of unique stories and life experiences within Seattle’s inhabitants.

Photo captured by the article’s author

This juxtaposition also tells me that I don’t know how these two contrasting elements relate to each other, being in the same city. It also tells me that if I were to have conversations with the people, I’ll begin to understand these contrasts.

Ultimately, it’s a reminder of knowing who your customer is. What are their stories? What are their motivations? What are their dreams? Once we understand these foundational elements, we’ll begin to see a clearer picture on what their behaviors are. These behaviors will then allow us to see patterns. As we see the patterns, we’ll be able to get to know who they are and how to talk to them more effectively.

Thank you Seattle. Now, time to get back to work in Chicago.

How did I get through this entire article about Seattle and not talk about coffee?! Btw, loved Ghost Alley Espresso in Pike Place Market!

Thanks for reading, friend! If you like what you read from me, you can buy me a coffee to support me.

If you’re interested in learning about how to get out of student loan debt faster, please go follow my own new Medium publication that specifically targets this topic: Tackling Student Loan Debt.

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James Y Kim
ILLUMINATION’S MIRROR

Founder of AlumSum / Status quo challenger / Entrepreneurial DNA / Chicago Booth MBA