September 8, 2022

"Ok, But How" with Founder Phil Terrill of SoleSafe

We hear how Phil Terrill turned his passion for shoe collecting and insurance industry questions into SoleSafe


Elyse Ash

Elyse: What did you want to be when you grew up? Did you always know you wanted to be an entrepreneur? 

Phil: When I was growing up, I wanted to be an architect. I remember always building things like Legos or model cars as a young kid. I even took technical drawing classes in high school in prep for undergrad where I planned to start the journey of becoming an architect. While I didn’t always know I would be an entrepreneur, I did have an idea about creating something of my own.

Our family has always had people with their own businesses, so I figured it would be a matter of time. I actually have become an architect both in my former life at Microsoft and now as a full-time entrepreneur with SoleSafe.

Elyse: How did you get the idea for SoleSafe? 

Phil: I have always loved sneakers, which most people that know me can attest based on my collection. SoleSafe was born out of my inquisition and wanted to challenge a sometimes archaic industry like insurance to provide something more specific to the sneaker community.

What started as a few questions to my insurance agent about my wife’s engagement ring turned into a series of queries about my sneaker collection. I remember the exchange making me feel like I was speaking a different language and that nothing was available in the market at that time to directly protect the investment and value of sneakers.

Photo of SoleSafe Founder Phil Terrill in his shoe closet surrounded by sneakers carefully organized and curated

Elyse: How did you start building SoleSafe? What pieces of the business did you build first? How did you fund those first phases? 

Phil: On a piece of printer paper. I sketched the initial user flow without doing a ton of research as I didn’t want to influence my thinking with outside perspective too soon. Then I started getting more focused on doing market research and digging into what might be available for our targeted consumer community. Right after that, I started the process of getting trademarks including sneaker insurance.

From there, it was all about building a prototype. I tapped into my tech ecosystem to find the right outsourced development team. I struck gold as they are amazing and we started building SoleSafe (the mobile app).

We self-funded the beginning product and was successful receiving a few grants that helped with development. This became important when going into future fundraising conversations with our current team of investors.

Elyse: What was some of the most helpful feedback you received from users of SoleSafe?

Phil: Build for the total experience not just what will make money. Continue thinking about removing friction with simple steps versus sophisticated, overthought user interfaces. Create a community in the platform beyond insurance. 

All of these are high-level points that informed our design thinking of the current mobile experience. Additionally, we made a decision to build vs. buy a policy and claims administration portal which will provide a strategic advantage in the future.

Screen shot of the SoleSafe app loading an insurance quote on an iPhone

Elyse: What has been your biggest success with SoleSafe to date? 

Phil: First, as a husband, getting the vote of approval from my wife to quit my plush job at Microsoft and pursue a dream. That’s a different type of investment and capital you need to do this especially when it’s tough. So, I am very grateful all the way around.

As a CEO, I would say finding really incredible people to join the team. Working with Corey, Trevor, Yazmin, Silas, our dev team, and advisors has been such a blessing. It lets me know as the “architect” that other people see what I see and want to “get in the mud” with me to make it happen. That is really cool.

As a now solo founder, a black-male founder, a midwest founder, a first-time founder, a scared founder, I would say raising our pre-seed round.

We have a really diverse mix of investors which make it easier to get things done on a daily basis. They poured into a dream, made a calculated bet, and let us move. In total, we raised just over $1M while building the company in a dope, sports-tech accelerator with the Minnesota Twins & Techstars. 

Phil Terril standing on home plate at Target Field where the Minnesota Twins play baseball in a SoleSafe jersey

Elyse: What was your experience like as a member of the Minnesota Twins Accelerator

Phil: Epic! The experience was epic in every sense of the word. Yes, I raised capital but I met some really amazing founders doing wild things and making it happen every day. Each one of them have crazy superpowers that work for their companies and I cannot wait to see their continued success.

For me to experience a program that allows me to sit naturally at the intersection of sports, tech, culture while being in my backyard (SoleSafe is a Minnesota-based  company) was special.

Elyse: You spent quite a few years working at Microsoft. How did working at an enterprise company help prepare you (or not) for running your own business?

Phil: Microsoft was a game changer personally and professionally. I was able to experience some unimaginable moments while at arguably one of the best corporate companies on the planet. I started in cloud sales and account management my first couple of years. That was an invaluable experience to really hone my ability to hustle while building genuine connections at all levels with my customers and partners. Towards the end of my time at Microsoft, I was able to build, lead, and manage programs with global responsibilities.

Going through budget planning, hiring processes, vendor selections, travel, and more provides a perspective needed to run a company. That exposure helped craft my view of global business, investing in team culture, and having fun along the way. One of those experiences was working with the Microsoft for Startups team as business partners. You really get to see how creating value can dramatically accelerate the trajectory of early stage companies. But all in all, Microsoft changed my life and I am forever grateful to everyone during that chapter of my life. Now, I get to transfer all of those experiences, relationships, and tools for the advancement of SoleSafe. There have been many times over the past two years with SoleSafe.

Elyse: Do you have any advice for founders who want to disrupt legacy industries that can be notoriously hard to break into, like insurance?

Phil: Persist. The journey to disrupt and do something fresh and new is really hard. Persistence despite the resistance is what you need to keep in your mind. If it wasn’t hard or had a high barrier to entry (like insurance) it wouldn’t be worth the work. The other would be to stay committed to your “why” as many of these legacy industries will catch on. Don’t compromise the integrity of your core product, service or dream. 

A screen of the SoleSafe app on an iPhone showing how much someone's personal collection is worth

Elyse: What advice do you have for first-time founders in general? What do you wish you could tell younger you?

Phil: The hardest part is getting started. If you have a dream or idea, go for it. If you don’t you might kick yourself later for not giving yourself a chance. I received tremendous value in getting involved with local accelerators that didn’t take equity and provided a safe space for founders.

Oftentimes I see founders trying to fight the war alone and while that is commendable, starting a company is a team sport. Your tribe will be your cushion, so keep them in the loop along the way. A younger me would appreciate hearing to embrace the highs and lows. If viewed with the right perspective, they can be perceived as gains. Embrace both full throttle and with open arms. Each has a different value and are building blocks to the ultimate destination you see for your company.

Lastly, find your space to recharge and disconnect. Each day I work on this and strive to get better at being honest about where I am at mentally, physically, emotionally, and spiritually to ensure I can show up to lead, listen and move the needle that much more for SoleSafe. If any of those feel depleted, it can be a signal to take a moment for you.

Just know that it’s all good. This is a long road, so be the best version along the way.

Elyse: Imagine you can only save 5 pairs of shoes from your own personal collection. Which 5 are you saving?

Phil: Ahh, that is a tough question but here is what I came up with. First, I would keep my first pair of Jordans (Air Jordan 5 Fire Red with original tin can box). The others would be Jordan 11 Space Jams, Jordan 1 Breds, Air Max 1 Anniversary Red, and an all white pair of Air Force 1s (need a classic).

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Elyse Ash is a marketer, creative, writer, speaker, founder and loud laugher. In her free time she enjoys playing with her kiddos, going to new restaurants, reading and pretending she’s into yoga.