You’re a St. John’s grad and have spoken about John Gagliardi being an inspiration, particularly his quote about ordinary people doing capable of doing extraordinary things. Did you ever meet him?

My time as a student overlapped with the last couple years of John’s tenure coaching at St. John’s. He was something of a living legend and his 60 years of coaching at the school was sewn into the identity of St. John’s and what it meant to be a Johnnie. During that time, we’d often cross paths on campus and chat, but I knew him more through stories from his players than my personal experience with him.

A great brand usually starts with a great name and Hippy Feet is fantastic. How did you land on that?

The “Hippy” in Hippy Feet is our nod to the original hippie movement in the 60s and 70s. Aside from being a culturally vibrant time, we wanted to draw on some of the ideals that were foundational to that cultural movement. Specifically, we look to it as a time period where there was a deep care for people and the planet. Those are the same values that we built our company on — helping people in need and be environmentally responsible at every turn.

You started out with a buy-one-give-one away proposition in delivering socks to the homeless and shifted to providing employment opportunities. When did you know you should shift?

One day, my co-founder and I set out to the streets of Minneapolis and St. Paul with the back of his Honda Accord packed full of socks to donate. At the end of the day, we had an empty car and fulfilled our promise to our customers to donate a pair of socks for every pair sold, but we were also left with a guilty feeling. We had done exactly what we told our customers we would do, but we saw too many familiar faces from our previous trips to donate socks. It hit us that all we were doing was providing a band aid fix. Those familiar faces all belonged to people who were still homeless. We needed to provide a more meaningful impact and help people actually get back on their feet. The development of our employment program soon followed. Hippy Feet was growing and that growth gave us the resources we needed to go beyond a superficial act of giving and make a more fundamental change in peoples’ lives.

You’ve spoken about how entrepreneurs should jump in and test their proposition and adjust rather than spend too much time trying to perfect every detail. How do you help entrepreneurs overcome this fear?

Even the most planful of entrepreneurs will look back on the decisions they made early on and ask themselves “what was I thinking?” The testing and failures are going to come whether you’re ready for them or not. By getting your offering to market quickly, you can get actual customer feedback that is going to inform the direction of your business. Aspiring entrepreneurs often disregard how powerful three or five years of consistent effort can be. The vast majority of businesses are better off getting that clock ticking sooner than later.

Launching and running your own business is so much work. How do you guard against burnout?

I learned this the hard way. For the first three years after launching, I was consumed by Hippy Feet. My relationships, health, and sanity suffered. It finally hit me that this wasn’t sustainable, so I backed off a bit out of necessity. That’s when something special happened. I could finally see the forest for the trees and the quality of work and business decisions I was making significantly improved. Some things in business are mission critical, others are just nice to have. The nice-to-haves shouldn’t come before your well-being.

When you launched you distributed 20,000 socks to the homeless population. How many have you distributed by now?

Once we hit the 20,000 pair donation mark, we actually dropped our formal buy-one-give-one program to focus on employment instead. We’ve probably donated another 10,000 pairs or so since then, but the job opportunities are the important part. We’ve been able to provide transitional job opportunities to over 160 young people affected by homelessness. We can proudly say that many of these people are no longer experiencing homelessness and credit our program for playing a role.

What kind of jobs and job opportunities does Hippy Feet provide?

When you order socks from Hippy Feet, your products have a number of different touchpoints with the young people in our employment program. We provide jobs through product assembly, packaging, fulfilling e-commerce orders, and managing our warehouse. We work with youth (ages 16-24) who are experiencing homelessness, providing them jobs in a 6-month program. They have the opportunity to earn a safe, legal form of income, and also get access to other resources like job certifications, bus passes, and counseling.

Who inspires you in the business world?

I’m most inspired by my team at Hippy Feet. I’m frequently floored by the creativity and passion that each person brings to the table and I don’t think that can be matched by looking to a larger organization for inspiration. There are a lot of situations where there is just as much to be learned from individual contributors as there is from some of the iconic entrepreneurs that get the spotlight.

What is next for Hippy Feet?

We’ve been able to expand the company’s sales footprint nationally, and we need a giving model that matches. We’re currently working on standing up non-profit partners in other areas. That way, if you buy a pair of Hippy Feet socks in another part of the country, you’re helping a young person in your area. I want to keep things feeling small and personal even as we grow.