Kathryn Jackson ’11: From Entrepreneur to Consultant

A headshot photo of Kathryn Jackson, smiling.
Kathryn Jackson

Kathryn Jackson ’11 is perfectly suited to help entrepreneurs. Because she’s literally been in their shoes.

Jackson started Protect Your Pumps upon graduation and earned national attention for her innovative high-heel product. After eight years, she was ready for a change, closed the business and pivoted to small business consulting.

Today, she is a consultant for the Wisconsin Small Business Development Center (SBDC) in Rock County, providing free, confidential assistance to business owners, especially those hurt by the pandemic.

Learn more about her achievements and journey in the below Q&A:

What drew you to law school and University of Wisconsin Law School in particular?

Both of my parents graduated from University of Wisconsin Law School: Donald Jackson ‘77 and Celia Jackson ’80. So, I grew up in a home with two lawyers. Plus, many of my close family friends are lawyers. To say that I was often a witness to spirited and engaging debates would be an understatement.

Even as a child I was always drawn to the idea of getting to the bottom of something, doing what was right, fighting for justice and using my voice to advocate for others. Because of this, I thought law school would be a good fit for me. I went to UW because of the connection my parents had to the school.

What was most memorable about UW Law?

Some of my best memories were tied to being in the Black Law Students Association (BLSA) and the community I created through that organization. I was very involved in BLSA. I often traveled to the regional and national conferences and participated on the BLSA Mock Trial team. Those events were a great way for me to build meaningful relationships with other Black law students.

What was your biggest takeaway from your time here?

I’ve learned to be confident in my own journey. I graduated law school over 10 years ago, and I’ve never practiced law a day in my life. I used to beat myself up about that. However, I’ve grown to appreciate my time at law school. Even though I’m not practicing, I still gained tremendous amounts of value in going to law school. I acquired important skills during law school that have supported my journey as an entrepreneur and business consultant.

You hopped into entrepreneurship right after law school. What inspired you, and what were those first few years like?

I started Protect Your Pumps in late 2011, about five months after I graduated from law school. During my last two years in law school, I worked part time as a team leader at the Gap in West Towne Mall. It was there that I fell in love with business and the idea of running my own business. In that job I was able to get a lot of hands-on experience in customer service, learning how to sell – or more importantly, understanding why people buy. I also managed staff and measured business metrics.

At the time, I didn’t recognize it; however, this was probably one of my most transformational work experiences because it planted a seed. After graduation, I moved to Chicago and started working in retail sales at Neiman Marcus. It obviously had nothing to do with the law. It continued to feed by interest in business.

While I was working at Neiman Marcus, I sold a lot of really high-end products, including designer high heel shoes. A lot of customers would complain about the soles of their shoes getting damaged quickly. At that time, the only solution I had to offer customers was to resole the shoes. That was expensive, and it didn’t always look that appealing because you would have to cover up the original sole. I found customers buying high-end shoes wanted the original soles to remain intact.

“I know firsthand how challenging and rewarding it can be to start a business.”

At the time I was reading a book by Tim Ferriss, “The 4-Hour Workweek,” which talks about starting a business. He explained that the best businesses are ones that find solutions to problems. At that moment I decided I was going to find a solution to the problem my customers were having with the soles of their shoes. I began working with manufacturers to get sample products, and Protect Your Pumps was born.

The first few years were a whirlwind. A lot of trial and error. I really had no idea what I was doing, but I was determined, and I was moving really fast. I hit the ground running. I was sending product samples to magazine editors, TV producers, celebrity stylists, anyone with influence. I was determined to learn how to market on social media. About 18 months in, I started to get traction. At that time our e-commerce business started to ramp up, and we grew an international customer base.

You won the Wisconsin Small Business Administration’s Young Entrepreneur of the Year Award in 2015. How did it feel to receive that kind of recognition?

It felt great. I had been working so diligently since I started the business, and I was having some success at that time–and it felt really good to be recognized. Many of my family and friends attended the awards breakfast, and I threw a big party in Milwaukee to celebrate, which was a lot of fun. It was an exciting time because I was also getting national recognition. Around that time, Protect Your Pumps was featured on the “TODAY Show” and in Shape magazine, and I was profiled by Google as a featured small business.

You pivoted to consulting with WWBIC and then the SBDC. Why did you make that change? And how important is your own startup experience when working with clients?

I started doing small business consulting because of my former consultant, Athena Agoudemos. She now works as the SBDC director at UW-Milwaukee. She was incredibly supportive while I was building Protect Your Pumps. After I closed my business, she encouraged me to explore consulting because she thought I would be good at working with entrepreneurs.

My experience helps me tremendously when working with clients. I know firsthand how challenging and rewarding it can be to start a business. When I give advice or guidance, it comes from a genuine place with real life experience.

What did you ultimately do with your business, and why is that a good lesson to share with other business owners (if at all)?

I closed my business in early 2019. I was ready for a change. In retrospect, I wish I would have explored selling my business. I had a couple of people express interest. However, I felt overwhelmed by that process and didn’t think I was in a good position to sell. I just didn’t know enough, and honestly the unknown terrified me. I encourage business owners to think about their exit strategy early on and be open to exploring all methods, especially ones that will put you in a better financial position.

Can you talk about your current Rock County role specifically? What is it like helping business owners? What do you enjoy most?

I’m currently a business consultant in Rock County. I mainly work with business owners in that area who have been impacted by COVID. I do a good deal of outreach, so I have frequent meetings with community stakeholders to share about the SBDC services. I spend most of my time meeting with business owners to support them and provide one-on-one technical assistance. I enjoy working directly with entrepreneurs and being their champion.

I also enjoy planning educational programming to support business owners in their professional development. This job also gives me the opportunity to advocate for small business owners.

What do you like to do outside of work? Any personal achievements you want to share? Anything I didn’t ask that you want to share?

Outside of work I enjoy spending time with my family and friends. I also love to bake. I’m finishing up a pastry program at MATC, which has been a ton of fun!

Interview by Jennie Broecker