Why Youth Can Be an Advantage in Being an Entrepreneur: My Interview with Bailye and Brynne Stansberry

Last week I gave a presentation to a class of undergraduate students from the University of Minnesota’s Carlson School of Management.  The discussion was centered on the topic of failure and how the fear of business failure is relative based on where we live in the world.  The students have spent the better part of the last year working on their startup business ideas and I was impressed with what the teams were able to accomplish and where they had admitted their failures.  During the discussion one brave student admitted that he had felt a fear of failing during the course of launching their student business.  When asked why he had explained that all of the students knew which projects from the previous year had done well and which had failed.  He didn’t want his project to be on this year’s list of failed projects.  He was interviewing with potential future employers and he wanted to be able to talk about his success.

What this student was feeling was completely natural in that none of us want to intentionally feel the pain and anxiety that accompany failure.  But if we take a step back for a moment to appreciate that most new businesses fail outright or at least fail to achieve their set goals then we quickly realize that we will need to get accustomed to failure.  The truth is that there are few safer places to fail than a student startup.  I offered this piece of advice to the student: he wasn’t just building a new business; he was really building a new entrepreneur.  As students, a failed business wouldn’t cost them their retirement money or their home mortgage, it wouldn’t cost them embarrassment with family or friends, and it wouldn’t cost them their job or that next promotion.  They were in one of the most secure environments possible where an entrepreneur could test, try, and fail with little recourse – a place that every would-be entrepreneur was envious of.

As we wrapped up that session I had remembered back to a couple of amazing young entrepreneurs that I had met earlier in the year while I was presenting at a conference in Missouri (See my previous post Taking More Than I Gave: Lessons in Entrepreneurship).  Bailye and Brynne Stansberry are twin sisters who have been working together on their business idea since they were teenagers.  The name of their company is TwoAlity and they are about to launch their first product – a clear rain boot with colorful interchangeable liners.  When I first heard them speak I was blown away by the preparation they had done and the determination that they displayed as they explained how they had come from idea stage to selecting manufacturing partners.   I wanted to talk with Bailye and Brynne a little more to see how as young entrepreneurs they perceived failure and how they addressed any fear of failure.

Q1.  They say that the most important decision an entrepreneur can make is if they will have a partner and who their partner will be.  Like any startup I am sure that there have been some ups and downs along the way.  Do you feel that there is a benefit to having a business partner who can help address any fear or doubt that tries to creep in?  How have you supported each other through this fear?

Bailye: I feel like there is definitely an advantage to having a business partner, especially one that is your twin sister.  We have worked as a team all our lives and we have perfected our teamwork to the point that we know how to work with and handle one another extremely well.  We always joke that we have a unique way of balancing one another.  On days that one of us is questioning our direction or futures, the other one, balances that negativity and brings everything back to usual.  We even balance each other before speeches, meetings, conference calls, and daily work.  People looking in on our relationship are always baffled by our ability to work as a team, and to be honest, most days we are too!

Brynne: Having Bailye by my side is one of the best parts about what we are doing. Because we are twins we have a way of being able to communicate with one another.  When she has an off day, I can help her get out of her funk, and vice versa.  We really have a way of working together and helping each other.

I think one of the best examples is, an “industry consultant”… I use that term loosely… tried to tell us that instead of completing business tasks together, we should divide all the work. For example Bailye be the CFO and me the CEO.  That is the worst advice anyone could ever give us.  We do our best work when we work together. No matter how many people tell us how to make our relationship “work”, only we know how to do that and we are sticking to what we know.  After all, we have been working together for 22 years.

Q2.  Often times young entrepreneurs find help in strong mentors when can help them gain confidence, wisdom, or insight from their experiences.  Were there any strong mentors that have helped you in your journey?  What have they helped most with?

Brynne: I think our strongest mentors have been our parents.  They have believed in us since day one and they set a prime example on how to work together as a team through their marriage and owning a business together.  We could not have had a better example of team work.  Steve Fishman and the TwoAlity team have also been great support for us, through the last 2 years of this journey, mentoring in mainly strategic management and retail.

Bailye: Our dad is an entrepreneur and he has helped us and continues to help us in our journey.  One thing that helped us understand working with a partner, was watching our father and his brother (our uncle) work as a team.  They started Premier Paper and Packaging when we were 4 years old and did a tremendous job of building a successful company and of being role models.

During the video interview we discuss how Bailye and Brynne addressed the subject of failure, what they risked losing most if they had failed, the topic of role models, and their thoughts on roadblocks and perseverance.

What an amazing entrepreneurial story!  If the snow ever melts here in Minnesota I am sure that we will have a receptive audience for their new rain boot!  The boots and boot wipes are actually going to be Made in the USA and the boot liners will be in their home state – Made in Missouri.  You can check them out on Facebook at www.facebook.com/TwoAlity and watch for the official launch of on their website at The TwoAlity Store.

Food for thought:

  • What is holding you back from becoming an entrepreneur?
  • How could we encourage more youth to try their hand at entrepreneurship?
  • Would more entrepreneur mentors and role models help in overcoming our fear of failure?

One reply to “Why Youth Can Be an Advantage in Being an Entrepreneur: My Interview with Bailye and Brynne Stansberry”

Leave a comment. Comments from first-time registrants are moderated.

Signup for Matt's Periodic Updates

Receive periodic email updates from Matt Hunt including his published pieces, updates on his progress, and more!