Kyle Bergman of Swoveralls: 5 Important Business Lessons I Learned While Being On Shark Tank

Posted on

Be kind to yourself — While I was bummed I didn’t make a deal, I learned not to beat myself up over it. I did and said everything I wanted to, and have no regrets for how my episode went down. The amount of variables involved in any given goal makes chance a critical part of the game we play. Understanding that luck and timing are valid factors that can be your best friend and worst enemy is important, but also know that in order to get lucky you have to continue to show up….and so I’m a big believer in the old saying that the harder you work the luckier you get.

As a part of our series about the ‘5 Important Business Lessons I Learned While Being On Shark Tank’ I had the pleasure of interviewing Kyle Bergman.

Kyle Bergman is the Founder and Chief Swoveralls Officer at Swoveralls (www.swoveralls.com). Swoveralls is a digitally native brand whose purpose is to create the world’s comfiest products using sustainable resources and ethical manufacturing methods. Their hero product, Swoveralls, is the glorious combination of sweatpants and overalls into one incredibly comfy masterpiece.

Thank you so much for doing this with us! Our readers would love to “get to know you” a bit more. Can you tell us a bit of the backstory about how you grew up?

Born in NYC, grew up mostly in Connecticut and then Toronto, CA where we moved when I was 16. My Dad is an entrepreneur, and my Mom has worked in retail/fashion her whole career, so you could say the apple definitely didn’t fall far from this tree. Always been an athlete, and played division 1 lacrosse at Drexel University, and was lucky enough to play post-college on the Israel National Team, representing the country in 4 world championships. I worked in the corporate world for 6 years after college, and then got my MBA from NYU, where I am now an adjunct professor teaching two undergraduate classes, one on supply chain, and one on general management principles. I am also a certified fitness trainer and triathlon coach, and coach part-time in the city. When I’m not doing any of the above…I am most likely hanging out with my Wife Elizabeth, or training for an upcoming triathlon race!

Can you share with us the story of the “aha moment” that gave you the idea to start your company?

My friend shared an article with me about Sweatpant Overalls, but they didn’t really exist in the traditional way you or I would think (or what Swoveralls now provides :). So when I googled sweatpant overalls I was disappointed to find there wasn’t anything to buy, however I did find a supplier that was willing to produce them. The big aha moment came when I used google’s keyword search planner tool and discovered that about 500 people per month were also googling sweatpant overalls just like me. That’s when it went from being a personal problem to a business opportunity.

Can you share the most interesting story that happened to you since you began leading your company?

Most interesting story — I think it’s currently in motion! The people I’ve met, the customers we’ve made comfy…there isn’t one particular story that stands out as most interesting, so I’d say we’re still writing our most interesting story in real time, but a great moment I’ll never forget is when a TSA agent asked if I was wearing Swoveralls back in 2018 on a flight back from visiting our suppliers in LA. The brand was like a year old…and so to have a complete stranger across the country identify our product that I was wearing through the airport was such an awesome feeling.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

It’s funny now..but wasn’t at the time. When we were first buying fabric, we needed two kinds — 1 type was for the body of the Swoveralls garment, and what 90% of the product is made out of. The other type was rib knit, which we use for the jogger cuffs, about 10%. Well we bought 50% of each, and as a result had literally YEARS of rib knit fabric that we just had to sit on. ​​However a couple years later once we grew a little more we decided to make Swoveralls entirely out of the rib knit, which turned out to be a hit! Lesson — I love to ask, are there any other questions you think I should be asking? Or, what would you do if you were me? If I’m in a situation that is new to me. (Include rib knit link)

Are you working on any exciting new projects now? How do you think that will help people?

We have a bunch of exciting new Swoveralls styles in the roadmap. We have almost finished planning our new launches for next Fall, 2024! Creating new Swoveralls styles gives us an opportunity to do 3 things 1.)- improve our existing offering based on customer/market feedback, 2.) engage completely new customers who may not have been interested in what we currently offer or didn’t know about usz for example, new corduroy launch (link) and 3.) maybe the most important — provide additional opportunities for our existing and most loyal customers to grow their comfy collection 🙂

It’s not just about making new comfy stuff though, a large part of my job is storytelling. I live and breathe Swoveralls. I wear them everyday, and not because I feel like I have to, but because I genuinely love them. As a result, I am the company mascot (you can see me on TikTok here) and love creating fun and informative stories to generate awareness that yes, sweatpant overalls do exist, and we have been waiting do you 🤗.

Ok, thank you for all that. Let’s now move to the main part of our interview. Many of us have no idea about the backend process of how to apply and get accepted to be on Shark Tank. Can you tell us the story of how you applied and got accepted? What “hoops” did you have to go through to get there? How did it feel to be accepted?

I met one of the casting producers through a mutual acquaintance, and then submitted a short audition video, then was connected with some producers who helped me craft my pitch and get my set ready. Very stressful as the entire time they could drop you at any point, and even once you film your episode could never air! Even once accepted and once aired the stress didn’t stop because we didn’t have inventory and you’re dealing now with a ton of customers. It was a wild ride and I have no regrets, but some companies have a little more infrastructure or inventory than we did when airing, and some I imagine were on the other side. It’s a great feather in our cap to say we aired, but it doesn’t define our brand.

I’m sure the actual presentation was pretty nerve-wracking. What did you do to calm and steel yourself to do such a great job on the show?

Yes I was nervous right before going out, and I did a handful of push-ups right outside the door before it opened. I need to expend some physical energy as taking deep breaths wasn’t really working, ha! In a lot of ways I had been practicing it for that moment for a while- I was (and still am) a part time group fitness coach in NYC, and so I am comfortable presenting on a mic in front of groups of people. Also I had a bunch of investor meetings before the show so knew how the conversations typically go. So it was really helpful to have had some lights and camera and serious investors experience before I went on.

So what was the outcome of your Shark Tank pitch? Were you pleased with the outcome?

I didn’t make a deal, and didn’t even receive an offer! I was really bummed at first. I had wanted to make a deal with either Cuban or Lori because I felt they had the most relevant skill sets/network applicable to my business, and I’ve also heard other entrepreneurs enjoyed working with them. I was also upset because I knew not making a deal or even receiving an offer can decrease the likelihood that you even air. So it was scary to think of all the time and energy I invested at that point, and how it could all be for no air time. However, once we found it we would air…it was incredible to still own 100% of the company. While a part of me wonders what could have happened if I made a deal…I’m happy with the way things have turned out.

What are your “5 Important Business Lessons I Learned While Being On The Shark Tank”? (Please share a story or example for each.)

  1. Know your numbers — Establishing credibility is an important part of developing trust, and the Sharks (and any investor for that matter), is going to rely on you to know your stuff..or how could they invest? Making sure you know every aspect of your business is critical
  2. Life is about who you know — Knowing your numbers is important, but being
  3. Be kind to yourself — While I was bummed I didn’t make a deal, I learned not to beat myself up over it. I did and said everything I wanted to, and have no regrets for how my episode went down. The amount of variables involved in any given goal makes chance a critical part of the game we play. Understanding that luck and timing are valid factors that can be your best friend and worst enemy is important, but also know that in order to get lucky you have to continue to show up….and so I’m a big believer in the old saying that the harder you work the luckier you get.
  4. Enjoy the journey — The shark tank journey lasted about 9 months from the moment I was introduced to the casting producer to the moment it aired on TV. I am glad I took some moments on the way to stop and just let the experience sink in. You only get to the top of the mountain you’re climbing once, but you can pause so many times along the way and be proud of yourself for how far you’ve come. I can and will still do that more often.
  5. Go after your ideas — I made it to Shark Tank because a friend sent me an article about sweatpant overalls. It seems crazy, but much crazier things have happened with much bigger outcomes. It’s incredibly empowering to see a dream realized, and the best part is that it will give you a ton of positive momentum in building on the traction and success and network you will have built. The hardest step is often the first one, but if you want to do something bad enough, then I think you can do it!

What advice would you give to other leaders to help their team to thrive and avoid burnout?

Burnout these days is almost inevitable. We live in a hustle culture, and instead of avoiding burnout, I think it’s more realistic to make sure you identify what led to it, and make sure to protect yourself in the future. Similar to falling as you learn to walk…if you super ambitious and want to be a business owner, it’s really really hard not to overextend yourself, so just make sure you adjust appropriately when you hit a burnout roadblock.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-).

As an endurance athlete (marathons, ironmans, etc.) — I think everyone would be so much happier if they were able to move their body. A ton of people understand the value of exercise, and it’s a multi-billion dollar industry, but if I could give everyone the ability and time and space to run so they could experience a runner’s high…I think that would bring a ton of good to a ton of people.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Failure is not an indication of inadequacy. Failure is simply an indication that there is a gap in your current understanding, timing, or skill set. Therefore, failure in one instance can be remedied by more work, understanding, and perseverance.” An old professor shared this quote with me, and it came at a time when I needed it. To me, this makes failure not only not scary, but it also makes it exciting as it’s a learning opportunity.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

I would love to have breakfast with Gustav Iden and Kristian Blumenfelt — they are the two dominant athletes in the Ironman world right now. They inspire me to push myself more physically, which also pays huge mental dividends as I am able to work with a clearer mind. And they both have a funny sense of humor that would make the meal entertaining.

Thank you so much for joining us. This was very inspirational.


Kyle Bergman of Swoveralls: 5 Important Business Lessons I Learned While Being On Shark Tank was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.