Entrepreneurship thrives at the intersection of passion, purpose, and perseverance. In this engaging conversation, Paul Swaney dives deep into the entrepreneurial insights of Taylor Kenerson, an athlete-turned-business innovator redefining success on her own terms. From lessons learned on the softball field to building startups that embrace creativity and AI, Taylor shares how values like kindness, communication, and authenticity guide her journey. Whether you are an aspiring entrepreneur or navigating your own career pivots, this episode is packed with relatable wisdom and actionable takeaways. Join us as we explore the mindset and strategies behind turning vision into impact.
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Entrepreneurial Insights With Taylor Kenerson
I am sitting down with Taylor Kenerson, entrepreneur extraordinaire. She’s got a lot of cool things going up in the New York area. I am excited to get to know you. Thanks for making the trip down from the city. Why don’t you tell the audience a little bit about yourself and then let’s get started there?
Taylor Kenerson Shares Her Entrepreneurial Journey
Let’s go. Thank you so much for having me. I appreciate you. A little bit about me, I am an athlete turned entrepreneur. I am still in the mode of trying to figure it out. No one has all their things figured out. I’m very clear on my why and what I’m here to do. That’s my number one driving force. You’re either with it or you’re without it. If you’re without it, that’s great. You can clap from the sidelines.
That’s awesome. What sport did you play first?
I used to play softball. I have an affinity and love for basketball but I didn’t make my high school basketball team. I thought I was good enough, but apparently not. I had to stick with softball and played that throughout high school. I then played a couple of years in college until I realized that softball or dedicating your time to a sport in college takes up a lot of time and you could do something else at that time if you are aware. That’s where my life pivoted. I sunk my teeth into softball and it taught me so many lessons that I’m able to apply to not only my professional life but personally and beyond and excelling in life in general.
What are the 2 or 3 things that you think make a high-performing team from a sports perspective or a startup perspective?
Communication And Teamwork In Life And Business
One of the biggest lessons that I’ve realized at this point in my life is there are many more connections than there are divisions in life. To weave into the sport and how sports relate to life and how you can take the lessons in sports and apply them to business is profound because there are so many layers. You look at the top sports teams in the world, whether you’re looking at basketball and the Los Angeles Lakers or looking at baseball and the New York Yankees. I’m a Yankees fan. It’s a sad season this season but that’s a discussion for another time.
You look at these top-level teams and they have these common factors that are undeniable. One of them is communication. It’s almost communication to a fault where you’re overly communicative. Sometimes, you’re raw. I was on one side of the spectrum of communication where I was too harsh. There’s a way to deliver the message. You could do it empathetically in a way that does want the best for the other person. You don’t have to do it as a jerk. I had to learn that.
Growing up in sports and throwing your helmet, for me, my perspective was, “I’m showing you I care.” The perspective of my coach was, “Taylor, what are you doing? You’re making a fool out of yourself.” It wasn’t until you got pulled to the side. You don’t have to throw your helmet to show you care. You could do it in other ways. Pull the girl or the person to the side and say, “Lift up your teammate.” There are a lot of different elements, communication being one.
Another one that’s undeniable is teamwork. Meaning, it doesn’t matter if you’re the starting shortstop or you’re the starting player on the bench. You’re a player on the team so you have as much value as the number one star player or not. You need to recognize that. If you are the leader and the star player, it’s your job to make your bench players feel like they are as important because they are. That is how you get a team to really do incredible things and do things that seem impossible. You have to get everyone to buy in. It takes every single person on the team to do that.
It’s super interesting. All of the people on the team here that are in North America are in the Military with one exception, which is Ben. He got an engineering degree from Princeton while playing Division I football. I asked him as I was looking at his resume. I was like, “How did you make this happen?” He goes, “My time management skills are top tier,” which is pretty dispositive.
That’s a huge lesson I learned in high school. I went to an all-girls private Catholic high school, which was an experience in itself. I was flipping sneakers to the all-boys high school, which worked out great because you have a target market sitting right there waiting for you. That experience was second to none in shaping how you can level up personally and professionally.
What lessons can you take from the unorthodox path or the road that’s not traveled? How can you leverage that to your best ability? Going to an all-girls Catholic high school, I could have easily gone down the traditional, average path that you see a lot of the alumni going down. What’s your compass, what are your values, and what makes you driven is the gauge there.
This is the first time I’ve gone so deep into someone’s LinkedIn live. You have to tell me if I’m right. I see two startups after school. You then pivoted over to being a project manager, and then said, “I’m going back into multiple startups at the same time.” Can you walk me through the decision-making process to take a detour for the better part of three years to be a project manager before you went back into entrepreneurship?
Pivoting From Corporate Life To Startups
I was a junior at NYU and we needed to get an internship. I had an internship lined up and it was a corporate internship. At that time, for a lot of my peers, this was something that was highly coveted. This was the path that was defined for you to take. Me being me, I was like, “I’m playing sports. I need to check this box off the list in order to graduate. Let me check the box off the list.”
I had this internship and I was a deer and a headlights. It was one of the best experiences in my life because it truly showed me that diving into something will define whether you love it or you don’t. Through that corporate internship, I sat down one day and was like, “My bosses cannot give me a blank check because I will not write any amount to sit here and do this for the rest of my life.” I was so scared. I was like, “My peers are running toward this coveted thing. What am I doing wrong?” That was a really scary moment in my life.
I made the really tough decision to stop playing softball. You dedicate 16-plus years of your life and 4 to 6-plus hours every single day into something. Even playing at Division III level like NYU, you’re not playing at a professional level but you still have that time commitment whether you were playing in games or attending practices.
That corporate internship made me put the brakes on my life and say, “What do I want to do with my time? How am I going to grow if I don’t see myself growing in softball anymore?” I had to come to that realization because the people around me were like, “You put so much time into this. How can you leave something that you dedicated so much time to?” It was not just me, but my family, my parents, the time, and the money. It’s near endless the dedication and sacrifice that they have to make.
It was deciding whether that was going to make me the best person that I could be in sticking with softball and continuing on for the next couple years, and it wasn’t. That’s when I decided, “I got to figure out what I like beyond the softball field,” because I didn’t know. I had no clue who I was beyond the sport. I only knew myself of going to the gym, working out, training, going to games, and repeat. That was it. My life revolved around softball and the sport. There was not even a sliver of thought for something else. I then realized, “How am I going to figure out what my passions are?”
My friend and I started a creative agency but that’s a bunch of BS. Everyone’s got the marketing agencies and all that crap. We were like, “How are we going to really niche down and do what we love?” That’s when we decided to go into the sports world. We saw the amazing things that those high-end, Big 10 sports programs were doing with their football teams and athletic teams. They were giving them media days. They had cool graphics. They had a brand around their sports teams. We were like, “How can we take this concept for the people that are not Big 10s? They’re more on the lower level but they’re still as good. How can we elevate the brands of not only these individual athletes that are playing at a high level but also these teams and these organizations that are at a high level all over the nation?”
What we started to do was do branding, graphic design, and website development for them. We went all over and would do media days. It was so cool. Some of the kids that we worked with a couple of years ago are playing at UNC or they’re in the NBA. We have pictures of them in high school and their media days and them shooting the ball. It’s cool to see how they’ve evolved.
From the creative agency and doing graphic designs and brand-building for athletic organizations, we then pivoted into artificial intelligence because we saw a problem in our creative process. As we were going through these media days, we were taking hundreds of pictures of these different athletes. Let’s say you have a football team. They have 50 athletes and you’re taking 10 pictures of each athlete. That’s a crap ton of pictures to look through.
Building An AI-Driven Solution For Media Professionals
What I and my friend did was build a facial recognition model that as the athletes would arrive at the media days, they would take a selfie, and then at the end of the media day, we would upload all the pictures into our database and it would recognize who’s in the photo. We no longer had to go and say, “This is John.” John is already linked because we had the whole model built out.
From there, we were like, “This is not just a problem in our process. This is a problem in the creative world in general.” If you go to weddings or a bar, you have photographers. They’re always taking pictures of a lot of people. It was like, “I don’t want to look through 4,000 pictures from my friend’s wedding but I want to know the 50 that I’m in. Show me those.” That was where we dove into AI and that whole ability and capability.
That’s an interesting concept. I also see it ended. How did it end?
It ended because back then, it wasn’t the plug-and-play AI models that we have now. We were building the LLMs and everything. It was a tough decision. It was like, “Do I want to spend the rest of my life being an artificial intelligence startup founder?” That’s where I faced the fork in the road and I was like, “No.” This is a great problem and a great solution. We could solve it and fix it. It’s going to take a lot more energy than I feel like I want to give to this specific project right now. I want to continue finding my other passions.” It pivoted away from there. We still have everything built and ready but it phased out. I was fulfilling myself for a little bit and then I recognized there’s something more.
I’m going to bucket that in the win column no matter what. You have a minimum viable product to market.
We had beta users. We had branding. I still have my dashboards. I still look at them. I was looking at my folder of the 50 error videos of feedback. We did the whole thing. Back then, I was 16 or 17 years old trying to figure it out. At NYU, I was eighteen.
What’s the biggest thing you learned and advice you could give to fledgling entrepreneurs?
Something might be perceived as really “large” and successful and might be it for someone else, but is it for you? What you’re working on, is that going to fulfill your happiness and joy? That should be your filter as you move through different projects. You’re going to have so many “big opportunities”, but are those big opportunities going to leave you fulfilled and happy or are they going to leave you with a big bank account? That’s a stark difference because you can have a big bank account and not be happy and fulfilled and then still miss all of those things. That’s what I would leave with.
You can have a big bank account and still not be happy and fulfilled. Share on XMy public service announcement to the private equity professionals out there is they always turn their lives into a box-ticking exercise. They’re like, “If I don’t make senior associate by 1 year out of business school and then VP by the time I’m 30,” or, “If I don’t get married and have 2 kids by this.” They get to 35 and they look back and they’re not happy.
My biggest question is, who gives a crap about that perception? Who cares what the average timeline says you should be doing at this time in your life? It doesn’t matter. I grew up in Hampton Bays, New York. One of our great family friends owns one of the largest trailer and shipping container companies in America, Cassone Trailer and Storage. He started his company selling watermelons on the side of the road.
Long story short, well over a multimillionaire. This is the catch here. Do you know what he would show up to work in? His old fishing shorts and an old washed but dirty white t-shirt. Constantly, people would show up to the office and say, “Where’s the big boss?” We would point and say, “There’s Pete.” They’re like, “Where’s the big boss?” We’re like, “That’s him in the truck right there getting dirty.” It doesn’t matter what the perception is, whether you need to be in a suit and tie. Be yourself and you will carve your own path.
I’m going to push back a little bit. You’re 23 and you’re going to try to raise some money. Let’s say you got out of NYU. Do you need to put a suit on?
No.
You don’t think so?
No.
Say more.
Why are you going to raise money? Who are you looking to raise money from? What’s your product? What are you trying to do? Your appearance has a factor but it’s not the only factor. I wouldn’t recommend you show up in sweatpants, but if you want to have a little fun and you want to put on a pair of cool sneakers, and you want to dress a little differently, I’m all for it.
Your appearance matters, but it is not the only thing that defines you. Focus on the value you bring to the table. Share on XWhat I’ve learned in construction and everything is that you can’t judge a book by its cover. You’re going to miss a lot of opportunities by that. If I judged our family friend Pete by the book of his cover and him and his white t-shirt and fishing shorts, I’m missing out on invaluable lessons sitting across the table from someone who’s doing record deals and is a highly coveted person if I wrote him off as always a gross, old fisherman. That’s my PSA to anyone that might write someone off that doesn’t show up in the suit. Maybe ask why instead of the judgment first.
Balancing Multiple Projects And Stay Grounded
Next question, it looks like you’ve got five things you’re working on. I’m feeling some Elon vibes with that. This will transfer over to either a consultant, a young banker, or a private equity professional staff on multiple things. How in the world do you determine how you’re going to spend your time every week on multiple things without working yourself into a coma?
I worked myself into fainting, not a coma. When I was at NYU running the startups and everything, I found myself on the floor and I fainted. None of my roommates were home. I looked up at the screen and ten minutes had passed. Long story short, I got into breathwork and everything because I realized you can regulate your heart by yourself. You don’t need medication in most cases to do that.
Given that, what do you do to manage? You’ve only got seven days a week and so many hours in a week. What do you do to prioritize to simultaneously be impactful, give all the people on your team attention, and hit your goals?
It first comes with knowing what your values are and knowing what your why is. Getting involved and not getting involved in projects is an easy decision beyond that point. The number five might seem like a lot but each of these things are the building blocks off of each other and are very much interconnected. They might appear like they’re siloed from the outside but they truly are connected.
That is the whole premise of everything that I’m working on. It is to show the world and people how connected we are and doing that through different mediums, whether that’s through podcasting, legitimate science and quantum physics, frequencies, marketing and connecting people to different messages, or running our yoga retreats and having a billionaire and someone that used their last paycheck all in the same room. Newsflash, they had the same problem. They were both unhappy in their relationship. It doesn’t matter what you look like, your checks look like, or your bank account looks like. You can have similar problems.
I’m going to push down a little bit. Walk me through a Monday. What does your Monday look like as you’re setting up for the week? I talked to the junior private equity professionals. They’ll have some long-term assets they’re looking at or themes they’re sourcing for. They’ll have an active deal that they’re working on diligence on. They’re doing either both tasks like recruiting and maybe they market or have meetings with some of the existing partners. Walk me through your Monday and how you segment that out on what I’m assuming are two, three, or whatever assets.
My Monday doesn’t work well without a great Sunday or a great weekend.
My Monday does not work well without a Sunday. A well-planned weekend sets the tone for a productive week. Share on XI agree with you. I spend two hours every Sunday setting my calendar up. It saves me ten hours on the week.
Sometimes, I catch myself even doing more organizing than I do the rest of the week on my Sunday to extra prepare. I even ask myself, “Am I over-preparing and being too stringent with my calendar? What’s going on here?” Honestly, no, because when you’re doing a lot of different things, whether that’s deals or different projects, or working with different teams, you need to have that filter and have that undeniable focus.
I am like a horse with blinders on when I have my themes and my schedules out. My themes are related to my projects and then I have 1 to 3 to-dos per week for each of those projects. That is it. I will die. I will not go to sleep. I will do whatever I need to do in order to get those done. I’ve had the laundry list. We all have those. My to-dos can rack up eons. What are the couple of things each week that are going to move the needle? That’s all set on Sunday. If it’s not Sunday, it’s Saturday or whatever it is before that week hits to prepare. You have to be prepared.
Let me ask you this question, and this is the same for me. I have an unlimited amount of work I could be doing. It’s an infinite bag that you could pull work out of. At what time do you say, “I need to go to sleep,” or, “I need to spend time with my family.”
The Importance Of Values And Compass
I don’t think it’s a number. It’s a feeling and it’s about what is going on in that day-to-day. None of my days look the same. My Mondays are not always retreat stuff and then I go into frequency stuff. It’s very variable depending on what’s going on and what projects are being moved. To your point there, it’s extremely important that you go back to what is your compass, what is your why, and what are those guiding points so that you can then be able to understand what decisions need to be made by you and what can be delegated to others and move forward from there.
By understanding your why, you can understand what decisions you have to make and what can be delegated to others. Share on XI’m going to pivot over a bit. You have at least filled five perceived market caps. How do you determine when you found a market cap that’s worth filling versus chasing something like a fad? I personally think AI is not a fad. It’s a bubble. How do you determine where the market cap is and where to play?
Leveraging multiple levers. What I mean by this is looking at the fundamentals of the market or of the tool. AI is a tool. I wouldn’t say AI is a fad, but I do not think it’s going to be as new as it is now. Everyone’s gung-ho and running about it. AI has been around for 25 years. It’s not such a new thing. It’s new in its applications, the models, what it could do, and all the processing it could do but it’s not a new concept. I would push back. It’s really about diving deep and what are you using the AI for. It is looking at the fundamentals of the market and what’s truly driving that. Is it nice to have or is it a need to have? It is peeling the layer from there.
Another thing is going on instinct. What are your instincts telling you? You can hear a lot of crap in the market, the news, and through conversations, but what is your gut telling you is real? Align with that and follow that curiosity. If your gut’s telling you AI is a bubble or not or whatever that might be, connect with the experts. Go to the people that are saying this thing. Pick their brain and then create your own opinion. Find the answers for yourself. Whether you believe something or not, do the digging. That’s the best way to get your own answer.
I was listening to Andreas on Rogan or somebody else. He was like, “Most founders think they’re late and they’re early.”
That’s where we were with AI with FaceSpace in 2018. We were early. You asked me why we stopped. One of the biggest reasons why is because I didn’t want to be an AI tech founder. Also, a huge reason why is because we were putting tens of thousands of dollars into building the LLM by ourselves because it wasn’t like you could go to Google and plug and play. We could build the gap now probably in a day. Back then, it took us months. We were way early.
We couldn’t explain to anyone the technology we were using. We were saying, “Do you want your pictures? We’re able to recognize it.” It’s not like we were going in-depth on, “We’re using artificial intelligence to facially recognize your features.” We didn’t say that. That is a huge mistake. Maybe we were a little too early or maybe we should have sunk our teeth in and rode out the wave for a little while longer because it was only a couple of years away that the wave took off. Hindsight is 20/20 without anything.
The reason I play in industrials is because I am almost always wrong on timing. I like really boring businesses to work on. I worked on an outsourced highway maintenance business. I worked on an underground utility locating business. The most interesting thing we’re working on is drones. I got to be a little quiet but we’re working on drones for interesting purposes. That’s all for the Military aspect that supported that.
I have a question for you.
This hasn’t happened yet.
Your take on time, I’m really interested. In a world that’s always going so fast and the play is speed and efficiency, how do you balance that with patience but also not laziness?
I tell my team nothing is ever going to happen fast enough for me. Speed matters in business. I read a book when I was nineteen. I don’t even think it’s in print anymore. It was by Bill Gates. It was called Business @ the Speed of Thought. It was like somebody was soldering iron to my brain. It was that speed matters more than anything.
I tell my team, “Do ten things in a week. 3 of them at least are going to be wrong, or maybe 5. As long as you’re not seven wrong, you’re going to be okay.” The big problem I have with the private equity bros in the formal role is they would put things down to the decimal point. There’s nothing in my world that I need to do to touch a decimal point.
There was one thing we did do. We were talking about fund size and the number of positions in a fund where all the positions are at least somewhat correlated because they’re all going to be industrials. It’s what’s the right number of positions. This will go back to time. If you could put 1 position in there and we’ve got 10 people, we could swarm it and we would probably be successful as long as we don’t make a mistake, but that’s too much of a risk. I thought, “We could probably run up to nine assets. We’ve got nine people. You put one person at each asset.” My gut would’ve told me that the number of assets was seven.
Bo and I hired a PhD in math who worked for hedge funds that took all the market data over the years and said, “What’s the volatility drop?” The number was five. That’s the only decision I’ve made in the last few years that required decimal-point precision. We outsourced the work for several thousand dollars. It was the best several thousand dollars I set.
Know when to bring in the extra capabilities or the horsepower that you need to bring in. Focus on training your people. I say this all the time. Immersion is better than Duolingo. I dropped one of our team into a recontracting effort and said, “Figure this out.” I dropped our COO into a new product introduction for a pet food company to set up the whole transformation office and connect 50 people. There are a couple of people that aren’t with us anymore that couldn’t handle that approach. I have had the pleasure of leading many Special Forces and submarine team members who figure these things out. I hire good stock, put them in the right role, and then I get time back.
One of the biggest lessons I’ve learned is flipping my preconceived notions on its head. They’re misconceptions. That whole premise of fast is the way even if you don’t have the skill, that’s the way that you’re going to figure it out. It is getting the F in there and figuring it out. Guess what? You don’t have to know to figure it out. You know that you don’t know and dive in. That’s the way. That’s great.
Given that, and you’ve got lots of starts under your belt, what is one actionable thing you would give a first-time founder when they’re in total ambiguity?
Focus within and not on the external. I feel like in times of uncertainty when you’re overwhelmed, you are always looking outside. It’s so important not just as a founder but as a human being in life that you focus on yourself. I don’t mean always selfishly. Understand what hill you are willing to die on, where are your values, and where is your why.
Knowing that will make every overwhelming experience and every uncomfortable experience a little easier because you are able to have that guiding force and guiding compass. At the end of the day, you are able to put your head down on your pillow and know that you gave it your best shot. Your reputation, values, and principles were way more important than anything else. Being extremely clear on that helps reduce the friction on everything else in life. That’s from professional losses of losing companies, losing opportunities, or even personally losing people in your life. If you don’t have that compass or that support within yourself, you’re going to be lost, whether it’s early on or later on when you’re “successful”.
You talked about values. What are your three most important values?
Kindness is thrown around often, but I truly believe that by leading with and in kindness, you can never go wrong. People say, “It’s so easy to be kind.” Sometimes, it’s hard because you want to give that person the middle finger and you want to tell them to go screw off. You know that those are your values and you’re going to stick in there. You’re going to maybe give them the middle finger in your head but you’re still going to help them out and guide them along. Kindness is a huge one for me. Also, in alignment with that is love and communication.
You can never go wrong when you lead with kindness. Share on XWhy do you bucket those together?
I didn’t mean to. All three of those things go together in order to make a strong foundation in putting your best foot forward to be your best self. Without those few things, I don’t believe that you could be the best version of yourself. You need to have love for yourself in order for you to love others. You need to have kindness for yourself in order for you to be kind to others. You need to communicate to yourself, “What do I like and not what everyone else likes?” in order for you to be able to communicate to others.
It’s this constant dichotomy and cycle within and outside. In that cycle of moving through, what information is the market telling you? Are these random conversations you’re having? What is that inner dialogue? How are you building that foundation to help propel yourself personally and professionally? I don’t think they’re siloed. They’re very much together. For me, there’s no such thing as work-life balance. It’s life. You have a personal life and professional life in the bucket of life. How you move through those things is how you move through those things but there’s no way you can separate those. That’s reality.
It’s intellectually immature to think you can separate those things. At the expense of being offensive, NPCs try to say, “I am done with life at 4:30,” and my actual life starts at that.
It could also be, “‘When are you going to retire? It’s like, “You don’t like something enough that you never want to retire? I’m sorry you’re even asking me that. I’m offended.”
The firm joke is that I’m going to be 80, hopefully, and God willing, and I’m at a board meeting. I don’t wake up in the hotel room and somebody goes, “Where’s Paul?” They got to call the manager and they’re like, “Hey.” They got to notify my family. I’m not going to work 60 to 80 hours a week at that age but I can imagine myself stopping.
I made a tweet a couple of months ago that said, “My biggest fear in life is being irrelevant.” That’s why I always tend, for example, you to always invest in people fifteen years younger than me. There’s a guy named Ryne that was on the show. I encourage you to check that out. He is an amazing guy. He’s going to get the best role. My plan for that guy is he’s a CIO at 35 of a big company.
To expand on that one point, investing in people 15 years younger and also 15 years older and pushing the investment definition beyond financial. It is investing in time and conversations and having those conversations. Most of my friends honestly are 30 and older. The majority of the people that I talk to daily are 70 and older. I don’t talk to people who are in their twenties because what are we talking about? Do you want to talk about going to a club and drinking? You can only do so much of that in your life. To your point, it’s really important that you expand yourself both up and down.
I had Bo, our COO, on a call with a CEO who worked with me at an asset that we had this could-not-be-better exit at. I missed him. I haven’t seen him on video in 2 or 3 years, probably since ‘22. We’re trying to pull him into an asset that we’ve got locked up. Bo gets out of the meeting. This guy’s somewhere in his ‘60s. I don’t know because he has so much energy. Bo goes, “That guy is awesome.” If you happen to be listening and you’re in a later stage career, you can find the right bunch of younger people who will invest in you, respect you, and ask your opinion.
The majority of my biggest mentors are seventy, seventy-two, or seventy-four-year-old, unfortunately, men.
That must be energizing for them.
It’s a mutual thing. It’s two sides of the street where both values are being exchanged mutually.
I was reading a medical center study. It was that relationships are what keep you alive and anything else. It’s not drugs or medicine. They were saying even if you’re the crotchety old man who makes jokes with the mailman, goes over there to the barbershop, and is belligerent, that will still keep you trucking.
I want to go back to values. I’m going to ask you for your feedback live. These are the core values of the Swaney Group. Number one, distinctive investment results. We rescue broken businesses and turn good companies into legacies. Number two is authenticity. We are always our whole selves. I bucket this with kindness. We do not hide from conflict. We do not obfuscate results.
That’s a huge one, not hiding from conflict. That’s super big. I’ve seen the strongest and most valuable collaboration come through immense conflict. How you got through that is communication. It goes back to that. Our beginning, weaving it back to the first question that you asked me, is, “What are those common elements of championship teams?”
The strongest and most valuable collaborations come through immense conflict. Share on XThe founder of the firm I was at before, we had this offsite with the asset that this guy Bo and I were talking to. He made a stink in my strategy meeting. He came up to me afterward. They were not yelling but there was a heated discussion. He comes up to me afterward and says, “Paul, I’m so sorry.” I was like, “Some people do work to avoid conflict.m. I drive conflict to avoid dumb work.” It was great. That was two. Number three is trust in the team.
None of those matter if the team’s not bought in. You can have a bunch of crap up on the walls as values. If you could get your team to buy into those values and live, die, and breathe by those values, it doesn’t matter what those values are.
Number four is speed and agility. We work harder and faster, not longer, than any other firm. We make trade-offs to deliver maximum value.
When do you know when to make the sacrifice? Do you have a compass, values, or principles?
I’m such an intuitive person. If you Myers Briggs me, I’m the hardest core and I float on my gut. We’re putting in route optimization software at a company we’re advising. There are five different options. Guys make a call, get it out as fast as possible, and prove the concept. The other constraint is the techs don’t really want to be micromanaged with which spot to go but it’s going to save 17% in fuel so it’s meaningful. At some point, it’s like, “Do a pilot. If it works, we can go.” We got to be respectful but I don’t mind stepping on a couple of toes to get something done and then they can watch it on the backend. The fifth one is accountability. We own our actions and deliver on our promises.
It’s a hard thing to not be accountable for yourself. We are our biggest negotiators and lawyers. We could talk ourselves in or out of anything. It could be our own mind. Are we being accountable for ourselves?
The mental gymnastics I’ve seen senior executives go through to not pull the trigger on something or pull the trigger on something like confirmation bias. This guy I knew got me a list of logical fallacies. It was a poster on the wall, the confirmation bias that some people have. This is the last one, and this one is my controversial one. Fun. We get things done and celebrate our wins.
What’s controversial? Is that cutthroat?
Maybe. If you saw that in a pitchbook, what would you think?
If that’s the kind of people I want to be aligned with. Also, others see that in a pitch book and they are running away. That’s exactly how you can weed out the people you want to be around.
This is the second last question. What has been your toughest growth challenge and how did you push through it?
Navigating Loss And Using Reflection To Grow
It’s still something that I deal with often, which is loss and the relationship with loss in the moments of loss, whether that’s a person, a project, or an opportunity. It’s only emotion. A growth challenge for me has been distancing myself from those emotions to provide the best reaction. Not every reaction should be emotionally driven.
In navigating that, it’s not necessarily a deer in the headlights challenge but it’s something that I actively work on. I am trying to separate myself from the emotions and what’s going on. There’s a framework that I revert back to a lot. It’s E plus R equals O. It’s Experience plus Reaction equals Outcome. You can have this experience but how you react is everything. Being tied to it but also not and also being able to take the lessons from it is extremely important and something that I avidly work on daily.
Give me an example. Maybe you were approaching feeling despondent or unsuccessful. It’s okay to stew something for a couple of hours and then get over it. Tell me the specific situation and then walk me through your response.
There was a particular moment about a couple of months ago. I’m scriptwriting. I wasn’t feeling comfortable with the scripts I was delivering. I knew this and I kept delivering them. It was brought up to my attention like, “Taylor, can we have this call about this?” We had a call about it and we were on two different pages. We had to work through these weeds and I didn’t understand some of the elements that were being portrayed in the writing.
Diving into those weeds and understanding the depth of what you’re putting out there can be translated differently. Where is that gap? It is being able to fill that gap, whether that’s verbally or in communication. My biggest lesson in that goes back to communication. Be upfront and be communicative. If I was feeling weary about something, be upfront and work through that right away instead of going through the deliverables.
This is the last question I ask everybody. What’s the most impactful book you’ve ever read, and how did it affect you?
What really shifted me was reframing my thoughts on books. I always thought it was like, “Teachers are assigning it so they’re all a bunch of BS,” until I realized, “You can read books that are amazing and impactful.” That’s when I shifted my thinking. There’s one that’s called The Body Keeps the Score by Bessel van der Kolk. It relates the mind and the body and how different experiences throughout your life shape your path, whether they’re consciously known or unconsciously known.
People that have PTSD, for example, in the Military, oftentimes, it’s not because of one experience. It’s a compound. It’s many layers of experiences or conditional thinking. The book gives you a holistic viewpoint of the different traumas and experiences you have in your life and one way to think about them. That was a great framework and tool in my life, especially because I’ve had a mother who had breast cancer. Understanding that breast cancer could be attributed to other things like trauma in your childhood and stuff like that. It was an impactful book that shaped my thinking and connected me more to that inner person who is huge in identifying your compass and your values to help you be the best person outside of yourself.
It has been lovely getting to know you more here. Where can we find you? Where can people get in touch with you? The most important thing for a startup is the team. I’m giving you my personal stamp for investing in. Where can investors get in touch with you? Where can people get in touch with you? Let us know.
You can find me on LinkedIn as Taylor Kenerson or on X as @TKenerson_. Follow me on the podcast. You can find me anywhere and search me up.
It has been spectacular getting to know you. I am looking forward to getting a snack later. Please let us know if there’s anything we can do to help your success.
Thank you.
Important Links
- Connecting U
- Taylor Kenerson
- Taylor Kenerson on LinkedIn
- @TKenerson_ on X
- The Hyperengage Podcast
- From MLB To Millions: Ryne Ogren’s Leap Into Business [S2: E4]
- Business @ the Speed of Thought
- The Body Keeps the Score