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From Athlete to ESPN Host and Investor: Forging Your Own Entrepreneurial Path

Jay Williams
Business Owner, Former Athlete, Broadcaster at NBA, ESPN
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2020 Startup Grind Global Conference
February 11, 2020, Redwood City, CA, USA
2020 Startup Grind Global Conference
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From Athlete to ESPN Host and Investor: Forging Your Own Entrepreneurial Path
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About speakers

Jay Williams
Business Owner, Former Athlete, Broadcaster at NBA, ESPN
Derek Andersen
Co-Founder at Startup Grind

Jay Williams – former No. 2 draft pick for the Chicago Bulls – is a trailblazing athlete who forged his own entrepreneurial path. In addition to being a partner in ESPN’s “The Boardroom” and co-owner of Simatree, Jay is an investor, ESPN host, NBA analyst and New York Times bestselling author of “Life is Not an Accident"

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Derek co-founded Startup Grind, a community of over 600 Chapters in 150 countries designed to educate, inspire, and connect entrepreneurs. Since 2012 Startup Grind has hosted 7,000 events for more than 250,000 people.

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About the talk

A panel with Jay Williams, Founder + CEO, Business Owner, Former Athlete, and Broadcaster talking about his journey and how you can Forge Your Own Entrepreneurial Path. Interviewed by Derek Andersen, Founder + CEO of Startup Grind/Bevy.


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What's up, everybody? Alright. Yeah, that's good. I like it. Good energy. That is my name. Welcome to California. Thank you. Like I'm over overly dressed for my suit tomorrow. Hey, so look. There's two people on the stage and both of us had a dream to be in the NBA someday when we were growing up in one of them stole that dream from one of the other. What's so great obstacle to have you and would love to to just start by for those that aren't familiar with your career that aren't familiar with the

things that you have a have ever accomplished in the Sports World. Tell us a little bit about how you got started. You know, how you got to the NBA and what's were having you on that? The cliff notes version is my grandmother has a disease that my mother has currently which is kind of been a struggle for me is only child called PKD polycystic kidney disease and we took my grandmother to dialysis three days a week for 9 years of my life as a little kid and in New Jersey we have this thing called the parkway, you know, the government likes to take your money as you cross two

different thresholds of the state and my mother and the passenger seat with always have me the quarter in the dime and I always shoot over my mother to make the Inn at the first time. I kind of started liking Sports in Just got involved in basketball and then got lucky enough to go to Duke University and play for Coach K. Which is a major inspiration is my life is not as a coach on the floor, but in the coaching the game of life and then I went from there graduate school in 3 years got very lucky and you don't happen to become the second pick in the draft because there was a 7-6 guy in

the draft cuz there's a lot of seven six players in NBA end, you know, I was a second picking up the first not that I'm bothered by it. But you know what happens when bother me either and then what happens to all of these, you know, a lot of expectations, I would think you're in you're in Chicago. This is like in the post Jordan era, right and and what happens Yeah, so I'm playing a year for the Bulls which was up and down. It was very challenging for me coming from duke was very family-oriented background and then obviously come into the league. It was so individualistic. Everybody

went through two different ways average age of our team was 23 years old. So, you know people were sabotaging you people were partying people having ball boys passed notes two different women during games. Nobody seemed as focused as my time was at Duke so, you know, there was this and I say it says I talk about the experience overall Derrick, you know, when kids get drafted you never hear kids say I'm so happy. I got drafted. You hear kids. Say we got drafted there is this family POV that we all made everybody with me has made it now, which is the wrong approach,

but you have a tendency to roll with the people that help you get there. And so for me and my life that led to Ego Clashing of my father and I cut my dad over some of the CEO of my company, you know was just a holding companies LLC He was the one making decisions for me, but I want to make this is my own. Let me to get a bike and I took my motorcycle which was against you know, our CBA contract down the street to go meet my agent met him for a marketing meeting at the time came out didn't have a helmet on didn't have any protective gear. Once again, I think I was justifying

cuz I want to do it when I want to do it and next thing I know where the bike was in 3rd gear. I click it down to neutral and in the middle of my serve rabbit slipped into second gear and the bottom wheel spun out and I hit a utility pole going 70 miles an hour. and yeah, that way I can tell you cuz I remember everything happened. I'm sorry for being Muhammad it but it's one of those things that my body spa on Parallel in the air in my chest landed on the grassy knoll area between the sidewalk and the curb as if I was laying on my stomach but my legs are on

top of each other on the pavement as if I was laying on my side and it felt like somebody was pouring hot steaming water all over the lower portion of my body and for somebody was very in tune with your body as being a professional athlete. I knew right then and there that I start screaming out pounding my fists against the payment that I threw it all away cuz I recognize at that moment. That's something right there and you wasn't you're not going to play bass professional basketball. I didn't know if I was or not but just the the heightened awareness that I put myself in that position

because of my own ego with something that let me to be distraught. beside myself what has you went the next few months and and and years as you know, the nurses there's this picture on the front of on the front of your book of your you know of your knee in the surgeries that you you had me. This is just tell one story long long after I'm sure to get even to this point and I just can't imagine the things that you went through to get there. But like what were the feelings that you had as time went on? I mean, how do you sort a

deal with that type of grief and get that type of it, you know yet anger anger depression and I woke up with a tube in my mouth and I had three metal pins inserted into the bone of my leg. I separate my pubic symphysis 14in. I relate to my wife about having a child cuz we went to the same experience pretty much had a total knee dislocation separate my peroneal nerve which allows you to pull your foot up and down. I still walk with a limp to stay cuz I've dropped foot I have to wear an afo but I'm a little bit stubborn. Sometimes you know why I went through Years and years of

depression I had to take oxycodone and oxycontin everyday cuz they equate nerve regeneration to childbirth. I became addicted to Oxycontin. I've had to attempt at suicide that think I weren't successful and it was it was a long couple of years for years and up the hardest part about it is that people constantly reminded me not in a malicious way. But in order to bridge a conversation reminded me of the worst day of my life and would ask me questions like, you know, why would you do that and what force myself to reflect so I think in a way the addiction to the Oxycontin numbed me from

those conversations and I will get answers but I wasn't aware of myself while I was giving those answers was more like verbatim just hate you I'm telling you an answer, but I don't mean it to get through a conversation. I think it's so much deep of of pain to deal Was I Thinkin in Silicon Valley were sort of Todd. Hey if you do fail fast and just keep moving and you see people sort of like these failures including me, you know company. I have filled out a product. I fell on her investors money that I have lost it just sort of disappears from the world. But you know with you is his you know,

you had to deal with that every single day every person that saw you I saw that I let you know I heard about you. I'm so sorry, you know and and you're just, you know, almost impossible to get out of those conversations or to get out of a different state of mind will the hard part and it's for everybody like I'm sure you guys all recognizes there was an identity crisis, you know, I went outside for Chase Bank and I literally did one of their social media heads and while I'm doing it, I had three people that came up to me and you like what do you do? If the first question I asked me not

pay. What is your name? How are you? You know, it's what do you do? So just identity crisis of always Associated who we are with what we do for me. There was this crisis that happened because What I did I can no longer do but I had categorized myself as a basketball player. Sure. I could not play basketball any longer than that sent me that kind of let me into a deep spiral every everything you retire identity everything you've worked for the previous 10 plus years everything let this one thing but now is completely gone and I see it all the time in business. That's

especially with startup. I see a lot of stars that fail and then I see people that can fall into deep psychological states of depression because they may have lost somebody else's money or they may have overextended themselves or jeopardize our relationship. And then how do you how do you pick up the pieces if that is the case? And that was the beginning process of my own experience about hey, I'm in this really bad place. I'm allowing others to dictate what my narrative was and it wasn't until no for five years after my accident that I kind of started the whole reinvention process.

And what what did you do? I mean, where did you start? To pick yourself up, I start to form individual boards and I start to recognize that in the boards of companies really help evaluate to the CEO and other Executives where that company currently is and how their hair in their target markets and where they plan for the future of the company to go. So I started thinking about who do I want to be around that can actually hold me to a higher standard. That's what I had in college be around Coach K. I didn't necessarily get the time to build equity within my relationships as a professional

athlete and I start working with different CEOs, but just not in the vertical a business in the verticals of Life fatherhood being a husband. I had to do that with my wife we talked about all the time now and just you know, you are the surroundings of the four or five people that you keep closer to you, right? So obviously if I want to surround myself with people who are smarter who think more holistic about their approach who actually have more of a humanistic side to them and how they think and Keenan awareness. Those are the kind of people I want to be around. So I formed the board and then

I I learned the trick And I seen some companies do this Derek. I feel like McDonald's is Dennis right when it's like fast food fast life fast industry and how they've been able to change that narrative now to being more healthy be more conscious of Health. I think for me instead of when people say all you would have got it was an accident. I was I know I'm the guy was alive and I started to own my narrative instead of running away from it and I start to utilize my narrative towards being powerful and allow that I had to spend time with myself thinking through why I was still here cuz I used

to be very angry and say why me forever until my dad said one day and why not you maybe your shoulders are broad enough to actually carry the burden and maybe you can turn these lessons in two principles that you can help other people. Learn how to navigate Rough Waters in very well said I think in the start of World look when we look at technology and you look at you know, you re Forbes. Are you read? Text Brian sure you read whatever you read the New York Times Wall Street Journal, you know, you see so much success and when it comes to startups in and Entrepreneurship, you see

if those are the stories that are interesting to tell if people that we have on the stage many of them have been seemingly always successful and it's it's really hard to I think it's somebody that has had a lot of failure. It's it's hard to relate to those things and I think they're looking at your sort of where you come from and then sort of the deepness of how difficult the situation was for you and to see you coming out of it. I know for me like that's actually super relatable. I like that's inspiring to me so I can actually I could be like Jay Williams, you know, I

can't I can't be like Mark Zuckerberg like I can't go to Harvard. You know, like I like I wasn't I did my first idea where is is being like Mark Zuckerberg the goal? Well, that's because I'm not saying that does that to find success for sure. I think when people know casually throughout the word success, we always equate that right to monetary value for should I, how much money do you have in the bank? I got to see you. I'm sorry for T-Mobile company and was up. There was a Fortune 500 company and the job had taken him all around the world and he didn't get a

chance to see his first kid go through high school and he came to me like, you know what? I'm going to quit my job, but you weren't here to see more of a Fortune 500 company. Why would you do that? I want to see my kid play the first couple years of high school football. He quit his job, which I thought was fascinating to pay attention to and then a Headhunter found a smaller company and then four years later after he's watch this kid play high school basketball High School football and get a scholarship to college and Equity Fund came in and they bought him out for a 10 multiple and he

made X amount of money, but that wasn't that you need anything that says he thinks it's s watching his kid play throughout high school and it's amazing how he changed it recalibrated. What is definition of success was and that got a payout on the back. That's a great inside. So what does success mean to you? Like it did that that end of the road do you say like, I was truly successful. What what would that mean meant? I'm still I'm still navigating this. I mean, I don't think everything is as black and white, I think right now, I have a 16 month year old daughter. I have a wife

and I'm learning how to balance my ambition ultimately with my family, right? Because I think now doing TV and we know working with Kevin Durant Kevin Durant rich kleiman on the boardroom making Investments, you know doing certain things are coming Partners. I can send you in a lot of different directions in life, but understanding that I can't do any of that unless the backbone of my existence it starts with that and I want to make sure that I am present and the My location to have for my daughter and my wife take priority over all these

other things so I think learning how to balance out his it's challenging as arduous, but it's a hell of an opportunity to have high like I'm here, right? So it's my job to evaluate that in to make it the best worth it can be but one thing I love about your post basketball career is I remember seeing you on like ESPNU and like these, you know at not like not like the duke-unc college game Oxford, Mississippi Oxford Ms. Cities, like, you know these colleges in the middle of nowhere that nobody goes to and I remember seeing you at those games are seeing you

talking about the things in and to see you that there's lots of people I mean he is being such a huge company and there's okay. Maybe maybe maybe the beginning of your career help to you, you know, get up get a First Energy there, but you kind of you start at the bottom basically and now we see you today and you know, you're you're Dominant on all the biggest shows talk about all the most important topics and I really feels like that. That's something that you you had to earn and I wanted you to just talk like is my perception of that right? Dude, like you were in sort of the sort of

college basketball Niche like even you know, the smaller days and then that's that's sort of evolved over time. Yeah. I did ESPNU for born at 5 years. I made $35,000 a year. How much is a josh a difference difference in coming from the NBA, you know making my salary that I made there but it was such an enlightening experience for me. I don't think I had any clue to what real work was until you start doing 16 17 18 hour days in front of the camera and I think it made me relate to towards everyday people. I think sometimes if you get a chance to be a professional

athlete you end up living in this bubble where you're extremely isolated and the connectivity level isn't as high be Your experiences are drastically different. Where's now traveling carrying? Sometimes my own camera equipment, you know staying at a residency in understanding that no, the walls are so thin I'm not sleeping cuz I have to get up if she turned in for the position. I had just lying way back in the day and I'm so appreciative. He's like no appreciate your position, but always playing your

promotion and I think that's always been my mindset to a degree like okay, I am here but how do I scale from being here? But how do I do that effectively and efficiently as I grow my own brand I grow their businesses that I'm involved in. Talk to us about how you make decisions. What is the sort of process that you go with it? That's something you can invest in with that something you're going to spend time on or just you know, that maybe even things in your day-to-day work like hot. What is your decision making process that they had goes back to the principle of the board analogy that

I gave you before and I have some people I've had to revamp my board to have a guy my boarding Barry klarberg who is incredible and made a lot of these type of decisions. So I think now having a closed set of people that you very much trust that can help you talk through the pros and cons of scenarios. And also I think the biggest thing for me is time allocation. I work for Disney ESPN is you know, I was going to Disney umbrella, but I just don't have one job at ESPN. You can see me on get up. You can see me on first take can you see me do Sports Center? You can see

me do NBA Countdown PTI PTI. You can see me do the boardroom. We like this back to ESPN. So I'm constantly going to concert around there. I was involved with an insurance company. I'm involved with symmetry which is like a CD or the service company. So it gets to a certain point where they okay scalability. How many places can Jay Williams be at once realistically and talking through? Okay. Now, how do I do that effectively and efficiently and talkin through that with my team. I think it's imperative could help me with this isn't making process. I mean when you're

starting out you have all the time in the world, right? Because you're there's nothing there like it's just you and your inbox is empty and you know, there aren't any meetings but then as those things are to fill up, you know, you you can literally spend your time on a hundred different things and you know, what how you prioritize can actually be what makes a maker brakes whether you're actually successful. I agree and you know, you are a lot of people in the business. But you know, what's be to see you know it to the consumer and the way I've tried to build my brand new. all through

connectivity so I recognize this a guy that I've known for a very long time his wife just randomly left him in this is before I even wrote a book and we were talking through it and he was in Devastation extremely depressed and I recognized that planted that's your that's your motorcycle accident so everybody has had some kind of accident in some form or fashion and the more relatable you can be about your experiences and I think the proliferation of social media has really helped that right because you have a built-in distribution model for me and not understanding that and being able to

relate experience with people and understand that this journey is forever ongoing I don't have everything figured out and when I see who I say this is how you doing Miss Dynamite actually I don't know if I believe you because there's a lot of ways you can do it at all is all depend upon Personal Taste and personal growth and how you decide to take that if you decide to take that seriously or not so I think that's the way I try to go about relating because I think we have more in When do we do? You're not in common? What are you like $0.02 and just seeing your you know, you're working

and kind of in preparation of this probably have seen it more than one of you have seen it. I like it seems like your ambition is far beyond Sports. I mean it's obviously is but I wonder like do you in terms of like how people to find you maybe maybe some point you said in the past? I'll be able to find you from the accident had a hard time believing that a lot of people do that today. But like in the future, where do you where do you aspire to be sort of like what? What what do you hope in the future? Somebody says about all their Shay Williams. He's he's this person or he's this is it.

Is there somewhere that you're like trying to go, you know, I had to I had to deal in real time with the death of somebody use kind of been a mentor to me in my life and I haven't had a lot of experiences with Kobe and what they speak. Did that I have had their have been extremely impactful and meaningful and I saw him a couple years after my accident and I can't tell you how many people are you? Okay, what's going on? How do you feel you know, and for Kobe? The first thing that came out of his mouth was we had accident where we going to do now with

the plan, right? And who's that for type thinking it was think next play and dealing with his death. I found out your 20 minutes before I had to go on national TV and figure out a way to articulate what this man is meant to me in my life in front of millions and people it once again reaffirmed the perspective that I think I once had when I almost passed away is that a lot of times I thought I wanted my legacy to be with. No. Do I want to be Michael Strahan? Do you know do I do I want to be a president of an NBA team, you know, do I want to be this adventure capitalist and make investments

to be all over in or ultimate late in the day do I? My legacy to be this person that connected to people and it didn't matter if you were successful or if you guy who was on the street, you can learn something from everybody and my wife has been imperative of my life and helping me learn. My daughter has been imperative my life help me learn even are exchanged in the back room. I learned a couple of nuggets from you already and I think it's that approach that ultimately will be a differentiator and that's what I want my legacy to be like, I want more of

this interaction and being vulnerable. I think there's something very important about expressing and being direct and trying to learn how to speak and then having a transactional relationship I get something from you to get something for me. I'm like no, I want a value exchanged. I guess what I want my dream to be so I try to holistically think who are people that want to lie myself look like that. Got that in that that's really the core of what star crane is, which is the values of giving more than you take in helping others first his ideas, like especially as entrepreneurs were like prone to

just pitch people's brains out, It's a terrible experience to get pitch tonight. I read about something that you an event recently just ways and ways of people coming up and pitch in you and trying to sort of extract and athletes with my kids at games trying to extract an autograph or some sort of guy with a like what I can do. All I can do is see you no thank them on Twitter or something and like, you know, it's hot but how do you how do you do something first? How do you give first like, how do you how do you make that first step of of trying to help first? Because it all comes back, right

it all eventually comes back I think and I'm still obviously learning but I think I'm way more conscientious of my energy level. So, you know we talked about this with Odell Beckham when you know, there is video of him inside LSU locker room, and I was a slap in the cop right on the butt and everything was just having fun. I'm like, yeah, okay, but that could be detrimental to the brand of Odell Beckham jr. And thinking through your steps before you do them instead of just reacting right. So I think for me when I step foot outside my home by holistically have to look at my

approach to say okay, how could this affect the bottom line of my business for decisions? But also like I want to be able to be present for conversations, like I think there's something to be said about being in the moment with you talkin to you actually listening to what you say and but also when I leave I am really exhausted but my wife gave me a podcast listen to she loves Tim Ferriss. I can't talk. I feel like I know every Tim Ferriss podcast that much and Esther perel and that's real Sesame. I was so fascinating because you talked about how you cheat your family from

experiences, and she said, okay. You're not for newer Samsung startup grind conference. It's amazing. Congratulations on that. So you come to work every day and you pour all your energy and effort into your job. And then when you come home and you're dead tired from talking you're dead tired from meetings and going through Excel spreadsheets. All these different things you can win. All you want to do is lay on the couch and just relax so she says no essentially what you're saying to your wife into your children is that your job is more important than your wife and your children cuz you're

not willing to give them the energy and effort that you gave your job because you're saying that's valued more. So how do you reserve that energy and then connect to them and then feel you have enough in the tank to keep going that's it. It's challenging but it's worth it. If you learn how to do it I had and I'll be vulnerable here for a minute but a few years ago and a neighbor of mine said to me I walked very fast we have my wife and we have four children and I I just I just walked very fast wherever I go and my wife's the most wonderful person in the world. She she More laid-back than I

am thankful. And I'm super high maintenance. She's super low maintenance and my neighbor said why do you always walk so far from your wife? Like why are you walking together? And he said why and I you know, I just said me and I I didn't I didn't mean anything by it be like in and we start talking about marriage and he says like hey, if you if you put as much creativity into your marriage and it's your family's you do your business then you know, just imagine like how incredible like the results are going to be and and you know, I think that's you know, that's sort of what you're saying

is like, you know giving giving them you're all the same as you would give a course. You care way more about your family than you do your business, right? So you but it's like we're sort of I don't know where like in did not to do any Jack opposite of what we know is the right thing to do and it's about all correlates back to business and I think Coach K has been genius about you. Rising the sports vehicle to become applicable to our people doing business. It's spending the time with those people even if there if your present for small fragment of time that can go such a long way,

example with an employee if you could take the time to ask your employee. How's your family doing? How are you doing to be? You know, they have an issue I wasn't thinking about what that does that relationship with that employee first off. It breaks down a series of walls because you may be an authoritative position. She may or he may not know how to communicate to you. But then they find out that you're investing in them. You're taking a fraction of your time to invest in them which inevitably and eminently makes them work harder for you because it's not about just me checking in and

checking out. I see so many people is like I go to work I do the bare minimum I leave at 5 because nobody take the time to understand how they're motivated. Now. I know you can't do this at scale. But even if you're teaching the people right beneath you how to connect to the people that they work with and that matter can change the dynamic of relationship. And that's what my wife talk to me about you. Like I want you to understand what motivates me in different spheres and understand how to communicate to me in that way. And I think that's a great lesson for a lot of people to

understand. I wanted to ask you about authenticity and I just go back to your you know, you're the comments that you made about Kobe Bryant in the midst of that tragedy I think to me and I know even you know, my my little boys like have gone and watch everything on it and and they've come back to what you said more more so than anything else that's been published. I think it goes to now having spent a little bit of time with you, you know, you're you're an extremely authentic person. I think the person that we're seeing here is that

is completely who you are and I think that's at something is it's very difficult. It's very vulnerable and it's not it's not super common. So I wonder if you could just help us. Understand or if I'm if I'm trying to be more true to who I am or to be more authentic like like what do you what do you do to what do you do to make sure you're true to yourself? Like, how do I how do I go from from being more real? I think you know when I first got her when the reasons I was able to write the book. I went to this conference out in Utah and I found myself it was this is called The Summit

it was incredible and it was everything over like five acres and none of yours. You're familiar with them, So there's all these different series of speakers and you walk around in about 20 or 30 of us and we're walking on this snow dirt Cable Road and and walking through the forest and I'm walking with all my friends and I see this lawn chair like this chair and nice slacks are in the middle of the White Stripes and a typical angry New Yorker me is like right now.

50 yards and Ashley like a desk and a chair. So don't say anything to me finally see a good soap for the middle of chair. And I finally to the tour guy get angry typical, right? It ain't like. Okay. Wait a second. I just saw a chair. I thought Destin a chair and I saw a sofa in the middle suicide. Why are those things there and the guy hit me with one? That's the one the most enlightening things ever heard. He's like first off why are you angry and second off and second off, you know instead of asking why they're there aren't you just go take time

to go sit in the chair or go sit in the table know the desk with the chair or the couch and I never I never even thought about that because I never spent any damn time with me my brain. I see it all the time with entrepreneurs like constantly your brain is spinning about how do I increase my bottom line? How do I hit my targets? How do I scale? How do I get my business that you're never present with yourself? And sometimes I know it's still a challenge for me that my wife and I talked about how do I just stopped myself for a minute? That's a moment of reflection in the in the

morning or listen. Deepak Chopra for a second and think about what it is I want what do I want? But realistically what do I want? And why do I want it and I think that changes depending upon where you are and your life. That's okay for it to change and I still think you have responsibilities, but I think you can always approach that with the new zest if you're able to constantly start reflecting upon. What is your mission and remind yourself what your mission maybe originally was compared to where your mission is now, maybe that could be I need to get back to what my original intentions are

made my original intentions weren't when I truly thought they should be at that time and I'll be bald and I'm different now, but wishing is important. Chad Williams, thank you so much for being here. I was it 30 minutes. So J&J Sinker kind of to have a table saw J spending hours upstairs sign in his book The life is not an accident and he's going to have it at your in the chasing booth in just a minute. So it's a lot of bad out there. That's good. Thank you for being here. Thank you.

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