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Being On Offense With Paul Epstein Former NFL And NBA Executive

By Anthony Taylor - January 22, 2024


In today’s uncertain times, we need to take matters into our own hands. This episode’s guest is all about doing that, winning by being on offense. Former NFL and NBA executive Paul Epstein joins us to share a playbook for winning both on and off the field. He shares his 15-year career in professional sports to becoming a sought-after consultant and author. He also shares how to seize 52 opportunities a year with "Win Monday" for personal growth and success, the “head-heart-hands” equation, and more. Tune in now and learn the true mindset for success and why it matters to align head, heart, and hands to define your own playbook for victory.

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Being On Offense With Paul Epstein Former NFL And NBA Executive

Welcome to the show. My guest is Paul Epstein. He is a former NFL and NBA Executive and a two-time bestselling author. He’s an awesome dude. Paul, what's happening? Thanks for joining us.

I’m fired up to be here.

I'm super excited. I love to see what's behind you and all of those accolades. Your LinkedIn and your sales career are all about winning. I love the idea of being on offense and making better decisions faster. In this work at certain times and the way the world is going now, you have to move and win. You have to WIN MONDAY, but why don't you tell our audience a little bit about who you are and what you do, and then we can go from there and the questions.

A lot of the world will know me for my fifteen-year NFL and NBA career. At 5’9” and about a buck 70, unless I can kick the ball, I'm sorry to disappoint, but I was not the player. However, from an entry to an executive level, it was a pretty crazy wild ride. It was three NBA teams. It was the NFL league office that broke some all-time Super Bowl revenue records, opened up Levi’s Stadium with the 49ers, and crushing billion-dollar goals and billion-dollar campaigns.

Even back in my NBA days, there were things like selling the unsellable. It was the LA Clippers on a day when Kobe and Shaq were on the other side of the hallway. Everybody, all my friends and family are like, "Why don't you just go work for the purple and gold?" When you're in sales, there's a little bit of this underdog scrap and fight. I know we have a lot of practitioners, leaders, and folks who are in the trenches tuning in. That's where I cut my teeth.


Strategy and Leadership Podcast | Paul Epstien | On Offense


It happened to be in a very sexy industry, but at the end of the day, my entry-level job was picking up a phone 200 times like many other industries that are more in the B2C space. As I graduated to more senior roles, it became more of a B2B game. Who makes the call to Levi's to become Levi's Stadium? Who's selling Silicon Valley for all the premium luxury boxes? A lot of that was more from the sales trenches, but the part of business and why I do what I do now was always the people side. It was always the organizational culture side.

That's the part that got me out of bed. The more that strategy started to become a part of the job, I kept on coming back to the coaching roles that I had. If you look at my website at PaulEpstienSpeaks.com, you'll see that I was known as the Why Coach of the San Francisco 49ers. After I had my own life-changing retreat back in 2016, I found my why and values. It was the first time that I ever got to call a time-out from climbing a ladder.

I stopped asking myself, “Why am I climbing this ladder? Is it still the right ladder? Is it leaning against the right wall?” This retreat re-shifted my entire perspective. Once I had that self-discovery moment, I was like, “This is cool. I am operating at a much clearer capacity. I am more confident than I've ever been. I've never had more conviction in my actions. I'm now making more courageous decisions and choices.” All of that was a byproduct of figuring out who I am on the inside, then I started to pay it forward and coach it out to others.


I'm now making more courageous decisions and choices, but all of that was a byproduct of figuring out who I am on the inside.


I started doing it inside the 49ers, but then I realized the greater impact was beyond the four walls. Not only of the 49ers but of the sports industry. Ever since then, I've been training, coaching, and consulting with Fortune Hundreds, high-growth founders, pro athletes, and Olympians. You name it. Now, I'm blazing a trail as a keynote speaker and a bestselling author. I'm a founder of a massive community called WIN MONDAY, which is also the name of my show. I'll pause there to catch my breath, but that is a bit about where I've been and a little bit more about who I am at my core.

That's awesome. What struck me looking at the CV and hearing what you're up to, there are so many people who have done the job that you did. You're not the first person to sell tickets and promotions. You're not the last person, but what speaks to that is what brought that success and what brought that all-time record. In sales, there's a confidence part. I'm sure we'll talk about confidence, but the mindset of it is so critical to winning, whether that's winning on the field or off the field, and the context that you set in the work that you're doing now by helping people drive forward and win.

Let's take a step back to when you did that retreat for yourself. You looked and it sounded like it suddenly shifted. You went from extremely successful to either different success or more success. It sounded like it had to resonate with your being. Can you take us back to that moment? What was the a-ha moment for you that either shifted what you did or provided a new perspective on what you're doing?

For everybody tuning in, I believe there's an inside game and an outside game. The way that society brings us up, the way that I was taught in my MBA program, and the way that I learned a lot about the entry to mid-levels of my career was it's this external game of metrics, goals, success, trophies, accolades, achievements, and working for the big blue-chip brand.

Don't get me wrong, there's nothing wrong with those things. What's wrong is if you only focus on those things and never figure out, do they matter to you or do they mean something to you? You can crush goals in ten different opportunities and maybe 1 or 2 of them are just going to have a deeper purpose. You're going to feel like you're driving a greater impact and you're contributing more. You're helping more people and you're leaving people in places better than you found them.

We could call those things fulfillment. You could call them happiness, joy, purpose, and impact. When I figured out who I am at my core, I realized that there was a little bit of a gap between my inside game and outside game. While I was winning a lot on the outside and the world was saying, “Bravo,” my LinkedIn profile looks sexier by the day, week, and month. The sports industry is so attractive that people would never question why you do it. That was part of the problem. I stopped asking myself, “Why am I doing this?” Instead of just drifting on default and, in my case, climbing, growing, and succeeding by default, what if I could live, lead, and operate by design?

It was a shift from default to design. At the retreat, I started to have not only my internal a-ha moments but I started to create processes and systems. I know we like to get tactical here on this show. For me, it wasn't just why and values because if I stopped at those things, to a lot of folks, they can feel like a very distant North Star.

North Stars are great in blue skies, but then inevitably, what happens is the storm strikes. You could call it March of 2020 and some big storm that's out of your control. It's an external market condition. It's an environmental thing but it happens and it's real. Now you need to adapt, be agile, and navigate. My thought is we all lack resilience when we lack an inner purpose in why we do what we do. Instead of having a why and values as a distant North Star, I created processes and systems to make them behavioral.

I started to connect those things to my daily decisions and daily actions. I'm more than happy to share some of those processes. For me, it started with defining each core value then I created action statements. I started to journal and take big swings off the bat to prove to myself, “Paul, if your core values are growth, belief, authenticity, authenticity, courage, and impact, don't just talk about it, be about it. You have to take swings off the bat. You have to create these habits and rituals that basically reinforce, “If this is who I am, the who I need to connect to what I stand for, and what I stand for needs to connect to how I show up.”


 You have to create these habits and rituals that basically reinforce who you are.


It was this internal compass. When I did my Why coaching work, I basically said, “Anthony, core values. Got you. That's who you are. Now, what do you stand for?" We would do some life reflection exercises then I would say, "What are we going to do on Monday morning?" That's how you show up, but you have to source how you show up from who you are. Otherwise, it feels like you're living two separate lives and that's where I found myself in the sports industry. I had a work Paul and a personal Paul. Once I made the commitment to become one Paul, that's where everything started to change.

The internal alignment of you was critical. I am very curious about the things that made a difference at the time to work Paul to be able for you to get those numbers and make that success like it didn't happen by accident. I also hear that while there were those two Pauls, so to speak. There was the foundation for your core values, for your why, and for your mission. It was there and you go through the process of formalizing it, of committing to it, and raising your own standard so that it wasn't like a task, a wish, or a thing.

You're just like, “This is the baseline. I was already performing great. Now I'm performing here, and I'm performing more holistically for other people.” That helped you zone in on what was most important to you in addition to performance in your job, but the purpose piece, people piece, and the real heart of what makes you the leader that you are. Do I more or less have that?

If I could summarize it, I didn't leave sports. I found myself, and when you find yourself, it's authenticity. I was lacking that, not because I was trying to not be authentic. I didn't have the data points of who I am. The retreat gave me the data points. These words that I said, “Let me connect these values, which were the words to my decisions and my actions,” that's when I found myself. It was this gateway of authenticity that said, “Paul, I'm going to bet on myself. I'm not going to stop crushing goals. I'm not going to stop winning trophies. I'm not going to stop achieving and being in a high-performance space.”

I want to do it on my terms because now I know who I am. I don't need to impress anybody. I don't need to be the biggest badass in sports. I need to be the biggest badass for myself. That's where that internal confidence came from. Because I started to live on my terms, I cared about it more. When you care more, you not only have more grit, capacity, and determination. You also have more resilience because, to use a sporting metaphor, life is going to knock us down. What's my motivation to get up? When I don't care about something, I'm less inclined to get up.

Sometimes I stay down or sometimes it takes me forever to get up but when I care as an entrepreneur, I get knocked down every day, week, and month. It's like the most temporary thing. I'm like, “That happened, but this is my business baby. I'm going to get up. This is my calling. This is my mission and my purpose.” I never was saying things like that before. When I got knocked down, I was like, “There's a company and they pay you. There's an industry and a LinkedIn profile.” I want to do this for my team, but my care meter. I always say, “You can't coach care.” Until you figure out who you are at your core, you're never going to max out on care.

I hear that. It's your commitment to your personal mission, using strategic planning terms, and putting your heart on there. I want to ask you about Win Monday and the book. Before I do, you put up numbers in the sporting world even prior to that. What would you say are the one or two things that you did that supported you in being able to accomplish the pure results that you did in those sales roles and executive roles?

A little bit of it starts with a saying that a lot of us have heard, but it's the application of the saying that matters more than the saying. The saying is to control the controllables. If you think about it, the market and external conditions, and I don't care whether it's a pandemic, rising interest rates, or a turbulent economy, all these external things are uncontrollable factors. The way I was raised in business, I didn't have all of those things to deal with. Do you know what I had? I had a lot of losses, meaning in fifteen years in the industry, the teams I was a part of only made it to the playoffs once.

Fourteen out of fifteen years, we had losing years. I had nothing to do with that. I'm the business guy. I wasn't the one missing shots. I wasn't the one throwing bad passes, but I had to sell that. I had to sell an experience and a team that had historically low demand. Because of all these different things and walking through different fires, I said, “We got two choices. We could either become a part of the environment, which is negative, toxic, and lacking hope and optimism.”

I could keep going, but that's what was around. That's what fans were feeling and sometimes, in the business world, you take those emotions into your own space. I was like, “No, we're not going to be about that,” because it's too easy to fall prisoner to that then you get a lot of victim mentalities. I said, “What do we control?” Here I am, leading a sales team and I'm responsible for hiring as well. What I said was, “My job is to hire the best talent.” I am after talents, gifts, and skills.

What I'm going to require of every single person that I hire in a selling capacity, I said, “I need three things from you, work ethic, positivity, and coachability, 100 % controllable. One, do you work your ass off? Two, never be negative. Always be positive. Number three is 1% better every day. If you sold ten widgets, how do we sell eleven? If you sold fifteen, how do we sell sixteen? If you sold 50.”


Strategy and Leadership Podcast | Paul Epstien | On Offense


I created a constitution. Day one, you signed the constitution. I would show it to people as I'm interviewing them and say, “If you're not in on this constitution, there's no three strikes and you're out. It's just one strike because if you don't put your hard head on, you don't work, you're not positive, and you’re not coachable, then you don't belong here.”

I was very direct with people. I lost a lot of people before they even started. Thank God, but the right people joined the team and they dialed in. What was crazy is because it was such a high-pressure, high-stress, and high-performing environment, a lot of folks who already knew how the sports industry worked said, “Paul, hold on. You're hiring me for a sales capacity and you're not putting pressure on me to hit goals. You're not putting pressure to perform.” I said, “That's my job. My job is to hire you for your gifts, skills, abilities, and talent. Your job is to work, to be positive, and to be coachable.”

I know it sounds very simple, but when you can be committed to something that you fully control, you create an organizational culture around it, everybody rallies around it, and there's no gray area around it, at that point, if you hire the right people and they have the right skill, you're going to dominate. In those environments, if you ask me, “What do we attribute our success to?” We found very few things that were non-negotiable. We never had off days with those non-negotiable things. We found the right people who believed in those things and wanted to be surrounded by those things because now it was a tribe.

Now culture became our competitive advantage and we weren't worried if the team won or lost on the field, the court, or the ice. It was like, “We have a job to do and we have careers to build. We have teammates to support and we have money to make.” That's the mentality where it was very work hard and play hard. It's because we found people that cared about the same three things.

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You didn't have to worry about them hitting their numbers because with the people that you were hiring, that intrinsic motivation was already there. They wanted to win. You just had to support them in doing that versus trying to manufacture that. I love that. As we finish up, tell me a little bit about Win Monday in one minute or less. Why Win Monday?

It's separation season in the same way that in November and December, a lot of people take their foot off the gas. I say, “You don't need to work harder in those months, just be consistent. As hard as you worked in October, worked that hard in November and December. That's two months of separation.” It’s the same thing when the world focuses on, “Thank God, it's Friday.” I say, “Attack Monday,” because nobody is attacking Monday. I built a community around like-minded and like-hearted people that we Win Monday. That's where we separate from everybody else. That’s 52 opportunities a year for us to just grow, excel, and become the best version of ourselves. That's what winning Monday is all about.

I love the idea of separation because it pushes you through instead of coasting to move forward. Ninety seconds or less, Better Decisions Faster. Why the book? What's the big takeaway?

For one, the worst decision is indecision. We've all suffered at different points in our business, career, health, relationships, and our life from paralysis. We stay on the sidelines. We succumb to stress and anxiety and we never even swing the bat. For me, I wanted to solve the problems of paralysis and indecision.


The worst decision is indecision.


It wasn't just a book about making better decisions faster and having unshakable confidence when we need it most but it was also a process that changed my life. I've been coaching it for years. Here it is in 60 seconds or less. I call it the head, heart, and hands equation. For everyone tuning in, this is how you make better decisions faster. The head is your mindset, the heart is your authenticity, and the hands are action. The equation is head plus heart equals hands.

In other words, when deciding whether to use your hands or to take action, there are two checkpoints. Head and heart. Head, do I think it’s a good idea? Heart, do I feel it's a good idea? When you're driving, you know exactly what to do at an intersection. Green is go, red is stop, and yellow is assess. That's how the equation works. When your head and heart are on board, it's a green light, 10 out of 10 times, take action.

When there's no head, no heart, red light, don't do it or stop doing it. When one of the two is on board, head or heart, then it's a yellow light. We have to solve the gap. I wrote the book to inspire a business, a career, and a life of more green lights. I wrote the book to create awareness so we stop running reds. I wrote the book because the yellow is the messy middle. Better Decisions Faster is the playbook for how to conquer and navigate the messy middle of yellow.

That's awesome. I love that. I have heard head, heart, and hands somewhere. Hopefully, I see that and it was attributed to you, but I can't remember what it was. I do like that uncomfortable middle and I love running red lights or avoiding running red lights. All of this speaks to you, so I know proper preparation prevents poor performance. One of the things that I've been reading more about as we talk about confidence is preparation.

If you are prepared, you make the right decisions. Part of what I've heard is that the preparation is, "Are my head and my heart in line? If I'm walking in there, I can have the confidence that I'm making the right decision, picking up the phone call, or saying the tough thing because I'm super committed to what it is. When we first started chatting, you were telling me about something that you have for our audience so they can assess their own confidence and see where they're at. Do you mind sharing that as we finish up?


Strategy and Leadership Podcast | Paul Epstien | On Offense


It's all at PaulEpstienSpeaks.com. Right there in the main app bar, you'll see Confidence Quiz. In less than five minutes, you'll have your very own confidence score of 1 to 100. Here's what's cool. Everything I described, the head, heart, hands, green, yellow, and red are all integrated into when we send you your confidence score, there's also going to be ways you can level up your confidence from that point going forward.

The head score, the heart score, and the hand score, which one did you rank lowest in? Great, start there. That's the greatest area for improvement, then move on to the next stage and the next stage. It's all integrated into better decisions faster. Here are the parting words that I'll leave everybody with related to the quiz. Don't think of confidence as a light switch where it's either on or off. I'm either confident or I'm not. Think of it as a dimmer switch.

A dimmer switch like maybe your initial quiz is going to give you a score of maybe 82, 91, 70, or 48. All good. That's your score today but just like a dimmer switch, plus 1, plus 2, and plus 3. It’s constant focus, repetition, discipline, and practice. Inside the report, I will email you your confidence score of 1 to 100. You'll have exactly what you can do to not only build unshakable confidence but sustain it. Just like a dimmer switch, we'll give you the score for today, then you apply what's in the report. After that, off to the races you go. It's all at PaulEspteinSpeaks.com. Hit the confidence quiz and you're five minutes away from having your very own confidence score.

Paul, I appreciate you. Thanks for being on the show. Thanks for sharing. Thanks for bringing your heart and your head to this conversation because I know you want people to win. I appreciate you sharing your expertise in doing that.

Thank you so much, Anthony. I love being here.

It's my pleasure.


Folks, my guest is Paul Epstein. Find him at PaulEpsteinSpeaks.com, author of Better Decisions Faster. A couple of things I take away from this conversation are continually trying to get a little bit better, hiring for values, and making sure that you have the right people on the right team. More than anything, make sure that there's alignment between where your head and heart are at, and make sure that your people are all in line so they can be their best.

Confidence doesn't just get created. It doesn't just disappear but check yourself for how you can elevate your own confidence, and your own team's confidence to make the best out of today, and of course, Win Monday to create that space. Thanks so much for being here, Paul. I appreciate it. Folks, thank you for tuning in. I appreciate you as an audience and as individuals. Holler at me next time you see me on YouTube. Just say, “What's up?” Be sure to reach out to Paul. Once again, this has been the Strategy and Leadership. My guest is Paul Epstein. My name is Anthony Taylor. Thanks for being here. I'll catch you next time.


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About Paul Epstien

Strategy and Leadership Podcast | Paul Epstien | On OffensePaul is a globally recognized keynote speaker, #1 bestselling author of "The Power of Playing Offense", and Chief Impact Officer for PurposePoint. He is known for transforming underperforming NBA teams into top financial performers and breaking every premium revenue metric in Super Bowl history as the NFL's sales leader.
With almost 15 years of experience as a professional sports executive and founder of the San Francisco 49ers Talent Academy, Paul has continued his leadership with Fortune 500 companies, founders, CEOs, MBAs, and professional athletes. He is passionate about helping people and organizations unleash their full potential by focusing on leadership, culture, and purpose. His new book "Better Decisions Faster", provides readers with the tools they need to make better decisions in a fast-paced business environment.



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