Ambition - and athletic greatness - run in the Bloom family's blood. But figuring out what comes next is also terrifying. Molly and her brother Jeremy Bloom, two time Olympic skier and former NFL player, discuss this process of reinvention, which can make the most grueling training regiment, the gnarliest of slopes, look like a complete cakewalk.
You may have heard of Molly's brother, Jeremy Bloom: two time Olympics skier and former NFL player. Ambition - and athletic greatness - run in the Bloom family's blood. But figuring out what comes next is also terrifying. Molly and Jeremy discuss this process of reinvention, which can make the most grueling training regiment, the gnarliest of slopes, look like a complete cakewalk. Hosted by Molly Bloom. Produced by FilmNation Entertainment in association with Gilded Audio.
Molly Bloom: So most people know my brother as this like fierce competitor, first time he, he touched the football, he ran it back 80 yards for a touchdown. And he was just this kid phenom, you know, number one in the world at 18. But I grew up with him. So I got the dirt.
I mean, I remember the days where he and my middle brother were obsessed with Superman and they made my mom safety pin Superman capes to their ski jackets and that's how they skied around. So, you know, hopefully Jeremy doesn't kill me for saying this, but, um, you gotta keep it real.
You may have heard of my brother, Jeremy Bloom. He is a two-time Olympic skier and former NFL player. After we stopped competing, we each took our own unique path.
I of course got involved in poker. And then wrote a book and somehow convinced Aaron Sorkin to adapt it into an Oscar nominated film. Jeremy started a charity and founded a tech company. And my middle
brother, Jordan became a cardiothoracic surgeon. In our own lanes we've all really pursued excellence.
People often comment on this, how there must've been something in the water or how our parents must have run a really tight ship. And they did run a tight ship. We owe them a lot, but it's not just about that. Building yourself up, creating a new life for yourself after your first life as an athlete is over, requires more than just a certain kind of upbringing.
Even the most talented, most poised, and most lauded gold medalists can fall apart when they hang up their skis or spikes or racket and face the empty road ahead. Your whole life up to that point. All of your energy. All of your focus. Everything you do has been in service of one ultimate goal, a gold medal. Figuring out what comes next is terrifying.
It's the process of rebirth, of reinvention, that can make
the most grueling training regimen, the gnarliest of slopes, look like a complete cakewalk.
I'm Molly Bloom. And this is Torched. A show about the heat of competition and what the greatest athletes would lose... to win. This season is about controversies and scandals on the biggest world stage, the Olympics. And who better to talk about the high stakes of Olympic competition and what comes next than my brother, Jeremy Bloom.
And a quick heads up-- this episode is going to sound a little different than our typical storytelling. This season we'll be featuring some raw conversations with athletes that’ll really take you inside their heads.
A couple of months ago, I sat down with Jeremy to talk about how we’ve both reinvented ourselves more than once, on a path to find meaning and success in our lives. We talked about the process of reinvention and what it takes.
Jeremy, will you introduce yourself and give a brief background on your life? Your greatest hits.
Jeremy Bloom: The thing I love
to do most, introduce myself. Sure. So, yeah, my name is Jeremy Bloom and I am commonly known as the, the football skier guy focused on two sports growing up football and skiing.
So some people either know me as the football guy or the ski guy, or now people know me as Molly Bloom's brother. So depending on which facet of life I'm speaking to the other person about, those are my three names of claims. So. Um, and now I'm a CEO of a internet startup company that I started about a decade ago and the founder of a nonprofit that I also started about a decade ago.
Molly Bloom: Awesome. Jeremy, a lot of people know you, as you just mentioned as the football skier guy. And I think there was a lot of attention and due given to your early sports career, but not as many people know what you're up to now. So what's going on in your life right now and what are you working on.
Jeremy Bloom: So you know when I
left the Pittsburgh Steelers around 2009, I started the Wish of Lifetime nonprofit in 2008 while I was still with the Steelers. And really our goal is to grant lifelong wishes to 80, 90, and a hundred year old people. We have this belief that in our society, especially inside of this country, that we don't do enough to kind of celebrate, support and assist the elderly.
And we think that these folks are really important to our life. We think their goals and dreams still really matter, and we're an organization that, that grants their lifelong wishes. And it's been an incredible journey over the past decade plus. The skiing and the new football, if I could make that analogy, would be my, the internet startup that I started about a decade ago, the name of the company is called Integrate. It’s B2B enterprise software, we sell it to marketers. And so for the past decade, I've traded my skis and the football for entrepreneurship, both in the for-profit and non-profit space. And I love it. And my body, thanks me every day that I'm no longer taking hits on a Sunday on a football field or a, on a
Saturday at a World Cup.
Molly Bloom: Jeremy's story is in kind of stark contrast to the direction that I went but I think we started out in the same places growing up in this family that really valued academic success and athletic success and I formulated the plan for my life based on those values that were imparted to us. And my plan was that I also wanted to be, uh, an Olympic skier and I wanted to go to an Ivy league law school.
I ultimately ended up walking away from skiing I was pretty disappointed, kind of felt like I had gave it my all and hadn't really gotten the results that I wanted.
And so I went to LA to take a year off in between undergrad and law school. And I think I was primed for a rebellion.
And that's why when I walked into that first poker game and I saw this incredible sort of an underground scene that was happening, but also saw how I could build a business that produced these kinds of events and
leveraged these relationships. It was very appealing to me. It was non-conventional.
And this was all happening simultaneously, as kind of, you were having these big moments in your life. It was really in stark contrast. And then I really did it. I really blew my entire life up and found myself at this place where I was 35 years old, millions of dollars in debt, a convicted felon, social pariah.
And so here's my moment to create this radical reinvention. So I wrote a book and then. I somehow convinced Aaron Sorkin to write the movie.
The movie came out and it did well. And then I was kind of faced with, okay, but what now? Where do I go from here? The first opportunity that came along was this opportunity to travel the world and to speak about reinvention, about what happens when the world brings you to your knees,
So that's kind of the, the quick, dirty version of what I've been doing since the movie came out and where my path has
led. And now I want to go back in time and bit and talk about how we grew up.
Jeremy Bloom: Yeah, for sure.
Molly Bloom: So I'm trying to remember when we realized that you weren't just a normal sort of skilled mogul skier. I mean, you were number one in the world at 18 years old, right?
Jeremy Bloom: Mm-hmm.
Molly Bloom: Yeah. Do you remember, was there a point where you realized... I can really take this all the way?
Jeremy Bloom: Yeah. I mean, I think that the interesting thing for me about the two sports that I did from the outside, looking in, I was treated much, much differently in both sports. I think from a pretty young age, people on the outside looking in would tell me, wow, you might be able to make the US ski team, you might even be able to go to the Olympics. I think I showed promise at a young age in skiing, whereas the football was kind of the opposite. It was like, you're the smallest kid on every football field you've ever played on. Why are you playing football? In fact, When I was very young, our mom set up our pediatrician to pull out the growth chart and
to specifically show me how small I was in, in relation to other people, my size and how that related to me, maybe not playing football.
Because as you know, mom never wanted me to play football. She never wanted any of, her kids playing football because it was, you know, too dangerous. So there was some cross roads in my life when I made the USC team at 15 and I was like a freshman on the football team. Again, smallest kid on the football team.
The coaches on the US ski team said, look, you're a part-time skier. You, you have to move to the mountains. You have to go to high school at one of these four schools and you have to give up football if you want to be part of the United States ski team. In fact, I had to petition for my fellow teammates to sign something saying that they didn't mind if I played football, it was kind of, it was a weird dynamic at 15.
But, uh, yeah, so I think that skiing was always the sport that maybe came a little bit easier to me. And I showed promise at a younger age, football was a harder path for me to be able to stand out and have success
in because I'm five foot nine and 175 pounds soaking wet. And most people that play football are bigger than that.
Molly Bloom: I remember when you made the NFL and I met you in Vegas. And you were there with some of your teammates and I think they were like linebackers or something and you were standing at the booth and I was like, my brother's going to die. Like he is not gonna make it.
Jeremy Bloom: [Laughs]
Molly Bloom: And my whole life also, like after having that back surgery, doctors, parents they’re like... pick a new hobby girl, mogul skiing is not for you or starting that business at 25 with all these incredibly accomplished powerful people.
And then finally, when I just taking the story around, people saying like, listen, you're not going to get a meeting with someone like Spielberg or Sorkin, it's just not going to happen.
Jeremy Bloom: Oh, I will never forget that. In fact, when you were living at mom's, you know, uh, federally indicted and they froze all your assets and you did not have a lot of leverage and you're like, I'm going to do a movie.
And anytime you say
you're going to do something, we believe it because like you've proven that, but doing a movie is really hard. And so we knew it was going to be an uphill battle, and I'll never forget when you got a movie deal from a really good studio and you turned it down. And nobody understood how somebody in their right mind could possibly turn down a pretty good deal.
Cause you're like, no, Aaron Sorkin is the person that's going to write this. I was like, wow. Talk about going to Vegas and putting your whole bank account on not just red on the roulette table, but like 26 red saying, I'm going to, I'm going to hit this. I mean, that was pretty remarkable.
Molly Bloom: What do you think it was about our childhood that sort of instilled this idea and all of us that you, you know, the world can say that it's not going to happen. The odds can be ridiculously stacked against it, but still that knowing that I can get there.
Jeremy Bloom: I don't think we're unique in the sense of like, we have an ability that other people don't have.
I just think the ability inside of us was exercised at a younger age, and I would
just kind of encourage anybody to find that inside of themselves. Cause I think we all have it. And I think it just comes back to this, this belief that really anything is possible. I mean, in Jordan's example, let's say he applied to 50 medical schools. If he would have applied to 49, he wouldn't be a doctor. And so what stops somebody at 40? I think that some people. A lot of people get just too brought down or distracted by the inevitable moments of failure. And I think in our lives, we've just accepted that those things are gonna happen. And they're more kind of an artifact of the journey and less of a personalization of who we are.
We don't become our failures. We just know that. Yep. That was a misstep. All right. What can I learn from that important artifact to kind of calibrate the compass? So I think everybody has that. It's just a matter of finding it and exercising it.
Dad instilled in us at a very young age that you just keep moving no matter what happens, life is going to knock you down. You're going to fail many times in the route to, to kind of overcoming those failures to, to reach victory. And we just, we weren't
allowed to point the finger at other people when we made a mistake.
So we couldn't, be a victim wasn't allowed in our household. We had to look inside of ourselves and say, what did I do wrong? What contributed to missing the mark? And there wasn't a lot of time for crying. We had to get over things really quickly. We had to have a short memory. And mom was the more... I really care about, are you thinking about how to make the world a little bit better are all your goals self-serving, or are some of them meant to help other people along the way.
And she did a good job reminding us how lucky we are that we weren't born into poverty because people don't have that choice. Some people are just born into poverty cause of chance and circumstance. And it's much harder for those folks in life than it is if you're in the middle class. I think both of them provided a really healthy balance that I think plays out in all of our personalities today,
Molly Bloom: As you were talking, I was thinking
about two tangible things that both of them did through our life that I think really formed us.
And I don't know if you remember this, but when mom would put us to bed at night, she would lay in bed with us and she would ask us what we did well and what we could do better. Kind of like an early introduction to moral mindfulness and to sort of train young brains to be focused on... Okay. So tomorrow's a new day.
What can I do better and how can I be better? And then I think one of dad's humongous contributions besides requiring us to take radical responsibility for our lives was his instruction on fear, but he had so much passion around this that we were not allowed to let fear sideline us. And I think dad used a variety of different settings to teach us this.
And I think it was one of the most powerful lessons, particularly for me, because I was kind of a scared little kid and to get to the other side of fear, time and time again, as a young
kid is so instructive and is so impactful in how you live your life. And by the way, so is, I'm going to require you to look at your actions and see if you are a good person today.
Jeremy Bloom: For sure. You know, we were lucky to have it, because one without the other, we, I think we would be different human beings today and I'm just grateful that we were able to have that balance.
Molly Bloom: So I've never talked to you about this before Jeremy, and this is something I'm really fascinated by because it's been a huge part of my journey.
And that is when you've reached these high places, being number one in the world at 18 years old, winning world championships, three times in a row, going into both Olympics ranked number one in the world, getting drafted fifth round by Philadelphia, all these major places of success. How did it make you feel?
Jeremy Bloom: Um, it’s a good question. I mean, so backing up a little bit, just to kind of highlight the interest that I had at a very young age of, of having
success and people knowing my name. In the third grade, I probably spent more time practicing my autograph than I did in math or science. Mom still has all the pages and I'd come home and I'd say, mom, do you like this signature better than this signature?
I can only imagine what she was thinking. Like. Gosh, what kind of kid am I raising? So I think like from a pretty young age, I mean, my influences were John Elway and Deion Sanders, these larger than life figures, who everybody knew their name, they’re signing autographs. And I thought that's what kind of success looked like, is, are you signing autographs or not? Are you, do people know who you are?
And when I started to reach a level of notoriety, when people actually did know my name or, uh, what I look like and those types of things, it became uncomfortable really fast because as you know, I'm much more of an introvert than an extrovert.
Dad describes me as a well compensated introvert because most of the things I've done in my life I've needed to be able to flex, to be an extrovert. And I started to become super kind of like insecure in the sense of these people don't know me. They're making these judgment calls on
me and I would read all the things in the newspapers.
So actually, the thing I wanted the most, I realized I didn't like, and I had to learn how to balance it all and how to not really kind of tap into the energy that's created when people do know your name or your story or your likeness. And it took me definitely a couple of years to kind of get more comfortable with living a life that's more in the spotlight than a life that was otherwise lived a bit behind closed doors.
Molly Bloom: I don't know if this is true. And it's so interesting to have this conversation with you. Um, did you go into these endeavors, these ambitions with this idea that this will make me whole, or this will make my life good or where you kind of solid before?
Jeremy Bloom: No, I've gone through a lot of, kind of, different chapters in my life.
Thinking different things would complete my life. For example, there was a time in my life when I said, and I vividly remember this. If I could just make the US ski team. My life would be
complete. I could ride off into the sunset. I would be happy forever. I would always be part of the US ski team. And then I made the US ski team and I was really pumped.
I was super pumped for like 24 hours. And then I woke up. I'm like, alright this is not enough. My life's not complete. Now I’ve got to go win a world cup. And what I've learned through chasing a lot of these different kind of, I guess you could call them mirages, right? Cause like here in the desert, you look at the, oh my God, there's water and you get there.
There's no water, is like this concept of, I describe it as like treadmill goal setting where you are running but you're not really kind of going anywhere because you're reaching these milestones and you think that they're going to get you to the ultimate destination and they're not. And so what the impact that has had on my life is I have deemphasized the end result and lionized the journey. So I care much more about the journey to get to that end result and pay attention to that experience than I do to put all the emphasis on when I
accomplish this, that the other thing. And it's just more like a, a moment of satisfaction if you meet the milestone, but knowing that there's no goal out there, there's nothing out there that will, for super competitive or hyper driven, people will quote, complete, complete their life.
It's a mirage. I don't believe it actually exists,
Molly Bloom: But you at least, you know, what it’s not.
Jeremy Bloom: Well, I don't know the key to happiness, but I certainly know the key to a pretty miserable life is trying to appease everybody, trying to have everybody like you. I think that's an impossible journey, no matter, I mean, there's people who didn't like Mother Teresa for God's sakes, no matter who you are, what you do, there's going to be people that don’t like you and that's okay. And I think it's more important to be yourself, to be authentic and the people that are drawn to you and connect to you, great, you'll create some great friends, but I think it's our reality in life that we're not going to make all of our colleagues like us, no matter how hard we try.
Molly Bloom: Yeah. I mean, I can relate to that on such a deep level. I really thought that accomplishing these goals, getting to these
places would fix me, would make me whole. For better or worse and whether it was reality or not... I just, I always felt so much less than you and Jordan. I think because your skillsets presented a lot earlier than mine.
Um, I think that I had a bit of a rougher road and I always wanted a seat at our family's table. And so I went out into the world with this rage. To find the thing that was going to give me that seat at the table. And I remember the year that I made North AMs and you and I actually got the same, were both third overall in North America and that didn't do it.
And then I went into LA and I started making like $4 million a year at 25 years old and that didn't do it.
And then when I finally realized that it was never going to be an accolade or an accomplishment was about six months before the movie came out, the movie was made, people were
raving about it. That I’d somehow convinced Aaron Sorkin, maybe the most prolific screenwriter of our time to write a movie about my life on the heels of writing one about Steve Jobs and Mark Zuckerberg.
And I still didn't feel it. And in that moment was like, the sort of the end of chapter one of my life and the beginning of chapter two, in that my ideas about peace and happiness and success I have to now own, have been wrong.
Jeremy Bloom: I think it's important for all of us to remember that just because a full trophy case or a big bank account or all those types of things, I think have actually very little impact on mental health.
In fact, one of the really meaningful journeys in my life was executive producing The Weight of Gold with Michael Phelps, which was a documentary on HBO that talked to the most successful Olympic athletes in the United States history and the one common bond that they all shared was mental health, depression, thoughts of suicide.
And it kind of goes over how normal
these things are in our society today. And so de-stigmatizing mental health. De-stigmatizing depression is not a weakness in the human body and at some elevated levels, it's a condition just like diabetes and cancer. And we need to think about it that way and under that lens and so that we can get help when we're feeling not okay.
I think is a big step to contributing to maybe not the full solution, because I don't know if there is one, but making the situation better for all humans as it relates to kind of the mental health disease space.
Molly Bloom: Yeah, absolutely. And I think we've both seen this dark side of success. I would look around the poker table at night and I would see some of the most successful, most gifted, most powerful people and they were miserable and, and they were owned by their addictions. They were owned by the hedonic treadmill of I need more and I need bigger and it was never enough. And yeah, I mean, it definitely debunked that idea that like inner peace and happiness, I really think it's an inside job.
Jeremy Bloom: I think it's all a mirage. If I could just do this, my life would be complete.
Molly Bloom: Yeah. And it's not to say that accomplishing things doesn't feel good, but it is not the secret sauce. It’s not the keystone.
Jeremy Bloom: Oh, that'll make you feel good for a period of time, for sure.
Molly Bloom: Yeah, 24 hours. 48 hours.
Jeremy Bloom: It definitely makes you feel good, but it's not sustainable.
Molly Bloom: Yeah, absolutely. So what's it like to decide to retire? To finally face that blank page? After having explicit structured goals laid out for you for years and, and having this be your entire life?
Jeremy Bloom: It's funny because athletes retire at such a young age. I mean, it's kind of a foreign concept.
Oh, you're 26 or 27. You're retiring. Right. You're not really retired. You're kind of transitioning. But my biggest fear in sports was not that I wouldn't win a gold medal or whatever in football. It was that I would always miss it. And I think most athletes who reached that level know that they're going to have to kind of redefine themselves in life because they're not going to be the whatever athlete forever.
And that's really
hard, really, really hard. I've really near and dear friends who have yet to do it. And they've been out of sports for a decade and it's really difficult. I am just really grateful and I was very lucky that I was able to transition into two things that I love. I just love them. I love them as much as I love football and skiing, and they are challenging and all those types of things.
So for me, but I was very intentional. I planted a ton of seeds outside of athletics because I knew at some point I needed some of those to grow. As if they didn't, I was just going to be a lost cause.
And so most of the business ideas or ventures or things, it didn't grow, it didn't work, but I put the effort out there.
Two of them fortunately did, and I'm grateful to be able to have the Wish of Lifetime and Integrate to be able to apply my passions to.
I really kind of traded football and skiing for two, two different adventures, both as an entrepreneur.
Molly Bloom: When we were growing up, if someone would have said, what's the last thing you could see your brother, Jeremy doing in the world... I dunno, a tech startup software company.
Jeremy Bloom: Wasn’t it obvious?
Molly Bloom: Like how did that happen? I think the story about how Wish of a Lifetime happened is super profound. And if I recall this correctly, it came from traveling to different countries. Right. And seeing the reverence that they gave to the oldest people in their society.
Jeremy Bloom: I made the United States ski team when I was 15.
So pretty young. And I started traveling the world for the first time I left the United States. And one of the first trips was to Tokyo, Japan, which is like a totally different planet. If you're 15 and never left the United States. I mean, the cultural differences are pretty deep and I'll never forget this one moment.
We were on, uh, public transportation, just a normal bus in downtown Tokyo. And it was really crowded. I mean, personal space in Asia, it doesn't necessarily have the same rules and regulations as it does here in the United States. And I watched the 80 or 90 year old woman start to slowly board that, that bus.
And I was thinking, gosh, she's frail. And like, how is this going to work? It's a really
crowded bus. And I saw everybody get out of their seats and help her onto the bus, make sure that she had a seat and the bus didn't move until she was safe and taken care of. And then they bowed to her and I was really like, I was like, wow, is this woman famous?
Should I know who this is? But it just turned out. I mean, that's just normal in other societies. I mean, you just take care of the elderly and not just in Asia, but in Scandinavian countries, Eastern European countries. And so it was always drawn to this ideal of putting the elderly first and appreciating them, supporting them, assisting them.
And we shared an incredible bond with both of our grandparents. Our grandfather was my first ski instructor because you and Jordan were better than I was. So mom and dad pawned me off with pop. You guys went skiing and he had this ingenious way to teach me how to ski. By throwing a little miniature size candy bars down the mountain. And if I was good enough to ski and find them, I could eat them. So needless to say, I loved skiing at a young age. So it was, yeah, I mean the two emphases were really the cultural differences and other cultures and societies, as it relates to
kind of treating the oldest folks in those population sets. And then my relationship with our grandparents growing up.
Molly Bloom: And I think also our dad sort of had this platform of strive for excellence, discipline, hold yourself accountable. And I think our mom really instilled this moral code into us and to look and see how we could be of service.
And, you know, I think that is you at 15, noticing this and wanting to get actionable about this is certainly a by-product of that side of parenting.
Jeremy Bloom: Yeah, for sure. Especially the mom influence. I mean, I think that more of our influences to give back and make the world a better place and to treat people with great respect came from mom.
Not that dad didn't think that that was important.
Molly Bloom: Yeah. Now talk us through the software. Tech CEO.
Jeremy Bloom: When I was playing for the Eagles, the NFL had recently launched a program where players could take MBA classes at Kellogg, Harvard, Stanford, or Wharton. And because Wharton was in my backyard in Philadelphia, I'm like, wow, this could be really interesting.
Obviously it's a great business school. I was like, I don't know what I will learn here, but it
seems like a great rock to turn over and see what's under it.
And I went to Wharton and I was just really inspired primarily by Peter Lennon, who was a professor at Wharton and a good friend and mentor to me today.
So I was drawn to him and asked him if I could kind of quasi intern in his office just to be around him and try to be a sponge and absorb whatever information I could glean from that experience. And he was very open arms and said, absolutely. So after practice in the summers, I would go in and intern at American Land Fund.
And it was really there where I started getting really excited about the internet startup space. And I kind of thought of some ideas of startups and I pitched Peter. And the thing that he did teach me that really stands out is he said, before you start a company, go join one first. His quote was, go loose somebody else's money first before you lose yours. It was just profound wisdom, especially for, for athletes after their careers, because they go into a new career and feel like they can do anything and
they just need a, will to tap into like they did in sports. But so I did that. I joined a small startup. I was running customer acquisition marketing, which I had no idea what that even meant at the time.
And, but I approached it as an athlete kind of sink or swim. And then about nine months into that role. I just had this idea that software should be automating a lot of the manual processes that we were doing. And I was super naive. I didn't know what I didn't know, which actually was a huge benefit to me and I co-founded at the time with a guy who was technical, we visioned it out together and he kind of built it.
I kind of sold it in those early days. And throughout the next decade, we grew from two guys on a whiteboard to now over 300 employees in 26 countries and pre IPO business at scale. It's doing some great things for marketers. We're not saving lives or anything, but we're really helping marketers do their job, which is fun and fulfilling.
And it's been a pretty incredible journey.
Molly Bloom: Yeah, that's so cool. And also just. Absolutely shocking.
Cause I knew you I've known you forever. So I know.
Jeremy Bloom: I don't know if that's a compliment, actually.
Molly Bloom: No it is a compliment because I know how foreign that must've been for you
Jeremy Bloom: Yeah, it was.
Molly Bloom: To walk into and how not in your wheelhouse, just looking at what you focused on. And that I think it's just a huge testament to the vision and execution that you have exemplified over and over again.
Jeremy Bloom: Well, I did intentionally set a goal when I left athletics that I, and I always said this. I, in fact, I wrote it on my quote board. I wanted to reinvent myself. It was such an intentional exercise for me because that time when I left the NFL, when I left the Olympic sports arena, the natural career progression from there is maybe do some TV, maybe go into coaching, athletic training, those types of things, but I didn't want to do that.
Molly Bloom: And I think that's what I was getting at is just how radical the reinvention was.
Jeremy Bloom: Yeah, I, that was intentional. I mean, not necessarily, I didn't know that I would go into marketing software that was not intentional, but I did want to climb a brand new mountain and I had been climbing the proverbial skiing mountain for over a decade.
I've been doing the same in football
for a couple of decades and I just wanted to be a beginner again. I wanted to go get scared to do a snowplow on the greens again, and I wanted to have that beginner's mindset.
Molly Bloom: Yeah. Jeremy's humble so he's not going to tell you all the accolades that Integrate and Wish of a Lifetime have received and just how big he scaled it.
But they're both incredibly successful. You know, I'm just, I'm so proud of you and blown away everyday by what you continue to accomplish and how big it is.
Jeremy Bloom: It's been an interesting journey in both of them. And there was times of what looked to be ultimate failure in both, and which I think is really normal.
We're just now starting to kind of come out of this COVID transition where we can grant wishes to seniors in person again safely. And so just really excited about the next chapter ahead with, with our new partners.
Molly Bloom: So Jeremy being in sports and in business and in the places you've been, you've definitely seen the dangerous side of unfettered ambition and I am a cautionary tale.
So how do you, how do you draw the line? How do you not let ambition completely hijack you and your brain and how do you stay attached to that moral code?
Jeremy Bloom: It's pretty easy because, uh, I remind myself that I have a really comfortable bed and I love sleeping in my bed. It's got everything I need in there. And like the idea of sleeping in a prison bed is not really one that is compelling to me. So it's, depending on what line you're talking about. If it's criminalized, that's, that's pretty easy for me to draw.
Like that's just not a life for me. So I know that, I think then once you kind of don't go past the criminal line, although now I'm, self-reflecting on who I'm talking to and I'm finding some irony in what I'm saying, but like once you calibrate there, that's the fine line. It becomes harder. Right? Because I, I think.
Most people who set out to do something really hard, have to blur some of those lines and have to take some big risks, some calculated risks. But for me in my own personal life, it's
been pretty easy to like, not run up against the criminal line, but I need to ask you what was going through your mind. I mean, just what were you thinking?
Molly Bloom: Yeah. You know, it's, I had found something that didn’t make me feel necessarily whole or fulfilled, but came about as close as it’d ever come. And I felt special and I felt powerful and I thought that was the only option for me and that the things that it gave me, I was willing to go into hell for.
And the other piece of that was, drugs and alcohol came into play. And when you aren't sleeping and when you are taking mind mood altering substances, it starts to really degrade at smart decision-making and a moral code. And also who I was surrounding myself with. This was totally normal. And up until this point, I had always sort of gotten off on risk and fear and
everything, and always asked myself the question: “What's the worst thing that could happen?”
And then I got beaten up by the Italian mob and arrested by 17 FBI agents. And I don't ask myself that question anymore.
Jeremy Bloom: I remember towards the end of your poker games, when I would come to the games in New York, I mean, the games in LA were fun. It was like the who's who's celebrities and it was just, it was lighthearted.
It was fun and cool. And towards the end in New York, this is just my observation. It turned dark like the people in the room, just the energy felt very dark. And then I thought about collecting as much money as you needed to collect from these really dark people. And I actually started getting really concerned for your safety.
In fact, I told mom and dad that if you went missing, I wouldn't be surprised. And that kicked them with a ton of bricks. Fortunately, it was, it was close to the end. I mean, the FBI, did you the best in my view they did the best favor they possibly could have to you. Cause I don't know if you would have gotten out on your own.
Molly Bloom: Um, I know I should send them a gift.
Jeremy Bloom: Yeah. Talk about radical reinvention. They certainly helped you get there, but it felt pretty dangerous in the
Molly Bloom: If you could reinvent yourself once again, no strings attached, what would you want to do next?
Jeremy Bloom: Oh, it's most important to me now is to be the best father I possibly can be.I have a 10 month old daughter. I have an incredible wife. We're building a wonderful family and we have a Bernadoodle dog. That is our son. We love him as much as Violet, our daughter, you know, we're building a family, we're building our tribe and I want to be really there throughout the life of my children.
Everybody tells you it goes fast and I'm really early in that journey. And of course you're pregnant. And, you know, we're just really excited about, you know, building this kind of tribe together as, as the Blooms. And I want to make sure I'm calibrating my life correctly in this next chapter so that I can be a really big and immersive part of my children's and your children's life and to be a good uncle and be a good father.
Molly Bloom: It's so freaking awesome that we're doing it at the same time.
Jeremy Bloom: I know! Really cool.
Molly Bloom: It's really cool. So like, you wouldn't want to be a rockstar or anything?
Jeremy Bloom: Can't sing, can't play an instrument. Not happening.
Molly Bloom: Me neither. Me neither, but I think this is like in the fantasy world. Yeah, no, everyone always asks me when I speak. They're like, do you miss it?
Do you miss the life? And there was something extremely compelling about it. It was like, it was an adventure. Slightly dangerous. There was a lot of adrenaline. It was exciting. It was mine. Every day was different and it took me a while, but man, I don't miss it at all.
Jeremy Bloom: You dont? Wow. That’s pretty amazing.
Molly Bloom: Jeremy, I've found this conversation so interesting. Cause we've talked about things that we've never talked about and I've really thought we'd covered everything.
It's really awesome to have you. You are obviously one of my favorite people and I continue to be more amazed by you every time I have a conversation. And I’m super happy that you came on the show.
Jeremy Bloom: You're really good for my ego. I need just hang out with you a little bit more, but no, the feeling is obviously very mutual and you know how proud I am of you and how inspired I am.
And I love you. And I enjoyed the conversation.
Molly Bloom: I've spent a lot of time thinking about reinvention. Um, and I think first and foremost, it's a choice that you have to continually make. And when you zoom out in that way, then I think you have to be prepared and make that choice that you're willing to do whatever it takes to live your truth and live your purpose.
Something that really is helpful is starting to reframe your reaction, your relationship, to discomfort. It's so easy to believe our brains when they tell us that this is hard, so this isn't the right idea. You know, this is hard, so we should just quit. Um,it feels like the truth and, and I, in my life, in my experience it just, hasn't been.
So, finding a way to sort of overcome yourself in those moments and to keep going, I think, is the cornerstone for resilience and for reinvention.
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