Deep Dive with Jeremy Bloom

Intro: Welcome to the Daily Bolster. Each day, we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with my friend Jeremy Bloom. Jeremy is the CEO of Integrate. He and I have been in a VC portfolio together, Foundry Group for many years. He is a former Olympic athlete, skier. He's a former NFL player for the Steelers and the Eagles. He started a nonprofit called Wish of a Lifetime, which is amazing, which we'll talk about in a little bit. He sold his company or majority recap to a private equity firm a couple of years ago and continues to run it and scale it today to epic proportions. Jeremy, it's good to see you.

Jeremy Bloom: Always a pleasure, Matt.

Matt Blumberg: So I love doing these Friday more in depth interviews and usually they've sort of focused on the arc of someone's career and lessons they learned around the way along the way. And frequently it starts with someone being a management consultant or it starts with them being working an accounting firm or they're an entry level this or an entry level that usually doesn't start with someone who is a one- time world champion and two- time Olympic skier. But that in fact was your first career, I guess.

Jeremy Bloom: It is a bit of a non- traditional path to be running a software business as a non- technical founder that didn't go to a graduate school and it doesn't have the pedigree of most executives in and around the space.

Matt Blumberg: You went graduate school though. That's the interesting thing.

Jeremy Bloom: Well, I went to Wharton through an NFL program, which was an incredible program. I was with the Eagles at the time and the NFL offered an MBA program to go to Kellogg, Harvard, Stanford, or Wharton, and I was, Wharton was in my backyard. So I'm really happy I went to that program because I don't think Integrate would be here and I certainly wouldn't be running Integrate if it wasn't for that program. Met a few professors including Peter Letterman, who just to this day continues to be a great advisor to me. I was really inspired at that school and at that time and really kind of helped shape my thinking around what do I want to do after sports? Because in the average lifespan of a human being, sports ends pretty early for all of us, even the professional folks. And my biggest fear in sports was not winning an Olympic gold medal or not winning football games. It was what am I going to do after these two great experiences and two different sports? And that fear really was the catalyst to saying yes to going into that program at Wharton.

Matt Blumberg: Yeah, no, it's certainly good on the NFL for making things like that available. So look, we can talk for much longer than we have today about every step along the way, but what I'd love to do for both skiing and football, for each of skiing and football, is sort of zero in on one thing. That's maybe something you took from there into the business world into your professional life. So for skiing, from the times I've heard you speak over the years, my assumption is that it's something either around failure, not that you were a failure, right? You were a tremendously accomplished skier, but something that happened in the final Olympia that you participated in and sort of not metaling. How did that contribute to the way you think about running a company or the way you can think about setting goals or recovering from setbacks?

Jeremy Bloom: Yeah, I mean, skiing taught me so much. It's an individual sport. So you don't have teammates and at the end of the day, it's you against the mountain and you're either going to be the best in the world that day or not, and you have nobody else to blame but yourself. It's not like a teammate dropped the pass in the end zone that would've won you the game and you play flawlessly. So I think skiing really, really taught me the mentality needed to be on an island by yourself and shoulder all that pressure and shoulder all those big moment experiences. I think it also taught me to really enjoy the process, to really enjoy the journey. And when I was young in my career, I would say to myself, if I could just make the United States Ski Team, my ski career would be complete, or if I could just win a national championship or if I could just win a world championship or if I could just win a World Cup or the Olympics. And going through my career, I won all of those with the exception of the Olympic gold. I mean, I won three world championships, 11 World Cup Gold medals, was the youngest year ever inducted into the United States Skiing Hall of Fame, was the youngest member to ever make the US ski team at 15. So when you look at the arc of that career, it was pretty incredible. But what I learned is it's never enough. If you're just looking for satisfaction from a medal or you're just looking for satisfaction with those one things, it's not coming. And I have tons of friends who have Olympic gold medals and they want more. So it really taught me to really appreciate and respect the daily process, the daily grind of ultimately whatever we're doing, whether it's skiing or football or being an entrepreneur.

Matt Blumberg: Yeah, look, entrepreneurs will frequently go through that same thing. It's never enough. The series A is never enough. The series B is never enough. Selling the company is... You can be on that treadmill forever. So that's a healthy way of looking at it. So let's move to football for a second. And the story that sticks with me that I've heard you talk about before is the lessons you learned about organizational design and culture from the two teams you were on and just how different they were. So maybe talk about that for a few minutes and sort of how that's influenced the way you think about building your own organization.

Jeremy Bloom: Yeah. My time in the NFL was incredibly enlightening for a lot of different reasons, but specifically for being an entrepreneur, I was drafted to the Philadelphia Eagles in the fifth round and I spent a couple seasons there. Our head coach was Andy Reid at the time, and anybody that knows the Philadelphia media market knows it is really polarizing and there's a really big magnifying glass on leadership. And so I came to the team at a time where I think Andy Reid had a tremendous amount of pressure on him to win, and people handled that type of pressure in lots of different ways. The way that the Eagles handled the pressure on management back then was they tried to get the most out of the players by managing them based off fear- based techniques. And so commonly you would hear, " If you don't do X, Y, or Z, you're out of here. We will cut you. There's a thousand other players that would love your job." And really what that led to in my estimation and experience was a locker room full of individuals full of people who were kind of looking out for themselves because they didn't want to get cut, they didn't want to be the next person. And so that fear permeated and infected what I would describe as a productive culture and created a bunch of individuals and I was able to-

Matt Blumberg: So different from skiing where it is you against the mountain.

Jeremy Bloom: Oh, it's the total opposite. And I was able to kind of balance my experience with that management leadership style and structure with my time with the Pittsburgh Steelers. And the Pittsburgh Steelers have been owned forever by the Rooney family. They're a very family- oriented family. They've been an incredible head coach. And Mike Tomlin, who to this day is one of the best, if not the best leader I've ever been around. But the culture was totally different. It was flipped on its head, it was bottoms up. It was, you be the CEO of your job, you just do your job and we'll take care of the rest. And the team got to set the goals and be part of the conversation. You very rarely heard fear- based things. Mike Tomlin was very transparent. You never guessed where you stood. He would tell you exactly where you stood on the team, what you needed to do to get better. And so that there was no, this kind of like the players versus the organization or there's no secrets. You just felt like one and that locker room could lock arms. And with Troy Polamalu and Hines Ward and Ben Roethlisberger, we had a great team. I think not as talented as the roster that I was part of in Philly. We never went past the first round of the playoffs. And in 2008 when I was part of the team Steelers won the Super Bowl. And I think my belief is they won it through culture because yes, they were talented and they had good players on the field, but that team had one heartbeat. That team had a connected culture, and it was night and day different than the locker room in Philly.

Matt Blumberg: And when you started Integrate, was that part of the founding principle?

Jeremy Bloom: Without question. I wanted to be a bottoms up organization. I wanted to hire everyone that was smarter than I was. I wanted to hire people and empower them to make great decisions. Of course, it was my job to provide the framework and the guideposts of where they can be creative, otherwise you don't have any direction. But yeah, I've always wanted to have a culture that's built around performance. I believe in the Reed Hastings kind of culture playbook at Netflix where it's like, " Hey, our job every day is add value to the business. That's why we're here. So let's work together to perform well and add value." But I've always wanted to have a high degree of creativity and individuality for the team to be able to exercise their intellect and their pattern recognition and their experience to help shape the overall strategy and execution of the company.

Matt Blumberg: Did you always want to be in business? I mean, obviously you were an athlete, you knew you were an athlete, but you also presumably knew that that was going to end at some point.

Jeremy Bloom: Yeah, I mean, I had a highly successful lawn mowing business at the age of 12 and had a lemonade stand at the age of seven, and it did okay. And so to be truthful, Matt, I always wanted to be an athlete. And I knew pretty young that... I told my parents when I was, I think 10 years old, " I want to ski in the Olympics and play in the NFL." And those were the two sports that I really cared about. And at a really young age, I've been incredibly driven. And the reason I got to where I did was not through just great genes. I was the smallest kid on every football field I ever hit. It really was through working harder than anybody else and attacking every single moment of my life and surrounding myself with people that could help me become a world champion. And so I think a lot of that was through good intention. Obviously everyone needs a little bit of luck, right? Stroke luck here and there, but I always knew I wanted to be a footballer and skier. I wasn't sure if I wanted to be an entrepreneur, but however, when I went to that Wharton program, I came out of it saying, " I a hundred percent want to be an entrepreneur." I got the bug, I got the bug at Wharton for sure.

Matt Blumberg: And I actually don't know, did you do something in business before you started Integrate or did you just go straight to founder?

Jeremy Bloom: Yeah, no, Peter Lineman, I was talking to him one day and I said, Peter, " I want to start a company." And I had this idea, I was still on the Eagles and he kind of laughed at me. He is like, " Hey man, you need focus on the playbook, focus on football." But he gave me a piece of wisdom that was just really powerful that will stick with me forever. He said, " Before you go start a company straight off the football field, go lose somebody else's money first. Go join a company and learn the ropes of business. You don't know anything about business right now and you shouldn't because you don't have experience." So he is like, " Don't go lose your money opening a nightclub or a restaurant." Which 90% of the league does. He said, " Go work for someone." And I did that. So I joined a very small startup in healthcare space and they hired me to run customer acquisition marketing of all things. I had no idea what I was doing, none. But I had a fresh set of eyeballs and a lot of confidence in my ability to learn how to swim in a new deep end, so to say. And I was there I think for nine or 10 months. And that really shaped what Integrate was because the problem that we solve in Integrate was a problem that we had as marketers for that startup and that really led to the founding of it.

Matt Blumberg: So let's talk about Integrate for a little bit. You've started the company 13 years ago, 14 years ago?

Jeremy Bloom: 13 years.

Matt Blumberg: 13 years ago. And I know along the way, definitely some twists and some turns

Jeremy Bloom: Like all of them, right? Matt? I mean all of them.

Matt Blumberg: All of them. Talk a little bit about the journey. I mean, I always said with Return Path, I had the same business card for 20 years, but I didn't have the same job for 20 years. If you sort of break down Integrate into its chapters, including its current chapter with a new owner, how do you think about the journey and how you evolved as a leader over those years?

Jeremy Bloom: I think of it in three main chapters. The first chapter was a media business. We were building just a media business for B2B demand gen. We had to reinvent ourselves in 2014 and become a software business because that media business just wasn't sustainable. And at the time we just met, we didn't have any cash to do it. I think we had$ 2 million in the bank. And all of our venture folks around the table said, " We have no more cash for you." So in 2014, we had to let go I think 60% of the team. We retained 40%, we thought more would leave. Nobody left. And we said, " Here's the plan and here's how we're going to go build a software business with our customers that are buying media." And we threaded the needle. And it was fun, it was exciting. The pressure was really, really high. You wondered if you were going to make payroll just at about every single week, but you won just enough of new business to fund that. And that happened for two or three years. And over I think a two and a half year period, we went from$ 0 of ARR to 11 or 12 million and we only burned at$1. 5 million of cash. And at that point we got more interest in raising capital. So that was kind of chapter two. We called it and coined it, Building the Bridge to SaaS Island, this beautiful island with trees and palm trees, software businesses are much more predictable to run than media businesses. And then chapter three was when we were acquired by Audax. And I had never worked for private equity previously. I've heard all the horror stories and I'm sure a lot of them are true, but Audax is an incredible firm and they think much more like growth investors. They don't have their own playbook, they don't have their own bench talent. So they don't come in and say, go hire these people. They don't say, go do these things. They're just really good at asking great questions. So I feel like I'm getting smarter every day around our board members and my partners there, and we have a lot of M& A capital right now to go buy businesses and put them together with what we're doing. So I'm really enjoying it 13 years, and I didn't think that I would be here 13 years later, but I'm delighted to be here. I love to learn. I'm very intellectually curious in this kind of third chapter. I think I'm learning more than probably I ever have before and just enjoying it.

Matt Blumberg: That's awesome. I mean, look, that's how you want it to be when you sell the company, but you're still running it. You've swapped out one set of owners for another. But you're right, I don't think it always works like that. So they don't have a playbook, so they're not sitting there telling you what to do in micromanaging you. Has the change in owner, change in board, and maybe learnings you've had from working with a new set of investors change the way you lead or change the way you operate at all or change the culture of the organization?

Jeremy Bloom: I don't think it changes the way that I lead. I don't think it's changed our culture. And in fact, I can measure that against several years back, our employment engagement surveys, that the culture really hasn't changed that much. But what has changed is we're just a more mature organization. We've reached a level of scale where you can really have guiding principles help you make a lot of the decisions. I mean the rule of 40 or CAT to LTV, I mean when you're an early stage business, you have to invest so forward to growth to get product market fit that you can't always look at these guideposts and say that they even matter because a lot of times they don't when you're really early venture backed. But now we're a mature business. In fact, we have two product lines that can live on their own now. These could be two different companies. We still have a marketplace media business that's doing incredibly well and is a business of its own. And we have a software business. And so what we're doing now is we're building two different business units. We used to be one company, one team, but people would wear two hats, go to market media, go to market. Now we're creating the discipline and surgically creating two business units with specialists in each area. And it's challenging. It really is challenging and it's nerve wracking, right? Because change can be difficult, especially as you have a 400 plus person team. And so what does all this mean for everybody? But the clarity of mission in front of us has never been more clear. So that feels really good. It always felt a little bit like scrambled eggs of running a business that really should be two different businesses. So we're getting that discipline and a has been really helpful to think through what's the right structure to make sure we're surrounding our customers in the best way.

Matt Blumberg: Yeah, that's great. I mean, look, the number of companies that have multiple product lines that go in and out over the years of now we're functionally organized and now we're bus and back and forth has left me convinced that there's not a right answer, but that there's probably a right answer for any given company at any given time. And that's interesting to hear that that separation is going well. It certainly gives a lot more focus. There's no question about that.

Jeremy Bloom: Yeah, I mean it's difficult when you have one go- to market motion, but a different buyer and a different pricing and different packaging and different positioning. And what happens in our case is you get this conflict of brand. Who are you? Who is Integrate? Are you this demand generation platform that can fill my pipeline with sales opportunities that's globally compliant, which is our media business? Or are you software to help me manage the efficiency of all of my demand marketing in a more thoughtful way? And that conflict has held us back, especially from a brand perspective and just from a confusion perspective of our customers. So for us, this was the right answer. The only reason we didn't do this sooner is because both business units weren't big enough to live on their own. It was always a very profitable media business and a software business that was burning too much. And so we've been able to take the proceeds of the media business and really use those to invest in R& D. And now both of those are big enough and have a unit economic profile that can live on their own. And so it's what we're doing. That's what we're up to now.

Matt Blumberg: Yeah. Well that's exciting. So five years from now, are you still running Integrate?

Jeremy Bloom: I don't think so, Matt. The average whole period with Audax is five to seven years. We will be two years in December. And I think there's just a number of both strategics and sponsors who are really interested in what we're doing. So I think look heads down right now, we want to drive customer value. We want to make it a great outcome for the folks at Audax, for our team, for our employees and our executive leadership team. But 13 years is a long time. You made it.... Did you say 20 at Return Path?

Matt Blumberg: 20. Yeah.

Jeremy Bloom: 20. That's incredible. Yeah, like I said, I didn't think I would be here at 13, but I am. But I don't think I'll be here in five years. I think I'll be doing something else.

Matt Blumberg: You got a few more in you there.

Jeremy Bloom: I'd never say never, right, Matt, because I didn't think 13 I would be here. So we'll see. We'll see.

Matt Blumberg: All right. I got two more quick topics for you. Let's talk about Wish of a Lifetime. So you started a nonprofit. You started it before you started to Integrate.

Jeremy Bloom: I did.

Matt Blumberg: It's an amazing story, which I'll let you tell, but the question I'd love for you to sort of wind your way to with it is I think lots of business people and CEOs in particular are interested in doing philanthropic things. Many have started a nonprofit, we started one out of Return Path as well. I would love to hear a lesson or two from that chapter of your life, either what worked, what you wish you had done differently, anything like that. But start with-

Jeremy Bloom: Well, I think the most common question I get with Wish of a Lifetime is why did a 26- year- old start a nonprofit for 90 year olds? And I had incredible grandparents. I really did. I was really lucky. My grandmother lived with us in our household for the first 19 years of my life. And my dad's dad, my grandfather was one of my biggest heroes. In fact, he taught me to ski at the age of three and four by throwing miniature sized candy bars down the slopes of Keystone, Colorado. And I always felt like in our country, we need to do a better job of respecting our elders. And you see that a lot in the Japanese culture. You see it a lot in Scandinavia. It's just fundamentally different how people treat and respect and revere the eldest folks in their population. So what we do is we grant lifelong wishes to primarily 80, 90 and a hundred- year- old people. And I've learned a tremendous amount being around folks who are in the last chapter of life and have experienced a lot of the problems that are unique to you and me and have figured them out. And so there's a lot of untapped wisdom. I always ask them, " What's the key to life? What's the key to longevity?" I get a very, very frequent and common answer, " Never stop moving. Even when your knees hurts or your ankle hurts, you go take that walk, go read that book, go learn that skill." I think there's probably a gravitational pull at some age to kind of tune out or switch off in life and stop doing those things. The healthiest centenarians that I've been around, and we've been around a lot of them, take that walk, read that book, do that thing, engage in life, figure out a way to stay engaged in life. So that's been a very powerful learning for me and a lesson for me. But we love our jobs. We really do. We get to knock on the door of a 90- year- old woman and say, " That wish that you've always had. Well, we're here to make it come true. So let's roll. Let's go get it done." And what plays out next is nothing short of magical. Being on the grounds of granting a wish like that is nothing like I have ever experienced. Not any winning a ski event or a football... Just can't compare. It really can't. It's just infectious of how happy those folks are. So it's been a tremendous journey. It's wishofalifetime. org. You can see all kinds of great wishes on there. We have great videos and it's been a wonderful journey.

Matt Blumberg: My bet, to tie this back to the prior question, having heard you talk about this a number of times over the years, is that the thing you do next whenever the Integrate chapter is over, is going to have more to do with Wish of a Lifetime than with customer acquisition? That's just a guess.

Jeremy Bloom: I think I would bet on that. I would bet. That's a bet I would take.

Matt Blumberg: All right, let me close with one last question. I know you've got to go in a minute. You just published a book, which I believe is your second book called Recalibrate. Tell us about it.

Jeremy Bloom: Yeah. Here's the book, this squiggly line. You can Google it and you just Google what success looks like. In fact, I put it on the first page, it's one of my favorite images in life because I think it's so true to no matter what we're doing, what people think success looks like, but what it actually looks like.

Matt Blumberg: So for those of you just listening on Spotify or Apple, what people think success looks like is a straight line- up into the right. And what success really looks like is a squiggly line that goes all over the place and ends up in a better place.

Jeremy Bloom: And I just think it's so true, and there's this falsity in life, especially around social media, where we only capture the highlight reel and it's easy to look around us and say, " Gosh, everyone else's life is so much better or so much easier." And it's just not true. We're just not posting the squiggly lines. And so I think it's a really powerful concept of being able to learn how to recalibrate in life. And no matter who you are, no matter how much success that you've had, we're always going to have moments where we need to recalibrate. And our ability to learn how to do that, especially in those moments, I think will predicate where we ultimately end up and if we accomplish the goals that we've set out. So this was actually a rewrite of Fuel by Failure, which was my first book and I got the publishing rights back and that's a book I worked with a ghost writer and I just didn't feel captured the true essence of what I was trying to capture. And so it turned into a new book because it's a full rewrite. But I'm really passionate about the topic and I love learning about how others think about this in their lives because I really do think it is the key to success and key to happiness and key to a lot of things that we want in our lives. And we probably don't talk about enough. We certainly don't learn it in school. There's no class on how to recalibrate. So it was delighted to write the book. It's available on Amazon.

Matt Blumberg: Well, Jeremy Bloom, thank you for being here today. You do have an extraordinary story to tell. It was great to have you here for a few minutes to tell some pieces of it, but I am looking forward to reading Recalibrate, and even though I've heard you speak a bunch of times, we talked now, I'm sure I'm going to learn a whole bunch of things from reading it. So thank you for being here today and for joining Daily Bolster.

Jeremy Bloom: My pleasure. Always good to see you, Matt. Thanks.