I recently interviewed Cvent Founder and CEO Reggie Aggarwal on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today is the founder and CEO of the largest event software company. Reggie Aggarwal is the founder and CEO of Cvent, which was acquired last year by Blackstone for $4.6 billion. Reggie, thank you for joining us.

Reggie: Thanks for having me, Adam. Excited to be here.

Adam: Excited to have you on. You grew up in the DC area, which is where you built and continue to run Cvent. You did your undergrad at UVA before pursuing a career as a lawyer. Can you take listeners back to your early days? What early experiences and lessons shaped your worldview and shaped the trajectory of your success?

Reggie: I probably would say there are a couple of things. I'll take it kind of more like high school. And the reason I'll start there is because I think there are two things that really helped change my life. The first one was when I was working during the summers, as I actually probably even started more like seventh grade. I was very entrepreneurial, running lawn care services, running snow shoveling businesses, all kinds of things that I did to really make money and recognize that there's an opportunity. And you don't realize that when you're young, these little experiences really have a major impact on you. I didn't recognize it as being entrepreneurial. I thought of that as a way for me to earn some money to go buy some stuff. 

I have three young kids, but I think the impact of being exposed to entrepreneurial endeavors early on has a disproportionate impact. You don't even realize you're building. That's number one. Number two, I was very active in my school, like I was president of my high school, but it gave me early confidence. What I realized is that when you take leadership roles or do something, it could be in sports, it could be academically, it could be in your community, your church, but taking early leadership roles again starts building things, including being outgoing. 

Some of the attributes of a leader, and not everyone's like this, but usually, when you start a company, you're either the first and hopefully the best salesperson they have in the beginning. And that means recruiting employees, recruiting investors, and recruiting your first customer. So some of these things, if you can get them in high school, sometimes it's college, obviously sometimes it's after that. But for me, those experiences of running businesses in high school and in college, instead of doing your traditional kind of stuff, as well as leadership roles through college and high school, had a disproportionate impact making me who I am today.

Adam: And you got this early entrepreneurial experience, you got this early leadership experience, but then you went into corporate America. You worked for a huge company, you got a JD, you got an LLM, and you started working at a huge law firm.

Reggie: I went to law school and this is a kind of interesting thing I was on the debate team in high school and I enjoyed it. I did pretty well. So, everyone said, you should be a lawyer. So, it's amazing how small experiences give you a different trajectory. So, in my head, I was like, I'm going to be a lawyer. So that was always kind of through what I was going to college. When I was at UVA, I was in the business school there, the undergrad business school, studying finance and management. But in the back of my head, I said, hey, I want to be a corporate lawyer, you know, use the finance and so forth. 

So, you make, sometimes major 50-year decisions on small data points. So, I ended up going to law school. I enjoyed law school, but I realized, I'm not sure when I started working at my firm, that that's what I wanted to do for the next 30, 40 years. And my next entrepreneurial endeavor is actually starting a nonprofit. And I started that about a year and a half out of law school. Like many of your listeners, I brought together a bunch of CEOs together in the Washington area. This is again back in 1996, a long time ago, but the technology community was just starting to start up here in this area. And so, I brought CEOs together. 

And candidly, after bringing them together, we kept on growing, getting more and more and more. We started off with a niche of CEOs who are Indian because I'm of Indian descent. And then once I got 100% market share, like a good entrepreneur, I said, how do I increase my TAM? So, I expanded to non-Indians and we ended up growing from about 120 members to about 2,000 to 3,000 members. And I went from organizing five, eight events a year to like 40 or 50. And by the way, that's what ended up giving me the idea of starting Cvent because I was working 60 hours a week as a corporate lawyer and working probably 30 hours a week on this nonprofit organizing events. 

And it was so painful of a process. That entrepreneurial endeavor of starting that nonprofit is actually what led to me starting Cvent because I was the customer, which was I was the event planner, and the president and the secretary of this organization. My tools were Excel, Outlook, and Yellow Sticky Notes. And I knew there had to be a better way. And that was the start of my idea of Cvent, by the way. So, one entrepreneur's idea led to another.

Adam: Reggie, you shared so much there that I would love to unpack. Something you brought up, which is really interesting. You were on your high school debate team; you were good at it. Someone said, you're so good at it, you should become a lawyer. And you listened to that person. 

And you made what could have been a completely career-altering decision. It was a somewhat career-altering decision, but you realized that that wasn't the path for you. And you were able to pivot. How can anyone make smart decisions, listen to the right voices, assemble the right data points? How do you avoid falling into the trap of hearing something sounds good, I should do it, compared to listening to the voices of wisdom that are actually right for you?

Reggie: That's a great question. And I'll tell you, and I really have strong views on this because I lived it myself. And that example was taking a small data point, not realizing that a small data point could extrapolate 50 years out. And I'll just give you another example, just so the audience understands. I can't tell you how many people, let's say, study abroad. like study Spanish, let's say, and say, I got to do a job. And usually when you study, let's say, Spanish, your goal is, part of it to broaden your mind. Let's say you're in the United States. We tend to think a lot about America, not a lot of international exposure. So, when you study abroad, you may be a minor in Spanish for example. 

And then you all of a sudden say, hey, I got to get a job that gives me something in Spanish. And all of a sudden you took it from having 10,000 opportunities to 300. And I can't tell you how many people do that. They're like, I got to use my Spanish. So, we do a lot of things in what we learn in the university or where you did your internship and just say, since I did it, the right thing to do is go in that path. And I did that in high school. So, when you think about making decisions wherever you are in your career. One is if you can have a personal board of directors, and that depends on where you are. Like if you're in college, like what I tell people before they join SEVA and out of college, go to your personal board of directors. It could be some professors. It could be certainly your parents. It could be family or friends. 

It could be someone who's two to three years out of college that you knew who was maybe a senior when you're a freshman, and you ask them about careers but have a personal board of directors because they'll be able to give you massive insight very quickly, because of their experience, especially early on in your career. As an example, it's like someone being a senior in high school and asking someone who's a fourth year in college or graduating and saying, hey, tell me what's your lens of college? And then they might say it's very important, not just the school you get into, but your major. They've walked in your shoes already. 

So, any people that can do that and have a different way of thinking, a lot of times, I'll be honest, the younger you are, it's very easy to give career advice. Like if I were to talk to young people, I could say, look, I give you all this advice. It's hard to think about it. when you're in this situation because maybe you're now 15 years out of college, you're a professional and you're thinking of making a pivot. Who do you go to on that? But the key is to make sure you have a personal board of directors and to have people who have done paths that you may want to think about so they can give you perspective on it.

Adam: I love that. I did an interview with Kunal Kapoor, CEO of Morningstar, and he shared a very similar perspective. We were talking about mentorship and he used the exact same words, find a personal board of directors. And something that I love about that concept is that it diversifies your inputs. You benefit from being able to enjoy a broad set of perspectives. One person gets to know you and says, you're incredibly talented at the debate, you should become a lawyer. You hear that. 

And you think that that's great advice, but then you have the rest of your personal board of directors to check that advice and to tell you, well, you also have these other qualities that might actually be better suited to have you go in this other direction instead. And if all you have is one voice, that one voice could be well-meaning, could be competent in lots of other ways, but could be giving you advice that's not the right advice for you. So being able to have a broad set of perspectives is invaluable.

Reggie: I'll tell you, Adam, like take, for example, someone who could be a good lawyer means they're probably hardworking, they're passionate, they're articulate, they can write pretty well, they're probably good at convincing people, which is all the attributes of being a CEO. Or maybe someone in sales, giving those same attributes with just a 2% shift can say, hey, you'd be actually good at this also. So, what people don't realize is that we might have been trained to, say, go to law school because it's a very prestigious profession. But a lot of people at that young age aren't thinking, I want to run a company or be an executive of a company. 

That's why it's great to have different perspectives because maybe those personality traits to being identified as a good lawyer when you're in high school or college, probably pretty similar to, you know, maybe you can go to business school and then all of a sudden become a business person or whatever it may be. There are some obvious ones like being a doctor or something like that are very different probably in attributes because it's a different path. But it's a little tweak of kind of when you start a journey and you just tweak it one degree 50 miles later, you just go one degree different. You are a very different point than if you hadn't moved one degree if you look up 50 miles. And so that's what a lot of people don't do.

Adam: And a through line in what you're sharing is when you're making decisions, make decisions that provide optionality. It's very easy to zero in on something and say, I'm going to do this. I'm going to go to law school or I'm going to teach Spanish in this country. But is that opening more doors or is that closing doors?

Reggie: That's what happens to most people, in my view, use these areas, because I can't tell you people say, I want to use the language degree that I got because I went there because whatever reason they made a decision in their first year in college to become a Spanish major or a minor or whatever, and then now they've used it to affect the next 50 years.

Adam: You mentioned how Cvent came together. How did you take that idea and turn it into a multi-billion-dollar business?

Reggie: Well, it wasn't overnight. You know, we call our 25-year overnight success. But look, you have to be mentally prepared. It's a little different now than when I started the business. And everyone has their own journey. For me, I started that CEO group. It was called the Indian CEO Tech Council, the one I started in 96. And then by 99, I quit my job and said, I'm going to run a business on solving that pain point. I'm going to create the aspirate. And that was Cvent, how to organize events. 

So, the good news is one, I had a clear idea that I knew worked because I was the customer, as I said. The second thing is I got a little lucky because I was surrounded by a bunch of CEOs because of the CEO group. And many of them I was their corporate lawyer, and I'm going to be very direct. I learned, especially from the ones who are Indian, that, hey, you don't have to be that special to have a business. You just have to have a good idea. Be willing to be patient, be willing to persevere, and work hard. And those are the attributes that matter the most. 

You don't have to be the smartest person in the room. You just have to have these other attributes. Because being an entrepreneur many times is a war of attrition in terms of people giving up. And so, for me, by having these other CEOs, what inspired me was I saw them and I was like, hey, this person isn't candidly that special. They're not particularly articulate. They're not particularly well off. They didn't have a network because a lot of them immigrated here from India. And what actually inspired me was like, if they can do it, I can do it. Because sometimes people put an aura around CEOs, especially this is again, back in 98, and 99. 

Now there are so many entrepreneurial startups that are started by young founders. That wasn't the case back then. But the point is, is that how do you get your inspiration? Are you committed to it? And I can tell you, the journey always takes longer. And again, just realize you always talk about the successes. The reality is for every success, the stats are probably more than 95% fail, and then the 5% would succeed. And this is what the backbone of America is, is small companies. That wasn't necessarily my interest, but small companies are still the backbone of America and the backbone of our international economy. 

But the reality is less than 1 in 100 gets to scale and go public, for example. Might be 1 in 1,000. And so, when you build your business, you have to realize you have to be patient. Most don't work out. The large part of success is just what I call hang around the hoop, stay there, hang out. Hopefully, things go your way if you just keep working hard, and be persistent. That's the biggest thing is to mentally realize it's a long journey. Make sure you're kind of in a good financial position in a sense where you can work. 

I didn't take a salary for the first three years I put everything into the company. I was fortunately not married. I was able to live with my parents. And so, I didn't have a lot of expenses and I never thought it would take this long. I mean, it really took us about a decade before we really saw real value in the company, if you believe it. Almost 10 years, maybe eight or nine years. So again, patience, commitment, and then of course the biggest thing is to surround yourself with a great team. And those are probably the attributes that kind of believe also.

Adam: One of the interesting things about your company and about your team in particular is that you've had essentially the same management team from the time you founded the company to today. How did that team come together? How have you been able to keep that team together? And what do you look for in building a team and in the people who you surround yourself with?

Reggie: One is a little luck. I got a little lucky to find some really great people. But look, how do you create that environment to get those types of people? I'll tell you two or three very clear rules. When I interview someone, first, you're trying to qualify them to make sure they're good enough. That's the first set of interviews. But the second set, which is just as important, is if you were their brother or sister, depending on their age, maybe your mother or their father, depending on the age gap. But let's just pretend I'm interviewing an executive and I would consider them someone who could be my brother or sister. The question is, would I recommend this job to them? And you have to really think that way because they'll figure it out later on. 

So, let's just say your company's a grind and you have to do this and you have to work this and this is what we expect. Be honest with them. because usually if you set expectations and you tell them transparently, then what happens is most people will process that. They'll psychologically accept that you told me this is what's going to happen. If it happens, I'm going to take it, good or bad, because you told them up front and you've been transparent. 

So, the point is to really give them a view because there are so many good people out there. But the problem is once you find a good person, is their expectation of the job do what we do? I'll tell you a simple example. At Cvent, we do something called shadowing to this day. We hire a lot of people who are a few years out of college or directly out of college. So, we make them shadow, let's say, an interview for a sales position. A lot of people have this image of what sales is. Like, no, you're going to be an SDR, a sales development rep. You're going to be on the call and you're going to be making phone calls. You're not flying around the country. You're not going places here and there, you're sitting on the phone and you're going to hear, so we make them shadow for an hour. Why? Because you're setting expectations. 

So, the first thing I would say is when you interview people, once you qualify them, make sure you truly tell them the expectations of what you think and if it was your brother or sister, what advice you would give them to take this job. If you wouldn't give it to your brother or sister for that particular person, then you may not want to give them the job because sure, they might take it, but then six or 12 months later, they're gone. That's number one. Number two is that you have to give them freedom. The kind of people we hire are very intrapreneurial people, like an entrepreneur within a company. And we give people the freedom to do stuff. 

And we're hoping that they step up, especially once you build that trust. Freedom is like half the equation to someone being happy and content at staying at a company, in my view. You obviously have freedom usually gives them impact and freedom. And then we say you're the CEO of your own book of business. So, we let our groups have a lot of freedom, which has really worked for us. And I'll tell you the third thing is not just transparency, but we try to bring in people to what's going on in my leadership. So, for example, we have our board meetings, and we've had multiple partners with NEA and Insight. We had Vista Equity Partners; we've had Blackstone right now. 

And I'll tell you what all of them say is, you guys roll big. Like when we have a board meeting, I have like 14 C ventures there. And they asked, why do you do that? I said because they want to be part of the inside. They want to know what the board's saying. They want to be at the table. And what happens when they're there and they hear it directly from the board, I like it because I don't have to transcribe, what the board said, this is how you hear it. When it comes from the board, then they hear it directly. They're able to interact and they feel like it's their company. 

So those are probably two or three things that have made us so that our tenure has been until recently, I had seven of my original 11 with us over the last couple of years, a couple of retired, but now we have, I think six of the original 11 that have been with 25 years are still with us. Those are part of the reasons. And of course, the biggest thing is now they enjoy the industry. They love the way business is going. And so, it was tough, but the beginning and finding the right people, those are some of the things that I would say to build that culture. Those are the things that we did.

Adam: Reggie, as you're describing how C-Vent has been so successful, you're really ticking off many of the keys to successful leadership. Honesty, openness, transparency, clear communication, and a focus on empowering others. You spoke extensively about giving people freedom, allowing people to be the CEOs of their own books of business. That's what great leaders do. They don't micromanage. They don't tell people, do this, do that, command, order. It's about creating an environment that allows people to be at their best and to want to show up and give their best every single day.

Reggie: That's exactly right. These attributes that I just described; allow people to do that. If you hire A players, they always want freedom. They always want to be an entrepreneur. They always want to know what's going on strategically in the bigger arena of their department or their part of their business. And so, everything you just echoed was exactly right. That's what I think has made the difference between us retaining our team. 

And it's not just the original team. I mean, we have people that have been here 15, 18 years. And I can tell you every firm that's ever looked at Sieben, I think they would put it in the top 1% in terms of retention of their leaders. And we're not talking 5 or 10. We're talking, if you look 100 deep, how many of them have been here over a decade. And so those attributes have to expand way beyond just your founding team. And to really build a scalable business, you have to build that culture deep down beyond just your top execs.

Adam: What do you believe are the key characteristics of the most successful leaders? And what can anyone do to become a better leader?

Reggie: There's a lot, whether it's CEO or it's a VP, it could even be a manager. They like people who are hardworking. They like people who are bright. They like people who genuinely care about the culture that they're creating with the team members and investing in those teammates. So those are your basics, what I call fundamentals that you have to get nailed. What takes it to another level, is giving them freedom, empowering them to be an entrepreneur. 

So, it brings out a whole bunch of muscles that people don't realize they have, you let them make some mistakes, but also give them some advice so that they continue to grow fast and make fewer mistakes. The ability to be transparent with them and to be able to set expectations, but also strategically to tell them where the company's going and where they think they can go. Those are probably all the attributes as an example that I've seen have really worked on a personal level with me. from an executive level communicating is a really big one because usually with communication comes transparency, honest answers saying where you're going, hey what's the things that are working, what's not, and people are learning as businessmen and businesswomen. I'd say that's a big one. 

And two, they need to know that you genuinely care. Like that, you genuinely care about them. People will sense that and eventually, they'll leave, especially during the tough times. Hey, if things are going great and you're making a lot of money, sure, you'll stay. But I'll tell you where culture gets tried and tested when difficult times happen. As I'll tell you with us during the pandemic, 96% of our revenue was in-person events. Let's call them scaled in-person events. That was probably the hardest hit of any area of any company. Worse than hotels and airlines. People are still flying, people are still staying in hotels on consumer trips, but they weren't having 100, 200-person events and especially non-consumer events like a wedding. 

So, my point was that during those deep and dark times, your culture is really tested. Because at that point, it really comes down to, whether are they staying. And we're a scaled SaaS company. So, in the Washington area, there are a lot of people who want our people because we have been a SaaS company since 99. So, we have a scaled SaaS company. A lot of people and other companies are doing really well, by the way. Because the tech market took off it's tough to go through difficult times. It's even tougher when everyone's doing like this and artificially, not artificially in a bad way, but they're growing way faster than you and you're going down. 

So, during that time when lots of jobs, and people could leave, what kept our team together was again, that loyalty was built because of not just the passion for the company, but the industry. It's that familial feel that they feel that you actually care and that we're going to get through this, we've been through it before in our case, and that's when the culture really matters. And it's not just who can pay me the most or I want to go to a place where I think that I really believe in the leaders and the mission.

Adam: That example you gave, is really just one of many highly intense, highly challenging moments in the history of your organization. You've been through a lot of highs, a lot of lows, extreme lows. There were points in your business where you were teetering on bankruptcy. You have had highs where you went public, you then went private, got acquired, acquired again. You mentioned the pandemic, a roller coaster to say the least. What have been the keys to leading through the highs and through the lows? And what advice do you have for any leader on how to lead in times good and in times bad?

Reggie: Let me just give you a quick timeline. So, starting the company in 99, in 2000, just four months later, we had lots of challenges. Just starting any business, you're running through tons of challenges, and it's again, where most companies aren't able to get to that next level. That was our first challenge. Once you start the company and get to that 15-20 people, you start seeing all kinds of problems. In a product company, we were SaaS. Very new. A lot of times customers are like, let me get this straight. You want us to give us all your data? I remember we were talking to KPMG. But again, we want to give you all our customer data to put in your eight-person company. This was unheard of. 

So, we had our challenges and started the company in 2000, but in 2001, during the dot com meltdown was our biggest challenge. Almost went bankrupt, like 80% of our people. Then in 08, we had a challenge because it was the next recession and public and then private, and then the pandemic hit, and then public again, and then private again, and now where we are. So, all these different things, and there's a lot of other sets of things that happen, but one of the things from a leadership role is, we probably learned most of what we learned in 2001. 

When you're in a near-death experience, you go through so many personal emotions. I know for about over a year, I couldn't sleep well. It was more like 15, 16 months. I couldn't sleep well because it was so bad because we were almost going bankrupt. And when you face something that difficult, it really does. That's why they say, it's not how high you bounce. It's how high you bounce after hitting the ground. And the reason it just makes you stronger. And it really is true. So, for us, I would 100% attribute our culture to what happened to us in 01. 

So, our culture was formed between 01 and 04. That was almost bankrupt in the difficult years when we basically didn't grow. We went from 120 employees down to 25, cut 80% of our staff. And the next three years, we didn't raise any money after that, by the way, we organically grew. So that was the difficult times. And so, if I had to say what the biggest thing for us, what we learned is when you have those experiences that are so devastating, and you're able to recover, it builds you stronger. And then all the other things that happen after that are easier to handle. 

And if you have a lot of these journeys of having difficult journeys, then it makes it easier when you come upon problems and you're hoping that you build that early on. Because it's harder to do it. Obviously, when you're a huge company, you go through this, it's harder to pivot. So that's what led us to pivot in the pandemic. People were like, they couldn't believe that Cvent only went down 12% in revenue during the pandemic when 96% of revenue was in-person events. Investors who were going public couldn't believe this. That's impossible. 

The reason we were able to do that is what we went through in 01, which is we were always looking in the rear of our mirror, we were always paranoid a little bit, which is always healthy, but we built processes and things to say that a recession is going to hit, what are we going to do? That's why we did well in 08, which is what happened in 01. And then we learned lessons in 08 to even get stronger by the time 2020 hit. even though it was a different thing, we had built a lot of processes, mental psyche, and ways to handle it. We have a war book, what happens during truly like a war. And so, we had a battle plan that we immediately hit. 

And every month you get in early makes a difference later on when you're in a bad situation. So, I'm going to say I'm going to attribute it to what happened to us in 01 is the core part of our culture. That's what I would say is for us, what God has through us. Now, what is the leadership? I think you asked what are the attributes. It's again, persistence and consistency. The number one thing an entrepreneur can do is be persistent and consistent. You got to grind it out. 

And if you hang around the hoop, while others give up, hopefully good things happen if you're in a reasonable space, because spaces go up and down. Sometimes they're good, then they seem bad, then they go up. And so sometimes they take longer. Look how long AI took. I mean, I've been in my speeches talking about AI since 2015. They're finally hitting. For mobile, we've been talking about mobile since 2003 and 2004. I remember M-Commerce took a while for mobile to hit. You just have to be patient, hang around, be persistent and consistent, and build good fundamentals. And those are the leadership things that I've learned in the last 25 years.

Adam: The best way to lead in a crisis, be prepared before the crisis hits. You mentioned your war book, a physical actual book, but you had that book in your mind from that experience back in 2001. I did an interview with General Frank McKenzie, who led the withdrawal of troops from Afghanistan, and told me the same thing. 

So much of what happens in a time of crisis are things that you can be prepared for. Same thing I heard from the current head of the CDC. And You were prepared. Having that preparation allowed you when the next crisis hit, no big deal, all right, you were ready for it.

Reggie: So, a couple of thoughts. We actually did have a playbook per se, and we were digging it up, but a lot of it was just memory because you lived it. When you live something for one or two or three years, it's who you are actually. But I'll tell you what really, it's about your culture. that playbooks in your culture. They can't just start like, I'll just give you an example, Adam. Look, we still fly economy. I fly economy. And why do I do it? I know it's inefficient, people say, but I do it because then it's easy. Then no one complains about the flying economy. 

Then you give it to directors, you give it to VPs only. It's a kind of a culture of democratic culture, but it also just shows the frugality of the company so that people don't do things in that particular category of spend, but then you do that kind of attribute. So, it's a culture. So, that's number one. But look, I'll tell you a couple of things you have to build a culture of agility. And agility because when things are hot, you take advantage and maybe you're investing. You have to be smart about it because you have to know things are going to change. Like Wall Street goes this, then this, then this. You already know what's going to happen. 

And once it's a bull market, then you already know over time it's going to become a bear market. And candidly, some investors have a lot of extreme views. They get all caught up, and then all of a sudden things go down and they pull back too quickly. And that's what most companies do, by the way. They overinvest and they underinvest. So it's always about keeping a steady pace, knowing that's going to happen. So I'll tell you three things you got to do realize that if it's really good at some point, it's going to get bad. If it's really bad, at some point it's going to get good. 

So, knowing that kind of having that continuous, don't go too extreme. That's number one. Number two, is the culture of agility. You do have to be able to change. Like right now, we're in an EBITDA culture. It was all growth, then boom, and quickly moved to EBITDA. You saw lots of people cut massively from the biggest firms in the world, Microsoft, and Google, and they started realizing that their culture may not have been where they wanted it to be. It was a different culture. 

And so, then things have gone to EBITDA, but you can't go too extreme in EBITDA because it's going to go back to maybe a semi-growth culture environment in terms of financing. So, I would say that it's a culture of agility, knowing that it's going to get better or worse at some points, so just don't go too extreme. And then I'll tell you the third thing is to make sure that the leaders all have this plan. 

And of course, it changes. We didn't have a pandemic plan, of course. It was very different than, let's say, the last real crisis was in 2008. but it was more similar to our 01 crisis. But it's this culture of knowing how to dig in, again, get back to fundamentals and be patient because the storm will pass. So, this crisis will pass, but you just have to be patient. You got to dig in, keep to your knitting, and don't get too excited either way. And that's what I would tell you. What I've seen in all these crises is if you do that, then everything tends to get back to equilibrium in most cases.

Adam: How can leaders create a culture of agility?

Reggie: Start simply, intrapreneurship. And that means empowering people to make decisions. I'll just give you a simple example, like let's take Blockbuster when it got disrupted by Netflix. If that culture was of agility, the person at the Blockbuster store saw very quickly that Mary, who's 24, stopped coming to their store where they used to see them every weekend. But then when you see the 78-year-old not coming anymore because they're doing Netflix, you're like, this is the culture of a 77-year-old changing from VHSs to that. If you listen to your organization, your front line knows more about your business than many times the executives can see stats. They can see the renewal rates, they can see how stores are doing down, they can ask questions, but the front line. So, when you have this culture of agility, it has to be combined with a culture of transparency where it has to be a flat organization. 

So, for example, the front line of a company will know more many times than the people behind, especially as you scale. Like, we're 5,000 employees. So, the business has gotten so complex, that people overestimate how much the executives know. And so, the point is a culture of agility, and you have to have a flat culture so people feel comfortable reporting good and bad news. And they have to be able to get it to a person who's very entrepreneur or smart enough to say, I'm just going to take this right up to the C-suite. I'm not going to go through the chain because this is a real issue. And then they have to know how to be able to do that and feel comfortable and create the environment to do that. So if I would say, if you have that flat transparent culture along with agility, that's a hard organization to beat.

Adam: Leaders need to empower everyone in their organization and they need to listen.

Reggie: I'll tell you our big three secrets to success. Hire the best people, build the best products, and listen to your customers. And when you hire the best people, I'll just start with that because everything starts with people. Look, out of our first thousand first hires, I probably interviewed probably 700, 800 of them. I spent a disproportionate amount of my time interviewing because you can always talk to customers and get a customer. But if you hire a good person, they'll get you 10 customers every year for the next 10 years. 

So, it makes more sense to make sure you build a great culture. Plus, if you grow your tree trunk straight, it starts with your foundation, which is your people. And within that people, you find a set of people that first have great attributes. But then within that, you have to infuse the cultural pack, which is entrepreneurship, a culture of accountability, a culture of transparency, a culture of flatness within the organization, and that empowerment with a good DNA, which is the people you hire. that again grows the right tree trunk, and then you can start doing branches off that. 

And that's how you build a strong foundation, is with that people and the culture. Then you get into the other attributes, which is building great products. And then, of course, this feedback loop of listening to your customers and listening to your people, meaning your front line. And then once you have all those things working, it's really hard to beat that culture, to beat that company. because it embodies so many attributes that keep it agile. It has the benefit of scale, but it doesn't get weighed down by a lack of agility or too much bureaucracy because it's more agile.

Adam: Reggie, what can anyone listening to this conversation do to become more successful personally and professionally?

Reggie: So, I'll start with this. I have very strong views again on this, Adam. So I'm going to get back to being an entrepreneur. That's again, probably the number one attribute of our culture. If you ask people, if you had to describe Stephen's culture, they'd say be an entrepreneur. So one is, let me explain that to someone and it doesn't matter what level you are. Let me first start. If you're not an executive, you're not a C-suite. On that level, it's simple. If you're at a good company, people can tell the difference between an entrepreneur and a worker. So, what's the difference? An entrepreneur, they don't follow rules. They follow a value system. They act like the money they spend is their money. Everything they do is like, if this is my company, how do I behave? Candidly, when you have, let's say, a five-person company and you look at the owner versus the other people, hopefully, the owner is going to have certain attributes because they own the business. It's not because they're getting a disproportionate success and they are more at stake, it's usually an attribute of who they are. 

If you're an employee and you're at a good company, it's so easy to pick out who's an entrepreneur and who's not. Who's there to be a worker and who's there to act like an entrepreneur? The way they behave is very different. So if I had to give advice I would literally act like it's your business. And if you rack that business, that means if you see something really bad, you're comfortable going up to the top and say, hey, this is what I'm seeing and I'm telling you this is what's going to happen. They're not political. Because as an entrepreneur, you just say, this is what I see. This is what I think we should do. 

And they feel empowered and the way they behave. And then over time, they build a reputation of someone who's not just passionate, but someone who hopefully has a North Star in mind, but also at the same time, tactically knows how to handle a situation. So, I would say that's number one. Number two, I'm going to tell you hard work, never underestimate hard work. I'm shocked at some of the cultures that are created, which is no, you have to work hard. Life isn't easy. You have to grind and work hard. And the third is don't job jump, don't job shift so much. 

And I'll tell you that you create real value after you've been in an organization for a couple of years because you just really learn it. If you're really making an impact, and again, it depends on your level, but to really understand the industry, to understand the company, the culture, and to build credibility, it takes time. So, you have to be patient, and not jump into so many jobs. again, hang around the hoop a little bit, things happen, your vice president leaves, and then you're been there for X amount of years. And you've worked hard, they feel you, someone who is an entrepreneur, you're in a very good chance to get that. And then you continue to move up the organization.

Adam: Reggie, thank you for all the great advice. And thank you for being a part of Thirty Minute Mentors.

Reggie: Well, I appreciate having me on the podcast. Thank you very much.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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