The Transcript

Benji Rogers on Getting Comfortable with Being Uncomfortable

Jonny Nastor: Hack the Entrepreneur is part of Rainmaker.FM, the digital business podcast network. Find more great shows and education at Rainmaker.FM.

Voiceover: Welcome to Hack the Entrepreneur, the show which reveals the fears, habits, and inner battles behind big-name entrepreneurs and those on their way to joining them. Now here is your host, Jon Nastor.

Jonny Nastor: Hey, hey. Welcome back to another episode of Hack the Entrepreneur. It’s so cool of you to decide to join me again today. I’m your host, Jon Nastor, but you can call me Jonny.

My guest today is the president and founder of PledgeMusic, a direct-to-fan company that offers musicians a unique way to engage with their fans during the music-making process. He’s an independent musician who received the A&R Worldwide Digital Executive of the Year award in 2014 and appeared in the 2013 Billboard 40 Under 40 Power Players list. My guest’s recent engagements include keynote addresses and panels at events, such as Canadian Music Week and Grammy Camp. He also gained a position on the board of the directors for the Future of Music Coalition this year.

Now, let’s hack Benji Rogers.

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Welcome back to another episode of Hack the Entrepreneur. I have a really, really special guest today. Benji, welcome to the show.

Benji Rogers: Thank you very much. Thanks for having me.

Jonny Nastor: It’s absolutely my pleasure. I think this is going to be fun.

Benji Rogers: Absolutely.

Jonny Nastor: All right, Benji, let’s jump straight into this. As an entrepreneur, can you tell me, what is the one thing that you do that you feel has been the biggest contributor to your successes so far?

How Benji Has Stayed Incredibly Restless

Benji Rogers: It’s funny. The question is a great question, and I’m glad you asked it. I wrote a blog many, many years ago about this. I found that I stay incredibly restless, and I’m never really content with going, “There it is. It’s done.” There’s always another way to look it and another way to hack. Quite often, you can get in a lane with what you’re doing, whether you start a business, it does well, and you carry on just doing that and you don’t look around those corners.

It s a restlessness to where you wake up at night stressing on the problem, going, “Wait a second.” It’s not a worry. It s more a restless energy. I know a lot of people that have founded companies and whatnot have a lot of energy about it, but that restlessness, I find, is something that has really seen us through the more interesting times and helped me personally look around a whole bunch of corners. It was never just, That’s how it is, so there it goes.

When I was starting the business, I was tapped on the shoulder a thousand times and told, “Listen, this isn’t how it works. You should just … ” It was always, you keep jabbing and poking and hacking and trying to find a different way.

When we founded the business in the beginning, I was told by all the payment processors, “You can’t. It won’t work. You can’t do it. It doesn’t work that way. That’s not how the Internet works. That’s not how payments work.” I was like, “Okay.” For months, it was this restless, endless push toward getting it done.

I think that similarly, the destruction we’ve seen in music space has been one in which people have gone, But I sell albums. Oops, what happened to those? We sell compact discs. Oops, there they go. Ironically, we don’t make vinyl anymore. Well, now there’s a six-month waiting list for vinyl.

When we get comfortable with things is when they start to push us off balance, and I think that ultimately, if you can find a balance in your restlessness, a balance in knowing that it’s never going to fall one way or the other. It’s rolling with the punches, but it’s almost that restlessness to dig and scratch and find another way, particularly when someone says, “You don’t understand. This is how it is.” I think that that’s when you should start to ask the most questions and let that restlessness guide you through. That was the one thing that I thought of when that question came up.

Jonny Nastor: That’s awesome, and I think that that’s probably something that’s very, very much needed, not just for you, but for people going out and starting something from nothing. You’re going to have people telling you that it doesn’t work, like payment processors: No you can’t do that. You can’t do that. It’s almost a certain level of restlessness, but also stubbornness in a way. Having people tell you it can’t be done, but being like, “No, it’s going to be … I’m going to find a way to do it.”

Learning to Become Comfortable with Being Uncomfortable

Benji Rogers: Yeah, and when I first had the idea for Pledge, I thought, “I’ll just explain ideas. Someone else will make it, and I don’t have to worry about it. And I never thought I would be the unsure person in the scenario.

A lot of it is getting comfortable with being uncomfortable. The second I would be like, “Okay great. We’ve got breathing room,” that’s when ideas would start to come, and that’s when you’re always holding back because you’re got 40 ideas for every one that you’re actually going to be able to pull off at that time. What I love is that I’ll be told — I was told today at least three times — “We can’t do it. That’s not possible. This is not here.” I’m trying to find a way through, because I just don’t accept it most of the time.

There’s a moment when you say, “Okay, done. No more pushing. That clearly won’t work.” It’s not about that or about being pig-headed about it, but I think it does require a stubbornness. But there’s a moment where you go with the flow, and there’s a moment where you have to stick your back up and say, “No, no, no. Hold on a second.”

I remember being on the phone with credit card processors back in the day, and they would be like, “Yeah, you literally cannot take money in the way that you operate.” I said, “Okay, so when you book a hotel room, you don’t pay for it right then and there. You pay for it when you leave. Yes. Okay, why can’t we do that?” Well, it doesn’t work that way, sir. Okay, well how does it work, because I’ve seen it work? It’s working there, and it says Visa or Mastercard on it.

One of the things about starting a business or startup or being entrepreneurial is that you’re battling into a space. You’re going, “Something isn’t working, and I’m going to disrupt that,” or “I’m going to disintermediate these two players.” When you’re doing that, you’re going into an inherently unstable environment. You just need to know that.

What I’ve found is that you’ll have one big win and say, “Right. There it is. I can stop now.” That’s just never the case. There’s always another mountain to climb, but I know that certain people get into a lane and find it very hard to shift out of it. I think you’ve got to be willing to throw away a couple of great ideas to come to the better one and also be okay to be wrong and say, “Right. Got it. Moved on.”

There’s actually a clothing shop in New York, Grahame Fowler, and when you buy something from him, he gives you this letter, and it basically says, “Stay restless. Stay lucky.” I really that like that expression, and he makes good shirts, too. I’m talking about him with you.

Jonny Nastor: That’s awesome. Yeah, totally. Stay restless. Stay lucky. Luck really is about staying restless. Luck doesn’t come find you unless you’re out there putting yourself out, right?

Benji Rogers: Absolutely.

Jonny Nastor: Your idea of how you have to get comfortable with being uncomfortable. Have you always been comfortable in uncomfortable situations? Is this innate within Benji, or is this something you’ve had to push and grow within yourself?

Benji Rogers: Yeah. I read a lot of Marcus Aurelius for that part. I think about planets orbiting and things that are much, much bigger than me, and my individual calm or panic is not there. My wife always says to me, “You don’t seem like you’re freaking out.” I’m like, “But I am.” She’s like, “You’re sure?” I’m like, “Yeah, I’m pretty sure this is me freaking out.”

You get comfortable with it, but it never goes away. I was describing it once that when I used to go onstage as a performer, I would have a sick feeling in the pit of my stomach. Before I got used to it, that was nerves, and then it becomes part of your practice, and then it becomes, if that’s not there, something’s wrong.

Pledge was my first business, and I’m still learning to this day. I’ve got amazing mentors and people that I trust and respect and know really well in the business who will give me a straight-talking answer, but it is inherently unstable, and you’ve got to get used to that. I’ve been in scenarios whereby I’ll have gotten off a plane, and I’ll go to walk up and be on a panel, and the host of the panel will say, “Rather than do a panel, I thought you could just do a 20-minute speech on European economic policy and how it affects art and culture.” You’re like, “Okay.”

I remember writing down four things: a) don’t eff this up, b) You sit there and go through, Okay, what are the three things I can go and talk about? European economic culture. What is it? You’re always going to be thrown into these situations, and you should see them as an exciting thing and not as a miserable thing. I think also you have to surrender the outcome. I believe that you’re responsible for the effort at all times, but the outcome is going to, in a lot of cases, remain out of your hands.

My wife, again, was saying to me the other day, she’s like, “How are you handling this kind of period of uncertainty and strangeness?” I said to her, “Well, if I freak, I’m not going to make a clearer or better decision than I am if I can remain calm.”

A lot of it is, I meditate as well, so you learn to let things roll off. What it really comes down to is that I owe my team, the amazing people that make the engine of this company run, everything. They deserve a calm and collected me, because I’m going to bake a better decision. When heads get hot and people get stressed out and burned out, you’re not seeing clearly. You’re in the moment, and if you can zoom outward and say, “Okay, in the constellation of possibilities, this is the one I’ve got to make a decision on right now.”

You get used to it, but you should never get used to it. You know what I mean? Knowing I will have to make decisions that are uncomfortable or difficult every day is okay, but I think also, I would be lying if I said I wasn’t a really sensitive person. I am, and it really does affect me, but in the moment where you’re making a decision or you haven’t arrived with something very quickly, bringing in nervous, frenetic, panicked energy does not help and will not inform the decision any better, I don’t think, and I haven t found.

Jonny Nastor: That’s impressive. It is, man. You sound like someone who obviously meditates and reads Marcus Aurelius and takes these grander things, and it puts perspective on what’s going on.

Although, I think when we do freak out, we know overall that we shouldn’t be freaking out and that it’s not going to help our team. It’s not going to help me make an informed decision, but still, to have that control within to be able to that is impressive. Really impressive.

Being an Entrepreneur Is about Entering a Space of Uncertainty

Benji Rogers: I’ve got to tell you, look, it’s imperfect, and sometimes it doesn’t work out, but again, knowing that it’s not always going to work that way calms you down. It’s part of the job description. A thousand things can and will go wrong all the time, and you know that going into it.

There are no certainties, but what I do know is this. Marcus Aurelius is someone I’ve been reading for a long time. This was an emperor who had to deal with massive responsibilities. Someone like Abraham Lincoln, who is a great hero, who surrounded himself by warring factions who dealt with the splitting of a country in two and the abolition of slavery, and all these amazing things, had to make decisions.

I think of those people in power and what they weigh, and I go, “Mine is not trivial, because it’s important to the people that we work with. It’s everything,” but I come back to that. I’m in control of how I react to this. I’m not in control of what’s out there. I’m responsible for the effort. The outcome is another matter. If you go into it with what’s going to get us through this the quickest, the fastest, best way possible, it’s never, I’ve found personally, by freaking out.

If you’re the one person who’s calm in the room, you can often promote calm. I guarantee you this. If you’re the one freaking out, you’re going to create more of that, because it’s addictive. It’s an addictive thing. My wife’s a full-time mom, which is probably 10 times harder job than anyone who’s ever started a business has ever done, and her vexations and what she will stress about are our child’s future. That’s a major one. That’s a life. Both of us, we have our freakout moments, for sure.

But as I’ve gotten older, I’ve just realized that I’m a better team member if I’m the one who’s saying, What will get us to the best decision here? People need to blow off steam and do their thing, and part of it is just going inwards and finding that. I think it’s a great asset and a strength if you can find it in yourself.

The other thing is that it’s not written anywhere in stone or in your biology that you have to freak out when stressful things come. There’s no written-down requirement that this is what this person has to do. It’s not genetically programmed to panic. It’s a choice, and the first...