The Exchanges

Q So obviously you're not a professional football player today. You're a serial entrepreneur, um, and so many other things other than just a business builder, but did you anticipate trying to play in the league? Was that your goal?

A I did like, like millions of other, uh, American high schoolers out there. Um, I got to play sports and I was really good at sports and I had the opportunity to go play in college. And my dream was to become a professional football player. I grew up and I was obsessed with two things, computers and football. And, uh, turned out that football was going to be a great path for my life. So I spent my entire college career really focused on football. There were no internships. There was no entrepreneurship. And my senior year of college, I ended up with two fully reconstructed shoulders. And after coming back off those injuries, that was really the first time I realized, like, there was no chance I was going to go to the NFL. And for all the people that have played college sports that have gotten injured like that, like they know what that feels like coming off of that.

AI assessment note: “I did like, like millions of other, uh, American high schoolers out there.”

Q team? Like how was the, How was the company set up, said differently? Like, did people look to Alan as kind of like the guiding light of this business, and you were just the operator of the business? Or did they really, did they have trust and belief in whatever you thought? Because like, to me, that means very different things in how you engage the team after this tragedy.

A Alan was the figurehead of the company. People did not have trust and belief in the new boy King CEO. Like that was not at the top of their list. And when Alan died, There was no other option. So I had to come in and be a strong leader and say, here is what we are doing. This is not a democracy. I am not asking for a vote. I am not looking for consensus. I am making decisions on the business and we're going to focus and we're going to execute. And if you have a problem with that, we're going to help you transition and find a new role at a new company. And so I had to switch instantly from like, we're having fun. We're in Jamaica. My guy got kidnapped. Like we're making stock footage to like straight up wartime CEO.

AI assessment note: “Alan was the figurehead of the company. People did not have trust and belief”

Q of questions from our listeners. Most of our listeners are entrepreneurs, whether they're multi-time entrepreneurs or first time entrepreneurs or aspiring entrepreneurs. And I have a, a really interesting question, um, for today's episode that I want to get your perspective on. So Anna Pawsey emailed in and she asked, How do you manage being the boss and cultivating a friendship with your employees? What are your thoughts on this?

A I struggled with this in my first company. I hired all of my friends and definitely burned some friendships that I really miss and I feel bad about. So, uh, if you're listening to this and you're one of those people, I'm sorry. And Um, if you're one of those friends that let me experiment with you on my leadership style and you're still friends with me, thank you so much. Like, thank you. Um, and I think that where I've landed with Prey.com, because I have three other co-founders who are all best friends to me, is just really setting the expectations that we're a team and this is a performance-based organization. I think you have to be upfront and over index on the tough conversations with people. And especially if you're a nice person that really cares about people, like some people, they don't care too much about other people. They really are unaffected by, you know, these relationship, uh, strengths sometimes, um, or strains. I don't know if that, I don't know if strengths is a word, but I think, um, if you're really kind, You have to over-index on hard conversations before they happen. For example, one of my co-founders, Matt Potter, one of my best friends, he let me speak in his wedding. I walked Matt through when we first linked up, because Matt left as the CEO of his own company that was super successful. Shout out to Homestack. Matt left his company to work with me, and…

AI assessment note: “setting the expectations that we're a team and this is a performance-based organization.”

Q I'm sure your cameraman is very grateful for, uh, for the money you paid for him. Um, okay, so that's R.E.P. That's your first business. Now talk about, you said, The agency business was a great start, started really organically with this class at school, but the idea of trading, uh, your time for money was, was a flywheel that you wanted to get out of. So what was next?

A So, um, you know, I, I sat and I thought about it and I was kind of stressed out. I was like laying on the floor in my room and I'm, I'm looking over under my bed and I had all these hard drives, like these one terabyte hard drives, which were like super expensive at the time. And it had all of the extra footage that we hadn't used from all over the world. And I'm just looking at it. And a guy calls me from a TV show and he says, Hey, I know you guys were in Costa Rica last month. Can I buy some footage from you? From Costa Rica. So we don't have to go down there. And I was like, yeah, sure. No problem.

AI assessment note: “a guy calls me from a TV show and he says... Can I buy some footage”

Q So how long were you running that business before you ended up working on something else or stopping working on the agency?

A So, you know, football ended for me and like my last game was Rose bowl, and I had already kind of done that homework assignment and rolled into the company. And so I really figured that company out in 2010. Like it took a couple of years, a lot of like mistakes. And I focused hard on that company for about two years. And we started to scale. We're making money. It was the first time that I was ever making money. And I was like, well, this is super cool, but it was a service business. And what that means is there's only 24 hours in the day, right? To provide service. And if you're not working, you're not earning. And I was, I just felt that pressure and, and I knew I had to come up with a new idea. So it took me from 2008 to 2012, but really I didn't graduate till 2010. So I was like in it hardcore for a couple years. And then I had, I knew I had to come up with a new idea for something that could be a product based business.

AI assessment note: “it took me from 2008 to 2012, but really I didn't graduate till 2010.”

Q say is it feels like a loss of some sort. Like, you know, the only similar comparison I have is stepping out of the CEO role from morning brew and it feeling like this, this void of like, who am I? What is my identity? Who is Alex Lieberman outside of building this business Morning Brew for the last eight years? Was it a similar experience for you in sport?

A Yeah, I mean, you know, growing up, you sacrifice everything to be a great athlete, right? You're not going to parties. You're not going on vacations. In college, you have people traveling abroad, or they're doing interesting things, and you're solely focused on this one thing, right? It's just like entrepreneurship. You start a company, it's your obsession, it's your identity, and you'll hear people tell you, like, Oh, like, don't make this your identity, right? But it's like, yeah, that's nice, but that's not the reality. Like, this is who I am. And when you lose that, all of a sudden, it feels like you have no purpose. You feel lost. You don't know what else to do or what to do next. Like, imagine playing a sport from the time you're six years old until you're 22, and that was the sole thing you're focused on, right? And then all of a sudden it's like, oh, no, sorry, you're done. Figure something else out.

AI assessment note: “when you lose that, all of a sudden, it feels like you have no purpose.”

Q Totally. So, so that's, that's the ad. So you have subscription based, 10% of your content sits there. Then the rest of your content is free, monetized with ads. And then what's the third bucket?

A The third bucket of the business is this ministry SaaS or pastor SaaS business. And, and really that's this core of the business that we're building for pastors. It's the original thesis of, Hey, we're trying to build all these tools for pastors so that they can build a digital church, right? They have their physical church, their analog church that you go to, but what about their digital church? Because For 2000 years, physical church has been great. COVID-nineteen physical church doesn't work anymore. We need a digital church. Same as movie theater to Netflix, right? So this pastor SaaS business or this ministry SaaS business is our third pillar where we build them all kinds of tools so that they can build their own digital church.

AI assessment note: “The third bucket of the business is this ministry SaaS or pastor SaaS business.”

Q next Business was video for it, which was like your aerial stock footage business. Before we get into that, what were one or two of the biggest lessons you learned in that first venture with REP, whether it relates to how to build a great service business, how to find like your early customers when you had no reputation as an entrepreneur, like what were some of your biggest learnings?

A I think the coolest thing about that entire experience, Alex, is it was almost by accident because it started when I was in school. And so it forced me, I was doing these things as, as a homework assignment and it eventually became my master's thesis. And so what I was doing and I didn't realize it back then is I was practicing in public. And one of the things that you do that, like, I admire so much is you post prac you're practicing in public with the plunge, like you're posting the stories on LinkedIn, you're posting stuff about it on Twitter. And that is probably the best thing that you can do when you're an entrepreneur to start. If you just start practicing in public, you're naturally going to get feedback from people. And you don't have to, you don't have to accept the feedback or the criticism, right? But you should listen to it because it's coming from a place where you actually hit on something. And I think if you can practice in public, I think that's the best way to start. And so when you go out, talk to customers, you get it on camera, you post about it, you tell people about your business, like you practice in public. I, I honestly think that's the best way to start a business and just from there you can figure it out.

AI assessment note: “what I was doing and I didn't realize it back then is I was practicing in public.”

Q of it as like these three or And the business before that you thought about it as these like three lines of revenue. Do you think about things in the same way with prey where it's a media company that can be monetized in a number of ways? Just give me a sense of like snapshot of the business today with kind of the metrics that matter most to you.

A Yeah. So today we've got three primary lines of business, right? So, you know, pray.com right in, in the meta version, pray.com digital destination for faith. We are this magnet for people that want to consume incredible faith content. And then within that, we've got our consumer subscription business, which is our premium content that we sell subscriptions to. And that's about 10% of the content in prey. Then we have a bunch of free content that is powered by ads, right? Ad supported is, is what this is often called. And these are original podcasts that we produce. So one example of a podcast that we produce is called Bible in a year. You could go listen to it at Bible in a year.com and Bible in a year is inside of the pray app, but it's also on Spotify. It's also on Apple podcasts. We put ads in there. So we get ad revenue. That's this kind of third part of the business.

AI assessment note: “today we've got three primary lines of business”

Q for an entrepreneur. They'll say, uh, I have a fear of basically being criticized. Like I'm afraid to hit send, um, on my tweet or my video or my LinkedIn post. Or the second, I would say most common one is someone's going to steal my idea. They're going to see what I'm building in public and just go and do the same thing. What do you say to that?

A I think at the end of the day, you have to ask yourself, are you committed to being the best? And if you're committed to being the best and doing the work that it takes to be the best, then if you believe that the best ends up winning in the end, it doesn't matter. And so the requirement for becoming the best ends up being the right feedback and getting the right feedback as fast as possible. Now, not all feedback is the right feedback, right? Like the worst advice is bad advice. Right. So like you have to have a filter so that, you know, like don't accept bad advice or like maybe those people just aren't quite informed. Like we might not even need to put a label on it like good or bad, but feedback, it really is a gift. And so if you're committed to being the best, it doesn't matter if you practice in public. In fact, it's a super advantage.

AI assessment note: “if you're committed to being the best, it doesn't matter if you practice in public.”

Q thesis changed based on what you've learned from the market? So how is pray.com different today from that initial thesis you had of basically being the platform to allow priests, pastors, ministers to create their content that they create for their church, but be able to actually upload it and put it in the single destination. What did you learn that made you have to change course a little bit?

A Our mission at pray.com is to grow faith and cultivate community so that we can leave a legacy of helping others. That's literally what we're here to do. And we're building the digital destination for faith. That's what we're doing. We have an app today. That's the number one app for daily prayer and faith-based audio content. And I learned along the way that like just this massive vision for eight billion people around the world to get hope and inspiration on a daily basis. Like that's awesome, but you have to start somewhere and it's okay to start small. And actually, if you don't start small, you can't get big. So when I came out the gate at pray.com, We raised a bunch of venture capital, so we got all these incredible, intelligent Silicon Valley investors, right? Greylock, Sequoia Scouts, Founders Fund, TPG, Science, like we have these amazing investors, and I came out and realized that I actually just needed to start with like one little thing to get traction. That first thing was a prayer wall For all the churches in the United States to post their prayers and their prayer requests. Cause it's the worst thing in the world. When I send you a prayer request, if I say, Hey, Alex, my mom just got diagnosed with stage four cancer. Will you pray for me? And you're my pastor. And I don't hear anything back. Like, dude, do you think I'm coming back to your church on Sunday when y…

AI assessment note: “realized that I actually just needed to start with like one little thing to get traction”

Q you've just talked about the business part of this, like from a practical perspective, how, how do you think about this from a running the business or not running the business perspective? You haven't mentioned at all, like the grieving process of you lost a mentor and a business partner that you have to deal with at the same time as a 29 year old of making this business decision.

A So I'm, I'm so grateful. I'm so grateful to a guy named Mark Haas that worked for me. He's a former United States Navy SEAL. He's still a Navy SEAL, but he's retired. He, he was on the SEAL teams for like 25 years. Mark Gave me this framework that I use. It's called Mission Team Self. Mission Team Self. And I've adapted it for like my business purposes, not Navy SEAL stuff. You break down your perspective into three perspectives. The mission perspective, like what is our mission? And really that's about the customer. Like, what am I supposed to do for the customer? And that's my priority. The second is team. What's the responsibility to the team? And like team is our company and like usually company. The, the team kind of component or company component comes down to revenue minus expenses equals profit. Like people will throw a bunch of other stuff in there. That's like soft and fuzzy, but like, no, it's literally revenue minus expenses equals profit. And then self is like, how am I feeling like Steve or like as the CEO or something like, and, and so for me, from a mission perspective, I knew we had to keep those flights going. At least the children's hospital flights and the medical flights, like we had to, and really we had to make sure any of the law enforcement stuff was stable. Like we could shut down film production or something like that if we needed to. From a team pers…

AI assessment note: “And then self is like, how am I feeling like Steve”