Alex Lieberman (00:03:21):
And so, basically, I got into my senior year at Michigan. I had my job in hand that I was going to do after graduating from college, which was to trade mortgages for Morgan Stanley, which, again, was me living the dream for everyone else to, like, “What are you doing?” And Austin wanted to be in investment banking. And so, basically, I had all this free time my senior year. I started helping students prepare for job interviews because a lot of students did re-recruit their senior year. And I’d always start by asking the question in mock interviews, “How do you keep up with the business world?”

Alex Lieberman (00:03:53):
And the goal was … this was supposed to be just a layup question, like, let’s shake the nerves, get the conversation going, but every student would have a really interesting thing to say. They would always say, “I read the Wall Street Journal.” Then I would say, “Why?” And they’d say, “I read it because my parents told me I have to, because it’s a prerequisite to say I’m well-read in business, but it’s dense, it’s dry, and I don’t have enough time in my day to read the journal cover to cover.” By the way, I don’t want to knock on the journal because I read the journal, but I think it was fascinating how students would say that.

Alex Lieberman (00:04:23):
At some point, I was like, “This is crazy. This entire generation of people, all these college students are going to go work in banking and in financial services, yet they don’t have content that story tells the business world in a fun and engaging way,” and it just seemed like a complete mismatch to me. You’re going to spend 40 years in business, half your waking hours working in a job and you don’t have content that engages you.

Alex Lieberman (00:04:45):
So I started writing a daily business roundup. At the time, it was called Market Corner. It was actually more markets focused than even Morning Brew was, where the logo was a bear and a bull fighting, but I didn’t have the money to get a designer to design it. So it was literally just a Google image with a watermark going across. And it had all the original DNA, breaking down the biggest stories in 100 to 200-word blurbs. I would do an investor of the stay, a stock pitch of the day, and things like that.

Alex Lieberman (00:05:12):
And basically, what happened was, after a few months of doing this, students started reaching out to me and were like, “Hey, I heard about your daily business roundup. Can you add me to your listserv?” It was, in so many ways, a horrible product. There was no website. It was a PDF that was attached to an email. And so, if you wanted to read my roundup, you had to send me an email to say, “Hey, add my email to your listserv.” Despite all that, a couple thousand people subscribed to it.

Alex Lieberman (00:05:38):
And to me, that was enough proof of concept to say, “Okay, there’s something here because people shouldn’t be signing up for this thing. It’s impossible to sign up for.” That’s when one of my readers, Austin Rief, sophomore at Michigan, reached out to me and was like, “Hey, love what you’re doing with Market Corner, but I have some ideas to make it better,” met up in the main area of the business school at Michigan, and he basically gave me all of these thoughts for what could level up the product.

Alex Lieberman (00:06:03):
And I didn’t realize it until then, but one of the worst things when building a business or, honestly, anything that involves intellectual rigor is being told by people that you’re doing a great job is wildly unhelpful. And so I’ve been told over, and over, and over what I’m doing is great, keep it up, keep sending out this newsletter. Austin was the first person to be like, “Yeah, this is good, this kind of sucks. This is good, let’s change this up.”

Alex Lieberman (00:06:26):
I ended up bringing on Austin as my co-founder. We launched Morning Brew as a proper email newsletter, not a PDF, in March of 2015, and we’ve been doing it since then. So the business has been around for six years. We officially turned six this past weekend and it’s been quite a journey.

Trey Lockerbie (00:06:43):
Something I heard you talk about, or maybe Austin mentioned, about strategy with the product, now that you’ve got this product and you’re sending it out, something that’s really stood out to me that I thought was a great strategy is the testing involved with the headlines and the subject matter. So talk to us a little bit about how you approach that.

Alex Lieberman (00:06:59):
It sounds so small and insignificant, but subject line testing is actually a really meaningful thing for our business. When you’re sending out to 2.7 million people every day, the difference of a .1% to .5% difference in subject line is tens of thousands of readers, which actually equates to advertising dollars. And so what we do is our newsletter is sent out at 6 a.m. Eastern, Monday through Saturday. At 5 a.m, we send out four subject lines, an A, a B, a C, and a D, to different 20,000-person groups.

Alex Lieberman (00:07:35):
Basically, what we see is, when we send that newsletter out at 5 a.m. to those four 20,000-person groups, by 6 a.m, what is the group that has the highest open rate? Whatever group has the highest open rate, we take that subject line and we send the remaining 2.6, 5 million people that subject line. And that has accounted for hundreds of thousands of dollars over time because one of the ways that we charge advertisers, or we have in the past, is based on opens of the newsletter. And so we’re incentivized to get as many people to open the newsletter as possible.

Alex Lieberman (00:08:06):
Also, just thinking from a human behavior perspective, we live in the age of abundance. Right? One of the things that platforms have done, that the internet has done, is made it easier than ever for creators to create content. And so, for us, it just means we have to work harder than ever before. Every media company has to do this. We have to work harder than ever before to compete for people’s attention because, when they’re opening their email every day, their inbox is going to have 100 emails.

Alex Lieberman (00:08:35):
Even if we are a staple in their morning routine, we still need to fight for their attention because, by the way, we’re not just fighting against The Wall Street Journal or other email newsletters, we’re fighting against someone deciding to do a Headspace meditation. Not saying people shouldn’t do Headspace meditations. Or fighting against someone playing Fortnite or fighting against someone reading a book. And so I think, when you’re in the world of media, you realize the all-out battle isn’t for subscribers or for subscription dollars. It’s the battle for attention and time.

Trey Lockerbie (00:09:07):
So starting out with this newsletter, I imagine it just started gaining more and more traction. At some point, you probably needed to raise some money. So just being right out of college, how did you approach that?

Alex Lieberman (00:09:19):
We had never raised money before. The way we had funded the business was basically a combination of money that Austin and I had made from internships. And then this was one of the benefits of building a company in college, is you just have a lot of resources at your disposal. We basically applied for every grant humanly possible on Michigan’s campus to help us fund the business. By the way, it’s also one of the reasons we chose email as our distribution for our content, because email was really cheap relative to building an app or something.

Alex Lieberman (00:09:49):
At some point, when Austin and I decided to go full-time … So I had quit my job working at Morgan Stanley in September of 2016. Austin knew that he wasn’t going to accept his full-time job to work in investment banking. We were like, “Okay, we need to take this thing seriously,” because we’re going from this newsletter that had, at the time, 70 thousand subscribers. We have to turn this kind of cool, nice side hustle into a business. And for us, what that meant is we had to do three things extremely well; create great content, scale our audience, and monetize that audience by convincing the biggest brands in the world why they need to pay to get in front of that audience.

Alex Lieberman (00:10:26):
And we knew that we needed to hire writers, we needed to hire people to grow the audience, marketers, we had to hire salespeople, but it was a chicken and the egg problem because we weren’t monetizing the business yet, so we didn’t have ad dollars in order to invest into hiring people. So basically, we said, “We have to raise some money.” Originally, I think our number was 250K we were going to raise. And then we spoke to someone about it and they were like, “There are just so many costs you’re not accounting for right now. Just trust me.” I can’t remember who that person was. And so then, we were like, “Okay, we’ll raise 500K.

Alex Lieberman (00:10:56):
We ultimately raised 750K. And the way we did it was we raised 750K in the form of a convertible note. And we didn’t raise from institutions or VCs for two reasons. One is we had no relationships to them, so we felt like we would be starting from scratch. The second reason is Austin and I just had this kind of naïve view in our minds that, if we raised from VCs, they’re going to suck our soul out, we’re not going to be able to control our destiny. In all fairness to VCs, I know several VCs now that are not that way at all, but that was our just view of the world.

Alex Lieberman (00:11:30):
And so what we said is, “What’s the easiest way for us to raise money from non-institutions and non-VCs?” It made the options pretty small because, by the way, another option was raising debt. Where were we going to be able to raise debt for a business that had no cashflow? And so we ended up doing something, I think, that was pretty clever, which was, in the early days of Morning Brew, we would interview, on a weekly basis, successful business people and successful investors. So we interviewed everyone from the owners of the Minnesota Vikings to the founder of the Snuggie, to the former CEO of Time Warner Cable, to the creator of MTV.

Alex Lieberman (00:12:06):
And when we went to raise money, we basically said, “Hey, we have that spreadsheet of those 25 people that we interviewed in the early days of Morning Brew. They seem to be really successful, they seem to have a lot of money. Let’s go talk to them.” And so, basically, that was the foundation of who we pitched, was leveraging this network of 25 people that we interviewed for our newsletter and then anyone in their network that they would introduce us to. We ended up raising the 750K from 28 individual investors, so 28 individual checks, in early 2017.

Alex Lieberman (00:12:38):
And the very interesting thing about it was twofold. One is several of the investors, honestly, I think they were investing for nostalgia as much as they were investing for return. And things worked out in a really cool way where, as a function of selling our business, they saw return I don’t think they were ever expecting, but also the other learning is we didn’t realize just how much maintenance there is to when you are raising money. Those were our first shareholders, in a way. Even though they were convertible note holders, so they were technically debt holders, they were going to be debt holders that convert to equity holders. So those were our shareholders.

Alex Lieberman (00:13:13):
And I don’t think we realized, at the time, how much time and effort would go into keeping up with them, updating them, making sure their documents were all right. We wouldn’t do anything differently, but maintaining legal docs and updating 28 people and trying to get 28 people on a call or a Zoom for an investor update, absolute nightmare.

Trey Lockerbie (00:13:34):
Not a lot of people realize, and we’ve got a lot of entrepreneurs in the audience who may or may not have raised money yet, there’s so much psychology that goes into raising money. One that stands out to me is the social proof aspect of it. Right? Because you mentioned the 28 checks you raised. Tell us how important it was to get five of those checks, the small checks, and then go to people and say, “Look, we’ve got X amount committed. Are you in or out?” Just building from a small nothing to something big is important.

Alex Lieberman (00:14:01):
It’s such a good point because I want to say, all in all, it took us four months to raise the $750,000. I think it took us probably three months to get the first check. And I will forever remember our first check. I was in a coffee shop in Brooklyn and it was one of these people I mentioned, who was a former executive a Time Warner Cable. I’m on the phone with him and I’m sitting by the bathroom in this coffee shop pitching myself, Austin, the business. And the call finishes with, “I’ll invest 100K. Just let me know how to do it.” And it was just like, not only pure adrenaline, it was also crazy to me, I’d never met the person in-person. And so, to be like, “Wow, I convinced someone who I’ve never met in-person to put 100K into the business.” That’s an awesome feeling.

Alex Lieberman (00:14:49):
But, to your point, it provided incredible social proof because now, every time we sent our investor deck out, we could say, “Former CEO of Time Warner Cable is invested in the business.” It provided legitimacy in two ways. One is because no one ever wants to be the first check in in such an unproven, pre-monetization business.

Alex Lieberman (00:15:09):
The second is, especially because someone had put a check in, but it was also a qualified check, it was a strategic check from someone who knew the media world so well, it was validation for a lot of people who were saying, “I know nothing about media. And if I’m going to make a bet on a media company, am I going to do it on two students who have never started a company before, who are going against The Wall Street Journal?” Think about how hard of a pitch that is. When we had this guy on board, it made it a lot easier because they’re like, “He clearly knows something that we don’t know.”

Trey Lockerbie (00:15:38):
Well, it’s that Zero to One philosophy, right? Going from zero to one is the hardest, which is a great book, by the way, by Peter Thiel, for all the entrepreneurs. I feel like, if you read Zero to One and you still want to start your business-

Alex Lieberman (00:15:50):
You’re slightly crazy, but you’re in good shape. You know what to expect.

Trey Lockerbie (00:15:54):
Well, I think someone in that pool of investors you were approaching early on was Mark Cuban. So talk to us a little bit about that experience.

Alex Lieberman (00:16:02):
One of the first people that I had reached out to about … And it wasn’t even about investing, at the time. It was when we had 1,400 subscribers. And I’d reached out to Mark Cuban because, as a longtime Shark Tank watcher and I also just really respected what he had built … I think I still have the email from him. I’m trying to pull it up. I reached out to him, basically, just saying what our business was. I said, “We’re a newsletter,” everything that I’ve described. “We are trying to make business digestible and approachable and conversational for this emerging generation of business leader, who is going to run companies in the next five to 15 years.”

Alex Lieberman (00:16:41):
And it really is crazy when you think about it. By 2030, 80% of the working population will be millennial of gen Z. And so there’s this massive wealth transfer happening. Obviously, I didn’t say it in that way to him, but I said what we’re doing. And his email back … First of all, I was blown away that he emailed me back, but then he was basically like, “I don’t get it.” He was like, “There’s so many newsletters out there. What makes you different?” I talked about our voice was different, curation was different, there was this sense of community. And he was just like, “I still don’t understand how it’s different.”

Alex Lieberman (00:17:13):
And to be totally honest with you, if I was in Mark’s seat, I probably would’ve said the same thing because I think, in a lot of ways, in media especially, your moat as a business is your brand and your ability to connect with an audience at a deep level. And especially if you are not in that audience, I think it’s actually a really … it’s a blind spot. Mark wasn’t the 25 or 27-year-old young business professional who don’t necessarily like combing through the journal. They want to feel like they’re having a conversation with a friend after work at a bar.

Alex Lieberman (00:17:48):
And since he didn’t have that vantage point, by the way, I think that’s, in a lot of ways, why we had so much opportunity with Morning Brew, because I think Mark Cuban and a lot of people of his ilk never thought that, “Oh, The Wall Street Journal or The Economist or The Financial Times isn’t serving this audience.” That was never a question in their mind because they weren’t the audience. But honestly, in a lot of ways, I’m just thankful that he responded to me.

Alex Lieberman (00:18:11):
I think this happens in a lot of industries and I think, from an investor’s perspective, it’s a really interesting place to think about investment, which is what are industries that have moats or defensibility that actually is kind of fake or a little bit of smoke in mirrors? And I think, the world of business journalism or business media, I think a lot of people assume no one is ever going to take audience from The Wall Street Journal or Bloomberg. These institutions have been around for a century.

Alex Lieberman (00:18:40):
I don’t think what they realized is that The Wall Street Journal has never been serving our audience, has never been serving the 25 year old. The 25 year old has been reading that content out of necessity because there’s nothing else available, but The Wall Street Journal’s core customer is the 48 year old who’s been working in business for 25 years. And by the way, that’s why it gave us opportunity, because it’s never going to be The Wall Street Journal or X traditional business media company’s prerogative to go after the 25 year old today because they risk alienating a more valuable audience.

Alex Lieberman (00:19:11):
And I think that’s almost one of the paradoxes of large legacy businesses, is how do you build innovative products for a young and up-and-coming audience when you don’t want to alienate your more valuable audience today?

Trey Lockerbie (00:19:25):
I’m curious if that early no, quote unquote, from Mark Cuban drove you, in any way. Right? Some of the times, those early nos as an entrepreneur are so important. And I commend you for not letting that knock you back. Instead, it seems like it kind of fueled you forward. And it reminds me of a fellow Michigander, Tom Brady, who was the 199th NFL draft pick, who goes on to become who he is. Sometimes those early failures lead to successes.

Alex Lieberman (00:19:54):
I think, in a lot of ways, every entrepreneur has a fire. And it’s a question of where that fire comes from. Right? Sometimes it’s intrinsic, sometimes it’s created by your surroundings. I think, for me, it was a little bit of both. Right? I think I just had this competitive spirit from growing up playing sports. I think things like interaction with Mark … And that was one example. You can assume there were dozens of other ones like that when … in the early emails that I sent. I think those were all the extrinsic things or just the things that happened that just added more and more of a chip on my shoulder.

Alex Lieberman (00:20:30):
There was another side of me where … Honestly, I lost my dad when I was a junior in college and I think that changed my perspective around everything where, in some ways, it created this idea in my mind that, now, I have to be the breadwinner in the family. I need to take care of my family because, by that point, my mom had retired. There’s only money going out. There’s no money coming in. And whether or not the narrative was true, I think, in so many ways, that’s what drove me to operate at such an intense level for so many times, is there’s no other option but to have this succeed because I have this deep vision in my mind of giving my mom a check, my grandpa a check, my sister a check, and knowing they’re going to be fine for the rest of their lives.

Alex Lieberman (00:21:15):
And I wouldn’t say every entrepreneur has a story of trauma, although I will say I have met, proportionately speaking, a lot of entrepreneurs who have gone through some form of trauma or challenge relative to non-entrepreneurs that I’ve talked to, but I do think every entrepreneur has a fire. And the question is, where does that fire come from?

Trey Lockerbie (00:21:34):
It reminds me of billionaire Ray Dalio, who we study a lot on the show. His book, Principles, he talks about these two types of people in the world; those who are achievement-oriented, finding their own hero’s journey of sorts, and those who are more present, who cherish the nuance of everyday life. And while they aren’t mutually exclusive, entrepreneurs inherently embark on that hero’s journey. Right? And a critical milestone in the hero’s journey is this abyss that they enter into or otherwise known as the trough of sorrow. And this is more related to the actual entrepreneurial journey that you went through. So I’m curious about Morning Brew and if you had an experience where you felt like the company was entering this trough of sorrow of sorts that you had to climb out of.

Alex Lieberman (00:22:21):
Things really accelerated in our business in the last two years, just to give a sense of trajectory. It was like revenue in the business in 2018 was $3.5 million in revenue. In 2017, it was $175,000. That was the year that we raised the money. 2019 was $13.5 million. 2020 was $21 million. And so, if you look at it, the last three years of the business have really become us being a business. We went from a seven-figure business to an eight-figure business in the last two and a half years and we’ve been in business for six years.

Alex Lieberman (00:23:02):
So the first three and a half years of us being a business was scratching and clawing. We were scratching and clawing for everything; for every subscriber, for every dollar. And we never lost faith. We never though that the business was going to fail. We just didn’t think we were going to be a massive business tomorrow, but it was like we didn’t have this timeline in our head. Our view is almost like, however long it takes, we’re just going to keep scratching and clawing and building until this is something really meaningful.

Alex Lieberman (00:23:29):
And so the fact that everything has accelerated in the last two and a half years, and we sold a portion of our business, that’s icing on the cake and it’s a wild journey to realize, but yeah, in the early days, honestly, it was a lot of just thankless content creation where we were just putting out this newsletter every day, hoping that we would get a couple hundred subscribers. In the early days of selling ads in our newsletter, I remember our first ad we ever sold was an $800 ad, I think, to the University of Virginia. Now, someone wants to advertise in Morning Brew, you’re doing a full takeover of our newsletter, it’s close to $100,000 a day.

Alex Lieberman (00:24:05):
I think what this all says to me is you kind of have to have a screw loose, in my mind. It’s like you have to have this uninformed hope that things are going to work out, that, no matter what happens, things are going to work out. We always had that view, but then also have respect for the journey and enjoying it. If we didn’t enjoy pumping out the newsletter every day, figuring out partnerships to grow it, thinking about what brands we should go to monetize, the actual act of zero to one building, we didn’t enjoy that, we would’ve never gotten here.

Alex Lieberman (00:24:38):
And so, to me, I think that’s what happens to a lot of entrepreneurs, is they have this big vision, they have the first part of it, but they don’t enjoy the journey enough. They don’t realize how much of a grind it is. If you don’t have just an appreciation for that grind and a levelheadedness to not get whiplash from the highs and lows of it, it’s like a rollercoaster. It can make you sick. And I think, for us, the first three and a half years was a time of we don’t have a big business, we’re paying ourself fine money, we don’t have any perspective yet that this is going to be something huge that’s going to be a life-changing endeavor, but we were just loving it and we were loving it more than the jobs we were doing prior. So to us, the opportunity cost was low, is go back to something that we didn’t enjoy as much.

Trey Lockerbie (00:25:24):
First of all, I’m just not sure people realize that this is available to them, that you can start marketing pretty cheaply and test pretty accurately very early on, nowadays. It’s a huge advantage that most companies may not be taking advantage of. Is that something you guys adapted very early on?

Alex Lieberman (00:25:39):
The reason we got involved in paid marketing early on is because it is so approachable. And again, when people are wondering, “Why is Facebook valuable? Why is Google valuable?” these are the largest platforms on planet Earth that have hundreds of millions, if not billions, of people. And you, as a small business or a large business, have the ability to spend anywhere from tens of dollars to tens of millions of dollars in a week on these platforms, getting in front of your audience.

Alex Lieberman (00:26:06):
And so, to your point, it was very easy. In a lot of ways, these platforms goals are to make it as automated as possible where you can set and forget their platforms. You decide you want to spend $10 in a day, well, they’ll be able to test that $10. You literally have the ability of creating … Let’s just say, for Morning Brew, we could tell Facebook, “Hey, we’re going to spend $100 this week and we want you to test three different types of creatives, so three different looks of ad units that can be sent to our audience.” Maybe one will say, “Get smarter today.” Another one will say, “Be a better investor today.” And maybe the third will say, “Be a better entrepreneur today.”

Alex Lieberman (00:26:44):
And Facebook is smart enough to get in front of the right audiences, test that creative, and test that creative with, say, only $2 of spending. And after spending $2, know whether the, “Get smarter,” “Become a better investor,” or, “Be a better entrepreneur,” is going to get a cheaper subscriber and will put the remaining $8 in that winning creative. And I don’t think, yeah, to your point, people fundamentally understand how powerful these advertising platforms are.

Alex Lieberman (00:27:11):
And to your point, also, I don’t think people truly understand how every company in the world is becoming a media business or an audience business, whether it likes it or not. Everyone from, obviously, there’s the argument about the Facebooks of the world being media businesses, all the way to the largest investors in the world are becoming media businesses. You look at Andreessen Horowitz, they have a full-blown media organization now and there’s a reason that they’re doing that, because they think the investment in owning their own audience is worth enough to generate leads for potential portfolio companies or people that they’ll hire into their business or for raising new funds.

Alex Lieberman (00:27:48):
Every company is turning into a media company because what they’re realizing is, while all these platforms like Facebook or Google are great places to start paying for marketing, you also realize that paying for marketing is really, really expensive and you don’t own the audience.

Trey Lockerbie (00:28:03):
Yeah. And it reminds me of even someone like Warren Buffett, who is a marketer. I mean, if you really think about it … He’s obviously on CSNBC a lot. He’s obviously an educator and loves educating people, but that also provides this amazing opportunity for him to market his brand. And if you go to one of his Omaha events, he’s pitching. He’s like, “Call me. We’re looking for acquisitions and you want to be part of the Berkshire family.” I mean, it’s a big marketing effort and a huge media empire of sorts he’s built, in that way.

Alex Lieberman (00:28:34):
I think it is actually a really fascinating time to think about this intersection of financial instruments, financial services, and media and audience because I think you’re seeing some of the most successful entrepreneurs in the world and some of the most successful investors in the world that are leveraging their personal brand and media to use that as a top of funnel for their financial instruments or financial services. Right?

Alex Lieberman (00:28:56):
You see that everywhere from some of the biggest holders of Bitcoin are touting Bitcoin on Twitter and, I think, are truly moving markets from the brands they built up on social platforms all the way to Chamath, who is the CEO of Social Capital, has become the SPAC king. And now, it’s like he’s built a direct-to-consumer relationship with potential investors or people who have intersect in SPACs where it’s like, now, he is literally posting on Twitter. When he goes to SPAC a company, he writes out his investment thesis and posts it on Twitter. There has never been a more direct relationship between investor, entrepreneur, instruments provider, and consumer.

Alex Lieberman (00:29:38):
And I think that creates a really interesting and exciting opportunity, but I also think it brings questions of, at what point is there going to be regulation around a lot of this? Same thing with Elon. Elon Musk is, to me, media company first and electric vehicle CEO second.

Trey Lockerbie (00:29:54):
Or Dogecoin promoter, nowadays.

Alex Lieberman (00:29:56):
Yeah. Dogecoin promoter, number three.

Trey Lockerbie (00:30:00):
So talking a little bit about Warren Buffett, I want to kind of just frame up here why we’re talking about your business so in-depth because my philosophy comes directly from Warren Buffett, which basically is, in order to be a great investor, you have to understand business and you have to study businesses like they’re species of animals. And that’s what I’m trying to do here, is figure out kind of the recipe for success that Morning Brew has had.

Trey Lockerbie (00:30:24):
One thing I’m really curious about with the success of Morning Brew is that it seems to really come from the tone, you mentioned, or the voice that you’ve mentioned. And I don’t think people quite recognize how maybe hard it is to distill or filter everything through a certain voice and have basically brand pillars in place that you honor with every word that you pick, like poetry, right? That’s the brand and that’s the essence. So what are the pillars or what is the filter that you use? Talk to us a little bit about that.

Alex Lieberman (00:30:54):
To me, actually, Morning Brew’s job is the same job as an investor. We are master curators. I think there’s two types of currency in the world. It’s money and time. And for us, people have trusted us with their time. Right? They trusted us to sign up for our newsletter and they trusted that, every day that they open our newsletter, that we have respected their time and we have been, basically, their internet shirpa to decide all this stuff that’s happening on the internet, all this content that’s being created, what is worth their time so they won’t be caught off guard in a conversation with a boss or a coworker.

Alex Lieberman (00:31:32):
And so we are acting as the curator where we’re looking at the 15 things that they could care about, that could be worth their time, and we’re deciding what are the four or five that are worth their time and how do we provide it in a digestible and witty way that is going to keep them engaged? And in the same way, at least when I think about investing, for example, to me, investors are marketers and curators. They have to market to raise their funds and then they have to curate, based on the remit of their fund, out of the 50 different companies, 100 different companies that they could be putting their money to work in or their investor’s money to work in, what is the best use of their investor’s money?

Alex Lieberman (00:32:14):
To me, Morning Brew is what is the best use of our readers’ time. The best investors are the best curators in the world. And I think curation only gets more important. As there’s more choice in the world and as there are more tools for businesses to be created, for startups to be started, for content to be created, the act of great curation, knowing who your audience or your customer or your investor is, only gets more valuable. I don’t think people truly grasp why curation is so valuable.

Trey Lockerbie (00:32:44):
I love that point, absolutely. It goes back to the moat that Warren Buffett talks about. You mentioned it earlier, that voice, because I imagine there’s a lot of competitors that have entered this space with the newsletters, especially seeing some of your success. So does that filter into your mind at all, as far as who you’re competing with, or is it just full speed ahead, we’re very myopically focused on our mission?

Alex Lieberman (00:33:09):
So how I think about competition is, no, no decision we have made as a business, generally speaking, has been impacted by competitors. The only time we really think about competition is, when we’re thinking about launching a new product, there’s a consumer need or problem that we’re interested in solving and we think our competitors are already solving it well, then maybe we think to ourselves, “Is this the best place for us to play?”

Alex Lieberman (00:33:33):
But other than that, none of our strategies, as a business, really has been dictated by our competitors. I am sure, as you become larger and larger, it becomes more of a consideration, but for us, the world of media and business media and content consumption is so large. We are still minnows. And if you’re a minnow in an ocean, your time isn’t best spent trying to bite other minnows. It’s trying to explore the ocean and try to not get eaten by sharks.

Alex Lieberman (00:33:59):
And so, for us, the way that I think about our competitors, just so you have a sense of how I think about competitive sets, the first circle to our closest competitors are other business newsletters; Wall Street Journal’s newsletters, the newer digital age media companies’ newsletters like The Hustle or Finimize or Robinhood Snacks. Then there’s this second circle, which is what I would say are non-business newsletters and business non-newsletters.

Alex Lieberman (00:34:25):
And what I mean by that is non-business newsletters are newsletters like The Skimm or Axios’ newsletters. Basically, newsletters that are not the same, but they serve a similar need where if someone’s like, “I just want to get updated on my day,” and they don’t necessarily think it has to be about business, it could be about politics or pop culture, we could lose our reader there. Other example is non-newsletter business. And that would be like listening to New York Times Daily or Wall Street Journal’s Podcast, like a different media format that still competes for our readers’ time.

Alex Lieberman (00:34:58):
The third circle is, what I would say, is the least similar, but actually is just as competitive, which is what are all of the things in someone’s morning routine that compete for your attention? And that could be the book you’re reading, that could be playing Candy Crush, that could be, like I said earlier, listening to Headspace. That is the fundamental think that I think every business builder needs to think about, is what is growing is choice, choice of product, choice of content, choice of businesses that you can be affiliated with, but consumers’ time is as scarce as its been and it will continue to be that scarce.

Alex Lieberman (00:35:34):
I think it’s the fundamental question that every business has to ask itself, which is not just what problem are we solving, but also does our consumer have the space in their 24 hours of their day for us to solve that problem? Because we could be the best damn newsletter, but if it is not a problem that is big enough, that is worth our reader’s time in their day, at the end of the day, we’re competing for the same 30 minutes in someone’s morning commute that someone else is. And so I just think people need to respect scarcity of time when thinking about what they’re trying to do. They have to think way more about that than they have to think about are they out-competing a similar firm?

Trey Lockerbie (00:36:09):
I love that. And you can apply that to other businesses, as well. For example, my business is a beverage business. So instead of thinking about time share, we think about stomach share. It’s not like anyone’s drinking a Kombucha or adding it on top of the other sodas that they’ve been drinking. Typically, they’re replacing something with something else because you have a finite amount. That’s really interesting.

Trey Lockerbie (00:36:28):
I’m wondering about that competitive landscape you mentioned and the advertising dollars that go to all of those players. Being a leader in the space, are you able to have pricing power when it comes to advertising or is there just a big democratization of advertising across all these media platforms now?

Alex Lieberman (00:36:47):
I would say we have pricing power because we have loyalty. And I think this honestly goes for any business. It’s like, when you have loyalty and you have retention, you can continue to increase price. If that’s part of your brand and your brand is about being a discounter, then obviously that’s going to be different.

Alex Lieberman (00:37:05):
But for us, at the end of the day, if you are a company that is looking to get in front of the young 30-something-year-old profession who’s working in finance, investing, tech, consulting making six figures a year, who has big life moments coming up, putting their money to work or getting married or whatever, moving into a home, having a child, there are only so many places on the internet that you can do that in a high-impact way. You can’t go to The Wall Street Journal or places like that because that’s not the average audience.

Alex Lieberman (00:37:34):
If you go to Facebook or you go to Google, you can get in front of that audience, but it’s not going to be high-impact because it’s not like the consumer I just described has this love for Facebook, where they’re going to be seeking out the advertisements that Facebook is serving them.

Alex Lieberman (00:37:47):
And so I think the reason we have pricing power is actually less about our size. It definitely has helped us going from originally 100,000 readers to now 2.7 million subscribers, definitely gives us more credibility to say we are an at-scale player. There is definitely an aspect of that. And it really happened when we hit 500,000 subscribers, but I think it’s the fact that we just have a deeply engaged audience.

Alex Lieberman (00:38:10):
To give you a specific example, in the email newsletter world, a 20% open rate, so 20% of your subscribers opening your newsletter, is considered good. That is the average. Morning Brew’s continues to be twice the average. We’re 40% daily unique open rate. And it’s just like numbers don’t lie. And when you have a conversation with a brand and they realize that Morning Brew is one of the only places on the internet that has the loyalty of the emerging business leader for five to 10 minutes of their day, it makes pricing really easy because …

Alex Lieberman (00:38:42):
I’ll give you the example. If I am IKEA and I’m talking to Morning Brew and Morning Brew tells me, “Hey, IKEA. We have this audience. 75% of our audience tells us that, in the next five years, they’re going to move into a home or an apartment. They’re going to have furnished their home and they don’t yet have loyalty to any brand. And by the way, IKEA, we’re talking to Crate & Barrel next week and either of you would have the opportunity to build habit with this first-time home buyer,” it puts IKEA in a really tough position where they’re like, “Well, Crate & Barrel could start working with Morning Brew and start to build loyalty with a totally new generation of consumer or we can. And if we don’t do it, where else are we going to do it?”

Alex Lieberman (00:39:22):
And so I think there’s this pent-up appetite or this price inelasticity because you have a lot of brands that do have marketing budgets to put to work, but there actually isn’t so much choice to get in front of an entire generation of people that are going to have a lot of money to spend in the next few years.

Trey Lockerbie (00:39:41):
Well, I found it interesting that you referred to Morning Brew as a minnow in the ocean because you recently sold a majority of stake in the business to Business Insider for $75 million. So that’s a big chunk of change, especially for someone … Are you under 30, by the way?

Alex Lieberman (00:39:59):
Yeah, I’m 27.

Trey Lockerbie (00:40:01):
Amazing. So talk to us about that decision, how they came around or came to the table. What made you go that route?

Alex Lieberman (00:40:09):
The first thing that I would say is this deal re-validated for me how important relationship building is. And I think, for a little while, not that I was skeptical of it, but I was wondering to myself, “Is that considered old school?” People talk about, in the old days, building your Rolodex and all these things. Is that as important in a connected age of social media?

Alex Lieberman (00:40:31):
And I would say what this deal validated for me is relationship building is more important than ever before. Maybe the way in which you relationship build, like the forums in which you do it, maybe now it’s more so done on Clubhouse and Zoom versus just handshakes in a restaurant. It’s probably a combination of both, but the reason I bring that up is the way our relationship originally started with Business Insider was almost probably two and a half years ago.

Alex Lieberman (00:40:58):
And it was in the days of we were still in zero to one for Morning Brew and we were trying to fight for every subscriber. And one of the things we tried doing when we were fighting for every subscriber is we reached out to big media companies and we were like, “Hey, can we strike a deal together? Is there any way that Morning Brew could be distributed on your website?” And we had reached out to Business Insider because they get hundreds of millions of people to go to their website every month. We thought, “Wow, this is an amazing marketing funnel of people who care about business.”

Alex Lieberman (00:41:25):
And so, at the time, I was talking to one of their editors and I kept bothering him over, and over, and over, “Hey, can we partner? Hey, can we partner?” And at some point, he just foisted me on another person. He foisted me on the person at the time who was running consumer subscriptions for Business Insider, this guy, Claudius. And there was no agenda, other than to talk about partnership and meet each other, but once I was introduced to Claudius, we met up on Stone Street in the Financial District of New York City. At the time, Morning Brew was in its original office in WeWork. And Business Insider was also in the Financial District.

Alex Lieberman (00:42:00):
We got beers. We talked about media, the history of media, where media’s going. And then we just kept in touch, from that point on. We would do home-in-home ping pong matches where Claudius would come to WeWork. He would play ping pong there. I’d go to Business Insider, play ping pong there. And basically, it was just like a friendship with a peer in the industry for probably a year and a half before any sort of serious conversation started. And it was around the beginning of 2020. That’s when any sort of conversation around what could a bigger partnership look like.

Alex Lieberman (00:42:30):
Ultimately, it took several months, probably 10 or 11 months, for the deal to actually happen. And Austin and I had never been through a deal process before, so never had a sense of how long it would take, but it definitely went in ebbs and flows. It was almost like a little business, in itself. It was a rollercoaster and I think it was a magnified rollercoaster because March, 2020, is when really everything happened with what was going on in the world.

Alex Lieberman (00:42:54):
And so it went and ebbed and flowed, but I think this thing that stayed consistent, which is why we saw a ton of opportunity, was because everything that Business Insider was is what Morning Brew wasn’t and everything that Morning Brew was was what Business Insider wasn’t. And what I mean by that is we’re both media companies, but we couldn’t be more different. Business Insider has built just an incredible brand and business off of, one, great journalism and a great newsroom. Morning Brew does not have a newsroom and we’re not journalism, per se. We are curation remixing and some original content, original analysis, but we don’t break news. Business Insider’s focus has been on website content and social media. Morning Brew’s focus has always been on email and then podcast.

Alex Lieberman (00:43:43):
And so I think, in so many ways, we saw these complementary assets where Business Insider really wanted to get into the email game, but they saw a partner who had figured it out. We saw, for ourselves, as Morning Brew, that we wanted to evolve from a newsletter business where you go on the streets of New York, you ask someone, “What is Morning Brew?” nine times out of 10, you would hear the answer of, “Oh, it’s like The Skimm, but for business,” or, “It’s that newsletter company,” we knew we wanted to evolve into a media brand.

Alex Lieberman (00:44:08):
And so, for us, we were excited by this fact of this company that started as a newsletter in Henry Blodget’s apartment has evolved into a full media company. There’s so much we can learn from them in how they set the foundation for growth. And for them, as they think about do they buy or do they make newsletters and podcasts, I think they saw a ton of opportunity in us. And again, going back to this idea of how important it is to build loyalty with an audience and being obsessed with that, that’s what they saw in us, is they truly saw that we built an obsessive audience. And when you have an obsessive audience, there are so many things that you can do with it.

Alex Lieberman (00:44:44):
And so that was always the thesis, was this complementary nature of our businesses. The deal closed in October of 2020 and, so far, it’s been a great partnership where everything they promised that we could do is what we’ve done. I think people in media get worried about acquisitions or investments and there’s generally three types of flavors. There’s vertical, there’s, I would say, more private equity-esque in nature, and there’s synergistic.

Alex Lieberman (00:45:11):
So vertical is what Barstool did. Barstool being acquired by Penn National. And the whole idea was Barstool was this huge, top of funnel for sports gamblers, for people interested in sports. Penn National wanted to grow its digital gambling presence. The whole idea was Barstool would be this great top of funnel. We’ll see over the long term how it does, but if you look at Penn National’s stock since the acquisition, I believe it has significantly outperformed the S&P and just any other comps in the sports gambling space. That’s a vertical.

Alex Lieberman (00:45:44):
Then you have a private equity style acquisition. And I think this is the one in media that people get really worried about, which is private equity firm buys two or three media companies, basically centralizes all of their main functions, HR, sales, finance, editorial. A bunch of people get fired. It’s not fun for everyone. Melding of cultures becomes a really difficult problem. That’s, I think, what everyone assumes when they think acquisition in media.

Alex Lieberman (00:46:13):
The third is more synergistic or horizontal in nature, where it’s similar playing field, similar types of companies that are complementary. And when you bring them together, they can learn from one another and they can also basically contribute to a larger whole in areas that each one has a blind spot. And that’s what it’s been for us and from the early days. Austin and I, as entrepreneurs, said it pretty overtly when we were talking about any sort of deal that we need to have the freedom to continue to build and to control our own destiny and guide the ship. That’s why we love coming into work every day and we don’t want to mess that up.

Alex Lieberman (00:46:46):
And I think what’s been awesome is they’ve truly respected that. I think, because Henry Blodget, himself, is an entrepreneur, he’s been building Business Insider for a long time. And Axel Springer, the German media conglomerate that owns Insider, is a very acquisitive company, as well. I think they’ve done 200 acquisitions in the last five years, maybe. Everyone was on the same page about being founder and entrepreneur friendly. And unless things aren’t going well, we have our game plan, let’s stick to it, and they’re always there as a resource if we need help.

Trey Lockerbie (00:47:16):
Amazing. Well, congratulations. Well, now that you have some resources of your own to put to work, have you thought about your own investing approach or your own portfolio? What’s taken your interest?

Alex Lieberman (00:47:28):
It’s a great question because I think there’s a few options that I’ve been thinking about. One is, how much do I do my own angel investing? That’s been a part of my mindset. How much do I just write checks into startups that I believe that I can provide a strategic lens, as they think about building audience or marketing, et cetera? The other is, how much should I be thinking about putting money with professionals that are spending all day long thinking about putting money to work?

Alex Lieberman (00:47:54):
And then there’s another model, which I’ve just thought about, which is starting my own fund of sorts. It’s something my co-founder, Austin, has done. He started a rolling fund on angel. We’ve seen people start rolling funds, as well.

Trey Lockerbie (00:48:07):
Talk to us about that. Maybe describe to the audience what that is because I only found out about that recently. It’s fascinating.

Alex Lieberman (00:48:13):
Basically, the concept of a rolling fund is that it offers investors flexibility to get in and out of funds and not feel so locked in. The whole idea is that, for fund managers, you don’t have to start with large amounts of capital. I can’t remember. The last time I checked, I think Austin’s fund had $2.9 million committed, but I think it’s a great way for people who have large brands and large followings on Twitter to be able to start putting money to work, their money and other people’s money, and do so in a pretty approachable way.

Alex Lieberman (00:48:47):
The other thing is that, normally, fund managers need to raise their entire fund’s capital in a short period of time. The whole idea with a rolling fund is you’re constantly fundraising. So you don’t have to raise a $10-million fund, make, whatever, 50 investments a year and allocate the whole fund within whatever that period of time is. It is rolling in nature.

Alex Lieberman (00:49:07):
And so, as a fund manager, I think it takes pressure off of people where you can start the fund with hundreds of thousands of dollars, not millions of dollars, and continue to raise also as you are proving your worth. Not even proving your worth from ROI and the investments, but even proving your worth of legitimacy in the marketplace and getting involved, getting checks into deals that other big investors are in.

Alex Lieberman (00:49:28):
So I think that’s a big thing, is, one, as a rolling fund manager, you can constantly be adding funds to your business rather than in a single period of time, so it adds flexibility. And to that point, as well, a startup in your company, in your portfolio, has a large markup. So say you invested in their seed or their series A, they raise a series B or series C, as a traditional VC, you couldn’t necessarily use that event as a promotional moment to raise more for your fund, but it’s created the flexibility now that you can do things like that.

Trey Lockerbie (00:50:01):
Yeah. I think it’s amazing. And we’ll link to the angel.co link in the show notes, so everyone can kind of check that out. I think the rolling fund is fascinating, especially for … Obviously, we talk about the public markets a lot on this show, but a lot of gains are there to be made in the private markets, especially pre-IPO-stage companies. And the technology coming into this is really unprecedented.

Trey Lockerbie (00:50:22):
So I want to hear a little bit about how you would approach an investment, now that you’ve been an operator of your own business. What do you look for in the management? What do you look for in the metrics? How has that shaped your investing philosophy?

Alex Lieberman (00:50:37):
Well, there’s a few things. As I think about things, as an investor, as an early investor, one of the things I think about is playing in my circles of competence, this idea of circles of competence. I think Charlie Munger talks about it a decent amount, but knowing what I know, knowing what I don’t know, and then all this massive space of not knowing what I don’t know, I think it’s so important to respect those boundaries. Even as I have started to put my own money to work in the form of checks as an angel, I’ve generally focused on the stuff I know really well. I know media really well, I know community building really well, I know passion audiences really well.

Alex Lieberman (00:51:11):
And so I’ll give you an example, like, one investment I made was into a company called Soul Savvy. Soul Savvy is a paid sneakerhead community. So if you are obsessed with collecting sneakers, you pay $350 a year to be in this community. You’re with thousands of other sneakerheads. You get exclusive looks at new sneaker drops. And my whole view from building an obsessive audience, myself, is that if you play into a deep passion, especially a collectible passion, and you build a good community around that, you’re going to get people locked in for years.

Alex Lieberman (00:51:42):
I’ll use another example. A business I invested in was … There’s this famous Instagram influencer. Her name is Something Navy, Arielle Charnas. She launched a clothing brand. And the reason I was interested in that is, again, she built a passionate audience who cared a lot about following her on Instagram and engaging with her stuff. And a lot of the content she creates is fashion-oriented. So I knew, if she launched a product, it wouldn’t totally change the content of what she was doing. A combination of her having a passionate audience and launching this fashion brand with a proven fashion entrepreneur, who is this guy who has launched several DTC apparel brands, to me, that was really attractive. So the first is playing within my circles of competence because I am not nearly well-versed enough yet, as an investor, to try to make bets outside of the areas that I know really well.

Alex Lieberman (00:52:32):
The second is actually kind of counterintuitive, which is I actually get really scared investing in first-time founders. It’s one of those things where you would expect me to say that, “Oh, yeah, I’m going to be more empathetic and invest in first-time founders,” but from realizing in Austin and my own experience how many blind spots we had, how many mistakes we made in hiring, how many things that we got lucky when we got it wrong that it wasn’t more catastrophic, it actually makes me feel way more conviction, now more than ever, that when I’m putting money into startups or even growth equity stage businesses, that they are proven entrepreneurs because I just think there’s such … from your point that you made, to be a good investor, understanding how businesses are built is fundamental.

Alex Lieberman (00:53:15):
I also just think, to be a good entrepreneur … you know what makes you an even better entrepreneur? Is having been an entrepreneur before. And so it’s this weird thing where it’s like I was a first-time founder. I have so much respect for the people invested in us because there’s so many blind spots we had. And to me, if I can invest in things where those blind spots have been uncovered multiple times, I just think the probabilities are way better.

Trey Lockerbie (00:53:36):
Well, you talk a little bit about what you’ve learned by being a first-time founder on your podcast, Founder’s Journal, which I’ve just found incredibly insightful with your very salient points about just really transparent, honestly, experience that you’ve had. I just feel like sometimes I hear myself talking in your podcast. I can just relate to it so much. So highly recommend that for entrepreneurs to check that out. And you might be a few steps ahead of someone who’s a little bit younger or starting out a little earlier on, but there’s a lot of key takeaways to talk to. What led you to this podcast? Maybe talk about that.

Alex Lieberman (00:54:10):
Yeah. So my whole thing was entrepreneurship has taught me a ton about myself, as a person. And one of the things that I realized about myself is I love being able to reflect on past experiences, past decisions, as a way of learning and also just reliving moments. I’ve also just realized that we, as people, have really faulty memories. If it’s not in photo form or written form, I think memories, as time goes on, tend to take on a life of their own. And what I thought to myself is there’s so much on the internet that allows us to capture memories of our personal life; Instagram, your iPhoto on your phone, all of these things. It allows you to memorialize, create a time capsule for personal moments in your life.

Alex Lieberman (00:54:51):
But when you think about your professional career, which is taking up half of your life, half of your waking hours between the ages of, I don’t know, 20 and 65, it’s actually a lot harder to do that. Where do you go to remember your professional moments? And at first, I was always like, “I really want to keep a journal,” because really successful people journal and it’s really important for clarity of thinking and clarity of writing. And for whatever reason, I couldn’t get myself into the habit of journaling. It just didn’t drive with me. I couldn’t get in the flow of it.

Alex Lieberman (00:55:18):
And so what I said to myself is, “Maybe if I hold myself accountable to journaling to the world, maybe that will get me in the habit.” So now, 178 episodes later, Founder’s Journal has become my journal for the world. And the whole idea is that I document the biggest decisions, challenges, strategies, frameworks, emotions behind the scenes at Morning Brew. And very intentionally, I’ve said that this is for the business builder.

Alex Lieberman (00:55:46):
And the reason I use that language is I don’t think business builders are just founders or just entrepreneurs. People who are working in large companies are also business builders, whether they’re building out a sales org or a new product. And I think they are yearning for the same types of learnings that entrepreneurs are.

Alex Lieberman (00:56:02):
And so basically, it’s this three-day-a-week show, 15 minutes, and I talk about everything from my learnings of being a people pleaser and losing our first two employees and how I had to deal with the emotional reckoning of putting our two early employees leaving on me and something I did wrong all the way to this concept of the Peter Principle, where Peter Principle says that every employee is promoted to the point of incompetence.

Alex Lieberman (00:56:27):
So the idea is that, as employees are promoted, they’re promoted because they do a great job. Every additional promotion, they become less qualified at that job where you could probably find someone elsewhere who is better at, all the way to I saw an executive coach for the first time in the past week and I just documented what that experience was like. And it validated more than ever before, but every professional investor, business builder, it doesn’t matter, probably have someone who serves the purpose of a coach or a therapist. It doesn’t have to be those formal constructs, but having someone to be your intellectual and emotional sparring partner in your career is so important.

Trey Lockerbie (00:57:05):
Well, I loved that one in particular because I recently got my own coach, probably a little over a year ago, and it was after reading the Eric Schmidt book, Trillion Dollar Coach. I don’t know if you know this book, but basically it talks about how all these trillion-dollar companies use, more or less, this one coach and how impactful he really was for their business. So I sought that out for myself and I’ve just seen a tremendous amount of benefit from it. And it also speaks to something that you’ve highlighted about how your personal improvement has directly correlated with the business’ improvement. And I really resonated with that. So maybe talk to us a little bit about that.

Alex Lieberman (00:57:42):
One of my core beliefs, this has been one of my biggest learnings as an entrepreneur, is every entrepreneur, every investor, is generally going to be exceptional at one, maybe two things. Everything else, you are not going to be the best in the world at and that’s okay. And so, for me, I have just learned about myself, that there are a few things that I’m really exceptional at. I am exceptional at storytelling and I am exceptional at creative thinking. Everything else, there is someone better at the job.

Alex Lieberman (00:58:10):
And so I think, honestly, a lot of my personal improvement has been around me getting out of my own way and being okay with not being exceptional at everything. And what I mean by that is, early in the life of the business, I tried to hold onto a lot of things. And this doesn’t mean just with delegation. I wanted to do a lot of the different jobs because I felt, as this competitive, type-A personality, that getting better at the things that I’m weaker at was actually investing in myself and investing in the business.

Alex Lieberman (00:58:39):
I’ve never been more convinced that that was the wrong approach, that the right approach is what are ways you can double, triple, quadruple down on your superpowers and then literally just remove yourself from everything else and outsource everything else to people who are better, outsource through hiring, through freelancer, through people who just love doing those things and it’s their superpowers.

Alex Lieberman (00:58:58):
And so, to this day, when I think about what I spend my time on with the Brew, I always go back to these fundamental questions as a builder, which is what are the things that I am best in class at? It’s literally just those two things. And it’s like, what are the highest leverage things that I can do in the business with my superpowers? And then the third question is, what are the things that the business needs most right now?

Alex Lieberman (00:59:21):
And to me, the way that I have grown, and I think the business has grown, is by always basically landing on the two to three things in the business that the business needs most right now that lean into my superpower of storytelling and creative thinking and are high-leverage activities. And I think it was this turning point where I finally was open to this idea of it’s okay to keep spending time on the things I’m really good at and let the other things go.

Alex Lieberman (00:59:45):
It was a really humbling feeling because it doesn’t feel, at least for me as a competitive person, never felt good to truly have people that were better than me at those things because think we talked about it in concept, that hire really good people around you that are better than you at those things, but when you actually do it in practice, it actually is tough. It’s anxiety provoking. It makes you question your value and if you’re actually good at things. And when I finally got okay with that, or more okay with it, I think it unlocked a ton of opportunity in the business.

Trey Lockerbie (01:00:16):
What would you say is your co-founder, Austin’s, superpower? You mentioned him being somewhat of the, what Warren would call Charlie Bunker, an abominable no man early on. Right? Saying he had a more analytical mind, maybe. What would you say his superpower is? How did it complement yours?

Alex Lieberman (01:00:33):
To me, if I had to say what Austin’s superpowers are, it is strategic thinking and linear thinking. Austin is exceptional at taking a lot of ideas, a ton of noise, and literally just picking out the pieces of gold that are the things we should actually focus on. And especially when you’re a resource-constrained startup, there is nothing more important than having this ability to focus your limited resources. And so Austin is exceptional at setting what our game plan is, based on the little resources we have and all the things we want to do. And then also, once that plan is set, he’s incredible at constructing just these blinders around himself and around the people he works with to only care about those things.

Alex Lieberman (01:01:19):
I think, to your point of the abominable no man, Austin is exactly that way and I think it is so important for a business. I’ve always called it the bomb-sniffing dog of the business, which is the person who has just the naturally critical brain, seems negative in nature because they’re calling out flaws, but I think when you really realize it, they’re actually calling to attention a lot of things proactively that could turn into big issues. They’re able to sniff it out earlier than other people.

Alex Lieberman (01:01:46):
And I think it’s Austin’s ability to understand the strategy of the business, prioritize what we’re doing, and sniff out early cracks that haven’t yet turned into big problems. It is such an important thing to have in a partner.

Trey Lockerbie (01:02:01):
Yeah. I think the distinction there is that you want to have, potentially, a realist to counteract your optimism, but maybe not so much a pessimist. And there’s a fine line, right?

Alex Lieberman (01:02:11):
Yep. I think that’s exactly right. I think it’s this idea of being a realist and putting everything on the table, the good and the bad, but basically just acknowledging what are the things that can hurt you, what are the things that could sink the ship? And if there’s no one to do that, at some point, the ship will sink.

Trey Lockerbie (01:02:29):
Well, luckily, Morning Brew didn’t sink. You sold for $75 million and it’s an incredible accomplishment, especially for someone your age. You have a long, fruitful career ahead of you. I look forward to watching it and following along on Twitter, like I do already, and keeping in touch. And I really enjoyed our conversation. I hope the audience really took this as an exercise as looking into the qualitative measurements of a business, as well as the quantitative measurements. We can all get myopic with the quantitative, but this was such a great exercise, I think, in learning about the qualitative elements of what makes a great business. So thank you for being so sharing with them.

Trey Lockerbie (01:03:07):
So Alex, before I let you go, I just want to make sure I give you the opportunity to hand off to our audience where they can learn about Morning Brew, subscribe to the newsletter, follow along with your podcast, and any other endeavors you’re working on.

Alex Lieberman (01:03:20):
Totally. No, I appreciate that. So if you want to sign up for Morning Brew, the daily newsletter, just go to MorningBrew.com. If you want to follow me on Twitter, I am @BusinessBarista. And if you want to check out the podcast, Founder’s Journal, just go to Apple Podcasts, Spotify. It’s three days a week, 10 to 15 minutes, and I think you’ll enjoy it.

Trey Lockerbie (01:03:40):
Alex, thank you so much for coming on the show.

Alex Lieberman (01:03:42):
Thanks so much for having me.

Trey Lockerbie (01:03:44):
All right, everybody. That’s all we had for you this week. If you haven’t already done so, definitely go to TheInvestorsPodcast.com, check out the wealth of resources we have there for you; different shows, the TIP finance tool, and so much more. And lastly, don’t forget to follow me on Twitter, @TreyLockerbie, reach out and get in touch. And with that, we’ll see you again next week.

Outro (01:04:08):
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