- 6 weeks ago
Morning Brew co-founder Alex Lieberman joins How Success Happens for a fun, fast-paced masterclass in going from side-hustle newsletter to full-blown media brand. Alex shares how he grew Morning Brew from a scrappy startup into a scaled business, the mindset shifts that allowed for greater growth, and the systems that kept the rocket ship steady. He and host Dan Bova dig into how to keep innovating, why expert support at every level is a superpower, and the practical steps you can take to unlock your next chapter of growth. With the business tax filing deadlines are approaching quickly, with many returns due March 16, 2026, understanding what has changed and acting on it with the right guidance may be one of the most practical decisions a solopreneur makes this year. Learn more about filing your taxes with Intuit TurboTax, visit https://turbotax.com/business
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00:00With business tax filing deadlines quickly approaching, many returns due March 16th,
00:052026, understanding what has changed and acting on it with the right guidance may be one of the
00:12most practical decisions a solopreneur makes this year. To learn more about filing your taxes with
00:18Intuit TurboTax, visit turbotax.com slash business. My co-founder Austin and I were completely naive
00:27to media. And I think being naive to an industry is actually an amazing way to just think about an
00:33industry differently because we didn't know what the status quo was. We didn't know how things should
00:37be done. We probably were working on this thing as like a passion project before we were actually
00:41like, okay, this thing could make money. And then, oh, okay, this thing could actually be our livelihood.
00:45And then, okay, this thing could end up like being life-changing for us.
00:54Hey, everyone. Welcome to a special episode of How Success Happens. I'm Dan Bova, writer and editor
00:59at entrepreneur.com. Do you like want to make really cool stuff and do it faster and better and,
01:06you know, make some money while you're at it? Well, today's guest is extremely qualified to advise on
01:12all of these things. Alex Lieberman is a serial entrepreneur, best known as the co-founder of the
01:19Morning Brew newsletter slash Media Empire. And he is the managing partner of 10X, which helps
01:26companies innovate by harnessing the power of AI for good and never evil. Welcome, Alex.
01:33Thanks for having me. Pumped to do this.
01:35Awesome. So let me ask you a question. When a host like me introduces you and lists all that stuff
01:41that
01:41you've done, are you kind of like, yeah, whatever, I did that? Or are you like, hell yeah, I did
01:46that?
01:50I wish I was like, hell yeah, I did that. No, it's, you know, I've done a number of podcasts
01:57and
01:57people have been obviously very generous with the introductions, but I feel like, you know,
02:01I'm still early in my career and I'm still trying to grow every day. I'm 32 years old. And I
02:07also try
02:07to like not take this stuff too seriously. Like I feel very grateful for the life I've had and the
02:12businesses that I've been involved in, but I just feel grateful that I get to play this, like this
02:18internet game and, you know, and get to learn every day and be around smart people. And so, um, yeah,
02:26I'm grateful for it, but I, I try to, uh, I try to also just be realistic and humble about
02:33where I'm
02:33at and where, where I still want to go.
02:35Yeah. So where do you think that, that fire comes from inside you? I mean, you know, you did sell
02:41your, the one business for, for a pretty good sum, uh, you know, some people would be like,
02:48all right, I'm done. Uh, what, what makes you want to keep doing stuff?
02:53Yeah. Look, I think there's different forms of motivation. And I think the thing that motivated
02:58me when I was building morning brew is different than what motivated me as I built 10X, um, with
03:06morning brew, I just, I had a massive chip on my shoulder, like a bag of tortilla chips, just sitting
03:13on my right shoulder at all times. Uh, I, you know, I grew up in the suburbs of New Jersey.
03:19I went to a
03:19small private school and it sucked for me. Like I, I was bullied from fifth grade to 12th grade.
03:27Um, I, I never felt belonging. I never felt community. I didn't feel smart. I didn't feel
03:32attractive. Like I just felt lesser than that's why I always say like life has felt easy since then
03:38because to not feel basically safe every day for whatever it was seven, eight years is crazy. It's
03:47crazy when I think about it in retrospect. And so that's the first part is like, I felt mediocre
03:51and I wanted, I felt this deep desire to prove that I wasn't mediocre. Um, and so that was the
03:59first piece. The second piece is a week before my junior year of college, my dad passed away.
04:05Um, so my dad passed away suddenly from a stroke. He was 46 years old. He was perfectly healthy and
04:11that
04:11just rocked my world. Um, and, and it really like, it was, there's this really interesting duality
04:18in grief where I lost my best friend and it was deeply traumatizing for a 20, 20 or 21 year
04:26old
04:26on the other side. I feel so much gratitude for it because it gave me perspective and allowed me to
04:32make choices that I don't think I would have otherwise made in life. But the thing that motivated
04:37me with morning brew was this chip on my shoulder to one, uh, prove the proverbial haters wrong from
04:43my early life. But also I just had this story in my head that it was my responsibility to take
04:50care
04:50of my family. Now, probably the most fulfilling part of this entire journey of building morning
04:55brew, selling it is being able to give my mom a fat check. Um, and know that she was taken
05:01care of
05:02after all of the efforts she put into me, my dad put into me. Um, and so, yeah, that's what
05:07motivated
05:07me for the brew. And it's just an incredible fire you have under your ass when those are the things
05:12that are motivating you. And that to refine a totally different motivation when I started, uh, 10 X.
05:17Wow. That's amazing. And to all those, uh, I'm just going to say it assholes, uh, suck it. Cause,
05:24uh, wow, that's, well, that's incredible. Um, you know, and, and one of the things, you know,
05:33not having known all of that, that, that behind the scenes story, but one of the things that I love
05:38about the origin story of morning brew is that it's such a great example of something that so
05:45many people on the show have preached, which is that success comes when you make a product that
05:51there's a genuine need or want for it. It's not just cool. Like this is cool. It's like someone
05:56really needs it. Can, can you talk about how that happened? How that unfolded? You know, it's
06:02interesting because I think one of the, the greatest drivers of success for morning brew is
06:10twofold. One is that my co-founder Austin and I were completely naive to media. We had never worked
06:16in media. And I think being naive to an industry is actually an amazing way to just think about an
06:22industry differently because we didn't know what the status quo was. We didn't know how things should
06:26be done. The other piece of it is we didn't think of morning brew as a business for a very
06:31long time.
06:31Like, I think we probably were working on this thing as like a passion project for about a year
06:37to a year and a half before we were actually like, okay, this thing could make money. And then, oh,
06:41okay, this thing could actually be our livelihood. And then, okay, this thing could end up like being
06:46life-changing for us. Right. It, it, it took a long time for that to happen. And so what that
06:51means is
06:51if you're going to start something as a passion project and money is not at all the motivation,
06:56then like one, you have to actually be passionate about it. Otherwise you're not going to work on the
07:01thing. But two, you're going to just be trying to solve a pain point because it's not like you're
07:07trying to make a quick buck with money and just like build something cool that you think you can
07:10sell. It's like, you're likely to be doing something in response to a pain or an issue you
07:15experienced. And the pain or issue that I experienced at Michigan was, I was in my senior
07:21year. I'd already got my job offer to work at Morgan Stanley in trading because my, up to that
07:27point, my entire career, I thought I was going to be a trader on wall street because that's what my
07:32dad did. It's what my mom did. It's what my grandpa did. So I was in my senior year. I
07:36already had my
07:36job in hand, so I didn't need to recruit my senior year at Michigan. And so I had just an
07:41abundance of
07:41free time and basically between taking two classes and then spending the rest of my time playing like
07:46FIFA or NHL on Xbox with my friends. I was like, I was like, dude, you, you gotta, you gotta
07:51start using
07:52your brain a little bit if you want to be ready to go after you graduate. So I started helping
07:57students prepare for job interviews, uh, kids who are re-recruiting senior year. And I would always
08:02ask the same question, which is how do you keep up with the business world? And every single student
08:06had the same exact answer. It was like, they choreographed it together before they were like,
08:10I read the wall street journal, but it's dense. It's dry. My parents told me to do it,
08:15but it feels like unexpiring, unexciting. And I was like, this is crazy, right? Like these kids are
08:23trying to spend their careers working in whatever it is, investment banking, consulting, private equity,
08:28and they feel like they're consuming information that doesn't get them excited about the thing
08:31they think they're going to spend their whole career in. And so that was, that was the pain point
08:35I felt, which is like, how could you feel so shitty about the information source when that is going to
08:40be the fuel for hopefully a career that you feel fulfilled in? Right, right, right. Um, so as you,
08:47as you started to grow and as you illustrated with, and you realized, you know, maybe this could be a
08:53thing. When was the point when you realized like, okay, maybe we can't do everything. Yeah. So
09:00a few thoughts. One is I think any like high agency type a person believes that they need to be
09:09good at
09:09everything when they build a business and when they're an entrepreneur, what I learned in my
09:14first chapter of business. And I've carried this through me to 10 X is like, understand what are
09:20the two or three things that I think I'm best in class at only spend my time on those things.
09:25And
09:25then like delegate everything else out. So examples, like, I think I'm really good at relationship
09:33building for a business and building a network of whether it's customers, partners, I just focused on
09:38the few things that I was great at. And then anything else I delegated. And so it's like
09:44running the day to day of the business, building the business into, uh, you know, an incredible
09:49process driven organization. I knew I was never going to be best in class at that. So that was
09:54something that my co-founder is really good at, or I'll just use another example, like taxes. I
10:00freaking hate taxes. And I think a lot of entrepreneurs like me hate taxes. You know, I wish I had
10:06used
10:06them at the time, but there's this incredible product with TurboTax, um, you know, experts
10:11for business who basically take care of your taxes year round. And it's just like specialists
10:16who actually love thinking about taxes and working on them. And so just, there's this laundry list of
10:21things in business where I don't think I'm world-class. I don't think I love it, but there is someone
10:27if I can find them who is world-class and who does love it. And so I think delegation just
10:31becomes
10:31your best friend as an entrepreneur. I want to follow up a little bit on the, on the idea
10:36part of thing, the ideation. Cause I read another interview with you where you described yourself as
10:41a bucking Bronco who needs to be tamed every once in a while. And I wonder for people with similar
10:49brains, like how do you kind of weaponize that, that you squeeze the good out of that, but don't
10:54have yourself going in a hundred different directions at once. I think one answer is, so,
10:59so this goes back to another lesson I've learned in business, which is, I think there are two
11:04decisions you make as an entrepreneur that are responsible for 95% of your success or failure.
11:11I think the first decision is who you choose to be your partner or co-founder in a business.
11:18The second is what market are you choosing to build your business in? Because what I've realized is
11:2710 X is going to be a multi-billion dollar company. And it is not because I'm a better entrepreneur
11:33now than I was when I was building morning brew. It is just a massive freaking market. And then as
11:40it
11:40relates to me being the bucking Bronco, yeah. Like the thing I always used to say is I was like
11:46a
11:46thoroughbred racehorse who was just like ready to crush the Kentucky Derby, but a thoroughbred that
11:52doesn't have blinders on or a jockey is just going to run off the freaking track. The way I always
11:56viewed it is like there, this is a, an Amazon adage, which is like, there's one way doors and
12:01two way doors in business. Two way doors are decisions you make that are reversible. One way
12:06doors are decisions you make that are irreversible. I just make sure as someone who is like an idea
12:12engine and gets excited by shiny objects and wants to do something new and wants to push the
12:18business even harder. I needed to make sure I was always balanced by the jockey.
12:23I'm curious. So AI is a pretty big topic these days.
12:28Oh really?
12:29Yeah. I don't know. I don't know if you were aware of that, but I was curious, like, you know,
12:34when you talk to, when, when people come to you asking for help, you know, what do you say to
12:40those people who are like, look, I want to innovate. So can you like AI this for me? Like they
12:46don't know
12:47anything. Yeah. Which I think is a lot of us. So
12:54here's how I think about it is I I'll tell the quick story about like how I got into the
13:00space
13:00because I think it'll make people like feel understood because I'm not an engineer. And I
13:07think a lot of people have just assumed like for the indoctrinated, the technically indoctrinated,
13:13like you're set in this post AI world. And for those that are non-technical,
13:17you're kind of screwed. And that is not the case. Um, I, so I would say like, I w I
13:23was always
13:23interested in the technology once like chat GPT three came out. I like, I'd play around with it.
13:30I found myself, you know, slightly more productive. I'd use it to help write emails. I'd use it to
13:35brainstorm content I was creating. I'd use it as a thought partner for decision-making. Like if I had a
13:41big decision, I'd tell it to like, take me through the intellectual gauntlet of what am I not
13:46considering that I should be considering, but I never saw like, I never saw how it could be a 10
13:52Xer
13:52in the way that you hear some people who talk about AI, like it's a, a religious experience.
13:57And so what ended up happening basically is my co-founder for 10 X. Um, he is technical. So he's,
14:04uh, a software engineer by training. He went to Carnegie Mellon. He taught, uh, as an adjunct professor
14:09at Carnegie Mellon. And then he ended up having a few startups and I was catching up with him one
14:14day. And he was basically telling me what happened was he had to pivot his business. And when he
14:19pivoted his business, he had to cut his burn and he had to lay off a bunch of people. So
14:24he had a
14:24nine person engineering team and he had to lay off eight of those engineers. So it was just him and
14:29one engineer left. And he basically was like, I need to figure out how to have as much output
14:35as the nine person team we had, but just me and this one person, because we can't get less
14:41productive, but I can't afford nine people. And so he basically rebuilt his entire product
14:47and engineering process and his output with him and one person measurably was five X more
14:55productive than his nine person team. And so he talked me through how he did that. And that was
15:00like my, like, Oh, like that moment for me. Right. It was like, that was my, wow, this is a
15:08different technology than I've ever experienced moment. Um, and, and so then I just like went head
15:15first into building in this space. What I can say is this technology is not just for technical people
15:22actually more than ever before the technology is getting so good that being technical is less
15:29important than ever before. The other thing about the technology is I always say it's like a fun
15:33house mirror and makes exceptional employees who are great at what they do 10 X better. It makes
15:38mediocre employees like worse because it just creates slop based on their lack of clear thinking.
15:45Shit. That is such bad news for me, but continue.
15:49Uh, no, it's not. We know you're a killer writer. So it's just going to make you a 10 X
15:55writer.
15:55Um, and that, by the way, that's a total sidebar, which is, I think people make this assumption
15:59that AI just creates slop right now. Like that's, that's the, that's the, the prevailing narrative.
16:05That is not the case. Like I can promise you that's not the case, but what is the case is
16:10if you give
16:11bad ideas to an AI system and you don't work with it, like you weren't like an editor works with
16:16their
16:16writer, then yes, it is going to create slop. Like I think people have this assumption that AI is this
16:21crystal key to just do everything. And so they give up on it when they realize it is more work
16:27than they expect. Um, Alex, do you have any opinions about AI or, um, not really zero opinions,
16:34zero opinions, you know, speaking, I have a bone to pick with you. Cause, uh, yeah,
16:39let's hear it about, I don't know when it was 2018, 2019. We had a great editor on our staff
16:44and
16:45she left us to go to the morning brew. Oh no, son of a, so good. Honestly, it, it, it,
16:56it more is a
16:57testament to the quality of a staff that you guys have. Yeah, that's great. That's hilarious.
17:03So, uh, Oh, so we got a, we got a listener question for you. Uh, this is from Lonnie free.
17:09She wrote in and she said, she'd love to know your take on the evolution of the news cycle and
17:15reporting in general over this past decade. I mean, you could probably do it over this past year. Um,
17:21but what are your thoughts on that? This could be an entire podcast conversation itself. I, um,
17:28so here's my thought. I think that
17:33there's actually never been a better time to be in content or media. I don't know if that's a hot
17:39take, but that is my view. And, and here's, here's why I think this beautiful thing happened
17:46with the internet and the platforms that were built on top of it, like X LinkedIn, Substack,
17:52Beehive, et cetera, where the means for creation of content were democratized and access to distribution
17:59was democratized. So back before the internet, right? Like it was the, um, whether it was the
18:05cable companies, whether it was radio stations, whether it was the newspaper companies who had
18:10access to the paper line, the paper routes, like they had monopolies on distribution and creation.
18:16Now that that access exists for everyone. Right. So it's like, you know, Dan Bova can build as big
18:22of an audience as entrepreneur can. And that's like, that is a beautiful thing because my view is,
18:28people have always resonated with people. That's not a new thing, but people couldn't always build
18:33up an audience to a size that people could actually follow them and consume their content.
18:38Now, at the same time you bring an AI. And so that whole first trend I just talked about,
18:45what it basically did is it, it created more supply of content on the internet than ever before.
18:50And the supply of content on the internet really is just a mirror to human capability. And so what that
18:56means is you're going to have exceptional content. You're going to have a bigger group that's good
19:01content and even bigger group that's mediocre content and a really, an even bigger group that is
19:05God awful content. And so like that is, that is not a, that is not a fault of content or,
19:14or the platforms that is, that is the human condition. Now you add an AI and I would say
19:22what I just described gets blown out. Like the, the, the sheer supply is going to be accelerated
19:30in a, in a way that we've never seen before. But what I think that does is it raises the
19:37standard
19:37for how good you have to be to actually earn someone's attention.
19:43Fantastic. How's that for an answer, Lonnie? Love it.
19:46There we go, Lonnie.
19:46Yeah. That's fantastic. So we're going to get, we're going to move into the speed round in one
19:52second, but I did want to just ask one more time, cause you mentioned the importance of your co-founder
19:58and you know, all these tools in the end, they're being used by people. And so what have you talked
20:04a little bit about how you go about aligning with people who are either on your staff or again,
20:10finding these third parties that can do all this work for you that you don't want to do,
20:16or no, you're not good at. Um, can you talk a little bit about bringing that all together?
20:21Yeah. So, I mean, basically the way that I think about it is every,
20:31every entrepreneur has like a stack. They have their stack of like their tools, their people,
20:38and their services that they've come to trust and build their business on top of.
20:44And so this is when I, when I think about like second or third time entrepreneurs,
20:48a lot of their advantage simply is they've gone through the trial and tribulations of making
20:53mistakes with their stack and coming out on the other side with a really refined system of
20:58what are the software tools that they believe in that make their business, uh, easier and run
21:03better. Who are the people that are like the people that they trust most that they're going to bring
21:08with them to any business that they start? Who are the services that do the same? And so for me,
21:13it's like, you know, if I ever hire a writer in my business moving forward, I know the five people
21:21that are getting a text from me, the instant that I opened that, that writer job. If I am looking
21:27to,
21:28I don't know, uh, like do benefits, I have the service that I'm going to for benefits. If I'm going
21:35to, for, uh, taxes and business taxes, right. I'm going to, uh, turbo tax experts for business. Like I have
21:43this stack of all of these services I use and I've gotten to these services because I've made a lot
21:48of
21:48mistakes prior. And so once I have kind of the tried and true stack that I trust, that becomes an
21:53asset
21:54for me because basically what it is, is it's pent up learning and avoidance of future mistakes.
21:59Wonderful. Awesome. Uh, all right, Alex, let's get to the speed round. What do you say? Let's do it.
22:04All right. What is a habit that you are happy to have and one you wish you could ditch?
22:12Habit I am happy to have is I am an avid Lego builder. I build a set of Legos once
22:20a month
22:20and it is my happy place. I'm a very distractible person, but when I build a set of Legos, I
22:25could
22:26literally go for eight hours straight, never checking my phone and not talking to a single
22:29human being. Uh, habit I don't like, you know, we have these like healthier version of Pringles in
22:41our pantry right now. And you would think that I would have the discipline to eat like two of them,
22:46but I pound the entire sleeve. So we basically need to order five sleeve of sleeves of these a
22:51week. So that's a not great habit that I have. Okay. Uh, as long as you're eating the chips and
22:57not the Lego pieces, you know, exactly. Yeah. Yeah. We have, we at least have the right ordering.
23:01Yeah. Uh, and what if, if you are able to do this, what's your favorite way to turn off your
23:07brain?
23:07Is it the Legos or something else that you do to switch things off? Oh, I have so many good
23:12answers
23:13for you. Uh, Legos is one. I love a good pedicure, love a good pedicure. And I just sit there
23:21and I
23:22get callus removal and I just sit and I stare at the ceiling. I say, thank you for giving me
23:28this
23:28moment. I love that. That's awesome. Uh, and then finally, uh, as founder of morning brew,
23:37co-founder of morning brew, how many cups of coffee do you drink a day?
23:42Four. And I would like to be, I don't know why four feels like I'm on the brink of having
23:49a real
23:49issue. So I would say like two to three is my ideal state. I also have my, my, my co
23:54-founder and I
23:55always would have an issue about this. He is a coffee purist. So he put nothing in his coffee.
24:00He drinks his coffee black. I've always been a skim milk guy. And he just looked at me with disgust
24:05every time I would have my coffee. It's like someone with like some McAllens and then they
24:10pour exactly into it. Yeah, exactly. All right, great. Well, do you want to end with, um, some
24:16words of encouragement for people who, uh, have this idea, maybe this newsletter idea or something.
24:23And they just, they just haven't gotten, they haven't put in the, what's the right word I'm
24:28looking for. They haven't started. Get them started. Yeah. Yeah. So what I will say is,
24:36and maybe this is not the advice you want to hear. Entrepreneurship isn't for everyone. And I,
24:41and I am honest about that because I think there are some people that actually being in a nine to
24:46five job leads to a happier, more fulfilling life for them. And to me, what's the end goal here? It's
24:51to live a happy and full life. But for the people that entrepreneurship is for, I've always said it is
24:57the greatest journey and personal growth that is masked as professional growth. And my life has truly
25:03changed because of it. And, and to me, what does it take to be a great entrepreneur? It takes radical
25:09open-mindedness, uh, radical self-awareness, incredible work ethic, and the ability to emotionally
25:19ride the highs and ride the lows in a way that doesn't rattle you too much because that is inevitable
25:25in the game of business. Awesome. I mean, mic drop on that. That's, that's great, dude. Uh,
25:32thank you so much. Thanks for having me. Appreciate you.
25:37Thanks again to Alex and a reminder that business tax filing deadlines are quickly approaching.
25:42Many returns due March 16th, 2026. And so understanding what has changed and acting on it
25:50with the right guidance may be one of the most practical decisions a solopreneur makes this year
25:56to learn more about filing your taxes with Intuit TurboTax, visit TurboTax.com slash business.
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