Morning Brew founder Alex Lieberman

Auren Hoffman (00:01.016)

Hello data nerds. guest today is Alex Lieberman. Alex is the co-founder of morning brew, a newsletter with over 4 million subscribers. Alex founded morning brew in his dorm room and sold a majority stake to business insider for $75 million in 2020. He also co-founded story arb, a content marketing agency, and is the host of the founders journey podcast. Alex, welcome to world of that. I'm very excited now.

Alex (00:25.9)

Thanks for having me, pumped to do this.

Auren Hoffman (00:29.602)

B2C marketing is super dynamic, but in contrast, B2B marketing just doesn't feel like it's changed nearly as much. Why is that?

Alex (00:41.066)

Yeah, it's funny. I always think, I can't remember who said this, but like, I generally believe that people go into B2C to look cool, people go into B2B to make money. Like, I think that B2B marketing is, has generally lagged B2C in kind of every facet for two reasons. I think partially it's a talent issue. I think,

Oftentimes the best, most creative marketing talent goes to consumer companies because there's a natural incentive of if you're a marketer, you want your work to be seen by as many people as humanly possible. Exactly, so I think partially it's dictated by just talent. I think the second part of it is that there...

Auren Hoffman (01:13.997)

Yeah.

Auren Hoffman (01:21.528)

Where you want the Super Bowl ad or something, right? Yeah.

Alex (01:33.824)

B2B is very driven by herd mentality. It's very driven by the need for attribution. that, you know, B2B has always been driven by like demand gen and, you know, even marketing being so intertwined with like your sales org, which that's not how B2C works. And so I think the issue is, is the second that marketing orgs try to do things that are more creative or more top of funnel in B2B.

Auren Hoffman (01:50.392)

Yeah.

Alex (02:03.41)

Attribution gets harder as attribution gets harder because B2B CEOs and CFOs are oriented to thinking about things very simply from like a return on spend perspective. People very quickly put the kibosh on kind of creative efforts in B2B. So I can only count on one hand, the number of B2B companies that I actually think are like pushing the envelope in marketing and are actually like my thing is like

Auren Hoffman (02:21.677)

Yeah.

Alex (02:33.748)

What are B2B companies that are not just impressive for B2B, but actually B2C companies can learn from. And I, if, if that was the proxy, I would say there's like maybe two companies, definitely one that are great at marketing. Everyone else. think it's like meh.

Auren Hoffman (02:50.796)

Yeah. Some of the, lot of B2C companies, founders were marketers at some point in their career. Whereas in B2B, it's pretty rare for the founder to come out of marketing. Mark Benioff might be like the only exception. He ran marketing kind of, and then, and it did that. And, and really like marketing has always been so core for Salesforce from the original, like no sales software thing to Dreamforce to all the other kinds of things. And just cause like,

Alex (03:15.626)

Exactly.

Auren Hoffman (03:19.628)

He's got that DNA kind of built in.

Alex (03:22.452)

And, and, know, just to use an example of a similar, like giant of the industry, which is the example that I was referring to when I said there's like one B2B company that I think B2C companies should actually look to for inspirations. It's HubSpot. Like I think so. So it's funny. Like, I think what everyone thinks about when they think of HubSpot marketing is they think about like the SEO driven blog. And, and what's interesting is like,

Auren Hoffman (03:35.628)

Yeah. yeah. You're incredible.

Auren Hoffman (03:46.158)

Yeah, yep.

Alex (03:51.73)

They were the first to pioneer that. at a point, it actually became associated with the things people don't like about SEO, which is very low as common denominator, 101 type content. But if I look at what HubSpot's doing today from a marketing perspective, it's super smart. They bought the hustle for, I think, $22 million. They basically use that as their anchor property to start up their HubSpot creator network.

Auren Hoffman (04:00.855)

Yeah.

Alex (04:18.636)

And the reason I think it's so smart is because what HubSpot has basically said to itself is like, we are a software business. We are not going to be able to have the world's greatest talent for media and content. So instead, let's just build the infrastructure that supports the best creators and content minds in the world. And that's, let's either partner with them deeply or acquire them. So even last week, they acquired another AI newsletter, but in their podcast network, they have a dozen podcasts.

Auren Hoffman (04:43.916)

Yeah, I saw that.

Alex (04:48.03)

Some of them they own, some of them they just offer the infrastructure to, to be part of the network, you know, the production capabilities, editing capabilities, monetization, et cetera. And I think they're doing it exceptionally well. And I think more and more as marketing gets more expensive, both in B2B and B2C, companies are going to have to make the decision of, do they want to effectively build their own media company and function more like a media company?

or do they want to partner with the best media talent and to partner with the best media talent, you have to offer them something. You have to give talent something that makes it worth saying you're part of this company's network or you're a creator in residence or whatever. And I think that HubSpot is the closest to doing that.

Auren Hoffman (05:32.398)

There are some like VC firms which are essentially B2B businesses that have a great media arm associated with it. If you think of like Andreessen Horowitz, they do a really good job on the media side.

Alex (05:43.016)

I agree, but like they had future right they launched future I think a few years ago which was like their media website and I haven't heard a thing about it in the last year or two and and by the way, I will say like again, you know so much more about venture than me But my general observation has been like in venture you can you you have to have some sort of spiky point of view and your spiky point of view either can be like around a brand

Auren Hoffman (05:50.338)

Yeah, that's a good point. They kind of like, they kind of stop it. Yeah.

Alex (06:11.57)

and like content, it can be around your niche, like as in like, we are the FinTech investor, we are like the frontier tech investor, or like it can be around stage. And I think Andreessen has done probably the best job. I'm trying to think who else, like I think.

Auren Hoffman (06:22.146)

Yeah.

Auren Hoffman (06:28.12)

Well, like Hacker News is kind of like the Y Combinator. Again, maybe they're not putting out the content, but they've created like a media brand there that a lot of people go to.

Alex (06:37.386)

Yeah, I would say actually, I think to that point, YC has been one of the best in creating a content ecosystem. I think First Round has also done a really good job with First Round Review.

Auren Hoffman (06:45.932)

Yep.

Yeah, really interesting. Now, when you're talking to somebody and you're trying to evaluate talent, whether you're trying to hire them or whatever, how do you evaluate if someone's good at marketing? I've always had a real tough time there.

Alex (07:00.02)

Yeah, so here's what I would say is it depends when in like what type of marketer you're looking for, what your needs are, and kind of what stage of business you're at. kind of how I think about it is marketing is this thing that lumps together so many different disciplines from SEO to...

paid search to organic to event marketing to content marketing like there's so much and so I think before you even ask yourself that question you kind of need to understand like are Basically, are you at a place as a company where you know what works and you want to go an inch wide and a mile deep? Yeah, but yeah, basically it's like okay once we knew at morning brew that

Auren Hoffman (07:32.813)

Yeah.

Auren Hoffman (07:46.286)

Right. You're just going to go from one end. Yeah.

Alex (07:55.228)

we were able to get super efficient with paid acquisition to get high quality newsletter subscribers. The marketer that I was looking for was the type of person who I was confident could scale meta and the different programmatic channels. Who could spend $500,000 a month and they have a proven track record of doing so? Before getting to that point,

Auren Hoffman (08:07.564)

Yep.

Auren Hoffman (08:11.438)

So you're looking for someone who's done it before and who's really good, yeah.

Auren Hoffman (08:17.859)

Yeah.

Alex (08:22.036)

Honestly, what I was looking for was someone who was like an entrepreneurially minded generalist marketer who I believed had in could could create enough structure to run tests and see what works but also had enough of kind of like a a flexible mind to be able to test hypothetically five to six different strategies across organic and paid so like our first Person we hired to do marketing at morning brew. They had done growth

at another media company, but they were probably 25 at the time. And honestly, my best proxy for I think they can do it is I believe that they could be a startup founder one day. My view was I think this person can be a startup founder one day and they have a marketing orientation to them. And now this person is a startup founder running another business that they started since leaving the brew.

Auren Hoffman (09:02.968)

Yeah.

Auren Hoffman (09:15.726)

Interesting. Now the influencer marketing is really big already, but there isn't like a, like a brand or a huge company around that yet. Or what is your kind of feeling about where that goes?

Alex (09:27.018)

Yeah.

Alex (09:31.316)

Yeah. So I've kind of had this like dream slash view for a while that what Endeavor, like what William Morris Endeavor has built over the last 30 years, no one's kind of done that in the digital age. Like I look at Endeavor today, Endeavor's a $5 billion publicly traded company that started with their representation business.

Auren Hoffman (09:42.86)

Yeah.

Alex (09:58.634)

their agents were repping influencers at the time, which were actors, producers, directors. And then after they grew up representation, that's when they went into other things like owned IP. So now they own WWE, UFC, PBR. They actually own entertainment technology now and live events. And my whole view is like, no one has kind of built this like three headed monster for the digital age. I think the ones who have gotten closest to it,

Like, I think that Viral Nation is a really big influencer marketing business. They have tens of thousands of consumer influencers that they basically they help brands allocate dollars to. So they run end-to-end influencer marketing campaigns. Exactly. And they do go up into larger scale influencers as well.

Auren Hoffman (10:32.686)

I'm not familiar with them. do they do?

Auren Hoffman (10:46.766)

Okay, so some of these might be small influencers that make, you know, one to 10 grand a month type of thing.

Alex (10:57.022)

I do think one of the difficulties with when you start working with the long tail of influencers and you have say thousands of influencers that you're working with is how do you not degrade the quality of your service? Like to me, like, it's kind of the negative economies of scale that any agency business has. And so I don't think anyone's really cracked that. I think the other big thing is that more and more, I think unlike back in like the nineties with Endeavor,

I think creators have more leverage than ever before. I was talking actually to the president of Viral Nation and he was saying there are 10,000 agents for creators today. So there are 10,000 individual, it can be solo agents or companies. So you think about that and he's just like the switching costs are actually pretty low and

Auren Hoffman (11:43.527)

my gosh.

Yeah, yeah, yep.

Auren Hoffman (11:54.796)

Yeah.

Alex (11:55.636)

And there's so much choice that creators and influencers have. And so I think that's kind of like the new thing that people are going to have to figure out is like, don't think you can be a general influencer marketing business and succeed today. I actually think you have to kind of niche down. And almost similar to the venture business, you kind of need to be known for one thing. So it's like, I think there's a huge opportunity in B2B creator marketing right now. Like more and more B2B companies,

Auren Hoffman (12:20.268)

Yeah. Yep.

Alex (12:23.124)

are realizing that influencer marketing is important. it's funny, they're like five to 10 years late to do this, and they're just starting to get interested in it. To me, there's no go-to household name for B2B creator marketing to help brands do this. I also think this is slightly different, but you've seen a number of creators launch businesses, right? That's become a huge thing. It's like the Mr. Beasts of the world have launched feastables.

I think the only way it works to partner with creators in some way, whether it's to help them with brand deals or to launch businesses with them, is you need to be known as an expert in your thing. And so, for example, like Dwayne the Rock Johnson has Terra Mana Tequila, Conor McGregor has proper Irish whiskey, J.Lo just launched a spirits brand, all three of them were co-founded with Ken Austin, who has become known as like the operator.

for any celeb who wants to launch a spirits brand. And so I think more and more you're going to necessarily need verticalization and the way you grow.

Auren Hoffman (13:26.936)

Yeah, like obviously, let's have them go to you right now and say, because you know a lot about newsletters, but you might not know a lot about burger joints or something. So they should come to you to help you with the newsletter and maybe go somewhere else with the burger joint.

Alex (13:30.846)

Exactly.

Exactly.

Alex (13:38.988)

100 % and and so for me it's like if I was trying to build like kind of the the next-gen endeavor the way I think about doing it is how do I create a create a wedge to help an influencer either work with b2b companies that they don't have access to and I try to build my wedge in b2b influencer or I try to help them launch newsletter and then as we continue to grow relationships with them I bring in potentially a GM who knows a lot about the next vertical that makes the most sense for the roster we're already working with

Auren Hoffman (14:08.686)

What do you think of like community products that are out there where like Sam, Par's community or some of these other kind of community products that are out there?

Alex (14:16.362)

Yeah, you're saying something like Hampton or like a kind of these next gen YPO's.

Auren Hoffman (14:19.298)

Yeah. And maybe you can even build it around an influencer or something like that. Or potentially if there's like a CFO influencer, you could build a CFO community or something.

Alex (14:27.666)

Yeah, yeah. And I think it also creates an interesting question around, you want to like, where, where is there the most value to be created? Is it at like, the software level? Like, do you want to be the plat like a circle, circle or forgetting there's like two or three other businesses that allow you to stand up communities? Or do you want to have the niche communities yourself? Look, I do think there's a huge opportunity specifically again, in b2b to build high dollar price communities.

Auren Hoffman (14:45.88)

Yep.

Alex (14:57.546)

that members put on their company's card because you look at it like the exit, the state of communities for senior marketers, procurement people, senior finance people. It's like these old school trade organizations. And by the way, you're seeing companies start to do this. So obviously you have what Sam is doing, but then you have another business like Workweek. I don't know if you've heard of Workweek, but Workweek is a media business that is exclusively.

working with B2B creators. imagine like the Barstool playbook, but instead of like sports personalities, it's B2B personalities. So like their personalities are like someone who is a CHRO, who all their content is around HR, someone who is like a marketer and all their contracts around marketing. And the way right now they've raised venture money and I think kind of their big play.

Auren Hoffman (15:29.028)

cool.

Alex (15:53.118)

is not actually their media assets. They're starting to launch community products where people join to be members of a CHRO community, et cetera.

Auren Hoffman (16:02.424)

That makes sense. Cause I mean, most of these, like, if you think of like most of these trade organizations are, are horrible. The conferences are just like, they're just mind blowingly boring. Like the content is terrible. Like it's just like, it's just a bad experience all around. most people don't really, they might enjoy like seeing some friends of theirs there and going to the bar and stuff, but it's just like, it's usually just like terrible experience all around.

Alex (16:09.558)

Yep.

Alex (16:24.555)

Yeah.

Auren Hoffman (16:31.422)

And just anyone who's like redesigning that from scratch is going to come up with something like so much better.

Alex (16:36.916)

I also like honestly just playing in spaces where there's like what I call like a combination of like IQ or standard arbitrage. Like I always say one of the reasons I was successful at Morning Brew is I went from working on a trading desk at a bank to working in media. And I think there are smart people in both fields, but the average IQ is lower in media than it is on my trading desk at Morgan Stanley.

Auren Hoffman (17:03.704)

Yeah, and also the number of hours you want to put in as well, right? So you have like a doubling effect there.

Alex (17:06.663)

Exactly.

I think a similar thing, like if you want to win as a marketer and your goal is just to like, be the most successful in kind of like building either, marketing programs or growing a marketing org or building a business that helps companies improve their marketing. To me, it's so much easier in B2B than B2C. Like it is to stand out in B2C. You, you, you actually do probably by nature need to be more skillful because competition is just so much harder.

Auren Hoffman (17:30.338)

Yeah.

Auren Hoffman (17:40.098)

Yeah. And then of course, if you're competing with these like trader relationships, well, they're usually like nonprofits, right? So they can't always attract the most talented people because they can't pay people. They can't give them stock. and so it's, you know, they're, they're, they're only the people that are like real mission driven. Are you really that mission driven? If you're working for.

Like the average trade organization anyway, right? So you're probably, you might, you might be clocking it in. You might not be working as hard. And so if you're competing there, you may have a lot of other opportunities to win.

Alex (18:02.952)

it exactly.

Alex (18:11.37)

And look, I'm mind blown that this stuff still works, but I still talk to B2B marketers who say like their webinars still drive so many leads. Like it's, mind blowing to me, but I, but I would have to believe at some point, like when the kind of the next generation of management turns over, like I would have to think at some point people are going to be like, this is just dog shit and we need something better.

Auren Hoffman (18:19.64)

Totally, yeah. Yeah.

Auren Hoffman (18:36.406)

There is something in B2C where you would never just like completely bore someone in B2C. Like imagine going to like a Taylor Swift concert and being like, this sucks. It's so boring. You're just sitting around and there's no light show and no nothing. You know, but like B2B is just like that. It's like, they just like love boring people.

Alex (18:42.358)

Totally.

Alex (18:50.74)

It's wild. And by the way, that was...

Alex (18:57.016)

This was our whole thesis with Morning Brew when we launched our industry newsletters, right? After our daily newsletter, which was our consumer newsletter, we launched our professional newsletters, which is Retail Brew, Marketing Brew, CFO Brew, HR Brew, et cetera. And the kind of thesis was we think that we can bring the same tone and conversational voice that we did with the daily newsletter to B2Bs. we think, let's just say that the conversational tone

on our daily newsletter is like a seven out of 10. Our whole view was we could have it be a five out of 10 in B2Bs, yet the impact to the reader could be even higher than in the consumer because the bar was so low for people before. And that has been true. And actually, if you were to ask me, like, what is a better business long term? I think B2B media is a fundamentally better business than B2C media because the bar is lower, because people need it to be successful in their job.

Auren Hoffman (19:32.459)

Uh-huh.

Auren Hoffman (19:54.092)

Yeah, so they're pay more for it,

Alex (19:56.34)

And because the average value of a customer is so much higher, know, a CFO brew of a FinTech or like a, an accounting software runs with, they, need to convert one person because their average customer is paying a hundred thousand dollars a year. And so the math is just easier.

Auren Hoffman (20:14.7)

Yeah, that's really interesting. Now your morning is kind like the quintessential millennial brand in a way, right? Do you put a lot of stock in the idea of all these like generational differences?

Alex (20:26.732)

Yeah, mean, 100%. People have been saying for a while, That email's gonna die, people aren't gonna use email anymore. And I don't think that's true, but I will say that I think that younger generations are using email less than I am or you are.

Auren Hoffman (20:47.686)

I freaking love email. think email is the greatest communication mechanism ever invented in history. I love it, but I am somewhat a minority on that one.

Alex (20:52.636)

It is.

Alex (20:57.16)

It's incredible. Yeah, it's incredible. But I think like for the 13 year old, again, I don't know that many 13 year olds, but like, when I've talked to even like my cousin who she's so she's a junior or senior in high school. So she's 17. Like, when I asked her what platforms does she use most email does not come up. It's like, it's YouTube and Snapchat for her.

Auren Hoffman (21:20.086)

Yep. Yeah, it's like getting emails, like getting email from like their teachers or something. Yeah, their assignments.

Alex (21:25.132)

Exactly. And so my whole view is I actually think that I think of the media business as like a hits based business where every product you come out with has a certain shelf life to it. And if you're really successful with a product, the shelf life is like five years. If you're like generationally successful, the shelf life of your media format or product is like 10 to 15 years. Like what I'm talking about, like

Auren Hoffman (21:52.707)

Hmm.

Alex (21:54.058)

Hot Ones or Joe Rogan, they've been around for so long, that is a complete outlier. And I would say for most products, their cycle of relevancy is like one to two years. And so the way I think about how you build a great media business is you basically need the right orientation of talent and the right culture of trying new shit constantly. Because at some point, like for Morning Brew's daily newsletter, at some point, it's going to exit the window of relevancy.

Auren Hoffman (21:58.264)

Yeah.

Alex (22:23.604)

And we're going to need something that is going to be the fast growing follower to pick up growth. And in thinking about what that fast growing follower is, if you were to ask me, what is that in morning Brew's business today? Like it's our YouTube channels and it's our creators that we're working with to create content for the next generation. And to be totally honest with you, like there's a lot of content that like our creators at morning Brew create that absolutely crushes on Instagram or Tik Tok or YouTube.

Auren Hoffman (22:35.949)

Yeah.

Alex (22:52.882)

I watch it I'm like, this is not for me. Like this does not resonate deeply with me. But then you look at the comments and people absolutely love it. And so that is.

Auren Hoffman (22:59.96)

Yeah, like these shorts are really engaging. For some people, they just love those shorts. They just like watch them while they're in the bathroom or something like that.

Alex (23:06.622)

Yeah. And so I do think that's a, that is a big shift that founders have to go through in various ways, which is when you all of a sudden are no longer your core consumer, right? Cause like when we created morning brew in the early days, like I was our reader, so I could make recommendations and be like, this is what I want. And I believe if we extrapolate me, the rest of our audience will want that. That doesn't work for a lot of our content anymore.

Auren Hoffman (23:17.794)

Yeah.

Auren Hoffman (23:31.438)

So I mean, you can make an argument then that like, you should be playing to your core competency and focusing on the folks you know most and stuff, which is why like your B2B might be a better play now, whereas when you're 22, B2B might not have been such a good play.

Alex (23:41.27)

So.

Alex (23:47.564)

100 % now the risky part about that is like, know, it's why when I talked to the Wall Street Journal as we were building morning brew People would tell me like what you guys are doing makes so much sense We should buy you but we're not going to because we're focused on the 60 year old who's paying our bills right now and it's but at some point that 60 year old is not gonna be paying our bills anymore and we are gonna be wishing that we were focused on the 22 year old

Auren Hoffman (24:05.902)

Correct.

Auren Hoffman (24:12.846)

That's right. Yeah. Now, if you went back five years, like what other advice would you give yourself in kind of the morning brew days?

Alex (24:21.866)

Yeah.

I think there are, so there's a few things. The first is that I think, so this is going back like, I'll go back four years. I believe like our bodies, like our hearts and our intuition very often leads our brains. And so I think there was a period of a year where I knew that my energy and my heart was not in morning brew anymore.

Auren Hoffman (24:53.783)

Hmm

Alex (24:54.282)

And I think it took me a year to a year and a half to drop my ego and allow my mind to catch up to it. And for me, the reason for that was is like, I am very much an early stage builder. I love the zero to one of companies. I love when building a business feels like art and artisanship. The point at which the brew felt less like artisanship and it was, had 50 people and it was about org building.

Auren Hoffman (25:21.206)

Yeah. You have skips.

Alex (25:21.514)

you know, and implementing OKRs or EOS and all these things, like, it just, it felt less fun to me. And I think it took a year for me to accept that and kind of realize that it's okay to not love building your company for 20 years straight. And I think for me, a big reason that I kind of had this ego around it is like, I admired these

career long entrepreneurs who took their thing for, yeah, yeah, like, yeah, those were always the examples that were talked about publicly, Zuck or, you know, Evan Spiegel or Elon, all these people who took it from ideation to public and right, exactly. And so I kind of had set the standard for myself, like, of course I both have to love every part of the journey and I have to be exceptional at every part of the journey. And I think entrepreneurs need to feel more permission and actually encourage.

Auren Hoffman (25:51.916)

Mark Zuckerberg or something, yeah.

Yeah.

Auren Hoffman (26:03.554)

Yeah, Jed's vlog, like all these folks, yeah.

Alex (26:19.052)

to admit to themselves when they no longer getting the same energy. Because the second that happens, I think the odds of their business succeeding goes down. And the best thing they could possibly do is to find the right person who gets the energy that they had in the previous five years.

Auren Hoffman (26:33.954)

Finding that person is really hard, like, and it's very, very risky.

Alex (26:38.252)

100 % and by the way, that's why I feel so grateful like I think you know, we talk about luck in business all the time the luckiest choice that I made was picking my co-founder because I had good intuition to pick someone who was Very smart had similar values to me and I felt like he had a totally different brain from mine That was this I guess like 10 % of the skill, but what I did not at all. No was that like

Auren Hoffman (26:49.72)

Yeah.

Alex (27:05.728)

when I handed the baton to Austin, my co-founder, he felt kind of like most in his zone of genius in the org building stage of the company. And what...

Auren Hoffman (27:16.782)

yeah. Plus he's still our founder. She still has the credibility to make the horror changes and do things that are unpopular.

Alex (27:21.119)

Exactly.

Alex (27:26.056)

Exactly, and I do believe a lot of times the best stage two CEO for a startup is someone who is a stage one COO because I think the skills of a stage two CEO look a lot like a stage one COO

Auren Hoffman (27:36.504)

Yeah.

Auren Hoffman (27:40.526)

Though sometimes it can backfire. I mean, I'm not sure, I'm not sure. Steve Ballmer, I think did an okay job, like they were, Microsoft's going through a very tough time in the early 2000s, but you know, it's probably better. It probably would have been better to get like a more product oriented CEO, then pick the number two or, know, it's always like, if, if, if you think of like Zuckerberg and Sheryl Sandberg, like if he left, like,

Alex (28:04.865)

Yeah.

Auren Hoffman (28:08.519)

She probably could run Facebook fine, but she would have been maybe better running Goldman Sachs or Citibank or something like that, right?

Alex (28:13.9)

I totally agree with you. Yeah, like I think to your point, it is the riskiest decision you can make and that's why I feel very grateful I had Austin and it's why, you know, for some people being a solo founder works just fine. For me, for a variety of reasons, having a great co-founder is like really valuable to me, not even just like the accountability and like the partnership.

but also in some ways to know that you have another possible option before having to go look externally.

Auren Hoffman (28:44.834)

Now, lot of founders go through this like post exit malaise where they're going through like, what should I do next? what can I, should I top the thing that I'm doing or, you know, or like, do I put all my chips, you know, Elon Musk kind of put all of his chips back on, you know, how do you think about it?

Alex (28:55.84)

Yeah.

Alex (29:02.708)

Yeah, well, I think there's a few things. So I guess I'll set the context on this. I'll first start by saying is I have absolutely experienced kind of post exit blues and I've experienced it in different phases. Like I experienced it a lot right after stepping out of the CEO rollout Morning Brew in April of 2021, where I went from working 70 hours a week on Morning Brew.

to zero hours a week and all of a sudden I had an empty calendar and I was like, what do I do my whole day? I would say I'm go, I, a period of time I was occupied and let's call it distracted. And then now I'm, can, yeah, yeah, exactly. Yeah, exactly. I went into making a bunch of angel investments. Then I stood up a new business, which was StoryArb that I was very involved in for like 12 months, but then my CEO and co-founder took it over and I'm back in this place where like I've.

Auren Hoffman (29:29.87)

He

Auren Hoffman (29:41.336)

making all these angel investments or doing all these random things.

Alex (29:56.3)

nine hours a day of free time. I'm like, what the hell do I do other than go on podcasts and tweet? And so I, here's the context I'll share. The first thing is that I do think a big thing that shapes kind of like my energy and how I spend my time is the fact that I lost my dad in college. He was 47 years old. I was 20. He was perfectly healthy and

One day he was alive, one day he wasn't. And I think everyone talks about the fragility of time, but unfortunately, I believe there's some lessons in life that you just feel more when you experience them. And so I give that context because something I know I can't do is even if there's a huge business opportunity,

Like, let's just say I went through the exercise of like spending a month finding what is the biggest possible growing market? What's a massive problem? What's something that I could believe could be a hundred billion dollar business? I couldn't, even if I felt like I was equipped to do it, I couldn't just go build that thing for the goal of like building a hundred billion dollar business. Like that would not be able to keep my energy, like keep the light burning. I need to feel

some sort of intrinsic drive in a way that I never did. I would say the other thing is, and you know, we've spoken about this before, is like, I feel very grateful for having an outcome from the brew where I have financial freedom. And I always find it interesting, which is like people say like, financial freedom gives people the freedom to choose how they spend their time or the freedom of time.

Auren Hoffman (31:44.408)

Yeah.

Alex (31:44.64)

And I think it's like a misnomer. What you want is not like endless time. You want the ability to spend your time exactly what you want it. Cause I can promise to anyone listening 12 hours a day of not knowing what you want to do. I wouldn't wish that on my worst enemy. You want the ability to spend your time exactly as you want to. And so I think, you know, I can just talk to about my experience, which is like, left, you know, coming out of the brew.

Auren Hoffman (31:59.067)

Hehehehehe

Alex (32:11.912)

I felt less motivation towards things. I felt less identity, like I felt less of a sense of purpose. And so kind of where I stand today is I would actually say like, I have a clearer sense of my identity. Like my identity, my identity was entirely pent up in morning brew. Today, I feel like my identity really is balanced across like work stuff, my fa-

Auren Hoffman (32:35.21)

You got married around that time, didn't you? think or...

Alex (32:38.016)

Yeah, I got married just over a year ago, yeah. Exactly, but I would say around the motivation and purpose piece, I still am honestly kind of lost on that because my general strategy right now is I'm tinkering with a lot of things.

Auren Hoffman (32:40.726)

Okay, yeah. So you're probably already in that process when you're sold it and everything, right?

Alex (33:01.684)

I'm like tinkering with projects and my general thesis is at some point, if I create enough like thoughtful surface area, one or two things is going to really speak to me and I wanna dive in. But there's always like the little birdie in the back of my head that's like, Alex, you need to build something bigger than the brew. Alex, you need to have a huge impact on society. And I think what's hard about that is,

Auren Hoffman (33:21.837)

Right, right.

You don't want to be like 20 years later, like you're cleaning the fame as ex morning blue founder necessarily, right? Or maybe that's okay.

Alex (33:31.95)

Well, I think kind of the way you even just spoke through that is like what I'm trying to figure out. Like, am I okay with this idea that morning brew could potentially be my biggest claim to fame ever professionally? Like, would I be okay with that? If personally in my family life, like that's where my next claim to fame is and I crush it as a father, as a husband, as all of these things. But I think what's also hard for me is after you've built a business,

Auren Hoffman (33:36.919)

Yeah.

Alex (33:58.666)

you know how freaking hard it is. And it's like the right it's like the famous Jensen Huang interview quote now or the acquired guys asked him like, would you do it again? Would you build Nvidia again knowing what you know now and he says no, and he's like, no.

Auren Hoffman (34:00.67)

Loli.

Auren Hoffman (34:12.638)

There is some amnesia. like when women have kids, they forget how hard giving birth is. That's the only reason you would do it again because there is the amnesia part of it.

Alex (34:23.712)

Totally. And what I would also say is like even now is like I'm starting up when I'm starting up a new business and like I'm on sales calls after three sales calls. I'm like this frickin sucks. Like I could not spend even like a week doing this. Whereas in the early days of morning brew, I was on sales calls with advertisers for 10 hours a day for months straight. And so I think almost like I find my threshold for like sucky work.

Auren Hoffman (34:35.0)

Totally.

Alex (34:51.444)

is so much lower or like my tolerance is so much lower. But if you're gonna build...

Auren Hoffman (34:54.808)

Right, that's tough because you need to do sucky work to build something great. Yeah.

Alex (34:58.066)

you have to if you're gonna if you're gonna build something great you have to and so I think yeah, I'm honestly like I'm I'm in the market for trying to figure out what it is while also knowing that like it's I'm not gonna have likely this like epiphany of like, know, I'm not gonna have this like Vision one day of I'm build this massive company. That's gonna save the world. And so yeah, I think it's so interesting because

Ever I I've talked to now maybe 50 plus post exit founders that have experienced some permutation of what I'm describing. And when they talk about kind of finding their purpose after it, a lot of them will say it's like still a work in progress. Or a lot of them will say it's like, I didn't have this like, you know, this come to Jesus moment. I just like was like tinkering around with things. Something really like felt right to me. And I've just decided to spend time on it.

And all I know is what I don't want my answer to be is to go build three more companies because that's what I'm supposed to do. That is what I know I don't want to do.

Auren Hoffman (36:03.724)

Yeah. Now, going back to you mentioned your dad's passing when you're 20, like I imagine that had just like a massive effect on just like how you thought about life, how you think about what you want to do in your career. Like, can you walk us through some of that?

Alex (36:09.035)

Yeah.

Alex (36:17.566)

It is. Yeah, I mean, look, I think the...

Alex (36:28.096)

The sadness, the most sadness that I hold towards my dad's death is actually not being able to be with him today. Obviously I have sadness towards that. It's actually, it's sadness for him because my dad was someone who he worked his ass off to get to where he was. He worked in finance, but he didn't go to an Ivy League school, so he didn't have this like,

you know, kind of like very clear path of going through a rotational program and like kind of having the next 20 years. He chart, he started as like a bank teller in a branch at a bank. And he made his way up to like running multiple trading desks at Citigroup by the end of his career. And he worked his ass off to do that. And I think my sadness I feel is that he didn't get to truly see all the fruits of his labor.

both for himself personally and also the time he put into his kids. Like I feel so much gratitude towards this guy would wake up at 5 a.m. every day, get back from work at 7.30. He, you know, I'm sure he was exhausted and wanted to do anything other than helping my sister and I with our school stuff, yet he would spend the next three hours helping us with our school stuff for like decades. And so, you know, when I reflect on...

That's thing is like when I reflect on why my dad was such a great man, of course it was like how he was able to get to such a great spot professionally without starting on third base. But it was the amount of effort and true care he put into kind of giving my sister and I the foundation that got me to where I am today and got my sister to where she is today. And so I think that...

That's all, and you know, you and I have spoken about this previously, but like for me a big thing is I wanna figure out like how, when I ultimately figure out some of my professional purpose, how can I do that exceptionally well, but how can I also crush my personal and family purpose? Like when I do ultimately have a family, how can I, how can I be like, I wanna be an A dad, I wanna be an A dad and.

Alex (38:47.7)

Is it possible to be an ADAD and an A builder of anything professionally? And I think we've talked about it. It's like.

Auren Hoffman (38:53.326)

And you don't have kids yet. you have a thought in your head? want to have one kid, six kids, 20 kids.

Alex (39:00.492)

In my perfect world, it's like three kids living in the suburbs of New Jersey, maybe a ski home in Colorado, go on one to two nice family vacations a year and that's it. Like that is happiness to me. totally. And so I think that's the thing is like.

Auren Hoffman (39:09.806)

You

Auren Hoffman (39:17.582)

That's happiness, yeah. I mean, that would be happiness to most people.

Alex (39:28.694)

How, I think the big question in my head is like, when money is no longer really an object, how do you find the thing that acts as strong of a motivator as when that was the primary motivator? Because I've talked about this with my buddy Jesse Poojee, who's an entrepreneur a lot, which is like there's.

Auren Hoffman (39:48.416)

Also a password of DasGuest.

Alex (39:51.732)

Yeah, exactly. We've talked about this a lot because him and I both are big believers in conscious leadership group and the 15 commitments of conscious leadership. And there's a few different, there's fear-based motivation and growth-based motivation. And I think in building Morning Brew, a lot of my motivation was fear-based motivation, which was a fear of not having enough money, a fear of not being accepted by people, a fear of not belonging. And those things were such strong motivators.

Auren Hoffman (40:20.47)

Yeah, yeah, especially when you're young. Yeah.

Alex (40:21.558)

Those things, exactly, exactly. And those are not that strong of motivators anymore. Like, I still care about money. Don't get me wrong. Like, I don't think I could just go start a nonprofit today and feel fully settled. I don't believe that. But I know those can't be the only motivators. And so what I'm trying to figure out is how can I find the thing that lights me up in the same way that I was lit up by my old form of motivation in the first five years of morning brew?

Auren Hoffman (40:47.116)

And you think like your father's passing made you also want to prove something like so many well-known entrepreneurs have had, I mean, many of them had issues with their fathers. If know, Elon Musk, a lot of them have had absent fathers who didn't even know their fathers, Steve jobs, Jeff Bezos, Larry Ellison, you know, et cetera. Some of them have had, you know, early fathers passing away, et cetera. Like, do you think some of that

Alex (40:58.625)

Yep.

Alex (41:10.942)

Yeah, I think, yeah.

Auren Hoffman (41:14.06)

help, know, it's helped obviously wouldn't have wished it, but helped your motivation.

Alex (41:18.132)

Yeah, so I think there's two things. One is like adjacent to my dad's passing, which was that, you my mom had worked on Wall Street for 20 years, but she had retired prior to my dad's passing. And so after my dad passed away, there was no breadwinner in the Lieberman family anymore. And so I very much had this fear of like, I literally, I'm a very visual person. And so I had this visual constantly of like a pile of money.

Auren Hoffman (41:38.403)

Yeah.

Alex (41:47.53)

with the name Lieberman on it and every day, yeah, exactly, just slowly going down and like a little vacuum cleaner sucking it up little by little. And so I think in my head, was, yeah, exactly, exactly. call it like, say, my mom lives to 90, right? Like that's many years of not having income and also having to pay for her kids. And so I think that was a huge thing in my head was I know,

Auren Hoffman (41:48.878)

Just like slowly going down. Yeah. Right, because you said it was 47, so your mom's young at the time. Yeah.

Auren Hoffman (42:07.404)

Right, half our life. Yeah. Yeah.

Alex (42:16.502)

baseline, no longer wanted my family to have to pay for anything for me. And also, of like what I promised to my dad, like when my dad was in the hospital and we knew that he wasn't gonna make it anymore, like I whispered to him saying that I was gonna take care of my family. And I literally like in that moment pictured handing checks to my sister, to my mom. And what's interesting is like,

I did not grow up really knowing my family's exact financial situation, right? Like I knew roughly socioeconomically where we stood. Like I think we're, you know, we're upper middle class. Exactly, yeah, exactly. So I didn't know my parents' balance sheet. And so I didn't know to what extent it was actually a rational or irrational thought to want to like take care of my family. But that was one thing that like I promised my dad. And so that became something that drove me forward.

Auren Hoffman (42:53.048)

Yep. Yeah. Usually you're not sharing. Usually your balance sheet with your kids or something. Yeah.

Alex (43:13.686)

The other thing is I was bullied a lot growing up from fourth grade to 12th grade. I was bullied. And that's why like honestly everything in my life has felt like a cakewalk since then. Because imagine for like nine years, nine straight years of life, not feeling like you're belonging at school every day and feeling like people are picking on you and feeling you're... Yeah.

Auren Hoffman (43:28.824)

Ha

Auren Hoffman (43:38.146)

But by the way, that's so common for most entrepreneurs, right? Because like part of reason you become an entrepreneur is because you kind of feel like you're not really fitting in and stuff like that. Otherwise you would just like stay in that job and finance that you had or something, right?

Alex (43:46.441)

Exactly.

Alex (43:50.88)

Exactly, and so I think a big part of my motivation also was just proving all these people wrong that I felt inferior to for nine years straight. And so that's the thing, right, is how do you go from like this incredibly powerful form of motivation, but that isn't necessarily, can it necessarily be like a long-term burn? Once that form of motivation is gone, where do you conjure up?

that similar fire in your belly? Or is it not possible and the motivation has to look different? Is it like kind of the difference of like kind of lust and like passionate love in the beginning of a relationship versus a slow burning love? Like it's an interesting thing to think about how motivation shifts.

Auren Hoffman (44:32.45)

You've got a podcast called Impostors where kind of you guys, you and your guests talk about like mental health challenges and stuff. Like what are some of these through lines that you've noticed?

Alex (44:44.889)

So I think the best description I've heard of imposter syndrome was by Jay Shetty, who's a friend and he was on the podcast. He has a great podcast called On Purpose. And he basically said that imposter syndrome is the result of your current skills. It's a gap in your current skills and

your ultimate goals and it's just your goals sit above your current skills today. And he's like, when you think about it like that, of course you like, not only is imposter syndrome something that many people have, but it actually should be the goal. Because if you don't have your current skillset being lower than the goals you want to achieve for your business, how are you going to grow? Like how are you going to be ambitious? And

Auren Hoffman (45:31.395)

Yeah.

Auren Hoffman (45:37.006)

So lot of people overestimate their current skills, right? So then you would think like, okay, if you're overestimating, you would have last imposter syndrome or something.

Alex (45:44.844)

Yeah, that is, it is interesting. I would say that, so it's funny, like, but if you were to ask me who I would bet on, it's generally the person that doesn't overestimate their skills. It's the person who underestimates their skills, but they don't let that get in the way of them continuing to push forward. Look, I think that imposter syndrome is not only so common, but I also think it is so shaped by people's

Auren Hoffman (45:58.562)

Yeah.

Alex (46:13.396)

early life experiences. Like I think the reason that like I experienced imposter syndrome and other people on the show did is because they had some experiences earlier in life that made them feel like that they were lesser than and they were not capable. Like I actually think that imposter, my kind of hot take is imposter syndrome happens more frequently to people who had challenges with self confidence early in life.

and they still feel the residue of that today in certain contexts.

Auren Hoffman (46:46.368)

Interesting. Okay. Yeah. Right. Cause I mean, they're definitely friends of mine, think of who kind of who been very successful have had imposter syndrome, but there's also a lot of successful friends of mine who've never had it. They've always felt that confidence. you know, like I, I, know, I don't think like Elon Musk feels imposter syndrome. You may have a lot of other mental health challenges, but like, he's always confident in himself and that he can do something. So everyone is, there's some sort of like continuum of people.

Alex (46:56.044)

100%.

Alex (47:11.478)

I also-

I also think imposter syndrome is, it's not like a, it's not a, it's like not a global feeling that people have. I think it's like our life is full of specific verticals of experiences that we have more or less competencies in and based on the vertical that you're focused on, you may or may not have imposter syndrome. And so it's like when it came to like me doing sales calls or anything related to selling or storytelling at Morning Brew.

I never felt imposter syndrome. I actually felt like irrational confidence. But when it came to like me thinking about like, I doing a good job as the CEO of the business? I felt wild imposter syndrome. know, Elon Musk probably when it relates to like solving really hard engineering problems does not feel imposter syndrome. But maybe as it relates to like dating, he feels a ton of imposter syndrome. So I also think imposter syndrome is not a global thing. It's a vertical specific thing.

Auren Hoffman (48:13.166)

Okay, yeah, that makes a lot of sense. You're kind of a creator of businesses. What is like your weirdest or what is a weird business idea that you think would work?

Alex (48:20.235)

Yep.

Alex (48:25.164)

that is a good question. Let me go to, have, so I keep a list of all of my business ideas, on my phone as most people do. Like, yeah, as, as, as in, okay. So have you ever heard of, let me just make sure I'm getting the name right. This is, I mean, this is a ridiculous one, but you want a ridiculous, have you ever heard of gra, granimals? Okay. So granimals are.

Auren Hoffman (48:34.222)

Of course you do. Yeah, I do as well. That's like a thing. Yeah.

Auren Hoffman (48:50.541)

Duh.

Alex (48:54.768)

mix and match clothing for babies and toddlers. So, that's so funny. I was just looking up Granimals. They're actually owned, no, I originally thought they were owned by Berkshire Hathaway and I was like, that would be really weird. So Granimals, basically what it is, is if you shop for their stuff, it's like you can buy articles of clothing, tops and bottoms, that are made to go together. And so you basically can buy five tops and five bottoms.

and they make certain combinations that all work together. So you don't have to, as a parent, think about what's gonna match with what. You have like sets of clothing.

Auren Hoffman (49:29.27)

Okay, right, right, that makes perfect sense, yeah.

Alex (49:33.096)

Exactly. I believe that can exist for adults. I think as adults, you know, oftentimes we want to look good, but we don't want to spend so much time thinking about what we're wearing. It's like the old, like why Steve Jobs wears turtleneck and jeans all the time. And I guess pre Zuckerberg being cool and having swag, why he would wear his sweatshirt all the time. I think

Auren Hoffman (49:47.779)

Yeah.

Auren Hoffman (49:55.436)

Yeah, just who are wearing like like the all black with the leather jacket.

Alex (50:00.606)

Exactly. I believe there can be basically like a pretty like elevated version of geranimals for adults where it's like nice clothing for men and women, but basically it just there's a there's a system of a number system that if you buy a one on bottom, you know goes with a one on top and so that

Auren Hoffman (50:19.352)

But like what doesn't go with jeans? if you're just going to wear jeans, like what would what would not go with jeans or something? mean, you know, it's like this isn't everything go with jeans.

Alex (50:25.356)

I think for two people that maybe aren't in high fashion, probably everything goes with jeans. My guess if I was to ask a fashion influencer, they would be like, that is such a faux pie. You're not thinking about layering at all. I know a big thing in fashion is layering. You wear a t-shirt and then you wear a button down with it. So I think that's one is basically granimals for adults.

Auren Hoffman (50:35.159)

Yeah.

Auren Hoffman (50:40.18)

yeah there might be like certain shoes or something but I feel like yeah.

Auren Hoffman (50:50.132)

okay. didn't know that. Okay.

Alex (50:55.884)

Here I'll give you a few others one is I am surprised that there is not a A plate basically there is no like Yelp for Travel itineraries meaning there is no place that if you want to travel to a place that you can go and basically find people's itineraries that have been created of all of the places they went rest

Auren Hoffman (50:57.772)

Yeah.

Auren Hoffman (51:23.68)

yeah, that would be so awesome. Yeah. Yeah.

Alex (51:25.195)

Right? It's like kind of crazy to me. and people can have their itineraries rated. People can make money off their itinerary by getting paid, affiliate by the things they list on their itineraries. You can be a power creator. And so like to me, the fact that doesn't exist, I would have to think someone's truck.

Auren Hoffman (51:35.2)

Yeah, yeah.

Auren Hoffman (51:41.27)

My wife spent so much time. It's like her kind of like she's so good at it and she'll do it at like 2 a.m. and stuff. Right. But she like spent so much time finding that perfect guide or something.

Alex (51:46.378)

Yeah, and think about how much like...

Yeah, and imagine...

Exactly, and travel is such a custom experience and personal experience that potentially like me asking one of my friends for a Greece itinerary may not make sense either from a budget perspective or like say my wife and I are more into adventure and not just sitting at a pool all day and so you could filter for all of these things on this website. Exactly. Exactly. So I don't know why that doesn't exist because I would use it every day.

Auren Hoffman (51:59.33)

Yeah.

Auren Hoffman (52:13.23)

Of course, you're like, don't like golf. that just, that gets rid of all these things, right?

Auren Hoffman (52:20.43)

I love that. That's great. Any others while you're on a roll?

Alex (52:23.626)

Yeah, yeah. So.

I have a few ridiculous ones. Okay, so one is a So this is a fun story the thing that got me into Media is actually ironically I Became like the director of a publication at Michigan's campus and it was complete It was totally like a resume booster for me Like I wasn't thinking about it actually being like an important formative experience for me But it ended up being like the only relevant experience to me building a media company after college

Auren Hoffman (52:57.048)

Hehehe

Alex (52:58.144)

And what the publication was, it was called Consider, and it was a two-page magazine print publication that would do a point and a counterpoint on a hot button issue. So it would be like abortion, and you would have someone who is pro-life and pro-choice super well-educated on the topic, and it basically be a written debate for arguing each side. I just, I would love to bring Consider to like everyone. Like, what if there was just a

Auren Hoffman (53:19.628)

Yeah.

Alex (53:27.756)

Print publication, it also doesn't have to be print. I just think print at a time where everything is digital, there's something special about it, of the most hot button topics in society that to be a educated citizen of the world you should know about with really well-educated point and counterpoints on these issues.

Auren Hoffman (53:33.048)

Yeah.

Auren Hoffman (53:44.94)

Yeah, that's good. I love it. All right. asked two more. We asked two questions to everybody before they leave. One is what is a conspiracy theory that you believe?

Alex (53:46.913)

Alex (53:50.581)

Yep.

Alex (53:56.906)

Okay, so there's two that I was thinking about.

Alex (54:02.829)

One was about the government putting fluoride in our water. And the second was...

Auren Hoffman (54:09.506)

I've heard about this, tell me about the fluoride thing and a few other people have told me about this thing.

Alex (54:14.54)

Yeah, so my understanding of the fluoride thing is that the government puts fluoride in the water. So it was a 1950s conspiracy. And basically the claim was that fluoridization was a communist plot to undermine American public health. And that basically it would...

Auren Hoffman (54:25.228)

Yeah, tap water, they have fluoride.

Alex (54:41.834)

It would be used as a way to hurt health of Americans so that Americans would need to receive more health and it would boost our health care system. That was one of the conspiracies.

Auren Hoffman (54:52.334)

It's interesting because my dentist told me I should stop drinking bottled water and drink tap water. He's like, so much better for you. It's like just drink the tap water.

Alex (55:00.298)

I feel like this is like a very hot thing right now because that's what I always understood is like fluorid in water was good for your teeth. I think there are recent studies that have come out saying that fluoride is like poison for you as a human. So yeah, I would look at the recent studies around that.

Auren Hoffman (55:02.669)

Yeah.

Auren Hoffman (55:11.444)

okay. interesting. Okay. So I'm sure most toothpaste not gonna be brushing my teeth anymore.

Alex (55:18.132)

Yeah, the other one like I don't know if this is a conspiracy. I don't know. Like it's just the whole alien argument around like aliens on earth and like are we in the presence of aliens? If that was a conspiracy, I don't know what that's considered, but I am fully subscribed to the idea that we are on earth with aliens today.

Auren Hoffman (55:28.162)

Yep.

Auren Hoffman (55:39.262)

So you think like there's another life form that's super intelligent that is interacting with us in some sort of way, but we they're making sure we don't see it or something or.

Alex (55:51.372)

I think the most likely scenario is that

the alien life has experienced our planet and had the observation that we are so dumb and so kind of like single-minded relative to their capabilities that it would be as if like I saw an ant on the floor of my apartment and I kind of explored deep conversations with that ant a little bit further. So that's my belief. It's just we're a waste of time for smarter forms of life.

Auren Hoffman (56:16.226)

Yeah.

Auren Hoffman (56:20.064)

Yeah, yeah, yeah, yeah, that's interesting.

Auren Hoffman (56:27.886)

Okay. I like it. All right. Last question. I have so many conspiracy theories. Yeah. just so many conspiracy. my gosh. could, I, could do like, we could do like 10 podcasts and all my crazy conspiracy theories. last question. asked all of our guests, what conventional wisdom or advice do you think is generally bad advice?

Alex (56:29.878)

Do you have one by the way?

Okay, we'll have to spend a whole nother podcast on that.

Love it.

Alex (56:53.28)

This is gonna be a very timely one, which is a lot of people talk about, so I think follow your passion is one that's been like, I think debunked a lot. I'm gonna talk more specifically around like follow your energy. Like people say like, you know, as you're thinking about the next business you wanna build, like figure out what gives you energy. Like people always talk about like look at your calendar from the previous week and.

Auren Hoffman (57:05.367)

Yeah.

Auren Hoffman (57:20.181)

right, right.

Alex (57:21.14)

And color coat the things that were like energy positive versus energy negative and spend more. And I think it's a load of bullshit because, because I think back to my early days of morning brew. And again, you were talking about it before, like there's some amnesia. It's hard to remember the exact thing, but like, I, I do not believe that I was so energized on day one about writing a PDF for myself and for students.

Auren Hoffman (57:24.354)

Yeah. Yep.

okay.

Alex (57:49.854)

and like feeling like I was changing the world with it and feeling like this deep energy around it. I believe energy came later. I believe I felt like enough, whatever the minimum threshold of energy is, I felt just above it to keep me going. And then it was traction and momentum and hearing from students that raised the energy level. And so I have this belief that if you just follow your energy and you kind of expect seven out of 10 energy that you feel in order to start something,

Auren Hoffman (58:01.187)

Yeah.

Alex (58:18.762)

You will never end up starting anything worth doing. And I actually believe like the amount of energy you need to feel towards a new product project is probably lower. It's probably like a four out of 10, but you have to have, but you have belief that it's enough to sustain you for a little while. And then when momentum comes, that will take your energy to the next level.

Auren Hoffman (58:37.816)

Yeah, it's interesting. It's like, if you are, let's say you're a, a, a athlete, professional athlete or something like that, like, yeah, I get a lot of energy out of like, you know, taking that final shot in the game or even being in the game, but all the stuff leading up to the game is just grueling. It's just like, it is a full on gruel of everything. What you exactly, what you eat, you have to track, you have to work out in these like crazy ways or you just think of being a standup comedian, just like the gruel of getting to like that.

Alex (58:55.306)

Exactly.

Auren Hoffman (59:07.796)

One joke that actually people laugh at is so hard.

Alex (59:11.656)

Exactly, and I think it's just really unhealthy when people kind of set this expectation of how they should feel based on their Perception of what energy looks like towards most entrepreneurs like yes the first five years of morning brew were like the I would say like the most energized I've felt Holistically in my life, but if you zoomed in if you did like a zoom in of a week in the life. Yeah Exactly. I mean I was like a LinkedIn monkey

Auren Hoffman (59:23.735)

Yeah.

Auren Hoffman (59:34.508)

Yeah, any given hour, you're like, this is tough.

Alex (59:40.812)

10 hours a day for months on end. So yeah, just, yeah, exactly. And so I just think it's, I just think it's actually is really dangerous for people to anchor themselves to that perception.

Auren Hoffman (59:43.724)

I still am, but...

Auren Hoffman (59:53.006)

Yeah, there's just, there's enough of kind of like crap work that people have to do. Like there's a high degree of crap work that everyone has to do. People think like the president of the United States spends so much of their time doing crap work. The president of the United States, Senators, like you ever, you ever like fall around a senator or congressman? Like 90 % of their day is absolute crap. Maybe even 95 % of their day is absolute crap. It is terrible to have that job.

Alex (01:00:07.265)

Yep.

Alex (01:00:18.08)

Yeah.

Auren Hoffman (01:00:21.038)

So it's like, what job, like if you're CEO of a public company, like there's so much crap work that you have to do.

Alex (01:00:26.476)

And I think, again, we live in a time where now because of social media, people see the best, like the 10 % that is the enjoyment time for people. And then we also live in a time where in every facet of life and work, we're talking about over optimization. And so it's like, how do you optimize your calendar? And anything you don't like doing, how do you either teach AI to do it or use Zapier or send it to offshore talent in the Philippines or Sri Lanka? And so I think it just creates this unrealistic view for people.

Auren Hoffman (01:00:33.902)

Correct, yeah, yeah.

Auren Hoffman (01:00:46.648)

Totally, yeah.

Alex (01:00:54.678)

that you're able to basically delegate anything in life you don't enjoy doing and spend all of your time on things that you absolutely love. And it's just not realistic.

Auren Hoffman (01:01:00.75)

Yeah. I mean, if you're a commerce person, like you literally have to go sit there and some old, you know, couple has to like complain to you about the pothole across the street from them. And you just have to like listen attentively for 30 minutes to them. Like that is your job to go do that. And you can't outsource that to the Philippines. There's like, you have to be in person doing it.

Alex (01:01:20.524)

Yeah, and the last thing I'll say is I think people like myself, anyone who is in the position to actually be thinking about the energy and enjoyment they get from their work has to realize how incredibly privileged they are. Because I was thinking the other day, I live in Hoboken and I was at the dry cleaner down the street. This Chinese couple has been running their dry cleaner since 1994 and they're like a super happy couple, but at no point have they...

Auren Hoffman (01:01:33.812)

absolutely. Yeah.

Alex (01:01:49.172)

I'm sure thought to themselves, like, do I love the work that I'm doing and what are my alternatives? you know, let me think about doing this other thing. They very simply, they've wanted to build a life for themselves and this is how they've done it.

Auren Hoffman (01:01:52.727)

Totally.

Auren Hoffman (01:02:00.75)

How do you think about there's this kind of trope with that with like, like optionality and trying to like, how do you think about that?

Alex (01:02:08.588)

Yeah, first of all, I think actually to do anything great, you have to cut off your off your optionality at some point. Like in order for me to be like a media entrepreneur and be known for digital media, I had to basically cut off every other option. And it is why it's a very interesting thing now that I think about where it's like, if I want to build other things, do I do them in the media world? Cause that is like the very specific set of skills that I've built up or do I do something totally different? But I have to basically start from like,

Auren Hoffman (01:02:14.38)

Yeah.

Alex (01:02:37.132)

not having made any of the mistakes. And so I have to make all of the mistakes again. But yeah, my general view is to end up senior or successful in every, and in anything you have to cut off your optionality. Like there's no one, I don't think that like. Elon Musk, like, you know, what's interesting about him is like, I would say he's kept called like the most optionality by having four businesses, very disparate companies, but also he's cut off. Tons of optionality. One option is like.

Auren Hoffman (01:02:57.4)

Yeah.

Alex (01:03:05.888)

having a life outside of his four companies. Exactly.

Auren Hoffman (01:03:07.19)

or yeah, or just enjoy himself or something. And of course, like, I mean, you mentioned recently got married, like that's the ultimate elimination of options, right? And that is the thing that people get so much happiness and fulfillment out of.

Alex (01:03:16.488)

Exactly.

Alex (01:03:22.164)

Yeah, and to that point, that's the thing. Even though you have to cut off optionality, if you've made good choices, you never think about that. I've never thought about cutting off my optionality through marriage, but to your point, it is cutting off basically all of the optionality that existed pre-marriage.

Auren Hoffman (01:03:29.518)

Correct.

Auren Hoffman (01:03:37.954)

Yep. Yep. All right. Thank you, Alex Lieberman for joining us on World of DAS. I follow you at businessbarista on X. I definitely encourage our listeners to engage you there. This has been a ton of fun.

Alex (01:03:49.866)

Love it. Thanks so much for having me.