Lieberman, LinkedIn & Loyalty

Got a different type of newsletter this week featuring our 2nd awesome guest, Alex Lieberman.

You can read my first feature with the legend Tony P in DC here if you missed it.

Anyways, Alex is the co-founder & current Executive Chairman of the Morning Brew. He’s built one of the largest newsletters in the world, sold the company for a reported $75 million & continues to be one of the most followed & talked about dudes on the internet.

He was kind enough to give me an hour of his time & we talked all things entrepreneurship, newsletters, quitting his shitty job he hated, & much more. The convo was so good (and kinda long) that I’m going to split the interview into two parts. So you’ll get half this week & half next week. Enjoy!

Convo with Alex

Cael: Thanks for chatting Alex, and welcome to Trust Fun. I think pretty much everyone who reads my newsletter knows who you are. So thanks for being here. Got a bunch of questions if that works for you.

 Alex: Cool. Let's do it.

Cael: First, why don't you quickly introduce yourself. Who are you? What's your background? What have you done? What do you do now? 

Alex: My names Alex, I co-founded the Morning Brew, which makes business news less shitty. We do it through newsletters, social media content, podcasts. We're truly a multi-platform media brand now. I started the business while I was a senior at the University of Michigan with my co-founder, who was a sophomore. In addition to the Brew. I also co-founded a business called Storyarb, which helps companies and executives tell their stories to the world. The thesis of that business is it's never been more important to be really good at storytelling via content. Most companies are not good at it. So our goal is to help them do it.

 Cael: Did you always think you'd be an entrepreneur?

 Alex: Definitely not. I started my career in finance at Morgan Stanley. There's a lot of entrepreneurs who dreamt of being an entrepreneur from a very young age. That was not me. But I always had kind of like this builder, tinkerer-type mind, and building the Brew really helped me realize that I love building shit. So that's kind of what has kept this momentum going.

 Cael: Super cool. So going back to the early days, eventually you had that tough (& classic) decision "Am I going to keep the side hustle up, or am I going to make it a main hustle?" Everyone always says there's not a right time or a wrong time to do it, but what was the final domino for you in making the decision to go all in on the side hustle?

 Alex: Yeah. Well, it's a very timely question because, last week I posted a YouTube video that was literally all about this decision. So what I'll do is like I'll condense it into kind of a short answer now, but if you want any more context, you should just go to the YouTube video.

 Cael: Sweet. I can link here too.

 Alex: Cool. The long story short is when you make these big decisions, and not just like going all in on a business, but any large, life decision, I think very rarely it's obvious if it's the right decision at that time. Oftentimes, only in retrospect are you like, "Okay, this was the right decision." And, it's also rarely a clear decision in the sense of it doesn't usually happen quickly. It's not something that you just can meditate on for a day, and then make the decision. So for me, it was eight months of pondering. When I started working at Morgan Stanley, every day after work, I would call my mom and kind of talk through how I'm feeling. At times it felt incredibly anxiety provoking. I felt kind of helpless because I didn't know what the right decision was. And I was miserable at work, and so I kind of felt stuck.

 Cael: So how did you get there?

 Alex: I would say there's like 2 or 3 tools that I used the first way that I thought about it is from, the perspective of, like, what if the worst case scenario happens? What does that look like? And so, I played it out. It was like the worst-case scenario is that I quit my full-time job at Morgan Stanley, go all in on the Morning Brew... And then it fails six months later because typically, startups fail. Like then what happens? Jeff Bezos has this framework of "Regret Minimization." How do you minimize your regrets in decision making as much as possible? And so basically, I said, there are two scenarios. 1) I stay at Morgan Stanley, I see someone else built their version of Morning Brew, because they just took the risk to go all in. 2) The other option was I quit my job at Morgan Stanley, I go full time on the Brew, & it fails. And then, I just have to figure out whatever is next. Through the lens of regret, it became so obvious that I would more regret seeing someone else build the Brew way more.

 Cael: I think everyone thinks it's going to be this, like, obvious, no shit moment & decision. But at the end of the day, it took you eight months to finally go all in.

 Alex: Totally. And by the way, a lot of times it will take longer than 8 months. The only reason it took less than eight was because we (myself & my co-founder, Austin) started this business in college, so we had a head start of basically a year while we were students. I think it's completely normal for people to have side hustles for two, three, four years before it makes sense for them to go all in on it.

 Cael: Yeah, totally. So going back to the early days of the Brew with you & Austin, do you remember the first time you guys received a paid invoice? Or like, your first actual real dollars made? What was that? What did it feel like?

Alex: Yeah. It's funny. We weren't making any money yet when I quit my job at Morgan Stanley. When I quit, we had around 50,000 subscribers. It's a long story, but the short answer is that we had to do everything possible to find low hanging fruit advertisers. The first advertiser we had was UVA, their Masters of Accounting program. I was hit up with a sponsored DM from an admissions director at UVA being like, "Hey, apply today to our Masters of Accounting program. You are a great fit." And I looked at that and I was like, if I'm getting this sponsor message from UVA, that means probably a lot of other 20, 30 somethings who work in finance also are, which probably means that they want to get in front of an audience that the Brew has. So, I literally messaged back to the sponsored LinkedIn message, they said they'd be interested, but they were like, "Can you please send us your media kit?" We had no idea what a media kit was. We never had any advertising materials.

 Cael: That's awesome & hilarious. I still get like fucking five of those a week.

Alex: That's so funny.

 Cael: They're like, "Do you want to come get a master's in accounting degree at SUNY Courtland?" I'm like, "For sure definitely not."

 Alex: Hahaha. Everything starts small. Our first ads were for three placements with UVA, $2,700 total. So, $900 per ad. Now, if you want to do a full takeover of a single day's Morning Brew it's $125,000 a day.

 Cael: Holy shit. $125,000.

 Alex: Yup. $900 to $125,000.

Cael: That is so epic. That's a hilarious way to get your first advertiser too. Can you recall if there was a hardest growth threshold that you guys were kind of like stuck at, and what about that stage made it so hard?  

Alex: I would say that the probably the hardest part was….

 To be continued next week.

Staying Loyal

I talked a lot last week about lowering processing fees via Tandym, a branded payments platform. Let’s be real for a second... Shopify, Paypal & all the others take at least 2.5% off the top of each sale. It’s ass. But, if you rock with Tandym, you can cut that down to <1%. This can be MASSIVE savings for brands doing $10m+ per year in top line.

BUT… How do you get a customer to actually opt-in to a branded payments platform? How do businesses like Nordstroms & Marshalls continuously convince my mother to sign up for a new credit card year after year like absolute clock-work? Also, Alex & the team at Morning Brew built one of the most engaged audiences in the world & then sold for $75 million.

Success all starts with a building true customer loyalty.

At birddogs, we always spoke about creating a customer loyalty programs but never got around to because of 2 main (and incredibly bogus) reasons:

1) We didn’t think a male heavy customer base would be into it. We assumed that it was better suited for brands with heavier female audiences.

2) We didn’t have the bandwidth. Our team was lean. We focused on stuff that would drive immediate revenue. A loyalty program is a longer term play.

First, I’d like to debunk the first myth: the notion that women possess an inherent loyalty to brands that surpasses that of men. THIS IS FALSE. In reality, it's the broskis who are showcasing remarkable brand fidelity. Yes, men are even more than women to the brands they buy.

Second, “we don’t have the bandwidth” is ALWAYS a lame excuse for laziness / not knowing how to do something. Tools like Tandym allow you to sit back, relax & let some incredible tech build & implement an ELITE loyalty program for your brand. If you don’t know how to do something, I can almost guarantee that somebody smarter than you has built a sick ass SAAS company that does it for you.

Sign up for a demo with Tandym here. And as always, I’ll send you a free Trust Fun Baby hat for taking the demo.

Brands like Frostbuddy & Kenny Flowers are both running insane dope loyalty programs consisting of tens of thousands of customers.

Here's the crux: by incentivizing your most loyal patrons, you’re not merely fostering warm & fuzzy sentiments (though those certainly rule). You’re strategically growing lifetime value (LTV). In other words, amplifying a customer’s long-term economic significance to your brand. By showcasing your commitment to customer appreciation, you’re not only solidifying existing relationships but also laying the groundwork for ORGANIC growth…

I’d argue those are the sexiest two words in the world right now in DTC… Organic Growth.

Just typing those words is giving me goosebumps.

Thanks for reading this week & thanks to Alex for joining.

Now I’m all hot & bothered. Have a killer Monday & happy April fools.