Lessons from CMOs, Great Storytelling, Freelance vs. Full-time, Follow Your Energy

Alex: What's up, everyone? Welcome back to another episode of Founder’s Journal. I'm Alex Lieberman, co-founder and executive chairman of Morning Brew. Founder’s Journal is my personal diary made public for the world, where I riff about the things that are going on in my life as an entrepreneur and a creator. Before we hop into today's episode, just quick housekeeping. Starting in April, Founder’s Journal is gonna switch from three times a week to one time a week. No, we are not getting rid of the podcast, but as I've mentioned so many times, my goal is to make this show as valuable as humanly possible for you. While I also enjoy creating the content now, there is an idea that we are working on in the background that I am incredibly excited about, but it's gonna take a little bit of planning and so we just wanna make sure we approach it the right way. So we're gonna take a little bit of a breather in April to plan out the next steps for Founder’s Journal, which I think you're gonna love. But in April, each week's episode is gonna be about a very important inflection point in Morning Brew history, with the first episode about how we got our first 10,000 subscribers with the exact tactics and strategies of going from zero to 10,000. So that is the game plan for April. I just wanted to let you know, wanna make sure you knew I'm not going anywhere. I plan to create entrepreneurship content and help entrepreneurs build their businesses for the rest of my career. So you don't have to worry. 

Now for today's episode, we are gonna hit on a number of things. I'm gonna talk about my biggest takeaways from a CMO dinner that I hosted last night. I'm gonna talk about my thoughts on the trade-offs between hiring full-time and freelance employees. I wanna share a few of my favorite lessons from a podcast interview that Shaan Puri did with David Perell. A quick thought on the importance of following your energy even when it's not easy. And then finally, I want to end with some exciting news about a board that I am joining. So let's hop into it. 

Okay, so last night I hosted the second ever Challenger Dinner Series. It was awesome. So I co-host this event with Linda Boff, who is the CMO of GE. And basically the idea was Linda brings her friends, I bring my friends, and it turns into this kind of like creative explosion of marketers with very different brains from very different sized companies, very different industries, sharing ideas with each other. So for example, Linda brought folks like the CMO of Fidelity, the CMO of Calvin Klein, the head of tequila at Diageo, the chief brand officer of TIAA, the head of corporate impact at JPMorgan, right? So bigwigs in marketing at Fortune 500 companies or even Fortune 50 companies.

And then I brought some of my friends, including Nick Sharma, Paddy Galloway, the king of YouTube, the head of marketing of Mschf, which is the viral marketing brand that has just done massive drops like Big Red Boots, Robin Arzon, the Peloton instructor, and other folks like that. And so the whole idea is 20 of us sitting around a dinner table talking about kind of our areas of expertise and sharing knowledge to be effective marketers in 2024. And so I just wanna share a few of my biggest takeaways from this conversation. 

The first one is that whether you are doing marketing as a Fortune 50 brand or as an up and coming brand, the most successful marketers are incredible at inserting themselves into culture in a way where something is in the zeitgeist, but it hasn't been called out yet. Great brands recognize the thing that isn't called out and then they insert themselves into it. And so whether it was Calvin Klein, who in the last, let's call it year and a half, blew up from the main character of The Bear being kind of the spokesperson with the now famous underwear ad. And I think it absolutely skyrocketed kind of visibility around Calvin Klein. And in a way it was latching onto a creator who is on this massive upswing now because of the success of the show The Bear, or when we had the head of marketing from Mschf talking about why Big Red Boots absolutely crushed it. In both cases there was this deep awareness of what are kind of unspoken things that are happening about in culture right now where chatter's getting louder, but it hasn't been called out publicly. And it's like by being the first one to call something out publicly and insert yourself into it, you get a lot of the benefit. So that's the first big takeaway. 

Second big takeaway is my observation of the hardest thing that Fortune 500 CMOs have to deal with is how they can take creative risks. There is just so much more to lose, there's so much more bureaucracy, it takes so much more time to push out marketing campaigns. Also in the world of Fortune 500, CMOs don't stay at companies for very long. I think the average CMO stays at their company for two to three years. So it's hard to think very long term. And so that was the biggest thing that I was hearing, is kind of how can you take creative risks when there is a lot of risk if those creative risks do not pay off?

The next one is one of the best ways to stand out as a startup via short form video is to sell people on your story versus your product. And so this actually came from Jake, the co-founder and CEO of Mid-Day Squares, which is the better for you chocolate bar brand. They're a Canada based company, they've sold a shit ton of chocolate bars and they are unbelievable at organic content, specifically on Instagram and TikTok. And what he basically said was, look, at the end of the day, we are not gonna succeed as a business by selling our features. Like we're not gonna succeed by selling our ingredients or selling that we’re healthier or better for you. He is like, everything's healthier, better for you. He's like, we are a commoditized product. And he owns that, but he is like, what people will buy is our story, right? And so us creating content about how the fact that we did a recent manufacturing run and there was a defect in the labels in our manufacturing run and we had to as a team come together, get scrappy, and figure out what are we gonna do with our labeling and these defects, because we could lose a shit ton of money. And taking people through that story, this underdog story and how it's overcome by young entrepreneurs, is way more likely to have people latch onto the brand and then try their product versus just trying to sell the ingredients of a product, which anyone can do. 

The next thing from the dinner is about creators. So the best creator relationships are a combination of relationships that are highly authentic to the life of the creator, and the best creator relationships are long-term relationships that feel way more like a partnership and less like a transaction. So going back to, you know the example of Jeremy Allen White with Calvin Klein, right? Like it was very authentic for him because he already wore Calvin Klein, or you know, we had someone from Diageo in the room and they were talking about with one of their tequila brands, how they've been partnered with Jimmy Kimmel for a very long time. And it just so happens that Jimmy Kimmel has continued to be the host of the Golden Globes. And so that has given them way more platform than they were expecting. But the reason these partnerships have worked is because the creators, and it's funny, like celebrities or actors, I just view as a different version of creator to kind of like the modern day creator being a YouTuber or a TikTok or et cetera, is these creators authentically use these products before they partnered with the brand. And they set up these partnerships in a way where they want them to be successful for decades, not a few months or years. These aren't transactions, these are long-term partnerships. 

Two more quick learnings from this dinner. Paddy Galloway shared a few of his biggest lessons around YouTube right now, and two things he said are, he thinks there's an opportunity for bigger companies to play on YouTube. And one of the best ways to play on YouTube as a bigger company is to latch onto great creators by giving creators access to your company's technology or your facilities, like something that the public doesn't have access to but is valuable and a creator would love to talk about.

And so a great example of this is like Cleo Abram, the amazing YouTuber, has like 2.3 million subscribers. She just did a great video on Formula One on YouTube, which you should watch. It was great. But part of her video was exploring the engineering of Red Bull's Formula One cars. Red Bull gave her complete access to their facilities and to their cars in a way the public would never get. And all of a sudden not only, you know, did you gain loyalty and interest in Cleo, but now I'm as interested in Red Bull as ever before simply because so much of her video took place in that setting. 

And then the final thing that Paddy said is that most amateur YouTubers do not take thumbnails and like the packaging of your video nearly seriously enough. Everyone thinks of YouTube as a viewing platform. He thinks of it as a clicking platform. His view is like 50% of getting views on your YouTube video is getting people to click on it, and getting people to click on it requires a great thumbnail and a great title. And what he said, he talked about a client he had been working with that spent literally like a year on a single video and also had a crew of a hundred people. And he said, he asked this brand, how long did you spend on the thumbnail and the packaging? And they were like, two hours. And he is like, so you spent 99% of your time on this one thing, but the thing that is just as important, you spent 1% of your time.nHe's like, the ratio is so off for most creators. 

So that is the Challenger Dinner Series, gonna be doing more of them in the future and I'll keep sharing insights, but honestly I love kind of this dynamic of young fast risers in industry with titans of industry that've been in the game for a long time. It leads to really interesting conversation. 

Okay, let's talk about talent. Now, something I've been talking about a lot with my co-founder at Storyarb is the decision of when to use full-time and freelance talent. And I'll just say I kind of have two pretty strong views on full-time versus freelance. My general rule is anything that is central to your core competency as a business is something that should be full-time. If you're a technology company, your engineers should work in-house or full-time. If you are a media company, your content creators should be full-time. You know, if you are a, what's another example? Like if you're a consulting company, your consultant should work full-time. And the reason I say that is not because I actually necessarily care about the number of hours that people are working, it is more about the focus, and there is something to having singular focus. But also when I think about every business, your goal is to build up a certain competency that becomes a moat for you. And that competency ultimately is the output of having differentiated talent that's really talented in the competency that you're creating.

And so to me, the way you have differentiated talent is being able to one, spot talent that has a lot of potential, and having kind of this secret sauce internally of taking that high potential talent through training and development. And that's kind of what your secret sauce is. And so if you're just working with freelancers, the issue is, you end up onboarding training and developing this talent and you're always at risk for having people leave the second that you train them up. And to be honest, that's why I always find it remarkable in like the investment banking business, how these banks continue to stay competitive, where the average investment banker stays for let's say two years and then they leave, they go to private equity, and these banks put so much resource into recruiting and training these people. I mean, in my head, maybe like part of that makes me realize that it's actually not highly differentiated work since you can just kind of plug people into a system. 

The one other thing I'll say about full-time and freelance is, I've said this before, but I love the idea of starting someone freelance and then hiring them full-time once everyone knows if they're a good fit for each other. I think it's great as a business to know if this person is a good fit for your business. And to me the best way to see that is through them actually working in the business. And same thing for the person working. The only way they can truly know if they like working within your company is by doing the work. So I don't think it's possible for every role, like if you're in a business that is customer facing, I don't think you can do customer facing roles that are freelance to full-time. And also if someone is in a full-time job right now, you know it's not probably realistic to convince them to go from full-time job to freelance to full-time. But when possible, I think this strategy works exceptionally well. 

Okay, let's talk about storytelling. I was recently watching an episode of a podcast by my friend David Perell; it's called How I Write. He has conversations with some of the best storytellers and writers in the world about their process for writing and what good writing and storytelling looks like. I highly recommend the show, but I specifically want to talk about his recent conversation with Shaan Puri and some of the biggest lessons that Shaan shared. First of all, Shaan is the co-host of My First Million, and he's an exceptional storyteller, but I think better than just being a great storyteller is he's really put in the time to think about what are kind of like the frameworks that inform how he tells good stories. So I just wanna share a few of my biggest lessons that Shaan shared. 

The first is told this story about these two guys, Dylan and Henry, who I know well, and they're short form video creators. They started with a short form video agency called Clipt, which still exists, and it's a way for you to hire offshore short form video talent to create short form videos for you. And then they went from that to creating like original short form video content on YouTube. And basically the lesson they taught Shaan is for many months they had been creating short form videos every single day. They weren't getting a lot of views. And Shaan was kind of puzzled, like, why are these guys putting so much effort into these videos if they're not getting a lot of views? And what they basically said to him is their strategy was not to necessarily get the most views, it was to create what they call a binge bank. And you can think of a binge bank as basically a living, breathing resume or portfolio for a content creator. And so their idea was if someone is interested in Dylan and Henry's work and they kind of enter their ecosystem through one of their videos, that person can then just binge this entire bank of content they've created, and in bingeing that content for maybe 20 to 30 minutes, they can get a really good sense of who these creators are, how good their content shops are, and what they stand for. And so I think that changed Shaan's view of like always just thinking about driving engagement and impressions, and started thinking about things more through the lens of like, how do I create a binge bank? How do I create something that if someone wants to learn about me and like my fundamental views of the world, they can just go to my Twitter feed or any of my other social handles, they can read through or watch through and get a good feel for who I am. 

And the way that I internalize this lesson is I thought about every time I write a piece of content, is this a piece of content that I feel like is a good representation of who I am and how I view the world? Like would I be proud for someone to consume this content? 

The second lesson that Shaan shared, which is obvious but so many people don't do, is he wanted to get better at storytelling. And so he didn't study entrepreneurs to get better at storytelling. He didn't study VCs to get better at storytelling. He studied the best storytellers in the world, and the best storytellers in the world are typically authors, screenwriters, directors. And so he told this example, oh, also comedians, he's super into studying comedians like Hasan Minhaj or Dave Chappelle. But he talked about a lesson he learned from Aaron Sorkin, who is responsible for creating West Wing, Newsroom, Social Network. And Aaron Sorkin believes deeply in this idea that the key to great storytelling is every great story has intention and obstacle. And Shaan actually shared this funny quote by Aaron Sorkin in the episode where Aaron says, “I worship at the altar of intention and obstacle.”

And basically what he means is, at any given moment in any given story, the hero of the story has to have a very clear intention, as in, what do they want? And then a very clear obstacle, as in, who is in the way? And If you are watching a movie or reading a story, you should be able to stop at any moment and be able to name what the intention of the protagonist is and what the obstacle is that stands in their way. And if you can't, it probably means the story isn't strong enough. So classic example is Harry Potter wants to live, Voldemort is the obstacle who is trying to kill him. And this applies to all stories, by the way, not just life or death stories. And it's even more impressive if the story is low stakes, like not life or death, because it usually makes it more relatable when the intention of Harry Potter is to live and the obstacle is not dying. It's a good story, but people can't really resonate with that. So actually the best stories are ones that people can see themselves in the shoes of the protagonist and what they're going through. 

The final lesson I wanna share that Shaan talked about in the episode is basically the importance of working backward from emotions to define your stories. And he basically gave three examples that taught him the importance of working backward from emotions and also visualizing these emotions in the context of a single person that you're telling the story to. So he gives the example of this guy Steve Bartlett, who is now a big time podcaster, an entrepreneur. He has his podcast Diary of A CEO, which is huge. Steve Bartlett used to be an intern for Shaan. And Steve Bartlett basically said, whenever he would create a piece of content, he would think about Jenny in her bed. And what he meant by that is the typical consumer of content is someone who's just like bored, lying in their bed, scrolling through social. And you'd always think about, what is the emotion that I need to drive for that random person in their bed scrolling through social that is going to get them to stop in their tracks? Shaan then fast forwards and he says he was talking to I think the CEO of Buzzfeed at some point, and the CEO of Buzzfeed, as Buzzfeed was fast climbing, and like they were at peak, said, when we create stories, we think about Debbie at her desk, not Jenny in her bed, Debbie at her desk. And it was the same thing. How do we get Debbie, who's mindlessly scrolling at her desk maybe while having lunch in between work meetings, what is the emotion we want Debbie to have such that we are confident she's going to stop scrolling on her phone? And then the final example is Shaan was talking to an owner of an agency, specifically an agency that did viral social media marketing. And up until this point, Shaan didn't think it was possible to just like consistently go viral, like you couldn't manufacture virality. And this agency owner shared that like the last 10 campaigns they did, eight of the 10 were viral. And basically what this owner said to kind of bring this whole point together is the owner was like, every time we create something, we work backward from an emotion. And he said, the only thing that people will share are the following acronyms: LOL, WTF, OMG, Aww, or Wow. And basically when you are thinking about a piece of content, you should be thinking about one of these acronyms and you should be so confident once you create a piece of content that you're going to drive one of these emotions for a specific person like Debbie at her desk, and if you don't feel confident in that, you probably haven't created a good enough story that will evoke enough of an emotion to get someone to stop in their tracks. 

So that is the Shaan Puri and David Perell conversation, ton more meat to the episode. So highly recommend you listen to their conversation, but those are a few of the highlights. And then two final things. The first is just a quick anecdote about the importance of following your energy, even when it means losing out on opportunities, money, social currency, et cetera.

So the quick story is there's a project that I've been exploring for the last several weeks and there are a number of really cool things about this project. I get to learn from really smart multi-time founders. I'm able to immerse myself in a space that I know very little about, which I generally am excited about because I can learn a lot, and there's the potential to make a bunch of money, but there's one issue to all of this. I can get excited about it no matter how hard I try. I have spent time studying the space, I've spent time just trying to kind of work through some of the things we're talking about, and I just, it feels like a slog. It feels like I'm stuck in quicksand as I'm trying to run around a track.

And so I think the best thing that you can do in these moments is to one, have the self-awareness that this is what you're feeling. And as soon as you're feeling that thing, communicating it to the people that it's really important to know exactly where you stand at all times. And so I've communicated to these other founders that feeling kind of like lethargic and unexcited about what's going on, and it's no one's fault, it's just a feeling I have, but I wanna make sure that they know because they deserve full communication. They deserve someone who's as excited as them about the project. And so even though it could end up meaning down the road losing out on monetary opportunity, not being able to collaborate with them as much, or like other work opportunities, like things that are external validators, I think it's so important to not continue spending time on things that are not giving you energy.

And then the final probably most exciting update I have is I am officially joining a nonprofit board. So I was introduced about a year ago to a nonprofit called Experience Camps. Experience Camps is this amazing organization that helps children navigate the grieving process after they've lost a sibling, a parent, or a relative. And Experience Camps has been around for a number of years and its core offering has been sleepaway camps. So they have locations across the country every summer for a week. Grieving children can go to one of the locations that Experience Camps has. There are counselors at the camp. I'll actually be volunteering as a counselor this summer at the Pennsylvania camp, as will my sister. And basically the sleepaway camps are, let's call it 90% to 95% just normal sleepaway camp for kids to have a fun time together, and 5% to 10% grief counseling with actual professionals at camp. It's something that obviously I feel incredibly connected to, given I lost my dad when I was young, and if I knew about Experience when I was going through the grieving process, I think it would have removed a lot of the residual pent-up grief or dulling of emotions that I experience today as a function of having called a more complicated grieving process. And so I'm incredibly passionate about what the organization is doing. 

I'm also really interested in taking kind of like the scrappiness and momentum that I've brought to startups in the past and bringing that into a nonprofit context. Given the story that at least I've told myself about nonprofits is that they can be too meritocratic, slow moving, not action oriented enough. So first of all, I'm interested to learn if my story's actually correct and also how I can bring kind of like speed and action to the organization. And I'm also excited about it because I think I joined at a really interesting time. Experience Camps has such an amazing foundation, they've helped thousands of kids navigate the grieving process and kind of be there to support kids where they're at when they need it. But it's an inflection point because at the end of the day, you can't scale this thing infinitely with physical sleepaway camps, right? You can only scale that so much. Sure, you can add locations, but there are gonna be millions of kids across the world that won't be able to go to sleepaway camp in the summer. And so what I find fascinating is helping to support this organization to scale in two ways. One, how does the organization scale its impact? So how do you help all of the millions of children that are navigating grief, but ultimately, beyond children, navigating and helping anyone navigate the grieving process? Because grief is one of those things that we all experience at some point in life. But then also as this organization becomes more of like a big scale institution from a fundraising perspective, like how do you actually drive the revenue that you need to make this like a legit business, like an at scale business?

And I remember I spoke on a panel a few weeks ago with someone who's been in nonprofits for a very long time and she's super well respected. And when I asked her, how do you think about the way that nonprofits are managed differently than for-profits? She's like, I don't think about them different at all. They're both run as businesses; they just have different tax statuses. At the end of the day, you still need to pay people, you still have your costs, you still need to run a profitable enterprise. They just are different. They just literally are classified differently by the IRS. 

So anyway, I'm super excited about Experience. I'm definitely gonna be talking more about them in the upcoming months and years, and I think there's just so much I can learn, and most importantly, I think it's gonna be the most fulfilling professional experience that I've had in my life.

With that, thank you so much for listening to Founder’s Journal. As a reminder, we are gonna be going to one episode a week for the month of April so that we can really plan out what we plan to do with the show moving forward. Again, some really exciting things happening in the background, but for the month of April, you can expect an episode each week and each episode will be about a key inflection point in the history of Morning Brew, and specifically what happened, so you can apply it to your own business. Thank you so much for listening to the show and I will catch you next episode.