Adam Ryan on Building a Creator First Workweek

Jacob: Something you may not know about me, but for about 30 minutes, I thought about becoming a history teacher. It’s actually the major I chose when I was accepted to college. Then quickly realized that teachers don’t get paid a lot of money, and I quickly shifted away from that. You were a high school teacher as far as I know, and you have your bachelor’s and your master’s in education. How does a teacher go on to become the CEO of a media company?

Adam Ryan: All of our journeys aren’t linear. I think it’s every background builds on top of each other, and I feel incredibly lucky and blessed that I had education as a foundation of my background. The story essentially was I grew up with teachers and nurses in my family. There’s a story that I remember us walking by the business school and my mom goes, “What job do you get when you go to business school?” I was like, “I don’t know.” Then I walked right into the education school and wanted to be a football coach and a social studies teacher.

I quickly realized that I wasn’t the hero I needed to be to teach ninth-grade American government. I loved all 128 students I had, but I actually really loved business at the time. I had a couple of internships for Red Bull and Proctor and Gamble and HP and just started to love business and sales and was making good money but I was teaching. I was like, “Teaching’s foundationally, just trying to help people get to an outcome through influence.” I was like, “Oh, I could do that on the corporate level.” I got my master’s degree in workforce education with an emphasis in online which in 2013 my dad was like, “Wait, what?”

The goal was to create online curriculum for corporations where I would be a corporate trainer, but primarily doing online learning. When I went to potentially go explore that route post-master’s degree, I was like, “I can’t teach anybody shit because I don’t know anything.” I got a job at a media company and I just absolutely fell in love with it and then it was off to the races.

Jacob: You say you spent four years at the hustle starting first in sales and finishing as the president. I’m obviously at Morning Brew. I think we were friendly competitors.

Adam: I like friendliness no matter competitor or ally. I think the reality is I did a pitch one time to Austin Rief. Our audience overlap was about 15%, but our advertiser overlap was 100%. It depends how you want to deem competitors.

Jacob: We weren’t the first newsletter brands ever, right?

Adam: No.

Jacob: This game had come before us. There was many before that. When it comes to serving a broad audience, which we both did, we were probably two of the most successful. Why do you think these products worked? In 2022, do you think an entrepreneur could come along and create a competitor?

Adam: Yes, the answer quickly, not in the same way. You couldn’t do it. The environment has shifted. I think the reason why 2016 was this beautiful time to build a mass newsletter business was because you had DailyCandy, you had TheSkimm proving out the medium, almost like wedging that conversation in that newsletters can be a place of attention. On the business side, it hadn’t been captured yet. We were able to do that in a good timing. Also on the flip side, paid acquisition and referral programs were the number one and two ways both companies grew.

I remember at one point we had taped a dollar to the person who led our growth and said, “This is how much we want to acquire an email address for.” In 2022, that is impossible to do that. Maybe except on TikTok, but that’s a different thing. Then referral programs, it’s not like they don’t work today. They have lost their luster because of saturation in a way that just like gamification can only work if people are excited to play the game. That game has been played and it hasn’t been adopted. If launching a newsletter business in 2022, you better have different ways to grow than the two ways that The Hustle and Morning Brew did.

Jacob: We’ll come back to growth in a little bit because I do want to talk about growth and, and Workweek. Let’s ground this conversation a little bit. Workweek launched about nine months ago. Your LinkedIn says you launched it nine months ago but you actually officially announced it only I want to say five months ago.

Adam: Not even. Four months before that.

Jacob: Not even, right? You’ve got 10 industries that you cover, 12 creators including yourself. Where did the idea come from to launch Workweek and why was this the thing you wanted to do next?

Adam: It’s actually nothing to do with media or money or creators. It started because I found myself in a place in the spring of ’21. The Hustle had just sold the HubSpot. I was doing a bunch of random shit. I started investing with the Chernin Group as an operating partner. I just wasn’t fulfilled and just felt like, “I’m a builder. This is what I love to do, but I don’t know what to build.” I also wanted to work with people that I loved. That doesn’t mean I needed to know them, but people that give you energy and excitement and make you be better. The other piece is I was offered lots of different opportunities to be like, “Hey, do this newsletter business. We can sell it in three years and do this.”

This is just not the game I wanted to play. I didn’t want to do an ad agency. I didn’t want to do these things that just seemed like they were arbitraging the momentum that I had built. I sat down with Becca who’s my co-founder at Workweek and we live about eight minutes from each other. We sat down at a coffee shop and we just started talking about what are the things we loved most about working together? What is a culture if we could choose it from the start that we would be proud of? We wrote down a set of values and operating principles with no Workweek, no business, no revenue, nothing, and just said, “Could we build a group of people that match this?

If we do, could it be something we do for a very long time?” That was the start. We wrote that down and we still use those as our values at Workweek today and operating principles and will be like, “Wow, these are so thought over.” It took us 30 minutes because it just came from our heart. It came from who we are as people. Then it was like, “Okay, cool. This is good. This makes us feel like we can do something for a long time.” When you start to have longer time horizons, you can start to take way bigger bets and ideas.

One of the things that I thought about is I have been classified immediate person. My career has been spent in media. It’s also what I know. I can’t run away from it, but in many ways, on the investor side, I was shocked. It’s just not a good business on the markets. Public markets don’t value media companies, startups just are dying for software companies to buy them. There’s just very few media companies that economically achieve massive impact. Specifically, the number 10 billion came to mind of what media companies have done have been valued at 10 billion created in the last few decades.

Netflix and a few others, but none that actually cover anything related to news at all. Becca and I were talking about it, I was like, there’s got to be a way to do this. There’s got to be a way where you can take a step back and throw away the old playbook and create a new one where could we create something, an ecosystem that’s worth 10 billion one day? We’re more than comfortable committing a very long time to that if we can work with the people that we love. That’s what started the Workweek idea and path.

Jacob: On your about page, you say that people follow people, not institutions. In some respects, I agree with you. Yet the most successful media company in the world is a 170-year-old institution. From a business perspective, Bloomberg, Wall Street Journal, and FT are all centralized institutions even Fox News, which is a talent business, has consistently lost hosts, and yet it continues to grow and generate more money than it ever has before. Is it actually that people trust people and follow people or do people like people backed by institutions and brands?

Adam: I got to tell you where Workweek came from and where that line came from. I started helping a bunch of people. In January 2021, I started reaching out to a bunch of B2B-ish creators. Not all either. I reached out to someone who cooks but I started reaching out to creators and honestly just offering free time and saying, “How can I help you?” Started talking to them. In total, in that springtime, I met with over 100 creators. A couple of those people stood out. Mario Gabriele with The Generalist and Packy with Not Boring.

One of the things that Packy said, and he knows I tell this story now and he cracks up, but he was like, “I want to make $1 million this year.” I just looked at his business objectively and I was like, “If Jacob Donnelley or myself looked at this business and the engagement you’re getting, this could do 10 million this year.” The light bulb clicked off of Packy had this huge amount of people with massive influence that literally he was replacing Gartner. He was changing the way that people viewed what software were best in class, and he’s doing it out of a basement and he’s just this one person.

That’s where that came from is people are following these individuals and their success is unbelievable, but they’re not capturing the value that they’re worth. This isn’t a new story. If you want to bring up old institutions, the LA Times is 120 years old. They have influenced where Olympics are held. They have changed culture in every way in the most culture-driven city in the world. Three years ago, they sold for a 10th of what my HR software is worth. The cultural liquidity of what media companies offer has never matched the economic liquidity.

That to me, going from a tiny example of Packy saying, “I wish I could make a million,” and me being like, “It could be 10 to the LA Times, not at all even representing that.” There’s a problem that’s broken and that’s what I mean by that though, is I think there’s the shift of individuals having the opportunity to take over institutions from a consumer standpoint, but also there’s a way to capture that better on the liquidity side.

Jacob: Let’s talk about the Workweek model. You have, like I said before, a network of creators across a vast number of industries. What goes into identifying creators that you want to partner with? What is your qualification process?

Adam: I believe there’s a lot of subject matter experts out there in the world. I think subject matter experts, you work probably with 10 subject matter experts on the Morning Brew team. Just that one business has at least 10. They might have 50 for all I know. There is a lot of people that know industries in and out. There is very rarely that many voices of authority in a space. My belief is that you can help people mechanically become a voice of authority.

I can’t help them become a subject matter expert, but I can help them with the mechanics to become the voice of authority in their space. That’s just as much of their own willingness and desire to become that as well as their expertise and then as well as the mechanics. Our model is set up to help subject matter experts become voices of authority in their space. From there, how we do that, every opportunity is different which we can get into more, but that’s really at the core of how we start.

Then the question is, and I get asked this all the time, it’s like we have franchising climate, FinTech, marketing. We have all these things in it, and they’re like, “Adam, how do you vet for subject matter expertise?” I think my very limited time working at the Cheltenham Group really helped me identify as a deep generalist of someone who has like, “Okay, I’m analyzing a children’s media company and I’m analyzing a plant media company.” I have to understand what are these? The reality is the mechanic the Cheltenham Group has proved this, the mechanics are almost always the same for all these roadmaps.

You have to understand are these people actually capturing the cultural liquidity that you want? One of the questions I start with, which is the first time I ever talked about this publicly, but I always ask, “What are your inevitable truths of your industry?” They’ll say, “What do you mean?” I’m saying, “What does it mean to be a great media operator? What’s an inevitable truth? Every person that’s a great media operator is what?”

I dig in on that. You can just tell if they can go on that, and of course, we then have them write and try it out and get their words. If people instinctively have answers to that question, they’ve thought a lot about that space. If they can back it up with facts and knowledge in their writing, it proves out to be the case. I think it allows us to lift voices in many ways. When we launched, a lot of people were like. “Oh, they’re tiny. No one knows them, whatever.” I think that’s exactly how voices get diminished. It’s the same crowd, it’s the boys club that keeps shouting the same voices. We actually have a really unique opportunity to lift voices up that are subject matter experts through a question like that.

Jacob: In the piece I wrote about you guys when you first announced your launch, I wrote, “If you’re a creator with a large following, why would you choose to get hired by Workweek versus doing it on your own? If you do want to be part of something bigger, why choose Workweek over the other media companies introducing newsletter offerings with a big data audience?” I guess my question for you is what is your pitch to creators to make them understand that working with you, a company that is about five months old is the right company to work with?

Adam: I think since then, we’ve brought in Nick Sharma who is a really big creator, I think in that definition of probably how you would use. Nicole Caspersen didn’t have any IP when we signed her. We’ve done all across the land and it’s only evolving. There’s no pitch that’s the magic sauce and it’s really listening. I think one of the problems with crater platforms which is in some ways we compete with no one and in other ways we compete with everybody. Where could you go to sub stack and use a platform?

Could you go to Morning Brew? Could you do a bunch of media work at a media company Axios? Options are endless. The term that I started to use are, could be creators and that’s a good thing. If you’re a good enough person at creating content in this expertise that you have, you could do anything. You could raise a venture fund, you could launch a paywall, you could start selling ads, doing essays, launch a podcast. You could do a bunch of options. You could go work for a media company or do it on your own.

Options are endless. What I wanted to start to build with Workweek is a business model that matches that. Because if we can’t grow and give options to creators and allow them to actually achieve things that they are their biggest desires quickly, we don’t have a business. I don’t know when this podcast will be released, but you’ll see soon we have a senior team that represent absolutely amazing operators and education, advertising, subscription, venture fund, events, you name it. What we try to create is this out-of-box operating system.

There are some tactics there financially that make more sense for us to do this than a lot of media companies. When we go to a creator, all I do is listen and say, “What are your wildest ambitions? What do you want to do? Who do you look up to? Do you want to run your own company one day? Do you want to run a venture fund? Do you just want to write a newsletter? Do you want to manage a team?” Honestly, every answer is almost different and because of that, our relationship with every creator is different. I think our advantage is that you’ll never have to fit a round peg in a square hole like I think a lot of media companies force you to do.

On the other way, as a platform, you’re normally only siloed and your priority is only the way you make money, which is normally limited. Our pitch to craters is we allow you to be you and achieve your dream and if we don’t have that tool kit in the operating system that you want to do, I’ll go do it, I’ll go find it. Sooner or later, I think we can start to support craters in their full journey, no matter what that looks like.

Jacob: One of the questions I have had multiple people ask me about your business, and it’s why you’re actually the first guest for this new season is, it’s great to have all these different creators but how do the terms of these deals work? Are you partnering with these creators? Are you aqua hiring the creators? Do you own the IP? Do they own the IP? Are they stuck with you? I’m telling you so many questions I received about this part of your business. Can you talk about that?

Adam: The answer is yes to all of those. I don’t say that to sidestep the question, I mean that that’s our advantage. Our legal team loves us because my legal fees are the biggest cost of the business almost at this point because every deal is structured differently. The way that I go to a creator when they’re like, “Hey, this is it and we find it’ll be a match and we’re all good.” When it comes time to do that, I say, “Here are the 15 levers that Workweek has. They all can help you be successful in unique ways. Which ones do you want to pull? Then here’s what we need in return for that.”

Because we aren’t forcing people to follow one contract, whether we spin it out of a [unintelligible 00:20:51] or we buy the IP or we do a rev share. All of the options are different and [unintelligible 00:20:57] out of all the creators we’ve signed so far, truly no deal is even remotely the same almost. I think that actually helps us. I think that allows us now maneuver. Morning Brew announced a creator program. Alex had an amazing tweet thread about that about betting on creators. I think more and more media companies are going to go into the space because they’re realizing individuals over institutions is not a bad thesis.

The problem is they’re going to have to adapt. If you can’t adapt their contract, you can’t adapt with their growth. My asset creator is like. “If they’re sending you a templated contract that they used for 10 other people, I can tell you exactly where your path is going to go. Because they did it with the other 10.” For me, it’s like, “Where do you want to go? You dictate those terms. Here are our levers, here’s what each of those come with.” Of course, Workweek has to pay the bills and do that as well. That’s our approach.

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Jacob: This episode is brought to you by Omida on May 4th. They’re hosting Omida ID exchange in Chicago, discussing some of the most important topics in media. I’ll be there hosting a special edition of the AMO podcast, but you’ll also hear from executives at Access Intelligence, Endeavor Business Media, and many others. Don’t miss your chance to register today. Visit omida.com and click OX5. Now back to our discussion.

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Let’s dive into tactics. In many respects, Workweek has the feeling of a house of brands. Each publication is different.

Adam: That’s a compliment, thank you.

Jacob: You have the Wolf of Franchises, you have Healthcare Huddle, my favorite, Perpetual. This is very much a house of brands, and yet you have built this site on a single publication. It’s Workweek.

Adam: Right now. Yes.

Jacob: That’s my question. Are you trying to be a house of brands, are you trying to be a branded house? what direction do you really want to go in?

Adam: Great question. This goes back to we built our entire business model right now around creators and growth. Investors that get to really know our business super intimately are like, “Wait, are you, Dot Dash? Are you Y Combinator? Are you Morning Brew?” I literally have been compared to them all. The reality is we’ve realized, and we’ve created structured systems for this too. Most creators start to say, “Hey, here’s where I want to go.” The Wolf of Franchises is a really good example since you brought it up.

Day one, he had very set clear of ambitions of where he wanted to take his brand and where he wanted to go. When I reached out to him the first time, he had 15 newsletter subscribers. It was actually after his very first sub-stack send, I reached out to him and said, “I love this, let’s talk.” It was all vision. He has led that vision. That vision right now is we’re building out the wolfoffranchises.com and that will start to be its own brand on its own.

Not every brand, in my opinion, stands up to that immediately. I actually think you set yourself up to fail sometimes when you are so focused on siloing yourself, you lose this ecosystem. Barstow’s an interesting case study here. Look at how Barstow has systematically grown their creators internally. It’s basically you start them within the ecosystem, you have them spiral up, they get big enough, they spin them out. Nowadays they just sell them. That to me was an interesting idea, is could you start to basically use Workweek as a way to help creators get started?

To make them feel like they’re part of something much bigger, which then makes their audience feel like they’re part of something much bigger, which then lends credibility. This is all about making them the authoritative voice. Credibility is a big piece of that. As they get bigger, it’s starting to grow. We have to not cap that. We have to allow them to release. That might be starting your own website, that might be various other things that we’re going to do. Sooner or later over time, just Disney’s known for being imaginative and pushing the boundaries of what’s possible.

I want Workweek to be the Disney of business where we are a holding company in many ways, but we actually have a brand that’s forward, that stands for values and that has a reputation.

Jacob: I guess right now, what is the technical stack that powers the business? You talk about offering courses, newsletters, jobs, and events. At some point, maybe not all right this second but these are all things listed on the site that you’re going to do. What tools are you using to actually accomplish all this?

Adam: Full transparency we screwed up a lot in the beginning with tech stack, I can talk about that. I thought it would take four to five months to find four creators. It took three weeks which was shocking. We thought we’d get to 10 in 12 months and we did that in about two months and fucked up all the timelines of what we want to do. The original idea was to do campaign monitoring for 6 to 12 months and then move to sale through and do a CDP where we started that transition already.

We’re building that out. That will be the main tech stack of the newsletters and using the CDP for various sources. We’re pressed as a website, not anything complicated. I think the best part of our team, particularly Becca and I, is we came from bootstrapped land and I think a lot of media operators crap on raising money. I also have many times on Twitter because they don’t spend it on shit that you have to spend money on. For us, we come from this, “Hey, be scrappy, find your way to do it.” If we can build a WordPress site that we think is cool and beautiful, but it’s not a custom react that we need an engineer to do, we’re going to do it.

That’s been our mentality, but now over time, we did build a database quickly and it just is growing much faster. The amount of data that we’re collecting and ultimately in many ways, we’re a database business and we needed to adjust our tech stack to match that.

Jacob: No, that makes a lot of sense. You mentioned how each agreement is different. You mentioned that each authority decides their own vision, which adds levels of complexity. Because each deal is going to require different things. You’ve got to keep an eye on the various different things you offer, which means the team is going to have to grow rather quickly. You and I have talked about both publicly and privately about the wheel that media companies get on where they start to raise and raise and raise and raise and never get off. We saw this with BuzzFeed with all that stuff.

How do you build this business without getting ahead of your skis? How do you get to sustainability when you’re investing so much and creating honestly, not efficiencies of scale because everything is so different?

Adam: I think that’s the wrong assumption and I’ll tell you why, but a couple of things. We did not expect to go this fast bluntly. I didn’t expect to need to build out the whole, let’s say out-of-box operating system. Because when you’re only supporting four creators on your journey and one of them is you, you can be like, “This is the operating system.” All of a sudden you start expanding that and going faster and you talk to 10, 12, and 20, they all have different needs. You have to hire faster. That was a strategic decision that we made in December when we felt like we had momentum when we thought there was a need in the market that we’re solving a real problem for creators.

We were like, “We have to go all in or we slow down,” one of the two. It’s been wild. I had a baby on January 2nd and the last 90 days we’ve brought on some part-time but brought on about 34 people including creators. That’s bigger than The Hustle was through my four years. That is a lot. What I’m most proud about is that all those people, 100% represent the values that Becca and I talked about. So far, we’ve had to let people go because when you hire fast, you make mistakes. We aren’t first-time operators that just don’t let things go to waste. We have to adjust and adapt. That’s the hardest part about growing fast.

In some ways, we get over our skis in that way I think most, and then the second piece is, I have said from the very beginning to all of our investors, really the whole team that the magic of this business is delegation. If you can find people who are superstars at what they do, you can do this. I say a lot, I say we want to be the Disney business, but I’m a massive theater nerd. I went to the original cast of Hamilton, New York. I’m massive live theater person, fun fact about me. I say, what makes Hamilton so amazing is that it wasn’t that Lin-Manuel was just amazing because he is, but he found the best lighting, he found the best-set people.

He convinced some of the best support actors that would’ve been starring on their own to take pay cuts to do it. He built a surrounding cast that allowed him to focus on the script and being the lead, but let everyone else do their thing. In many ways, we’ve talked about this, Becca and I did from July. We have something in our notes. Build a Hamilton media structure. Our senior team, thus far, three former CEOs without including Becca and I we’ve done two essentially aqua hires to agencies for various business units of people who founded that. Their agencies had four or five people and we brought them on.

Our head of growth was really great. Our head of operation’s amazing. We basically built a senior cast that I think in their own write are some of the best operators I’ve ever worked with in my life. They’re only focused on events or education or advertising or et cetera. Because of that, actually operationally, it feels fast. It feels crazy, but we have such good people focusing on that where instead of doing a bottoms-up strategy of saying, “I’m going to hire the cheap 24-year-old that’s never done this before.” That’s why we raised money is because it was like, “No, I’m going to go build– the people are expensive and we’re going to pay them what they deserve.

I want them to worry about thriving, not surviving, it’s going to be expensive, but let’s do it.” I’m proud to say next month, that bet is that you can get ROI on those hires and next month we will cover payroll or if not 100%, right there with revenue. I don’t know a lot of media companies that are five months old growing as fast as we are, diversifying revenue as fast as we are, build a senior team while not being efficient with cash. It’s in our bones to be efficient with cash. I think you just have to actually execute and do it and hire good people.

Jacob: I want to talk about growth because again, you and I were lucky to work at media companies and specifically newsletter companies that in that snapshot in time really could grow at just lightning speed.

Adam: Crazy paces.

Jacob: It is harder today than it was then.

Adam: 1000%

Jacob: What are you guys doing to grow the various products? Are there any channels in particular that you found effective in 2022? What’s working for you guys?

Adam: Because this is a media operator podcast, I get to dive in and actually talk about my beliefs here. Other people will be like, “This is way over my head.” One of the things that drew me to creators was actually seeing the organic growth of Packy. I was doing the math and I can’t help myself. He says how many new subscribers he has every week and I keep track of it. I did this with Pomp, I did a whole tweet thread about Pomp’s growth that I was tracking organically. You and I know that organic growth is the fundamental way to drive profit. Normally, they’re your highest-quality subscribers as well. They’re where all the juice is basically made.

I was watching Packy and Mario and all these creators just have fantastic organic growth. I started just straight-up reverse engineering what they were doing every second of the way. That’s where speaking with 100 of them last spring, it was like I wanted to know what they were doing. Of course, it came from high-quality content is number one, always with growth. I hear a lot of people always there’s a lot of believers, Nathan from [unintelligible 00:34:25] and I just did a debate on my podcast about growing and various tactics around that.

The reality is I’m not talking about shortcuts that undercut quality content. Let’s just assume that’s there. What I learned was if you actually have an individual who’s saying, “This is my brand,” and they’re active and they have a tent pole of content that they work off of, an essay, a podcast, whatever it is, but they have this tent pole. If you start to distribute that in a really successful way and it’s theirs, the language, the words matter. Great copywriters say this all the time, but for whatever reason, this is the individual over institution.

If you straight up compare the same copy but you say, “Sign up for this institution,” but you’re like, “Sign up for my newsletter. I’m this person,” the conversion rate is drastically higher on the my side. It’s just how people respond. They want to be attached to a human. The organic growth rate of this original thesis of building out for Workweek was you could find creators that their organic growth rate is drastically higher than media companies. That means you also have a core nucleus of subscribers that you can do a lot more with. That to me was the starting point.

Then those things are somewhat obvious, but doing Twitter threads, TikTok, LinkedIn, still very viral platform. Then doing things that don’t scale. I tell all our creators first 30 days you’re getting started, DM people on Twitter, and be like, “Subscribe to my newsletter,” it could work. Then once you start to see product-market fit, once you’re like, “Wow.” If I’m analyzing that business and I’m like, “Referral count is very high for the levels that we set. Your organic growth rate is here, you’re growing.” You have signals across the board where if I was an investor, I’d be like, “Yes, I’d follow on that path. Now it’s time to throw fuel on the fire, which is put it in drip sequences.

Do paid ads, find that piece.” For most of our creators, 75,000 to 100,000 subscribers is their tam. Is on the high-end truthfully. If we can capture that, the faster we get to 10,000, that’s a big step. You get to 25,000, I actually am with great reputation growing across the board, the rest can take over itself for the next foreseeable future.

Jacob: Let’s talk about the sales side of things. What are the products that you’re offering to partners? How are you pricing those products? Is it just newsletter ads? If you’re going to be at breakeven on payroll by next month, how are you doing that?

Adam: We have a bunch of revenue sources. Ours won’t even make up 50% next month. Maybe 50% just right around there. You and your newsletter about us when we launched I got forwarded to me a bunch and everyone was like, “Wow, he was pretty harsh about the sales side.” I said, “He’s right.” The mistake that I very much tell people now is that I told you that we signed so many creators so fast. Honestly, I was just happy to find amazing people that would say yes that I didn’t question at all tactics of where we should go.

If I could go back and I had my choice, I don’t regret anything. All of our creators are amazing. They’re all growing crazy. We got really fortunate with that initial group of people. The reality was, there’s a more strategic way to approach this. I missed it at first. Talking to you and Sean Graffy and others that have done this before, there’s a clear strategy to go. I was just worried about finding really good people that I really enjoyed. That was the downside. It made it hard though. Climate, franchising, FinTech, and media and healthcare, and cannabis were our first group.

There is no overlap of audience there except on the media side. We found a few of them also subscribed to Perpetual, which makes sense. Cannabis, you could be in media and cannabis and interested in media in general, but either way, not a lot of overlap. That created disadvantages across the board on the sales side. We started being more strategic of going pod routes. We’re about to announce another FinTech creator here in a couple of weeks. That will be our third FinTech creator. We’re going pretty heavy. We announced Nick, we have about four or five more lined up to join the marketing team on the marketing pod there.

You create these pods of creators, it’s way more efficient. That’s definitely a route that we’re switching to which was, thanks to your honesty in the email made me question my tactics and come out of my own bubble. With what we actually sell, you asked that question, we don’t do any banner ads. I still hate them. I always have. I won’t do them. We do the regular Morning Brew, The Hustle-style ads. Almost all of our revenue is B2B. We specifically created a consumer section because part of our thing is to make work fun. We want all our creators also to shine their personality and be like, “Hey, I love this sheets company whatever.”

We do have some consumer revenue that’s almost like scheme text-driven short ads. We have content programs, which when you’re known for making great content, you were meant B2B as you know, it’s a hell of a business. We have a Lead Gen program that is different. I was at Spiceworks which was sold to Ziff Davis and I absolutely despised how they did leads. It was gross and inauthentic and had no integrity basically because it was all third-party leads, which is how it exists. We created a new-ish, not really new. Sean does something similar in industry dive, but a more authentic way to do leads that’s not so got you driven.

That’s the philosophy and tactics right now with ad sponsorships?

Jacob: Let’s lean in a little bit because you say you’re B2B. I’d love to understand. I’m uncomfortable with Lead Gen in many respects because it can be so just-

Adam: Terrible.

Jacob: -spammy. I’ve heard stories about media companies sending three, four, five marketing emails to their database a day. I’ve heard just horrible stories. How are you making Lead Gen, not that? What are you doing that’s different?

Adam: You just solve for what sucks. Honestly, that’s almost all of what Workweek is. Just like, “Look, let’s be honest at what sucks about everything, and then let’s try to fix it because we can with time.” That’s the idea. Lead Gen, what sucks? Most publishers lie, they’re not actually users of their platform, they buy it from third parties for $40 and sell it for 200. It’s bad for users. What you’ve mentioned, they send way too many marketing emails a day. They try to squeeze as much revenue per user out on the Lead Gen front as possible.

Three, content’s never actually good. It’s normally made from the partner or it’s some bullshit agnostic thing that they just try to use and change out the sponsors for that doesn’t actually work. Ultimately, it’s a business that is hard to scale if you don’t grow because if your pool remains the same of users, you’re just going to keep asking them for their information. I call it a growth-connected service. If you don’t grow, you should just get rid of it. We started to solve all that.

I’m actually the first Lead Gen with Perpetual that I’m doing. I wrote a very honest– Becca and I actually did it together. Very, very honest approach of how to choose an ESP of if you’re a creator, I would use Beehive, and this is why. If you are mid-tier, I would use Campaign Monitor and this is why. Here’s other options, and if you’re an enterprise solution, I’d use Sale Through, and this is why.

Sale Through is the Lead Gen partner on that deal. I told them I’m absolutely recommending competitors. I’m absolutely talking about people and I drew the line. The thing that media companies have struggled with in the past is that the way you actually build cultural liquidity this term that I took from this super smart guy named Henry but the way that you build that is by looking out for your users. At The Hustle, I made a block list that I lived by and I made the team live by. I was like, “Hey, if this brand is hard to work with or did something shady,” like I talked about it before, but I cut SoFi. I put SoFi on the blacklist when their CEO was a huge scumbag.

I was like, “We’re not working with a brand like that because that’s not what’s best for our users and our readers.” Nathan at Every said if you do something, basically 90% of the full way is normally the best way for a media company. If you’re a subscription company but you just consistently put pop-up ads constantly up and send drip emails, you’re going 100%, it’s not that good of a user experience. With Lead Gen, I’d recommend take a step back, go 90%, don’t make it so awful. Solve for those things, and it’s actually a great way to monetize the base.

Jacob: Can you talk about the Creator Fund? Because you’re now a media company with multiple different creators. You offer multiple different business models and then you decided, “You know what, let’s get crazier. Let’s launch a fund on top of that.” The mechanics here, how does it work? Who has the final say of what gets invested?

Adam: Good question. The fund was out of talking to the creators. I’d say 6 out of 10 said one day they want to invest. Some of them are already investing but doing 2K to 10K checks. All of them said, “I want to invest. I want to learn about investing. I want to be part of that process.” Only one creator thus far has a history where they’ve made more than $100,000 in investments, which is Nick. Everybody else was smaller than that, but their ambition was there. As I stated earlier, we’re about matching that.

I never wanted a fund from day one. It’s a shit ton of work. For the ROI of the company, it’s not there. Right now for the time that it takes, fund economics aren’t ideal, especially at 10 million which is our fund size. The reality is I wanted to offer that to our creators so they could grow and learn and it was important. We prioritized it early. Then the way the economics work is I want basically this to be the creators bring us deals all the time. This is not unusual. You knew about Workweek before we even launch because you have the pulse of media and that’s the same in climate and the same in franchise and the same in all these other categories.

These creators are capturing deal flow. They don’t call it that because they don’t know that’s what it is but they are capturing deal flow. Then it leads to amazing opportunities to invest because we actually can identify these companies earlier. We can use their inevitable truths that they created to create thesis around their areas, and then we can invest in it. There’s an investment committee that we have for Workweek Capital, which is really the final say.

That’s mostly because one of the risks of Workweek Capital is that you could play favorites here. I’m making this up but Nick could come to us and say, “This is a portfolio co of mine.” That he might own a huge portion of it and say, “Let’s invest in it.” We have to have some third party there just to make sure that we’re doing really good investments. We also are doing due diligence ourselves, the creator doesn’t have to do the due diligence, that’s on us. It’s an education process the whole time where we’re letting them know if we pass, why? One of our rules at Workweek Capital is actually write out why if we pass.

Which is a learning for not only the founder, which is missing, most VCs just pass and don’t talk about it. The other side is our creators get to know what to look for and if something missed. Then from an economics perspective, I got to know all of the scout fund. I was offered a scout fund position and I got to know scout funds really well. Which in some ways this is what people would call this is like, “Oh, they’re just providing deal flow and then doing that.”

Our economics are not even remotely comparable to scout funds. Our creators if we invest in a deal that they bring us are taking a huge portion of the management carry. They’re financially being rewarded. I actually don’t even see right now– I say this to our investors, I say this to our LPs. As the GP officially, you have to have someone to do that. My upside is almost non-existence only about the money that I put in.

The rest of it goes into our creators and Workweek. That’s the opportunity for them, is they can actually start to achieve financial upside through investing which is a good way actually to do that. It’s a great way to build wealth. They get to learn along the way and for us, for our LPs, we get more looks than any VC out there, I can promise you. We have expertise to say, “This is good because of this,” and build out the thesis. That’s a little bit about Workweek Capital.

Jacob: I want to talk about you as a writer because you made the masochistic decision to run-

Adam: A horrible decision.

Jacob: -a company, manage a bunch of people, and write a newsletter. Only truly crazy people choose to do that.

Adam: I Know. [crosstalk]

Jacob: Why? Why did you decide to launch Perpetual?

Adam: Two big reasons. There’s others, ego et cetera. I think anybody that writes likes having their name in the lights and I want to be the authoritative voice in media, et cetera, et cetera, all that stuff. There’s two strategic reasons that sound better than those reasons. One is you, Brian Morrissey, Sarah Fisher, all people I look up to almost all three of you I would consider friends in many ways. I’ve gotten to know all of you and just deeply respect the work that you guys do. I knew Workweek was in some ways going to create a business model that goes against some of potentially the inevitable truths that you all may believe. I could be wrong but this business does require narrative. It requires storytelling.

It requires saying, “Your thesis is wrong and I’m going to try to flip it on its head.” It’s really hard to do that and I don’t live in New York. One of my big disadvantages is even though I’m a media person, I live in Austin, Texas and I have my entire career. I have a degree in education and my mom’s a nurse and my dad was in real estate and worked at a grocery store my life. I have no media connections whatsoever. At times, I had this fear with Workweek that I so much believe in what we’re doing, but I can’t walk down the street and have drinks with the person that controls the narrative of the industry.

I can’t necessarily have the inside information of what’s happening on the streets of operators. I wanted to start to write Perpetual to get our story out there but not in a Workweek forward way. The reality is if you read all of my newsletters they’re really just breakdowns of my memo of our round and my thesis that drives us and it’s a playbook into exactly how we operate. I just use the best of other examples that do that and that inspire us. That was the first reason. I wanted to have an opportunity to get our narrative out there that I don’t believe others would give us the chance because in some ways, what we’re doing is going to compete with them or potentially call some of their things that they do wrong.

The next one was really that was out of personal spite, I guess you can say of I just wanted help. The second one is, Becca and I talked a lot about how do you keep the pulse of the operating system that we’re creating for creators? How do I keep a pulse of what’s good and what’s working? How do we help make subject matter experts turn to voices of authority? I identify someone who was the right hand for many years and no one knew who they were. My Twitter followers when I started Workweek, was at 2,000, 3,000. I wasn’t known in any circles. I wasn’t big in the name. I had no newsletter, nothing like that.

I consider myself a subject matter expert who wanted to become a voice of authority. I was like, “Could we execute our playbook on me? Then can I go through that experience authentically and say, “This part sucks. I hate this. Hey, I’m growing here but because you added a podcast to my plate, I can’t do this anymore or this other part.”‘ I have been able to very much go through there. Then have the empathy when I meet with our creators on staff and prospective ones and say, “I get it. This sucks. This is hard.”

It’s been probably one of the most rewarding things I’ve done. It’s pushed me in a way that I didn’t think I’d ever be pushed. I don’t identify as a writer. It’s really hard to do and that empathy, I could have never built by just being a CEO of a media company. You only get that by doing it. I’m so happy and I help our operating team. Our podcast team a couple of weeks I was like, “Hey, your notion template here is confusing. I don’t like it.” I can give feedback and sometimes creators no matter what, some people just don’t speak up and I have the opportunity and privilege to be able to do that. I’m able to hopefully refine some of our systems by going through it.

Jacob: You’re under five months old and the early times of building a company from zero to one just focused on the daily grind. If you could set back and look to the future of the next three to five years, what does Workweek look like?

Adam: Good question. I think we will start to build a newer reputation. Right now, I think we’re seeing maybe some ways as a creator platform or a newsletter business or something. My goal is to be seen as the brand in business that if it’s in your Workweek, we’re part of your Workweek. That’s where I want it to go. Nothing is not on the table or everything is on the table. We can do whatever we want because we’re in the business of business. No industry is off the table and no roadmap is off the table. I think, hopefully, we’ll be known for excellent execution, amazing creators with huge personalities, and great subject matter expertise for lifting voices up that have not been heard before.

Having people, ultimately I hope every person here today is with us in three to five years. We’re building systems to retain talent and team and I hope those people are like, “That was the best decision of my life.” That’s really what matters to me.

Jacob: I want to end with the same two questions that I ask every operator that comes on the show. First, what is a mistake you’ve made in your career that you wish you hadn’t made and what did you learn from it?

Adam: Mistake in my career. I think it’s not taking time to think about what drives you. Shiny object syndrome is real and it happens in business a lot. It’s easy to get caught up in a moment. It’s easy to be like, “Oh, this is amazing.” I’ve made a mistake numerous times where I’m like, “Oh.” Sometimes that may look like a rebound of a company that you’re having a bad experience at. You’re like, “I just want to go to this new shiny thing.” If I could go back and tell myself anything in the beginning of my career, it would be take deep breaths, control where you’re going, think not about tomorrow but think about the day after and see where it goes, and don’t fall for traps like that.

To me, if people do that, they tend to be more fulfilled.

Jacob: What are some advice you would give someone thinking about launching their own media company or looking to make their media company more successful?

Adam: There’s a couple of things. One, just press publish, just go, just don’t worry about it. Don’t worry about perfection. Imposter syndrome, we all have it. None of us know where to start. We all doubt everything that we do. I think people just need to take one step forward at a time. If you’re getting started, if you’re trying to build a big, huge media company, or just trying to start off on a sub stack, whatever it is, just be proud of the step forward and don’t worry about the outcome. Then the last one is, and this is a responsibility for anybody that has a voice in the space to help out people, but reach out to the people you admire and tell them that and say, “I’d love to talk.”

I have done that. I tweeted about this but I got coffee with one person for three years basically in a row, every once a week. That changed my life 1,000%. I was told no many times and people ignored me or whatever. No one really told me, “Oh, I’ll just ignore you.” Just keep pushing and meeting people and your network is really your mode as a human. It’s how you’re made up. I would just take one step at a time and build your network up as much as possible.