A Second Brain, Not an Assistant: beehiiv's Chief of Staff Model

0:09Hello and welcome back to another episode of the Chief of Staff podcast. I'm your host today, Scott Amenta, founder of the Chief of Staff Network. Today's guests are Tyler Denk, co-founder and CEO of Beehive, and Brian Schneider, his Chief of Staff. We're lucky to have both the principal and the Chief of Staff in the room together, which doesn't happen often on the show, but it makes for a genuinely useful conversation. Tyler was the second employee at Morning Brew, where he built most of the technical infrastructure that helped scale the newsletter from a few hundred thousand to over 4 million subscribers before its acquisition by Insider.

0:42He then co-founded Beehive, which started as a Morning Brew in a Box, and has since grown into one of the leading all-in-one platforms for content creators and publishers. Brian, meanwhile, was a standout Morning Brew College ambassador who hustled his way into a full-time role there, climbed from sales into revenue strategy, and eventually followed Tyler to Beehive, where he's now three months into the chief of staff seat. What makes this conversation worth your time is less about what they've built and more about how they built it together. We get into radical transparency as an operating principle, what it actually means for a CEO to treat a chief of staff as a second brain rather than a glorified assistant, and the very specific things that make the principal and chief of staff relationship work or not work in the early days of the role.

1:27let's get into it all right brian tyler so nice to have you here thanks for joining thanks for having us yeah nice for having us so before we get into the way that you guys are working together at beehive i'd love to just hear a quick background story on you each uh maybe tyler you can start and we'll get into some of the details of like the business as well but just a quick background on yourself and maybe how you guys met so we well i'll start with my background

1:54Tyler Denk: and then I'll intertwine Brian's introduction into my life through that. Back in 2017, I joined as the second employee at Morning Brew and did everything from product engineering and growth. So built the content management team for the writers, built the ad management platform for the sellers, built all the growth mechanisms and helped scale Morning Brew from 100 ,000 subscribers up to 4 million up until we got acquired by Business Insider. Somewhere in that journey, we had a college ambassador program where we had a bunch of different students that were on campuses referring the Morning Brew newsletter to different students and whatever on campus.

2:34Tyler Denk: And we had one college ambassador who repeatedly had a thousand referrals every semester, which was a total outlier. And that was Brian. And so when we... I think we were maybe... Do you remember what employee number you were, Brian? I think mine are still at Morning Brew. Still a small office in a way we were. Okay, sure. Also early. Yeah, very small. I think we had either one seller on the team already. And we were looking for another seller. And Brian threw his hat in the ring applying. And I turned to Alex Lieberman, who is the CEO. And I was like, he doesn't have a sales background, but he outsold every student in this massive college master program 10 times over.

3:11Tyler Denk: And he definitely has the hustle to make it happen. And I think that's actually been a bet I've made many times in my career is always betting on hustle over like expertise or experiences. So we made that bet on Brian way back when, and he obviously crushed it, climbed the ranks of Morning Brew. And then I guess to finish out my story, after Morning Brew got acquired, did a year at YouTube and then launched Beehive with two co-founders. Beehive initially, you can think of it as Morning Brew in a box, everything you need to build, scale and monetize your newsletter. We've since diversified into podcasts and community and websites are really an all-in-one content platform for anyone who's creating content online and brought Brian on fairly early here as well.

3:54Tyler Denk: Brian, I'd love to hear your story. But also, what was your secret on Morning Brew? Yeah, honestly, just hustle. I went to a big school, University of Connecticut. There's a lot of people and I just would go to every class and talk to them about Morning Brew. Back then, it was pen and paper. I'd get everyone to sign up and then manually add those all into the Morning Brew subscriber list. But it was a lot of fun. It was a great way to get myself out of my comfort zone. And I didn't love to public speak or it wasn't something that I was great at. So one of the reasons I wanted to do it was it forced me to get up in front of a class of 400, 500 people and talk about something that I thought was cool and interesting.

4:34So I really did that to push myself out of my comfort zone and luckily found a rhythm there at UConn.

4:41Tyler Denk: Just hitting the pavement sometimes is all it takes. Brian, where were you? I think I remember the company you were at before Morning Brew. Yeah. So right after college, I took a full-time job at Prudential Financial. Great company, but just was not the right fit for what I was looking for early in my career. We're really looking to grind and get after something and really have true impact. And Morning Brew was looking for someone to run their college ambassador program. And I had a full-time job, but I still applied because I was like, okay, I can do this. So I ended up working 9 to 5 in Prudential, would finish my job then, go to the office at like 5pm at Morning Brew.

5:15And these guys would be still working away at the WeWork. And I spent a couple hours there at the end of my day and just did that for a couple months. And then when the sales team came up that Tyler mentioned, I was like, hey, can I toss my hat in the ring? I really enjoy working here, really enjoy the team, having a lot of fun with it and just felt like a really great opportunity, again, for me to put myself out of my comfort zone. I had never done sales, but I was confident I could figure it out and learn it and work with the team there to do a good job. So luckily enough, Tyler bet on me and pushed that story to Alex and Austin to take a chance on me.

5:51So came in there, started as a seller, did sales for probably the first year, year and a half, and then shifted into more revenue option strategy. So anything from pricing packaging, inventory management, monetization, all that type of stuff. I helped really grow the business and was there for about 5 years before I ended up moving over to Beehive to help with RevOps, SalesOps, and BusinessOps across the board. And now I'm currently Chief of Staff to Tyler. So it's been a great opportunity and continue to work with Tyler. Yeah. I feel like some people might look at that story from the outside and say, oh, Brian, just right place, right time.

6:29But it's very clear from the way that you and Tyler just described it, that you were putting in the work to be in that right place. And the people around you saw that energy, saw that motivation, and gave you the opportunity that you then jumped on. We'll get into your path into the chief of staff role as well with Tyler. I'm sure we're probably going to see a similar story there as well. um but before we do that since you both ended up kind of in the media space at at morning brew what did you see there maybe we start with you tyler but brian jump in here as well what did you see there that kind of convinced you that like the newsletter economy needed something else um substack had not quite launched at that point i'm trying to think of dates here but um you know obviously there were still big newsletter platforms MailChimp, etc.

7:20None that I loved. So I'm curious what jumped out for you, Tyler?

7:24Tyler Denk: Well, before I get into that, while it's top of mind, I actually wanted to double click on the thing you said that we'll probably get to later around. Brian's journey into the chief of staff role, I think from a listener's perspective of what did Brian do right there where a lot of other people just go through the motions of simple internship, get a job out of college, play it safe. Brian did a lot of things that had no guaranteed payoff of being in the master program where 80 % of the ambassadors just didn't give a shit and did not do anything at all. They just wanted something on their resume.

7:54Tyler Denk: And even those who did try hard, Brian tried the hardest with no guarantee of financial upside or a job or anything. And so I think just putting yourself in a position where you do go the extra mile and hustle without the guaranteed payoff is obviously what landed him the job at Morning Brew and continued on this path. I think that's something intrinsic. There's something that Brian has, which is obviously what most people and employers look for as someone that has that intrinsic drive. And then the other big thing is a lot of patience. And it dovetails with the same theme. There was no guaranteed payoff, but he did it anyway.

8:28Tyler Denk: When he joined Beehive, he wasn't like, I need to be chief of staff. It was a very patient journey. I think I pitched him, I do think you'll get there. But we already had a chief of staff at the time. And so it was a rev ops role where he put his head down and did the work and always did exceptional work and then moved into a more senior position. And then when chief of staff opened up, he was the obvious one to move into that position. And I just think as I see a lot of other people online or interact with other people in the startup or career trajectory, whatever, they rush to be demanding of like, Oh, I want this or I'm not going to do it.

9:03Tyler Denk: And they shoot themselves in the foot because they don't have the patience or they don't play the long game or they don't put in the work. I think Brian's been like the antithesis of like all of those things. Yeah. Or because I've done this and I followed the rules and climbed the corporate ladder, I therefore deserve this. And we all know that's not how it works, right? The proof is very much in the pudding. And putting in work on the ground and kind of showing, especially in like the relationship that you guys have built now over years, that has translated into what I'm hoping we find is an effective chief of staff and principal relationship, it took time.

9:38It took time and energy from you both to make that happen. And Tyler, I love that you said patience because sometimes that is the most important thing. Not just a willingness to wait, but a willingness to wait and do more things while you're waiting.

9:52Tyler Denk: Couldn't agree more. But I'm happy to jump back into your actual question around... the morning. So yeah, while I was at Morning Brew, we obviously scaled very quickly. And we became this beacon of the newsletter ecosystem and this new media wave of newsletter-first companies like Morning Brew, Axios, The Skim, The Hustle. And the great thing about newsletters is you can hit reply and get in contact with the person who wrote the newsletter. And so we would receive thousands of replies every single week to the Morning Brew inbox. And a large percentage of them were always people asking, how did you build the referral program?

10:28Tyler Denk: How did you style the newsletter? How are you inboxing an outlook? What data are you looking at? How are you growing so quickly? What is the backend infrastructure that you're using to send your emails? And these would always get forwarded to me. And obviously, I can't answer 500 emails a week. But it was enough of a signal that these people, whether they were writers, journalists, employees at companies who were sending a company newsletter, there was a gap in the market between what they were doing and what we had built at Morning Brew. And they wanted insights from us as the experts. And that funneled up to me as the person who built all of that infrastructure.

11:05Tyler Denk: I was like, wait, I know the answer to all of these questions. And it's not that we chose the right vendor. We ended up building our own solution for almost all of those things. So for me, that was the impetus of big gap in the market. What we built was super valuable. Everyone wants to build Morning Brew for X. We had already built Morning Brew. And then me and my co-founders, it's cool to build tech for an internal team of 30 employees. As an engineer, you always want to build things that millions of people touch. And so breaking out of the walls of Morning Brew and being able to build that, I think was always really attractive to us.

11:35Tyler Denk: To get your timeline right, I think Substack actually launched about 3 or 4 years before us. And so there's actually already some validation in this newsletter ecosystem that there's venture-backed interests in people wanting to fund Substack. Subsec has matured a ton, obviously. At the time, they were ripped on Twitter for... The product was terrible. The design was terrible. It just didn't work. It was very limiting. And so they raised, I think, a$65 million valuation in their Series B. I saw that headline. I saw everyone complaining on Twitter. And then I looked at what we built that morning, Bruno.

12:09Tyler Denk: I was like, this is so much more powerful than this company that's valued$65 million. And I know that is. So that was kind of the bet to take and where we took a leap there to build it. Yeah. And obviously, you built an incredible platform and a very different go-to-market and approach than Substack has taken. I think those roads have diverged pretty significantly from my perspective. And so yeah, I will say openly, I'm a happy user of DI, both for this podcast and for our dozens of newsletters. And so yeah, very appreciative of what you guys are building and so interested to see where the product is going, which we'll get into later in this episode as well.

12:50What do you guys think has been the biggest unlock for the business as you guys have grown? Brian, you've been there for a handful of years now as well. As you... And Tyler, if you want to start, Beehive is obviously not just a newsletter platform anymore. So what you guys built at Morning Brew is very different than where the business stands today? What has been that shift? I think the reality is we started with a core product that we knew extremely well. So like Ty mentioned, building out all the tech behind Morning Brew. And I think today, bar none, we have the best newsletter platform on the internet.

13:26And we did that product extremely well and got a ton of great feedback on what that is and what that does. And as we saw the success there, we started to expand outside of that to other resources that people needed with that same type of expertise, whether that's hiring external to bring those people in to help us build that or using our existing team. And what we've done really, really well is really focusing on that product market fit and understanding what our users need, what they want and hearing them. And I think the testament to Tyler and the product team is like, we take feedback very seriously and build that into our roadmap and build that into what we're doing.

14:02So we shipped incredibly fast across the board and build an incredibly solid product. So we've built that reputation in market that we're going to hit that highest bar across everything that we've built. So now as we expand these other areas like podcast or community, that is the expectation of where we'll get. So again, newsletters continually are bread and butter and will be our core. But we've expanded into these other areas that we're going to make an 11 out of 10 across the board.

14:33Tyler Denk: Yeah, no, I think that's the base of it. I think that we came in with a roadmap that was... We're not trying to be like Substack or other platforms. We know what worked at Morning Brew. And we're going to make that possible for all of our users and nailing newsletter. And then I think we've always had from day one, this DNA to ship very fast and listen to customer feedback. And so when customers can tweet at me, hey, this sucks. Can you fix it? And an hour later, I can be like, hey, we already pushed up an update. There's a lot of customer loyalty and trust that gets built up in that process. And then we've shifted from not just being a newsletter platform or a content creator ecosystem, but we're really an engine to build things to solve people's problem.

15:13Tyler Denk: And we can do that quicker than I think any other company in our industry. So I think that's brought us a great reputation and a lot of patience with our users to build out our roadmap. I think there's also some differences in this new term that we are tossing around, like the sovereign creator. who isn't dependent on a single algorithm and platform, but they can build a standalone business based on their content. And we provide the best tools in the ecosystem to be able to do that across, whether it's community or podcast or newsletter or website, we don't take a cut of revenue. So where most of the creator economy platforms have a take rate model of 10 to 15%, we take 0%.

15:53Tyler Denk: And where a lot of those other competitors, they become the destination. They want to get in between the creator and their audience to become the place where people go. Whether it's a meta, a Facebook, or a sub stack. We are actually the invisible infrastructure and tools behind these businesses. So you can build your own standalone business. And we aren't trying to seal the spotlight or intermediate between them. I think that's a philosophical difference that a lot of creators and publishers resonate with. So I think those are a few of the big things. And then I think the last one I'd call out is just the team and the people that we've been able to collect here.

16:32Tyler Denk: Product velocity in general, I think is a huge moat. And talent density is the other one. And maintaining a very high bar for excellence where we have really ambitious people who are very passionate about what we're doing and don't settle for working with people who are not giving their all has allowed us to do everything from move very quickly to lead the way in this ecosystem. some of a lot of different things that we're building. It's really helpful to hear the context from both of you, because I think it helps set the stage for how the company operates, or what is the culture? What is the strategy?

17:07How do you guys think about... And then how does that ladder into internal communications, the way that the executive team functions, etc., which we're going to get into in just a moment. So thank you for setting the stage. I'm like, what is Beehive? What is its place in the market? And how is the company thinking about its overarching plans? Tyler, I want to shift over to you for just one last moment before we get into more of Brian's story. You're a relatively public CEO, right? You've got a pretty active Twitter account. Big Desk Energy is one of the best newsletters I get in my inbox. You're dogfooding your own product through that newsletter.

17:49You're known for radical transparency. like you publish a lot of the figures of beehive more so than most, you know, kind of private startups might, might do. How has that shaped the kind of company culture that you're building around? And Brian, I'm going to get to you in a second in terms of like, well, what does that mean for your role? You know, do you have to tell Tyler to stop doing some of those things sometimes, but what does that actually look like?

18:11Tyler Denk: I actually haven't gotten in trouble much, maybe one or two times ahead of comms, but for the most part, I think it's also helpful to set the stage with like the listeners in the sense that I didn't have a large audience. I didn't come from being a creator. And I still wouldn't really consider myself creator. I'm more of a founder who's building in public and being very transparent and sharing the updates across social. I think I backed into it. When we first started this journey in 2020 is when we started building this as a side project. I had maybe 3 ,000 followers on Twitter and LinkedIn. And it was really just having a genuine excitement for what we were building and sharing like, Like, here's what this new feature is going to be.

18:51Tyler Denk: Here's how we're going to build a company. Here's how we're going to hire people. And just finding this community on then Twitter who really cared about this early zero to one startup journey. And we're basically following along and engaging. And I got really positive feedback from just sharing those early updates. And then as the company grew, it's like, okay, here's our launch day. And we got a few hundred likes on launch day. So people are like, we basically brought all of these people along on the journey with us. And that's how I backed into this building in public. It was never a strategy.

19:20Tyler Denk: It wasn't on a board deck. It wasn't anything that I did intentionally. I was just posting updates on both social channels. That eventually grew the audience. And then it became a bit more of a strategy at that point where I could post just about newsletters. And I think there's maybe 100 ,000 people in the world who really care about newsletter content and their feed all day long. But if I were to post about how we're hiring, how we run meetings, how we raise capital, it expands the team of people who care about this content to anyone who's building a business or interested in entrepreneurship.

19:52Tyler Denk: And ultimately, the name of the game is we want as many people to know about Beehive and to have a dog in the fight of at a dinner party saying like, Hey, someone talks about newsletters and like, Hey, I follow this guy, Tyler. He started this company called Beehive. You should check it out. And I guess we just want more... Someone said trying to increase the luck surface area of what you're doing. I love that concept. I think that's how my content journey took off. And then obviously, I run product. And so using the product in dogfooding, I can't trust any product lead or CEO who doesn't genuinely use their product.

20:29Tyler Denk: And I decided to launch a newsletter about 2.5 years ago. It's called Big Desk Energy. Obviously, the only thing I can really write about is the behind the scenes of the company makes it really easy. Because whether we had an interesting meeting or a big launch, I can just write from my POV, what that was like behind the scenes. I share the tips and strategies and tactics of raising capital and scaling the company. And I've become a much better CEO because of it, because I am a power user. I can talk directly to the engineers and the product team. And yeah, it's been huge. So that's what it's been like through my lens of creating more content was never intentional, but backed into it.

21:09Tyler Denk: And it's been super helpful. It also seems like you use that newsletter as a bit of an outlet for reflection, which I appreciate because at least it comes across as very candid and straight to the point. I don't do it solely because of this, but the second and third order effects of the amount of people who read the newsletter who recommend us to their friend or to their boss or whatever, we get a lot of business from people reading the newsletter. One of our largest enterprise users is Time. And that deal came about because their CTO randomly one day somehow stumbled into Big Desk Energy, signed up, read it for like 6 months.

21:41Tyler Denk: And then when they were up for renewal on their contract, they were like, Hey, I really like this Tyler guy and his company Beehive that he's building. We should give them a look. And it ended up being one of our largest enterprise deals. So putting your ideas out there on the internet, I think remains undefeated. And it's worked really well for us. I talk about nurturing a client without knowing that you're really nurturing them. That's the best way to do it. Brian, how has that shaped? How has Tyler's approach to building Beehive and obviously came naturally in terms of content strategy? How has that shaped some of your thinking or the way that you're working with Tyler today?

22:16I've always valued transparency. And I think data is power and allows us to all row in the same direction when we're thinking about what we're doing as a company. And if I'm not clear on what Tyler is thinking about from a direction standpoint, how am I going to make those decisions about what I should be working on? So that ladders down to everyone in the company. And I think Tyler's done an incredible job with this, where at any given point, anyone can see our core metrics or our KPIs or rocks. They can see where we're pacing against those and have clear visibility into how we're doing as a business.

22:51So from an operational standpoint, I think it just limits the back and forth of... Oh, like, am I reading between the lines of what this means? What does this mean? Like, there's never really a question. It's just like, we're all adults. Let's talk about it in transparency, land where we need to be, and then go attack the problem and solve it. So from an operational standpoint, I personally really love it and try to adopt that as well from both just like a decision-making standpoint, sharing why we landed there, context sharing, all these things just help us move faster because there's less discussion of like, well, what does this mean?

23:23And it's like, hey, I'm just going to tell you what it means and move on. So I personally really appreciate that. And it works great because then I don't have to question what Tyler is thinking. I don't need to relay what Tyler is saying because he just says it directly to the company. So I think that's super, super valuable and allows us to move very quickly. And you guys obviously have a background working together at Morning Brew. And then before you moved into this chief of staff position, obviously, while you were in RevOps, when you moved into your chief of staff role, was there a little bit of a reset that needed to happen in terms of like reestablishing that trust, communication patterns, the relationship generally?

23:58Or did it feel like a more natural evolution and you just kind of like the title change, but the relationship has basically been what it was before? Like was there a moment there? There definitely was like some recalibration of like, we both have our standard working process. And I think I've been in seat now for about three months. So it takes time as we work through projects to build the habit of like, let me loop in Tyler for this. Or maybe there's things that Tyler was leaning on Dan, his old CEO, or his old chief of staff for that he can now tap me in. Or maybe he's leveraging AI for something instead of going to me, which is totally fine.

24:34But really just trying to work on habits to make sure that I'm supporting him in the best way that I can. So it kind of has been like, from my understanding, it's like we have this baseline trust. And then just building those habits to work together but to see where I can lean in more to help give him time back in his day and really support him the best that I can. So that's kind of how I've approached it.

24:54Tyler Denk: Yeah. Brian's being a bit more generous. He also messaged me. He's like, I kind of feel like I'm not really being your chief of staff right now. This is like maybe a few weeks into the job, which he was like, totally right. The context there is like, I had a previous chief of staff who moved into the COO role. And very early days, he was like an assistant chief of staff, like doing everything that you would typically expect of a chief of staff. And then matured with the business, took on more responsibility. We had less touch points. And he was already shifting into the COO role, where I got used to not having a chief of staff in a pure chief of staff type position.

25:28Tyler Denk: And it's something about my personality too. I don't have... Everyone always asks me to loop in with my EA or whatever. I don't have... I book all my flights and everything myself. I schedule everything myself. So I've always been very independent. And it's a learned behavior for me to depend on someone else and start sharing that context. So yeah, I think we went through a month or so adjustment period of trying to just drop all the context. So Brian's a part of all of those conversations and can start operating on his own. And then we recently just implemented... I'm on the West Coast. He's on the East Coast.

26:03Tyler Denk: So when I go to the gym in the morning around 7am, we've just blocked off that time. And even though it's only a 10 to 15-minute drive to the gym, I call him every morning, Monday through Friday, sometimes on weekends. And that's just our brain dump of what are we going to prioritize today. We're also in chats all day long. But I think the phone call has helped a lot just at a level set of what are you prioritizing? What am I prioritizing? I think it's a really important point because even 15 minutes, 5 or 6 days of the week can make a huge difference and can be more valuable than, say, spending an hour together on a Wednesday.

26:39And so I think I talk to lots of chiefs of staff, right? And the normal cadence, the normal business rhythm is, yeah, I've got a once a week meeting with my principal and it's almost never enough. Or it's not quite the right forum to have a very active dialogue about the things going on that week or coming up in that quarter. As you guys have matured, Brian, as you've matured into this role, and Tyler, as you've gotten more comfortable working with Brian as a chief of staff, what are the things that you're starting to delegate to Brian that wouldn't have made sense, say, to an executive assistant if you had one?

27:17And Brian, where do you see yourself fitting in amongst the rest of the executive team?

27:22Tyler Denk: I guess like a high level. And I think there's... And you probably know best, Scott, in terms of how different CEOs view the chief of staff role. Both Brian and my previous two chief of staffs, I never viewed them even close to an EA. It's never like, take things off my plate or do scheduling or be an assistant. It's almost like being equal to me where you're a second brain and And anything that I'm... Any meeting that I'm running, you should be able to sub in if you need to. Any big decision, if I'm not around to make it, you should have the autonomy to make that decision because you have full context of everything that I'm doing.

27:56Tyler Denk: And I think that's a split that I've seen. Some people do view their chief of staff as an assistant. And it really is a glorified EA. And then others view it as a second CEO, essentially. And I think for all three of my chief of staffs, I viewed it the latter bucket. I'm just going to say quickly, I'm glad that you said it so I didn't have to. But thank you for defining the chief of staff that way, because that's absolutely the way that it should be. And I think that the best in class chiefs of staff that we see working with some of the top startups and enterprises out there are doing exactly that.

28:28They're shadowing the CEO for a little while and then effectively doubling his or her capacity by being able to stand in the rooms that they physically can't. Because your capacity is limited, right? And I think the challenge of a CEO today is like the complexity of businesses and the landscape that we're operating in and the speed of which we're changing is way too much for one person to handle at the helm. And so a chief of staff, you know, can help operationalize a lot of the things that like you're seeing coming around the corner, but can't quite get to everybody in the room to go, you know, make sure that that happens.

29:04Yeah, for sure. And I think too, like with everything I've done, I've always taken the approach of just being very curious and nothing is ever below me. And I think that's the best way to learn. So as I've gotten up to speed, I spend time reading through threads that Tyler's on. And maybe I'm not associated with the project or not super heavily involved. But to Tyler's point, I want to have the context. And in the case where he can't step in or he isn't there, I can come in and have that full context. So really trying to stay up to speed across everything and just being genuinely curious and asking questions and getting involved.

29:37But yeah, so like a couple of the high level things and just like general, like weekly meetings with our leadership team. So we have a weekly meeting run every Wednesday, two hours we spend with the leadership team. And it's everything from getting team lead updates from all of our team leads to organizing the agenda to setting the discussion points based on all the different things that are going on in the business. Sure, Tyler has a good pulse of it, but he's also doing 17 other things. So for me to be able to collaborate all of that, put it in one place, get in front of the team for us to run an effective meeting.

30:08And it's everything after that too, right? Like we discuss a ton. And it's so easy for all this to just kind of get spread out and get lost. We're a fully run out team. Like no one's really like on your back. So I'm there to help follow through on all those things. And then there's everything to like larger business rhythms. So like our rock functions and KPIs from a quarterly perspective, tracking against those, making sure that we have proper guidelines, visibility, reporting, and all those things against those goals. And then there's more tactical things. So we've been working through some pricing and packaging updates and understanding what we want to do there later this year.

30:45So that's something where Tyler is heavily involved, but I was able to step in and help push that initiative forward, work with our CMO. So to your question around how I see myself with the rest of the executive team, I see myself as a branch to them and a support system as well. And depending on the week, the quarter, other projects that are going on, maybe I spend a lot more time with our CMO on pricing and packaging this quarter. But then next quarter, it's something with the engineering team or product team where there's a gap. So trying to stay and build those relationships with them so that they can give me feedback on what's working, what's not.

31:19They can share insights into how Tyler can be a better CEO and I can pass that back to him. I think as a whole, trying to just build a great relationship with everyone on our executive team so that they can trust me with any of the problems that they have or are seeing in their org and try to find that solution.

31:36Tyler Denk: So hopefully that's a good high level of view. Two things I'd expand on there is I view Brian as obviously an equal in the leadership team. And he's really the glue in between everyone in that meeting and in that group. So he's the one tying everything together, making sure everything runs properly and that everyone's being followed up with what they need to do. And then the other thing is... There's huge value in the chief of staff role. He has so much context across the business. He can be deployed to solve different problems across different teams. And that being very fungible. So we've recently made a few changes to the ad network team.

32:12Tyler Denk: There's different things that we want to change and improve with the ad network. And he is more or less just deployed into that team as if he is running it to solve all of the problems, to lead a bit of a turnaround effort and get the right people in seat, knowing that that's not a forever thing, but that's maybe a six to eight week mission where he can do, is fully trusted to do the best job there, but then return back to chief of staff until another problem arises elsewhere and then having to be deployed there. But just being deployable, I guess, and knowing that he could jump onto any team and get to the root problem of anything and then figure out ways to solve it.

32:46Tyler Denk: I think that is what makes a pretty exceptional chief of staff. I tend to agree with that. And I think it's a fairly different way of framing a chief of staff role than the way that we would look at the position, say, in the White House or in military. But when we're talking about rapidly growing private companies, even large enterprises to a degree, you kind of do need someone occasionally that can swoop into problems with full context and a direct line to the CEO or other members of the leadership team. team not just to be the eyes and ears on the ground but but also to drive the core mission and yeah i think it's important to you that that you said that because a lot of people look at chief of staff roles and say it shouldn't quite be like you know maybe that's too close to biz ops but but i think a good chief of staff very often is generalist and those generalists can find their way into different problems and be at least 80 to 90 good enough to go solve them and so i i would stick by that that part of the definition that that you just framed up I think a good chief of staff shouldn't be put in any box.

33:50Tyler Denk: I think a good chief of staff could be whatever the problem is. It doesn't matter if it looks too much like finance or too much like sales or too much like engineering. They should be able to jump into any team and be able to execute and maybe not jump onto the engineering team and build architectural decisions and actually code things. But at least be able to talk to the people on the team to get to the root problem, to have a solution of how to fix things. I think any chief of staff who would push back on like, Like, oh, I can't go into the engineering or because I don't have experience there.

34:20Tyler Denk: So I can't provide value. Or I don't want to do that because I don't... I'm not really interested in finance. That would be a red flag to me. I think the can-do attitude and the willingness to do the work because you have the contacts and you are the glue between the leadership team. So you can actually pull the levers to get things done. That is what I think would make the best Chief of Staff. Yeah. I do the role very operational. And my job is not to come in and point out problems. It's to help solve those and bring solutions. And a lot of the difficulties there is building relationships with the people who are actually doing the day-to-day work.

34:53So a lot of this stuff that I've been doing over the past couple months is... I've been at Beehive for 3 years. So I have a relationship with a lot of people. But maybe they don't trust me fully or maybe they haven't worked with me a ton yet. So it's like taking the time to build these relationships with the team leads so that they know that I'm confident. They know what I'm doing. they build trust with me so that they can come to me with problems. And I think the best way to do that is showing up when you say you will. It's the easiest thing to do, but most people don't do it. But if you say you're going to do something, see it through, communicate it clearly and show up.

35:28And if you do that consistently, you'll build that trust in that relationship with team leads across the board so that you can work with them effectively. Because the problem gets so much harder when you're dealing with people outside of just the actual problem of the business.

35:40Tyler Denk: What Brian calls out there is really interesting is the pushback that you can receive from a leadership team or bring you on a chief of staff. Because I've seen it a few times. We had a very early chief of staff who moved into a COO role. And then we didn't have a chief of staff for a while. And when I presented to the leadership team, I have someone who I want to hire as chief of staff. There's always a lot of pushback of who is this role that reports to no one but goes into different teams and tries to solve problems. But the other way of that is like, are they getting in the way? Just like the way that they ladder up only to the CEO, they're kind of like this floater that certain teams and certain team leads can feel defensive around their team and the responsibilities.

36:19Tyler Denk: So I think it's worth calling out the relationship thing that Brian mentioned, because we did get pushback internally for hiring a chief of staff prior to Brian. And that was very quickly proven to be the right decision, which is bring on the chief of staff. And we haven't gotten that pushback since. But I think it takes the fact that we've hired two incredible chief of staffs that built those relationships and prove that they're willing to do the work to build those relationships. Yeah, I know that. That's interesting. And you're both right that it goes well beyond the executive team. Chief of staff kind of needs to operate both at the ground level, kind of across the ranks of folks executing day to day and at the strategic level, right, where the kind of bigger decisions are being made.

36:57And those relationships don't come out of thin air. in my chief of staff role, what I found to be most effective really was just showing people that you could unblock the thing that they were blocked on. Sometimes having the capability to go straight back to the CEO and say, Hey, look, this team is struggling with X, Y, and Z. Engineering is not delivering this to product. So the product roadmap is all screwed. let's unblock that um that becomes a really effective way of showing and building trust with that person when you need to go call on the favor or when you show up into that meeting you know a couple weeks later and they're wondering why you're there uh all of a sudden it's a smile not a frown but that also takes time and so i think probably and i'm i'm curious what was the previous chief of staff also an internal hire tyler or was that an external hire kind of brought in external.

37:52Was that a more difficult onboarding experience in terms of building that trust, establishing those relationships versus... Well, Brian and you have worked together in the past, but Brian's also been with Beehive for a couple of years and still had the opportunities both to get to know the business and some of the people around various teams.

38:09Tyler Denk: So our previous chief of staff is now our COO. He invested in our seed round. And so he actually We had seen an ISN monthly investor updates that are very detailed. So he had actually read every single update every month, actually jumped out as one of the few who responded every month with willing to make introductions and help out and rubber duck different types of problems. So he was always a very active angel investor and eventually got fed up with his old job in big tech and expressed interest in wanting to join us. So I'd say that he also had a good amount of context about the business. and we had a previous friendly relationship through like an investor and like friends of friends.

38:47Tyler Denk: So the ramp up there wasn't too difficult either. But I think he also, like Brian, has like a very high EQ. And so he knew that he was kind of coming into like a new territory where people may be defensive. And so I think he over-indexed in building those relationships and going above and beyond to unblock the block. Like he knew that he needed to do that for this role to be successful. And he over-indexed on making that happen. and everyone ended up appreciating everything that he did. How do you guys think about the division between strategy work at the executive level and execution with the rest of the team?

39:22Brian, we talked about you kind of swooping into problems. Are you participating in like the strategy and direction of the organization or are you more setting like operational cadence and the strategic planning like frameworks, but not necessarily the decision-making in kind of what that strategy is going to be? I think it's a mix. And we at the HUD do it as a team. Tyler, as CEO, leads the function there. But we really work as an executive team across a lot of the strategy and what we're doing and aligning there so that there's alignment from the top down as we communicate that out. So yeah, I'd say we work across everything from high-level strategy for long-term planning, quarterly planning, etc.

40:04But then also tactically getting into the day-to-day or week-over-week and tracking those metrics and operationally actually hitting those goals and expectations. So we kind of hit on that across all levels. My exposure to that really depends on where needs the most help. So like Tyler mentioned with the ad network currently, I was spending more time there than I was in the past. And that may be for the next 8, 9, 10 weeks, but then that may pivot to something else. So you only have so much time in a week, so you We need to dedicate where those problems are and attack those. But yeah, it's across the whole field.

40:39So it's strategy down to like the day-to-day tactical work. Tyler, where does your kind of background from Morning Brew and just your general opinion on how kind of the media landscape is being reshaped with lots of creators, trying hopefully to move away from some of the algorithm-driven news feeds and such. Where does your view of the world take shape? And how does that translate into either directives to Brian or the rest of the team?

41:11Tyler Denk: Yeah, I think I view most of it through a product lens. Because I lead product, and that's what I'm most passionate about. And as a tech company, I think the product leads the way for execution down funnel of that. I mostly think through the lens of what product do we need to build to support our features of what the creator economy and media ecosystem looks like moving forward. And how are we best positioned to serve where the puck is going? I think we are still so early in the creator economy. I tweeted the other week. I think that the creator economy is the future of media. We're seeing it from large media.

41:48Tyler Denk: Take a further back stance. There's a world where you only watch six TV stations. And that was the only way, whether it was the local paper and these few TV stations or where you consume news. And all information was funneled through a few gatekeepers. The internet totally broke that down with blogs and then social media, the ability to consume and find information from a bunch of different people who don't have all of this power. And then we're just seeing now these business models being created, whether there are successful newsletters and media companies built on Beehive, whether they're YouTubers, whether they have a massive podcast.

42:23Tyler Denk: There's real economics of being able to be a subject matter expert or entertain people and create information and content. And I think that our platform has had a bit to do with the lowering the barriers of entry for anyone to get started. The amount of case studies that we have of people who started a newsletter as a side project that turned into a few hundred dollars a week, that turned into a few thousand dollars a week, that is now their full-time job and they've hired a team and they're building a business and they're launching a podcast and they're creating more and more content. I think those are the outcomes that we want to facilitate.

42:58Tyler Denk: And I think we're in an incredible position to do it. One, because I think we have a very clear vision of what this future looks like and what product best serves it. Two, because I think most of our competitors are either not moving at the same speed as us or have a very different philosophical take of what it means to be a platform, whether it means intermediating between them and their audience, whether it means taking a cut of revenue, whether it means they gain more power and control in the relationship, where I actually think all of the power and control should belong to the content creator.

43:28Tyler Denk: And so I think we are actually on the right side of not taking a take rate, putting the brand and creator first, and building tools as quickly as possible, irrespective of our initial roadmap, but over-indexing on what the customers and users want and what this media ecosystem needs to succeed. And so I think that's why I'm so bullish about the business and what we're building. I think what's also interesting is that you guys are operating both between individual content creators, but also large legacy media houses, like Time as the example. How does that shift your thinking around strategy in terms of managing both of those ICPs?

44:09It's a great question.

44:10Tyler Denk: One of my initial theses was when I was at Morning Brew, we were obviously using the best of the best enterprise ESP that costs hundreds of thousands of dollars. And we built all of this custom tech. And we were built fully for an enterprise newsletter content org. Yet, these tiny hobbyists who had 17 readers who were sending a monthly update to their best friends wanted the same thing that Morning Brew wanted. And I think that became very clear to me is that no matter how big you or small you are, you always just want best in class. And so our philosophy from day one has always been to build enterprise-level software and quote-unquote democratize that at a price point that consumers can tap into.

44:54Tyler Denk: And so when you look at our feature suite, whether it's our automation suite, or dynamic content, or API, or webhooks, it's a very enterprise-level capability that you can get for free to start off or for$49 a month on the low end. And so I think that thesis rings true. Yes, we are building for TechCrunch and time and all of their sophisticated use cases of what they need. But I think the hobbyist and the individual creator will benefit from having access to those same tools at a price point that they can afford. And so I think there's a pretty strong overlap between what both of them want is the real answer.

45:29Tyler Denk: The harder part is marketing. How do you market when we are very... Let's say I've said the word creator on this 15 times, but like that, like no one at TechCrunch or Time thinks of themselves as a creator. And so when you listen to this podcast, you're like, is this be a product for me? And then vice versa, if I were to over-index on Time and TechCrunch and Newsweek and Sinclair and all these massive organizations that are using us, if you are a content creator writing about sports or whatever, like you feel like that platform is not for you. So I think it's like a messaging and positioning thing that's actually harder on the product side.

46:03Tyler Denk: And like what I own, it's actually fairly straightforward. Brian, where do you participate in terms of taking Tyler's vision? And he paints a very vivid picture of what the landscape is, where Beehive's Place is in it, and where you guys are headed. How do you take that vision? And what is your role in translating that to the rest of the team? Tyler's obviously very involved in product, but how do you make sure marketing has the same story and is not walking away with a different version that comes out of that executive room? I think honestly, because of the transparency and the way that we operate at Beehive, Tyler dictates a lot of that.

46:40And I actually don't need to step in a lot. He makes it super clear for the team of what we're doing. And having that transparency from the leadership meeting down to the weekly all hands makes that message really clear to people. So although I may not be doing like, hey, following up on this or pushing that narrative, people tend to understand that from Tyler directly. but because I have all the context from everything that's happening, as there's questions that come up, I can jump in and reiterate, Hey, this is the main goal or Hey, I hear you. I hear this confusion about this. Let me clarify that a little bit more.

47:12So I think it's more just reiterating and supporting the narrative than actually like pushing it forward because of how we operate with a lot of transparency. You guys are making it sound easy, but this is obviously one of the biggest challenges for many organizations, large and small is saying one thing in the room and making sure that that's translated across the rest of the teams in the same way. Totally.

47:35Tyler Denk: I mean, Brian's already hammered the transparency angle. I think it's bizarre that companies operate any differently. I worked at Morning Brew. I worked at YouTube, which obviously didn't operate that way. But that was a short stint. And this is all I know. But it doesn't make sense to have this passion or urgency to do something without the team knowing why there is that urgency to do any one thing. And it comes from just giving access and transparency to the numbers from revenue to cost to concerns. Like I share our board deck every quarter with the entire company. And it's like very, very transparent around, here's like the 10 things that are pissing me off and keeping me up at night.

48:13Tyler Denk: And like they're direct, like they call out teams and processes that people are tied to. But I actually think it's better that people hear and see for themselves that I have concerns around this function or this team's performance. than thinking that everything is great. And so I think it'd be harder if we didn't do that from the get-go and changing to a culture of making everything radically transparent. But because from day one, I shared how much money we're making, how much we're spending, what's not working, and what needs to be improved. I think that's just been the normal operating cadence of the business and what people have come to expect.

48:44And it makes a ton of sense. I think because you're a product person, you're probably also able to quell some of the impulses of like next shiny object. And, you know, for many CEOs that might consider themselves product people, but are not really, it's always like throwing paint at a wall, which, you know, can send the teams down a rabbit hole and feeling like there's never quite a straight direction. And, you know, I hear lots of stories, of course, of chiefs of staff and having to step into like reframe, reposition, or stop the CEO before they can get to the all hands and say something new.

49:19That doesn't seem to be the case here, which is great. But yeah, curious, just Brian, if that ever comes up, what do you find yourself having to do? It hasn't happened a lot, but to go back to transparency and also just feedback, we are pretty direct. Tyler mentioned earlier on this, I didn't feel like I was involved in certain things that I could have been. And I could have sat there and said nothing, gotten frustrated, whatever. But I just directly told him. So if there's anything that is coming up that's misaligned or there's confusion, I'll just say it directly. And I don't need to be dodgy about it.

49:55I don't need to be worried about Tyler getting upset. We've created a culture where you can give that feedback directly with the best intent. And he'll take that and move on. So when these things do come up, I just approach it directly. There's no reason to try to go around it. So that's how we've addressed it so far. Tyler, Brian, I want to thank you guys so much for joining us today. Do you have any parting words for our audience? Brian, what would you share for an incoming chief of staff, getting his or her feet wet in the role for the first time? I think the big themes are stay curious and be patient.

50:26Don't be afraid to get your hands dirty, be involved, ask questions, and consistently work with the team to build those good relationships. And if you consistently keep your head down and work hard and ultimately show results, the payout and the benefits will come in the end. So just consistently showing up is, I think, the best way to really hit at home as a chief of staff. Tyler, it was really nice having you here as well. We don't always get the chance to have both CEO and chief of staff together. So thank you for the time. For the CEOs, founders listening, what advice would you give now that you're on your third chief of staff, either in hiring a chief of staff or working with the chief of staff?

51:05What has made the relationship successful for you?

51:07Tyler Denk: It's also worth calling out the third chief of staff. All three have been successful, right? I think when some people hear that, they're like, Oh, you've tried 3 of them. We had a chief of staff. She moved to COO. Then we moved her to chief customer officer. We had our second chief of staff. He moved into COO. And then we've just moved Brian into the position 3 months ago. And as you can tell from this conversation, going very well. Yeah, I think maybe what I hit on earlier, understanding the difference between an EA and a chief of staff and looking for someone who really can be a second you, I think it really unlocks a ton of benefits.

51:40Tyler Denk: And then looking, I mean, if you've listened to this much of the episode, looking for someone like Brian, whatever, whenever you can find someone like Brian and like those traits, like that's what I think a killer chief of staff is. And so being on the lookout for that. Well, thank you guys so much. And I will include some links to Big Desk Energy and the Beehive links as well below, including the new community product. So thank you guys for sharing. I appreciate the stories. Thanks again to Tyler Dank and Brian Schneider from Beehive for joining us today. A few things that stayed with me from this conversation.

52:11One was Tyler's clean articulation of the difference between a chief of staff and an executive assistant, which frankly every principal should hear. Brian's point that showing up when you say you will is the simplest and most underrated way to build trust across a leadership team. And also the framing of the chief of staff as deployable, someone who can be dropped into any problem with full context and also the authority to move. If you're actively in the role and want to connect with a global community of chiefs of staff operating at this level, Chief of Staff Network's pro membership is where that happens.

52:44And if you're working towards landing your first chief of staff role, the Chief of Staff Launchpad gives you the skills, frameworks, and the network to get there. Both links are in the show notes below. Thanks again for listening. We'll see you next week.

53:15Outro Music