Community-Driven Growth with Sam Jacobs

1,000 Stories


Joe Mills: What are the unique experiences that drive business leaders to keep growing, and how can the lessons learned from those stories enable others to do the same? I’m Joe Mills.

Reid Morris: And I’m Reid Morris. 

Joe Mills: And together we’re investigating who it takes and the tools to use to build companies and culture. Then we’re sharing those stories with you. This is 1,000 Stories, an original show from Element Three. 

Reid Morris: Okay, Joe, so next guest is, is a really exciting one in Sam Jacobs. Uh, an individual who, like you, has had a career in like revenue ownership, but he’s had a lot of different roles over, over his time and now 

Joe Mills: He’s, he’s like three X me.

Reid Morris: He’s future you, right? Yeah. Um, but now, you know, has, has founded a company, uh, that he’s been running for the last seven or so years, but, Just based on the different touchpoints over his history. I think there’s a lot of stuff to dive into. Where’s your head at as to where you want to go with Sam? 

Joe Mills: Uh, there’s, there’s probably two things that are exciting for me with Sam. One is that he has this, that we really identify with, and I don’t know that everybody identifies with that. You can have a really successfully lucrative career and build it in a way that is compassionate and people first and culture centered. 

Reid Morris: Mm-hmm. 

Joe Mills: And so that’s his viewpoint. That’s the book he just wrote. That’s a Wall Street Journal bestseller. Um, I’m really excited to dive into his, his perception on that and get some, uh, just, just like his viewpoints on it. 

Reid Morris: Mm-hmm. 

Joe Mills: In more detail. Mm-hmm. And then, so that’s one. And the, the second one is he went through taking on a significant amount of funding for pavilion. So he built the company, and I wanna say just about halfway through, so about seven years, I think it was about three, three and a half years ago, he took on a couple hundred million dollars in funding to help it grow bigger. And I want to know what that was like for him going from, you know, starting himself.

Having all the control of the decision making, he’s setting the goals to, I’ve now taken on significant amounts of funding and I have essentially, I’ve taken on bosses, right? Mm-hmm. Um, and they have expectations and they have probably different viewpoints on like what growth, like what needs to be done for growth.

Mm-hmm. So I’m just interested in unpacking with him what his experience has been like in that way. What’s been good, what’s been hard? Um, Those, those two things are where my head’s at. 

Reid Morris: It’s really interesting because you know, as Element three, two, somewhat qualifiers for the people that we frequently work with are companies who care about culture, people purpose, right? And then these big inflection points in their organizations. 

But I feel like that’s, Something that we haven’t really tapped into in great depth on the podcast yet of 

Joe Mills: Yeah. 

Reid Morris: How did those things actually play together? Right? 

Joe Mills: Yeah. 

Reid Morris: So as somebody who has built this culture for this organization, how is he managing that through something like taking out a bunch of funding, all the big shifts of the new players involved. So they think that could be a, a really interesting story to dive into. They could pay dividends in lots of other people’s business cases. 

Joe Mills: Yeah, and I think the trope is culture and money are on opposite ends of the spectrum. That you can be really culture focused, but when you take on a lot of funding or take on private equity capital or do something where you take in this influx of money, the growth trajectory changes and now you have to forget about culture.

And I think that that’s likely not true, but it is, I think, the energy that you hear around it. 

Reid Morris: Mm-hmm. 

Joe Mills: And so I’m very interested in just like his experience, his perspective. Moments where he’s felt like that’s happened. The moments where he’s felt like it hasn’t happened. 

Reid Morris: Mm-hmm. How he’s mitigated all that.

Joe Mills: How he’s mitigated it. Exactly. They should be really interested. If it’s not true at all, maybe he is like, nah, it’s not how we’ve experienced it at all. Mm-hmm. He’s interested in all of that. 

Reid Morris: Looking forward to it. 

Joe Mills: All right. So Sam, welcome to 1000 Stories, man. We’re really excited to have Jann. 

Sam Jacobs: Excited to be here.

Joe Mills: As a quick overview, and I would love for you to add how you describe what you do and what you’re here, what you’re here to work on, on a day-to-day basis, but you’re a five-time executive at, um, various high growth startups. You obviously are the founder and c e o of Pavilion, which is an incredibly successful community, really member driven, and I’ve been reading your Wall Street Journal bestselling book that you are now an author of. So you got a lot of stuff in the fireman. When somebody asks you the quintessential American question of what do you do, how, how do you respond to that question?

Sam Jacobs: I, I normally, I just say I run Pavilion. 

Joe Mills: Okay. 

Sam Jacobs: So I should, I should be like, I’m a Wall Street Journal bestselling author and you know, dog dad to three dogs and all that other stuff. But mainly I say, uh, yeah, I’m founder and c e o of Pavilion. Pavilion is the leading community for high growth revenue executives and CEOs. And the purpose of the community is to help people really lead more meaningful careers, create more stability and security and predictability in their career, and help them achieve things that they want to achieve in these specific roles in sales and marketing leadership roles, and as founders and CEOs to help them get where they want to go. Mm-hmm. That’s what we do. 

Joe Mills: Yeah. And one of the things that really stood out to me, so I’m reading your book, Really close to finishing and up I’m in like past the unit economics and pieces of that. So we’ve gotten into some of the tactical things, which really are enjoyable for me in, in my role. I don’t do a ton of things concerning with unit economics, but as a person who leads sales here, I really affect them a lot.

And so it’s really, it was really interesting for me just to dive into that end. But the first thing that stood out to me is you talked about something in one of the early chapters that you always felt growing up, that you had this like, Sense of sense of being able to accomplish great things. And that really resonated with me a lot.

Like I’ve almost always had the same sense of like, there’s something out there that like. I’m supposed to be doing or like have a thing to make an impact on, and I’m made to do something special. Um, which is a weird thing to, I’ve never really said it out loud before because I think it can sound very strange.

Sam Jacobs: It can sound, uh, it can sound egotistical. There’s this moment in my life, right? And I talk about it in the book where I fired my therapist and I remember distinctly and I have a coach. So it’s not about firing an external. Perspective to help you develop in your life. It was about this particular relationship that was problematic for me.

Mm-hmm. And I remember saying exactly what you just said, Joe, and he said basically, I, I’m paraphrasing, but like, well, let’s figure out what happened wrong in your childhood to make you think that you’re special because you’re not. Mm-hmm. Uh, you know, not, like, not that you’re a bad thing, you’re just, you know, like, Hey, the math of life, you’re probably about average.

That’s kind of how average works. And your need to be different or to be special is probably a personality quirk slash flaw. Mm-hmm. More than it is any commentary on what your capabilities are. And then if you read like, um, I don’t know if you know this Enneagram thing.

Joe Mills: That’s actually where my head went. I was gonna ask you if you’re into it at all. 

Sam Jacobs: Well, I’m a, what am I, a classic for? You know, on the four. 

Joe Mills: What you just said made me think. I, I also identify as a four, so I, 

Sam Jacobs: That sucks. 

Joe Mills: I was like, that. That sounds so familiar, man. 

Sam Jacobs: And it’s like, oh yeah, you know, you got all these problems, you weren’t loved, you know, so therefore you think you need to be special and you need attention.

And I’m like, yeah, I guess. But also I think it’s the sense of like, You feel like you have a unique perspective on the world and you don’t want to fade into oblivion, and you want to feel like whatever it was that was possible for you and yourself, that you achieved it. The point of the book, by the way, is like, hey, nurture that.

Mm-hmm. That’s not a flaw. That’s okay. Like let’s figure out how to, let’s figure out what is the way to actualize that. That’s kind of one of the points of the book. Not like, wow, you’re really messed up. You know? Read this, uh, personality. Test to tell you, well, all the things you gotta fix because you think you’re different and you ain’t different.

Joe Mills: Did you, um, have you dove in at all to the Enneagram since, since you sort of, since you referenced it, are, have you, have you gotten into it at all? 

Sam Jacobs: Not like super into it, cuz I know there’s people that go in like retreats and they like deeply study these archetypes and all I know is that I read the description of four and I’m like, yeah, it sounds like me.

Joe Mills: Yeah. There’s a. We had a, a guest on the show, his name is Chip Knight. He was one of our earlier episodes, and him and his company do executive and team coaching, and they will use it as one of their thinking models. And he sort of pointed me towards some of the underlying motivational questions that a, like, try to figure out like, well, what are you really shooting for here? What’s your, what makes you act in particular moments? And it’s been very interesting, just like the depth of research and depth of. Self discovery it takes, personally, I appreciate it a lot because I feel like Disk, Myers-Briggs, pi, all these things, like you take a test, you answer questions, it spits out a, an answer to you.

And I appreciate that. The anagram is much more like discover what your motivations are, how you act, why you act that way. And it can like, I mean for all I know, I might 20 years from now might be like, oh, that was not the real motivation. I’m actually an eight like. Is this a sort of like, 

Sam Jacobs: I love that for people that are listening that might not know anything about Enneagram, they have no idea what we’re talking about.

Joe Mills: That’s true. I should, we’ve actually probably touched on it up on our show that if they’re all, oh, maybe they listeners, they, some idea Listeners. I was gonna ask you like, one of the, the shifts I felt like I saw you make in the book is this sense of you were pursuant of money and monetary reward to go on trips, to buy things to like, you know, Give your wife a great thing.

It was sort of all this like accumulation and then at some point it like flips and you, you shift to like, oh, I found my purpose and my purpose is what pavilion has grown into. It’s allowing people the opportunity to make the most of their lives in this situation professionally. Um, I’m curious if you could tell some of the story about like what made that flip happen. And if it was like an a, like a moment, like, oh, I get it. Or if it was like a process that you went through that helped you discover that. 

Sam Jacobs: Yeah, I guess it was a process. You know, I mean, it, you know what it was, it was covid that was like, hmm, really the catalyst because I was in my apartment building, uh, during Covid.

I just remember this real. Again, everybody that talks about covid has always, I know that there were people that were impacted. I know that PE people died. I got it twice. My wife almost died. So I don’t mean any of this to be dismissive or insensitive, however I remember cuz part of like, my issues are that are comparison and that’s that’s so true in the modern world.

And I live in a city where you are constantly being reminded how much and how little you have every moment and every day. And I remember this feeling because I was, I stayed in the city all during Covid and I was the only person on my floor actually in my apartment building. It was completely, in fact, one of the lights went out.

It was spooky, but in a weird way. In a good way. And it was me and two dogs, neither of whom are alive today. So it was, these are three new dogs in my apartment right now that I live with, and it was a sense of liberation. That’s where I’m getting, it was a sense of liberation. It was a sense of the business is profitable, so like there’s no existential risk to the business.

And I don’t need to be anywhere. I don’t need to compete with anybody. Nobody’s going anywhere. The wealthiest people in the world, the most successful people in the world, they’re stuck at home just like me and the sense of competition had subsided. It was just this really peaceful feeling of like, all I need to do is focus on these other people and everything else will take care of itself.

And I wish I could say that. All of that means that I’ve lost my taste for nice things. Or I’ve lost my taste for all of the accoutrement of success. That’s not true. Unfortunately, like one of the reasons I work for myself is because I have a preference on a lot of things on how to run a company and what kind of food I want and how I like to travel.

Yep. So I am a four, right? I wanna be different and feel the finer things in life. And I do, I feel, and my point of view on most things is like, whatever you like is totally fine as long as you can afford it. Um, like never apologize for your taste. Yeah. But the point is like, it was the sense of like this, this desire for all this stuff coupled with like a lack of ability to have it, like realistically meaning I couldn’t afford it.

Coupled with like this sense of like, all of that was under somebody else’s control. Meaning like the company that I work for or my boss and whether or not that person happened to like me, or whether they thought I was the right sales leader at that moment or at that time. And if I wasn’t, then my job was on the line.

And it was the sense of like, almost like the trash compactor in Star Wars, you just felt like the walls were squeezing in on both sides and you didn’t really have a clear way out of the situation. Mm-hmm. And for me that the switch began where the book began, which is getting fired from the Muse back in 2017 and really beginning to be like, okay, I’m gonna design my life the way that I want it to be.

And even with Be Havac, which was the last place that I worked full-time in 2018. That company’s still around. They’re doing great. You know what? It just wasn’t a good fit for me. But even that job was different than the other jobs because I negotiated so well for it that I knew that I was protected. I knew that like if I got fired, there would be severance, and if this happened, there would be something else.

And so even then, the pressure, and it was a fun job. I got to go to London all the time, and I got to go to Singapore and Sydney. And meet with Macquarie and try to close that deal. So it was a sense of what shifting from lack of control to control. And [00:14:00] once you have control even whatever the outcomes are, you feel more confidence.

Joe Mills: You said something really interesting about the, the Covid experience where you felt this like the need to compete go away. 

Sam Jacobs: Yeah. 

Joe Mills: And one of the things that jumped into my head, which tells me I still have a long way to go in, in feeling that same way. Was, how does motivation change when you lose that desire to compete? Because I feel like regardless of the success of your company, it’s always hard. It’s not like, oh, congratulations, like pavilion’s crushing it. So your life must be so easy. Like it could not be farther from the truth. And so you have to have a motivation to continue working, continue growing it, continue like all the things that that takes.

And so I’m curious like when that sense of competition goes away for you. What’s the, like, what’s the motivating factor that gets you to like push through the hard times and keep wanting to do it? 

Sam Jacobs: First of all, what you just said, I could not agree with more. My funny joke is, and again I’m saying it’s funny, I don’t know if it’s funny, but like through Covid through when we raised 25 million in, in two years ago, in April of 2021, people would be like, what do you regret?

What would you do different? And I had this like very zen answer. I was like, you know what? Nothing man. You know, like I, everything was part of the journey and a wonderful Yeah. And, uh, you know, that’s not my answer anymore. Two years later there’s a lot that I regret. And so when you said it’s hard, it is hard.

The hardest thing is like the cons, you know, the market’s hard. Mm-hmm. Because the market has a point of view on what you’re worth. Like that fun factually, right? Like what your company is worth changes. And when you think your company’s worth a billion dollars or 500 million, you think a certain way. And then when it’s, when you’re like, maybe it’s worth 20 million, then you think a certain way.

So to your point like that, it doesn’t get like tremendously easy. And in fact, the past year has been the hardest year that it’s been for me, uh, building and running pavilion. So what is the, my motivation if I’m not competing with some idea about something? The purest motivation is a sense of what’s possible.

That’s the biggest motivation, right? The mm-hmm. One of our key [00:16:00] phrases is we wanna help our members unlock and achieve their professional potential, and I want that for my company too. And so when you see all of the flaws, when you see all of the mistakes, and when you see all of the waste in an efficiency or just like the op and you have a point of view on what it could be, what, what it might be for us right now.

Pavilion has been a non-tech, it’s been a services business, right? We use Slack to manage our community and we use HubSpot and we use Zoom and Crowdcast or Gold Cast or some live streaming platform. And when we do a big thing, we use hopin, but none of it’s our stuff. We’ve never had our own platform.

It’s totally insane that we built a company worth a hundred million dollars that doesn’t have anywhere to log into, that we own until two weeks from today when we will release our platform. So where we are today and where we will be, here’s what I want for the platform and we finally have a product and engineering organization to build it.

I don’t just want a portal, I want it to be like a video game for your executive career. Mm-hmm. And I [00:17:00] want you, I want there to be badges and credentials and I wanna celebrate the people that are doing really well and give them rewards and recognition. And I want to elevate, and I want it to be a place where you can build your reputation in a way that’s a more curated, more structured.

Kind of vertical specific form of LinkedIn. That doesn’t mean that’s all I want. It’s still based on community, but I have a vision for what might be possible with our software platform that is nowhere near to being realized. And I think it would just be the coolest thing in the world if we could take what is currently a services business, basically a tech enabled services business, and become a services enabled tech business, and really turn.

Most people’s idea and experience and perspective on what pavilion could be into more of a software expectation than a services expectation. That’s what motivates me right now is like trying to navigate that transition, trying to make sure that we realize that ambition, trying to make sure that we’re delivering the right level of value.

I feel like we’re a [00:18:00] teenager. We’re not even a teenager. Maybe we’re like 11 or 12, so right on the cusp of adolescence and our voice is breaking and hair is popping up in new places. And like this is, it’s gonna be, we’re in our adolescence, navigating our path to adulthood. And I think there is a path to adulthood, but we’re not there yet.

So for me, that motivates me to want to fix it, wanna improve it. I want you to feel like Pavilion is, there’s a place to go to log into that’s very clear on what it does and how it helps you and that it’s real. I had a call with another CEO recently just getting some mentoring advice and he was talking about how one of his.

CEOs that he mentors and he said, I was, I kept trying to tell her it matters whether it works or not. Which is a funny, funny perspective that there might be a perspective that it doesn’t matter whether it works, but you can imagine a hype cycle where certain companies become so popular or interesting or intriguing and they throw tons of money at growth and they grow really quickly.

But [00:19:00] fundamentally, there’s a question mark about whether it actually works. Mm-hmm. And I wanna make sure that pavilion works. I wanna make sure that if people, that if I say you’re a good fit for it and you are, then you join and you do what I tell you to do, that you get the results that you want to get.

And again, that’s not, I don’t feel like we’re quite there yet. I feel like it’s still more promise than substance and I want to deliver. And even though we’ve delivered tremendous substance, we’ve changed people’s lives, thousands of people’s lives, but I want more, you know, I want it to really, really work.

Joe Mills: Just this morning I was talking to, One of my coworkers, Reid, who is a cos on this podcast about, I have this underlying feeling like there’s always something missing. It’s like, um, it’s like, oh, like, oh, but it’s, it’s, this is good, but it could be this. Um, and I’m, I’m hearing that as you’re talking about it or talking about pavilion, that it’s like, Yeah, we’ve done really good things and clearly we’ve  built from a like economical standpoint, we’ve built an economical engine that people believe and see is valuable.

Hence the valuation, hence bringing on capital. So that’s not a thing that isn’t true, and yet I see so much more for it. And it’s like this, the motivation is I can’t not see that. And when I see it, I, I want to go create it and make it a real life thing. 

Sam Jacobs: Yeah. Of course. I don’t know about the nba right. But if you feel like you could play college basketball at the University of Virginia and win the national championship, hopefully this year we’ll see. 

Joe Mills: Good luck. 

Sam Jacobs: Yeah. 

Joe Mills: I’m an ACC grad as well, but, uh, There are only hope in the tournament this year. 

Sam Jacobs: Where’d you go? 

Joe Mills: I went to NC State. 

Sam Jacobs: Oh, cool. Yeah, NC State’s pretty good this year I think.

Joe Mills: Yeah, man. We uh, might get back in the dance. We’ve had a bad last week, so it could go sideways, but fingers crossed.

Sam Jacobs: If you feel like you could play college basketball, kind of wanna try. Yeah. You know, cuz not everybody can. Yeah. And so, so you get to a certain level and you’re like, yeah, this is great and lots of people will give you a pat in the back, but it’s not.

You kind of want, you just wanna see what is, what could it become, what could it become? And the answer to that is never clear. Mm-hmm. You know, and it’s always a matter of matching your motivation to your opportunity, trying to be realistic, trying to surround yourself with the right people, trying to make sure you’re building the team the right way, trying to make sure you’re setting the vision high enough.

What’s difficult. But for me, yeah, it could just be more, you know, and, and frankly, I would just be proud. I’m in tech, but I run a services business. I would really like to run more of a tech business. That’d be cool. 

Joe Mills: I’m making all these assumptions in the back of my head, so I’ll just ask the question instead. Why? Why would you rather run a tech company than a services company? 

Sam Jacobs: Because I grew up writing fun video games and basic, and I want to be part of the narrative that I’m describing. I am part of this technology, this software as a service. This. Growth of technology and I’ve never had my own software. I like, we have this platform like a demo free when we get off the call, you know, and it’s, I just feel like it’s just the first step.

But it’s super exciting because, because it’s sort of like the future and I’m glad, I’m glad to be part of it. Yeah. We one, instead of commenting outside of it,

Joe Mills: The people we talk with on this show are ambitious, driven individuals who feel called to create positive outcomes in all aspects of their lives. And as we all know, with that drive comes pressure and stress. And in order to show up and be your best self, It’s extremely important to have a professional at your side who can help you navigate that journey.

So that’s the reason that we’re really excited to be sponsored by Better Help. Better Help is the world’s largest therapy service. They have over 25,000 therapists and it’s all online. What’s really great about that is that if you don’t connect with the first therapist that you interact with, It’s super easy to try another, and that allows you to connect with the person that’s best for you.

I think it’s awesome that in this day and age you can just do it from the comfort of your home. I mean, element three ourselves is in a hybrid [00:23:00] environment and we’ve all become accustomed to this world of doing things that fit your lifestyle. So we love that Better. Help can help do that too. And for listeners of this podcast, you can get 10% off your first month on Better Help by going to Better 1000 stories. Again, that’s better. H e l Slash 1000 stories. 

Joe Mills: You bring up something interesting there where I asked you a question before we got on the recording about how you think about team and stuff, and you mentioned we’ve always solved with people and I’m really interested in solving with code, which in the moment I was like, oh, that makes a bunch of sense.

But I’m just, as I’ve sat and thought about it, um, that’s very different. You know, we live inside of a services world, we’re a marketing consultancy, and so we solve tons of problems with people. It’s like how we solve problems and. So I’ve been like running that comment from you over in my head for the last week and I can’t get it out of it.

Sam Jacobs: Oh, that’s nice of you to say. I mean, 

Joe Mills: Well it’s, it’s really interesting to think about like if you kept selling 

Sam Jacobs: Many more comments if you rejoined pavilion engine.

Joe Mills: Yes. There you go. Yeah. Good pitch. I like that your sales background is coming out. Is that a new idea for you or has that been in your head because of your background that you’ve kind of always been like, we’re gonna solve this with code eventually.

Or, or is that like something that comes idea across new? 

Sam Jacobs: It’s a newer idea and that’s why I’m, I’m kind of like intrigued by it. Mm-hmm. Because I’m just used to, I’m used to somebody saying like, there haven’t been enough local events in New York City in Pavilion. And for my answer to be who can I train to host an event and how do I build a workflow where I train lots of people to host events and I run the training session, and then they can go out and they can host those events.

And there’s another way to answer that question. Which is create a framework for anybody to host any event, and then create an advanced search filter in your member directory so that you can say, I wanna meet people that run advertising agencies that are based in Indianapolis, that have a last name that rhymes with schmo sch mills.

And you’re like, they’ll be in, that’ll be one person, but like, and then that’s a search. And then there’s functionality that says like, invite that person to an event and schedule it here. And there’s like, Pretty basic stuff, right? Calendaring functionality, kind of group messaging, functionality plus an advanced search.

And that’s the same thing that I’m saying, but now my brain is learning. So what’s the difference between that way and the other way? Well, in that way, the ability to like give people those tools. Once you build those tools, they exist. Assuming you pro, you pay your hosting bill, like they exist forever.

Whereas like I’ve found, Personally, one of the reasons we used to have these concept of chapter heads in pavilion and we got rid of them, but there’s still this concept of like a local group community leader, and it’s like just the, the differences in performance are so wildly, are so wild, right? Mm-hmm.

Like some people take it seriously, some people don’t. Some people care a lot. There’s this guy Will Craven in London. He’s doing an amazing job organizing, managing his group, which you know is a subset of the London community, and then [00:26:00] there’s this guy in San Francisco, one of our most important markets, who just decided it was too much work for him and just stopped showing up.

There’s a difference between if I build it with code and I train people how to use it right way and they understand what to expect, that could be a very, very powerful thing. 

Joe Mills: Mm-hmm. One of the things that I, I experienced this when I was a member of Pavilion Revenue Collective and then Pavilion. Even in my offboarding, I felt this, so I, I think you should hear it, that I felt a, a really good level of like concierge service and genuine curiosity from your team.

Hey, why are you here? And then when I was leaving, Hey, why, why are you leaving? Tell us how we can get better and not just like, fill out this exit survey so I can to toss it in my database and keep track, but rather like literally help me understand what you were looking for that you weren’t finding. Do you have concern at all?

My assumption, and this is where like I, I don’t have a background deeply inside of technology and don’t think through how to solve that sort of thing. Do you have any worry around losing the like member first white glove service orientation as you try to solve these problems with tech? 

Sam Jacobs: Yeah, of course I have a worry.

But if I’m the customer, I don’t really like talking to people unnecessarily. If you want the honest truth, like with my, uh, the example I use is like Delta. I’m a big Delta Stan, as the kids would say. I don’t even know if the kids still say it. Maybe they say, 

Joe Mills: I’m not sure if they do either, man. 

Sam Jacobs: Yeah, I don’t know.

So I love Delta and I, and I’m a Diamond Medallion guy, so like I think my wife’s one higher, but that’s pretty high. It’s like the second. 

Joe Mills: It’s quite high. Yeah, very high. 

Sam Jacobs: I’m very important. That’s one I’m trying to tell you. 

Joe Mills: No, you’re a super important person. I’m a well informed person. Tell your old therapist that.

Sam Jacobs: Exactly. But here’s my point. So here’s the things that I did recently on Delta. I changed. I canceled a flight and got a $2,000 refund. I changed my seat. They notified me when my bags were on the plane. I checked in. I got through T S a precheck and all that stuff, and boarded didn’t talk to a single person that worked at Delta the whole time.

The whole thing just worked. It just works. And I am a busy person and my point of do I, what is the definition of white glove? I’ve got a, like, have different limits on credit cards. So, but the American Express website has been broken for like years in the specific functionality of managing limits on credit cards through the website.

So I have to call American Express when I wanna do that. Is that an optimal, is that a white glove experience? Not at all. Yeah. You know, it’s annoying. Yeah. Um, so, When you are signing up, right? Like, let’s imagine signing up, right? And like you want to, you wanna enroll in pavilion, you want it to be a premium executive community.

Well, um, given how much you currently pay, uh, which is 2,700 bucks a year, I can’t really afford to hire like mid 30 senior executives to interview you. So I can, what I can hire, afford to hire is like young people to interview you. So you tell me what’s a more premium white glove experience. Being interviewed, quote unquote, although they’re really like effectively a salesperson by a young, a well-meaning high quality, high ethics young person, or just signing up on your own cuz you knew that you wanted to join Pavilion.

Mm-hmm. I think it’s a better experience to just be able to sign up. If you know that you want to do it and you like what we do and you feel good about it, I think that’s a better experience. So, am I worried? Yeah, I am a little worried. I’m worried about their perception more than anything else that like it’s just a thing that anybody can join.

I think that we’re moving into a world where white glove doesn’t just mean human interaction. For a lot of Gen X, for a lot of people in their mid thirties and above, they don’t associate white glove with meaning having to talk to a person. They actually associate white glove with technology that makes it super easy and quick.

Joe Mills: Mm-hmm. Yeah, it’s a good point. It’s like my. My baseline like assumption there was that white glove equals human interaction, but you mapped out really clearly how that does not have to be the case. And it’s sort of like, well, if your foundational principle for the thought is maybe not true or has other answers and the whole thing sounds a lot easier, it also just reminds me of the way you map out your recommendation for growing.

A business to like that. Marketing comes a long time before your sales team does, which from a sales background and a tech background just felt very different than what I expected you to say. It sounds really similar here. Cause if you want people to make a decision to sign up on their own without talking to effectively a well-meaning salesperson, your message and articulation of the value have to be be so good.

Sam Jacobs: Yeah, I mean, that’s understanding it. That’s exactly right. First, there’s a couple things that are true. The first is if they’re gonna sign up on their own, my messaging has to be good and their intent has to be high. And if both, and that’s why we remove monthly memberships at the beginning of this year actually, because I don’t, everyone’s like, well, I wanna try before I buy.

Well, maybe I’ll create some kind of like, um, low cost or. Really, like we have a portal, so I’ll give them, they’ll be a free membership that you can’t do much with, but like, sure they can take a chore around and sign up. But I want high commitment because it’s, it’s still basically a gym membership. Mm-hmm.

You know, it’s still basically like if you wanna get in shape at a gym, you’re gonna have to be motivated to do it, and it’s not gonna do itself and pavilion’s effectively the same way. It’s not a thing that just happens to you. You’re gonna have to like lean in and deeply engage. So anyway, that’s, I want to grow.

The incentives without a big sales team. And I’m not saying I have anything against sales. I’m saying like the math has to work, right? Mm-hmm. And the other thing that we’re finding in SaaS particularly is like, it’s not clear that the math did work. It’s not just that the markets are down, it’s that core assumptions are being investigated, like mm-hmm.

It’s a cohort. Really, this, the a thing in the way that we think it is. Like, is it really, really true? This group of people renews at this rate, or are there things that are masking their behavior? And what I’m trying to articulate when I say marketing first is like, let’s put all the, let’s put as much pressure on the product and the message as we can.

So that heroic efforts by aggressive sales people. At least in the SMB world, an enterprise where it’s impossible to cancel and where you build these workflow solutions that are embedded, like maybe it’s much more difficult. But in the commercial and SMB world or the direct consumer level, I’d rather just have such strong advocacy, word of mouth and product happiness. That’s what drives growth. 

Joe Mills: I feel like it takes a level of patience to fully commit to that. Cause you’d probably be faster. Like it would be faster, right, to have like. 

Sam Jacobs: Faster and more expensive, and you’re gonna need access to capital and you’re gonna need to have strong perspective on the whole thing about SaaS, right?

The whole thing about like recurring revenue is we’re gonna spend a lot of money. We are willing to spend a lot of money to acquire a customer, right? We’re willing to spend a lot of money on brand we’re spending, we’re willing to go do steak dinners in Indianapolis, and maybe the next one’s free. And we’re willing to pay an sdr.

And this sdr, they have no experience, but they tell us they need 75 K base. They need to make a hundred and we need, and there’s a 25 year old AE that just got promoted. That tells us they need to make one 50 and there’s an SDR in all of this apparatus. Right? And we’re gonna, and all of that. We’re okay with that because once they join, it’s profitable for us on a per customer basis to serve them and they stick around a long time.

And so I can recruit the money that I spent on this aggressive acquisition effort because the thing works. Mm-hmm. The thing works. So would it be faster to hire a big sales team? Yeah, it would be faster, but you gotta know, does the thing work? Mm. And does it do what it says as the English was say, it’s just my favorite expression.

Does it do what it says on the tin? And if it doesn’t do what it says on the tin, or you’re mismatched somewhere because of your interest in growth. You went after people that aren’t quite the perfect fit. Everything breaks. And the problem with it breaking is it doesn’t break. The first thing you see is the customer signing the contract.

Mm-hmm. And you’re like, oh my God, it’s working. And then maybe the first group of customers renews, but at scale, do they renew? Does are they, do they predictably renew? Does anybody renew? And then, you know, and then there’s like deeper, more existential questions like, does anybody renew anything? And what do I mean by that?

That sounds a little ridiculous. It’s not, if you have, if you tell people that you have 90% gross renewal rate, right? Meaning like logo retention, right? These sign up, 10 customers, nine of ’em are around at the end of the year. You’re like, well, what? So let me tell you what that math means. That math means that on average, your customer sticks around 10 years, and that’s what you’ll tell people.

Now again, are you doing this at scale? Pick a service that you’ve signed up for Joe, where a product could even be the headphones you’re using. Both monitor. Pick a thing you’ve used for 10 years without switching. [00:35:00] It’s so low. Yeah. My, my iPhone. Just different pause. Yeah, exactly. Maybe your iPhone. Maybe that’s it.

Maybe your iPhone. Maybe that’s it. And maybe even, maybe you’re like, I was thinking actually about getting an Android this year. Like I was finally gonna do it. Like there’s no service. There’s outreach, right? Like versus SalesLoft Gong versus Chorus, ZoomInfo, 6 cents versus demand base. Any of these things.

Is there anything that people really don’t switch out every like three years? We were a HubSpot CRM shop. I love HubSpot. I love them. I hate Salesforce, I hate that company. And we hired this amazing Salesforce admin, and he just made us switched Salesforce. Congratulations. No, I hate them and I respect them.

I respect Mark Benioff like it’s an incredible company. I just don’t wanna be their customer, but I am their customer. But here’s the point. The point is that even HubSpot, who I love. So, uh, I, I stuck around. We, this was the free instance from when I started my consulting business [00:36:00] in 2017. Wow. And we were like basically meaningful s and b customers for three years.

Yeah. Okay. So three year lifetime is 66% gross re renewal rate. Anyway. What is this rant all about? This rant is all about, it would be faster to hire a big sales team, but they’re expensive. And if you’re gonna do that, you have to have a lot of confidence in the math. And most people are overconfident in their math because most people don’t stick around as.

As much as recurring revenue businesses would like or tell their investors or their stakeholders. 

Joe Mills: Yeah, it’s interesting. There’s a terminology in the agency world that is the Black Hole Agency where clients, they come in and they work with this company and then they never leave. And for the vast majority of the, like looking back on the agency world, that is what the model is like, find your customer, keep them forever.

And I think you bring up a really good point around like, where else is that? Real? Is that a real way to build a business? It’s just something, it’s a very interesting thought exercise that we’ve been putting through our heads as well, cuz it’s, yeah, I mean, I’m having a really hard time thinking of a service.

There’s products that I buy over and over again, but from a service standpoint where I haven’t changed, 

Sam Jacobs: I mean, I’ve been back and forth between Riverside and Zencaster. Yeah. You know, like, and uh, sounder and ta and it’s like, so what does that all mean? All of that means this is not like, uh, the doomsday.

This means that you have to be really careful about how much money you spend on customer acquisition, because most businesses today aren’t as stable as we want them to be, which means they’re not, which means you can’t afford to spend as much on customer acquisition, and it means that you really need to be really honed in on your product so that it can grow in more efficient ways.

And the most efficient way is that people like what you’re doing. And they decide to join you and they stick around. 

Joe Mills: Yeah. No, it’s good. It’s awesome stuff. Um, I’m, I’m very curious. We’ve talked a lot professionally. I’m very curious, like you have a lot, I, I get from you, a lot of intentionality, a lot of self-awareness, uh, and, and a lot of like self-discovery things like your own personal values that lead toward, toward pavilion being launched outside of the professional sphere.

Where have you seen this impact you in a meaningful way? This, this whole discovery process? 

Sam Jacobs: The most obvious ways with my wife, with my marriage and my expectations around other relationships and really trying to, yeah, I just read this book by the Arbinger Institute. I don’t know if you know who they are, but they’re, they do pretty cool stuff and their values are pretty aligned with mine.

And they wrote a amazing book called Leadership and Self-Deception, and then they just wrote a shorter book called What? They didn’t just write it called The Outward Mindset. And the point is that like a lot of like blocks in my life have been because. I create this narrative where I am the victim of circumstance and we all see other people in two dimensions and ourselves in three mm.

And the more that you can see everybody in three dimensions, the more that you can really just try, like, really try and develop empathy, not superficial empathy, but really try and accept people. Not even accept people for who they are. Celebrate them for who they are. It’s not easy to do, and I don’t do it every single day, but.

It’s impacted my personal life because I’m far more accepting of my wife. Mm-hmm. Not that she’s like such some kind of terrible person or anything like that. Yeah. But because I don’t view her behavior necessarily as like a, as a commentary on me. Mm-hmm. She’s doing her thing and I’m doing my thing. And, uh, the beauty of a partnership is when you, when those things are joined, when you’re both independent human beings coming together to form a partnership.

As opposed to co-dependent. And co-dependent literally means if you’re unhappy Joe, then I cannot be because I am dependent on your happiness to be happy. Mm. And the real shangrila is, it’s not that I don’t care, it’s that it’s not dependent. I don’t require anything from you for my own sense of fulfillment and satisfaction.

Therefore, I can set you free of any expectations. That you might feel that I’m projecting onto you and you can just be free to be your best self. And hopefully the Buddhism of it, the yin yang of it, is that by setting you free, you actually would become closer. 

Joe Mills: That was lovely gen. Genuinely, um, I resonated with a lot of that.

I don’t know if it’s just a couple of fours who have similar outlooks or if it’s, if it’s really there. You said something around like, her actions are not a reflection on me. And my wife and I have been married for a little over five years, and I really find that when I’m in my deepest, darkest spots, it’s because I’m taking my perceived, the like, I’m almost like writing stories about other people’s activities that don’t relate to me and then applying them to myself.

Sam Jacobs: I mean, are you welcome to my life? Yeah. You know, that’s like, we’re supposed to be spending more time together and she isn’t home yet. And that’s, and it’s like, and I do the exact same thing. Mm-hmm. But somehow I’ve forgiven myself for the same behavior. We talk about. She, me and me and my wife, were talking about how we, we really like Jesse Hitler and Sarah Blakely.

Mm-hmm. And their whole thing is what is, what did they say? Seven or below? Let it go. Mm-hmm. Um, meaning like, if on a scale of one to 10, the, the friction is the, the frustration is a seven or below, then just let it go. And it’s this idea of like, it’s not about you, it’s not a commentary. They’re going through their own thing.

Mm-hmm. And what they really want. Is what you want, right? What you want is to be accepted for who you are and not feel like, Joe, you didn’t do this and you didn’t do that, and why are you doing this to me, Joe? It’s like, well, I’m not doing anything to you. I’m just like going through my own tough time.

Mm-hmm. So, yes, I feel like the more that we can let people free of our expectations and understand that our expecta, but again, I’m saying this as if I’m good at it. Mm-hmm. Just to be clear, like I’m not, I’m not great at this. I’m just trying it. 

Joe Mills: I was gonna ask if there’s anything that you find as like, whether it’s a daily practice or an activity or anything that like helps you progress in that or is it literally just like, oh, I did it again and like starting to recognize it and just try to fix it in the real moment?

Sam Jacobs: I think, um, the daily practice is get a good night’s sleep journal self-compassion, which I talk about in the book. Mm-hmm. Try to meditate or find some calm. When I’m at my best and I feel pretty good today cuz I got 10 hours of sleep last night. I went to bed at, you know, 10 and like woke up at whatever, seven I journaled this morning.

Like when I’m calm and steady, that’s when I can bring my best self. The converse of that would be playing too much online chess, not getting enough sleep. Not journaling, being distracted in meetings. Mm-hmm. You know, it’s like, probably, maybe that’s cuz I’m like, hungover, maybe I drank too much the previous night, but I’m, I’m, I’m a fan of alcohol.

Like, I’m not saying, yeah. I’m not one of these lifestyle gurus. I’m just saying that everything you can do to be calm and be like slow and low and slow, like barbecue. Like the more that you can approach your life with a little bit of just calmness, like that’s the thing that helps I find. Mm-hmm. So what’s the thing they’re gonna equate to calmness?

It’s like healthy practices, exercise, meditation, reading books, putting down your phone, listening, you know, having a, an interesting conversation with your partner. Those are all things that I think that lead to good success. 

Joe Mills: I love it. Well, I think I’ll leave it there, man. I’m gonna remember that barbecue piece, especially, it’s my favorite type of food, so it’s gonna be very easy, low and slow, like barbecue.

Simple one for me, Sam. Thanks a ton man. I really appreciate your time. This was a really fun conversation and I, yeah, just, I’m looking. Looking forward to people listening to it, and I hope it gives people some good info. Where can people check you out and get the book and whatnot? 

Sam Jacobs: Uh, well, they can get the book wherever books are sold.

Uh, the audiobooks coming out the end of this month, march. Great. Uh, join Uh, to become a member. I should be hopefully evident [00:44:00] how to do that. And you can find me on LinkedIn, but you know, like I said at the beginning, the the, the main way I wanna be described is as, uh, as the guy runs pavilion.

So if you’re interested, go to join 

Joe Mills: Awesome. Well, thanks so much, Sam. Appreciate you. Thanks. 

Sam Jacobs: Thanks Joe. 

Reid Morris: Okay, Joe, so another really great conversation, uh, with Sam Jacobs, uh, another individual who fits the bucket of founder right from, from the people that we’ve talked to. Um, but is it a different part of the story arc than some of the other individuals that we’ve spoken to recently?

Yeah. So talk to me a bit about what you found really interesting from, from his journey and some of the key takeaways for you. 

Joe Mills: Well, Sam has had a different journey point than a lot of people. He has realized, financially realized the benefit of all the work. Mm-hmm. Which is just an interesting thing. Not that the people we talked to haven’t been really successful in, in doing that, but he took on substantial private equity and part of that was directly to him.

And so talking to somebody who has realized, like if you were to ask an entrepreneur, what do you hope to do? At the end of the day, while they want to obviously make a giant impact, like part of what they’re building is the ability to create financial freedom, generational wealth, things of that nature.

Yeah. Otherwise you don’t take the risk. And so talking to somebody who’s done that was really interesting. And the thing that I really enjoyed was asking him like, what keeps you motivated? Because one of the things about Sam is so he just. Had a book come out fairly recently. It’s a Wall Street Journal bestseller.

I just finished it. And in that book you get a very clear sense and he talks about this like complete drop of competition in the way that we normally talk about the term. Mm-hmm. And so I asked him, I was like, Hey, you’ve made it. You also talk about dropping this competition. What’s the thing that keeps you.

Building something because regardless of, you know, from the outside you hear it raised a bunch of capital worth 200 million valuation. From the company standpoint, um, it must be easy. That’s never the case. We obviously know that it’s never the case always hard. So why do you keep doing this hard thing over and over again when you don’t need to by the definition of need?

Yep. And he was like, I just really want to see how good it can be. Mm-hmm. It’s like, I, like I see these problems with it. I see how far away we are from the vision I have for it. And it gets me excited and motivated to go out and keep trying to build that. And what I really appreciated about Sam is that he’s somebody who can both see this future visionary in nature.

Reid Morris: Mm-hmm. 

Joe Mills: And want to get his hands messy in what it is currently. And he can be comfortable in that. It’s like, It doesn’t torment him. 

Reid Morris: Mm-hmm. Yeah. 

Joe Mills: You know what I mean? It was like instead of being like, oh, I just have to, cuz it like kills me to see it twi. It was like, no, I’m just excited to see how great it can be.

Reid Morris: It’s really an interesting twist on this idea of gain and gap mindset. Yeah. Where it feels like he has a really healthy balance where rather than, like you said, feeling pain about how it is and that being the driver of it needs to be better. It’s seeing how great it has been and how great it could be.

And really keeping that positive mindset and that shift in how he’s thinking about it. It’s already good, but there’s so much room for potential to make it even better. 

Joe Mills: Yeah. And from a personal standpoint, when you talk about the agram on this show regularly mm-hmm. And thank goodness Sam doesn’t, he’s not a, he’s not a quiz Agram good.

We’re happy about this. Um, but he, he’s a four is what he feels he identifies with. And I have recently realized that one of the things that I thought was just normal is this. Feeling that there’s like something missing that just torments you. 

Reid Morris: Mm-hmm. 

Joe Mills: Always in every part of life apparently. It’s not normal.

It’s apparently a, a thing that fors experienced and uh, so I’m leaning towards, I think I’m in that bucket, but it was interesting to see how that can either torment you, like I was talking, oh, it just has to be better. Or it can be like, oh, look how good it can be. Mm-hmm. And the difference between those two feelings mm-hmm.

Is. Whether or not you enjoy making it great. 

Reid Morris: Interesting. 

Joe Mills: Yeah, so like putting all of that together and even going outside of the show a little bit, I’m, I wrote a post up about it was referencing F1 and this like, fear of failure, fear of losing versus joy of winning. 

Reid Morris: Mm-hmm. 

Joe Mills: And Chip Knight also a guest on the show was like, I think there’s another layer to this that is enjoyment of the journey rather than the outcome at all.

Reid Morris: Yep. 

Joe Mills: And actually, funny enough, before I even, before he commented that Katie had said to me like, Hey, I think this thing is applicable and shit. The same thing. Like is there something about like just forgetting the outcome and just enjoying doing what you’re doing? 

Reid Morris: Mm-hmm. 

Joe Mills: And I think that’s Sam’s point around it. Just, I wanna see how great it can be is the thing that gives you fulfillment in the journey, gives you motivation through the journey, makes it more fun. And then the outcome is like, oh cool, we made it as cool as it can be. Or the outcome’s like, oh, it’s still not there, we’re gonna keep doing it. 

Reid Morris: Mm-hmm.

Joe Mills: Um, Yeah, it just, it was really interesting to see all of those things sort of like layer on top of one another at a, at the, at like the same time. 

Reid Morris: And I think what that does on some level is give us a new lens as we go into future conversations. And we’re experiencing people who are at different points of like their founders journey, right?

Or at different points of building culture, whether they found it or not. How does that mindset overlay look for them? Yeah. Where are they in that? Is it a healthy growth mindset? Is it more pain driven? Where are they on that journey? I think it’d be an interesting thing for us to pay attention to. 

Joe Mills: Yeah.

Reid Morris: As we dive into more people’s stories about the businesses that they’re building and running. 

Joe Mills: There’s um, somebody who, I just started his newest book, his name’s Steven Kotler, and he’s a, a researcher. 

Reid Morris: Mm-hmm. 

Joe Mills: And he researches largely the science of flow and, um, all the pieces that go around that. And he talks about the fact that fear is a really strong motivator.

It will get you to do many things, um, but it’s not necessarily the best one. 

Reid Morris: Mm-hmm. 

Joe Mills: It’s the most like, oh, you will do it immediately. Like you’re scared of the sabertooth tiger eating. You, you will run fast, 

Reid Morris: But jerseys of the sustainability to do it for the long run. 

Joe Mills: Exactly. Is it definit is something different, different at the different level to it.

Reid Morris: That’s awesome. I, I’m excited to see where this thread goes. 

Joe Mills: For sure. 

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