The CX 025: (Don’t) Do the Hustle: From Hospitalized to Sustainable Community with Tom Ross

The CX 025: (Don’t) Do the Hustle: From Hospitalized to Sustainable Community with Tom Ross

Tony Bacigalupo: What does success in community look like? Is it getting hundreds and thousands of customers and just grow, grow, grow, and giving yourself lots of work? Well, our guest today Tom Ross went there and literally got himself hospitalized from the burnout. And so we're going to learn his story and the more sustainable path that he found in the aftermath. So stay tuned and learn more about sustainable community growth on this episode of The Community Experience.

Okay. Hey, hey. Hello. What's up, everybody? Tony Bacigalupo here.

Jillian Benbow: Jillian Benbow in the house.

Tony: So Tom Ross is an amazing story. So I came up in like a tech culture and-

Jillian: Same-

Tony: ... in the late '90s, early 2000s there was such a strong culture of hustle, hustle, hustle. It's the internet. There's unlimited opportunity. You can build a startup and be the next Yahoo.com. It was like a lot of this sense of like a really powerful gold rush culture.

Jillian: Yeah, absolutely. I mean, I think we all see it. The tech culture has spilled over. When you get funding, that's a make or break for community culture. Nothing can crush a community culture faster than hundreds of millions of dollars.

Tony: Yeah. It's wild. And, I mean, I've worked with friends who have had funded startups and I remember they said, "Money's not even an issue. We'll spend the money on whatever we need to spend it on. We just need to grow so incredibly fast. We need to hit these insane numbers in order to meet our expectations." And that can be hugely challenging. But it's not just a venture capital thing and maybe not just a tech start up thing either.

It's maybe a cultural thing as well. And unless you're really proactive about thinking about, "Wait a minute is this healthy? Is this sustainable?" Then it's going to hit you at some point.

Jillian: Yeah. And I think like we were saying, it's very prevalent in tech but it makes sense that people who are starting their own businesses kind of follow the startup culture. There's a balance between finding something sustainable that has an ROI, if you will, whether that's financial or just fulfillment in some way.

And just making these crazy goals for the sake of being able to say you did it and then either turn around and sell that idea to other people like the six figure launch type trope or whatever. But I really challenge that way of thinking. I don't think it's healthy. And I think Tom really gets into that. Quite literally it is not healthy.

Tony: Yeah. So we're going to get into that conversation in a moment. I think one of the other things to keep in mind is that especially when you're building a community, this is all that much more important because you can't just treat your people like statistics. And I think when we get into where Tom went after his burnout journey, we'll learn a little bit more about what it's like to build sustainably and in a way that really treats humans like humans, which I think is great. So what do you say, Jill? Shall we do it?

Jillian: Yeah, Let's do it. Let's get into it.

Tony: Tom Ross, hello. Welcome. Thank you for joining us.

Tom Ross: Thank you so much, Tony, Jillian. It's an honor to be here.

Tony: Welcome to the program. We're really glad to have you here. Wanted to just start with, tell us your life story in just a few minutes if you don't mind.

Tom: Okay. I'll give you the very sped up version. I started when I was like 12 years old, and I sat there with my best friend. He right clicked on a webpage, hit view source, and it spat out all this HTML. And it was like the first time I saw the Matrix. I was like, "Oh, my people make these things." And a couple of kids, we started making websites together and doing all these random projects through school.

Some of them were just pie in the sky dreaming, some made a little money. And we just grew these projects from there. Over the years, I did everything from client services, design, marketing, freelancing, all that good stuff, blogging. And I always love communities. So when I was a teenager, I was a huge fan of the band Interpol to a nerdy degree. Especially the first two albums. Amazing.

And I started a fan site, a website just documenting all this stuff and a fan forum. And it got so popular that it actually I think at one time was busier than the official band forum. It had like a quarter of a million posts at one point. People spent their lives on this thing and it was insane. And that was my first real exploration into community. I was like, "This is super fun. I'm making really good friends here. I get to geek out over this common interest." And it was amazing.

It didn't make any money obviously, because it was a band community fan forum thing. And so I came to the force assumption that, "Oh, community and all this people stuff is fun and it's what speaks to me, but it's not really business." And all the internet marketers on Google are telling me that I need to be focused on driving insane traffic and funneling people and all that stuff.

So I was like, "Well, I want to do this internet stuff. I'm going to educate myself." And you can imagine a lot of the stuff that came up was very sleazy internet marketing and telling me the wrong stuff. And I followed it not in terms of treating people badly, but in terms of focusing on vanity metrics and things of that nature. I build a blog. The marketing worked to some extent that got 15 million visitors over a few years.

And I was like, "Oh, my God, I've made it. I can do marketing." And what transpired was, it was very hollow. It was just empty meaningless metrics, terrible time on site. The revenue helped pay through college, but it wasn't a scalable, sustainable business. And I felt really disillusioned. I then went and joined a membership community for entrepreneurs. And I got some mentorship from the founders.

They set me straight in terms of like, "It's not about all that stuff. It's not about this easy marketing. It's about the people. It's about serving a world to find audience, building community around it." And everything started to align. I was like, "Oh, so the stuff that spoke to my heart can also be effective business. Maybe this is the sweet spot." So I became one of their... I think it was Fizzle, the community, if you've ever heard of it.

Pat’s actually spoken there and so on. So I became a Fizzle whiz, because I was one of their success stories, I guess. And on the back of their incredible mentorship, I started also binge listening to a lot of GaryVee back in the day. This was early stage GaryVee, basically screaming in your face to hustle harder.

So I took all my community knowledge and my marketing knowledge. I took all my GaryVee hustle and I started my company about eight years ago. And we literally had no business plan, no revenue goals, no growth goals. My one goal was, I've done a big hollow audience and I want to build the most engaged community I've ever seen. That was my one starting goal. So I started the company.

I literally made best friends with our first two, 300 customers. I was jumping on one my phone calls. People used to message me and say, "When do you sleep?" Because I get back to every email within two minutes. Super unsustainable. I knew about their families and hobbies and they knew about mine. Built these really deep relationships, created the ambassador program, where we got these early customers and built with them and got their feedback and iterated the product very rapidly and tried to connect them as much as possible.

As a result of that early community and great product market fit, the company just took off like a rocket in the first year. I was working 18 hour days, seven days a week for a year and a half. I managed to hospitalize myself, burn out horrendously, have major surgery, become chronically ill for years to follow. And the whole time I was bedbound and looked like a shell of a human.

I was keeping the company going, trying to sustain a culture and look out after our team and maintain payroll. And then to take a breath, more recently the company's eight years old. It's continuing to scale. It's much healthier. We've got an incredible team. I've learned a lot of lessons about work life balance and not acting like a moron working yourself to death. And alongside that, my side hustle is teaching community, which I do under my personal brand. And I get to talk to awesome people like you on that topic. I don't know if that was five minutes, but there you go.

Tony: Oh, that wasn't a specific edict anyway, but I appreciate you. Thank you so much. We need other people who are maybe going to potentially end up following in your footsteps to maybe hear stories like yours and head off the hospital. So thanks for doing that.

Tom: Yeah. Thank you. I try and speak out about it a lot. And you can see younger earlier stage entrepreneurs going down that same path and doing what I did, which you see all the red flags and you have good people around you telling you, "This isn't sustainable." And you're like, "I'm different. I'm going to power through." And I think thankfully there's a healthier narrative around mental health and balance these days compared to a decade ago.

Tony: Yeah. I'd like to really hope that there is this narrative shift. I remember when I was coming up, I was in the tech scene and I was also a community builder. And there was such a strong sense that if you are not working 18 hour days and sleeping under your desk, then you're not a serious entrepreneur and you're not really going to make it. And I just feel like there's a lot of examples being set and part of why I'm so passionate about SPI is because we really encourage that embodiment of a healthy sustainable entrepreneurial lifestyle.

Okay. So here's what I'm curious about. I burned out but not nearly as bad as you did, but you bounced back so much higher. One day you're in the hospital and then now you're here doing all this awesome stuff. How did you get back on your feet and how did you find the willpower and the metal to go back into this world knowing where you ended up the first time?

Tom: It actually took me a while because there was some very deep rooted bad habits that I'd been absorbing. So the dumbest thing was I went through this horrendous experience and literally I was bed bound for a while. I was on a liquid diet. I'm a naturally slim guy anyway, but I dropped... I'm trying to do it pounds. I think that's what you use in America. I dropped nearly 30 pounds very quickly. I could barely stand. It really wasn't good.

And when I went back to work, I actually started trying to hustle again, believe it or not. Even after all that, I was like, "Okay, well, I've had the surgery, let's get back at it." And that didn't work. My body was like, "Nope." So I think there were a few things. So first of all, the trajectory of the company was so good. I wouldn't say that this helped it. This probably did hinder it, but it stalled the growth. So it continued to grow naturally, but not as quickly as if I was at 100%.

So I think that's one part. It also forced me to delegate. So that was the big silver lining. Before I was trying to do everything myself, I was such a control freak. We hit seven figures and I think I'd only hired like one part-time staff member at that point. And I was the only full-time staff member running a seven figure business, which is ludicrous, right? Completely unsustainable.

So, yeah, this totally forced my hand and we very aggressively started scaling out a team. And now we have a team of over 20 people and they're incredible. And we are doing things that we never could have done when we were smaller. And I think as well, this is the truth. I still struggle. So I have some residual albeit much milder health conditions even now, where I've been ongoingly seeing a doctor.

And ironically today for whatever reason, I had my worst health day morning in months. I actually had a pretty good run. But earlier I was on meetings with my team, I had my video off, I looked super ill. I've got a bit more color in my face now. But it's been a bad day. So this is not necessarily the triumphant story of victory. This is like, if you act in a stupid way and you work yourself into the hospital, there can be some long term repercussion. But I love what I do. I show up. I do so with more self compassion and more balance now, and I just do what I can.

Tony: Tom, my respect for you just went up even more.

Jillian: I'm curious what you look for now. You said this morning, you could tell like you felt off. So are there other things that signal to you that, "Ooh, I might be pushing it too hard." Or even are there policies with your company for your employees that are like, "Hey, take the time you need." How do you recognize when the burnout is bubbling up and so that you can proactively take a step back?

Tom: So one thing I never did was impose my hustle mentality on my team. I was very clear on that. I have friends that work for startups where the CEO's there saying, "If you're not here at midnight with me, then you're not part of our culture." So I actually think we've got a culture predicated on balance. We're very bullish about allocating time off and trying to support people, whether it's mental, fiscal health balance, et cetera.

With myself, I actually have a checklist because I think otherwise if you just have the vague intention of like, "Oh, I should try to live in a healthy capacity." That's too ephemeral. So I have things. I have to get eight hours sleep. I have to drink enough water. I have to try and eat at reasonable time. I can't work beyond a certain number of hours each day otherwise that becomes unsustainable. And there's about 10 things on this list. And I call it my self-care list.

And I have this theory that burnout actually comes from an absence of self-care even more so than simply overwork in isolation. Because you can actually work pretty hard if you are also sleeping and eating right and looking after yourself. That's more sustainable than if all that stuff goes out the window. If you have no self care but you're working even 10, 12 hours a day, then you can burn out pretty quick.

Tony: It sounds like there's this adage that keeps coming up in so many other contexts of what you pay attention to grows. And that in a lot of cases, if you're focusing on the problem, then the problem just continues to have this primacy in your life. So if it's hustle, hustle, hustle. Oh, no, my hustle's a problem. I need to hustle less or I need to manage it better. You're still focusing on the problem area where you're suggesting maybe nurture the solution space. And that will help fortify you.

Tom: Yeah, I think mentally as well. I went and saw a therapist. I had to build this team around me. It was that bad. So I got a therapist. I got a personal trainer. I got a dietician to try and rebuild me a few years ago. And the therapist said this really interesting thing. She said, "Your inner voice is completely devoid of self compassion." Where I was like, "Failure is not an option. You have to do more. It's not good enough." All this stuff.

So now I'm very hot on self compassion and I really think this maps to community and indeed all online business, etcetera. But within community, there's always more work to be done right. I literally could give you a list of a hundred things that I know would improve my community, help grow it, progress it faster than ever. And the self compassion is saying, "Okay, I'm going to appreciate what I have been able to achieve. I'm not going to judge myself for what I haven't achieved."

And also the realization that once I do those a hundred things, there's going to be another a hundred things waiting because the work's never done. So now I just go along at a reasonable pace, but much more sustainably. And I think I'm in this for 20 plus years. I have time. I don't need to rush through it all now.

Tony: Absolutely. It seems like a common confluence that people who have really strong ambition and drive have that drive because of something about how they're wired psychologically. And then running a business, running a community, those are things that will consume everything you give it and there will always be more. And so it seems to be a pretty consistent path to injury and burnout unless you recognize that danger and that dynamic and catch it.

Tom: Yeah. I couldn't agree more. I mean, it follows the pattern I think of addiction, in that often the harder you work, the better your community does. And the better your community does, the harder you want to work.

Jillian: I like to say community never sleeps. Yeah. Community in and of itself is an organism. And so I think being able to accept that... And depending on the community too, right? Because I've run some communities that fight. And when they turn, if you don't catch it early, it turns into a... It's just a waterfall of just drama. In my past, some of the most burnt out I've been working in community was this, well, I have to make sure I'm checking in to prevent fights and just the dumpster fire that happens afterwards.

And it's so important in community to recognize community never sleeps and community is messy. And so you do your best. You have guidelines, you have protocols, but then you give yourself permission to not be there 24/7. And it's huge.

Tom: I'm not a parent yet, but I'd imagine it's maybe like parenting in the sense that the truth is always somewhere in the middle, right? It's always balance. So in parenting, you don't want to just let your kids run a mark and do whatever and be totally hands off and be like, "Sure, run into that dangerous part of town eight-year-old. Good luck to you." But equally you don't want to be a helicopter parent where every microsecond you are overseeing and imposing what they do.

And if you map that to community, to your point, Jillian, it's like, well, you can take a weekend and let the community "suffer temporarily." Because people will probably learn from that. You'll learn from that. Hopefully, it's going to come out stronger and it's up to you to get things back on course. But you can't be there every waking second. And I don't think that's healthy either, right, for you or the community. You have to give it some free reign.

Jillian: And I think with a very healthy community, because you're modeling behavior, because you have the rules of engagement, community guidelines, that kind of thing, I feel like you are the people who are there who really want to be there and really get a lot out of it, they will self-regulate the community without you. So if something's getting a little weird, they might tell someone, like, "Oh, yeah, well, we don't do that here. We have this community go guidelines, so we don't do that." And so communities that are well run and engaged, all you need is a few core leaders within your community. They'll uphold what the community should be doing in your absence.

Tom: Yeah. I think that's a great distinction. Now that I'm running a community for community builders, this is a very common mistake I see people doing. They think it all has to come from them.

Jillian: Yeah. Yeah.

Tom: They think all the answers has to come from them, all of the knowledge, people always need to defer to them as the community leader. And really that's more of a membership site, right, than a community. The nature of community is the value and power of the collective. And I love trying to constantly loop in people within the community that have greater expertise than me, or even if they don't have greater expertise, they just have a different perspective.

And so I have to hold back because I get very passionate. I'm like, "Here's the answer is what I want to say." But I have to hold back and be like, "Well, maybe this person has an interesting answer before I jump in."

Jillian: Yeah. I love having open ended conversation and encouraging that so people feel the advocacy to do that, to jump in and give their opinion. I totally agree. Because I'd rather have a conversation with five people who have completely different backgrounds and life experiences than me just saying, "Yeah, we're going to do it this way." And of course, it depends on the community.

But I agree with your distinction between a membership and a community. Ours is between in that. Because we do definitely lead it, people are paying for it, we offer programming and services. But the thing that makes me... One thing that always brings me joy in any community, but especially in Pro is, if someone asks a question that's to do with their membership or where do I find this? And a bunch of people hop in and answer, basically if the community can replace me as their community manager with the help and guidance and things because they know and they're eager to help because that's the community it is, right? That makes me just so happy.

Tom: So getting super practical, we actually run two communities on Circle. So I have my personal brand community. My company design cuts runs a Circle community now as well. And we're just in the process now of actually recognizing a lot of these power users by giving them titles. And I think what's been done historically is people say, "Oh, they're a moderator." And they apply this blanket terminology. And what we are trying to do is we've actually created personas based on how people behave and the positive contributions they make.

So we have teachers who share really helpful tips and tricks and tutorials and love to educate. We have helpers who are always going and answering questions before we even get to them. We have guides who are very good at pointing people in the right direction like you just alluded to Jillian, or welcoming new members. And we have supporters that are always there leaving nice feedback when people share their creative work.

And by doing this, we are essentially building a team from our power users but with clearly defined roles, so that suddenly we have more teachers teaching, more helpers helping, more supporters supporting and so on. And I think that's a much better approach than just like, "Here's five moderators." Where in that title feels draconian, and like that one job is to delete posts that conflict with guidelines.

Jillian: Mod cops.

Tom: Yeah.

Jillian: Are you recognizing that someone fits the teacher avatar and you're reaching out and inviting them? Are they asking to join? How do you go about that?

Tom: Currently we are seeing their behavior and then we're reaching out. So we literally have people that are putting together incredibly comprehensive tutorials. And it's like, wow, they clearly just get a kick out of doing this and love helping other people. So we want to empower that, encourage it and recognize it. And another distinction of this, I don't know if you do anything similar, but we're putting a time cap on these roles.

So we're saying, "Would you like to be a teacher for the next three months?" And then at the end of three months, we can say, "How's the experience been? Do you want to continue it?" Because I think what people often do is they apply these titles for life. And then if someone drops off after five months, they're stuck with this title. Other members are finding them in the member directory and trying to direct things their way, and they may be inactive at that point.

Tony: Yeah. I talk about this a lot. Perpetuity is the enemy. That it's just going to set you up for something to go wrong later.

Tom: Yeah. Don't even get me started on lifetime memberships. I've had some debates on Twitter about this. A one time fee for life for my community and then three years later you are getting zero cash in if it's a pay community. But people are still expecting that service from you, and it's an unsustainable model in my view.

Tony: Have you read the stories of the airlines that sold the lifetime passes? Oh, it's incredible.

Tom: I haven't.

Jillian: That one guy that...

Tony: They needed cash, right? The airlines were short on cash and they did this deal where they would sell a lifetime unlimited flights for a couple $100,000 or whatever it is. And some people bought it and they did the math and figured out that essentially they really could get their money's worth. And the airlines absolutely brutally regretted it to the point where they ended up deploying a task force of lawyers to figure out how to get some of these people to to be considered in violation of their agreement to get them off of the ledger, because as they were costing the millions of dollars a year. It's a really awesome story.

Jillian: Back to these titles, for lack of a better term. Are you setting expectations when people accept? Okay. You're a teacher now this is what you need to do. Or is it just like, "Keep on keeping on." And you assume that they'll keep behaving the same way?

Tom: Great question. Yeah. We are setting expectations but I think there's a middle ground, right? I think it's more like gentle guidance in the form of expectations. Because what we don't want to do is say, "You didn't share your tip this week. We're going to retract your teacher, Monica." Because they're doing it for free at the end of the day, right? They're really doing us a favor. It's not like holding someone to KPIs within a paid role. So, yeah. Gentle guidance.

Tony: Well, I suppose a lot of it's in how you frame the relationship and recruit so that their motivations should be aligned such that they would want to contribute in the way that you hope they will. Are you noticing any patterns in terms of who tends to work out for the better versus not?

Tom: I think it often comes down to intrinsic motivation, which is something I've been trying to learn a lot about this year. And this is why it works well, I think, when they're already exhibiting those behaviors and you're just trying to amplify them. Something I have learned particularly being deeper than ever in community this past year is that people and humans are unpredictable through no fault of their own.

And so what you'll often find is you'll get an absolute power user who can become completely inactive and vice versa. And if you look at it just in terms of numbers and data, you can freak out. And you can say, "What's happening there. That's not right. I need to fix that." And often there's very human reasons. So I had this recently. I'd reached out to someone, "Is everything okay?" I was thinking they used to be one of our most active users and they'd had some really terrible personal things happen to them.

And immediately I shifted from insecurity of, maybe they don't like the community. They think I'm doing a crappy job. I need to step my game up. Shifted immediately from insecurity into empathy and embarrassment at my approach of thinking this was all about me somehow I'm like, "No. People have lives. People have lives outside of my community and guess what their lives are and certainly should be a lot more important than my community is."

Tony: There's value in not over analyzing things and not taking everything personally. Recognizing the ego maybe jumping in sometimes when you see a behavior and it's not always about you.

Tom: Yeah. I've I said this for years, not even necessarily about community, but I think anxiety lives in the micro and calmness and correct ways of thinking live in the macro. And what I mean by this is... I still do it now to be honest. But if I refresh our revenue chart within my company, I can be there refreshing once an hour and feeling really anxious about the trends. But if I zoom out and see the wider trajectory and trends I'm like, "Oh, okay. It's fine."

And it's the same thing with our communities. I think it's unhealthy to put everything under a microscope all the time and overthink it. But obviously if you zoom out and you see a fundamental negative trend with your churn or your growth rate or whatever it might be, well, then you need to address that.

Tony: Sure. Yeah. You're striking their thoughts because you don't want to stick your head in the sand either. You want to be keeping your eye on what's going on.

Jillian: It's really easy to get obsessed with engagement metrics and member behaviors and things like that. Looking at a budget or a profits and loss spreadsheet. And to your point, being able to use metrics as a tool to inform yourself but not become obsessed with to the point where you're everything happening in your community. If there's a dive in engagement it's very like, "Well, this is about me. What did I do?" And in reality it's like, "Oh, it's the holidays. It's going to nose dive right now. People are enjoying their families."

I'm not going to frantically message everybody to be like, "What are you doing? Did you see this post?" Because this is just traditionally in our culture anyways, a time that people do actually log off. And that's a good thing, right? And I find a lot of community-

Tom: How dare they, right?

Jillian: How dare they. I have been working on this post for an hour and I want recognition. No. But I've worked for companies in the past where they're just metrics obsessed. And in a way it ruins the community because you're turning it into this machine and it's like these are humans, these are people.

Tom: The funny thing: often when you really get people to deploy self-awareness on their own behaviors, they don't act the way that they want their members to, right? And this goes outside of community. This goes for audience building and social media. People will say, "Why are people not commenting all the time and engaging crazy." And then they jump on their own Instagram feed and mindlessly scroll through and don't double tap or comment on a single post.

Jillian: Oh, my gosh. Yes.

Tom: And the same thing with community, right? They're probably there too busy in their own life to really log in. And if they are a lot of them are going to be passive members. Yet in their own community everyone should be a power user. It's not realistic.

Jillian: Oh. I just want to get that printed on a billboard and put it in Silicone Valley.

Tony: I've noticed also I've dealt with a lot of challenges, coaching and consulting community builders. Especially IRL ones about how do you engage your community when nobody wants to be on Zoom, you can't be in-person, and everyone's freaking out because there's a pandemic or something. And recognizing that you don't always need force lots of engagement down people's throats. Maybe there's time when it's okay to not engage.

Tom: Yeah. I totally agree. And something I'm trying to do at the minute is structure my communities in a way that serves all different types of members and serves members as they transition through different behaviors. So what I mean by that is, we will have live events that are very heavy on interaction. We'll have live events that are more passive. We will have interactive spaces in our Circle forum.

We will have a knowledge space in our Circle forum where people can dig in and learn at their own pace and all kinds of other areas. And the whole point as we're catering for people that may be in a mood where they want to quietly learn at a time that suits them. And we're catering for the crazy extroverts in the community that just want to see other people's faces and everything in between. And I think where it's dangerous is where you just offer one or two of those things and you neglect entire sways of your membership.

Tony: Yeah. Absolutely. No. It's—

Tom: Actually, I have a question for you guys if I may. This is something I'm thinking about a lot. I don't know if you can reveal or if you've got any plans at SPI with this.

Jillian: Go on.

Tom: I'm looking to repurpose and repackage some of what's happening in the community and make it available to people outside the community in different ways and different tiered products and so on. Because I recognized that there's a lot of value in there, but not everyone wants to be tied into a subscription, not everyone has time to participate in a community. Some of them would pay to sit on one of our community workshops that was sold as an isolated webinar. Or if we got our whole knowledge based on the community put it in notion and put that behind a paywall as two examples.

Jillian: I mean, it's similar. So we've talked about creating programming that's live, that's public but that our pro members have free access to and otherwise is paid. So let's say we want to do a webinar or a fireside about a topic or something like that, anybody in our paid community has free access. If somebody outside of that community would like to come there would be a paywall.

And we've talked about the structure too of what if it was something with our team, with Pat, whoever and then the people who could be interacting could be our members, but anybody could watch it. So people who could ask questions or have conversation or discussion would be members of our community. But then we would stream it and so other people could consume it, but they wouldn't be able to interact on that level. We've talked about that.

Tom: Yeah. It's interesting, right? Because it fits the models on social media pillar content being redistributed into micro content. It also fits the models, which I know you guys do at SPI where you have your high ticket things and your low ticket things because you're catering to different people at different places.

Tony: Yeah. I think what you're getting at, Tom, is a really interesting thing that I've thought a little bit about which is just noticing, "Man, I'm in this room where there is so much value being exchanged." Or I just wrote a comment in a thread that is so good that I feel that could be its own workshop or product or something. And so how do you capture all this value being generated all the time in a internal community? Certainly obviously without compromising the value of that community to the customers in that community.

But breaking some stuff down into more bite sized, accessible pieces.

Tom: Yeah. Imagine you do a live workshop in your community that's an hour and a half. Some people can't make that time zone, or some people just don't have the schedule so they want to watch the replay. There's other members that want to watch the replay, but don't have an hour and a half to spare. And so what if it then gets cut up into a text format or a summary bullet point. So whatever it might be. So again you're meeting people where they're at in all different formats.

Tony: Yeah.

Jillian: I think it's a great idea. I think where things like this get tricky. And I'm not saying this is what you're doing. Just in general for the audience listening is when the content provided is from either a member or something like that and then you're turning it into a paid product, it gets gross. But if it's you and your team and you're presenting a workshop, absolutely. I mean, it's your content, right?

So I think where the fine line is, I know that your membership provides more value than just the content of that workshop. So you're not going to lose members who are like, "Well, I don't even need to pay for this because I can just get all the information from this snippet product." Or whatever it is you make from it. But, no. I mean, I think it's a great idea. You should try it.

Tom: Yeah. It's like a live brainstorming session now. I like it. Yeah.

Jillian: Yeah-

Tom: I'm kind-

Jillian: No. I love it.

Tom: Because I'm already doing it within the community and that's working super well providing these different formats. But now I'm like, "Well, should I repurpose these outside the community?" Because like I say, "Not everyone loves a subscription, et cetera."

Jillian: Yeah. I think it's definitely worth a test, right?

Tom: Yeah. Most definitely. I mean, I'm very bullish on Circle and events and these different community model. I'm still a bit of a new with Discord. I'm more of a user. I haven't really run Discord on communities. And so I said to one of our members... They posted a little paragraph about Discord. I was like, "Wow, you seem to know your stuff. Do you mind doing a new post outlining some tips?" They wrote a freaking dissertation on Discord.

Which actually Jay on your team was posting about. I then got the member's permission to sent the summary to Jay who was like, "This is gold. This is so in depth." And I think that just speaks to the power of again, there's different perspectives, different expertise. And you not having all the answers, even in your own community where you might be the expert.

Jillian: I would to see that post.

Tom: I'll send it to you. I'll get their permission again.

Jillian: I would love to see it, yeah, if they don't mind. Because I am a Patreon member for a few creators and they all have Discord communities and I just don't get it. I don't get it. I mean, I guess if you're a gamer I can, but I just don't get it. It's like Slack but different enough that I'm like, "I don't understand this. Can we just do this on Slack?" And then I feel old. So I'd love to just-

Jillian: ... feel like I can be there.

Tom: I'd love to have this debate because we're really speaking to synchronous versus asynchronous communities. And I find it's very black and white with people. They seem to have a strong preference. And for me, I think why I love Circle is I really like forum structure communities. And asynchronous communities like Discord and Slack scare me a little bit. Because I go in I've lost track of where the conversation is at.

I feel like it's almost too demanding of me. I like to be able to drop in, get some value and drop out. Or contribute some value then drop out. But other people are the total opposite and they're like, "Forums are a turnoff. It has to be synchronous or I just don't engage."

Jillian: It's so true. I'm a Reddit lover. I like to lurk. Because as a community builder to be in a community, I mostly just sit on the side and I might comment here and there. But because it's what I do I know I'll just take it over if I get too involved. Because I can't help myself, right? So out of respect for the people who run other communities, I usually really hold myself back unless it's depending what it is. There's a couple that I'm all in. But, yeah.

I'm in a couple Slack communities and same thing I find, I don't want to be there all day, everyday. And so when I do log in it's just like, "You're so behind." Because people have these fun conversations that if you're not there for it and reading through it, it's just not the same as reading through a hilarious Reddit thread.

Tom: You know when I loved those communities, Jillian?

Jillian: When?

Tom: And sorry to interject. When I was 15, 16-years-old running my Interpol community. Because I didn't have a mortgage and a wife and a day job and a side hustle. So I could sit there all day long chatting for five hours about my favorite things.

Jillian: Right? Absolutely. Yeah. Well, and I'm in one that's a mental health startup one because I used to work in that world. And even that, right, it's a pretty dry... It's a lot of like, what's in the news, job openings, people hiring, that kind of stuff. And even that I'll go in there and I'm like, "Oh, my gosh. There's just so much in here. I don't even know where to start." Because I haven't been in here for two weeks.

Tom: Yeah.

Jillian: Yeah. But then our work Slack, because I'm on it 40 plus hours a week. We basically created a holiday movie that was West Side Story meets... I don't even know what. I don't even remember. But it was dogs in space. It was just this 60 messages of complete shenanigans that was so much fun at the time.

Tom: Do you mind if I just share a passing thought, if I may, about community?

Jillian: Please save me from this random disclosure I just gave the internet.

Tom: No I loved it.

Jillian: Yes, please.

Tom: So something I see a lot with community and the reason I want touch on this is I believe community is booming right now and will continue to boom. And whilst it's been around forever, technically I feel like we're still so early. And with anything that has huge wave, this bell curve, I think, a lot of people jump in without fully understanding it. And what I'm seeing increasingly is, "Oh, community's the hot new thing, or people tell me I should have a community. Therefore, I'm just going to jump right in with both feet and launch a community." And then invariably it fails.

And I think actually there's a huge amount of lessons in wider business and marketing. And this is, I think, why our community has been quite successful so far is because I was able to leverage what I've learned in business and apply it to communities. So things like getting a clear value proposition, defining your ideal member, validating. So my current community I said, "I don't want to launch this unless I can get close to 100 founding members." So when I validated it and got several hundred applicants so I was like, "Okay. This is good. But if I got 20 then it would've been terrible."

And then within the validation you have all of the discussions to ascertain what they want from a community like this. Do they want asynchronous or synchronous? And you can really get to the heart of their expectations and build around them. And it wasn't until I had done all of this that I then went, "Oh, yeah. I need to go build this thing." And I think people get it the other way around where they're like, "Oh, community, that's hot. I'm going to build a community. Shout about it."

No one's going to sign up. The people that do are going to trickle in really slowly and there's going to be no critical mass and they're going to leave because it's a catch-22 and it's an empty party. I mean, I'm sure a lot of what I've described to you guys see all the time, right? But it's such a common set of pitfalls and it's so avoidable if you just go through things in the correct order, rather than having it back to front.

Jillian: I see it all the time. And it's funny because I see two sides of it. So I see that side where people are like, "Oh, shiny new thing and I'm just going to do it." And exactly as you said, they spend more time thinking about the end result than the Onramp. And the Onramp is so critical for community to exist and flourish. But then, I see this with our members in pro that want to start a community and we often help them with just some steps to, well, ask people, start a waiting list of who would want to join, get an idea of who's interested, that kind of thing.

They're scared to start one because they're afraid no one will join. But then when they go through the steps and do it, their community is great. It takes off. And granted, I think, the barrier to entry varies depending on who you are and what kind of community. Whether it's 100 people to go or 20 people to go it can depend. So yeah, it is funny. I agree that, I mean, community is here to stay and it's just going to keep going. But a lot of the communities that are launching right now will not exist in the next year—

Tom: The majority, yeah.

Jillian: Yeah. Just because it's become a buzzword. And I think the pandemic accelerated because people were like, "Oh, I need community." And maybe created something that worked for when they couldn't leave their house for two months. So I think just the nature of that alone is challenging for digital community. Like Zoom fatigue, there's just digital fatigue.

Tom: You pretty much just described the trajectory of Clubhouse. So pandemic boom and then slam of—

Jillian: Oh, ouch—

Tom: Yeah.

Jillian: Yeah.

Tom: It's tricky. And I think people don't realize how much work community takes as well.

Jillian: No. And that's irritating me right now. You were talking the whole hustle culture thing, which I have a lot of strong feelings about that I'll save. But I think the same with this whole like now how people are trying to be like, "Oh, I'll teach you how to launch a community and make it super profitable and blah, blah, blah." And just the skeezy people selling course type things.

And we sell courses. So I realize I'm talking about specifically the people who are trying to sell you the idea that community is easy and highly profitable. And it's like anybody who tells you that don't give them your money because community is... It's not hard, but it's ongoing. It's always ongoing. You don't set it and forget it.

Tom: You have to be consistent. You have to show up. You have to spend a bunch of these. I'm curious what you think Tony and Jillian. But I actually think it would benefit a lot of people to start by running a membership site before running a community. Because if you've never run either that teaches you a lot of the fundamentals, right? You can look at providing value. How hard it is to get people to sign up and pay for something. How to deliver that value. The marketing that goes around it, et cetera, et cetera.

So a lot of that stuff will carry into community. But if you've never run either, you have to learn all that stuff. Plus managing relationships at scale, connecting people and all the human element of community. And I think that's where people get extremely overwhelmed.

Tony: That's an interesting approach, I think. I've looked at it in terms of breaking it down first with learning how to do event programming, which is community gathering activity a la carte before you commit to a ongoing community. But I like the idea of that direction as well where learn how to maintain a membership organization and then learn how to get good at community. I think if you have the inclination it's not a bad idea.

Tom: It's a tremendous point with events though. You're totally right. It's so fun to essentially run a community space for two weeks and it's very high pressure. But a lot of people, I think, will come out of that thinking, "Phew, I don't want to do that 52 weeks a year. That was exhausting." And then they get that reality check of, "Okay. If I do this long term, how am I going to do it sustainably?" Probably at a lesser extent than what an event demands of you.

Jillian: Yeah.

Tony: Oh, boy.

Jillian: We host a lot of events. A lot. And they're more hour long join to Zoom. Whether it's a meetup about a specific topic or we have an expert come in and it's an ask expert, that kind of thing. It's not like running an event like what Tony was alluding to in his co-working past life where it's like beverages and speakers and in-person and much higher touch. So I'm not trying to take away from that.

We're in a place now where we opened up member led events. So members can submit an event and host it and we put it on our calendar, and it's like a pro event but member led. And it's just taking off. It took a while. It was a slow start but we figured it out. A lot of it was talking to people being like, "Oh, I didn't know I could do that." And being like, "Okay. Let's talk about that because it's in six places on the site."

What questions do you have? Anyways, it's just that journey. It's that ongoing work and investigation and figuring out like, "Oh, this thing we launched could do better."

Tom: Do you sit in with them or they lead the whole thing autonomously?

Jillian: We have a checklist for them to fill out to be like, "What is the event? What's the description? Is this within our community guidelines?" You can't sell. It can't be like, "It's a webinar. And, no, buy my course." You know what I mean? So we gut check it. If I can make it to one, I will. But we trust that they're just sharing knowledge with each other. Yeah. It's amazing.

Tom: Yeah. I love what I'm hearing there. And we're shifting towards similar things. So we do deep dives with members. They're not leading the whole thing because I think they appreciate the support but it's like I'm asking questions, but really they're the one sharing their journey. And I'm curious actually, both of your thoughts on this. So when I define value propositions for community, I believe that the strongest value propositions are predicated in transformation.

Because I think what a lot of people do is they list features and they say, "Oh, you should join my community because we have this many workshops a month and we have these features and we have this forum and da, da, da, and these eight bonuses." And I think that doesn't grab people. I think that's fine to have further down your landing page. But I think the umbrella value prop is being a member should take you from point A to point B.

And where I think it's interesting to have member generated content is when those members that are one step beyond where other members are. So, for example, in our own community we have the transformation of doesn't have a community wants to launch one. And we have runs a struggling community and wants to run a thriving community. And so we see that as members tip over into going from prelaunch to actually having a successful launch, that's when we can empower them to inspire other members, be it through a deep dive or a Q&A led by them.

And I think that resonates more than like, "Here's Tom sharing what worked seven years ago on one of his previous launches." It's like, "Well, here's one of your peers that did this last week and was literally there a month ago discussing with you the anxiety around launching that you both share, but they've overcome it and they've launched and what lessons can you learn from them being just one step ahead of you." I think it's really powerful.

Jillian: It really is. I think it's time to do some rapid fire. Tom, how do you feel?

Tony: It totally is time.

Tom: Terrified, but excited.

Jillian: All right, Tom. When you were a child, what did you want to be when you grew up?

Tom: Oh. When I was really little something involving dinosaurs because I was obsessed. When I was a little bit older I did the lame quiz thing they give you at school where it spits out what career you have and ironically, I think, it was a tie between advertising and graphic design and I run a company that markets people's digital design products. So it was pretty close.

Jillian: Were you devastated by that response wanting to be an archeologist or Jurassic Parkesque person?

Tom: I'm still trying to figure out a way to shoehorn the dinosaurs into the current company. I haven't got it yet but, yeah, I'm just hoping.

Jillian: There's time.

Tom: Yeah.

Jillian: All right. Tom, how do you define community?

Tom: I wondered if you were going to ask me this. I think the whole point — and I've heard you ask this on the show before — is that there doesn't seem to be one true definition.

Jillian: There's no wrong answers.

Tom: Yeah. I think really it has to be a spectrum. Because I think what I've seen some people do is say, "Here's a 12 letter acronym and if it doesn't abide by every single part of this, it definitely is not community." And I think it's much more a sliding scale than that. So I think you get community in a sense of a closed community, which I define as many people being able to talk to many instead of one talking to many.

But then I think you can also get a sense of community where people feel part of a shared vision or ideology, et cetera and then there's all kinds of different stages between that. And I think, for example, with company, yes, we have a Circle community, yes, we have Facebook groups, yes, we have events. But before those things were launched, people absolutely were talking and saying, "I'm a part of the community. I'm a community member." And I don't believe that turning on one platform suddenly creates community where there was none.

And I think it's there the whole time. It's just that you need to create spaces for that community to fill. So yeah. Hopefully that's not a wishy-washy answer. But I think it's a sliding scale and trying to pigeonhole it into one strict definition is problematic.

Jillian: I like it. I mean, it's the hardest, easiest, hardest question to answer.

Tom: Yeah.

Jillian: Whether or not you have an actual bucket list in that lens of thinking, what is something that would be on your bucket list that you have done in your life?

Tom: I think this is not going to sound a wildly ambitious one, but we moved out to country last year. And I'm a big believer in trying to create your ideal life rather than let life happen to you. I know that sounds cheesy like you're manifesting it, I guess. And I think through being intentional in that, we now look out the window and see horses every morning and we have a happy little golden retriever. That's the soppiest dog in the world.

And all of these things didn't happen by accident, it's because we were intentionally trying to shift towards it. And so definitely we've been here over a year now and everyday we sound like a broken record just like, "We're so lucky to live here. We appreciate it so much. We're so grateful." And I think that was a big bucket list thing where younger me could only have dreamt of that setup.

Jillian: I think you're really selling yourself short. That's a huge bucket list accomplishment. It's like your entire life. That's your every day for this part of your life. Okay. So what is something on your bucket list that you have not yet done but would like to?

Tom: I want to direct an Indie film.

Jillian: Ooh.

Tom: So I am so film obsessed. I did film as my minor at college. And it's one of those things I'm just too busy running my companies and all that stuff. I never have time and it takes a lot of time to do it properly.

Tony: So, Tom, we normally ask our guests what is a book that they are either currently reading or just an all-timer that they just want everyone to know about. I'd love for you to answer that one.

Tom: Cool books. I'm going to shout out one of your previous guests, I believe. So. I recently read The Business of Belonging by David Spinks. And the reason I love it, I'm really not very good with generalisms or vague theory. I'm all about actionable practical advice. And also I really learn from seeing how other people are doing it with real life case studies. And it sounds terrible. I'm almost always disappointed by books because of that volition where I'm like, "Ah, that was fluffy." And that book was just pure action.

And a lot of it was stuff that I was doing, but I was nodding along because it was so validating and then other stuff that was nuances in bits I wasn't doing. And I was like, "That's genius." So, yeah. Respect to David for writing that.

Jillian: I felt very similarly.

Tom: Yeah, it's great, right?

Jillian: I was like, "Yeah, that's right. That is how you do that." It was very validating. I was like, "I do know what I'm talking about."

Jillian: This question is going to be hard for you because I think you already really love where you live. As you said, very intentionally move to where you are. But if you could live anywhere else in the world, where would that be?

Tom: Loved Italy when we went pre-COVID. Just driving around Tuscany is insane. So that would be extremely high.

Jillian: Okay. Final question, Tom. How do you want to be remembered?

Tom: I had to try so hard there not to quote David Brent from the UK Office. Where he’s like, “simply as the man who put a smile on the face of all who he met,” I won't go there. Yeah, it sounds cheesy, but I want to be remembered as someone that gave more than they took at scale. And so, yeah, I feel like we've had a real positive impact through my company with what I'm building with my personal brand and in the community space.

I want to inspire a ton of people to start communities in the right way. I want to try and guide people to do it with kindness and honesty and empathy and the SPI approach. I think you guys are incredible with that as well within what's widely regarded as quite as the sleazy industry in many ways. I think there's organizations such as yours that get it so right who I massively respect.

So, yeah, just that scalable, positive impact. And I believe that community and entrepreneurship can have such an impact because it ripples out, right? And even at a micro scale, nothing's more exciting to me than running up to my wife and saying, "That guy we've been helping, he can pay his mortgage now." And when you magnify that by an order of just thousands and thousands, I think it's the most exciting thing.

Jillian: Oh, absolutely. You want to serve first. That's what we say.

We made it. Tom, let our audience know where they can find you, and especially if they're interested in learning more about your communities.

Tom: Sure. Well, thank you again for having me on. This was actually super fun and the questions were not too terrifying. My Community for Community Builders is Learn.community, which I am still so pumped. I got the domain for earlier this year. And my personal website is tomross.co where I blog every week about community and try and make it super practical for people. And then I'm tomrossmedia across all the socials. Oh, and I wrote a giant free book about community, which you find at CommunityManual.com. And I have too many links these days, is my takeaway from that.

Jillian: Amazing.

Tom: Yeah, seriously. Thank you, guys.

Tony: Thank you, Tom. It's been such a pleasure.

All right. So that was a conversation with Tom Ross. And, oh, it's so grateful just to hear somebody really, really tell the story in such a forthright way all the way through the ups and downs and coming out the other side thankfully in one piece.

Jillian: Yeah. Yeah. I can't imagine going through what he went through, but then having the gumption to put it out there and be like, "Look, I wrecked myself and this is what I learned from it." I appreciate his candor with it.

Tony: And word of warning to folks who are listening, if you're building something and it's starting to work and you're starting to feel this really strong feedback loop of this thing's growing and it's making me more excited and more ambitious, just try to remember that these stories exist, check yourself, keep an eye on what's going on for you.

Jillian: Yeah. I mean, and it's tough because there is healthy growth, sustainable growth. And then there's that very faint line where it crosses over into toxic and burnout and what happened to Tom.

Tony: And then treating people like humans. I think that helps keep you in check too, that if you're not talking about your users or your members purely from a statistical standpoint, but you actually have some decently meaningful real relationships with some of them, then that helps you stay rooted and helps them keep you rooted too that they can call you out if they see that you're a little bit off kilter.

Jillian: Something along the lines of that, the remembering people are human, remember that you're human. You too are human. And just the empathy to self is important. If you're feeling super burned out or you're starting to physically feel sick, take a day. Do what you need to do.

It's funny, because we talk about rituals in community and how important it is to have ritual, whether it's a digital community or a group that you're a part of. But it goes back to that empathy to self and self care. Creating a ritual for yourself, whether it's a daily ritual, whatever it is. Maybe it's, every hour I'm going to stand up and walk around for a minute. It can be something so simple.

But if you create a ritual for yourself that is under this self care umbrella, it goes a long way.

Tony: Well, one of the important pieces of that is that this is not uncommon. There's a good chance that, especially if you're a community leader, everybody else in your community is dealing with similar challenges. Is your community the community that wouldn't mind trying to do a little self care checklist together? That could be fun. That kind of segues into a conversation about empowering the members of your community to have more involvement in the leadership and in the running and growth of the community.

Jillian: Yeah. I think Tom was so eloquent with it and it's something I feel like that comes up all the time because it's just absolutely fundamental in community. You shouldn't be doing everything. People within your community should be participating. And if participating to them is like, "Hey, I'd love to host an event." People get excited and want to be involved. But also just giving people the space to start conversations and have them.

Tony: Always a smart move to have more people involved. A community is not a thing to be provided by a person. It's something that might be facilitated by a leader.

But the value that people get comes from the people who are in the community. And your job really is to try to be more of a facilitator than a giver. And hopefully that helps you set yourself up to be in a better place for the long run as well.

Jillian: 100 percent. We see it in our community a lot, and it's wonderful.

Tony: And at the same time you're recognizing that, "Hey, if I'm running this community, it's a business." The people that are becoming empowered, this team of power users, they're not necessarily going to be around forever. They're not necessarily going to all show up all the time. It's the nature of volunteers. And so having those roles be clearly defined, really thinking through the flows of, "Okay, if I'm going to have a volunteer power user member do something, how do I make it very easy for them to keep doing it and very hard for them to want to quit?

And at the same time, how do I make it so that they can gracefully exit when it's time for them to because I can't expect people to volunteer for me forever in any context?"

Jillian: I really love the time cap and that the expectation is set from the get go. If you're going to be a guide or whatever role name you have for these power users, ambassador or whatever, it's three months, here's the scope, here's the criteria. And then whether or not you want to allow people to re-up, if you will, to do it again for another three months or whatnot, I just love it. But just also giving them the freedom to do it the way that works best for them and make it fun, right? There's nothing worse than over complicating a role. And then it's work. People don't want to do that. You're not paying them, so make it fun.

Tony: Yeah. We're allowed to have fun as, especially if it's something of our own creation. Sometimes I think we need to give ourselves permission for that. So let us know what's on your self care checklist. Let us know how you're giving yourself permission to have fun as you build your community, and let us know what's on your mind, how this story reflected for you, how it landed for you. We're @Team SPI on Twitter. And we'd love to hear from you. So in the meantime, until the next episode, go build community, take care of yourself, take care of each other and we'll see you next time.

Jillian: We'll see you next Tuesday.

Tony: This has been the Community Experience. For more information on this episode including links and show notes, head over to SmartPassiveIncome.com/listen.

Tony: All right. You can learn more about Tom Ross and all of his great offerings at TomRoss.co, T-O-M-R-O-S-S.co. Look out for his community offerings on that personal site. You can also find him on Instagram and on Twitter @TomRossMedia.

Tony: Our executive producer is Matt Gartland. Our series producers are David Grabowski and senior producer Sara Jane Hess. Editing and sound design by Duncan Brown, music by David Grabowski.

Jillian: See you next time.