Digital Insiders Event #13 In The Books - Here's A Recap!

Julie Chenell recaps Digital Insiders Mastermind #13, a three-day event with 85 online business owners. A standout exercise had members design a time-travel tourism company to practice positioning. Evening sessions created space for vulnerability, with new members feeling genuinely welcomed into the group.
Welcome to Million Dollar Grit, the podcast that dives deep into the world of entrepreneurship, where tenacity meets strategy and dreams meet reality. My name is Julie, and I explore the raw, often overlooked truths of what it takes to succeed in business and in life. It's not just about the glossy success stories, it's about the grit it takes to get there.
Hey everyone, this is Julie, and today I'm taking you sort of behind the scenes of the Digital Insiders Mastermind, which happened last week, and this was my This is my 13th event for Digital Insiders specifically, and I wrote a post on Facebook, you know, at the end of the week saying that it feels like I'm 7 years in and there is this sense of ease and flow that is happening in this year that really hasn't been there until this year. And that's not to say that the years prior weren't amazing because they were, and every single mastermind has its own sort of unique dynamic of people and location, but there's something something about the flow and ease, which, you know, I don't really know how to describe it, that made this one my most relaxing event ever. And when I'm relaxed, I can, I can definitely connect more and kind of put down the clipboard and put down the, the part of me that's sort of running the show and really connect with people. And so that was really fun for me. So for those of you who have never been a part of a mastermind, A mastermind at its core is a group of people that have something in common, even if they are very different. In this case, the commonality is that we are all online business owners and we get together for the sake of sharing ideas, sharing knowledge, tactics, strategies, failures, and sort of having discussion around these ideas in hopes that everyone at the table gets something to take home with them, whether it's an inspiration, whether it's, you know, getting through a block. And that's really the goal of a mastermind. And so our mastermind has about 85 people in it, and we usually see anywhere from 45 to 65, 70 people show up for these events. So it's enough people that you're really getting that like hive mind, but not so many people that you're getting lost. And if you've ever been told, you know, you should do events to, you know, you should go to events to get to know people. I think masterminds are the best return on investment of any type of event. You have retreats which are amazing, but they're really small. So you, you know, assuming that you hit the right retreat, those can have an amazing, amazing return on investment. You have the really, really big conferences like Traffic and Conversion. Those tend to have a lower return on investment unless you're very, very diligent about seeking out the right groups people, but then there are these masterminds that have, you know, somewhere in the ballpark of 50 to 100 people that every time I've gone to one or I've hosted one, the return on investment from ideas to collaborations to clients and students, it's just, it's hard to beat. So I encourage you to consider a mastermind or two or three. If you're the kind of person that doesn't like to run Facebook ads or you like to do more organic marketing, put your marketing budget towards a mastermind and join a mastermind cuz you'll get a lot out of it. So our mastermind runs 3 days, Tuesday, Wednesday, Thursday. People arrived on Monday. We had a happy hour on Monday evening at this little pizza place down the street called Bar New Haven, famous for their mashed potato pizza. So there were about 20 to 30 of us there just saying hello. And then we kicked it off, uh, Tuesday morning at 9 o'clock. I gave everybody a set of 5 questions to fill out. They were supposed to write them anonymously and they were kind of funny questions. Things that you wouldn't necessarily ask in a networking environment. So things like, you know, hey, the economy collapses and there's no internet and we have to start a business. What kind of business are you starting and why? Or you just got a book deal. What's the title of the book that you're gonna write and why? And so all throughout the week, I read aloud during breaks and stuff like that. I read aloud these sheets and people had to guess and kind of see who, who's who in the room. So that was a fun activity. And then we had basically 5 presentations a day from members, 1 presentation a day from myself. And then in the afternoon we had some sort of either workshop, coworking, roundtable, something like that. So interestingly, the first keynote I did was talking about prioritization and realizing how much of a struggle it is for a business owner to prioritize what is the next right thing to do. and I wanted to do that at the beginning of the week because I knew that people were going to get lots of ideas and then they were going to be wondering, okay, which one should I, you know, which one should I go with? And so I did this presentation on how to decide when to pursue a new product or funnel and how to make that smart decision. I taught for about 30 to 40 minutes and then we hot-seated a few members and we had them come up with their particular problem. And here's the takeaway. Very few people think with the problem in mind. We often as business owners, we're visionary. We think with the idea in mind, right? This would be cool. Oh my gosh, I see this, right? We can cast vision. But my first exercise in that, in that training was, hey, what is the problem that you're actually trying to solve? And it's funny, people talk about it and they don't necessarily identify it in problem language. And once you do, everything comes much more into focus. Another takeaway from that presentation was that many of us build in ideal circumstances, right? We imagine our ideas in the lab of, you know, no fatigue and no existing client work and no small children. And, you know, we, we think, oh, I have plenty of time to do all of this. And then we realize that we're not imagining this in reality. We're not actually seeing what the lift is gonna look like in our real life. And that's a big mistake we make where we get halfway into projects and then crap, we we realize, uh, we didn't necessarily think that through all that well. So in the afternoon, we did an amazing exercise called, um, well, it was a time travel exercise. Basically, I divided everyone up into groups of about 8. Actually, Helen organized the groups strategically based on personality. So we did groups of 8, and we gave them a prompt, which was, hey, the technology for time travel has been invented. And you are going to launch a time travel tourism company. What are you gonna do? We left it very open-ended. We gave them poster board and markers and stuff like that, create an offer. But the way they had to present it to the group was they had to present it with, um, basically an org chart. Who— every single person in that group had to have a job and a position and a title, and they had to present. So 6 groups presented, and I couldn't have like concocted this or choreographed this if I tried. It went totally, you know, in a way that I didn't quite expect, but it was fascinating because we had 4 groups build a time travel company that kind of solved the same problem, which was, hey, you want to go back in time and do something over, you want to go ahead in time and see something that, you know, you don't think you're going to get to see. And they all kind of circled around that problem. We had one group that circled around a more niche problem, which was like, hey, go back in time just like 15 minutes or 20 minutes and like don't say that thing you were gonna say during your pitch or change that ad or change, you know, it was very business focused 'cause we were at a business mastermind. And then there was one group and they chose a very niche idea, which was, hey, go back in time to the concert that you would love to go see. You know, would you love to go see Elvis, for example? And so everything about their package was around this going back in time. And when everyone presented, they definitely weren't the team that was the most organized or presented the best. However, they won by a large margin because we all voted, because everyone felt that the positioning and the messaging was so powerful because of how specific it was. And so this— I didn't intend that that was going to be sort of the big aha, but there was this sort of moment in the room where people realized, man, it— everybody was fighting for this, you know, market corner of like, go back in time and do a do-over. And this team won by a landslide because of how specific and powerful the messaging was. So that was an amazing activity. People got to know each other. It was fun. And then that night we, we munched on Spanish tapas and paella and meat and desserts and drinks. And we had a fantastic time at Barcelona, and that was just day 1. And so the days continued onward, and, uh, presentations were amazing. There was like everything from HR to Facebook ads to YouTube to mindset, and it was really a very, very incredibly powerful week. What we do on Thursday nights after the dinner is we do sort of an aftermind, and this is an opportunity for people to shout out other members of the group It's always intense, it's slightly emotional, but the overarching theme of that night was how much people need to feel seen. And not seen in their perfect, like, Instagram-worthy way, but seen in the, like, hey, I failed here, or hey, I'm not doing what I thought I would be doing, or hey, I'm in this messy pivot. And that was repeated over and over when people would stand up and speak to others in the room. It was always about being seen and being heard and being listened to. And it was, it was definitely an emotional, emotional night. And we had more new members at this mastermind than I think we've ever had before. I think there were, you know, 10 new digital insiders in the beginning of 2024. And so I knew this mastermind was going to have a big scoop of people that didn't know anyone, and they all said that they felt like there was not a hint of any sort of cliques or, hey, this is the— these are the OGs and we're the newbies. They said they felt welcomed, invited into the conversation right away. There was no sense of like, oh, you haven't been here long enough. And I, of all the things that I am proud of, there are many. But that is something that I am very, very proud of, that new folks in Digital Insiders are welcomed, uh, with the same enthusiasm and the same respect and admiration as someone who's been there 3, 4, 5 years. So I came home on Friday. I cried for hours. I think it's just— I don't know if it's a release of adrenaline or sadness that all these people that I, you know, spend so much time with go back into my phone for another 6 months. But I had epic meltdowns about all kinds of non-important things. But I know now, I know that that day is always an emotional day and the next day it gets better. So I'm recording this on Monday after the mastermind and I have a bajillion things to do and podcast wasn't on the top of my list, but I thought, you know what, I wanna capture the moment while it's here because I'm gonna start talking about some of the things that, uh, we went deep on more in depth here on this podcast and I also want to extend an invite out to all my podcast listeners. So back in 2021, I had this idea that I wanted people to be able to kind of taste test what Digital Insiders was like without necessarily having to sign on the dotted line right away. And so I hosted this thing called CEO Week, and I invited people who are not yet Digital Insiders to come to my home and experience what it would be like to be, you know, in a hot seat with me, coaching with me. And I called on some Digital Insiders. I said, said, hey, I have about 4 people coming to my home and they're coming for, you know, these 3 days, and I would love some insiders there so that they can get to know the group. And I think we ended up with 5 people in the house that week that were not on NDI, and then another maybe 20 digital insiders, and 4 out of 5 of those people ended up joining. And so it was a great taste test. Well, the past couple years my life has been a little bit up and down, and so we've done CEO Week, but I've never opened the doors back up to non-digital insiders before, just because I felt like I have to really, like, be focused and on my game. And in 2022 and even in 2023 a little bit, I was still kind of dealing with the fallout of my divorce. But I am really excited for this year's CEO Week. It is July 17th, around there, somewhere in that week. I got to get the actual dates and I have 30 digital insiders that are planning to come. That's technically like 27, and I can handle about 30 to 31 people at max. So I'm going to extend an invite out to my list for 3 or 4 people that think they want to join DI, but they're not quite sure and they want to come to Connecticut. I charge, you know, $2,500 for the week. It's a Tuesday, Wednesday, Thursday, so that would be the cost. You could come be an honorary DI member for those 3 days, get to know people, get to know me, and then decide if you want to and we actually put that amount towards your investment in Digital Insiders. So if that sounds like something you want to do, please hit me up. You can DM me on Instagram, you can email me julie@juliechenell.com. And over the next several weeks on this podcast, I'm just going to start sharing some of the things that I've been teaching in Digital Insiders, what I have been learning from coaching people in all different markets. And so if that's something that you're interested in, digitalinsidersmastermind.com. You can go in and put in an application there. As always, thanks so much for listening, and I'll talk to you soon.
And there you have it, folks, another dose of Million Dollar Grit. I hope today's episode has left you feeling inspired, equipped, and ready to face your own entrepreneurial journey with resolve. Remember, until next time, embrace the struggle, harness your grit, and keep pushing forward. You're stronger than any challenge you face. I'm Julie, and this has been Million Dollar Grit.
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