What I brought home from the 17th DI mastermind

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 Chenell, 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 Chenell. Welcome back to Million Dollar Grit. Today I'm going to give you a recap of the 17th Digital Insiders Mastermind. We just got back from New Haven. We spent 3 days, there were about 40 of us in the room. Amazing experience as always. I keep saying they get better and better. I don't know how that's possible. And I wanna take you through a whole bunch of aha moments and insights from that room. And to just kind of give you a little bit of a backstory context, what is Digital Insiders? If you are just new to listening to this podcast, Digital Insiders is a hybrid of a coaching program and a mastermind. Everyone in the room has private coaching with me, and I am a pretty high-touch coach, so I know everyone in the room very well. They get access to me and they get access to two additional coaches, Helen for nervous system, mindset, personal development, and Nuno for tech. And twice a year we do these masterminds. They're 3-day events. The one in the spring is in New Haven. The one in the fall is at a destination, usually on the East Coast. And this is when I bring all of these people together and we do a combination of teaching execution, integration, hot seats. You know, every single mastermind is a little bit different. I usually get, like I said, anywhere from 30 to 60 people in a room, and a lot of deep relationships have formed. This mastermind has been going on for 9 years, and there are some members that are original, which is crazy. And this mastermind especially had some cool differences from other masterminds because of the way I was able to architect the event, given that I have so much deeper understanding and knowledge with having AI to help me. Whereas in the past, you know, I understand that there are patterns working through the group, but this time it was very, very obvious that, uh, Claude had helped me significantly figure out what tactics was— were going to matter. All right, let me go ahead and dive in. I want to talk first about my decision to bring someone into the group who was not yet a Digital Insiders member. I hope he becomes one someday. His name is Michael Roderick, and he gave a keynote talking about the difference between aspirational and excellence buyers. The reason I chose him is because that there are a bunch of people in my group who are serving a certain customer and they don't want to serve that customer anymore. They want to serve service a different customer, and usually it's a more high-end customer. And Michael's talk about aspirational versus excellent buyers really helped frame how to speak to the different types of audiences that you have. Now, aspirational buyers are in survival mode, right? They are looking for a way out of their predicament, and when they are evaluating some sort of purchase, They think in the context of spend and then speed and then status, right? Let's just take an example of someone who really needs to make money online and they come to your webinar and your webinar teaches how to become a bookkeeper. Okay. Their very first question is going to be, well, how much does this cost? And how fast will I start making money? And then they think, okay, and if I invest this money and I become a bookkeeper quickly, will I be like this star student over here? Right? So it's spend, speed, status. And what Michael was explaining was that excellent buyers operate from a little bit of a different, uh, vantage point, right? So excellence buyers are buyers who are pretty in touch with the problem that they have. Okay, so let's take this exact same example here, right? And let's say that it is a bookkeeper who's already making I don't know, $5,000 a month as a bookkeeper, but they're finding that they're getting really stressed out with the delivery and the operations of their business, right? And they, they understand that their problem was created by success in a way. And then they stumble upon you and they notice that you're a bookkeeper with 50 clients making $100K a year. And their first thought is, I want to be like that person, right? So they think status first. They think, How do I get there? Because right now I'm drowning. Then they think speed, which is how fast can I get my operations like her? And then the last question they ask is, okay, well, how much is this going to cost? And it's not that one buyer is bad and one buyer is good, although I'm sure you can see that one buyer might be a little bit more broke or desperate or looking to you to save them, whereas one buyer might be easier to close and not looking to you as a savior. But there is sort of something in the middle, right? So there's aspirational buyers, which are like, okay, I, you know, I need this to work right now. There's excellence buyers, which are solving problems caused by success. And then there's excellence— excellent curious. And this is that thin slice where you have people who are kind of moving out of survival mode and are thinking about like, what would it be like to be successful? And they're willing to put in the work, and that's actually a really great market as well. And so he talked about that. He also talked about, about a bunch of other things. He talked about the 6 currencies of value, and, you know, we often think of time, connections, and money as currencies, but he had 3 additional currencies. And he also spoke about the Triple Threat Talent Framework, which so many people in the group resonated with and He comes from the Broadway world and talks about the triple threat of singer, actor, dancer, and he said there's a triple threat in business. It's scientist, celebrity, magician, and understanding which is your talent or strength first, second, third, right? So the scientist is very much about teaching and details, and the celebrity is very much about charisma and energy, and the magician is very much about novelty. And I'm summarizing, but Michael Roderick, he's a great person to follow. You can find him on LinkedIn. He opened the event and that was really fantastic on that day, on that day one. We also had several people share. So these are people in the mastermind who shared for about 30 minutes. We had Emily Green. She is an expert in ads as well as low ticket, and she was talking about some of her clients who run these $15 workshops and then end up selling you know, $400,000 in sales. And she really likes those $15 workshops because of the fact that it's building a buyer list and also it allows you to liquidate that ad spend. So she taught that. Amber Housley, she taught on her, uh, her journey of a weekly live webinar. She talked about what was, you know, at least probably a year of struggle. But it really was so inspirational for people who have felt like, okay, the webinar's not working for me. So she went through her entire journey. She did 34 webinars before it started converting. And I can just say that number and you could probably be like, oh wow, that's a lot. But like, I want you to actually imagine 34 webinars, 34 weeks, right? How long is 34 weeks? It's a, it's a long time. And the later ones obviously started to convert, but now she's got a high-converting webinar on repeat, and just the struggle and the persistence that showed what changed in her business when she stuck with this, and that was really, really inspirational. Then Aryeh Sheinbein, he actually told a deeply personal story about a credit card debt debacle, if you will, and I mean, he had the room captivated, and he known in the money space, and he talked about the important lessons around your credit score and debt, which, you know what, is a really candid conversation that we need to have these days. A lot of us have credit card debt, we have loans, and he kind of broke down the story and really showed people that some of the things that you fear the worst are actually paper tigers once you finally go through it and you realize that you are so much stronger than you thought you were. And then Brittany Long, she taught about how she can deliver a fully done-for-you funnel in 60 minutes using Claude. And now Brittany is the fastest person in the West is like what I like to say. And she was saying, okay, you know, it used to take 6 to 8 weeks to build a funnel. It used to take me 10 days and now I've got it down to an hour. And she sold a whole bunch of these done-for-you funnels in 60 minutes for $997. She walked through her process. Obviously she uses FG Funnels. That. Was day 1, you guys. It was— so day 1 was a lot of input, right? A lot of cool tactics and strategies. I ended the day by helping people understand, okay, what did you come into the room with? What were your ideas? What were your hopes? What were your dreams? And then what did you just hear that's like rattling around in your head? And then we did a 3rd exercise, which is, did anything you hear match what you came in with? And the reason we did that was because I think some people can come in with an agenda or an idea of what they want to do, and then they can get sidelined by good ideas from other members. And sometimes those are worth pursuing, but a lot of times they're, they're good ideas, but you need to still make sure that you're answering the first question you came into the event with. So we did that synthesize, uh, synthesis exercise, and that was good to kind of wrap up the day. There was a lot, a lot to digest. And then we went over to my house and had Italian food and hung the sheep is really fun. That was day 1. Okay, now day 2 was the keynote day. The keynote day is where I basically dive in and do some teaching, and the teaching is not just, hey, what's a good idea that I could teach about? The teaching is really, again, I'm going to use that word, synthesizing everything that I'm seeing in my client group. And since I coach 60 to 70 business owners at one time, I can get a tremendous amount of insight into the pattern of what's going on. So I delivered an hour and a half halftime report because we are almost halfway through the year. I distilled that down from Voxer conversations, hot seats, and audits, talked about the things that were still working and accelerating, which were of course paid events and weekly live webinars. And I had asked Amber and Emily to speak on those things because I knew they're still working. And then we also took a deep dive into human-led sales, right? That one-to-one sales. And I didn't have a special presenter for that particular, I don't know, tactic, if you will, we did in November, but I did dedicate day 3, which I'll get to in a minute, on those human-led sales. So we went through, we went through the 4 patterns of success that the data has revealed in my client group, which was a willingness to do daily sales. There were the people that are having success in my world are willing to do daily sales. They are consistent. In webinars or in some sort of sales presentation. Number 3, when they do use AI, they are prioritizing it to actually increase revenue, not just create distraction. And then the 4th thing, of course, was nervous system and mindset awareness. So I went through all of those things. I talked about, um, daily sales strategies. I talked about, um, all of the sort of ways that we sort of diagnose a webinar. To see, okay, when it's not working and how we remain consistent in our webinar performance. We talked about AI. We talked about the difference between AI as a distraction and AI as a revenue builder. And then we spent the entire afternoon talking about the nervous system and mindset awareness, and that actually rolled into a presentation called "The Three Overs." And I picked out three overs that I see: overcomplicating, overthinking, and overfunctioning. And this was an hour-long discussion And then we proceeded to hot seat people and, you know, they would bring sort of, hey, this is what I find myself doing. And we can, we could like look at, all right, what's the root cause of it? We also did some hot seats that day where we took people who had specific questions and problems and we crowdsourced the room. And then we ended the day with a 2-hour Claude workshop that Nuno led and people were customizing their Claude and getting that up and running. That was day 2. Day 2 was a free night. We didn't do anything. People, most people actually DoorDash pizza since pizza is so good in New Haven, and we ate in the lobby and worked. And then day 3 was a get it done day. I didn't teach officially on day 3. What we did was we had 4 coworking sessions, 2 that were guided and 2 that were free. And the first one was the daily sales ritual, and this was where we took Basically, we took the AI stuff we were talking about and the, the pattern of success of people who do daily sales, and we put it together and we used AI to build a daily sales ritual. And this was the moment where it was, it was crazy because I had some people that were really excited about this and then I had some people that were super hesitant and they were giving me massive side-eye and they're like, I don't know if this is going to work. And I wasn't necessarily forcing everyone to do the exact same sales ritual. I was trying to help people think like, okay, what does it mean to do daily sales in your business? How can we get AI to help you with your specific tasks? And what was so cool about this is by the end, it was 60 minutes. We had, I had people that had built a daily sales ritual far more elaborate than the one that I showed off, because mine was not super elaborate. But it just goes to show that the framework for how you do it matters greatly. And then there were some people who were pretty skeptical and they just kind of followed my path. And so at the end of 60 minutes, we said, okay, we're going into an hour and a half free coworking session. So some people went to do their one thing, right, um, that they had thought about on day one, and other people started to actually do their daily sales ritual. And this is where at the end, right before lunch, the person who was like the most hesitant, she's like, okay, I just did the daily sales ritual and a $1,200 sale just came in. And it was an aha moment for her that like, oh my gosh, she spent 60 minutes and then money came in. And then another D.I.R. said the same thing. She's like, I just did it too, and I just locked down a $5,500 retainer. And So I'm going to tell you about what came out of that in a second. But it was like things were popping off. People were building sales pages. People, you know, there was another person who's like, I just closed $3,000 in sales. And so that was really— I couldn't have architected it better if I had tried, like, because I knew I was like, I don't want to just waste people's time. I want people to actually see that this can help you earn more money. So then after lunch, we did a second collaborative workshop and we, again, we used, uh, patterns of success, which is what do people do to make money? And one of those things they do is they write emails. So we've focused on what I call the reason to reach out framework and why most people's emails get ignored. And then we used AI to help them get that out the door. And then we did another free coworking. Session. We ended the event in the Rose Vineyards in Brantford. We had a dinner together, delicious dinner, and we did an aftermind, which is where we just kind of give shoutouts to various people in the room. And it was, it was just absolutely amazing. Now, what I came away with at the end of that event was we need to do this more. This in-person small group environment where you take education and AI and implementation, put them all together. And when I got back, I decided that I was going to hold a workshop at my house, 2 days, called AI and Sheep, which I just like came up with that name. And I thought, I'm going to take everything that the AI stuff that I specifically did at the DI Mastermind, I'm going to go ahead and, and do that in a structured environment for 2 days at my house. And the sheep are you know, an amazing side quest, and I'm gonna teach. And I put up a calendar, and you had to book, like, pay your deposit, $500, and it's $1,000. Anyway, it sold out in like 3 hours. So I opened up another one in July. That one sold out in another 3 hours. So now I opened one more. So I'm doing 3 AI and sheep workshops this summer. They're 2 days. They're at my house. So June, July, August. The only one that's available right now is August. There's like 5 spots And I'm going to specifically do some of the AI implementation workshops I did at DI. And I told all my private clients, I said, if you guys want to come to any of these AI in Sheep workshops just to keep working, come. And they can just come for free. That's one thing that I think I don't share very often is that when you're my private client, you just come to stuff for free. If I launch courses, it's free. If I give out tools, they're free. If I host events, you can come for free. You know, I want my private clients to feel like they have an open door access to me. That's always how I've operated. But there are people who can't afford to work with me, and this is a great opportunity to kind of taste test what my coaching is like in that small group environment. And that was the event. And I had a 32-page report ready by the end of the event to be able to give to my clients, again because I'm using AI to synthesize. And one 3 things I want to give you here as I end this episode. Number 1, discomfort is a necessary part of business. And this happened over and over and over again. The people who can tolerate discomfort are the people who succeed, right? You know, Amber tolerated a long time of webinar— didn't— webinars didn't work. You know, there were more people, and there's some that I don't really want to share, obviously, because it's private, but lots of people expressing that when they can tolerate discomfort, they get to the other side of that, which is usually what exactly what they want. Right. And that was a big theme. The second theme was AI is not a project, it's infrastructure, right? It's a foundation. It's not about, hey, I don't have to have OpenClaw, I don't have to have 700 agents working for me, but I do have to think about it in an infrastructure way rather than a project way, and that was a big theme. And then the third thing is like, it's kind of like a meta insight, but being in the room matters. When you are in the room with people, you get something that can't happen— I mean, it can sort of happen virtually, but there is something about being in the room with people, and every time I do an event, I am reminded that that in-person connection cannot— nothing can replace it. And if you are not going to rooms or hosting rooms, I would encourage you to think about that because it really does make a difference. And I just want to say that the people that are in my mastermind are some of the most intelligent, kind, generous, uh, thoughtful, creative people I've ever met. And I I walk away from these events always sort of pinching myself, like, this is really what I get to do. Like, this is my privilege, this is my honor. And I am excited because 2027 is going to be the 10-year anniversary of Digital Insiders, which feels like a monumental accomplishment in the world of internet marketing, where people open and close programs, you know, and throw them away like tissues. But we will be at a decade next year. and that is really, really exciting, and I'm really proud of that. Anyway, I hope this was helpful. If you want to work with me, I would encourage you to reach out to me. There are about 5 seats left as of this recording for an I and Sheep, so you can come to my house and kind of get a taste test, but if you can't do that date but you want to work with me privately, I really recommend you reach out. I have a CEO Week in July that's for private clients only that has plenty of spots available. That's a 3-day event, and I would love to have you here, and I would love to be able to start working with you and, and help give you all of this strategy and insight that I'm able to give to all my clients. All right.

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 Chenell, and this has been Million Dollar Grit.