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So if you are tuning into this one, you have not heard part one of this episode, then be sure to go back to the most recent solo show that we dropped and you'll find part one there. But for now, go ahead, enjoy part two of this episode. This is absolutely something that I've experienced on a firsthand anecdotal experience or basis. Even even it was just sort of a realization because I this last time we we filmed this this show called Dinner Party and we our first episode we had Shaquille o', Neal, Alex Shamozi, Shran Srivatsa, Graham Stephan from Iced Coffee Hour, and Zach justice, comedy podcaster, YouTuber. And I posted about it on social media and Joe Gatto from the Impractical Jokers hit me up about it and was like, hey man, that looks like you're doing some cool things. Let me know if you need any help. And it happened to be that I needed some help. I was just like, hey, I'm curious what this would look like if we maybe tried to turn this into more of like a show versus like just a podcast, which is what my expertise is. And obviously Joe was on a very successful television show for a decade and that show remains it continues to be successful even after he's left a few years ago. And so and what I when I realized that this was happening was a couple days after I finished this dinner, which was Shaquille o' Neal is like, I mean the, the legend to me, he was childhood hero of mine. And so it was. And that was the second time that I've had on my show, first time was virtual over, you know, zoom a couple years ago. And then this time was in person for over an hour with a bunch of these other cool people in the room. And when I was done with that, that conversation a couple days later, Joe Gatto, like, we just hop on a FaceTime call for like 20, 30 minutes and just like, talk about all this stuff. And after I hung up, I realized that when I first started my podcast, I had sort of a dream list of guests. Like, I had. I had several lists of guests. And I segmented my lists of guests into different sections, which I think is valuable. One of them being like, yes. Like, this is my yes list. Like, these are the people that I absolutely know will say yes, because I actually know them as people, and we have a prior relationship and they'll just be happy to jump on and support. And then there's like, the people that are one connection away from those people. And then there's like, the people that are going to be a difficult reach out, and I don't have any prior connection to them, but I have strong confidence that, like, with given enough reach outs, a good amount of them will say yes. And then I had this list of people that was like, these are just. I have no earthly clue how these conversations are ever going to come about, but I'm going to put them down on my list anyway. And a couple of the people on that list were Shaq and Joe Gatto. And it was really cool to just realize that, like, oh, I just did this, like, you know, two and a half hour podcast where Shaq was a guest for over an hour personally. And then I hopped on a FaceTime call with Joe because I have a good enough friendship with him where he's willing to do that without even me asking. He just offered because he's a good dude and because he cares about the things that I'm working on. And it was a cool moment for me to sit back and go, like, I've experienced a lot of ups, and I've experienced even more downs than I've experienced ups in this entrepreneurship journey. But it was cool to sit there and go, like, man, people who I never like. I had no idea how it was ever going to come to fruition to be able to have a conversation with them. Here I am sitting seven, eight years later and just had a conversation with this guy, and then this guy's hopping on to have a conversation with me about the conversation that I had with this other guy. And it was just like a really cool full circle moment. And exactly what I just said before is what I experienced in that moment where just your sense of what is possible continues to expand. Because I just didn't think that those things were possible. I thought it was possible enough to write it down on a piece of paper and go, we'll see how this goes. But even in the back of my mind I was like, I don't know how this is ever going to be something doable and but it, it is given enough time and given enough rejections that you go through so exposure, like rejection therapy essentially, and then the information that you gain, as well as that information being more practical and more easily applied into your life and then proximity. So the point is not that every successful person becomes your mentor. The point is that every real conversation Chime is changing the way that people bank. They offer the most rewarding fee free banking that's built just for you, not the 1% Chime members can benefit from up $1,150 in annual rewards fee free. It's rated five stars by USA Today for customer service because you get real humans 24. 7. You're not just switching banks, you're upgrading to America's number one choice for banking with a Chime checking account. Plus, you can get up to 5% cash back on a Chime card in your category of choice like gas or groceries. You get savings that grow even faster with 3.75% APY, which is nine times higher than the national average. Plus you get premium travel perks like airport lounge access and 24. 7 travel concierge included with your Chime card. You can even get up to $500 of your pay when you save with my pay. They also have Spotme which lets you overdraft up to $200 fee free. I know my younger self would have benefited from this. Chime is not just smarter banking, it is the most rewarding way to bank. So join the millions who are already banking fee free today. Head to chime.com travis that's chime.com, only takes a few minutes to sign up. Right now Chime is a fintech, not a bank. Banking services for MyPay and Chime card provided by Chime's bank partners. Optional products and services may have fees or charges, stated annual percentage yield and cash back for Chime prime only. No minimum balance required. Checking account ranking based on a J.D. power survey published October 20, 2025. For more information on APY rates, MyPay, Spot Me and travel perks go to Chime.com disclosures ready to soundtrack your summer with Red Bull Summer All Day Play? You choose a playlist that fits your summer vibe the best. Are you a festival fanatic, a deep end dj, a road dog, or a trail mixer? Just add a song to your chosen playlist and put your summer on track. Red Bull Summer All Day Play. Red Bull gives you wings. Visit red bull.com brightsummerahead to learn more. See you. This summer removes a little bit of the, the intimidation tax that you've been paying for, you know, basically your whole life leading up to this point. So now let's get into the challenge itself. The, the rules of the challenge. Okay, here's, here's, here's my challenge to those of you who are listening. For the next 30 days, all I want you to do the core metric that is within your control. Like because there's, there's inputs and there's outputs, right? And sometimes we can't always control the outputs, but we can control the inputs. Let's focus on the inputs for this challenge. For the next 30 days, send five cold DMs per day. That's it. I like DMs better than I like email. If you want to do email, I suppose that's fine. I think DMs have just this level of personalization that you can use and they're just simple and more easy and a lot of people use them. And that's probably been my number one way of booking really high level guests is just sending them a dm. Plus you can use video a little bit more effectively and easily. It's more of like a native feature of those platforms versus like finding an email plugin where you can use video. And then people aren't really trained to watch videos on their, in their email. So it just doesn't, I don't, don't think it works as well. So my encouragement would be DMS aim for one booked interview per day. And again, this does not need to be like an hour long in person podcast interview. Okay, this could be a three minute FaceTime interview. This could be a two minute Zoom interview. This could be go live with me on Instagram for 5 minutes type of a thing. Like whatever version of the interview is, it doesn't, that is sort of inconsequential. It's just getting the reps in of reaching out to people who you never thought would give you the time of day and then seeing results actually come in from that. And like I said, you don't have much control over Whether or not somebody says yes. But if you make your lists like I suggest you make the list like segment them into like these are like dream impossible guests. But then you also have a list of people that's like, don't know. Like if they know me and I maybe they know a person that I do know really well or they follow somebody that follows me. Like there's that sort of adjacent one. That's where I would really like you to spend a lot of the time on this one. Because if you just do it to the people that you know, that's a little bit different. You might do that for the first like two or three days just to get some wins and get some confidence going early on. But then move into that segment where it's like, it's a little bit of a stretch because you don't really know them and they don't really know you, but you kind of maybe had an interaction one time or something. I think those are a really good list to start with. So aim for one booked interview per day out of the five DMS that you, that you send the interview. Length again does not super matter to me in this scenario. Take whatever they will give you, you know, ask them for. Nowadays it's cool because we're sort of in this like social media podcast world where a lot of podcasts are concern consumed on social and on social only they're not actually being listened to long form. So you, there's an opportunity here for you even to do just like a short form podcast show on your Instagram or tick tock or YouTube shorts or something like that. So the, the length of the interview is sort of inconsequential and I've not found that it really matters when you're reaching out. The busier the person is, I guess the more that that it's going to matter. But you know, 10 to 20 minutes is really is really all you need and you're not going to find a bunch of people who are really opposed to that length versus a 30 minute length or something like that. And then just have a script of questions. Just come up with the questions that you really want to know and they could be the same exact questions. You might change them up a little bit depending on the guest. If you want to make it really simple and focus all of your effort right now on just the dming and the part that scares you, then just have your the core scripted questions that you want to ask them stuff about whatever there are they are successful in or the niche that they're successful in. Let's say you, let's say you, you are wanting to start a really good YouTube channel or something or you've been struggling to grow YouTube channel. Okay, well then this, this challenge is going to be for you to reach out to 30 YouTubers and ask them the same five questions. What did you do to grow your channel? And, and what, what is the biggest mistake that you made while trying to grow your channel? When did you see the most growth? What video is most responsible? You know what I mean? Like just, you know, 5ish questions that you just ask every single person and then get on the call, record the call and go through the questions. Okay. And then after the conversation, send them a quick thank you for taking the time to be willing to have a conversation with you and then track all of your progress. Track. You know, here's the people I reached out to on day one. Here's what happened with that. Did they respond? Did they ignore? Did they say no? Did they say yes? Did they book an interview with you? Just, just keep track of those things so you have something to look back on. Because some of these times, like a couple of these days, you might just want to spend some time doing some follow up and going back to people who never responded or they saw your message but ignored it. And maybe you can try for a different angle and send a quick follow up and, and be able to capture some of the people who were originally saying no. But yeah, five messages a day for 30 days is about 150 outreach attempts. So if you book 20% of those, that's 30 interviews. And if it's much lower than that and you get 15 interviews, okay, you get 15 interviews. But like my challenge to you is just to do the dming. Like, do like the result, again is less consequential than the activity of just putting in the reps and being okay with what happens, that you might get some rejections, you might get some people ignoring you. In fact, you will absolutely get both of those things. And if you get a hundred percent, then you let me know what you're doing because I have not figured that one out yet. But yeah, it does not, it does not need to be, it does not need to be the Shaquille o' Neals of the world. Okay? Just, it could be the person who owns all the gas stations in your town. It could be the person who, who has a 50,000 subscriber YouTube channel and you're at 200 and wondering how they got to 50. It doesn't have to Be the. It doesn't have to be Mr. Beast if you're a YouTuber. It doesn't have to be Shaq if you're an athlete. It doesn't have to be Nate Bargazzi if you're a comedian. Does not have to be any of those, you know, legends in the space that you are in. It's just something, someone that's meaningful to you, someone that's done something that you're like, that's cool. I respect that. Can I talk to you about it? Just doing the work to target those entrepreneurs, creators, investors, salespeople, coaches, authors, whatever, community leaders, pastors, local business owners, people who are in your dream role in your company, people who are excellent at the skill that you're trying to become, excellent at whatever it is, anybody you can look up to and respect in some light. Fill your list of these people and start DMing those people. They do not, they absolutely do not have to be famous. In fact, a lot of the times you'll probably get more from somebody who's one step or two steps ahead of you than you will from somebody who's 15 steps ahead of you. Because the, the gap there is so large that it's sometimes even more difficult for those people to share actionable advice with you because it's been so. It's been 35 years since they lived in poverty. So like, they don't even like, have a great recollection of what it was like to live life without a multitude of opportunities at their fingertips or without turning down 300 speaking gigs a year or whatever it is. So don't feel that it has to be the massive names, just, you know, people who have done something that you respect, reach out to those people. Now what do you say in the dm? Okay, very simple. Keep it as the, the. Instead of telling you, like, here's the exact script to say. Cause I think that's sort of dangerous. You can start, start sounding really templated and, and you don't want it to, you don't want it to appear to them that you just had AI write this for you. And for the love of God, please do not have AI write this for you, okay? If you don't know how to write a 50 word DM outreach script like that is absolutely something you should work on in this process. Do not ask AI to do this. It's going to sound terrible and stupid, so don't do that. So in the dm, what you want to do is first off, lead with values. Lead with something that makes them Realize that you actually care about the thing that they're working on and make it, make it completely personalized to them. Do not make something up. Okay? I get those all the time in my email inbox and it drives me insane because I know they're just flat out lying for whatever reason. Every once in a while people are just following the same script and it's probably written by AI. Eye roll, Eye roll. But it, it, I've. This one I've begun recently is like, when people are trying to get on my podcast, they'll be like, hey, Travis, I'm reaching out because yours is one of the only podcasts that I actively listen to on the regular. And I found it a couple of years ago and since then I have not been able to stop listening or whatever. And every time I simply respond with like, oh, great, how'd you hear about the show and what were a couple of your takeaways? Or like, what, what episode specifically are you referring to? Or something like that. And they never get back to me because they know I'm calling out their, like, don't, don't lie about it. That's such a turn off to anybody. And it does the exact opposite of what Leading with value is meant to do, which is just share that what you're doing is meaningful to me. And that's why I wanted to reach out. So I usually start with something like, hey, saw you just announced your new book. I loved your last book and this thing I took away from that last book. Great work. Or like, I'm just going to start with something and again, keep it short and sweet. The overarching rules here when you're sending cold DMS to successful people or people who have a lot of demands in their time is don't be another demand on their time time. So don't throw a book out there. I, I made this mistake so much when I was first getting started. I was like, I have to write basically like a sales letter. So I just would write out, it's like six paragraphs of just like a bunch of black text with a white background. And it's just, it's, it's a nightmare for somebody who's trying to like get through their email inbox to see an email like that. They're probably just going to archive it, they're going to delete it, they're going to delegate it, they're probably not going to read the whole thing. So just give them the information that they actually need to make a decision. Okay? And especially if you're in the DMs because then that can start getting really annoying when somebody sends you a book in your DMs so something personal to start it off with and then a little bit of, and then, and then go directly into the reason that you're reaching out with a little bit of information about you. So like the reason I'm reaching out is I'm doing a 30 day challenge where I'm just interviewing people who are more successful than I am. You know, my name's Travis. I. Or let's start with that. Like my name is Travis. I'm reaching out to people for, to, to do some interviews. Like very simple. But you just want to make the ask very crystal clear. Again, people who are busy don't want to take the time to try to decipher an ask through the vomit of information that you've thrown in their inbox. So be very clear, very specific about the ask and then, and then go in for the ask afterwards. Would you be open or is there any reason why you would not be able to take 15 minutes for a quick zoom interview next week or the week after or whatever? Be a little, be flexible on the timing and the scheduling, but give them options. Don't, don't just leave it open ended to be like let's do it sometime. Cause then they might be like sure. And then it's like okay, well when you know, like don't, don't do that. Like you'll try to throw out a couple options there and both options being options that work for you. Like I can, I'm setting aside time next week and the week after to do some interviews. Would you be able to do something in that time frame? Yeah, I can. Okay, great. Is Tuesday work for you or something? And if you need to create a quick calendar link or something like that that just allows people to use your link and go book into your calendar for 15 minutes. Something like that's really easy. The point is though, like keep it, keep it really low friction. Don't insert like four different steps in order to be able to get them to say yes. The, the more friction that you put in, the less likely you are to get a yes there. So clear. Ask specific. So, so, so specific. Personal compliment or something valuable. Hey guys, Travis here. Just letting you know that sometimes on the show I go a little bit longer. I try to keep these things, these solo shows pretty short, like 10 to minutes. But sometimes when I get going I just can't stop, if you know what I mean. So this, if you're listening to this message. That means that this episode is being put into two parts, and the first part is now coming to a close. So be sure to tune into the next solo show to hear part two of this episode. Thanks for tuning in. Catch you next time. Liberty Mutual customizes your car and home insurance. And now we're customizing this ad for your morning commute to wake you up, which could help your driving. Science says that stimulating the brain increases alertness. So here's a pop quiz. How many months have 28 days. What gets wetter as it dries? What has keys but can't open? Locks? If you don't want to hear the answers, turn off this Liberty Mutual AD. Now. 12 months. A towel piano. Enjoy being fully alert.
Episode: SOLO | Make Money By Having the Conversations You've Been Avoiding, part 2
Host: Travis Chappell
Date: May 18, 2026
Travis Chappell continues his candid solo series on overcoming avoidance and building financial and personal success—not by cutting corners or living smaller, but by expanding your network and worldview with bold outreach. In this second part, Travis shares personal stories of breakthrough moments, breaks down the actionable 30-day “challenge,” and offers practical advice on how to reach—and actually connect with—people who inspire or intimidate you, all in service of making more money and living a life you actually want.
Travis shares an anecdote about achieving what once felt impossible: meaningful conversations with childhood heroes like Shaquille O’Neal and comedic icon Joe Gatto.
1. Personalization Over Templating (29:00)
2. Make the Ask Crystal Clear
3. Lower Friction
4. Thank and Track
Travis’s message:
“You cannot save your way to your dream life. Expand your world by having the conversations you’ve been avoiding. Those who do the reps, win.” (paraphrased from multiple sections)
Useful for listeners:
This episode is both motivational and tactical, offering concrete steps for anyone wanting to level up their network, skills, and ultimately, income—by simply having conversations they’ve been scared to start.