Once You Make Money, Upgrade These 7 Things ASAP

In this YouTube monologue, the presenter argues that after achieving a certain income level, the most effective way to improve quality of life is to make targeted "upgrades" rather than simply buying back time. He outlines seven specific upgrades that the top 1% use: (1) Cultivate regular hobbies to boost mental health and energy, citing a large longitudinal study and the concept of "memory dividends" from Bill Perkins' Die with Zero; (2) Automate low‑value decisions (e.g., meal‑prep, clothing, assistants) to eliminate decision fatigue, referencing research on parole judges and examples from high‑profile figures; (3) Purchase a high‑impact luxury item (e.g., an expensive watch or car) that serves as a daily forcing function toward ambitious goals; (4) Invest in a new identity by traveling or undertaking solo retreats, allowing a reset of self‑perception and the adoption of new habits; (5) Buy friendships by deliberately spending time and money on relationship‑building activities, using the 5x5 rule and lessons from Never Eat Alone; (6) Put money to work through low‑fee index funds, skill acquisition, and strategic investments, emphasizing that idle cash loses value to inflation; and (7) Buy love by giving time, mentorship, and charitable donations, illustrating how generosity creates reciprocal emotional returns. Throughout, he intersperses personal anecdotes, actionable frameworks (3Fs, 5x5 rule), and calls to action (e.g., request an Executive Assistant playbook). The overall message is that strategic spending on experiences, systems, symbols, identity, relationships, capital, and generosity accelerates personal fulfillment and long‑term success.
Chapters
Most finance content tells you what not to buy. Today, I'm gonna do the exact opposite because there are 7 things that you should upgrade once you start making money. Now, normally my advice would be to spend money to buy back your time, not stuff. I even wrote a whole book about it, but these 7 upgrades take things to the next level. This is what the top 1% spend their money on. These things don't just save you time, they change how good life feels day to day. So let's get into it. The first thing on this list is something almost every finance guy would tell you not to buy, something completely useless. When I was 22, I was working 100 hours a week. I was this frenetic energy ball, and I thought that was my edge. My body honestly said stop. I ended up getting sick. I got diagnosed with adrenaline fatigue. I even got shingles on my back that almost turned into a whole fucking moment. Luckily, my doctor caught it in time. I could not turn it off, and I thought that approach was the right way, but it was costing me my business and my life. in my relationships. And then I found some hobbies. Snowboarding, mountain biking, I fell in love with. Now wakesurfing. It allowed me to disconnect from the work, and it turned out that it made me a better person. And surprise, surprise, it gave me more energy to actually do more output. Somebody smart said this a long time ago, but you can't pour from an empty cup. And look, science backs this. A study published in Social Science and Medicine tracked 19,000 adults over 50 Over 8 years. What they noticed is that if they had a weekly hobby, their depression, if they had any, would dramatically drop over the next 2 years. All the top guys literally have hobbies. The mistake is most people think that hobbies drag us down or take from our time, and the opposite is true. And in the age of AI, this matters more than ever. One of my favorite books is called Die with Zero. Bill Perkins wrote a masterclass in how to think about this. He looks at money as a store of energy. Which means nothing until you convert that energy into an actual experience. He calls this memory dividends. Money is useless unless it's used to purchase memories. And look, you don't want to wait for this. This is the homework. Go back to when you were 12 or 13, before Practical existed. What would that kid beg for today? Maybe you used to love going to the ski hill. Maybe you gotta go buy a ski pass. Just buy the small version and go do it this week. I like to use this model called the 3 Fs. Something fun that you can do frequently with friends. For example, fun, I love to wakesurf. Frequently, I do it every day, sometimes twice a day. And friends, I'm bringing my team members, new friends that I don't know that well on the boat. This right here will change everything. It will make your life more fun, which means you'll have more to give. The second upgrade might sound even worse. I want you to buy something that makes you lazy on purpose. Decision fatigue is real and it drains everybody the exact same way. There was actually a study on parole judges. Imagine you're in front of this judge and you're like wanting to get out early in the day, 65, 70% chance he's gonna approve that you get out. Closer to lunch, the approval rate drops to nearly 0%. Then he takes lunch and he comes back, it shoots back up. That's crazy. Same cases, same judge, wildly different outcomes, purely based on his decision fatigue throughout the day. Making a decision is like burning little battery packs in my brain, and the least amount of decisions I have means I have more battery juice to make big decisions. So I'm trying not to waste my battery packs in my brain on little things so that I have more juice for the big things. And look, the top 1% people, they've known this. That's why you've seen Jobs wear the same black turtleneck for decades. Tim Hortons, blue shirt. It's not 'cause I'm like trying to do a video thing. It's because I don't wanna think about it. Obama said it himself. He only bought 2 suit colors and it saved him bandwidth when it came to real decisions. Zuckerberg, same thing, same gray t-shirt. Actually, lately he's kind of upped his swag game. I've noticed, bro. Nice work. And look, it's not lazy. It's on purpose. I've been doing this for years. I learned it when it came to my health, specifically around food. My trainer looks at my numbers and he makes decisions on what I should eat. That gets put in a spreadsheet, sent over to the local meal prep company. They look at the spreadsheet, they make the meals, the meals get delivered to my office twice a week. I never have to think about it. Every day at lunch, I open the fridge, my meal's there. Instead of focusing on what I have to eat, I can use that to be more creative, to come on here and shoot better videos, to be better for my team. And guess what? I stay the same weight all the time. I never have to stress about it, and I'm never hangry. The most disciplined-looking people aren't the most disciplined. They've just automated boring choices so discipline never has to show up. Set it and forget it. This is implementing a system to not create decision fatigue. So I'm encouraging you to be lazy. So here's what I need you to do. Pick one daily decision that you will pay to automate and eliminate it. And it doesn't have to be expensive. My recommendation, meal prep services. It could be cleaning for yours. It could be grocery ordering. It could be wearing the same blue shirt every day. And if you're a business owner, the best way to do this is just to get an assistant. Which side note, if you've been thinking of getting an assistant or you have one and you wanna learn how I've worked with mine over a decade, I have a 42-page document that covers everything from the inbox structure to the templates, to the calendar management, all of it. If you want it, just find me on Instagram and message me the word YouTube EA and I'll send it your way. Now that we bought something that's gonna make you lazy, we want to buy something that's gonna make you not lazy too. When I'm out in the world, the watch people always ask about this watch. My favorite thing is when kids ask about it. They go, hey, is that a Richard Mille? And I'm like, yeah, bro. And they go, how much is it worth? And I'm like, do you really want to know? They go, yeah. I said, it's worth half a million dollars. And they freak out a little bit. And I usually, unless I'm worried they're going to run away, I take it off and I give it to them. I said, hey, try it on. See it. See how it fits. Now, I don't wear this To tell everybody I have a half-million-dollar watch. I wear it to remind myself what I'm trying to do with my time. See, I have a goal to reach $1 billion in enterprise value, not for ego, not for money, but to be an example of what's possible. Considering where I came from, which was zero, actually worse, in a hole, and watching my life become this incredibly blessed opportunity that I get to live, I wanna have a symbol with me that forces me to ask the question, Am I doing the thing that creates the probability of that outcome? And for you, it might be your car. It could be your house. It could be your cottage. It is what it is. Sometimes we need to make investments, buy something that actually stretches us. When Jay on my team said, hey man, should I buy that Porsche? I knew his financials. He could afford the Porsche barely, but buying that Porsche forced him to work for it every single day. And if you ask him today, his revenue has gone up. That car created the forcing function for him to focus, to not be lazy. The constant reminder to create. It's easy to get caught up in life and lose sight of what we wanted to create in the first place. And that's exactly why you need something to force you to see this every single day. That's what this watch actually is, not a flex. It's a reminder I can't look away from. The next thing to buy was huge for me, and I can't recommend it enough. You need to buy yourself a new identity. When I was 22, I saved all my money and I got on a plane and I went to Australia. And what's funny is that even though I learned about different cultures, I traveled and I backpacked with other people from all over the world, the thing that I learned that I didn't expect was that I had the opportunity to reset. In our day-to-day lives, people have perceptions of who we are and that creates our identity. And then I go to Australia and I have none of that. And then I get to choose, who do I want to be? Maybe I was a little quieter before. Why don't I be loud? Why don't I try it on? It's like a jacket. Try it on, see if it fits. If it does, I keep it on. If it doesn't, take it off. That was the first time I ever got on a road bike and I started biking 50 kilometers every day. I'd never biked in my life to that point, but nobody was like, oh, Dan, you're not a biker. Why are you biking? They were like, wow, it's really cool that you're biking. You're inspiring me. I'm like, Oh, that's interesting. I did all these things that I wasn't before because my identity kind of made me feel like I'd be judged for it. With this new location, this new place, I could choose who I wanted to be. Spending money to create this for you, the better version of you. Awesome. A couple years ago, I decided to spend five days by myself in a van. My friends called it the Dan Van Pasana. It's like a meditation retreat, but I just went by myself. No device, no internet, no phone. No plan. And I just had fun. I walked around, I talked to myself a lot. Have you ever been in the woods and you're just like talking to yourself? You're like, hey Dan, this is interesting. Why are we here? Why are you saying we when it's you? Why am I here? Hmm. I didn't have to be Dan in any of these moments. I could have literally gave myself a new name. Sometimes you need to discover who you are again. It teaches you humility. It teaches you communication. It teaches you social skills. You get the time to think, to reflect, how do I wanna show up in this world? Now, you don't need to do a multi-month road trip to Europe or to Australia or wherever. You can do this yourself by jumping in your car and just going to a different city by yourself. What I'm gonna ask you to do is open up your calendar sometime into the future, 6 to 12 months, and put that trip in there. But remind yourself, when you're there, you get to invest in your new identity. You get to try on some different behaviors and see how that fits. And if you like it, that becomes a new version of you. You get to invest in a new identity if you give yourself permission. Next, we need to invest in something most people say money can't buy. You need to buy yourself some friends. Now I know you're gonna be like, this sounds stupid. Do you tell your kids go buy some friends? No. I read this incredible book a long time ago called Never Eat Alone by Keith Ferrazzi, and it changed my whole philosophy on relationships. His point, very simply put, was that you are the byproduct of the people you spend time with. Your net work is your net worth. His philosophies at the time freaked me out. He would say in the book, I recommend for your business relationships to invite them to do things like a workout. And I'm like, who the fuck would want to come work out with an introverted programmer and sweat it out inside of some spin class? He's literally like, go do Jazzercise. I'm like, I've never been. I don't even want to go. Why would somebody I don't know want to come with me? It was such a foreign concept. That it was laughable. Eventually I learned, oh, through the right conversation, you can get somebody to come for a workout. It could be a walk, it could be a run. I would organize dinners and pay for them with people I wanted to build relationships with. I would spend time and money, get on a plane and pay for hotels and go to seminars to potentially meet somebody that might be part of my life forever. My rule was if I went to an event, my only job is to find 1 or 2 people that I could be friends with for the rest of my life. And when I look at my peer group and the people that are closest to me, the folks that I do like couple date nights with or family vacations with, these are all people I met at events by investing in relationships. Even my wife, I met her at an event. Getting to spend time at Richard Branson's house, I met through a friend where I hosted one of these dinners. Having Mark Cuban invest in my company was a byproduct of inviting another guy to a dinner. Today, I've been hosting a Founder's Hike that's gone global. People all over the world are doing their own versions of this. Every Tuesday in Kelowna, BC, and you're all invited. Thousands of people have come, but it all came from the concept of buying friends, investing in relationships. Here's my process. It's called the 5x5 rule. You reach out to 5 people every day and you provide 5 times more value than you're asking for. And then host dinners, hikes, gatherings. You can pay for it. Maybe you all go Dutch, but it's really cool if you can pay to create a space A lot of people are like, well, what's the occasion? Just say, I'm trying to get people like you together so that you guys can all meet. It's just a connect. It's just a support. There's no agenda. I've got nothing to sell. I do this every week times 5. That's how I've been able to build the relationships in my life. So make sure you buy yourself some friends. Next, we got upgrade number 6. We need to buy ourselves some money. When I exited my first company, Spheric, I had a ton of money in my bank account. Now, a great mentor of mine said, hey, take half, put in your next big company, and the other half, you need to invest it. You need to learn how to make the money make you money. That's where not only did I invest in low-fee index funds, but I also invested in other companies. Those angel investments became worth tens of millions. One of my companies, Intercom/Fin, just sold for $3.6 billion to Salesforce. Most people would just sit on that money. They'd be like so worried. They'd just keep it in their bank account or put it in some GIC because it's comfortable and it's not scary. But the truth is money just sitting there, loses value every single day because of this stupid thing called inflation. Your money today is worth less than yesterday, and it'll always be the case, and it's getting worse. So you better learn how to do this. The money I put into my investment has generated a lifestyle where I don't have to work if I don't want to. You don't have to learn how to trade stocks. You don't have to learn how to buy and do puts and options. You can start with, like I said, a low-fee index fund. You just have to be in the market. Maybe it's in your primary residence in real estate, Maybe you want to buy some stocks in companies where you are already a customer. And if you're starting off, the number one investment is skills. How do you increase your earning potential? What are the skills that I could invest in to learn that's going to make me more money? That return could be 50 to 100% per year compounded. The key is don't let your money sit in a pile. Put it to work. Consider it like little soldiers out Out in the world doing work on your behalf, and a bull interest rate from your bank is not what I'm talking about. So you got to buy yourself some money. This next upgrade might even sound a bit illegal, but you can actually buy yourself love. People might say, "Wait, you can't buy love, Dan." You can. Here's how I learned. When I was eleven, I got put on ADHD medication because somebody told me. There was something wrong with me, that my energy was too much for the classroom. And that decision to put me on medication led to me sliding into a depression, making a series of bad decisions, hanging out with people twice my age, got introduced to drugs, and almost taking my life. And at age 17, I had somebody incredible named Brian sit me down and invest in me with their time and words. I never forgot what that felt like. That became my everything. It became the foundation for my Kings Club program, where I mentor young youth. It became the foundation of the Martell Legacy Foundation. The kids that I meet at detention centers as I travel the world—I was just back at the place that saved my life, this rehab center called Portage—talking to these same kids, these 15, 16, 17-year-olds. And it's crazy because this kid came up to me and said the only reason. He was in rehab, was because his mom had been showing him videos that I publish, sharing my story with them. That appreciation, that love that I felt—to me, that's everything. See, most people say, "Well, I would give to charity, but it doesn't feel like I get anything in return." And I would argue, when you give, you get back love. Every year, my wife and I have a giving day where we have the opportunity to. Gift other organizations that work with troubled youth. And I will tell you, when I show up with a check to help an organization serve these kids and they're in tears, the love I feel, it makes every dollar I invest worth it. And it's my why. Look, Nietzsche said it best. He said, he who has a why to live can bear any how. And I'm not saying that I do these donations because I need this love. I'm just reminded when we help other people, who's really getting the help? Who's feeling the love? It takes both people. That's why I don't just give my money. We show up with our time, our influence. So if you want to do this yourself, ask yourself, who did you need in your darkest days? What pain did you go through that you would like to help other people avoid? If you could be the resourceful person that you needed most, if you could be the purpose for somebody else, And show up with a small donation in a tough time, you'll feel that love. And don't wait till you feel like you can afford it. If you can't give when you got a little, you're not going to give when you have a lot. You have to build that giving muscle. So look, freedom is not found in your bank account and it's not found in your calendar. It's found in the things you invest in to bring more life into your life. Most people that have a hard time winning is because they made life hard. If you invest into these things, it will make your life full. That is what success is really about. And remember, if you want my Executive Assistant Playbook, just find me on Instagram and DM me the word YouTube EA and I'll send it over. Now, none of this matters if you're still trying to make money in the first place. So if that's you, watch this next video. It's exactly what I do to hit my first $100K a month.










