Episode Transcript
Hello and welcome to Simple Wins. I’m your host, Adam OLeary, and today we’re diving into something that I think weighs on a lot of us, no matter where we are in our careers or our lives: the ticking clock.
You know the feeling. You’re 25 and you look at a 22-year-old founder and think, ""Man, I’m already behind."" Or you’re 38, looking at your peers who seem to have it all figured out, and you feel like you’re playing catch-up. Or maybe you’re in your 40s or 50s, and you’ve just hit a plateau, and a little voice in your head whispers, ""Maybe it's too late. Maybe the ship has sailed.""
I was wrestling with a version of this myself recently. Not so much an age thing, but a ""timing"" thing. And then I watched a video by an entrepreneur named Dan Martell. And it completely reframed my thinking. Dan’s premise is simple, and honestly, a little provocative. He says, and I’m quoting him directly here: **“Most people think getting rich gets harder as you age. That couldn't be farther from the truth.”**
Now, Dan has some credibility here. He became a millionaire at 27, went bigger in his 30s, and now at 45, he says he’s still scaling businesses in ways he never imagined. His argument isn’t that youth is wasted on the young; it’s that each decade of our lives comes with a unique, powerful advantage. The key is to stop playing the wrong game for your age. You don’t try to play a 20-year-old’s game when you’re 40, and you shouldn’t try to play a 40-year-old’s game when you’re 20.
So today, I want to walk you through what I learned from Dan Martell. This is my takeaway, my synthesis after watching his video. He laid out a playbook for your 20s, 30s, and 40s, and he ended with a concept that hit me harder than anything else: a level beyond money. Let's get into it.
Let’s start with Level One: Your 20s. Dan says the main advantage you have in your 20s isn’t wisdom or connections—it’s your energy. This is the decade for building your foundation. And the entire game plan, according to what I learned, boils down to this: **“It's about trading time for money, then trading that money for skills.”**
It’s a two-step transaction. You use your time and energy to earn, but you immediately reinvest those earnings into building high-value skills. Dan calls this building your foundation, and he breaks it down into three steps that really resonated with me.
Step one is to pick one **“high-value meta-skill.”** Now, this was a key insight for me. A meta-skill is something that makes other skills easier to learn. Dan gives examples like coding, which teaches systems thinking, or sales, which teaches persuasion. Copywriting, content creation, project management—these are all meta-skills. They are force multipliers.
And here’s the part I loved. Dan says, **“I always find the best skill is the one that you would love to do. It's almost like what would you naturally do to procrastinate? If that's one of these meta skills, do that.”** What a brilliant way to think about it. Instead of fighting your natural inclinations, you weaponize them. But the critical rule here is: **“Do not diversify. Go deep.”** That intensity, that obsession, is what makes you incredibly valuable.
Step two is where Dan says most people, and probably their parents, will disagree: **“work for free.”** His reasoning is brutal but logical. When you start, you’re not good. You don’t add immediate monetary value. So, if someone experienced is willing to give you an opportunity to learn, take it, even without pay. Dan did this when he moved to San Francisco. He cold-emailed people, listed his three skills—technology, sales, marketing—and offered to work for free. He said, **“I showed up being willing to do the work without getting paid because I knew it was also going to build my portfolio. And that's what most people don't think about.”** You’re trading immediate cash for long-term credibility.
Step three is the price ladder. This is how you transition from free to highly paid. The mistake is to just say, “I’m cheaper.” The smart move is to frame it as a discount. Dan’s advice is to say something like, ‘I normally charge $100 for this, but I admire you, so I’ll do it for $50.’ That shows initiative and value. Then, **“every five clients, raise your price by 25%.”**
He used himself as an example. At 17, he discovered coding in rehab and became obsessed. By 21, he was charging $75 an hour, which equated to about $150,000 a year. He was shocked people paid that, but he had the skills and portfolio to back it up.
So, the rule of thumb for your 20s that I’m taking away from Dan is this: **“Say yes to everything that teaches you something, even if it doesn't pay well because you'll get paid on the back end of learning it well.”** And his final piece of encouragement for this stage is crucial: **“Winners lose more than losers. So, in this stage, don't be afraid to fail. Use it to fuel your growth.”**
Okay, so you’ve built a foundation of skills in your 20s. Now, Level Two: Your 30s. The advantage shifts from raw energy to strategy. You’ve tried things, you’ve failed, you’ve started to create systems. The goal here is to stop trading your own time for money and start building the machine.
Dan’s first framework for the 30s is the ATF Framework: Audit, Transfer, Fill.
- **Audit:** You have to look at your calendar and ask: Where am I spending my time? Is it producing revenue? And does it light me up? You need to identify the things that don’t make you money, that you hate, that suck your energy.
- **Transfer:** This is about taking those identified tasks and giving them to someone else. This could start small—outsourcing grocery shopping or cleaning—and scale up to hiring a virtual assistant.
- **Fill:** This is the most important part. Once you get that time back, what do you do with it? Dan says reinvest it in higher-leverage activities. For him, it’s about habits, belief systems, and character traits. He said something that really stuck with me: **“If you're easily upset all the time because there's a little problem that happens, then guess what? You'll never get big problems. And if you don't have big problems, you don't have a big life.”** You’re filling the reclaimed time with personal development that allows you to handle bigger challenges.
The second part of the 30s playbook is the Replacement Ladder. This is the specific order in which you hire to buy back your time and scale.
1. **An Executive Assistant:** This is your first hire. Someone dedicated to managing your inbox and calendar. Dan even mentions he has a document he shares with his EA, emphasizing how critical this role is.
2. **A Fulfillment Person:** Someone to handle the delivery of your service—onboarding, support, scheduling. This frees you up to sell without being afraid of the workload that comes after the sale.
3. **A Marketer:** Dan pointed out a classic entrepreneur trap: revenue goes up and down because they market when they’re not busy, then stop when they are. A dedicated marketer creates a steady flow of leads.
4. **A Salesperson:** This is the ultimate freedom hire. Dan was skeptical, thinking no one could sell his services better than him. But when he hired a guy named Michael, Michael sold *better* on day one. His reasoning was brilliant: **“Hey, Dan, I think it actually makes you look like a real business if I'm selling you instead of you selling yourself.”** Think about that. With these four hires, you can be on vacation while the machine runs itself.
The third step for your 30s is ruthless focus. Dan says **“focus stands for follow one course until successful.”** You have to pick one business model, one niche, one target customer, and say no to everything else for a minimum of three years. It’s scary, but as Dan says, **“When you say no to something else, you're saying yes to your goals.”**
So the 30s rule of thumb is: **“stop trading time for money and start building systems that make money without you. Essentially build the machine that let the people run the machine.”**
Now we get to Level Three: Your 40s. This is where Dan says you can make the most money. The advantage? Experience. The “gray hair advantage.” He joked that his designer told him he looks like J. Jonah Jameson from Spider-Man, but he said, **“The grayer my hair gets, the smarter I sound.”** It’s funny, but it’s true. You have know-how, resources, relationships, and pattern recognition. Now, it’s about scaling the machine you built in your 30s.
Dan recommends three ways to do this.
First, a smart **Portfolio Approach** to investing:
- **70% in what you know.** Don’t diversify into random things. If you’re a real estate expert, invest in real estate. That information advantage is what makes you rich.
- **20% in adjacent opportunities.** For Dan, that’s tech startups in areas like 3D printing or drones—things related to his wheelhouse but with more risk.
- **10% in moonshots.** The crazy ideas, like a friend’s restaurant franchise or a “millennial laundry detergent” company. Fun, high-risk, but not your core focus.
Second, become a **Mentor Investor.** This is powerful. You find entrepreneurs in their 20s or 30s who are 2-3 years into a business in your field. You provide them with what they need most—not just capital, but your experience. You become an advisor in exchange for equity. As Dan put it, **“Now you've got shots on goal that could turn into bigger outcomes than your current thing you're working on.”** You’re leveraging your wisdom.
Third, **Compound Your Wisdom.** This means actively reflecting on and documenting what you’ve learned. Dan said he’s been doing this for a decade. By codifying his frameworks, he not only understands them better himself, but he also creates tools to help others. This is what makes you incredibly valuable in your 40s: **“the experience to come into a situation and see in 30 minutes identify the three things that that founder... can do to change to 10x their growth because you've seen it so many times before.”**
The rule of thumb for your 40s is: **“let your money work harder than you ever did. Your job is strategy, not execution.”**
But Dan didn’t stop there. He introduced a final level that, I’ll be honest, moved me. He called it **“your legacy years.”**
He said, **“Here's what nobody tells you about getting rich. There's actually a level beyond the money.”** This is where you stop using your success for accumulation and start using it for impact. It’s a fundamental shift in purpose. **“It's understanding that when you decide to teach everything you've ever learned to the next generation, then you'll feel fulfilled.”**
Dan shared that he runs a program called Kings Club, mentoring 100 kids a month, visits crisis centers, and speaks in prisons. He does this because people did it for him. The rule for this stage is: **“this isn't about you getting richer, it's about making others rich in more ways than one.”**
This brought him to his final, profound point. **“This game of life was never about the money. It's about becoming the person along the journey.”** Wealth, true wealth, is the ability to improve your life, to get to a place where people want to learn from you, and for you to share that with them.
So, after learning all this from Dan Martell, I’m left with his closing questions, which I now pose to you, and to myself:
Is my skill really next level? Am I really world-class at what I do? Have I found ways to leverage that within my existing business or with a team? Have I found people I could partner with to create more without having to work harder?
And most importantly, the question that truly defines the endgame: **“Have I even considered that maybe sharing myself with the world is actually what it's all about?”**
It’s a powerful thought. It’s not about your age. It’s about playing the right level. Where are you playing today?
Thank you for listening. I’m Adam OLeary, and I’ll see you next time.
