The Paul Truesdell Podcast Website Rough Draft
Today we are going to talk about leadership, resilience, and what it really means to stay standing when the waves get high. This is not theory. This is earned perspective from decades in business, investing, mistakes, wins, and reinvention. This is for high school students trying to figure out direction, college students questioning the system, young adults grinding through the early years, professionals building or rebuilding careers, business owners carrying risk, and retirees in the go go years, the slow go years, and the no go years. No matter who you are, no matter where you are in life, no matter what you do or what you have, plug yourself in and get ready for my view of the waves of life, how they form, how they break, and how you learn to ride them instead of letting them roll right over you.
Well, my fellow entrepreneurs and dreamers, pull up a chair and let me tell you a story about leadership that might just remind you of the spirit that built this great nation of ours. Now, I am not here to lecture you. I am here to share something with you, friend to friend, the way folks used to do when they had something worth saying.
Now, I want you to remember this phrase, and I mean really let it settle into your bones: “You have to keep your knees flexible on the surfboard of life.” Let that sink in for a moment. You see, it is not just about balance, though balance matters. It is about adaptability. It is about resilience. It is about maintaining your core strength, your center, while navigating the unpredictable waves of business and personal challenges that are going to come your way whether you are ready for them or not. And let me tell you something, friends—those waves are coming. They always do. The only question is whether you will be standing when they arrive.
Speaking of waves, let me share something deeply personal with you. Back in 1968, I was just a kid riding a Schwinn Stingray bicycle loaded down with newspapers, working day in and day out as the neighborhood paperboy. Rain or shine, I was out there learning lessons I did not even know I was learning at the time. Then came October 1, 1986—a date I will never forget. That was the day I declared myself financially independent. Now, let me tell you what that means, because it is not what most people think. Financial independence is that moment in life when you work because you want to work, not because you have to work. And here is the beautiful part, friends—I love to work. I always have. Because when you do what you like, what you are good at, what you are profitable at, and what you can control, it is not work. It is fantastic. It is a gift. From that paperboy on the Stingray to the man I am today, I discovered something fundamental about financial independence that has guided my entire career. In the 60s, and early 70s as a kid, I learned a whole bunch of business lessons. As a kid then as a young man, and still today, I’m and still making plenty of mistakes. But I stumbled through hands on experience that single and critical principle that changed everything for me and is the fuel for me today. It is simple, but do not let that fool you—simple is not the same as easy. Again, I do what I like, what I am good at, what I am profitable at, and what I can control. Let me emphasize that last part, because it is the part most people miss. “What I can control.” You see, that is not just a philosophy. That is a strategic approach to life and business that separates successful entrepreneurs from the folks who spend their whole lives chasing the wind.
Let me tell you something profound, and I hope you will take this to heart: I will never retire. Never. Now, that is not bravado talking. That is not some old man trying to prove something. That is a commitment, a sacred one, to maintaining that spark, that zest for what you do, coupled with decades of hard-earned experience. You see, as a true investment and wealth manager, I have come to understand that your greatest asset is not just your portfolio, though that matters too. Your greatest asset is your passion. It is your adaptability. It is your strategic focus. And friends, those things do not have an expiration date.
Now, I want you to remember another phrase, and this one is just as important: “You have to surf the waves of innovation.” Let that sink in for a moment. It is not just a catchy saying you put on a coffee mug. It is a blueprint for success in today’s lightning-fast business world. Imagine, if you will, that you are standing on the board of your entrepreneurial journey. The waves of technology, market shifts, and global competition are coming at you from every direction. Some of them you can see building on the horizon. Others come out of nowhere and catch you off guard. Now, here is the truth of it—you cannot predict these waves. Nobody can, no matter what they tell you. But you can learn to ride them with skill, with grace, and with unwavering determination. That is the difference between thriving and just surviving.
Picture this with me: A businessman and entrepreneur who is not afraid to admit he does not have all the answers. Now, I know what some of you might be thinking. That sounds like weakness. But let me tell you, friends, that is strength. Real strength. You see, running a business is a lot like steering a ship through rough waters. You have got to be flexible. You have got to be brave. And most importantly, you have got to be honest—with yourself and with your crew. The captain who pretends to know everything is the captain who runs his ship onto the rocks.
Now, listen closely to this next phrase, because it took me years to learn it: “Pivoting requires you to be wrong.” Let me elaborate on that, because it is not comfortable to hear. In the world of business, the ability to change course is not just a skill. It is survival. Those who are so married to their original idea that they cannot see when it is time to shift, well, those are the ones who get left behind. True leadership, the kind that lasts, is about having the humility to recognize when your current path is not working and the courage to chart a new course. Humility and courage—those two go together more often than people realize.
Now, this is about working seven days a week, every moment you are awake. But here is the thing, and this is important—it is not just work. It is passion. It is purpose. It is the American spirit that has always believed tomorrow can be better than today if we are willing to roll up our sleeves and make it so. And here is the beautiful part, the part I want you to carry with you: You are not pretending to be some superhuman. You are real. You are human. You make mistakes. You get tired. You wonder sometimes if you are on the right path. And that, my friends, is exactly what makes you capable of something great.
And that, my friends, is exactly what makes you capable of something great.
Now, I want to speak directly to those of you in the later chapters of life, because I have something important to say. You see, just because you have retired does not mean the waves stop coming. They never stop. They just change. And here is the beautiful truth that too many people miss—you do not have to ride the giants anymore. You are not competing at Waimea Bay in Hawaii, where they hold the legendary Eddie Aikau Big Wave Invitational and the waves have to reach forty feet before they even start the contest. You are not charging the monstrous swells at Nazaré in Portugal, where surfers have ridden the largest waves ever recorded on this earth. No, friends, those days of proving yourself against the giants may be behind you. But that does not mean you put the board away.
What it means is this: You adjust. You find the waves you can handle, and you handle them well. That is the key. You learn slowly in the early years, you achieve peak performance in the middle years, and then—and here is the part nobody tells you—you continue to perform. You keep surfing. Maybe the waves are smaller now, maybe the stakes feel different, but you stay in the water. You stay engaged. You keep that spark alive in your chest, that curiosity, that willingness to paddle out one more time.
You see, the joy of life is not found in some finish line where you finally get to stop. The joy is in the riding. It is in waking up with purpose, in having something that matters to you, in staying connected to the world around you instead of watching it pass by from the shore. The goal, my friends, is to keep performing, to keep contributing, to keep living fully until you close your eyes for the very last time. That is not a burden. That is a blessing.
So here is my challenge to you, and I do not give it lightly: Embrace your vulnerability. Keep those knees flexible on the surfboard of life.
Our challenge together, and I do not give it lightly: Embrace your vulnerability. Keep those knees flexible on the surfboard of life. Surf those waves of change with the confidence of someone who understands that true success is not just about riding the wave. It is about controlling your approach, staying profitable, and doing what you genuinely love. It is about getting back up when the wave knocks you down, because it will knock you down. Count on it.
Remember this, and write it down if you have to: Do what you like, what you are good at, what you are profitable at, and what you can control. That is not just investment advice. That is life advice. That is the kind of wisdom that does not come from books—it comes from living. Also, strongly consider embracing my twenty-four words that summarize Stoicism: If you wake up, you had a good night. If you go to bed, you had a good day. Anything else is not good.
And with that said, as I always say, Tippacanoe and Tyler too, I’m out of here