5 Business Strategies I Learned from Landing Kickflips
When I was a kid, skateboarding wasn’t just something I did—it was who I was , It was something I had a true passion and natural talent for. Since I first picked up a Skateboard I felt at home I felt like this was my destiny and boy I was good, but like REALLY good! Every scraped knee and busted board, 9 broken bones, more X-rays than I can ever mention was a badge of honor. At 16,Doctors forced me to hang up my board,I felt lost and I always carried this empty part of me around but that fire never really died. Now, at 40, I’ve returned to the pavement, I have returned to my happy place to doing the thing that challenged me and shaped me most in my life and something unexpected happened: while relearning to land a kickflip, I realized skateboarding had taught me more about business than any course or corporate training ever did.
Skateboarding, especially the pursuit of one trick—the kickflip—shaped me into the disciplined, resilient entrepreneur I am today. Here are five business strategies I’ve carried with me from the skatepark to the boardroom.
1. Fall Fast, Learn Faster
There’s no clean way to learn a kickflip. You fall. A lot. Your board flies out, you miss the flick, you land wrong, you bail—over and over again. But each fall teaches you something. You start analyzing: was my front foot too high? Did I flick too early? You start breaking down the trick into smaller movements that ultimately creates the magic! It takes time, it hurts and its super frustrating, the repetition and repetition with often no result is soul crushing yet character shaping! All the hours and days and effort all culminate to that one Kickflip you land perfectly that one you just know in your heart, YEP that’s the one I now know HOW it is done properly!
Business is the same. My first Business failed. Your first product launch may fail. Your marketing campaign might tank. Your pitch might get rejected. But every failure holds a lesson, and if you reflect and iterate quickly, you’ll improve faster than those who play it safe. Keeping your mind open to the fact that nothing YES NOTHING is perfect and that the only way to success is failure, the faster you learn how to learn! If you have a no die attitude and always get up no matter how hard that fall is and you will learn better smarter ways of doing things, you’re on the right path!
Failure isn’t the opposite of progress—it’s part of it.
2. Obsession Beats Motivation
There’s a moment when learning a trick that you cross from wanting to land it to needing to. You picture it in your head and you visualize about how good it will look when you land it, it becomes all consuming! I’ve spent hours trying to land a single clean kickflip, soaked in sweat, long after motivation ran out, tired and often bleeding. Why? Obsession. Not the creepy Joe from Netfilx series YOU type of Obsession, the healthy I want to succeed SO bad type of obsession. The obsession that you have to do no matter what it takes to nail that trick, no matter how many hours, days, weeks it takes I will not give up! Motivation to do something runs out quickly after the 5th time your already bruised and swollen ankles get twisted again and again and the adrenaline you had when started has depleted, that is where the obsession kicks in when your mind overrides your body, when it is only fight mode not flight mode, thats where you find unmatched willpower, unrivaled work ethic and when you become phenomenally good at something!
Business rewards the same kind of relentless pursuit. When you’re building something meaningful, there are going to be days you don’t “feel like it.” The days when you have no answers to the big questions , where your leadership is being questioned and people who depend on you stare blankly at their “Chief” waiting for him to save them! This is where you need to step up to that plate and put your mind into being obsessed with finding solutions and creating magic! When you are obsessed with your goals and making a difference, the hurt, the pain, the tired doesnt matter! You’re not just doing the work—you’re consumed by it, and that’s where real breakthroughs happen. Find something that you don't just love doing, create a career out of something you are OBSESSED with not just to pay bills but something you can be proud of something that you truly enjoy doing even when the motivation runs out, even when you don't have a full calendar of client meetings, keep the obsession going!
3. Master the Basics Before Going Big
Everyone wants to land a 360 Flip, but before even thinking of that we need to be able to do a basic kickflip.It’s humbling, going back to the basics—but it’s necessary and it keeps you grounded! Although my signature trick back in the day was a good old 360 flip, now getting on the board trying to “look cool” and attempting a tre’flip is embarrassing to say the least, so I had to go back to the basics learning of the kickflip, master that and soon my body remembered how it should move and react to get that 360 flip I so love! (ill attach a clip for proof)
The same is true in business. Before you start chasing viral marketing campaigns or scaling your startup, ask: is your product or service good? Are you filling a need? Are you solving a real problem? Fancy tactics and flashy features mean nothing without a strong foundation. What is your Why, yes I know it's cliche but really what is your Why? We live in a world that is oversaturated with “viral” marketing and influencers pushing products down our throats, if you have the core of your business and WHY you are doing that “thing” or selling that product right and you truly believe in it, the universe shall respond with great things and you will reap the rewards. As long as i can remember even with all the AI and Technology that we are consumed by these days, everything that I have achieved always starting with the KISS principle (keep it simple stupid) and having that as the foundation and building from there also helps you not overthink and overcomplicate things and makes it easier for people to understand what you are actually doing weather you selling a service or a piece of tech you can't go wrong with keeping it simple and sticking to the basics!
Build solid. Then go big.
4. Community Is Everything
Skateboarding is often seen as a solo sport, but it’s essence lies in the community, if you ever had a Skateboard or admired the sport you can go anywhere in the world and have instant friendships form, just because you like a piece of wood and wheels. Some of the best people I have met in my life was through skateboarding. My best friend of 25+ years met me because he had a sticker of a skate brand on his school bag when we were 14 and until today we still talk skating and have an unbreakable brotherhood. You cheer each other on, swap tips, share gear, and push each other harder than you would alone. Some of my best skate memories aren’t about landing tricks—they’re about who I was with when I landed them. My Father used to take us to the local skatepark once a month and the guys would fight for a seat in the car. All we could talk about was the next Boogaloos trip and what tricks we were planning to nail and who will be there to witness them!
In business, your network matters. Whether it’s mentors, co-founders, employees, or even online communities—surrounding yourself with the right people can accelerate your growth and keep you grounded. We have all heard that your Network is your nett worth and so on, but it’s true no more than in the current world we live in full of personal brand guru’s and business content coming out our ears and every Joe soap telling you on LinkedIn how his last Beer with a mate helped him understand B2B sales better (cringe)! I spent 20 years building a network of people that shaped my career and pretty much me as a person, but the past couple of years I have really invested in building a strong circle of peers that I trust and I know will push me to be better, think better and act better! You need people who challenge you, support you, and call you out when needed. This is in short how the Badger Cave became a ‘thing’ , Johnny and I started a weekly call talking about Leadership and life and over the time we have build a strong bond and friendship, and he has become a great mentor to me then bringing in key people from our “community” to build , shape and rebuild what we think we know about life, leadership and business, it’s where C-suit meets the kids that grew up in rough streets and bar fights, where misfits and f#%k-ups come to share their success story! No judgement, no cute MBA’s and pHDs just raw, real and authentic people sharing their experience, this is what a community should be, real , raw , authentic! Pick your Crew carefully and keep in mind you will outgrow people, your Crew will change over the years and thats even more reason to pick them carefully!
Success is rarely a solo mission.
5. Style Matters (But Only After Substance)
I have always had a thing about, It’s not what you do , but HOW you do it! Anyone can technically land a kickflip, but doing it with style—clean, smooth, confident—that’s what earns respect. I remember back in the Day I loved Chad Muska (still do), his look, his badass attitude, his music taste but most of all his skating style, whenever he got on that board it was like a well orchestrated symphony of chaos! It was fucking beatiful to watch and I always in my head thought when I did any trick , i need to do it with that Muska style or flair! But here’s the thing: style comes after you’ve put in the reps, you can't just jump on the board and WHALAAA backside flip 8 stairs and land it rolling away like a boss.. Trust me I broke my arm 4 times thinking that, nope style comes in time, with time, with knowing how to do things, understanding what looks good, what feels right and then practicing it over and over, finding the weak spots in your stance, bending your knees more, arching your arms less, it's ALL in the details! Like picking a skate spot then deciding exactly which trick will suit that environment, what can I do? What should i try, where do i start and what is the BIG thing i want to nail during this skate session, all these things matter!
In business, your logo, branding, and social media presence do matter—but only after your product or service delivers real value. Focus first on solving the problem and doing it well, what is your expertise and why would people pay for it, what makes your product or service different to others and why should people care? Like picking that skate spot then pairing it with the best trick you need to find that mix, not the perfect one because that doesn't exists, find the right mix of why and where and how and know that you should test this ALLOT! Something might look good or work today but in 3 months it doesn't anymore, keep testing keep trying . Once your substance is rock solid, your style will amplify your impact. Something that has really helped me over the years is asking outside perspectives from people who I trust (again community is important) . We all have our confirmation biases and we believe that everything we do is worth gold, but it's likely not! Make peace with that and get your trusted advisors to give you clear and honest feedback, bouncing ideas can take an idea or concept from Meh to wow thats f#*ing amazing!
Don’t skip the grit for the gloss.
Full Circle
Coming back to skateboarding at 40 wasn’t just about nostalgia—it was about rediscovering a mindset I’d forgotten I had. It connected with my essence on a whole new level, it opened my mind up to a different perspective on life, leadership, creativity, community and business. If you asked me 30 years ago when I was rolling around in the streets with my baggy pants listening to, well the same 90’s hip hop i still do, if that piece of wood would shape my business career I would have laughed and told you you are crazy, but here and now 20 years into my career, it was that piece of wood that shaped me in more ways than i can even list! The same traits that helped me commit to tricks as a teenager—resilience, focus, humility, creativity—are the ones that helped me thrive in business and life.
Skateboarding didn’t just teach me how to fall. It taught me how to get back up with intention. To never give up and never give in, to look at things from different perspectives and to be curious and find out more about things and not just take them at face value.
So here’s my challenge to you: Find your “kickflip.” Maybe it’s something from your past, maybe it’s something new. But whatever it is, chase it—not just for the joy it brings, but for the lessons it hides. You might be surprised where it leads.
For good measure here is another cool skate clip from the Old man himself!