Why Every Entrepreneur is a Skydiver

I was out having a nice dinner with some friends while in San Francisco a couple weeks ago.

It was a much needed reprieve from the daily grind. I felt like I was turning into Bill Murray in the movie Groundhog Day, and needed a change of pace for a few days.

Recently, I’d also ended things with a girl I was seeing, which was a little tough, but good friends and good food can put everything back into the right perspective.

At dinner, everything was business as usual.  The gang was talking about the usual topics, but then we started talking about fear.  A girl seated next to me brought up skydiving as her biggest fear.  Having done it already I chimed in how awesome it was. She turned to me and asked, “yeah, but what’s the point?”

What’s the point!?

Seriously?  I looked at her unbelievingly for a second.

I’ve done skydiving once before, seven or eight years ago, and was quick to say, “It’s all about the experience. It’s an exhilarating rush you feel throughout your body that’s like nothing else on earth. Jumping out of an airplane at 13,000 feet is one of the scariest things you can do! If you can do that, you can do anything.”

She wasn’t convinced. To be honest, at the moment I wasn’t entirely either. What I was saying is true, but it just didn’t have as much gravity as I wanted, no pun intended.

Entrepreneurship is About Facing Fears

Being an entrepreneur has everything to do with what you think and how you feel. You’re living in the present moment and putting yourself in charge of your life and guiding yourself into a new future. Sometimes, you feel like you’re freefalling into a leap of faith. This is the fear of the unknown, and it can affect every entrepreneur’s attitude towards how he or she views their work.

What if the dream I’ve devoted myself to doesn’t work out?

What if I fail?

Personally, I was beginning to feel a little stuck, and unsure about my future.  I was overly worried that I’d make a mistake, or make a fool out of myself.  I left the restaurant and didn’t give it any more thought.

My younger self, in my twenties, was fearless and that’s what led me to building such a great career for myself as a digital marketer and entrepreneur.  I could look that jump square in the eye, and do it every single time.

My first entrepreneurial “jump” came with Sujan Patel and his cousin, marketing legend, Neil Patel.  We created the best digital marketing agency in San Francisco at the time, over two million a year in revenue. Our clientele consisted of small businesses, venture-backed startups, and Fortune 500 companies. The next was with Kimberly Snyder, a celebrity nutritionist who I helped build a multi-million dollar business that started out as a food blog.  We created digital products and we even did branded partnerships opportunities that helped us to white-label physical goods.  The success of our online brand resulted in NYT best sellers, partnerships with big brands, and Kim even co-authored a book with spiritual guru Deepak Chopra, which netted her multiple six-figures. As an author, that’s a pretty sweet win, considering most authors don’t receive any advance at all.

Since I’m in my thirties, now, I realized that I’ve been “coming of age” and I wanted to prove to myself that I was still fearless.

Age, time, and work have a way of making you feel less brave.  Back when I was eighteen I promptly moved out of my parent’s house and went to college. Then, I decided that making money and creating a career was more important than learning about Socrates.  I could read at night, and make money during the day.  I was fearless. I dropped out of college and never looked back.

I know that I will be using the lessons I’ve learned in my twenties as an entrepreneur in the next stage of my journey.  Especially what I learned from my million dollar agency, Single Grain, which is still up and running today.  Now, Single Grain is owned and operated by Eric Siu, a passionate CEO who is helping Uber, Amazon and some of the best companies out there.  It’s great to see that my hard work with that company was able to help them build a strong foundation.  When I ran the company with Sujan, we grew it to over 70 clients and 20 employees in San Francisco.

I was on top of the world, but I had to keep moving and start a business that was 100% my own.  I sold my shares in Single Grain in 2013 and jumped without a safety net.  I had received some of the best mentoring in the world working with Neil and Sujan, and I was in for a real shock when I didn’t have anyone else’s ideas to lean on.

With Limitless Publishing I started doing joint ventures and helping others to build bigger businesses that were built to scale. I leveraged popular personalities and brands in order to find partners who I could really make an impact with.  I put everything I made back into the company almost half a million of my own money, along with a big investment from my parents.  Years of my life went into figuring it all out, but I was finally onto something big.

A few years into Limitless, I faced something that a lot of entrepreneurs go through. Depression and anxiety.  I was forced out of a joint venture company that I helped to build.  My partners turned on each other and I became the odd man out.  The company was running on its own, based on the systems that I helped to implement.  I had created my own monster.  The company no longer needed me, because everything was running so smoothly.  I had shareholder’s rights, but I couldn’t afford years of dragging it out in court with hundreds of thousands of dollars of legal fees.  I felt vulnerable, exposed, weak, and emasculated.  A lot of millennials have felt this way due to the changing nature of the job market, the economic collapse of 2008, and the uncertainty of job security.  Obviously, entrepreneurship comes with its risks, but when you build something that is making millions of dollars, you don’t think about getting cut out.

On the Fast-Track

I feel stronger and more powerful today than I ever do, probably because I faced a humiliating defeat. Having to restart meant that I was able to figure out the system, the map to creating value–FAST.

I’ve worked on building companies for more than ten years, and with my experience I know I can do in 1-2 years time, what it would have taken me five or six to do before. I’m getting faster, and I’m more confident.

Because I have the map. The system. And that system works. I believe in it. Emotionally all that I went through, helped to empower me. All that pain was fueling my fire.  If it wasn’t for that. I wouldn’t be here, in a position for massive success and growth.

Since then I’ve had all of this stress, fear, humiliation and emotional weight that has been nagging at me. I was feeling burdened by bills on top of all of my business expenses and I just wanted a simpler life.  So, I moved back in with my parents, like so many other millennials, and started to rebuild.

Today, I’m using my parent’s house as a home base and living in AirBnB’s traveling as much as possible. I’m a citizen of the air.

But for a while I truly felt like I was moving backwards.  Every new venture, every contract, every piece of the puzzle was just something else to come unhinged.  I believed that it would work, and a lot of my successes started stacking up, but then as quickly as it worked, something would fall apart again.

Sometimes you have to take a few steps backwards, so you can take the giant leap forward.

As an entrepreneur you are an artist, you call the shots and conduct the orchestra, so to speak.

I had so many passions that I was pursuing full-time, and it just felt like nonstop action for a while.

I needed to get away, and I needed to remember who I was…

The Call to Adventure

The next day, as I was driving from San Francisco back to my home in Southern California, I noticed people were falling out of the sky in parachutes. I pulled over, and “Yelped” skydiving and saw that SkyDive California was less than a mile away.

“Should I do it?”

My mind raced through every excuse in the book.

I haven’t eaten enough.

Oh, I didn’t shave this morning.

Am I wearing the right clothes?

Should I spend the money, I’ve already done this before?

What will my friends think?

What if I die?

Should I call my parents, what will they think?

All of these thoughts invaded my mind and tried to force out any bravery that I’d gathered in the last few minutes.  The more that I focused on them, the less I wanted to go.  But I quickly realized that these were just a response to the truth: I actually wanted to go skydiving today.

This was just a test, and I knew it. I ignored the voice in my head and turned my car around.

Why Jump?

It’s scary because you are scared of dying when you jump, but excited to live as you’re tumbling rapidly towards the ground.

It addresses the constant fear that we all have: what’s coming next?  We are afraid of the unknown and afraid of ourselves. What if we take this risk? What if I don’t make it. What will my friends think?

It can be exhilarating, but very scary all at the same time.

As entrepreneurs, we want to become aware of the fear, but also be able to surpass it. If you can’t get over your fears, you will probably not have a lot of success.  Everyday you are facing rejection.  Someone could say “no,” or tell you that someone else’s product is better.

The only thing that you can do to control it, is to pack your parachute to the best of your ability and jump.

Be Open to The Unexpected

At one point a vision of a Post-it Note that I use to have on my bathroom mirror flashed through my mind, as I was driving to the jump site. It reads, “I am making a quantum leap. I know exactly where I am going and I’m open to the unexpected.”

That’s the best part about this metaphor, you can plan out where you are going, but you never really know where it will take you.  I was open to the unexpected, and that’s why as I drove by SkyDive California, I wasn’t afraid to try something different.

I saw the people falling out of the sky, in colorful parachutes, and it looked like a lot of fun.  Sometimes, you can’t deprive yourself of great experiences that can lead to a more enriching life.  So, I went there, and pulled out my Smartphone to send a couple messages to my friends.  That’s when I began feeling the fear.

I thought maybe I was being stupid.  I mean once you’ve gone skydiving, it’s sort of insane to want to do it again.  I was looking at the pictures in the tiny waiting room thinking about whether I should add-on the photographer as an extra cost.  That’s when a guy who was there just chilling on the couch and wasn’t an employee, said “if you jump out of a plane at 13,000 feet and no one was there to see, did it actually happen?”

Entrepreneurship is a Journey

Now back to the part where I jump out of a moving plane and hurdle to my impending death…

The plane you go up in to go skydiving isn’t the greatest.  There’s no first class.  It’s a bare bones, no frills sort of experience.  Bootstrapping a company is very similar.  It feels like you need to eat ketchup sandwiches like Mark Cuban did, just so that you can invest every dime back into your business.

You literally sign your life away when you jump out of this crappy plane.  We live in a world where fidget spinners are the new way to remove stress.  But what really removes stress is knowing that your life is on the line.  This may seem counterintuitive, but when surviving is all you can focus on, there’s no room for thinking about how your hair looks in your selfie, or when that client is going to be signing that contract.

It’s all insignificant compared to what is really important–living your life.

Even when I was psyched and ready, the guy who was my tandem jumping buddy was a student from Sacramento State and he was a little nervous.  He was talking about how we have to use the bigger parachute, and how he normally prefers the smaller parachute, and most of his team prefers the small parachute.  He didn’t realize it because he was just at work talking about his job, but it would have been pretty nerve wracking for most people. But I wasn’t worried, I was ready.  Actions always speak louder than words, and I wanted to drive the fear out of my mind and body. It was like I had a new state of mind.

As the doors slid open, I was thinking about some of these parallels, and I laughed a little bit.  That’s when it hit me.  I knew I was about to jump out of an airplane, just as many entrepreneurs realize that they will be reliant on themselves for full financial support after they leave the safety net of their job.

But what no one really can prepare for, is who you’ll show up as in that moment.  Who will you be when the doors open and you’re strapped to your jump buddy–aka your business?

In my case, I didn’t have time to figure it out.  I just jumped as the cameraman told me to smile big for the camera. My jaw has never dropped so hard.

So the moment that builds up is pretty incredible, as you’re waiting to make that jump, to actually falling out of the plane.

People always have a hard time describing what it feels like to jump out of a plane. A lot of people try to compare it with rollercoasters and how it feels like to go through the drop, but it’s not like that at all. You’re jumping from a height of 13,000 feet with only a parachute stopping you from becoming dust on the ground.  Roller coasters have seatbelts and have gone through thousands of tests.  A parachute is something that someone rolled up together right before you got on the plane.

Aside from just the sheer thrill of the risk, the exhilaration from going from airplane to free fall is pretty intense and that’s when the transformation begins. Skydiving is amazing because it is one of those purely transformative experiences.

You are risking your fucking life. They make you sign a very clear contract where you initial almost every line just to make sure you really understand what you’re doing. Of course, I just blazed right through it.

I didn’t care. I was so confident that I needed to be doing this.

Just like in some of my past business negotiations, I was meeting with VCs who were willing to stake me for hundreds of thousands of dollars.  They never really cared about the money, they just were waiting to find the right opportunity, and when I was that opportunity, they jumped. Period.

I know from skydiving that when you are about to go from being in the plane to out of the plane, that everything changes.  There’s no real room for fear, you just have to force all of your attention on what’s happening in the present moment, because you know you will never really be able to get there ever again.

Only through death can we be reborn.  Not our actual death, but the death of our fears, memories which don’t serve us, and ideas or concepts which limit us.  I learned that we need to let these things die a little every day, so that you can start becoming who you really are.  And stop worrying so much about what others think.  You are not living their life and they certainly are not living yours.

When you’re an entrepreneur, you can see everyone around you launching off into space, just like in the movie Gattaca.  Everyone in your sphere of influence is launching some new shiny product or service.  It all looks so glamorous from the outside.  You are only seeing the highlight reel, you don’t see the mistakes the setbacks, and the fear that prevents people from achieving their breakthroughs.

I realized that my new software company I’m building with celebrity real estate agent, Josh Flagg, is going to be my next rocket. I have a good feeling that it is going to catapult me into a lot of success, and it’s what is keeping me going.

It’s kind of funny, because this is the culmination of all of my work–and it all came back around full circle for me.  I am incorporating everything that I’ve learned from all of my other companies and put it into this new project.  After I dropped out of college, I worked for the Mike Ferry Organization–a renowned name in real estate. And today nearly ten years later, I’m building a new software business for Realtors. I’m doing what I do best, helping them create their digital presence, even if they don’t understand technology.

It’s a new creative form of problem solving.  Instead of using clunky WordPress themes, we went to a platform developer so that we can create beautiful, luxury websites and marketing packages that provides a unique site for each real estate agent.

Free Fall Like a Maestro

You go through this exhilarating moment where you are hurtling through space and time at hundreds of miles per hour, and this camera person is taking pictures of you telling you to smile at the camera while you’re plummeting to your death, or to your glory.

After you pass the first moment from plane to not in plane, and your body is falling, you just let it all go, that’s where it happens, at that moment you leave it up to faith and enjoy that fall like there’s no tomorrow. You’re emotions charge up, your blood is coursing through your veins, a rush of adrenaline happening throughout your body builds up to it’s momentous climax, where you realize it: you’re ALIVE.

You are really, really scared for a few moments, when you jump, and then all of a sudden, the parachute opens and you feel grateful.  It feels like a great cleansing experience. Like if you’ve ever slammed on the brakes really hard when you think you’re going to hit someone, and it never actually happens. There’s that sigh of relief as you accelerate again.

In this moment I was grateful for the guy who helped me, he made sure we landed safely, and he’s funny on camera!

You Are Creating Your Reality

So I got to post all the stories on Instagram stories. And now I get to write about all of it as a way to share this experience, and hopefully encourage someone who is reading this today to make their next big jump in life.  I was creating my own reality and people can watch my experience through a smartphone. I’m writing, producing directing, and starring in my own reality show called life.  The amazing part is… you get to call all the shots!

When you forget how to take risks, you forget how to live your life to the fullest.  And when you aren’t reaching your potential you get stuck, you get comfortable, and you can’t realize that you are actually falling.

As entrepreneurs you can let things slide until you fall out of the plane and have to recover, or you can take calculated jumps.  Most people would say to look fear in the face and jump, but honestly, there’s no difference between the two jumps.  Both scenarios require you to figure it out as you fall.

Sometimes, you will have a rocky landing that you weren’t expecting.  But other times, you will have the greatest ride of your life. You just have to learn to expect success, and cling to faith rather than fear.

Your parachute will open all on its own.

Your stress isn’t helping.  Your complaining isn’t helping.

We live in a world full of opportunities, you just have to be able to be the one who makes the most of them.  When your time comes you have to be ready to jump. Don’t wait for fear.  As an entrepreneur there will always be enough fear to go around.

Instead, jump on “2” and know that your parachute will open when it’s time to.  Fear is a lack of trust, and a lack of faith.

And don’t forget to take pictures, and document your journey along the way.  I anchored that experience so that I can go back to that moment every time I want.  Remember, “once you become fearless, life becomes limitless.”

So let’s go back to my friend’s original question: what’s the point of skydiving?

Skydiving is a cleansing experience where you get to look your future straight in the eyes and say: “Fuck yeah! I got this.”

And when you do that, it’s going to work out, sometimes it just has to.

3 Comments

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  1. This is inspirational story for me. Thanks for share. My question to you when other people tell bad things to me demotivate me. How to avoid that and stay positive?

  2. What a great read. I just went Skydiving on Sunday after a rough summer of trying to lock in clients. I have always had this intense anxiety with heights and it was a surprise birthday gift from my girlfriend.

    Aftering feeling the amazing rush of adrenaline and checking off my bucket list, Iwent back to work on proposals. On Tuesday, I was able to gain a major long term client and slowly working towards a second big fish to add to our portfolio. All after a nightmare summer where I was on the verge of submitting resumes…

    Suffice to say, this story really hit home.

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