The Monk Maverick Who Sold his Ferrari Aston Martin or What I Learned from Driving a 10-year old “Clunker”

A hat tip to Robin Sharma for inspiring the title of this post with his book “The Monk who Sold his Ferrari”.

I read that book ages ago. My story is different than the high-powered attorney character in Robin’s book. For him it took a heart attack to change – mine was from following my heart…

This is a bit longer than many of my other sometimes posts because it takes some time to unravel how I deeply rewired my personal story of success, goal setting and even self worth.

I’ll get back to my Aston in a moment but to really understand this – it’s important to consider what cars fundamentally represent.

In our western society, the idea of the automobile has become entangled with freedom and personal expression. (I think this is changing with millennials valuing a sharing economy but this is what I grew up with.) No doubt, we derive a *LOT* of our identity from what they drive.

I can see it started early for me.

Like a lot of kids my age, I grew up fantasizing about exotic cars with posters of Porsches and Ferraris on my wall. I remember for my Bar Mitzvah calling my parents up to light my final candle and I said something like, “I’d like to call up my parents who have given me everything I’ve ever wanted…except a Porsche.”

When I was 16 years old, my dad made me a deal that I could get my dad’s Toyota Corolla if I went out and actually sold medical equipment and cold-called on Docs. While my friends were living at the beach, I was “stuck” selling medical equipment. (Though looking back I realize how much of a massive head start I got in sales and marketing education.)

In fact, I found my very first journal that I kept for about 6 months when I was 15 through 16. This is start of the entry about how excited I was about getting a car. (And then I went on to write about the 3 girls I was excited to give rides to and try to hook up with.)


My first car was definitely a turning point in many other ways too.

Not only could I take girls out on dates and go where I wanted – but I discovered something else too. I followed Brian Tracey’s advice of creating a “university on wheels”. I would constantly be listening to marketing and self-growth materials. I know a little strange. My friends would ride around with me and wonder what the hell were all these “weird” tapes.

Every car I had held a special place in my heart from road trips, adventures taken or simply feeling a part of you in some way. I bet you can remember all your cars too.

I actually named them too. It started with “Carol the Corolla” when I was 16, then “Nat the Nissan” (a 240 SX) and then “Izzy the Integra” (Acura GSR).

My next car was the start of rewarding myself for doing well in my own business. (And coincidentally they all never got names for some reason.)

It was a Honda S2000 and because it was a really hot car, U.S., dealers were charging a premium. I wanted a particular color combination; silver (obviously) and red leather interior. I literally found like 2 or 3 in the entire country and they were charging $3,000 or $4,000 above sticker. But I grabbed it anyway and made my brother come with to upstate NY to drive it back down. We thought we’d have a fun road trip driving the convertible home but it rained the whole 8-hour drive!

My continued growth and success with all my online ventures fueled my desire for my next upgraded ‘want’ – a Mercedes convertible. I remember considering the SL550 and while I was deciding, I had a speech down in the Keys. So I found a luxury car rental place in Miami to rent a car. The good news is they had the SL55 AMG model available (that’s the $30k upgraded sports version). Talk about a puppy dog close. Well after driving that around for a week, my mind was set to get that model. No worries, I’d just create something else to sell. Easy.


So far so good.

As I was increasing my business success, I kept rewarding myself with cooler and more expensive toys. That’s what we’ve been taught, right?

Funny story. I really babied my AMG and didn’t let anyone eat or drink anything in it but one of my friends did help me see it was ‘just’ a car.

This really hit home to me spending time with my friend, Corey Rudl, before his untimely death. He had a new Lamborghini and we went off to the local smoothie place in La Jolla. Corey forgot he left his smoothie on the armrest and as he accelerated out of the parking out it spilled all over the interior of his car. He just sorta laughed and didn’t freak out so many others might have. From then on I was pretty lax about my cars, including the next one…

Silver…Yanik Silver

After a few of the Underground seminars I got the itch to buy THE iconic vehicle closely tied to 007, the Aston Martin. The model I loved was the Aston V8 Vantage, and it’s been called one of the world’s most beautiful cars. I custom ordered it and had each and every design option personalized, including the door sills that read: “Hand Built in England for Secret Agent Yanik Silver”. I bet the factory thought I was a complete dork but I was a happy dork.

Now when you have an Aston you also get to do some fun stuff. Here’s a pic with George Lazenby, who played James Bond in On Her Majesty’s Secret Service.


I definitely enjoyed driving the Aston but if I was being totally honest it wasn’t a carefree enjoyment or upkeep. These cars are handmade & bespoke and sometimes act the part. It’s not like I can take it to Jiffy Lube for maintenance either. I would think about where it was parked on the street if it was ok. Or if I used the valet, would they ‘Ferris Bueller’ the car? And I couldn’t drive a dirty Aston, right? So I had a special guy come detail it every other week or so.

My wife, Missy, never really loved it either. She thought it was too conspicuous and hated how it drove. Too bumpy for her and too low to the ground so we hardly took it out on dates. My kids called the car the ‘noisy’ car and I guess that was accurate since I added an awesome quicksilver exhaust. However if I’m really sorting out the deeper feelings – I felt a little bit of judgment. All sorts of heads would turn as I was driving it. I imagined I could hear the thoughts in their heads, Who is this young “kid” with an Aston? Is he a trust fund baby? A drug dealer? What’s his real story?

Now having an Aston with a young family is also not super practical so needed a 3rd car. We decided on a 2006 Acura MDX as a reliable back-up if we both needed to take the kids somewhere.

The Success Trap

It’s right around this time that things started changing. From the outside, most people would think I had achieved total success. I was making a lot of money online by truly helping people. I had built up a great reputation in the marketplace, drove a cool car, had an incredible family, lived in a nice neighborhood, etc.

Don’t get me wrong, I was (and still am) extremely grateful and appreciative for everything I had, but I just wasn’t totally happy.

Steve Jobs talks about keeping all the passions in your life because you cannot connect the dots looking forward only looking back. There’s a certain bliss that comes from following your passion and turning into a successful endeavor – though there’s also a potential glaring issue that arises.

For me, one of my biggest passions has been unique experiences and adventure. I had an idea in my journal for a long time about combining a lot of different aspects of what I love into a company called ‘Maverick Business Adventures’. The notion was to have once-in-a-lifetime trips for entrepreneurs with business building sessions and philanthropy built-in.

I loved the idea!

And that was part of the problem. You have to be careful to keep some of that passion in check with a pragmatic business model or allocating a certain amount to bootstrap the venture.

Fast forward a little bit and I had sunk about $400,000.00 into this new venture. I had done a lot of financial juggling, like having one company pay for a sponsorship for another instead of letting it stand on its own two feet. But it all came to a head when I faced facts and realized we were not heading in the right direction.

I’ve learned the universe will continue to bonk you on the head with increased severity if you don’t figure out the lesson waiting for you.

I needed to make payroll and pay several vendors, but we were short $70,000.00.

Not good!

Normally I’m a pretty laidback guy, but I was really pissed. Mostly I was just angry at myself for letting this happen. I don’t usually have a temper, but I heaved a cereal bowl at the wall.

Damn it!

I mean, how the hell could I not fix this? I pretty much had the Midas touch with all my business ventures before. But now, something I cared so deeply and passionately about was going south…and dragging my other businesses down along with it. (The full story is in Evolved Enterprise.)

It took selling my Aston to pay for payroll to get my attention. (I still have a small dent on the wall where I threw a plastic cereal bowl as a reminder.) It was pretty much either sell my car at that point or my ticket to space on Virgin Galactic for extra cash to help the company through the crunch. I figured cars come and go—but a ticket to space is pretty awesome. I definitely value experiences more than ‘things’ so this was an easy choice but not that easy decision for my ego.

Feeling Like a Cliché

Selling my car back in to the dealer felt like I had failed. They were probably thinking here’s another guy who overextended to buy an Aston and then went belly up. It was also a little more painful since I only had about 5,000 miles on the car and lost like $60,000 on it. Ouch! But I did what I needed to because the quick transaction paid for expenses to keep the businesses going.

The publishing business was faltering since I wasn’t paying as much attention and my passion wasn’t there anymore. However, I could have gone back to it full time and saved my Aston – but I wasn’t willing to give up on what I thought was there with Maverick.

It was a longer process than I thought, but we did turn the company around, change the business model and now I’m proud to say it’s very solidly in the black.

Looking back at this experience, I’m actually incredibly grateful for not getting it “right” the first go around. I’m thankful for those experiences because it forced me to truly decide if the vision for what we were building was worth it or not. If I was just creating a fun adventure company, then, no, it wasn’t worth it. It was my love for a bigger mission for “changing the way business is played” that kept me going to figure out how to make it work.

Now selling the Aston got my attention and forced me to address what was going on in the business but that wasn’t it. I had also truly figure out how to separate my self worth from my business. I could have easily bought or leased another “suitable” car but I knew there was a bigger lesson here.

My paradox was grappling with my identity.

I am still a successful entrepreneur from my past accomplishments – but here I am driving around in a dinged up SUV as my main car. Even worse, would I be looked at some kind of ‘fake’ because I didn’t have the hot car anymore?

And these were just a few of my thoughts from mid 2010 in my journal:

“It’s slightly agonizing to see how our response rates are dropping and my friends continue to pull multi-million dollar releases. I’m not jealous because that’s not me – however at this point a ‘quick’ mil would go a long way. Some of my confidence is certainly shaken with the results we’ve had. A few years ago – I thought nothing about creating a product to make an extra 100k. Now when we got in financial trouble – I sold the Aston…I’m not too heart broken because I’m sure I’ll get something else cool. And I’m not really yearning for anything in the moment, but that might have to do w/current financial position as well. Regardless, I know I’m in a transition period and looking forward to the next chapter in my life & business…”

As you can see I had felt like my self-assurance was shaken and the idea of “writing my own” ticket to create big chunks of revenue with my list seemed like something I did in the past. Though there was some optimism about a transition period.

Of course, everything I’m talking about doesn’t just apply to a car. If you’re an entrepreneur your identity might be significantly tied to your business, your bank account, your house, your country club membership, your vacation destinations, your <insert your own identity piece here>, etc.

You name it.

I have a colleague who is selling is selling his multi-million dollar, custom-built home because of business downturns. It happens. However what happens next is up to you. You get to decide the story you write for yourself and the meaning you take from it here.

You can get stuck in regret.

If only I had done this differently or made a different decision – I wouldn’t be in this spot. Regret is tied to a feeling of being attached to the past and you cannot move forward until you actually surrender to a deeper reason-why coming forth.

Or you can be attached to recovering your past.

Perhaps you believe once you get back to $XX per year – you’ll be successful. I had to get over this too because it creates an attachment to some time in the future when you’ll be happy (maybe). It doesn’t allow you to simply BE. For some time I thought I needed to get back to my highest income level in order to feel like I’d made it again. But holding out on to these stipulations only creates tension because you haven’t hit the ‘ideal’.

In the moment all of this feels incredibly painful because you’re not trusting life has something more and better in store for you…

In another journal entry I caught a glimpse of this:

“Selling my Aston Martin has been a bit of a wake-up call…These 3 years combined with the economy tanking has exposed some significant holes in my business…and now with passion waning for info/Internet marketing revenues have fallen significantly too. But I cannot really go back to ‘just’ being an expert or online guru. I feel like I’ve evolved and my destiny is to have a much bigger ripple effect…”

Then in October 2010, I had a 2-page journal entry that envisioned my 40th birthday happening approximately 3 years later. Part of the narrative was:

“…It’s a great Fall day so I’m taking the Fisker Karma to my trainer…”

I had also written some specifics about net worth, how much I’d contributed to charity, my work, who I was celebrating with that day, etc., trying to really capture my ideal, perfect day upon reaching my fourth decade.

Well, a few weeks before my milestone birthday, I went back and found that entry. At first glance, I was a little taken aback because I didn’t really hit that many of the specific goals.

I told Missy about the entry, and after seeing what I wrote, she asked if I was upset that it wasn’t quite here. I thought about it for a second and said, “No.”

And that’s because the essence of the goals were there and even exceeded.

The dollar amount I wrote in my journal was $2M in profits coming in from various business ventures per year. Nope, wasn’t there.

But what’s the real essence behind that? To me, it’s the freedom to work on what you want, with whom you please, and on what gets you excited!

Actually, I don’t need two mil a year to have that, and you wouldn’t either. I already have the essence of that goal. It’s just about creating freedom from passive income or designing your business to support your most important contributions.

I had also jotted down other specific goals too, including giving away $5,000,000 to cause partners. I didn’t hit the $5M in charity contributions, but we are at $2.5M+ and even more when you factor in the ripple effect through other members. Once again, the essence is there.

Allowing Something Better

One interesting goal I had written down was that by the age of 39, I would go into space on Virgin Galactic. Well…that timing is not of my own doing. It’s still happening and coincidentally, Virgin Galactic threw a party for 400+ future astronauts exactly on my 40th birthday.

But even better, I spent time with Richard on my birthday for the Virgin Galactic event and again roughly a week later when I was invited to a safari in South Africa to support his Virgin Unite foundation.

All of this is something I couldn’t have pictured happening in this way or scripted it out any better. That’s why having the essence of what you want works. It gives you the flexibility of not being attached to how you think something will appear. I’m always in awe of the surprising new paths opening up or meeting the right person or being handed the right book that allows your “goals” to unfold in extraordinary and wonderful ways.

But back to the car…I wasn’t driving a blue Fisker Karma or anything remotely cool. (Interestingly enough, I probably wouldn’t want a Fisker now with all the issues they experienced.)

Truth was, I wasn’t really in a spot to buy another exotic car but I did want to hone in on the feeling behind the car I wanted. To me, it’s about having joy and satisfaction from driving it and something that reflects a bit of my fun-loving spirit.

The requests most of us make are for things (better car, bigger house, closing the deal, etc.) and are not at the same level as requests that come from your heart and a deeper place.

“Learning to receive is learning to ask for the essence of what you want, rather than the form.” – Sanaya Roman

Here’s my full journal entry a few days before my 40th birthday considering this notion:


I wanted “something that brings joy, satisfaction to drive and reflects my personal spirit.”

The BIG Realization that Changed Everything

It was around that point I realized it actually had to start with what I already had, my “clunker” MDX.

Like everything else in your life, what you appreciate – appreciates and expands.

I’ve always practiced regular gratitude journaling. I absolutely believe in this principle but I had never done it around my current car.

I started feeling immense appreciation for all aspects which I had previously taken for granted or even resented a bit.

I was thankful for the easy ownership and reliability. I loved not worrying about if I threw dirty paddleboards in there from the river or not. I was appreciative of creating a personal oasis by listening to CDs inside. I cleaned up the car and started taking better care of it. And I could feel a shift happening when I got in the car. I sometimes even drove in silence and just paid attention to the sound of the engine or felt immense gratitude for all the hundreds of parts and multitude of people it takes to even make cars possible. (It will boggle your mind when you reflect on how many hands touch a vehicle before it gets to you.)


My feeling of Appreciation was Absolutely and Totally Expansive

And I remember knowing I had really started coming out the other side of this link between what I drove and my core identity when I saw Aston Martins on the road. They are somewhat rare so it wasn’t that often, but I had always felt a little blip of angst. Then in one moment it changed in an instant. It was a beautiful spring day and I saw a convertible Aston heading towards me. Now instead of any regret, I simply blessed the person driving it.

This is going to sound a little strange perhaps – but my MDX also started magically opening up to me. There were these incredible synchronicities that would happen with the time on the clock, a meaningful song or a digital readout in someway. Actually one that really stands out was when I noticed the odometer was about to hit 55555 miles and just at the moment the CD player was 5:55 into the track. I snapped a pic while driving just to capture this moment (it’s a tiny bit blurry as I was moving):


And this was part of my journal entry from that day:


The Subtle Shift

The audio program I was listening to at this exact time had immense significance too. Here’s the exactly message from that exact moment, “reaching a shift that’s not always readily apparent, subtle but meaningful. No turning back.”

And I’ve definitely felt that shift everywhere…

In fact, I’m happier, more content, and more at peace than ever.

And finally I was feeling ready to get a new car.

At first, I considered something simply utilitarian but that didn’t fit my criteria. I could simply continue driving my MDX in that case. I considered getting an old, vintage convertible but not super practical for the kids. I also looked at the MINI cooper Countryman and almost pulled the trigger – but not quite. Something didn’t light me up about it.

Then a few weeks back at Jayson Gaignard’s MasterMind Talks, I ran into Tony Hawk outside our hotel getting out of his car, as he was a surprise guest speaker for the event. I knew Tony from a Zero-G experience we put on a few years back – so I walked over to say hi. I noticed he was driving a different model MINI cooper that I hadn’t seen before and I really liked it.

And that chance encounter was enough to nudge me back to MINI and check out a new Clubman model they were releasing. It just fit my personality so well; Quirky, unique, fun and zippy. (Interesting thing is reading through these old journal entries – the one from 2013 actually mentions MINI as an option.)

The Last Minute ‘Gotcha’

The day I was taking delivery on my car – I also I had had a breakfast meeting with a new friend who was in town. She’s a remarkable business leader & philanthropist dealing with some very significant projects they fund. Our time together flew by as we discussed mutual projects, ideas and philosophies.

We walked out of the hotel together she asked if I had a car to give her a lift to her next meeting. That little pang of embarrassment hit me and I hesitated for a moment. She told me it was no big deal and would just take Uber, probably thinking it wasn’t convenient for me.  I realized this moment was the final “tie-down” for everything prior.

It was silly to think twice about giving her a ride.

Sure this woman deals with mega millionaires, Hollywood celebrities, world leaders, etc. and here I was in my 10-year old MDX. I knew it was wouldn’t matter in the slightest unless I felt like it mattered to me. Previously I might have made an excuse about the car not being much – but I actually told her it’s her lucky day since she gets to have the last ride with me. And our conversation on the way to her next meeting actually helped me conceptualize some of these ideas to share them here.

With a joyful heart I went to the dealership and picked up my MINI Cooper Clubman awaiting me. (BTW – a little plug. If you’re around the DC-area contact Jenn Barreto at

I’ve always been impressed with the job MINI does of building a community and creating a positive identity for their customers. I’ve talked about them before in presentations about building tribes. Originally when MINI came out they really celebrated their smallness by going after SUVs. The ads and the marketing featured an “Us” vs “Them” feeling that creates cohesion. They also use unique insider language. If you love MINI – you’re a MINIac and you don’t just drive a MINI – you motor!


And here’s the first pic Missy snapped when I got home (funny thing is I almost wore matching pants):

For the MINI, I’m also bringing back the tradition of naming my cars. Feel free to guess the name. Hint: The color reminds me of water and flowing easily through life.



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  1. Really fantastic post man. Thoroughly enjoyed it and good to see another entrepreneur who’s been through this journey.

    Memories of necker,

  2. Your post moved me more than my Toyota!

    I just loved it!

    My you have terrific travels and awesome adventures,


  3. Wow! I just read this and – talk about synchronicity – it was the perfect message on the perfect day. I have been seeking the “why” or essence of why I want the things that I want.

    Just loved this post!!

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