Confessions of a Gary Vee 2017 Flip Challenge Dropout

I started 2017 so well when it came to hustling.

I’d work my tech sales job during the day, then spend the evening on LetGo, OfferUp, Craiglist and eBay, buying and selling, with every intention of hitting Gary Vee’s $20,017 flip goal.

I did well for the first few weeks, diligently tracking my profits, margins and inventory. At some points, I was on track to hit the lofty $20k goal and earn significant income. I wrote blog posts about the Flip Challenge, recorded videos at junkyards, interacted with other flippers on Twitter and took dozens of trips to the local post office to ship out sold products.

I might have singlehandedly influenced the stock prices of shipping tape manufacturers.

But life happens. In May I sold my car, quit my job, donated many of my possessions and packed a few bags (plus a mountain bike) and moved to Montenegro to live with my longterm girlfriend.

(This was a decision with much more consideration than the previous paragraph might indicate.)

I spent the next couple months adjusting to life as a full-time freelancer, navigating a new culture and language, plus exploring new parts of Europe. I deleted OfferUp and LetGo apps from my phone. My meticulous sales spreadsheet sat unused as a Google Sheet. My frequent eBay sales stopped.

Montenegro doesn’t have the same opportunity for flipping like the US does. For one, my Montenegrin is lacking to do any serious negotiation in buying or selling. And, even if I could buy and sell, shipping anything out of the country is expensive and would eat my profit. I gained a new respect for many of the European flippers who I’d seen struggling through the Flip Challenge due to shipping costs and geographical limitations.

Initially, I felt a little guilty about dropping out. I’d seen the earning potential and enjoyed reinvesting my earnings into new items. I liked seeing updates from others who were discovering their potential, both financially and personally. Gary’s encouragement of getting off the couch and using your free time to make serious money and gaining skills resonated— but it simply didn’t make business sense once I was across the pond.

Short-lived guilt

These feelings of guilt didn’t last long.

Since I was 15 years old, I’d worked for someone else. I’d always flirted with self-employment and side hustles. I’d detail cars, sell car parts and modify watches, but at the end of the day my living came through a paycheck signed by someone else. It was clear to me, however, that I was my happiest and most energetic when working for myself or a few clients I enjoyed partnering with.

Moving to Montenegro meant I couldn’t flip, but it pushed me to finally pursue self-employment through freelancing. For the first time I got to choose what I did each day. After working in sales where I’d become used to a work-or-starve mentality, freelancing wasn’t a difficult transition and I attacked the freelance market with the same business development mentality I’d built over the past few years.

My career transitioned, almost by accident, to becoming a copywriter. I expanded my marketing knowledge and skills and offered sales consulting for startups who need sales guidance.

The Flip Challenge’s Effects

Importantly (and quite serendipitously) the 2017 Flip Challenge came to me at a critical time in my life. More than the income, I gained realizations more valuable than the financial profit.

The Flip Challenge showed me the value of hustling once again, something I’d nearly forgotten after working for others.

The Flip Challenge let me take small risks and build up a feeling of confidence in my abilities.

The Flip Challenge showed the value of good content and marketing and the power of social media as Instagram became a great platform for selling.

The Flip Challenge helped cement some basic business accounting and business math skills into my repertoire.

The Flip Challenge exposed me to manageable failures that made larger failures much less intimidating.

The Flip Challenge underscored the idea that making money isn’t necessarily glamorous or easy— but a lot of fun.

The Flip Challenge helped me set a dollar value on my time, something critical for freelancing, to determine whether or not a sale was worthwhile or not.

The Flip Challenge awakened what it’s like to work for the love of what you do and that it’s possible to stay up until 2AM absolutely buzzing, loving your work.


To others still flipping

From a few searches on Twitter, the Gary Vee 2017 Flip Challenge is still roaring along for many people— and some are even brave enough to jump in 10 months into 2017.

If you’re still flipping, keep up the hustle. But whether you hit that goal or not, focus on what else this challenge gave you. You might be surprised to see how much your mentality, appetite for risk and business skills have grown since you first started.

Whether you end up making $20.17 in profit or $200,017 in profit, the value of the growth possible from this challenge far outweighs the monetary benefit.

And, for that, I’m grateful for Gary Vaynerchuk’s challenge.


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