Online Entrepreneur Timeline

I know that most people think they want to run a business. The biggest obstacle is always the question, “how do I get started?” What is the first step? In this article I provide a time line briefly explaining each of my business ventures in chronological order starting at around age 10 up to the present, at age 23. This information can be viewed as a complement to an article I wrote summarizing my business strategy.

The Timeline

  • Age 9-13: Paid staff at an overnight camp to buy me 24 packs of soda cans which I resold to fellow campers at 3/4 cost of the camp vending machines. I built a makeshift cooler out of Styrofoam to keep them cold at all times and earned around $50 profit each summer. The other other campers soon became upset that I was making money off them and demanded free sodas.
  • Age 14: Borrowed $50 from my dad to sign up for the Microsoft Xbox Live Beta program and received the service and memorabilia. I sold the memorabilia earning $50 after paying back my Dad. I used this $50 as “capital” for other opportunities.
  • Age 15: Sold a brand new TV on Ebay through a free drop shipping

    program for my first sale of an actual product, earning a little of $30 profit with no start up cost of course. This was a fake sort of drop shipping program where the products offered were typically above retail costs but I somehow sold the TV. This inspired me to put in further research to find better drop shipping opportunities once realizing earning money this was was possible.

  • Age 15: Sold high priced bootleg software such Photoshop on Ebay earning $50-$200 in profit per sale. The software was also drop shipped. This only lasted a few months until Ebay and Paypal banned me from their services. The quick and easy money excited me too much that I didn’t realize losing the use of these accounts would hurt me far more in the long run. Of course I registered more accounts in my name  each time I was banned a for a good few months until I gave up on selling these items.
  • Age 16-Present: Began selling personal items such as my old clothing on a large internet forum earning extra cash here and there. Then in turn I began selling dropshipped items such as novelty gifts, airsoft guns, and other products with decent success.
  • Age 16-17: Sold throwback sports jerseys on Ebay (again using different accounts) earning $10-100 in profit per sale. I  Found a few individual sellers in New York and Florida who drop shipped the jerseys to my customer. They were all pretty shady. I registered and set up an E-Commerce website selling the throwback jerseys without much success through the website/ But Ebay sales continued. My suppliers became unreliable and throwback jerseys lost their popularity and selling power so I stopped a year later. I earned around $10,000 in profit doing this.
  • Age 16-Present: Sold screenprinted t-shirts via the large internet forum earning $6-$12 profit per sale. I Identified interesting designs posted throughout the forum and contacted the designer offering commission for each t-shirt sold ($.50 usually). I took pre-orders (color/size/payment) from customers on the internet forum and then gave my order to an inexpensive screenprinter in California to print the t-shirts and mail them to me. After receiving a box with the shirts I packaged each individual order and sent them out from the post office. Throughout the years I have sold 2,000 or more shirts, including some wholesale orders to small book stores and museums. I earned around $20,000 in profit doing this.
  • Age 17-19: Sold strange products bought overseas to customers on the internet forum and Ebay. Traveled on a group program to Bolivia for six weeks and bought a few llama fetuses, pipes, decorated knives, and even custom printed t-shirts. It was tough to unload some of this but when I finally did I earned big profits (i.e. paid $1 for the llama fetus and sold it for $50). A few years later I tried this in Ecuador and ended up selling fake shrunken heads, vintage books from WWII, etc. on the small scale. This was fun but I realized doing this consistently for a decent income would be pretty difficult.
  • Age 17-19: Sold various products including airsoft guns, lighters, neon signs, etc. through the internet forum earning anywhere from $1-$100 profit per sale. All products were drop shipped from new suppliers. I earned around $5000 in profit per year doing this.
  • Age 19-21: Wrote a somewhat detailed business plan to someday open up my own youth hostel. It is pretty rough but covers a lot.
  • Age 20: Wrote a business plan to start my own daily product website similar to I bought the domain with the idea to sell one new poster every couple days. I had sold posters in the past which cost me $1 to produce and would sell them for $5 each. I already had around 20 cool poster designs. Designers would be paid a percentage of each sale I made. In the end I chose not to go further with idea because I didn’t really see it working well.
  • Age 17-22: Registered wholesale accounts with popular clothing brands (American Apparel, Alternative Apparel, etc.) to resell clothing through the internet forums earning $10-200 profit per sale. I received orders and had the companies drop ship to my customers even though they did not advertise this.  A few years later I even made one sale for $3,500+ to an individual purchasing uniforms for a company, earning $700+ in profit which prompted me to quit an internship and travel to the Galapagos Islands and then Colombia. I was eventually forced to order in larger quantities which meant shipping the clothing to customers myself. I continued this and other ventures while traveling overseas 4 months per year by hiring a different person each summer to ship the goods. During the school year I packaged and shipped the goods to my customers. While I was away I hired a person to package and ship orders for me. I earned around $30,000 in profit doing this.
  • Age 17-present: Created to sell my collection of drop shipped items, t-shirt lines, strange items personally imported from overseas. I found a volunteer to build the e-commerce website for free and advertised the website through the internet forums. Over the years I upgraded the website actually paying for quality and advertised more heavily with banner ads, Search Engine Product Search program, and a few successful PR activities. At one point this was my most profitable business.
  • Age 17-21: Used my resources to take advantage of easy opportunities to earn money. For instance I acted as a screen printer when I found someone wanting to order a bunch of custom sweatshirts to celebrate Christmas with his friends. This is one of many examples.
  • Age 19-20: Offered a resume/CV writing service for $20 per customer through an internet forum after seeing someone else do the same. The business developed as I received positive testimonials directly from clients in the forum.
  • Age 20: Nearly started an exotic jerkey business importing kangaroo and crocodile jerkey from Australia but decided against it. Thank god because who in their right mind would ever buy it. There’s a reason nobody else sells it.
  • Age 19-present: Started my first travel blog, JasonsinSouthAmerica, which has now turned into For over four years I wrote about my travels and businesses with no intention of ever earning money. I figured earning pennies from sources like Google Adsense or the occassional affiliate marketing sales would never be worth it. Four years later I stumbled into a very simple process to attract actual advertisers for $50-$300 sponsored post sales and text link ads. In just one month this business surpassed my online retail store as my number two earner. As of September 2012 it earns around $22,000 per year in profit.
  • Age 20-present: Started an official Career Consulting Service based on the internet forum successes. I advertised heavily and  of course I built an eCommerce website shortly after the business took off and turned this into by far my most profitable business ever. As a result this accounts for around 90% of my income. I offer resumes, CV’s, cover letters, mock interviews, and a few more services. I also received other writing opportunities such as a freelance copywriting job for a big company here and there. I don’t want this blog associated with this business so I won’t mention the name of it. As of September 2012 my average sale per order is $155 and I average between 70 – 85 new clients per month. In September 2011 I hired my first full-time employee and flew him to Philadelphia to work from my home with me. In August 2012 I hired my second full-time employee and flew him from Oregon to work for me full-time.
  • Age 24-present: I represent advertising sales for four additional websites by leveraging my advertising contacts I have built up during the past couple of years.
  • Age 24-present: Although I do not earn money from this venture I now go on all expenses paid international press trips, which is essentially free travel in exchange for writing about my trips on another website. I also do product reviews of fun items like alcohol, stereos, etc.


I currently run the career consulting business as my primary income with the help of two full-time employees, this blog and four other travel websites as my second income, as a new website, BuySomethingAwesome is now my little brother’s business, and I stopped selling the American Apparel clothing early 2010. The businesses have come a long way since I started with much higher revenue, complicated advertising methods, website designs, etc. As of five years ago I began paying taxes and doubled my income each year. To put things in perspective I am 100% financially independent, debt-free, and have enough savings to last me more than four years should I not work at all.

Now as you see with the right set of circumstances, hustle, and talent it is very possible to start a business with little funds. Because of these last 5 – 7 years of full-time work I am living the locationless lifestyle: working anywhere at anytime. Five years is a long time to get there. It’s not easy but it’s a pretty sweet way of living. What is the first step? Some may recommend a devry university college of business administration

degree. Certainly a formal education in business couldn’t hurt.

For more information about my businesses you can read some of the articles mentioned below.

Jason Bartoli

"Jason is the best person you'll ever meet here. He's just a ray of sunshine. An adventurer, businessman, and has a 4.9 Uber rating. Lovely person inside and out. I say, go message him" - My Mom

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