For many years when people asked me how many businesses I have been a part of, I would say something non-commital like “Oh, a few.” Some people may have thought I was being humble, or on the flip side that it was not many and I did not want to say an exact number.
The truth is actually a lot simpler. I didn’t know!
I hadn’t ever bothered to sit down and count.
So what inspired me to change? It was making this website. By making this website I am committing to share my journey and experience with anybody who wants to go on their own quest and find their own hero’s journey.
For those of you who are not familiar with Donald Millers’ amazing book Building A Story Brand, let me give you the key point I took away.
If you are sharing information, selling a product, or trying to grow something you can’t be the hero of the story. You are the guide. The Gandolf the Grey, the Dumbledor, the Professor X.
In order to be the guide, you need the experience, and more importantly, you need people to believe you have the experience.
This list is to help with that. Here is a list of all the profitable companies I have been part of since 2008. It also has a few of the failures I remember, and a few that may have been successes or failures depending on your point of view.
| Business Name | ARR | Description |
| Live Lingua | 7+ Figure USD | One of the top 5 online language schools in the world. Only one with no external investors. [Sold to then sued to get back due to non-payment] |
| College Admission Secrets | 7+ Figure USD | Minority owner of a 7 figure college admissions company. Joined at 300k and helped scale 1.5 million within 7 months of joining. |
| RCB Coaching | 6-Figure USD | My personal coaching business. I grew it to 13k in income in 2 weeks. Only take 5 clients at a time. |
| Podcast Hawk | 6-Figures USD | SAAS company to get you booked as a guest on podcasts. |
| M3 | 6-Figures USD | Entrepreneur community. Minority owner. Grew gross revenue by 200% within 9 months of joining the team |
| QLS | 6-Figures USD | My first ever business. Bootstrapped language school with only 2.5k to 6 figures ARR within 24 months. [Sold in 2012] |
| SCLS | 6-Figures USD | Launched a second school and got it to 6 figures ARR within 6 months. [Sold to partner] |
| Ginto Chocolates | 6-Figures USD | One of the top Belgium chocolate producers in the Philippines. [Sold to partner] |
| Infinite Upcycle | 6-Figures USD | Content amplification agency. Got up to 20k of MRR in 3 months. [Sold to partner] |
| Rayvensoft SEO | 6-Figures USD | SEO agency. Got up to 20k MRR within 6 months. [Winded down] |
| Spanish-Lessons-Online.com | 6-Figures USD | First version of Live Lingua. Got to multiple 6 figures, then got killed by a Google algorithm update. Rebuilt as Live Lingua. |
| Online-English-Lessons.net | 6-Figures USD | First version of Live Lingua. Got to multiple 6 figures, then got killed by a Google algorithm update. Rebuilt as Live Lingua. |
| German-Lessons-Online.com | 6-Figures USD | First version of Live Lingua. Got to multiple 6 figures, then got killed by a Google algorithm update. Rebuilt as Live Lingua. |
| Online-French-Lessons.com | 6-Figures USD | First version of Live Lingua. Got to multiple 6 figures, then got killed by a Google algorithm update. Rebuilt as Live Lingua. |
| Zen Tasks | 5-Figures USD | Transcription agency in the Philippines. Got to about 2k in monthly income in a year. Closed it down. Work not worth the money |
| Cooking Classes in Mexico | 5-Figures USD | Cooking classes in Mexico by my wife. Got to about 4k a month in income. Now on pause due to having a child. |
| HowMuchToiletPaper | 4-Figures USD | Purchased domain. Monetized the domain with ads. About $400 a month. Will do more with this later. |
| Onmatu | 4-Figures USD | Tutor directory for math tutors. Got to to just over $700 a month, then lost interest |
| Onmutu | 4-Figures USD | Tutor directory for music tutors. Got to to just over $500 a month, then lost interest |
| TeachMeMexico | 4-Figures USD | Travel agency for Spanish schools in Mexico. Still get occasional clients. At peak got about $2000 in sales high season. |
| Spanish2Go.net | 4-Figures USD | Arranged private in-person Tutoring in Cancun, Playa del Carmen, and Tulum, Mexico. |
But let me make it clear, not everything I tried was a success. Far from it. I have had many more failures than successes. The beauty of being a bootstrapper though is that the loss in most is not very large on the monetary end.
You do of course lose time, but if you do it right, you also grow and learn from it. So hardly a total loss.
Here are just some of the “not-successes” that I remember. I don’t call them failures. Failure would be if I had not learned anything from it.
| Business | Description |
| Peshas | Personal shoppers online. Realized I hate managing people who shop. |
| OnDuMa | Online Dungeon Masters site. Never got traction |
| BacklinkHippo | SEO Saas product. Could not find product market fit, though I still use it. |
| ExpatVA | Virtual Assistant services with expats as the workers. Could not find ICP. |
| TeacherIndie | A website to teach teachers how to launch a business online. |
| Anomalous Educator | A podcast to work with teachers to help launch businesses online |
| Negocio Dojo | Teaching online business in Latin America. |
| Online SAT Tutor | Tutoring for SAT. Did not have the time to market. |
| Online GMAT Tutors | Tutoring for GMAT. Did not have time. |
| Shower Head Empire | Tried to launch a dropshipping store for shower heads. Did not work. |
Then there are the unknowns. Businesses that I launched that actually had traction but did not make money… yet. I still have them and want to get back to them one day.
| Business | Description |
| LearningStyleQuiz.com | Over 500k people have taken the quiz. I have about 50k+ emails. Not monetized yet. |
| Twiducate.com | Purchased. Social network for schools. Grew by 120k users. Not monetized yet. |