In 2016, I was a bright eyed naive 26 year old. I would describe myself as the prototypical “entrepreneur-kid”; I was constantly trying out new and sometimes wacky business ideas.
The vast majority of them failed 😅, but a handful did well enough to keep the lights on.
I had given up on being “employable” a long time ago.
My only “jobs” up until this point:
8 month stint as an Associate at a Venture Capital firm (my role was affectionately referred to as a “deal monkey)
An even shorter stint as a Cashier at a Blockbuster in 2004 (I got fired).
Good times…
Like a lot of people, I managed to accumulate a wide ranging (smattering if you will) of skills and experiences.
I ran a successful web & mobile app agency for 5 years.
I raised investment as a startup founder AND negotiated startup term sheets as an investor (of other people’s money).
I ran a massively lucrative Airbnb in San Francisco.
….I even ran a taxi company at one point.
The problem I had was that all the things I had learned, experienced, and practiced… were unrelated to each other.
So I was stuck with a scenario that is well known to those bitten by the Entrepreneurship bug: I had no “next project” and there was no obvious “next thing” for me to do.
I had just passed off the reins of my modest digital agency to another team, and had sold off the last of my ill-fated Prius taxis (don’t get me started).
What do you do next?
Staring at a wide open field of opportunities can often feel overwhelming, instead of liberating. We call this the “paradox of choice”.
One who has too many options to choose from, struggles to choose. If you’ve ever told a waiter that you need “a couple more minutes” because you’ve ony just gotten to page 5 of their 16 page menu… you know what I’m talking about.
The solution to this conundrum was pretty clear: online courses.
Friends and not-so-friends had been coming to me for years for advice on different things: writing cold email campaigns, renting out their spare room on Airbnb, outsourcing web app ideas, buying used cars, traveling on budget, etc
The lightbulb moment where I finally connected “people value your advice & expertise” with “you could sell that advice online” happened on an indescript weekend in San Francisco.
On that weekend, my roommate announced to me that he was going to make an online course for a company called Udemy. I had never heard of this company.
He called it “OOO-DEMI” 🙄
(It’s pronounced “YOU-DEMI” by the way)
A man of his word, he preceded to spend 2 Saturday nights scripting and recording a course on “how to use SQL”… while very intoxicated.
He was drunk.
Way too drunk to make a coherent lecture.
I still remember hearing him stumbling (did I mention he was drunk?) through his loosely pieced together script into a cheap USB microphone, while using a bookcase in his bedroom as an impromptu standing desk.
His short, simple, unprepared, and remarkably successful course
The course was short, it was simple, it was unprepared, and it was… remarkably successful.
The first month it was live, he made $1,500without doing any promotion. The next month it made $2,500. 🤯
For the next 2 years, that course he filmed drunk between 11pm and 3am on two Saturdays made on average $1,500 a month, with no maintenance required.
This blew my mind and still does).
Now I realize this isn’t as noble of a genesis story as Symon’s. He made his first course so he could spend time with his ailing mother. I on the other hand, made my first course, because I felt I could do a better job sharing my knowledge than my drunk roommate.
Oh well.
My first online course
For my first course, I settled on a topic that was freshest in my mind and I had a feeling people might be interested in: Airbnb Hosting.
(It was like a podcast with extremely basic graphics I slapped together in Final Cut Pro X)
AirBNB was relatively new at the time, and people were just figuring out what potential it had.
I was living in San Francisco in a neighborhood called “Fisherman’s Wharf”, a famous (or notorious depending on your viewpoint) area that was known as THE spot for out of town tourists to conglomerate.
(side note: this is why in a lot of my courses I sarcastically refer to where I live as “the real San Francisco”. The more you know)
To deal with the ridiculous rent I owed every month, I decided to rent it out our living room (and occasionally the whole space) whenever we could.
Naturally, once I started doing this… I went all-in. I obsessively optimized every part of my Airbnb listing. I tested out new photos. I tested gave guests welcome gifts, and charted their average reviews vs what type of gift I gave them. I even rehearsed check-in scripts that I would repeat to each guest.
My neuroses paid off and I did well.
At one point in time, I was the #1 host in San Francisco out of 5,000 hosts (not to mention, SF was Airbnb’s headquarters). Our first summer, I convinced my roommate to let me rent out the space for a full 3 month period. As a result, we each got PAID $5,000 a month (after covering rent), to NOT live in our apartment. (I spent it in Bali).
It was undeniably ridiculous.
People were naturally reaching out to me for advice on how to get started, and I lost track of how many times I gave the exact same advice. This was a natural fit for an online course.
So that’s what I did.
Like all other wannabe online instructors at the time…. I had no idea what I was doing.
At the time, it seemed all the rage to make your course audio only and then just splice images over the screen to match what you were saying.
Since, I was clueless about what worked and what didn’t, I just copied what I saw. Monkey see, monkey do.
My initial equipment and setup
I spent $75 on my entire setup. First, I bought a 5 gallon plastic container from a hardware store. Next, I bought $20 worth of sound foam on Amazon. I glued (bad idea) the sound foam inside of the plastic container and voila, I now had a mobile sound recording studio.
The last thing I did was stick a $45 Blue Snowball microphone inside, and I was ready to roll.
Nevermind that the space was so small that it SOUNDED like I was talking in a box, or that the closed system allowed no air in the box when I recorded, or that well… sticking your head in a closed off box with fresh wood glue isn’t a great idea.
I was determined to make it.
I was also… a little high from the glue.
Nevertheless, I powered through it with no script and only a vague idea of what I wanted to cover.
When I published it, it was a monster 13 hours long. If you removed the “umms” and “you know”s from my recordings, I think it would have been half as long.
So how did my first course ended up doing?
The first month it was live it earned a grand total of…. (drumroll)…. $50.
It was fair to say the course wasn’t the overnight success I expected. Regardless, I decided to wait it out for another month (what else was I going to do?)
I’m glad I did. The next month it made $250. Not bad.
The next month, it made $400.
It capped out at about $1,600 a month from there on out, and continued to pay me on average $653 a month for the next 5 years (it’s still earning money).
In total, I spent about 50 hours over 2.5 weeks making that course, and it’s paid me to date $35,274 with no maintenance other than 10 minutes here or there answering a stray student question.
I didn’t have to do any marketing or any promotion. I woke up everyday and say that I made an extra $21 a day… for doing absolutely nothing.
While the monthly payment wasn’t blowing me away, the ROI for my time was pretty incredible.. and I had only scratched the surface of one topic I thought I could monetize.
Shortly after that, I decided I should go all-in on creating online courses, because why not?
I decided to give myself a set amount of time and a specific goal to hit. If I didn’t hit that goal, I’d go back to doing something else.
This is what I decided:
Time: 4 months Goal: $4,000 USD a month in earnings (my cost of living at the time.)
Unfortunately, I was pretty broke considering I had no income other than that first course.
Since, I was young and untethered (although my girlfriend at the time would disagree), I decided to spend those 4 months in a different country. A country with a lower cost of living where I could limit my monthly expenses and thereby not bankrupt myself in the process.
So I settled in a sleepy town in Thailand called Chiang Mai, and rented a house with an extra bedroom for filming videos.
CUE THE “rocky balboa” montage
The plan:
I worked 10 hours a day, day and night, scripted in the morning, practiced my videos in the afternoon, and brainstormed my content in the evenings.
I eat, breathed, and slept online courses. I wouldn’t stop until I hit the pinnacle of… I’m actually kidding.
I worked… on my courses about 15 hours a week.
The reality:
I mostly spent my time… enjoying my time. Only when the inspiration struck did I hunker down and start working on my videos.
With just 15 hours a week, I developed a system for writing my content and for filming my videos. Living in a foreign country did at time make things difficult, but I figured it out.
I installed a screen so mosquitos would stop flying across the frame while recording. I bought better looking “on-camera shirts” from a local company. When equipment would break, I would import replacements from neighboring China.
At the end of my 4 months, I had published a handful of new courses: “Idea Validation”, “Rapid Prototyping”, “Master Outsourcing”, and “Running a Web Development Business”.
By using some duplication strategies, I turned those 4 new courses into 7 new courses, and with that… I was at my goal.
The last month I was in Thailand I earned $4,043.11 and concluded it was time to return home.
MISSION ACCOMPLISHED
Fast forward to today, I have 36 courses and a pretty unbelievable passive income that pays me close to $1,000 a day every single day. I have close to 600,000 students in 170 countries.
I’ve spoken on podcasts, at conferences, and have translated my courses into 4 different languages. Over the last 4 years, I’ve traveled to 60 different countries with the freedom online courses have given me.
What my life is like today as an online instructor
I get recognized in airports.
I’ve met students all over the world (including staying with a student’s family in Mongolia).
All of this would never have happened, had I not stuck my foot out and tried my first course.
Unlike Symon, I decided to exclusively go the Udemy / passive income route. I didn’t want to spend time marketing my courses. I just wanted to create the content, share my knowledge, and continue to profit from it.
Over the years, my online course income has funded a string of different projects for me. I own land in Texas (don’t ask). I built my first robotic arm that I wear almost every day. I’ve started investing in startups. I support 15 different history teachers on Patreon. I own shares in a private island.
None of this would have been possible with my courses.
SixFigureInstructor is now my main project.
I want to help as many people get to where I am with online courses. I’m not the best teacher. I’m not the most polished presenter. I’m not some sort of productivity machine. I don’t have the most “experience”.
You don’t have to be perfect (or frankly even that good), but you DO have to start. Hopefully SFI can help get you there.
