Hey Team,
It's been a year since I quit my big corporate job to become an entrepreneur.
This is a good time for me to reflect on how I think entrepreneurship is changing. When I first quit my job, I thought the only path to success as an entrepreneur, for someone like me, was through building software—then going after VC dollars.
And for the first few months, from September until January, I pursued only that path. But then I learned, the hard way, that SaaS is a slow grind.
If things continued for another nine months the way they started the first three months, I would've had to pack it all in. The dance would be over. I planned to try this entrepreneurial thing for 12 months; if nothing changed in income in 12 months, I needed to look for a job again.
Three months into the journey, I got the existential chills.
I feared that my entrepreneurial attempt might end prematurely and that I had given up a million-dollar-a-year salary and would have nothing to show for it.
And worse than that, I thought about how long someone like me had to work in the first place to get to this position. After all, 15 years prior, I earned maybe $20k a year working in a restaurant. It wasn't easy to find the courage to quit nearly a million-dollar-a-year salary in the first place. And the higher the salary the harder it is to get paid less or quit it.
I knew I had to try more things; I didn't want to fail as an entrepreneur.
But then, in December of last year, I ran into the Small Bets community through Twitter. There, I found people wanting to make a living in very different ways. Some in Small Bets were consultants; some had small software projects, some sold books, and some sold courses. Some were building audiences. All of it was foreign to me.
And the best people in Small Bets tried it all; they were modern-day Michelangelos.
That community has a course attached to it where everyone is asked to take inventory of everything they know; Daniel Vassallo, the founder, calls this an "Asset Stack." Then people are encouraged to use only the things they already know to make money.
In fast-to-success experiments, people are told to dedicate a few weeks or a month at most to a "Small Bet." And try and produce something that can make money from that experiment. Another requirement is that the experiment is cheap and has no chance of wiping one out. But a cheap experiment also means one has to curb their ambition about the expected payoff. And another requirement is that one should try as hard as possible to get at least a small win.
The fundamental premise is that we can work with a win. We can massage a win and do things to make it a more significant success later.
But a loss is a loss; we can do nothing with it except use it for scraps on the next project.
And I bought into all of this. My engineering brain connected the dots and believed this all made a lot of sense.
I placed my first bet starting at the end of January, and to my shock and surprise, it worked. I made my first few dollars on the internet.
Not only that but right around the same time, thanks to writing lessons from another internet course I had taken called Write of Passage, I started building an audience from all of this. I began to attract people that I could help and that could help me.
Placing bets and writing about them all fed into each other.
Placing small bets, and getting a small win, meant I learned something. Then I made sure to write about it well and share the lessons. Doing that, along with sharing everything else I knew, led to people wanting to follow my journey. (Most of my people subscribed to this newsletter, and I thank you!) Some only follow me on social channels, and that’s ok because if they learned something, I helped in some way; they were more likely to help me when I needed it.
And I need help every time I am about to place a new bet. I needed feedback on it or help to amplify it, and I am grateful for how people have continually helped me.
These are all things I knew little about before going down this path. All stuff I fully internalized this last year.
Don't get me wrong; I had read that people could publish things on the internet and have access to similar tools as the NY Times. I had heard that people have ways to do paywalls and ways to write, edit and distribute content that can rival the best prominent publications.
But it's entirely different to do it yourself and see it firsthand. Especially as an engineer that knew little about this world.
In fact, so many tools are available to the individual now that one can make almost anything. Self-publishing a book is a breeze, making and selling a course is even easier. And it's not limited to just media; one could even rival a small piece of the tech giants like Google and Amazon with a combination of no-code tools, payment systems, and off-the-shelf platforms. As an engineer, and engineering manager, I know it took teams with numerous engineers to do these things before, but that's not the case anymore.
I stumbled onto all of these things partly out of this existential fear of failure three months into my entrepreneurial journey.
And so far, I've made around $80k from this internet game. That money is from courses, software, and consulting. But all of it came directly from small bets, my writing, and this internet game. Even though I am not a huge goals person, earlier this year, I set a goal of hitting $100k in "internet money." I am pretty confident I will hit my goal. And once I do, I will break down all the income streams as I did mid-year.
But the more important thing is if someone like me, an awkward and introverted engineer, can go out:
make a few dollars
build a small audience
command some attention
extend my entrepreneurial runway by at least a year; then, others should probably be able to do this, too, and much more.
And what I know firsthand from this last year is that these things build on top of each other. Things compound. And what I’ve seen secondhand is that some lucky individuals a few years ahead of me are making millions doing business just as individuals. So I am optimistic about trying a lot more things next year too.
Entrepreneurship is evolving before our eyes, but everyone seems so focused on the next big thing.
My unique perspective is that while everyone waits for Blockchain or AI to disrupt everything, they are missing all of the small things that are reshaping the entire business world.
Two Tweets from this Week:
A great thread by Warren on how so many teams grow to ignore the existential risk with their projects.
Something so serious that usually stares a product team in the face that they believe they will simply overcome.
The lesson is if we are feeling existential risk, don’t ignore it. Take action, pivot.
A fun, light hearted, story by Jon about embarrassment in his childhood.
If you do decide to read it, I want you to pay attention to how well written it is.
One Meme from this week:
A fun meme that many of my engineer friends will relate to. My friend Alvin wrote a nice piece about solo devs vs. devs working on a team. The piece very much relates to this meme. I recommend a read if you are in software development.
A small update from me:
Every time I present in front of strangers, my heart rate shoots up so much that you would think I was at the gym.
This is my third time mentoring for Write of Passage. Every time, without fail, I meet incredible people.
And every time the course runs, every six months, I am invigorated with new ideas from conversations I have with people from all over the world and from so many fields.
And it is a lot of work to prepare for these sessions to teach people every Sunday. But it is incredibly rewarding too.
Meeting people who want to become better writers, use their writing to get ahead, and become better at this internet thing is very rewarding.
But watching my heart rate go down week over a week because I am getting better at teaching and presenting in front of strangers is also rewarding.
And all of these things, like better writing and better presenting only come from putting the reps in and improving.
Thank you for reading the 76th edition of this newsletter.
-Louie
P.S. you can reply directly to this email it will get to me and I will read it.
Love this post Louie!!! Also the term "internet money." I might have to borrow that one day.
I really like the thread by Warren thanks for highlighting it