Last Wednesday marked six months since I posted my first reel.
In that time, I’ve made $36,180 as a creator.
Depending on your frame of reference, that might sound like a lot. But in the spirit of transparency that I started this entire journey with, I’ll be honest: for an audience of over 300,000 people, it’s lower than you would think.
This journey has been a real-time MBA in monetization, and today I want to share the most valuable lessons I’ve learned. Lessons that I believe are key for anyone looking to build a life of freedom and sovereignty online.
Now, let’s break down how I got here.
My Messy Path to $36,180
First, the breakdown. This isn’t a straight line of success; it’s a winding path of exploration.
April: Started posting. Made $500+ from pre-sales for the Job Offer System in under three weeks. I then refunded it all and turned it into a free resource because selling it felt misaligned with my story at the time.
May: $2,000 from the SWE Offer Vault.
June: $800 from the SWE Offer Vault.
July: $11,700 from a high-ticket group coaching program on personal branding and $7,500 from pre-sales of the Viral Playbook.
August: Signed a $15,500 brand deal, which came to $12,400 after the agency’s 20% cut.
September: $1,200 from the Viral Playbook early bird.
Miscellaneous: ~$580 from affiliates, YouTube AdSense, and TikTok.
Grand Total: $36,180
The brand deal was the single biggest check, and it’s what most people imagine when they think of “making it” as a creator. But to be frank, I never wanted brand deals to be my primary income source.
Not because I’m a saint who’s above promoting things or above money, but because there’s a lot more that goes on behind the scenes than meets the eye: negotiations, contracts, script reviews, etc.
Most of all, for 95% of brands, I just wouldn’t feel right about doing them.
You may see it as woo-woo, but to me promoting brands I don’t genuinely believe in incurs a sort of spiritual debt. And while there is a practical, financial component to all of this, I didn’t quit Google just to find the fastest path to money. I quit in search of work that I don’t have to retire from.
The Six-Month Search for Energy
This brings me to the question you're probably asking: 'Jim, if you think you're so smart, why aren't you making more money?'
Here’s the uncomfortable truth: after July when I essentially made a $20k month, I knew exactly how to make money. Scale the coaching program. Run paid cohorts. Take brand deals. I’m not saying it would be easy. But it would be straightforward.
I even felt obligated to. People got results and showed me love.
But here’s what kept eating me up inside for weeks: I didn’t want to.
Every time I mapped out the path through these models, my body would tense up. More calendar obligations. More community management. More of the safe, but misaligned path that I had at Google.
After endless mental battles in my head, I decided I had to look at the evidence. And not just at the revenue. I charted out the activities I was doing/had done in the past and measured my energy and revenue:

The money spoke clearly in favor in one direction. But the energy spoke in the other. My energy and fulfillment are highest when I'm building a valuable, scalable asset (like an indie SaaS) and when I'm sharing my most authentic insights through writing. The very things I wrote in my journal that I wanted to do before I even quit Google.
You can only go straight to your destination if you know where you’re going. A lot of the time you can see the mountaintop but you can’t see the trail. Wandering may feel very inefficient, but it’s actually very valuable.
Of course, even now, the practical path tempts me. I think about how I’m an idiot to not listen to the market. People DM me for mentoring and coaching regularly.
But as someone who had followed the practical route for twenty-seven years, I want to honor the bet I took when I quit my job and follow my energy.
The Skill That Kept Me Safe
The asset that has kept opportunities open through all my wandering has been my audience.
Now I never would have expected to become someone who posted on social media, so let me quickly explain how I got here in the first place.
Before I started creating content, I built an AI dating profile analyzer called SwipeIQ. For weeks I coded it. Day in and day out.
And finally when it came time for launch?
Crickets.
I had committed the cardinal sin: I built a product without distribution.
I was DM’ing people on Reddit, begging them to try it for free. I got banned from subreddits for self-promotion.
Let me tell you that there’s not many feelings more humiliating than asking power-tripping reddit moderators for a ban lift.
Feeling furious yet utterly defeated, I vowed that I would do everything in my power to avoid being in this position ever again.
One week later, I started posting content... And within two weeks of posting, I had 100 free users and even my first accidental paying customer.
That's when I realized: Building an audience is the opportunity of this decade.
When I look back at my journey now, my audience is the asset that enabled me to wander and still come out ahead.
And it’s not just for me. Other creators like Ali Abdaal successfully pivoted from med school exams to productivity to YouTube education thanks to the audience he’d built. George Miller’s Filthy Frank audience is what allowed him to evolve into Joji.
So in a strange way, I’m thankful to those reddit moderators. For spurring that fire in me to develop the skill of creating organic content.
Because five years from now, who knows what I’ll be doing? Maybe I want to fulfill a dream of writing a book. Maybe I want to be a zookeeper or open a restaurant. Even if my audience doesn’t carry over, I’m pretty sure I can figure it out. Because I developed the skill of building one.
That’s the real safety net.
The Path I’d Take If I Had to Start From Zero
After six months of messy exploration, I came up with a fun exercise: if I had to speedrun my first $1,000 online as a creator, how would I do it? Zero capital to invest, no viral moment of quitting Google, and no content or product/service skills.
Based on my own mistakes and insights over these months, this is what I came up with:
Step 0: Start with Your Energy. Before writing a single post, I’d do the Whiteboard Exercise. The biggest takeaway from my six months of experimentation is that nothing else matters if the work drains your soul. A company lives and dies by the founder. An audience lives and dies by the creator. Figure out what kind of work genuinely energizes you.
Step 1: Build the Distribution Engine. I’d focus 100% of my first weeks on creating content and building a small, engaged audience around my story and/or my niche. I would not code an app or design a course until I learned how to get distribution. My failed SaaS taught me this the hard way. To do this, I’d copy and adapt content that is already proven to work.
Step 2: Validate with a Wallet. Once I had some attention (1,000 followers is enough), I would start testing my best idea from Step 0. I would pre-sell it or create a waitlist with a small deposit. I would do whatever it takes to get someone to pull out their credit card before I invest months building something.
*Underprice and give a money-back guarantee to build confidence to overcome the psychology of selling something for the first time.
Step 3: Build the Winner and Scale. With a validated offer that aligns with my energy, I would then build it and fulfill the order. Run a simple launch sequence once complete. All while continuing to build my distribution engine in the background.
And that’s really it.
I genuinely believe anyone can make their first $1,000 in just a few weeks by following this process. To give you an idea of what it might look like:
5 1:1 calls at $200
20 pre-sales of a product at $50.
1-2 brand deals as a small creator
1 viral UGC video
With the skill of distribution along with the audience you have built, you can repeat the process over and over until you decide on the business model that aligns profit with your energy.
Of course, the hardest part of all this isn’t even the tactics or strategy. It’s the courage to actually start. I took longer to work up the courage to post my first video than I took to build my audience and revenue.
If you’re worried that people watching will expect you to have it all figured out, just look at me. I’ve switched business models every month. But I’m still alive and kicking. My audience doesn’t hate me (I think).
Take messy action. Build your distribution engine. Test your offers. Wander. See what lights you up. The uncertain path is the path.
See you next week,
Jim
P.S. The first and most important step to any independent income is building your distribution engine. I’ve packaged everything I learned about going from 0 to 300k followers into The Viral Playbook. It’s a complete system for getting your first viral piece of content. Check it out here.
