What I Learned Going From Creator to Founder (Part 2)
Continuing last week's discussion, I will share 5 more creator-founder lessons.
Persistence Isn’t Enough
Just because you don’t give up doesn’t mean you’ll succeed. This is where too much motivational content can actually hurt you.
A successful entrepreneur tells you to start companies. A YouTube coach tells you to keep posting videos. A stock picker tells you to buy single stocks. All are motivated to grow the addressable market by converting you into a believer of their path. Their intentions are good, because giving up is the only sure way to fail.
But they also know the math. Only a small percentage of their audience will ever make it. Outcomes follow power laws (more on that later in this piece). Most people won’t win, even if they try hard. If it were that easy, 95% of people would be founders, not working for others.
Entrepreneurship needs more than grit: you have to use your brain.
Maybe the market just doesn't need what you are selling. Or there are too few customers. When that happens, you don’t “push harder.” You pivot by trying something else. Plenty of successful startups pivoted before they found product-market fit. What you don’t hear about are the ones that kept pivoting and still failed. That’s the brutal part of going from zero to one.
In my case, the market is small and still is: public equity investing is flat to declining. But it’s also secretive, opaque, and wildly fragmented. That opacity gave me an opening to share an insider view. The fragmentation gave me a chance to aggregate job leads and profile employers.
Looking back, starting with 1-on-1 coaching, something that doesn't scale, was fine. However, monetizing right away was the mistake. I sat at my desk every day with no one signing up. I kept posting content, basically shouting into the void: “Pay me to talk to you 1-on-1.” It didn’t work.
Coming from public equities helped in one important way: I was used to actively looking for guidance. I read blogs and watched YouTube videos. Through an old connection, I joined a small founder network. The network fizzled out—but one conversation mattered.
A guy named ZZ was surveying people for something he was launching. I agreed to help. In return, he listened to my business problems. His advice was simple: stop charging. Offer two weeks of free calls. Just listen (to your customers.)
Those two weeks made big progress. My calendar filled up from 8am to 5pm. I learned one big insight: customers have problems, but they don’t know what unless you name them clearly. I started seeing patterns—pitch support, financial modeling, competitive analysis, and more. Once I reflected those problems in my positioning, conversions improved. That clarity snowballed.
Still, coaching itself was never going to be the end product. So I kept exploring.
I spent a lot of time on a finance forum where undergrads asked questions. That’s where I first built an audience. It was also how I followed industry trends after leaving the job myself. In hindsight, the answer was obvious.
During MBA recruiting, I knew research firms don’t post jobs, but I also knew firms do – it’s just they are in 500+ places. Aggregating and filtering job leads was real value. But I didn’t see it at first, because of bias: I thought a “career coach” is supposed to sell coaching.
So I started testing. I posted new job openings using the same workflow I used during MBA recruiting and shared them daily in my newsletter. Subscriber growth picked up immediately.
My friend Justin pushed me to turn the job board into a paid product. The timing was perfect. ChatGPT had just launched. I used ChatGPT to vibe-code a job board using HTML and JavaScript.
Money started coming from happy first adopters. I continued to market it daily on my social media. That was product-market fit—and how I went full-time as a creator by building a subscription business.
The whole journey was messy. Lots of zig-zags. No single right answer. Just a few key moments that moved everything forward.
Persistence helps. But you have to think, learn, and act at the same time.
Power Law and Critical Mass
I like philosophy. Not for fun—this is just how I learn. Two concepts are relevant in business and the creator economy: power law and critical mass.
Power law is the idea that a tiny number of inputs drive most of the outcomes. Looking back, really only 2-3 decisions each year pushed my business forward in a meaningful way.
- Launching the job board was the decision that moved me from an unemployed content creator to a self-employed founder with real income and growing leverage.
- Ten pieces of viral content are responsible for more than 90% of my new followers in a year.
- About 5% of my audience are paying customers that put meals on my table. The rest? I am renting their attention. As long as I serve the 5% well, I will grow my business – power law.
- Ask a hedge fund founder what drives their P&L and they’ll usually say three to five positions explain most of their performance in a year.
Power law shows up everywhere in life.
The second idea is critical mass.
I always use boiling water as an example. You can turn the heat up and nothing happens for a long time. Then suddenly, it boils. After that, you can turn the heat off and it’ll keep bubbling for a moment.
That’s critical mass (also called a boiling point or escape velocity.) It’s what happens when a business finds product-market fit. It’s what happens when a creator finds content-audience fit. When it works, it grows exponentially.
Last year, a few viral moments on Twitter led to a Bloomberg report's attention. A Bloomberg article last January brought me six months’ worth of paid subscribers in a single day.
What people didn’t see was years of work with almost no progress. That’s critical mass: one visible event that’s really the result of a long buildup.
My creator journey followed the same pattern. The beginning was brutal. When you have zero followers, getting views is hard. I kept posting anyway, because every post gets shown to strangers. Eventually, a big account noticed my work and reposted it to tens of thousands of followers. Then equity research associates started following me. They reposted my old content. Suddenly I had my own distribution and growth accelerated fast. When it rains, it pours.
Media loves to frame success as an event. It never is. Some of the most successful companies made no money for years before things clicked. For example, Dylan Field's Figma generated no revenue for four years. Those four years are not wasted, they led to the product-market fit.
Power law explain why only a few decisions matter. Critical mass explains the importance of unseen compounded effort.
Learn to Sell
Creators who started businesses don’t start from zero. We have the distribution but no product. You’d think once you find product-market fit, money just starts rolling in.
Not quite.
There are a few hard truths to remember.
First, being a little famous doesn’t mean people want to pay for something you’ve (or others have) been giving away for free.
Second, exchanging money for value is sacred. Customers are right to be skeptical. They want to know if your product solves their problem, because they have limited money to allocate to things that add value to them. Third—and you only learn this by doing—buying decisions are often emotional, not rational.
That’s why you need to learn how to sell.
Selling is about appealing to the emotional side of the brain. This isn’t manipulation. If people don’t believe your product has value, they won’t use it—and you cannot help them. Selling well lets you make impact and earn money.
The good news is tips on how to sell is everywhere. Read classic copywriting books. Study how great products explain themselves. Then apply what you learn to your product pages.
Incentivize users to leave reviews. Show those reviews publicly. Social proof lowers fear and brings in early adopters.
From there, the flywheel starts. People get value - they land jobs from my products and then tell others. Success stories bring their classmates and colleagues. Business grows and my impact grows.
Learning to sell isn’t just important for entrepreneurship—it’s a life skill. You’re selling every day whether you realize it or not: dating, promotions, influencing corporate decisions, and so on.
As long as you deal with other humans, selling matters. As a founder, it’s not optional. Today, I spend less time building new products and more time marketing and distributing the ones that already work—because revenue grows when selling gets better.
Learn From Others
One advantage of coming from the buy-side is learning to be proactive. Most of the time, I still don’t know exactly what I’m doing. I’m just less scared now.
That’s because I know two things. First, I’m allowed to be wrong and fix it. What I build isn’t mission-critical. No one dies if I mess up. This isn’t a heart pump or a car. Second, I know who to learn from. I can study people by consuming their free or paid content. Alex Hormozi, Dan Martell, Justin Welsh, and many more.
If you’re the kind of person who waits for instructions, entrepreneurship probably isn’t for you. Early on, you have to do everything yourself. Literally everything. You can’t afford to outsource. And even if you could, outsourcing before you understand the details creates a fragile business. The moment something breaks, you lose customer trust—and you won’t even know why, because you weren’t involved from the start.
In both my creator and founder journey, I learned by watching others. I studied creators like Vanessa Lau, Ali Abdaal, Think Media, Matt McGarry (the newsletter guy), and I also learned from the year-end reviews of other financial creators.
The information is out there, but remember: every business and creator is different. For example, just because my job board works doesn’t mean someone serving the AI industry can sell one. AI jobs are everywhere. You can find them easily on LinkedIn. The same goes for investment banking. Off-cycle roles are rare, and on-cycle recruiting is so structured that a job board isn’t needed. Paying for job boards doesn’t make sense if you are recruiting for AI or IB.
Learn from others, but don’t copy blindly. What works is deeply tied to the niche, the timing, and the problem you’re solving. You can borrow ideas. You can’t borrow context.
Buying Back Time
One of the biggest growth unlocks for me as a founder was understanding the power of buying back time.
At one point, I was overwhelmed by hundreds of small tasks every day. None of them were particularly hard, but together they were exhausting. Worse, they didn’t make me better at my actual edge: understanding the public-equity investing ecosystem and communicating it clearly.
On a call with a buy-side analyst who was also running a successful faceless educational YouTube channel, I complained about how draining this felt. His response was simple: read Buy Back Your Time by Dan Martell. That book reframed how I thought about work, delegation, and leverage.
The core idea is straightforward. Your time should be spent on the activities that actually compound—strategy, relationships, and high-leverage creation. Everything else should be systemized and delegated.
Once something works, you document it. You write down the process step by step. That process becomes the manual you hand off to someone else so you can remove yourself from execution without breaking the system.
Today, I work with contractors who handle social-media automation and data gathering. I record short instruction videos, maintain clear workflows, and let a virtual assistant execute the daily tasks. This has freed me to focus on building relationships for the job marketplace and creating exclusive content for paying subscribers.
If you think about it like an investor, the math is obvious. Paying $500 a month to outsource work that leads to $4,000 in incremental revenue is not an expense—it’s a return-generating investment.
The lesson is simple: be willing to spend money to outsource low-value work. That’s how you buy back time. And buying back time is how you build something that can grow beyond you.
Conclusion
To recap, blind persistence won’t get you anywhere if you don’t use your brain.
Products don’t sell themselves—you have to learn how to communicate value and earn trust. The good news is you can learn how to execute as a founder by studying others, and today most of that knowledge is free.
When things finally work, they tend to work in a big way. A small number of decisions will matter far more than everything else you do.
Finally, understand leverage. Past certain point, you can’t grow by doing everything yourself. It comes from delegating to others to amplify your effort—through labor, capital, and distribution.
Learn to buy back time, build systems, and let leverage compound.
Thanks for reading. I will talk to you next time.
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