Eric SiuFounder & CEO, Leveling Up

Most people kind of know what to do on paper. They know they should reach out, ship, launch, hire. The real blocker is fear of the unknown. That feeling of “what if this doesn’t work?” I try to get used to doing things that scare me a little, so my default becomes action instead of hesitation.

I was literally doing data entry and felt like my life was going nowhere. A friend told me to check out internet marketing, so I picked up an internship. From there I got a marketing job, and about a year later I was suddenly leading marketing at an online education startup. It was messy, but it pulled me into the game.

At that startup I basically bet the entire company on YouTube ads. It was aggressive, but the numbers made sense and we went all in. That experience taught me that focused, calculated risk can change the trajectory of a business. You cannot tiptoe your way to big outcomes. You have to pick a lane and commit.

At first I thought, “Why would I do that? Agencies are not scalable, valuations are not great.” But then I reframed it. If I could turn around a failing SEO agency, it would be like a real-world MBA. It was a test for myself. That challenge felt more interesting than just staying comfortable in a tech job.

When I took over the agency that became Leveling Up, I was 27 and had no idea how to run a company. I made it go from bad to worse. It got so bad our accounting firm told me it might be time to shut it down. I even accepted another job and started looking at apartments. That low point forced me to decide if I really wanted entrepreneurship.

The big shift was our SEO starting to kick in. We ranked number one in the U.S. for “digital marketing agency” for a couple of years. We had huge brands like Uber and Amazon reaching out. Because we were down to basically one employee, we referred a lot of work to other agencies and collected commissions. That cash flow gave Leveling Up the runway to hire and slowly rebuild.

A marketing agency is a great starter business. Your capital expenses are low, you can start from a laptop, and it’s a cash flow business from day one. You do not need to raise money and burn for years. You get paid to learn, and if you build real scale like we did with Leveling Up, bigger holding companies might even buy you for a solid multiple later.

Pick one thing and get very good at it. That might be clipping podcasts into shorts, running YouTube ads, web design, or conversion copywriting. The more specific the better. When you solve a clear problem for a clear customer, like turning long podcasts into daily TikToks, it’s much easier to charge real money and build a Leveling Up–style service business.

Most people undercharge. They think in $3 products instead of $2,000 retainers. I like to think in terms of value and client outcome. If you can reliably create content, get leads or grow revenue, charging $1,500–$2,000 a month is very reasonable. Ten of those clients can already put you into multiple six-figures a year without a huge team.

I look at burn and margin. If you are making, say, $10K a month and your personal burn is low, you have room. Start by listing your $10 tasks, $100 tasks and $1,000 tasks. Anything that is low leverage and repeatable should be delegated first, often to an assistant, so you can spend more time on sales and delivery.

For a long time I was basically a well-paid consultant. I was on calls all the time, deep in delivery, constantly stretched. Being a real business owner means building a team, letting go of doing everything yourself, and designing systems so Leveling Up can function without you on every call. That shift is hard emotionally, but it’s where real scale happens.

I had a phase where I was spinning up everything: SaaS ideas, content projects, different businesses on top of Leveling Up. It felt exciting but also frantic. When we acquired two agencies on top of that, it became obvious I was overextended. I realised you can do anything but not everything. Compounding one main vehicle like Leveling Up for ten plus years beats restarting five things every year.

I say I have high risk tolerance, but I am not reckless. I never bet the house. I like the idea of one-way versus two-way doors from Amazon. Most decisions at Leveling Up are reversible, so you can move fast. I am happy to break a few eggs as long as I still have plenty of eggs in the bank if something fails.

The happy ones actually enjoy the game. They like solving people problems, product problems, sales, macro shifts. They treat business like an endless puzzle that keeps their mind sharp. Money is an outcome, but they would keep playing even if they did not need more. When the game itself feels good, you do not feel as empty when you win.

I try to treat health like a core part of the job. I lift four or five times a week, do zone two cardio, watch my sleep, use tools like an Eight Sleep and an Oura ring. When I feel better, I make better decisions for Leveling Up, I am less reactive, and I can show up stronger for my team and partners.

Logistics drain my energy. Scheduling, travel, invoices, sponsorship admin – all of that steals focus from the high-leverage stuff. An EA handles the details. A chief of staff can jump into bigger projects like sponsorships or deals around Leveling Up. Buying back that time lets me spend more hours on strategy, content, relationships, and the few decisions only I can make.

Pick one skill that solves a real problem, like editing shorts, writing newsletters, or running YouTube ads. Get good enough to charge real money. Then reach out to people a level or two below the biggest names, show them actual work you have done, and ask for a small retainer. Do good work, ask for introductions, and repeat. That is how you get from zero to $10K a month.