How taking a side hustle full-time led to financial freedom for this entrepreneur

Posted: 11 April 2022 10:41 am
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Alex Goldberg shows that stepping back in your career can ultimately lead to a far more lucrative one.

Our series highlights stories from real people who’ve joined the financial independence, retire early (FIRE) movement. Some have successfully reached FIRE, while others are on track to do so over the next few years. Answers are edited for length and clarity.

  • Name: Alex Goldberg
  • Current age: 30
  • Profession: Growth Marketer turned online media entrepreneur
  • Investment strategy: Invest early. Invest often. And most importantly, invest your free time to create new income streams.

How did you get your start with FIRE?

Financial freedom has always been my goal. Right away after college, I joined early-stage startups with the hopes of learning how to build my own business from founders. These early entrepreneurial environments forced me to wear many hats and helped me develop scrappy marketing skills.

But I soon realized that I’d never get rich working for someone else. So I committed to side hustling in my free time — not only for extra income but also as a way to validate startup ideas. I spun up many schemes, some profitable, many not. A few examples include:

  • House hacking. Staying at my girlfriend’s apartment on weekends to rent out my flat in San Francisco on Airbnb. (No, this was not permitted under my lease, but my landlord didn’t catch on for over two years. I even managed to achieve SuperHost status.)
  • Moonlighting as a freelancer. Today, consulting on the side is more likely the norm than the exception. But back in 2014, this was rather enterprising.
  • Starting a local service to help the elderly use basic technology. For example, using an iPad, printing their favorite poem and accessing email.
  • Investing in alternative assets. I’m by no means a savant, but I do enjoy being in the market. In addition to stocks and bonds, I’ve invested in a wide range of alternative asset classes including fractionalized shares in fine art, crypto, peer-to-peer lending, friends’ startups and physical and digital real estate. Nothing has netted me a 10x return, but I’ve learned that you’re better off investing than staying on the sidelines.
  • Building websites. My first attempt to make money online was an affiliate site called I amassed a small graveyard of similar projects before eventually getting one to take off: Fin vs Fin. My business partner and I then doubled down, creating additional product review sites like Zenmaster Wellness before purchasing others in new niches like Fitness Masterly and Pupfection. We managed this portfolio of sites while maintaining our steady day jobs. Eventually, things grew to a level where it no longer made sense to keep my 9 to 5. Today, I’m fortunate enough to focus on my own businesses full-time.

What sets you apart from others involved in this movement?

I differ from typical FIRE enthusiasts in that I don’t ever dream about retiring early. In fact, I don’t ever plan to fully stop working unless, of course, “retirement” just means a lack of corporate employment. That much I’ve managed to achieve by age 30, but the plan isn’t to slow down and hang out on a beach any time soon. Just the opposite. Now’s the time to build up my empire even more — but at my own pace and on my terms.

I enjoy building, being analytical and using my creativity — I just don’t want to do that for someone else’s business anymore. For me, being able to work how, when and where I want is true financial freedom, not the lack of work entirely.

What advice would you give those thinking of pursuing FIRE?

Find a job that allows you to tinker on the side. Truthfully, that might mean taking a step “back” in your 9-to-5 career, responsibility-wise. This worked well for me, as working in the earliest-stage startups was all-consuming, but joining a slightly larger company (>1000 employees) allowed me to fully shut my work laptop at 5 p.m. sharp. However, I only recommend this step back if you can fully commit to using your free time side hustling or tinkering with business ideas.

For anyone interested in FIRE, the first suggestion is to de-emphasize penny-pinching and instead refocus on earning. After all, you can only save so much, but your potential to earn is limitless. Once you fully recognize that you’ll never achieve financial freedom with a single income stream, the natural next step is to dedicate yourself to developing new ones.

While it may be unclear how to invest your time profitably, one piece of advice almost certainly guarantees side income, and that is: create more content than you consume. In other words, binge-watching Netflix almost certainly yields you $0, but making a short movie, publishing a review of your favorite show, creating art for other fans or building an online community all have the potential to help you quit your day job.

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