Nick Loper’s career started out like many others: He got a corporate job right out of college. But he always had an entrepreneurial spirit that motivated him more than climbing the corporate ladder. He focused on building a side hustle that had the potential to earn him more than an employer’s paycheck. Once he did, he quit his day job and committed to making side hustling a full-time gig. We caught up with the founder of Side Hustle Nation this week and chatted about finding time for a side hustle, the downside of gig life and some tricks to doing self-employed taxes.
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This interview was lightly edited for style and clarity.
When did you realize you wanted your side hustle to be your career?
From the very beginning, I knew I had no desire to climb the corporate ladder. I wanted to be my own boss, but wasn’t sure how to make that a reality. Thankfully I had a little online project (a comparison shopping site for footwear) to occupy myself during nights and weekends, which eventually became my way out of that corporate gig.
The turning point for me was when that project started to make enough to cover my fixed expenses — rent, food, utilities, that sort of thing. At that point, I realized my entire day job paycheck was gravy, and it was a really empowering feeling. Still, I wanted to see a consistent track record of revenue before making the leap.
When I gave my notice at work, my side hustle wasn’t quite replacing my salary, but I saw how if I had another 40 to 50 hours a week to dedicate to it, it could definitely get there — and beyond.
What advice do you have for people who want to start a side hustle?
Give yourself permission to experiment. Test out the side hustle ideas that sound intriguing to you. Find out what you like and don’t like. As long as you keep your expenses low, positioning a side hustle as an experiment in your head gives you permission to fail and keeps the thrill of discovery alive.
Think of the problems you’ve overcome in your own life, what people already ask you for help with, or some of the pains or annoyances you encounter during a typical week. On the other side of those problems might be a business idea.
For example, in 2011 I started a directory and review platform for virtual assistant services. The pain point was I had struggled to find an assistant in my own business, and had a hard time figuring out which service providers were legit. Turns out, other business owners had the same struggle, and the site generated over $550,000 in total revenue (including proceeds from when I sold it in 2020).
How can people with 9-to-5 jobs find time for a side hustle?
The common advice here is to just wake up earlier, but there are a few steps to take even before you start looking for potential time in your day to work on a side hustle.
I’d recommend creating a clear vision of why you want to build a side hustle and what that might ultimately afford you. Then — since you probably don’t live in a vacuum — seek buy-in from the other stakeholders in your life and take stock in where your hours are currently going. You can use a tool like Toggl to track your time, or just do it Google Sheets, but I think you’ll be surprised that you probably have more time than you think.
Once you have those elements in place, then you can begin carving out time in your week to work on your side business. Write down your top 1-3 priorities for the next day the night before to avoid wasting time when it’s time to get to work.
Side hustles take work. What are the downsides people should be aware of?
The last thing you need is a second job you hate, so make sure you have a strong why to carry you through the challenging times.
There’s a certain backlash against “hustle culture” right now, the idea that you need to “rise and grind” or “hustle 24/7.” I’m all for controlling what you can control, namely your own effort, but spending every waking hour at work or sacrificing sleep isn’t a viable long-term strategy for your business, life or overall health.
The other thing to consider here is what does success look like? Look at the people two to three years ahead of you on the path you’re considering. Do they have freedom over their calendar? Are they still trading time for money? If so, how can you bake some [time] into your side hustle so that revenue can scale without your direct hourly input?
Perhaps the biggest hurdle is doing your own taxes. Do you have any tips for good record keeping?
Yes, your side hustle earnings are taxable! As a general rule, set aside 30% of your income for taxes, and make estimated payments quarterly.
I recommend setting up a separate business bank account and business credit card for your side hustle as soon as you can. This will help keep your business and personal finances separate, which is a big help come tax season.
For the first several years, I just tracked income and expenses in Excel, but there are lots of affordable online bookkeeping systems, including Freshbooks (better for service entrepreneurs) and Quickbooks (better for e-commerce or product businesses).
What’s the biggest mistake you see people make when they try & start a side hustle?
Going too deep into one idea before getting any sort of customer validation in the form of real dollars. Will people buy what you’re selling? If you don’t know the answer to that, ask them. If they don’t, you have to figure out why — and possibly pivot to the next idea.
You talk a lot about the failures you’ve experienced as a side hustler. How can failures actually be a good thing?
You tend to learn more from your failures than your successes, and I know that’s been the case for me. I’ve written hundreds of blog posts that almost no one ever read, launched products to crickets, and wasted tons of money on websites that — had I done just a little more research up front — were never going to work.
But in each of those cases, I’ve gotten better at:
Creating content I know my audience wants
Pre-selling products instead of spending weeks or months speculatively creating what I think will help people
Starting lean to test ideas
Do you have any financial regrets?
I regret buying a townhouse in 2007 and paying off the second mortgage on it in 2008 — only to have it crater in value and finally short sell it in 2012. Such a huge waste of money!
I regret not buying more Bitcoin in 2017. But there’s one good thing about money that you can’t say about time — you can always make more of it.
What’s your current financial goal & how are you working towards it?
Mathematically, my wife and I have already achieved a pretty comfortable level of financial independence. The bigger challenge we’re facing now is where we ultimately want to live, what the right work/life balance looks like, and how to raise a couple decent humans.
What’s the worst financial advice you’ve ever received?
Buy the most house you can afford.
What’s the best financial advice you’ve ever received?
When income from assets you control exceeds your monthly expenses, you’re free.
Image: Nastia Kobzarenko
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