How Do I Actually Make Money By Starting My Own Business?

<div class="user-question">Hi Frich, I’m considering starting a business as a side hustle – how do I actually do it & what should I keep in mind?</div>

Hey there and thanks for the question! I love seeing more people explore small business ownership. It’s challenging, yes – but it’s also fun, empowering, and honestly one of the most worthwhile things I’ve ever done.

I’m the CEO and co-founder of Uprise. We help small business owners with their taxes and finances - things like choosing the right legal structure, understanding tax deductions, setting up for retirement as a business owner, and making smart decisions as you grow.

I pretty much live and breathe this question every day.

Here’s the short answer: it’s 100% worth it, but it’s not a joke. The market doesn’t hand out participation trophies. If you don’t put in the work, you don’t make the money.

But if you do put in the work, you’ll learn more about business, customers, and yourself than any class or W-2 job could ever teach you. Plus, there are some nice tax perks to being a business owner!

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1️⃣ Know Your Why

Before anything else, ask why you’re doing this.

Are you trying to make work optional by 35? Pay off debt? Save for a house? Or just build something of your own?

Your side hustle is a tool. Without a personal goal, it’s easy to chase growth for growth’s sake, or burn out doing something that was never aligned with what you actually wanted.

With anything you do, I’m the biggest believer in being deliberate first and foremost.

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2️⃣ Treat It Like a Business

When you start the side hustle, the first thing you should do is to treat it like a real company. Because that’s what it is. That means -

• Set up a business bank account. Don’t let your Venmo and DoorDash receipts get mixed in with your earnings. This will matter a ton at tax time.

<div class="frich-tip">Frich tip: Here's Frich team's top choice!</div>

• Use a bookkeeping / expense tracking tool. I like Wave – it’s free to start and makes it easy to track expenses and receipts. Other options are Xero, Freshbooks, and Quickbooks Self Employed. Clean records will also matter a ton at tax time.
• Understand your new tax responsibilities. Things will get more complex. You may need to file extra forms and pay quarterly estimated taxes. But here’s the upside: you unlock a whole new world of tax savings and strategies that W-2 employees don’t get access to. Here are some examples:
• • Startup costs - setting up a website, registering a domain, registering a legal entity
  • Home office - if you operate your side hustle from home, you can write off parts of your rent, insurance, utilities, internet, and more
  • Mileage - if you drive as part of your side hustle (Uber/Lyft definitely, but also when you head out on business errands), you can deduct the miles you drive

These are some of the basic ones and there are a ton more out there. These topics can get complex fast. My advice is to not stress too much over these upfront. Focus on building the business and track everything. (Sense a pattern?)

<div class="frich-tip">At tax time, whether you use a DIY tool like H&R Block or work with a pro, having those records ready will make your life way easier and ensure you capture every deduction.</div>

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3️⃣ Ask for Help

You don’t have to figure this out alone. If you’re unsure about taxes or finances, talk to a professional. (That’s literally what we do at Uprise.)

Here are a few smart questions to ask:

• What type of legal entity should I be?
  Sole prop, partnership, LLC, S Corp, C Corp - all valid depending on your business model and goals, and there’s an element of tax planning here as well.
• What can I deduct?
  Deductions depend heavily on the business, so 1:1 guidance can help you know what you should be tracking.
• Do I need to pay quarterly taxes?
  Once you’re earning income, Uncle Sam wants his cut on a quarterly basis. You can do this through your employer (if you still have a W-2 job) or directly to the IRS.
• Can I set up a retirement plan as a business owner?
  Yes! You may be eligible for a Solo 401k, SEP IRA, or other plans. Some of these have even higher contribution limits and tax benefits than what most W-2 employees get through a regular job. Worth asking about as you start to make consistent income.

More broadly, outside of finance, lean on other business owners. They’ve faced similar challenges and finding a community can be incredibly helpful as you get started.

A single good conversation can save hours of Googling and frustration.

<div class="frich-tip">Whether you're setting money aside for your taxes or you're building up a safety cushion for the inevitable ups & downs, we always recommend having some money set aside in a HYSA. Here are accounts that the Frich team likes.</div>

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4️⃣ Work Smarter, Not Just Harder

You’ve maybe heard this line for small business owners: “Work on your business, not in your business.” But what does that actually mean?

Working in your business is doing the day-to-day tasks: delivering the service, packing the orders, replying to customers.

Working on your business means zooming out and improving how the work gets done. A few examples:

• Setting up templates and automations for repeat messages or emails
• Reviewing what activities are working (and what’s not) at least once a month
• Revisiting your pricing if you’re charging for time or services
• Using tools like Notion or Trello to organize tasks, or Calendly to avoid email back-and-forth
• Use tools that simplify tasks that used to require a lot of time and expertise, like Canva for design

That strategic time is where real growth happens. Make space for both.

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Btw - here's how others are doing👀

Would you take a 20% pay cut for a job with no stress?

👍39% Yes, I’d rather make less money & have a chill job

👎61% No, my priority is to maximize how much I earn

The last thing I’ll say is: expect the rollercoaster. A side hustle isn’t passive income. It’s just income, earned through effort and uncertainty.

Some days you feel unstoppable. Other days you question everything. That’s normal.

For me, the hardest part of being my own boss isn’t the work, it’s managing my own mind. I meditate daily to stay grounded. Find your own version of that.

And whether your side hustle becomes your full-time gig or stays something you do on the side, it will stretch you in all the right ways. It builds confidence, grit, awareness. Those are skills that will stick with you for life.

You got this,

Jessica