3 Biggest Money Mistakes I've Made in My Online Business (And How to Avoid Them)
We've all been there. You're scrolling Instagram, a Facebook ad catches your eye, or your favorite business influencer swears by some tool or coach that will "change everything." Next thing you know, you've got another subscription, another hire, another program—and your bank account is lighter while your revenue stays the same.
The hardest part of running an online business isn't finding clients or creating offers—it's resisting the constant pressure to spend on things you don't actually need.
If I took proper stock of the low-return investments I've made in my business over the years, I'd probably cry. So I'm not going to do a deep dive into my own P&L here, but I will share my biggest regrets, the reasoning behind them, and what I wish I'd known before hitting "purchase."
Mistake #1: Hiring VAs and OBMs Too Early
Let me be clear: this is no shade to the amazing people I've worked with. Virtual assistants and online business managers are invaluable. There IS an inflection point where hiring becomes the key to growth.
But here's what nobody tells you: if you're making under $350,000 annually, you're probably not there yet.
I learned this the hard way. I was sucked in by multi-million-dollar business owners who gushed about how essential their VAs were to their growth. What they never mentioned was when they hired them—and what their revenue looked like at that point.
Why Early Hiring Often Backfires
In the pre-$350k phase, the ROI on general business support typically isn't high enough to justify the cost. You're still figuring out your offers, your systems, your sales process. Adding team members creates management overhead that can actually slow you down.
Here's what I experienced:
Spending hours creating SOPs and training docs (time I could've spent on revenue-generating activities)
Managing someone else's schedule and tasks instead of focusing on my own
Paying $1,500-3,000/month for support that didn't directly increase revenue
The Exceptions to the Rule
There ARE smart reasons to hire early:
Agency-style businesses that hire VAs to fulfill client deliverables. This makes sense because clients pay for it, and it allows you to scale capacity.
Personal assistants who handle life admin (filing insurance claims, booking travel, managing household tasks). These actually give you time back for revenue-generating work.
My advice: Focus on getting to $350k solo first. Build systems, refine your offers, and understand your business deeply. Then hire strategically with a clear ROI in mind.
Mistake #2: Death by a Thousand Subscriptions (AKA Tech Stack Bloat)
Pop quiz: Open your credit card statement right now and count how many software subscriptions you're paying for.
I'll wait.
Shocking, right?
I've made some incredible tech investments: ConvertKit for email marketing, Sunsama for project management, Opus for content repurposing. These tools genuinely save me time and make me money.
But I've also been horrifyingly click-happy on subscriptions I couldn't use enough to justify—or worse, forgot I even had.
The $980 Wake-Up Call
After the great Asana saga of 2025, when I was auto-renewed for $980 with zero warning (and zero refund), I changed my entire approach. Now I only sign up for monthly subscriptions on anything new.
Yes, I miss out on the "annual savings" discount. But I gain something more valuable: the ability to opt out without losing hundreds of dollars.
My 3-Question Tech Stack Framework
Before adding any new tool, I ask myself:
Time to integrate: How much time will it take to set up, learn, and actually implement this?
Impact/Value: What specific problem does this solve, and what's the ROI?
Job to be done: What is this tool's specific role in my workflow?
These three questions have saved me thousands of dollars in unnecessary subscriptions.
Action step: Set a calendar reminder right now to audit your subscriptions quarterly. Cancel anything you haven't used in 60 days.
Mistake #3: Falling for the Online Business Grifter Industrial Complex
Thankfully, I haven't made this mistake too many times. But when I have? It stung.
You know the type. They slide into your DMs or show up in your feed right when you're feeling especially defeated:
"You're sitting on a GOLDMINE"
"You could be making $50K months in no time"
"Honestly, you SHOULD be running a million-dollar business"
The Sales Psychology That Got Me
Here's how insidious this is: I once had a friend ask about my experience with a certain business coach. I gave a lukewarm recommendation. "Learned a lot, got what I needed, wouldn't go back."
Three weeks later, I was signed up for another year with this person.
What in the sales psychology wizardry happened there? I still don't fully know, but I can tell you: while I didn't regret round one, I DEEPLY regretted round two.
The Truth About Courses and Coaching
At a certain point, you know enough. You have the tools, the frameworks, the strategies.
What you actually need is accountability to put it all to work.
And here's the hard truth: you can't pay anyone else to do that for you. So keep that $5,000 for yourself and invest it in your business instead.
How to Spot the Grifters
🚩 They use FOMO and urgency tactics constantly
🚩 They promise specific revenue numbers
🚩 Their content is all hype, no substance
🚩 They target you when you're vulnerable
🚩 They don't have real case studies or results
There ARE Good Investments… They're Just Strategy-Led
Not all business spending is bad. I've made plenty of investments that paid off 10x:
My email marketing platform
A brand photoshoot that elevated my positioning
A copywriter who helped me nail my messaging
Strategic coaching at the right time in my business
The difference? These investments were tied to a clear strategy.
Your investments shouldn't define your strategy—your strategy should define your investments. Mixing this up is the mistake most people make, and it leads to regret, wasted money, and a bloated business that's more complicated than it needs to be.
The Bottom Line
Building a sustainable online business isn't about having the fanciest tech stack, the biggest team, or working with the most expensive coaches.
It's about making strategic investments that directly support your revenue goals—and having the discipline to say no to everything else.
Your bank account will thank you.
Need to get more strategic in your business? Get my free Revenue Roadmap for Entrepreneurs.