I’ve lost $320,000 on bad decisions. Not scams, mostly. Just me making the wrong call with money I’d worked hard to earn.
Every one of these mistakes is common. I see founders making the same ones all the time, usually right when their business stalls and they start looking for a shortcut.
Here are my five worst investments, what each one cost, and what I’d do differently.
1. Flipping dropshipping stores: over $100,000
My business was doing about $2 million a month, but it had stalled. I couldn’t figure out how to scale it.
A friend posted about flipping dropshipping stores for big profits. I wired over $100,000 to learn how.
A few weeks in, I realized it would take far more time than I had. It pulled my focus away from my main business, and that business’s revenue dropped. Meanwhile, the new thing never got off the ground.
The early stage of any project is like pushing a boulder uphill. Fixing the business I already had would have been far easier than starting a new one from zero.
My friend didn’t scam me. I just didn’t have the time or energy. That’s shiny object syndrome, and it’s expensive.
The real cost wasn’t the $100,000. It was the drop in my main business while my attention was somewhere else. That’s the part nobody puts in the pitch.
2. A two day YouTube coaching session: over $50,000
I paid over $50,000 for a two day in person session with a coach who had worked with a famous YouTuber. I expected a breakthrough for my channel.
Most of the time went to defining my target audience and offer, then breaking down top YouTube videos.
None of it was new. There’s no secret sauce. It’s consistent effort and adjusting based on your analytics. I could have saved the money and just done the work.
That’s true for most platforms. Pick your audience, make a clear offer, study what’s already working, post consistently, and adjust based on the numbers. If someone is selling you a secret beyond that, be skeptical.
3. Five paid ads coaches: about $50,000
In 2017 I relied entirely on paid ads, and they weren’t working. I believed ads were the fastest way to go from broke to rich, so I kept paying for help.
I hired five coaches at roughly $10,000 each. They mostly showed me the same material.
Here’s what makes it worse. I was funding this by doing $20,000 to $30,000 a month from organic messaging, working 10 to 16 hour days while living with my parents. My dad pointed out that I’d be richer if I had just kept the cash.
To be fair, a coach isn’t fully responsible for your results. The student has to make it work. And learning what not to do has value. But five coaches teaching the same basics is a lesson I only needed once.
4. Middlemen for account recovery: $5,000 to $10,000 a time
My Instagram account was banned several times. Each time, I paid middlemen who claimed to know reps at Meta, often $5,000 to $10,000 per attempt.
Results were all over the place. They overpromised, couldn’t deliver, and often wouldn’t refund.
Now I go directly to the people who actually have control. If you have an account issue, go to the source, not a middleman. Every layer between you and the person who can fix it adds cost and removes accountability.
5. A crypto fund: $100,000
Friends showed me a fund claiming around 10% returns per month. Most investments return about 10% per year. That alone should have stopped me.
It was friends who brought it to me, which made it easier to say yes. Trusting the people doesn’t mean you should trust the numbers.
It showed strong returns for a few months. Then it disappeared with the money. Crypto is poorly regulated, which makes this kind of thing easier to pull off.
For most founders, crypto isn’t a good use of time anyway. Learning a new market takes energy away from the thing that already makes you money.
The pattern behind all five
Look at the list again. Almost every loss came from the same place: I stopped focusing on what was working and went looking for something faster.
- The store flipping pulled me away from a $2 million a month business.
- The YouTube and ads coaching sold me basics I already knew or could have figured out by doing the work.
- The account middlemen and the crypto fund promised fast fixes and fast returns.
When your business stalls, the urge is to add something new. Usually the better move is to go back to the thing you already have and fix what’s broken.
The takeaway
- Stay in your lane. Learn one thing well. Side interests are fine, but splitting your focus isn’t worth it. Fully switching is a different decision.
- Check what you’re paying for. Coaches and consultants often repeat the same basics. Make sure you’re buying something new.
- Be wary of quick fixes. Especially through intermediaries, and especially with returns that sound too good.
I lost $320,000, but I gained a lot of wisdom. Mistakes are tuition. It’s a lot cheaper to learn from mine than to pay for your own.
Before you spend on the next shiny object, find out what’s actually capping your business. Take my free 90 Day Ceiling Plan. Answer 18 questions and get a written plan, built on your own numbers, that names the one thing holding you back and what to fix first.
