10 of my biggest mistakes in online business
Jul 15, 2025
Developing an online business was one of the best decisions I ever made. I thoroughly enjoy creating various forms of online content each day of the week, and sharing that content with people who live in places on this planet that I may never get to visit in person. Every week, I’m creating multiple podcasts, videos, blog posts, newsletters, and hosting online training sessions. Each year, I release several new books and take on new coaching clients or develop mentoring relationships. I love it all.
If I was able to go back in time about a decade and tell myself more about what I would be doing ten years into the future, I would have been thrilled to hear about it. I also would have been very pleased to know that I could earn a healthy income from those activities as well because that felt quite elusive to me when I was just getting started.
There are a lot of things that are genuinely working for me at present, but the road to developing a successful online business wasn’t always a smooth one. In fact, I have made many mistakes along the way, some of which came with a large price tag. I don’t regret those mistakes, and it doesn’t really bother me anymore to have to admit that some of them were financially expensive. At this point, I just consider the money I spent to be my “tuition” in the school of online business.
In a moment, I’m going to list my top ten business mistakes, but before I do, please allow me to acknowledge something that definitely wasn’t a mistake. I definitely got things right when I made the decision to marry my wife. She has patiently supported me all throughout our marriage, and gave me the margin to learn and grow along the way without cutting me down when some of my ideas didn’t work. She celebrated with me when I won and stood by my side when I didn’t. The victories we get to enjoy in the present would not be possible without her cooperation, trust, and support along the way. Thank you, Andrea!
Now, with all that said, here’s my Top 10 Mistakes in Online Business…
1. Paying $12,000 to develop a small-business social network without having a business plan or marketing plan. I didn’t really know what I was doing. Social media was a new concept at the time, and even the big players like MySpace and Facebook couldn’t figure out how to monetize their platforms in the early days. I should have attempted something more modest and implemented better marketing when I unveiled it.
2. Waiting several years before starting an email list. I don’t know why this intimidated me as much as it did, but I wasted years before deciding that an email list was actually important. Without an email list, I wouldn’t be able to connect with or serve many of the people I consistently serve each week.
3. Using inferior software that I found frustrating, as did my users. I attempted to save a little money when I started my first membership community, but the software I utilized gave inferior results. I wasted so many hours attempting to program it, and sadly, my members barely used its features because it wasn’t intuitive to use. When I started Platform Launchers, I decided on day one to invest in the best software I knew of, even though it cost me more than other options would have. I have never regretted that decision.
4. Resisting paying for mentors. As you could imagine, I didn’t have a lot of spare cash during the early days of developing my online business. I could have used more coaching and mentoring, but I resisted paying for it. The end result was that it took me longer to make progress than it should have.
5. Aligning with mentors even after they started demonstrating selfishness and insecurity. There are certain mentors that I eventually chose to hire, many of whom were excellent. But sadly, some online leaders talk a better game than they deliver, and I eventually realized that there are leaders who operate from a state of fear, with their greatest fear being that you might surpass their level of success. If a mentor won’t cheer for you when you’re winning, it’s time to end that business relationship.
6. Starting a dieting website that had helpful content, but paying more to advertise it than it actually earned. In the early days of the Internet, I managed to lose a lot of weight, and people started asking me for the details of what I did. It occurred to me that I might be able to sell what I did as an online diet plan. I took the time to register a domain, build a website, and market the plan, but I didn’t charge very much for it, and the marketing I was doing actually cost more than the plan earned in revenue.
7. Starting a membership community that didn’t cover my software expenses and demanded more time than I could afford to give. In the early days of online memberships, I built a membership community, but I was fearful of charging what I cost me to host it. At one point, I only charged $1.00 / month, and even at that rate, I had one member ask me for a refund. The membership attracted people who weren’t really interested in making a serious investment in themselves, and it ended up being more of a time and financial drain on me than was healthy.
8. Paying thousands of dollars for training and access to a big-name business celebrity, then realizing I would barely have any access to him at all, and the materials I was provided were inferior and gimmicky. I won’t elaborate on too many of the details, but beware of people who use the name of celebrities or famous authors to draw you into something expensive. Most of the time, it’s just a marketing trick that comes with upsell after upsell.
9. Traveling to conferences that were more hype than substance. Every conference seems to promise the greatest education, but not every conference delivers. There are some conferences I spent thousands on to attend, only to leave with very little to show for it.
10. Not maintaining healthy boundaries when people made unreasonable demands on my time. When you serve people, you’re going to experience those who are respectful of your time and those whose consciences aren’t troubled by wasting your time. If you’re a people person like I am, this may be something that can be difficult to balance. I certainly don’t want to upset anyone, but I’ve learned that it’s perfectly acceptable to set and maintain healthy professional boundaries.
All that to say, I don’t regret the process I had to go through to learn these lessons. While I don’t want to make unnecessary mistakes, I have also learned not to be fearful of making a few here and there. Making mistakes in business and in life is part of what it’s like to be an imperfect person trying to do the best job I can. My mistakes have been great instructors. I don’t want to have to take their classes more than once, but I’m grateful for the instruction they provided, even though it may have been painful at the time.
As you build your online business, don’t live in fear of making a few mistakes, and don’t beat yourself up when you make them. You’ll be fine, and your business will eventually grow. You may even look back at some of your mistakes with fondness, particularly after you’ve been able to see the growth that developed from the education you received.
© John Stange, 2025
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