Lessons From My First 3 Marketing Fails
We’ve talked about the "Now, Not How" rule and the "Law of 100." But let’s be real: those first 100 reps aren't always a victory lap. In fact, some of them are downright embarrassing.
I’m a big believer that mistakes are just data points in a long-term experiment. Well, I’ve gathered a lot of "data" lately. If you’re trying to get a project off the ground, learn from my bruises so you don’t have to collect your own.
Here are the 3 amateur marketing mistakes I’ve made
1. The "Empty Pockets" Trap: Selling to People Who Can't Buy
This was my first big reality check. I had the idea, I had the passion, and I had a target audience. The problem? My target audience was broke.
It sounds harsh, but it’s a fundamental error in business logic. I was spending all my mental energy marketing to people who genuinely liked my idea but literally didn’t have the disposable income to pay for it.
The Lesson: You can have the best message in the world, but if your market doesn't have the "ability to pay," you don't have a business—you have a hobby. Now, I’m refining my focus to ensure I’m talking to people who see the value and have the means to invest in it.
1 year ago during the summer, I created a business called “Lean Ice Cream” that helped a problem I struggled with. During the hot season, I wanted to eat ice cream but I didn’t want to gain weight and go over my calorie goal. So I created a high protein and low calorie alternative to ice cream, it was absolutely fantastic. Just like Alfredo di Lelio was experimenting and perfecting his icon dish (Fettucine Alfredo), I was also trying to perfect my formula. Once I found the perfect recipe, I spent weeks pitching my services to my high school gym friends, only to realize that while they loved the help, their budget was exactly 1 Lincoln. We only really had money for a McDonald’s Big Mac. There was no way I could sell my protein ice cream to my friends for free. During this situation, I recommend you to change your audience IMMEDIATELY and start selling. Thats what I did and it paid off sort off… although there was 1 thing I lacked that could have led me to great success:
2. The "Commitment Phobia"
The best results come from total commitment to a plan. In my case, I did the opposite. I was "strategy hopping."
During that high protein ice cream business, I had a great fear of selling to strangers and I wouldn’t commit. I created distractions and did “filler” work to avoid asking more strangers. This crippled my potential growth.
My best advice for overcoming selling to strangers: JUST DO IT. Get your first 10 strangers out of the way. After those 10, the weight of giving an offer to someone will feel easier.
Also, I used to try one social media strategy for four days, decide it was "dead," and jump to email marketing. Then I’d hear a tip about SEO and abandon my emails. I used to be so busy looking for the "perfect" tactic that I never gave any single strategy enough time to actually work.
The Lesson: Consistency beats everything. You can't judge a strategy on its 3rd rep; you judge it on its 100th. I’ve realized that a "good enough" strategy executed with "A-plus" consistency will always outperform a perfect plan that you only follow halfway.
3. The Traditional vs. Digital Fiasco
I fell into the trap of thinking "Traditional" marketing felt more "real." I spent way too much time on physical outreach and old-school methods.
I was choosing the comfort of the "old way" over the scale of the "innovative way."
The Lesson: Digital isn't just a luxury; it's leverage. Traditional marketing is a one-to-one grind. Digital marketing is a one-to-many conversation. I had to stop being afraid of the digital learning curve and start leaning into the scale that online platforms provide.
I remember dressing up with a full suit and walking door-to-door for Future Business Leaders of America (FBLA), a business club at my school, thinking I was 'working hard.' The reason for me doing all this in the first place was that my FBLA chapter was fundraising to be able to fund raise our bus ride and amenities for our state competitions. Although I felt like a “hard worker” in a coal mine and I did earn some cash, it was not leveraging technology. While I was in the car ride home from eating at a restaurant with my family, I decided to make a post to fundraise. I didn’t think much about it and only made a quick little instagram story. Although this got more attention and raised almost the same amount even though it took 5 minutes (around 1/20th the effort and time of doing traditional door-to-door). That was my 'Aha' moment.
The 1/100 Pivot
I’m sharing these because I’m officially checking these mistakes off as "Experiments Completed." I’m not quitting; I’m recalibrating.
I’m moving forward with a better model, a deeper commitment, and a digital-first mindset.
What’s a marketing mistake you’ve made recently that taught you something valuable?
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