5 Entrepreneurs. 5 Mistakes.
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Today, I’m sharing 5 short interviews with some of my favorite digital entrepreneurs about the biggest mistakes they made early in building their businesses.
I specifically chose these people because I love the way they leverage social media, brand building, and community to grow their businesses.
If you’re growing your audience and business, I highly recommend you read through these mistakes, understand how they were made, and take notes on how these folks would have done it differently the second time around.
Let’s dive in:
1. Dan Koe: Founder at Modern Mastery
Your biggest early business mistake:
The thing that set me back 3 years was being obsessed with “building” the business, but never putting in the effort to acquire actual customers. I spent all of my time building my “business”, standing up websites, and learning new skills. I just forgot to go land some customers. I always had an offer, but no traffic. That was a problem.
How you learned it was a mistake:
I stumbled across the term “copywriting” and dove down the rabbit hole. This was the first skill I learned where the whole purpose was to attract customers. With a newfound love for copywriting, acquiring customers became significantly easier.
What you would have done differently:
I would have started writing in public earlier with the intention of acquiring customers but also getting a ton of real-world feedback.
2. Wes Kao: Co-founder at Maven
Your biggest early business mistake:
Our vision when starting Maven was to help the “little guy” be able to build a live, cohort-based course without needing complicated tools and a big team. But about a year in, we realized we had mostly been focusing on course creators who already had big audiences. I realized there were tons of subject matter experts with smaller audiences who would be fantastic instructors, and we should re-focus on these folks.
How you learned it was a mistake:
After running hundreds of cohorts with a range of instructors, we learned there was not a clear correlation between big audience sizes and running successful courses.
Our original hypothesis was that big audiences led to successful instructors with lots of student demand, but we saw enough smaller instructors crushing it to realize we were too narrow in our thinking. These smaller instructors were motivated, resourceful, and willing to put in the effort – that was the recipe for what made for successful instructors and we needed to focus on that.
What you would have done differently:
We could have spent more time looking for signals and data points to speed up our rate of insight. But I also believe sometimes you have to make the mistake to realize you should do something else. After we realized our mistake, we became much more focused. Now we’re gearing up to launch the first marketplace for cohort-based courses, so we can help drive student demand for instructors’ courses.
3. Aadit Sheth: Founder at Maker’s Mark & Growthscribe
Your biggest early business mistake:
A big chunk of my business is driven by relationships and referrals. The biggest mistake I made early on was not investing in strong relationships to secure more of these. You can have a great service or product but if the lead is cold, it's significantly harder to sell than if the lead is warm, or referred.
How you learned it was a mistake:
I started helping out founders and entrepreneurs with audience building on Twitter by publicly Tweeting about it, sending DMs, and jumping on calls. This lead to building relationships without actively even thinking about "networking". It just felt natural. I realized right away that this was a way more enjoyable way to find better leads for my business.
What you would have done differently:
If I could do it again, I'd begin publishing online with a "give-first" mindset. I'd share 99% of what I know for free and build a high-affinity audience. I'd reach out to my ideal customers and be willing to help them at no cost. As you develop those relationships with your customers, you can eventually monetize if you'd like. This is the approach that I started taking a couple of months into my business and should have from the beginning.
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4. Ed Latimore: Founder of Mind and Fist LLC
Your biggest early business mistake:
There are so many. I think one that sticks out is that I undervalued my knowledge and position. I wasn’t charging enough for the results that I was bringing my clients. I had a big problem charging a higher rate or raising my prices.
How you learned it was a mistake:
I was seeing other people get worse results for their clients, with less experience, and charging more than me. Then I started seeing people that I helped, charge more for the same service once they had learned the skills from me. That hit hard.
What you would have done differently:
I'd charge more. I'd also work with fewer people. My early partnerships were not equal because I didn't realize just how much value I brought.
5. Katelyn Bourgoin: Founder at Customer Camp
Your biggest early business mistake:
My biggest mistake was doing customer research all f#cking wrong.
When I ran a branding agency, we didn't do much upfront buyer research. We trusted that our clients knew their customers best and let their input guide us. This was a HUGE mistake, but it was (and still is) very common in agency life.
How you learned it was a mistake:
Before launching my tech startup, I interviewed 300 people. I thought I was validating that people wanted what we were building. Forbes said we were building the next LinkedIn, but we still failed. Why? I didn't talk to the right people at the right time or ask the right questions.
What you would have done differently:
I now know that if you want to better understand why people buy, you need to speak with actual buyers (ideally people who bought recently). Don't ask them what they want. It's not their job to know what they want. Ask them to share the nitty-gritty details of their buying journey—starting with the trigger event that led them to seek a new solution right through to them buying the product, using it, and deciding if they're happy. That's where the golden insights are buried.
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