15 Mistakes I've Made as a Founder
From 6.5 years and multiple 7-figure startups.
I’ve built multiple 7-figure startups in the past 6.5 years.
Bell Curve is a growth agency (twice—long story).
Demand Curve is a growth education/media business.
And likely in 2024, Unignorable. We hit $500k in 9 months part-time from 3 cohorts.
The past 6.5 years have been a series of mistakes.
And suffering from past mistakes.
And trying to correct those mistakes.
And in the process, making more mistakes.
Here are some of the biggest mistakes I’ve made in 6.5 years:
#1. Thought I was the sh*t.
Many times, I’ve blissfully sat atop Child’s Hill, overconfident about my skills as an entrepreneur, given our series of early successes.
Landing Microsoft as a client, and being invited to apply to Y Combinator and getting in despite putting little effort in was probably the peak. Then, I came crashing down as the tech recession hit, and the easy wins stopped coming.
It’s made me a better entrepreneur and marketer in the process.
But it’s been humbling.
#2. Hired the wrong people
When we started the agency, we hired folks who were too junior at growth marketing and had never worked in an agency before.
And we had never built an agency before.
This meant that we had to train them to do everything. That meant we had to learn how to run an agency and then teach it to everyone.
The definition of “the blind leading the blind.”
But this meant we got very good at learning and SOPing everything we did.
We’ve gotten better, but we have messed this up a lot.
#3. Hired too soon
When revenue is going up, you feel the obvious choice is to spend more of it on more people so you can do more things, right?
Well, unless you have an obvious need for those people and how they will either:
Drive even more revenue directly
Make you or someone else more able to drive revenue directly
Then you end up spending more money and managing more people.
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#4. Fired too late
It’s hard to fire someone—especially the loveable B player.
Someone you really like personally, who isn’t necessarily harming but isn’t the person to help take your company to the next level.
Firing people feels like a step back, and it takes a lot of humility and bravery to accept that you were wrong and that someone else needs to suffer because of it.
But it’s necessary.
#5. Did too many things
It is extraordinarily tempting to do more things rather than do more of the right thing.
Here’s how it plays out:
You launch a product/service that people buy and is growing.
You go: “We should create another one; we could immediately double the revenue, and that’ll grow too!”
Then, the initial burst of sales from the launch slows down. Excitement wanes. And now you’re managing two products and teams, marketing two things, and mixing your messaging.
If you find something that works, do that thing until:
You sell a lot of it.
People love it.
It’s getting more and more profitable and easy to run.
Then, you can add complexity.
#6. Didn’t stop to question the long-term implications
Related to #5, I didn’t stop to ask, well, if we launched/did this, what does that mean two years from now?
For example, we launched a free Slack community for growth marketers. We got hundreds and then thousands of applicants within months. But we realized that they were people at different stages of their careers.
CMOs/CEOs at big companies.
Founders of Seed and Series A companies.
And those completely new to entrepreneurship and marketing.
By mixing them all, we knew we might lose the high-caliber folks because they’d be annoyed by basic questions: “How run Facebook ad?”
So, we launched 3 Slack communities. Seemed logical at the time.
Then, when you have 20,000 people apply, it becomes a complete nightmare to organize. And we didn’t even know if it was ROI positive before doing that.
We should have paused to ask, “what happens if this succeeds?”
#7. Didn’t go niche enough
At the time, it seemed somewhat niche.
We “do and teach growth marketing for/to startups.”
The problem is that the needs of a bootstrapped B2B SaaS founder and a Series A DTC ecomm CMO are pretty different.
So, writing our newsletter has required mixing tactics/strategies for all kinds of startups at all stages.
Choosing which topics to focus on for our content has proved difficult.
It wasn’t until recently that we’ve done a way better job creating clear, productized services and offers, like:
$6k/mo ads management for startups spending up to $50k/mo on ads.
$7k ~ $20k to develop your brand’s positioning and story
$800 for a cohort to learn personal audience building
Selling these is easier because they’re clearer. And it’s easier for us to create content because we know which lanes to stay in.
#8. Didn’t delegate enough
I’m a freelance programmer turned marketer and founder.
Independent tinkerers and doers have difficulty getting out of the way and letting others do the work. Particularly if it’s work they enjoy (coding, design, writing, etc).
At some point, the founder must not “work in the business.” They must “work on the business.”
I’ve ranged from terrible at this to not great. I’m getting better, but I still have a lot of room for improvement.
#9. Delegated too liberally
When the work has been outside my expertise, I’ve sometimes been too quick to delegate and offload the responsibility entirely.
This has bitten me in the ass.
It’s still my business, and I must take responsibility for the outcome/output.
#10. Invested in the wrong thing
Whether due to ignorance or arrogance, there have been times I’ve just invested time and money in something that wasn’t worth investing in.
Pausing to be more strategic and get more outside perspective could have saved a lot of time, effort, and money.
#11. Made too complicated of a product
In an attempt to differentiate, it’s really easy in B2B to accidentally create a confusing, complicated, or nebulous product or service.
An agency that does “full-service growth” may be an excellent service to help companies grow, but it’s:
Hard for us to explain what that means and why it’s valuable
Hard for prospects to identify “Oh, yes I need that.”
Hard for friends to recommend you because they don’t understand it
Hard for prospects to know what’s a fair price.
Again, products/services with clear outcomes, prices, and audiences make it easy for people to understand, value, and recommend.
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#12. Didn’t invest in the long term
Hiring too quickly, firing too late, investing in the wrong initiatives, and a recession led to times when we had to prioritize short-term initiatives instead of long-term ones.
Do what you can to get cash in the door today instead of building a system that brings even more cash to you in a repeatable and scalable way.
For example, we should have:
Built our personal audiences earlier
Created a podcast
Invested heavily into SEO or ads to grow our newsletter
If we had, we’d have a larger audience, better distribution, and more assets to sell sponsorships and pitch our services in.
#13. Added business partners/cofounders too liberally
Be very careful who you give equity to.
Cofounder relationships are essentially marriages. Marriages involving a lot of money, and people get funny when money is in the mix.
Do a lot of vetting before you bring on a cofounder, CEO, or a significant shareholder.
It can bite you in the ass for years and even kill the business.
#14. Let my past define me
As I said, my background is freelance programming and writing.
I run marketing companies. This created a few problems:
#1. Imposter Syndrome.
I’ve hired and worked with many folks with more marketing experience than me.
What right did I have as a programmer to talk about marketing online?
Or to speak my mind about our marketing, products, and content?
#2. Feeling lost.
If you identify as a programmer and own marketing companies, you can feel disconnected from what you’ve built.
“Am I doing the right thing? Should I be the one running this?”
It wasn’t until I had an identity shift in myself (“Wait, I’ve got years of marketing experience now”) and a framing shift (“We’re not a ‘marketing company’; we help entrepreneurs build businesses and products”).
#15. Hid behind the brand and my cofounder
Our company was bootstrapped off my cofounder’s network and personal audience.
But he didn’t want to be the face of the brand, and he didn’t like to be too promotional, so we tried to build our brand. We’ve been decently successful at that.
But the market has shifted, and people prefer to follow people, not faceless brands.
My identity as a “programmer” and my imposter syndrome kept me from stepping out from behind the brand and being the face of it.
I started to do that a year ago and have grown to over 50k followers. And I wish I had done it sooner. It’s significantly impacted my life and our business.
There’s probably a lot more.
It’s hard to read the label from inside the jar. So, I probably missed a ton.
And I’m 6.5 years into this journey and only 34 years old.
I will make many more mistakes—hopefully fewer—but each one is a great learning experience for me to be a little bit less dumb.
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