SBM #5 - Corner Alliance at $20m

If you want your company to grow, learn to delegate. 

Small Business Black Holes exists to tell insightful, interesting stories about initially successful small businesses who found themselves in black holes and, through whatever means necessary, climbed out of them.

As always, this won’t be the longest email on earth. 

You’re busy. I’m busy. 

Last time, we looked at how Once Upon A Farm boosted sales by listening to their audience and adjusting their marketing strategy.

Today, let’s return to the next chapter in my business: Corner Alliance.

📓 The Overview

  • Business: Corner Alliance

  • Revenue Barrier: $20 Million

  • Learning: Stop making all the decisions, hire a team to do that

📓 The Story

So our main takeaway from the last Corner Alliance story was to put your knowledge into your business processes and the importance of having the right team. 

And this week we continue to expound on this theory.

At this time, we were just over that $15 million a year barrier and heading towards $20m. 

I had a leadership team and a strong pipeline of returning clients. 

Overall, everything seemed great. 

Then along came ChatGPT, an AI technology that took the world by storm.

And as soon as it did, I said to my team: “This is the future!” 

AI was going to disrupt the professional services world and I wanted to be the disruptor, not the disrupted. 

I started doing a lot of different things all at once. 

We started to implement ChatGPT training. 

We wanted to make sure that the knowledge of how to utilize this tool was embedded in all of our team members. 

We started a newsletter (not the one you’re reading now) and a podcast and just kept trying things out to see if we could figure out a way to capitalize on the AI trend. 

But none of it was making a difference in the company. 

Hardly anyone was using AI in their day-to-day work and each initiative was happening in isolation. 

None of it amounted to a strategy that could grow the company. 

It took me a while to realize what I was doing wrong: 

  • I was going too fast 

  • I was making all the decisions 

That last point stuck with me. 

As a company gets bigger, the hustler mentality becomes less and less effective as a CEO. 

Sure I could get some things done but my actions couldn’t drive culture change. 

I had a team of leaders, but all the decisions were coming from me.

I wasn’t bringing them into the conversation, I was just telling them what to do. 

I wanted them to take the initiative instead of waiting for me to decide. 

So, I brought in a fractional CTO and positioned my lead delivery person to work with him to drive the effort and I got out of the way.

These were two qualified people who would be able to look at our services and implement a long-term AI strategy. 

I had to learn to trust them. 

Trust them to take the lead. 

I had to go from hustler founder to something more like an orchestra conductor.

I had to slow down and give them a chance to experiment with the technology and build a solution to benefit our team and our customers.

And it worked - today we have processes developed to enhance our team's capabilities with AI tools. 

This allows us to confidently bid on AI contracts. 

🧑‍🎓 The Lessons: 

  1. You can’t be the one making all the decisions. You have a leadership team: trust their expertise and listen to them.

  1. Take the time to plan your approach and don’t jump into a trend too fast.

  2. You have to learn to sit back and let things play out. Let the team experiment and test so they can develop a solution that will lead to long-term success.

📅 Next Week:

Stay tuned, because next week we jump into another small business story learning more about the significance of culture, the power of mentorship and how effort compounds. 

Keep growing,



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