Here we are, at the end of yet another year. This year, we welcomed a new baby to our family, I worked on revitalizing an old business, built a lot of websites and web applications, consulted with a number of businesses wanting to build SaaS offerings, engaged with old clients, got acquainted with new ones, helped multiple CEOs grow their organizations, experimented with new services, learned what it’s like to step from a larger organization into a smaller one, and made some serious mistakes. 

We had some great successes in 2024, but today I want to talk to you about the mistakes because I made some big ones and that’s where we learn.

Let’s take a look back.

Also, don’t forget to take a look at the free audit and this month’s free resources!

Lesson 1: Stepping Into A Smaller Team 🚷

In 2023 I exited my CEO role at a private equity-owned business through the sale of that business. I considered it a success as we had taken an asset that was previously unsellable and sold it for a very reasonable multiple on revenue. I took about 6 months off to recuperate, and in that time got excited to start back as the CEO at JHMG. But I made a critical mistake. I tried to bring the mindset and operations of a 50-person business to a 5-person business. I wanted to be a CEO, not a salesman, designer, quality engineer, operations manager, and bill collector. I wanted to do what I did at Experience Care, not be ‘in the weeds’ again.

I thought I could, but I was wrong.

I thought that I could hire for the roles that I needed and I would be able to run the same as I had at Experience Care. After all, that’s how you’re supposed to run a business, right? We were in the process of changing a lot about what we did and how we did it, we went from focusing solely on web and software development to selling consulting services and focusing on larger and more sophisticated clients.

There wasn’t a salesperson in the world who was going to help us because we didn’t have a good grasp on what we were selling or who we were selling it to. 

The company didn’t need a CEO, it needed an entrepreneur. 

The company needed a sales-focused driver who wanted to get out and talk to potential clients every day to figure out what sold best and how to maximize returns. When I started back in March of 2024, that wasn’t me.

This exact reason is why I was the 5th or 6th CEO in as many years to try to save Experience Care (the company I exited in 2023), but the only one who could. From what I can tell, the other CEOs came from much larger businesses and were ‘stepping down’ from a business of hundreds or thousands of people to a business of tens of people and this took a different mindset, a different set of skills, and a different approach to business.

I was able to step up into that role because I had all the skills of someone running a small business and was just stepping up to a larger team with more resources. While that company had a lot of problems, I was familiar with how to solve all of them and had done it many times in the past. These other CEOs were stepping down and the methods they were used to using were ineffective at the smaller business. There were still things to learn stepping up, but counterintuitively, not nearly as many as stepping down.

It’s also a lot easier to run a larger business than a smaller one because your resources are so much greater, which I think has a tendency to make people lazy or at least lazier. I’m not saying that CEOs are lazy, just that when you’re used to being able to throw money at a problem, then all of a sudden it’s you out there solving it yourself, that’s a challenge.

What did I learn? 🧠

As a CEO, your mindset and skill set have to align with the size and resources of the business you’re managing.

If your business is growing, you have to grow with it. Conversely, if it’s shrinking or you’re stepping into something smaller, you have to be willing to get your hands dirty and make things happen. I had to step back from professional CEO to Entrepreneur.

So I put back on my entrepreneur hat nine months after trying to maintain a role as a CEO and started hammering on lead generation myself. In just 3 weeks we have a lead gen system that’s working better than expected (shoutouts to Will Evans & Yota Trom for great insight and help with this). We’ve gone from just a few mediocre leads per month to several per week and there are more coming in faster and faster. After I get a few months of traction on this, I’ll share how I did it with you.

If it wasn’t so frustrating it would be funny because when I started back at JHMG in March, I told my team that I wasn’t going to be doing any of the sales or marketing, that I was going to hire for that.

And here I am eating my words.

Lesson 2: Time Constraints ⌛

As I mentioned above, we welcomed a new baby into the family. 

Mistake #1: Underestimating how much time kid #2 was going to take 🚸

A lot of people told me that having two kids is a lot different than having one. I thought to myself “I got through doing a turnaround project with huge stress and a tight timeline in the middle of Covid while having the first child (which I strongly recommend against), I’ve got this in the bag.”

I wouldn’t be mentioning it if it wasn’t a mistake, right? 

So for anyone thinking about having a second child while turning around a business, DON’T DO IT! It’s going to hurt, badly. Not only was I sleep-deprived as expected, I was totally overwhelmed with the amount of time it was taking to take care of two kids, not to mention work.

But that wasn’t the only time constraint issue.

Mistake #2: Assuming I could move as fast as I used to with a larger team 🏃

When you’re running a bigger team or have access to capital, you have a lot more resources and can move a lot faster. I was used to running at a certain speed for several years and so stepping back into a company with a lot fewer resources had me constantly biting off more than I or the team could chew. We missed important goals, we didn’t close important sales, and most importantly I didn’t spend my time focusing on the right stuff, namely sales and service-market fit.

What Did I Learn? 🧠

Lesson 1: Kids take time and more kids take a lot more time. 

When you have one kid, expect it to take roughly 2 hours per workday off of your plate if your partner is the primary caretaker of the child. When you have two kids and one of them is an infant, expect it to take roughly 5 hours per day off of your plate and expect your sleep to drop to an average of 6.5 hours per day because even if your partner is the primary caregiver of that child, now you have to help take care of them as well.

Lesson 2: Adjust expectations ahead of time.

This was probably my biggest mistake. I got the team all pumped up to grow and excited for the year, but then I constantly was behind on my work due to everything above and I felt like I was the bottleneck across the board. 

Sometimes you have to swallow your pride, realize you can’t do what you set out to do, and scale down expectations.

The team would have been happy with goals set lower and would have been happy to know we were going to have a lower growth curve for the year with greater targets for the following year, but I wanted to push, and that was the lesson of the year.

Had I scaled back expectations, cut costs earlier on, and accepted we were going to be flatter than expected because I didn’t have time and I had to be more involved in day to day ops, especially sales, I could have had a much less stressful year, probably worked a lot less, simultaneously increased EBITDA, and been much happier.

Hopefully, you can learn from my mistakes. I know I did.

Free Resources & Cool Stuff 💪

Yearly Planning Process Slides

Every year my team and I get asked to help facilitate yearly planning for companies around the world. Over years of doing this, I’ve put together a set of slides and resources that I repurpose every year. If you need an explanation or walkthrough of these, just message me.

Sales Commissions Policy Template

While I was working on all that hiring, I wrote up a pretty nice sales commission policy for an agency/consultancy. Get the template and step-by-step walkthrough here.

Deals To Check Out On AppSumo

Two deals to check out right now:

TubeIQ is pretty good. I picked this one up and sent it over to my YouTube manager. So far, it's looking like a solid competitor against some of the bigger players out there. 

Merlin is interesting, but I am not sure if I am going to keep it yet. Mostly, I like how it allows me to ask questions with whatever document is on the page via a chrome extension. But it has a LOT more capabilities that I haven’t played around with yet. This one is done in 2 days though, so get it quick if you want it.

Go To Market Strategy Analysis System

The mixture of a lack of service market fit and the need to step back into an entrepreneurial role had me doing a lot of thinking and a lot of writing. We had to rethink our Go-To-Market (GTM) strategy, and I needed a process for this. Here’s the article I wrote on it. There is a great spreadsheet in there that walks you through the whole process. Since you’re already on the newsletter, you get to skip the line and get the spreadsheet here.

Everything You Ever Wanted To Know About SaaS Monetization & Some Stuff You Didn’t

Our content team has been working on this series for a while, mostly because I kept interrupting them. We were originally doing this series for some SEO power, but it ended up being a solid read as well. If you want to learn all about SaaS monetization systems, here’s a great place to start.

Same offer as above. It’s free so I put in here twice.

For the first 10 people who contact me, I am offering a free audit of your messaging, website, and/or software. I’ll personally do a live and thorough audit and give you feedback on what and how to improve as well as how much money you can make or save by making those changes. No cost, no obligation to do anything, just Happy Holidays 💞 

That’s what I’ve got for you this time. As always I hope you found it valuable. One last thing, we’ve got some big news brewing. Look forward to a big announcement in the coming months 😀 

Keep the ideas flowing and see you next time!
Jason Long
CEO
JHMG
My LinkedIn