The Longer “About Tim Kilroy”

I help performance marketing agencies explode their client acquisition & retention to create more revenue, more profit & more happy.

I’ve been building businesses since 1997. Some have been really successful (sold to bigger companies) and others have crashed and burned so hard that FEMA had to report to the scene.

In 1997, I started a digital marketing consultancy. That wasn’t my first business (a paper route was), but that was my first terrible business. I was a solo consultant who thought I was building something. But I wasn’t. I was trading time for money, and getting paid for activity rather than impact. I couldn’t scale beyond the needs of my biggest customer. That worked out well enough. The big customer absorbed my business, and I happily joined as an employee. I thought that was what an exit meant – you started something and someone made it worth your while to do if FOR them rather than WITH them. I thought this was a grand success, so here is what I heard in my head: My first real business got absorbed by a NASDAQ-traded company!

I was brilliant, right?

Well, that was during the 1st dot-com boom. Shortly thereafter, during the dot com crash, they closed the business I worked on. By then, I had a mortgage, a pregnant wife, and no job.

I didn’t feel so brilliant.
I Didn’t Know As Much As I Thought

What I didn’t know about business than would have filled an encyclopedia. But I had just taken the safe route when my last business merged into a big company and I became an employee. I did my job well, but forces way beyond me were at work. My financial safety net, my paycheck, was ripped away from me without warning. My beautiful pregnant wife and my now scary mortgage payment needed someone to take care of them. So, I decided to make another business – my 1st agency.
So, I launched my dream – an awesome marketing agency.
I got clients and started to grow this business. But there was a problem. I didn’t have a clear focus. I didn’t have a clear vision of my services, and I had no idea who my ideal customer was. But I was stretched so thin and everything was SO hard. I was working for myself, following my dreams, and making myself totally miserable.

Then I Got Some Good Advice

My agency was trying to help small businesses transform themselves into digital entities. I was going to be their Sherpa into the magical world of digital. I was spouting off fancy terms like “effective CPM” and “cost per click”. I was really focused on what I knew. It was pretty clear to me that I knew so much more about this than my target clients did, so they should just follow me. After all, I was the guy on the bleeding edge!
But, I was struggling, badly.

But, I was struggling, badly.

I was making a classic entrepreneur mistake. I was focused on what I did. I was wrapped up in all of my stuff. Sometimes, entrepreneurs like you and me can get carried away with the excitement of our ideas, with the intricacies, with the nuances. But when you are an entrepreneur, you are building something – but other people use it. What you do has to connect with them. Then, an older prospect I pitched said something shocking to me: “Stop trying to be smart and start trying to help…”

That hit me like a ton of bricks. Of course I was helping! I was leading the way! I was forward progress! I was what’s next! I didn’t believe him. At my next pitch meeting, 100% to prove this guy wrong, I decided to try his approach. Instead of starting off with what I could do for this potential client and assuming that they would connect the dots, I started off the meeting by asking what marketing issues they had trouble with. That made a connection – and a sale. Suddenly, my business began to grow. 4-figure months turned into 5-figure months, and a 5-figure business turned into a 6-figure business. Things started to get easier.

But I Wasn’t Through Making Mistakes – Or Learning

That business started to grow. But I didn’t. I still needed to feel important. I needed to be involved with everything. After all, this was my business. From selling to strategy to service delivery to billing to banking, it all worked through me. I was at the hub of it all. And I was miserable. Again, I was following my dreams, my plans, and I created a system where I was critical to the success and operation of my company, and I was really unhappy. I was unhappy because I wasn’t focused on the things I am good at – that was cluttered because I was busy thinking about accounting, phone bills, invoices and insurance plans. I had myself important, I had to be smart, and I was super busy. And it sucked.

Then, It Got Awful

Eventually, that business ran itself into the ground. I couldn’t figure out how to not have myself in the middle of everything. It made me angry. At the end of the day, I was too unhappy to put up with all that needed to get done, and we crashed hard. It was unbelievable – we grew to a healthy size because I learned how to make other people’s needs the focus of what we offered. We grew because we became of service. But we crashed because we weren’t shaped properly.
It wasn’t a business problem. It wasn’t a sales problem. It was my problem. The business crashed because I couldn’t save it because I was unhappy running the business. And that is nuts because ever since my 1st job, I always wanted to be the guy who runs the show. But doing it wasn’t enough because building a business is really, really hard. It is time pressure, resource constraints, growing demands, cashflow concerns, employee issues, and a thousand other things all at the same time. The demands of building a business are pretty extraordinary. And for years, I couldn’t wait to get out of bed in the morning and solve these issues. And then, one day, it was just too hard. I didn’t know why I was doing it anymore.

At this point, I was lost. I had 3 kids and a bigger mortgage. And I didn’t know what to do next.

Finally, Light at the End of the Tunnel

After I wound down my company, I floundered. I didn’t know what to do next. But, we were dead broke. So, I went and got a job. The job was fine. But my heart wasn’t in it at all.
So I wanted to start another company. But I completely understood that I was the problem. So, I needed to understand how I could be perfectly well aligned with my business. How could I be of service to my customers? How could I focus on the parts of the business that I was good at? How could I focus on doing the parts of the business that are needed that don’t core to my sense of worth?
It occurred to me one day, as I was holding my baby daughter, that I was asking the wrong question. I shouldn’t have been asking “how”, I should have been asking “why”. Because why I wanted to build a business was the driving force behind what I was doing. It should have been clear to me all along, but the “why” was my children. At the time, I had 3 great little people under 4 years old. Now we have 5 amazing children – and they are mine, why?

When your “why” is crystal clear, knowing what you do is easier. In my case, early in my entrepreneurial career, if my why was something other than “make money” and “feel smart”, connecting what I do to customers would have been easier. Later, as we were scaling, if my why had been something other than “feeling happy”, I could have more easily solved the structural issues my company faced. Knowing your “why” makes what you do more clear.

It Gets Better – I Learned

After that debacle, since I had my why’s clear, and I knew how to connect to my customers with the context of what I do, I started other agencies. I learned the secrets of creating a scalable & saleable agency, I learned to create meaningful goals. I learned to create meaningful, measurable goals and I learned to scale & manage the process. These life lessons pushed me around a bit. They forced me into dealing with my ADHD. They forced me to create frameworks, like those we teach in Agency Breakout & Agency Accelerator to create and manage dramatic growth. (And that lead to me selling those agencies, too – so I know these approaches work.)