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5 Embarrassingly Dumb Mistakes I Have Made as CEO of a Digital Agency

Facepalm. If you can learn from my mistakes, maybe it won’t be all for nothing?

Its been 5 years since Josh and I started our first company together. It has been the most awe-inspiring journey, and I couldn’t be happier.

As we transition our company into a new phase, I’ve spent a lot of time reflecting on what went right and wrong.

Here are the 5 biggest and most embarrassing mistakes I have made:


1 – Choosing “interruption” marketing over “inbound” marketing.

Outbound marketing is the WORST. I don’t know what I was thinking, really. Especially as a digital marketing company – why wasn’t I implementing the exact strategies that we implemented for our clients? I was doing the opposite of the exact service our company provides. Please tell me, because I can’t answer this question.

2 – Choosing a wide audience

This is such a common mistake in business. Entrepreneurs tend to think that widening their audience is a more intelligent decision than closing in on a very specific subset of buyers. This means that many businesses are targeting the average buyer, with an average product, at an average price point. It may seem like there are many more buyers in this “middle” category, and that you can bring people in from many different places.

The opposite is true.

In many cases, the wider your net, the lower you will perform. Take the headshot photographer who took my photo. I chose him because he was A) ranked on Google B) had the image style I was looking for and C) he specialized in headshots only. He didn’t have family photos on his website. Or weddings. Or anything weird. He had professional headshots.

3 – Taking short-cuts.

Eeek. (Winces). If you want to build a respectable company, never cut corners that involve compromising your quality of service/product/reputation/etc. Its just not worth it. Do things right from the beginning. I really don’t even want to talk about this one. I’m too ashamed!

If you’re going through all the trouble of building yourself something (like a house, or a business) you’d better make sure you’ve done it on a solid foundation. Otherwise, you’re just wasting your time and resources, because what you’ve built isn’t going to last.

Thankfully, the short-cuts I decided to take weren’t detrimental. I was able to fix things and make adjustments. But it would have been a helluva lot easier if I had done things right in the first place.

4 – Poor hiring decisions.

Hiring, hiring, hiring. Hiring has got to be one of the most difficult aspects of running a business. Finding talent, and keeping it.

My biggest mistake when it comes to hiring, is lack of due diligence. I really thought that the right person would just “show up.” I also thought that I could train someone to be the kind of person that I wanted.

But really, your team is your biggest asset. You are only as strong as your weakest link! It took me a long time to realize that its okay to be picky about who is on your team, and to only hire after extensive interviews (and 2nd interviews).

5 – Lack of networking.

In our first few years, we spent 0% of our time networking.

When I was growing up, I was always annoyed by people who got places by “knowing someone.” I guess because of this, I was determined to do things all on my own.

Thats great and all, and I’ve done really well operating the business in a complete vacuum, cut-off from all other people in the world.

However, networking builds connections, and some of these connections can actually HELP. Shocker I know.

….What Went Right Then?

And just to balance things out a little bit, here are 5 things that went right, that have contributed to our success despite any silly mistakes I have made.

1 – Our partnership

Josh is basically the best thing about 4theweb (oh and, about my whole life).

Josh is the perfect business partner. He makes all my wild ideas come to life (Brittany from 2011: “babe, I want to try this new method I discovered that promises to make thousands of dollars online. Its not a scam, I swear!”).

He also offers endless support (I mean endless, even when I’m doing everything on my side wrong). His optimism and positivity is nonsensical, but it works.

Basically, he does everything awesomely that I suck at. I didn’t talk to a single client for the first 4 years of being in business, because I’m too socially awkward to be normal with other humans. His strengths are my weaknesses.

I have decided that most people are capable of achieving great things. But I think its extremely difficult to do alone. Having the right partner can mean the difference in success and failure.

And in our case, it worked out just right.

2 – Our [intelligent] investment in ourselves

We aren’t afraid to invest in ourselves.


Josh wasn’t afraid to invest in ourselves.

If it were up to me, I wouldn’t have done it. After the first time I failed, I would have given up, at least for a while. I might have been able to achieve what we have achieved, but it would have taken me WAY longer.

Josh has always been a major proponent in trying things, even if they fail. I am the opposite. I am a savorer, so I don’t want to spend any time or money unless I know for absolute sure that I will get some kind of measurable return. Unfortunately, my way of thinking is detrimental for growth (and is a terrible attitude for a business owner)!

This is why our partnership is so crucial to everything that we have built (read #1 again).

I consider our business to be successful thus far. However, in order to get here, we have invested a ton of time and money. It didn’t come for free.

Just as an example – I have spent over $100,000 on buying links and link software alone. At least half of these links I bought were worthless. But I had to learn. I have spent $30-40k on digital courses. I will easily spend $15,000 on one ticket to a marketing conference that I need to go to.

For my newest product launch (iCanSEO) I will spend around $50k/month in ad spend.

Don’t take this the wrong way here. Don’t go buying yourself all kinds of crap, and call it “investing in yourself.” But if you need to learn something to move your business forward, then spend the money. You’d easily spend 20k on 1 year of college education. So do what you need to do to further your career.

3 – Obsession

Our obsession with creating a successful business is what drives us. Its the reason that I learned SEO in the first place – I was ambitious and determined.

The word “obsess” usually has some kind of bad connotation. But in business, it works pretty well. Obsess over something enough, and you will become the best at it. Be the best at something, and you will be able to succeed.

You can make lots of money from ANYTHING. I mean, anything. But it takes obsession to make it happen in a big way.

4 – Fluidity

We are always open to changing gears, switching directions, and we are constantly re-evaluating our path, our goals, and our course of action.

Sometimes this is bad. A lack of steady consistency toward one single idea means that we accomplish “less.” But it also means that we get smarter, adjust our course, and avoid dumping hundreds of hours of time (and money) into a project that wasn’t really the “right” thing for us.

It also keeps us on our toes. I think changing your perspective keeps your brain alive and opens your mind up to new possibilities.

5 – Susanna!!

Susanna is a crucial part of our team and of our success. Good people are ridiculously difficult to find, but somehow we managed to do it (and on our first try!).

For some weird reason, Susanna has stayed committed to us through all our twists and turns. Knowing that we have someone loyal on our team that we can count on has been essential to our growth, our freedom, and our success.

I also ask Susanna a lot of embarrassingly dumb questions, but somehow she never (read: rarely) makes fun of me.

So there you have it, 5 fails balanced out with 5 wins. As we move on with our transition, I hope to minimize the fails. Hopefully through experience we will be able to move forward with less mistakes than before.

But if not, at least I know that you can still succeed even while making blundering mistakes.

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