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What Do SEO And Rome Have In Common? Startup Founder Thomas Nolan Explains

Thomas Nolan is proof that the reputation Midwesterners have of being a down-to-earth, straight talking, hard working bunch is much deserved. (Full disclosure: I hail from Illinois and undoubtedly carry some bias here.) He’s built a digital marketing agency from scratch, in the face of a bleak economy awaiting recent college grads and SEO clients that want results yesterday.






Windy City Digital is full-service digital marketing agency based in Chicago. Startup Founder, Thomas Nolan has built the company to represent some of the more familiar athletes and institutions in the city, project by project. That doesn’t stop him from given credit where credit is due (Mom, of course). Thomas tells us more:


What’s your company about? What do you do? Who are your customers?

Windy City Digital is a complete digital marketing agency. We offer website design/dev, video production, graphic design, and SEO/CRO services. We have clients of all sizes and industries – from startups to Fortune 500 companies to professional athletes.


What’s the greatest thing about your company/website? Why is it better than the competition?

The aspect of our website that separates it from the competition is our free tools section. We currently offer 3 free tools to developers, freelancers, and anyone who needs them really – Contact Form Generator, White Label Invoice Creator, and SEO Page word count tool. But we are always adding more free tools.


How’d you come up with the name for your company?

We wanted to incorporate something related to Chicago, so what better than the famous nickname – Windy City. Then we added the fact that we focus on digital services and threw that into the mix to create WCD.




 WCD’s work with Bears great Lance Briggs



What was your first computer? How old were you when you first got on the world wide web?

Hah, I was probably 7 years old when I first got my own computer. It was my dad’s old work computer, and I decided I wanted to take it apart to see how it all functioned. Once it didn’t work anymore, it became mine. Sure enough, a few days later I got it up and running again.


What time do you usually start work each day? How many hours a day do you usually work?

Depends on the client I’m working for at the time. Being recently out of college, I have no problem pulling all nighters. I’m usually working by 8:30 and check out around 5:30-6:00, but some nights I work well into the night.


When’s the last time you went on vacation and where did you go?

My last official vacation was in Australia last July. I went and volunteered at a wildlife sanctuary building habitats for endangered animals. I plan on going again next year to pick up where I left off – awesome experience.


What’s the very first thing you do at work every day?

Email… sounds pretty obvious, but I pretty much live in my inbox. I then usually check out my checklist for what I have going on in the day.


When do your best ideas come to you? In bed in the morning? During dinner? On your third beer?

Oddly enough, usually my ideas come to me while I’m in the shower. For some reason I can just think without interruptions, and I’ve come up with some of my best ideas in there.



944597_10201595045860301_387044201_nThomas Nolan



How many people did you start the company with and how many people work for you now?

I started the company with just myself. My friend quickly got on board and helped with video production. Soon after, my brother and dad got involved as well. We work with one foreign developer as well – from the Ukraine. He has been an invaluable asset to our development team.


A lot of people have big ideas. What gave you the confidence to actually go after yours?

Not to get all emotional, but my mom definitely gave me the confidence. She passed away when I was 19 years old, and I’ve based the past few years on making her proud and pursuing what I love. I ultimately want to get enough cash flow to where I can help non-profits with their websites and web-presence throughout the year completely pro bono.


Remember the early days of starting up? Describe the struggles you went through.

As common as the cliche is that word travels fast, I think the hardest part was getting the word out about my company. Word of mouth only helps so much, and you quickly find that cold calling is very inefficient. Generating quality leads was definitely the biggest struggle – but then deciding what to actually charge without scaring the client away was another huge problem. Certain projects would be out of my scope of development, so finding someone to contract it out to for assistance and vetting those individuals was also a challenge.


How do you handle frustration? What has been your biggest professional frustration?

The biggest professional frustration I have is with SEO clients. They expect to be on page one within a week. In reality, it could take months, but they aren’t willing to accept that. In order to handle it, I usually go with the cliche phrase about how Rome wasn’t built in a day. It’s cliche, but the analogy is completely true. SEO takes time and effort to be effective, so clients usually back off a bit after that “rehearsed speech.”


What’s your office environment like? Do you listen to music? Watch movies? Play video games?

I love a laid back environment. Google has definitely been an inspiration as far as how I want my work environment to be setup. Comfy chairs, exercise balls, music… the works. I want my employees to actually WANT to get out of bed and come into work in the morning, and I want my clients to know that they’re working with a very down-to-earth company.




WCD’s logo design for The Asian-Pacific American Coalition



How do you picture your company in 5 years?

I’m hoping to expand into the 7-12 employee range within the next two years and the 15+ in the next five. As I mentioned above, I hope to be getting enough cash-flow from clients that I can start helping non-profits on a regular basis completely pro bono. I would also like to be helping more and more startups. Right now, I can only do a few a year because they don’t have the money for websites and SEO, so we take hits by taking them on. I would like to move my office (which is my basement) into an actual office space in the heart of Chicago.


Who or what inspires YOU? Role models? Quotes? Running? Video games? Snack food?

Steve Jobs definitely inspires me as far as design. I love the minimalistic approach to everything and clients seem to love to keep it simple as well. But, I get inspiration from everywhere honestly. It is the little everyday things that catch my eye and turn into something great.


How’d you fund this venture? VC? Self-funding? Crowdfunded?

It was all completely self-funded. The nice thing about working out of your basement to start in my industry is that as long as you have a computer and a website you’re good to go.


Got any great bootstrapping tips for the lean startups out there?

Considering I’m still in the very infancy of my startup, I don’t really have any tips.


What other advice do you have for other entrepreneurs struggling to get started?

The only thing I really can say is just don’t give up. Again, sounds like something everyone will say, but believe it or not there are a lot of people who are going to tell you “it’s not going to work” or “you’re wasting your time.” As long as your willing to put forth the effort, good things will come.


What would you do if you had a year off and $500,000 to spend (on something other than work)?

Travel. No doubt. After going to Australia, I want to see more of the world, and I really want to go backpack through Europe. That wouldn’t really put me anywhere near 500k though, and I would probably invest some of that in other startups.


Do you consider yourself a successful entrepreneur? If not, what’ll make you feel successful?

In my opinion, as long as I’m profitable, I’m successful. So, yes, I believe I am successful – but success is one of those things that never ends. You can always do better, and you need to continue to expand.


Top 5 websites you couldn’t live without and why?

  1. Google – infinite access to information at my fingertips…
  2. Netflix – I am definitely one of those people who watches one episode and two days later I finish the whole series
  3. – I love my email. For more than business. I keep in touch with my friends from around the world.
  4. Basecamp – All of my business is funneled and organized through Basecamp
  5. Woot – I need my daily deals… spend money on stupid things…


Top 5 mobile apps you’re in love with and why?

Unfortunately, I have a Windows Phone, so apps are far and few between… But I always have a Woot app, as mentioned above… need my daily deals. SnapChat… I’m not proud of this one, but my friends love it and it’s always good for a laugh. Premier League Soccer / ESPN Hub – I need my sports fix throughout the day and Arsenal updates… Shazam is another app I cannot live without. More than half of my iTunes collection wouldn’t exist without me Shazaming songs on the radio. The final app would definitely be Weather Channel. Living in Chicago, you never know what you’re going to wake up to…


What is your music streaming player of choice, and what are you listening to right now?

Pandora is definitely my music streaming choice, and country music for the win. I listen to just about everything, but I love country music.


Number 1 country you’ve always wanted to visit but haven’t yet? (And why that country?)

Greece. I think it is the most beautiful country and has so much to see. I’m not in the least bit Greek, but studying the area and learning about it is just a tease compared to actually going. Soon…


Three people (other than you) we should follow on Twitter and why?

I honestly don’t spend a whole lot of time on Twitter. The time I do spend on it is looking for a laugh. So I would recommend:

  1. The Dark Lord (Voldemort)
  2. First World Problems (favorite meme)
  3. Bad Luck Brian (second favorite meme)


Please share some specific numbers (funding, revenue, visitors) that highlight your growth.

Right now I get about 1500 visitors to my site per month. As far as conversion rate that’s probably at about 1%. Revenue each month is entirely based on the size of the projects for the month but are anywhere between 5k and 25k.


Where else should our readers find you online?


Photo Credits

Windy City Digital | built in chicago | DaniDF1995

Author : Keith Liles

Keith Liles is a freelance writer who loves travel, music, wine, hiking, poetry, and just about everything. He practices saying "yes" to life vigorously, rehearsing for the phone call when he's asked to tour with Bruce Springsteen and the E Street Band. Follow Keith on Twitter @KPLiles.

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