“Starting from zero followers is freeing.”

The TFP Q&A with Tim Cigelske, marketing VP and media entrepreneur

I met Tim Cigelske way back when. He was writing The Beer Runner blog at Draft Magazine, chronicling his efforts to drink a beer and run a mile every day, and generally celebrate the combination of two subcultures. The entire project felt ahead of its time, and it was fun to watch.

A decade and a half later, Tim is still doing plenty, although there’s less time for running and beer drinking. He spends his days as a vice president of communications and marketing at a private high school in Milwaukee while also running the job board Big Shoes Network and the fledgling parenting community North Shore Family Adventures.

We talked about the pivot from journalism to marketing, how AI can supercharge a startup, and finding inspiration at the trampoline park.

Three Point Four Media: One thing I’ve always really admired about you is that you just kind of do stuff. (Sorry Ty.) As someone who also aspires to do things, in my professional life and with side projects, you’re inspiring. Is that intentional or does it just happen?

Tim Cigelske: I haven’t thought about it in those terms, but I love that description of just doing things. I think that’s true of a lot of people who go into journalism because you never get bored. I have a lot of curiosity and want to see what else is out there.

My first full-time journalism gig was at a young adult weekly. I had tremendous freedom and creativity to create the type of beat I wanted. One of the most fun things I did was something called “A Day on the Job.” I tagged along with someone who was doing something interesting: a garbage collector, a construction worker who was working on a historic city hall restoration, stuff like that. Once you start doing those things, you don’t want to stop. You want to keep trying new things. Now you see a lot of journalists experimenting with entrepreneurship and starting new things with new technology. It’s in our DNA and training to explore.

What led you out of journalism?

The same thing that led a lot of people out of journalism: our department got cut. I had a mortgage, a wife, and a kid, and the whole department just got cut. We weren’t the magic bullet to gain young readers and defeat Craigslist. I continued to freelance, but I was looking for another full time job, something with stability, and that’s what led me into marketing. The first time I was prepping for an interview, I was thinking “who’s going to want me? I don’t know how to write a press release.” A mentor who worked in PR told me I was crazy, that of course they wanted journalists because we knew how to do storytelling.

Back in the Draft days, you were so good at the promotional side of journalism. I imagine that translated well to a communications job at Marquette University.

At the time, Twitter was the growing medium, and the one where I was most comfortable. I started using it as a journalistic tool to find sources and story ideas. It made my life easier. I knew if I created a niche that no one was talking about, people would follow. I was flabbergasted that no one was talking about craft beer and running. It’s funny: things really took off when I stopped posting under my own name and started posting under The Beer Runner. People could grasp that because it was simple and made sense. They knew what beer running was. They didn’t know anything about Tim Cigelske who talks about beer and running.

What does your day-to-day look like now?

I’m in private high school, Jesuit education, doing things that are similar to what I did for 13 years at Marquette University: social media, digital media, and email marketing.

I also run a Midwest-based communication job board, which sounds very niche but it’s actually been around forever. It’s where I found my last job. I know the owners, and I believe in the mission. When they decided to retire, I ended up taking it over with a partner of mine. It’s only been six months but we’ve redesigned the website, added to the marking plan, and are making a few other tweaks. I knew going back to my journalism roots that I wanted to tell stories of how people ended up in their careers, what advice they had, that kind of thing.

“I hate paywalling stuff, but that seems to be the only way to get people to pull out their credit card.”

Right around the time I took over the job board, I was at a trampoline park with my son. He can stay there for hours, and I’d done all the work I needed to do and all the scrolling I could stand. I started to think about all the parenting activity sites and how there was nothing in our neighborhood. I decided to start one. We get about 30,000 views a month and it’s growing quickly. It’s interesting to start something from the ground up in 2025. It’s a pretty mature market, and you’re starting from nothing with some established players.

It’s amazing to have a stable day job that I really love, and then things that I can experiment with and learn from on the side that inform where we are going next.

How do you think about starting something from scratch now?

Starting from zero followers is freeing. It gives you more of a drive to create, to experiment, to try new things, and to see what’s working. That in turn helps you on your mature accounts. It humbles you, but it shows you that you have to put in the work. Feed the beast. Be consistent. Keep going.

Do you use AI in your work?

All the time. The thing that gets the most visibility on the site is stuff like “What are Trick or Treat hours?” We set a record this weekend with that post. But going out and finding every community’s Trick or Treat hours would take forever. I used deep research. (I prefer Claude.)

Originally, I was just doing it for, like, one community’s July 4th fireworks times. I realized I could compile so much more with AI and do every community in the area. Some local media do it, too, but we can do it quicker and better. We have to check to make sure it’s correct, but it’s so valuable for local families. It’s not the highest form of journalism, but it is a community service. Using AI for stuff like that helps me balance my time. I can spend most of my creative energy writing a voice-y, personalized newsletter. It creates a flywheel effect where someone comes for the Trick or Treat hours, then leaves their email address, gets our newsletter, and we deepen the relationship with them that way.

You also need to understand the community and its needs to think about the types of information that could be helpful. Then you can set AI out to gather it together.

Now my eyes are open for things that people might find interesting. Do they have access to that information? Is it easy to access? Where I live, county fairs are a big thing. The number one post from the whole year is how to get in free to the state fair. Compiling easy ways to get in there, get discounts, and that kind of thing does enormously well. So then I did it for all the county fairs in the area. I saw a billboard for a county fair I’d never heard of, looked it up, and found out it was the oldest county fair around. I did a guide to when they’re open, what their admission prices are, and when their deals are. That was one of the most popular posts for August. Two days before, I had never even heard of this fair. And then it was driving all kinds of traffic on the site. You have to keep your eyes open, and then use AI to augment your efforts.

I wouldn’t want to do this project if it was always this drudgery of looking things up constantly. I did enough of that as an intern. But having AI do so much of the manual work frees me up to do other thoughtfully curated and more creative work that benefits the community in different ways.