Today is an important milestone in the history of OnMilwaukee. It was on this day, Sept. 1, that I flipped the switch and launched our website in 1998.

"Flipping the switch” sounds more grandiose than it was. Really, I changed the name of a file to index.html and using FTP via a dialup modem, I uploaded it to a server from my apartment on the East Side. Shortly after midnight, a wide-eyed ambitious 24-year-old me took a deep breath and waited. Then I went to bed and woke up early to see if everything still worked. Mostly, it did.

That was 25 years ago today.

I’ve actually had some mixed emotions in writing this retrospective piece, because this anniversary is loaded with so many feelings. I’ve spent the last week looking through dusty photographs and mementos, as well as searching old hard drives for files so ancient they can no longer be opened by my current MacBook Pro. I reflected on the good times and the great experiences, as well as the challenging moments over the years. I’ve wondered if the decisions I made at age 23 and 24 that have shaped half of my entire life and almost all of my career, were the right ones. I’ve come to the conclusion that, like everything, they were and they weren’t. But I wouldn’t trade them for anything.

To properly tell our origin story, I have to go back even further than 25 years. I grew up in Milwaukee, until my family moved to the East Coast the summer before eighth grade. I was stubborn then, too. I dreamed of a time when I could return to Wisconsin, and I spent summers with my grandparents back home. Even after high school, I pondered coming back here for college, but I opted for George Washington University in Washington, D.C., so I could fully immerse myself in my interests, which mainly consisted of journalism and politics.

I soaked it all in, writing and editing for my college newspaper and the Washington Bureau of the Dallas Morning News, taking internships on Capitol Hill and the White House. During summers, I interned in Milwaukee at Johnson Controls' corporate communications department. I tried and failed to secure an internship at the Milwaukee Sentinel, where my father excelled as a columnist in the early ‘70s. At that point, I figured I’d pivot to public relations, which I was told was more lucrative.

It was at that point I walked into a computer lab at GW to work on my resume when I saw the prototype of the World Wide Web. The Internet definitely existed before 1994, but it was text based when I arrived to college in 1992. Back then, the closest thing to the Web was a platform called Gopher, in which you could navigate around some sites via text menus. But I distinctly remember seeing an application called Mosaic, the predecessor to Netscape, and wondering what this thing was. I figured it out, and by the end of college, Yahoo was a thing, and I wanted in.

I spent my down time from job searching in spring of 1996 by teaching myself a little HTML, and I had a very basic and tacky website soon after to distribute my resume (imagine animated gifs of dancing monkeys and such). It was nonetheless impressive enough to prospective employers that when I had an interview for Milwaukee-based public relations firm Cramer-Krasselt in a conference room at the White House (that unpaid internship had a few perks), I landed myself an entry-level job at the agency. Burned out from the DC scene, I took my first car, a leased Toyota Tercel without air conditioning or a radio, and drove cross-country back to Milwaukee. I had arrived.

And though I was yet to even start my first salaried job, I was already thinking about OnMilwaukee. Even in college, my friends wondered why I spoke so highly of Brew City, why I wore a backwards Brewers hat all the time, usually paired with a ratty old Lakefront Brewery T-shirt way. I wanted to explain what made Milwaukee so great.

That feeling only intensified in 1996 and 1997, when I switched to another PR job in Walker’s Point.

By then, I was filled with a restlessness that never really went away. Even at C-K, I figured out how to run an Ethernet cable from the mail room to my tiny cubicle, so I was the only employee, an Assistant Account Executive, with access to the Internet. I pondered creating a newspaper or magazine featuring a Milwaukee that I was witnessing changing in real-time. But how? I looked at the costs of printing a newspaper and compared that with the nearly free expense of building a website. I bounced the idea off everyone I knew. Most of them didn’t get it, but by 1998, I was starting to think the Web was the way to go, whether as a hobby or as a job.

If you’re old enough, think about what Milwaukee was like back then. The gorgeous Milwaukee Art Museum expansion had yet to be built. Miller Park was hardly a sure thing while County Stadium was practically being held together by pine tar. The Hoan Bridge was still the bridge to nowhere; not that it mattered, hipsters hadn’t really discovered Bay View. I lived with roommates on the East Side. New bars like the Nomad were among the few hot spots that challenged Brady Street’s reputation of “Shady Street.” And forget about the Third Ward. It sat devoid of much action, the Milwaukee Ale House opening in fall of 1997 (fun fact: I liked their logo so much, I emulated the font in OnMilwaukee’s first logo).

And yet, I saw something changing. A city that was coming into its own, struggling to shed its reputation as a little rip off of Chicago, where our best and brightest would wind up after suffering through entry-level jobs in Milwaukee. In fact, in spring of 1998, that almost happened to me. My employer asked me to move to to Rosemont, Illinois. I was faced with a decision, to put up or shut up. Should I move to O’Hare to continue to work in media relations for a telecommunications, or should I build an online city guide? While I pondered that decision, I sharpened my web design skills, and finally on April 7, 1998, I quit my job and started OnMilwaukee.com for real, although at that point, it didn’t have a name.

The funny thing is that as much as I keep old mementos of my life, I don’t have a ton from those very first few months. I have the memories, of course. I remember sitting around my dining room table, brainstorming names for the website. That’s actually one of my regrets: while OnMilwaukee.com is and was a great name, it created a lot of brand confusion then and even now. People frequently still think we’re “OnWisconsin” or “Online Milwaukee” or “Milwaukee Magazine” or even “Milwaukee.com.” We’ve probably sent those sites a lot of traffic over the years.

I also have very few photos of the early days of OnMilwaukee. That makes sense, because digital cameras were terrible and expensive back then, and of course, none of us had cameras on our cell phones. I wish I had more physical evidence.

Actually, I was a decent at journaling back then, and yet, the closest mentions of OnMilwaukee’s launch came two months later on Nov. 3, 1998:

“I’m a full-time freelancer and hopefully on the verge of my first million with OnMilwaukee.com. Eventually I’ll get around to describing it all, but not now. I’m kinda sleepy, so I think I’ll just lay around and listen to the new Beck album I bought today.”

And then again on Nov. 17, 1998:

“I'm very anxious to see if OnMilwaukee.com does anything. Our commercials start on Monday. They're pretty amusing. We'll see what kind of response we get.”

Sorry that’s all I have. Anyway, back to the history.

Of course, I definitely can’t take all the credit. I didn’t do this all by myself, and I still don’t. An engineer I worked with named Jon Krouse joined the business shortly after April of 1998, and he stayed with the company until 2004. That same summer, I recruited another PR person in my orbit, Jeff Sherman, over beers at the Nomad, and he remained my business partner until 2020. About two years into our journey, via mutual friends, I met our investors, Joe Tate and Dennis DeVetter, who still remain owners. And I recruited my most recent business partner, Glen Ponczak, one of my first bosses at Johnson Controls and my only real professional mentor, in 2020.

So, the time spent between April 7 and Sept. 1, 1998, was a blurry whirlwind. I say I was self-employed, but basically that meant freelancing for anyone and everyone by day and working on OnMilwaukee at night. Jon and Jeff quit their day jobs a while after I did, so it was an unusual and solitary existence for a 23-year-old who suddenly went from a low-paying job to a no-paying job. Glen, still at Johnson Controls, propped me up with contract projects of all kinds. He told me years later that he saw a spark in Young Andy, and apparently I asked him to partner with me and leave his very prestigious career. Even though it took him 22 years to dive in fully, I’m glad he did.

Joe and Dennis also took a chance with us. In our first meeting, Joe asked if we had a business plan. I told him we did, but the Internet was changing so quickly that we couldn’t keep it current. “Good,” he said. “That means you’re agile.” A week later, we had $500,000 sitting in our savings account. It might as well have been $50 million, becasue it was more money than I had ever seen in my life. And yet, I was so naive to think that half a million bucks would take us to where we needed to be. After all, we unknowingly launched OnMilwaukee four days before Google, although within a year they raised $25 million. Mark Zuckerberg was only a freshman at Harvard in 1998, but while he was palling around with the Winklevoss twins, he would launch The Facebook in 2004 with much more impressive funding than I could’ve ever imagined. In retrospect, we were extremely underfunded, and I was chagrined that my company raised my salary from $0 to $20,000 a year. The dot com millionaire dream was going painfully slowly.

Which is not to say I’m regretful of how we started. We bootstrapped it. I didn’t ask my parents or anyone else for money. I ate ramen noodles while meeting with everyone in town who would let me buy them a coffee. We were so grassroots, and I credit that for our early traction. Even though Milwaukee didn’t understand the Internet – so many people told me it was just a fad – readers, partners and advertisers stepped up. We ran the business like a brick and mortar and not a dot com darling. I think that set us apart from the others who tried and failed to do something similar. My biggest regret is that we didn't think bigger. It took us years to come up with a scalable model that was diverse enough to include different kinds of revenue streams.

Our original model was actually pretty silly, in retrospect. My first vision of OnMilwaukee was an enhanced Yellow Pages, of sorts. We would list all the restaurants, bars, theaters and shops in town for $250/year. Obviously, the reality quickly sunk in that we wouldn’t be a very comprehensive (or lucrative) city guide if we only listed the businesses who paid to be included, which weren’t many, so we quickly pivoted. I fell back on my journalism background and started writing feature stories. Frankly, they weren’t very good, but in 1998, we didn’t have any online competition.

People started visiting the site right away. First a few hundred, then a few thousand. By the time we finally secured our funding, we were seeing legit traffic, even though all the content was being written by an unpaid Marquette intern named Paul, Jeff and me, and I was updating the site by hand every day. The investors came along at just the right time, because I was burning out and I was only 26.

That’s when things changed. We took our money and hired programmers, salespeople, designers, and most importantly, great journalists. Two of our first employees are still with us: Bobby Tanzilo and Molly Snyder. Employees like Jason McDowell and Carolynn Buser have surpassed 15 years with the company and others are not far behind. Our youngest employees weren't even born in 1998, and honestly, I love our mix of savvy, industry veterans and new, fresh enthusiasm.

"Having worked for nearly a decade at Schwartz Bookshops, which at that point was nearly 75 years old, I was pretty sure I was quitting a secure job for this passing fad of an internet," recalls Tanzilo. "But 23 years later, here we are."

Others have moved on to further their careers elsewhere, and I’m still close with many of the more than 100 people who have worked for OnMilwaukee since 1998. At least three have passed: two freelancers and the wonderful Tim Cuprisin. And yet, I believe that our current group is the strongest it’s ever been. I’m honored and privileged to work with this amazing team.

Of course, not every day has been spectacular. We’ve weathered a few recessions and a global pandemic. We’ve innovated and stayed ahead of the curve. We’ve had profitable years and months that felt pretty bleak. It’s hard to be a local independent media company, but we’ve not just hung in there, we’ve thrived. Today is a day to celebrate.

You may know us for our 61,770 articles. You may know us for our events. You may know us for our digital agency. You may know us from our best-in-market social media presence. Or maybe you know us personally, because each of the 15 of us live, work and play in Milwaukee.

"OnMilwaukee is Milwaukee. The stories keep getting better and the company keeps growing in new directions," says Snyder. "And personally, it has provided me with so much more then a job: it's given me a life that I love."

Any way you slice it, we – and I – wouldn’t be here without those of you who are reading this right now. There are about 1 million of you visiting OnMilwaukee, in all its forms, each month. That is a staggering number to me.

We’ve really been celebrating this 25th anniversary all year, because even though Sept. 1 is “the day,” all of 1998 was an evolution. We’ve toasted our history at a few events in 2023, and there will be more. Speaking of toasting, very soon you’ll have a chance to drink our very own 25th anniversary beer, made specially by Explorium Brewpub. Seems like a good way honor a quarter century in Brew City.

I’ve been absolutely blessed for the countless experiences and opportunities that OnMilwaukee has granted me. Being an entrepreneur is harder than it looks … but on a day like today, it’s the greatest privilege I could imagine.

Happy birthday, OnMilwaukee.