If you’ve ever shown one of your out-of-town friends a good time in Milwaukee, like taking a trip on the Pedal Tavern or renting a Duffy Boat, chances are Derek Collins had something to do with it. He’s a serial entrepreneur and one of Milwaukee’s biggest tourism advocates.
For over 15 years now, he’s been building businesses that foster connection and community while showing everyone what Milwaukee’s all about. And while it comes with its challenges, the setbacks have taught him just as much as the wins, allowing him to keep improving his existing ventures and finding inspiration for his next ones.
Let’s dive in.
What is your background?
Raised in Wauwatosa and moved back to Wauwatosa to raise my family.
Any stories from your youth that define your path?
As a kid, I was always competitive in sports. Business isn’t that different. People call it luck, but luck is usually just the byproduct of relentless work. The more iterations you put in, the more opportunities you create.
Where did you study?
UW-Milwaukee. Bachelor of Business
What do you do for work now?
I spend my time building businesses that get people out into the real world. I’m the owner or co-owner of Milwaukee Pedal Tavern, Brew City Kayak, Paddle Tavern, Conflux Holdings, Milwaukee By Bike, The Cooperage, Milwaukee Duffy Boat Rentals, and Driftwood Sauna Club.
Can you talk a little bit about your career journey?
Milwaukee Pedal Tavern was the beginning, not the destination. Since 2010, we’ve continuously expanded by introducing new experiences, investing in new assets, and challenging conventional ideas. The goal is simple: give people a reason to come back every year. Successes fuel growth. Failures fuel better ideas.
Can you talk more about your community involvement or volunteer experience?
We work with a variety of non-profits and help with their silent auctions. Secondly, I am an Alderperson with Wauwatosa.
What are some ways you have impacted the community in your line of work?
The biggest impact has been creating demand for local businesses. Every customer we bring into Milwaukee has the potential to support a hotel, brewery, restaurant, or small business. Tourism is an economic engine, and we’re building experiences that keep that engine running. Watching Milwaukee grow has been incredibly rewarding, and our team is excited to keep pushing that momentum forward.
What do you like about living in Milwaukee?
Milwaukee is an incredibly underrated city. It has an unusual combination of accessibility, affordability, and quality of life that’s difficult to replicate. I love taking a Duffy boat down the river, biking the trail systems, and the “Smallwaukee” feel where the city is large enough to be dynamic but small enough that people still know each other. Great schools, parks with my kids, the zoo, Bradford Beach, golf, outstanding restaurants, nightlife, the Brewers, the Bucks, local music, volleyball, pickleball, skiing, Summerfest, the State Fair, easy access to lakes, and a commute that rarely feels like a major city. I could probably list another 50 reasons. That’s exactly why I’ve chosen to keep building businesses and investing here.
What do you want to see for Milwaukee’s future?
There are two projects I’d love to see happen in Milwaukee:
1. A Pedestrian and Bicycle Bridge connecting E. Summerfest Place at Trestle Park to Florida Street. It would finally create a seamless connection between the Third Ward and the Harbor District, making it easier for people to walk and bike while unlocking significant opportunities for new development and investment.
2. A More Navigable River System. Milwaukee’s rivers are one of our greatest assets, and we should treat them like a transportation network, not just a scenic backdrop. Imagine being able to boat from downtown to American Family Field / Wauwatosa, north to Mequon, or south along the Kinnickinnic River. Expanding access would create new recreation, tourism, and economic opportunities throughout the area.
Anything else we should know about you, your job, community involvement, or life in general?
When I’m not building businesses, I’m chasing around my greatest adventure: my wife, Sarah, and our two awesome kids, ages 3 and 6. They happily consume every spare minute I have, and I wouldn’t have it any other way.