This interview is part of the cover feature from the BizTimes Milwaukee 30th anniversary issue, published March 17, 2025. For more information and to see interviews from other southeastern Wisconsin leaders, visit biztimes.com/30-people.
Molly Dill
Managing director
gener8tor | Madison, Milwaukee
Age: 37
Molly Dill leads the Milwaukee and Madison investment accelerators for startup accelerator network gener8tor. She joined the organization in 2019 as director of gBETA Milwaukee, a seven-week pre-accelerator program for early-stage startups, and was then promoted to managing director in 2021. Dill’s entry into the world of startups and venture capital followed an award-winning journalism career with BizTimes Milwaukee, where she most recently served as managing editor while also reporting on startups, technology and financial services.
What needs to change in Milwaukee and southeastern Wisconsin over the next 30 years?
“I would like to see a more cohesive and connected city via a significant expansion in public transit. Having grown up in the Chicago area where taking the train or bus was usually more convenient than driving, it still seems weird to me that we have to drive everywhere in Milwaukee. This reduces accessibility for those who aren't able to drive and further separates neighborhoods. And as someone who regularly commutes to Madison, it would be so fantastic to have a train connection between the cities.”
What do you hope to accomplish over the next 30 years?
“I hope I can make a lasting impact on the startup ecosystem in Wisconsin – maybe I can reach 250 startups mentored? In conjunction with that, I also hope I can convince at least one new person per year to start angel investing so we can collectively support these young businesses and help them become successful beyond our borders. Down the road, I'd like to do some angel investing myself. And another item on my bucket list is to write a book.”
What’s your pitch to the next generation to make Milwaukee and southeastern Wisconsin home for the next 30 years?
“Milwaukee is the best kept secret in the U.S. It has all the same amenities, arts and culture as larger cities without the congestion, and it's close to some fantastic nature experiences, so you can get the best of both worlds. A lot of people are surprised when I tell them Milwaukee has beaches, or that it hosts the World's Largest Music Festival. Part of the reason I adopted Wisconsin as my home is also the ‘Midwest Nice’ attitude and the delicious food.”
