I recently traveled to Milwaukee in partnership with the Wisconsin Economic Development Corporation. They hosted an intimate press trip of media figures and modern journalists to showcase the entrepreneurial community within the evolving city. It was an honor to be invited!


Milwaukee is very much evolving, especially within its entrepreneurial community. I’m excited to share the details with you!


Tune into this episode to hear…


  • What specific initiatives we saw in Milwaukee and what they taught us about fostering the economic development of a city
  • What this press trip taught me about my own business
  • The commonalities between all the entrepreneurial endeavors we say- entrepreneurs, you’ll want to take notes for this!
Tune in to episode 68 to hear about Leah's first press trip to Milwaukee, Wisconsin and what this trip taught her about her own business.
Podcast Episode  

Facebook Live Replay 

Transcript of Episode

Leah Gervais: Visionaries, Welcome back to the Your Biggest Vision show. I’m your host, Leah and for those of you that follow me on Instagram, you probably know that last week or two weeks ago I attended- I was in Milwaukee, I was traveling in Milwaukee and that’s because I was there in partnership with the Wisconsin Economic Development Corporation. 


They had an intimate group of journalists, media, personnel, etc. that were there to showcase and learn more about this very much evolving city and report on it on whatever platform that they have. So they asked to go because they know that my platforms are all about entrepreneurship and all about entrepreneurial communities, especially young entrepreneurs. I obviously have a brand called Urban 20 Something. And the irony is I don’t think really any of my clients are in their twenties, maybe a few, but obviously what I do, it goes across generations. That said, one of the things they really wanted me to learn about and see and talk about is how great of a city Milwaukee is for young entrepreneurs. And we’ll get to that in just a second. So what this consisted of was about three days of us being there and they had scheduled some really incredible tours, networking events in general for us to, to see as much of the city as we could and learn about it. 


And especially for me, they wanted to show me what the entrepreneurial community was like there. So I’ll just tell you a little bit about some of the things we saw in Milwaukee as well as some of the things we learned. And then I’m going to tell you three main takeaways I got from the trip. One was a takeaway from Milwaukee itself and what I learned about it, one was from press trips in general and what they might mean to you if you are an influencer, an entrepreneur, a blogger, anything of the sorts. And then the final one is some takeaways about entrepreneurship that I learned on this journey because I was lucky enough to spend three days seeing about, I don’t know, eight different entrepreneurial staples within a city. So I have this really unique and amazing opportunity to see kind of a through line from all of the things that these places have in common, which fosters entrepreneurship. 


And that’s what we are here for. So, here’s a little bit about what we did. Those of you who maybe haven’t been to Milwaukee or don’t know much about it, don’t worry. I didn’t know very much about it. I had never been before. It’s funny, they actually said it’s statistically shown that most of America knows very little about Milwaukee. I honestly, when I heard about Milwaukee, if someone would’ve said that, what I would’ve thought of were the Packers, cold winters, really good beer and really good cheese, that that would’ve been the first things that came to mind. And probably some college towns. I know that there’s quite a few colleges in Milwaukee, but I didn’t know anything about its entrepreneurial community and some of the new initiatives it has going on. And I clearly wasn’t alone, which is a reason why the Wisconsin Economic Development Corporation invested in this press trip so they could start spreading more of the word about the city and the cool things that it’s up to. 


So we were there a day before the trip actually started officially. And the tour actually started officially because I had to leave a day early because I’d fly to Italy, which is a conversation for another time. But the point is that I did about the first day on my own. I still did a lot of the things that they were going to do with us. I just needed to do them on my own because I wasn’t going to be there with the whole group. So while there, we saw things like the downtown historic third ward, which has been hugely renovated since the late eighties and up until then it was not a nice place. It was sort of like a red light district right in the middle of Milwaukee where it had started as that from when Milwaukee was just a port city, you know, like in the late 18 hundreds. 


So it’s really charming now. It has a lot of good food and fun places to go out, etc. We went down there, we walked on their new river walk, which was really pretty as well. It’s just sort of a walkway right near the river that goes through the middle of the city. Um, we went to, what my favorite part of the whole trip is this really amazing initiative called the Sherman Phoenix. And I’m actually doing a whole interview on my later podcasts in two weeks about this. But the Sherman Phoenix is an entrepreneurial hub in the part of Milwaukee called Sherman Park, which is a very racially segregated part of a racially segregated city. And it started about three years ago, I think after the fatal, a fatal shooting of police brutality in Sherman Park. And the community wanted to do something, obviously, productive after the tragedy that had happened. 


So they came together and they found an a bank that had been burnt down from the riots of that shooting and they renovated it and they turned it into an entrepreneurial community now where there’s lots of little shops within that building and they have entrepreneurial mentors and they’re really helping people in this community start and grow their businesses. And it’s called the Sherman Phoenix because it rose out of the ashes of this literally burnt down bank. Uh, so that was amazing. We also saw a coworking space called The Commons where they don’t only offer you coworking space, but they do trainings for entrepreneurs. They connect young talent and recent graduates and even kids in college to businesses throughout the Milwaukee area. And I’m trying to think if there’s anything else. We went to the art museum. We did a lot of stuff anyway, let me get to the point, but as you can see, there was a lot that we did while we were there and a lot of it was very related to entrepreneurship, which was super cool because I didn’t really know about the entrepreneurial community in Milwaukee. 


And the big takeaway that I got from the people that were really loving being entrepreneurs, there were people that had this entrepreneurial bone. They were excited about starting something that was their own. Um, and a lot of them were even from Milwaukee or from a nearby area, but they had kind of grown up assuming that if they wanted to start from business and really succeed, they’d either need to move to Chicago, which is about an hour or two away, or even New York. And so for them to now see that there is this wonderful community right there in Milwaukee that the city that they love and that they grew up in that’s closer to their family but also so much less expensive than Chicago and New York is really exciting. And one of my favorite parts of this is when we met some of the people from the city council’s office. Many of them weren’t from Milwaukee. They had moved there either from the east or the west coast. And they love the community. They loved how much everyone really band together, which I really felt that too. Everyone was clearly such a fan of this city. They liked just the community around it and how much everyone just valued sort of that Midwest mentality of hard work and respecting people and you know, being there for one another and just doing the right thing. And also a lot of them have stayed there for 10, 20, even 30 years, even now, originally having been from there. 


So without further ado, let’s go into some of the takeaways that I got from this incredible trip. The first big takeaway which I mentioned was about the city itself. And you know, I did just kind of cover some of that, but the big takeaways were that there is a huge entrepreneurial hub that’s very evident and the people there love their city. 


Now I love New York. You guys all know how much I’m obsessed with New York. And it’s a dream come true waking up here every single day. But one of the things New York really doesn’t have is a sense of unity. Of course, that’s sort of what makes New York, New York. And I wouldn’t necessarily change it, but you could feel in Milwaukee, everyone’s cheering for the Packers. Everyone is cheering for whatever their basketball team is… everyone’s cheering for the bucks, everyone is cheering for the sports teams. You know, everyone has this story of why they’re there and they’re really proud to be there and whether it’s they’re born and raised there and they love where they grew up and they have just have a lot of town pride or they moved there by choice and they’d never wanted to leave. It’s a very great place to live. 


You can live in a really great apartment for a very affordable price. There’s lots of room for young people to be there. There’s lots of colleges and there’s lots of sports. So it really does have this sense of unity where everyone’s sort of cheering on each other. New York, as you can guess, does not have that. Obviously with sports we don’t have that because even if you are from New York, you’re still divided. We have the Jets and the Giants. We have the Mets and the Yankees. We have the Nets and the Knicks. We have so many different sports teams, even within New York. And most people that live here aren’t even from New York. Most people are from California or New England or Florida or whatever. So it is just a total hodgepodge. And that’s just sports. Even like socially it is not that we’re all in it together kind of place. 


It’s pretty competitive and it’s pretty cut throat. And some people thrive off of that like I do. But it is not for everyone. And I will say that I often do crave that sense of community that I really found that Milwaukee had. And it seemed like everyone was really cheering each other on, especially with their careers. And it seemed to be a really welcoming place if you were an entrepreneur because people just really want to help you and they really want to help each other. So it’s an exciting time to be there. And if I were graduating college again, then it’s a place I would look to move to just because of all the opportunity that’s there and the affordability of being there and the proximity to Chicago makes it really easy to travel in and out. You know? It’s not like in the middle of nowhere or anything like that at all. 


So I learned that Milwaukee is a very prideful town in a good way and the town is really doing a lot to expand and make the best of it. We did talk tour the uh, Fiserv, I think is how you pronounce it, Fiserv Forum, which is their brand new basketball stadium and it was commissioned by Marc Lasry and it was incredible. And his son was the one that showed us the whole tour and it was amazing to see how even just around the stadium they had built several new restaurants and new bars that had tons of outdoor space. Uh, just so that when people are there watching the games, even if they’re not in the stadium, they’re still part of that experience. There was all glass windows within the stadium, so you can always see out and looking in from the around surrounding areas there were tons of sports TVs and places you could just walk around. 


It was very communal and that’s pretty new. And there was even some upheaval about that being built to begin with because it was an expensive project. But they’re really seeing how it’s bringing the community together. There also is a part of the city that is near the lake shore brewery that I was told up until a little bit ago, a few years ago, you couldn’t even go over there. And they’re really trying to break that down and make it more communicative. So it’s a great community and everyone is really, really supportive of one another. 


Some other takeaways I had about the press trip in general. This is not specific to Milwaukee, but from my perspective as a business owner, you know, it’s really incredible to see how you can start. Like in my situation, I started my now business, my now multi six figure business as a blog. Uh, and that blog has turned into a place where I can now actually promote the economic development of a city in the United States. And that is really gratifying to me and something I’m really proud of. Um, and it’s not something I would’ve known that I would’ve had the ability to do when I started out. So I also was really reflecting during this about what it means to be an entrepreneur in this modern day. And I also talked to a good friend and a former client of mine, Danielle, some of you guys might know her, she has been on this podcast before and she lives in Bali full time and she’s a travel influencer and she said the same thing. She has said how people like these departments of tourism of countries will fly in entrepreneurs, influencers, content creators, Instagrammers where they used to fly in journalists or newspaper writers or authors and things like that. 


So remember that if you are starting a business and if you are putting something out there and you’re starting a movement and you have a message, you never know what you’re going to be able to do with that. So that’s why it’s so important to really care about your message, but not be attached to the how all the time of how you’re going to make this work. I have always, always wanted to promote entrepreneurship that showed up in different ways for a while. I’ve just talked a lot about side hustling. Now I can talk more about building six figure businesses and now I do more things with brands than I used to. You know, things have grown, but my true passion is always the power of entrepreneurship, both on a personal level for society, etc. That’s what I’ve always loved. And now being able to share the progress of a city with my audience based on that message shows that there is a need for that message and there is a need for entrepreneurs and there is a need for people that have a lot of vision and mission for what they want things to be like. 


So if you are in the newer stages of entrepreneurship, don’t hold yourself back and feel like, you know, it’s scary to put yourself out there or you’re not sure how things are gonna work out. This isn’t about you. If you care about a mission and you care about a message, then you should put it out there because you’re going to help other people. Maybe like, I dunno, a major U.S. city, like I was able to in ways that you’re not going to imagine, but you certainly won’t get to do that and you won’t get to spread that message and you won’t get to help people if you’re constantly holding yourself back. So that was a big lesson for me as well. 


And then the final lesson I want to talk about over this trip is just entrepreneurship in general. So as I mentioned, we went to the Sherman Phoenix, which is an incredible entrepreneurial hub in a neighborhood that has experienced a lot of tragedy recently. We went to a place called the Commons, which is a coworking space, but also a training space and connecting space for entrepreneurs and businesses alike. We went to the art museum, we went to meet the son of this billionaire entrepreneur who was able to commission a new basketball stadium. So lots of entrepreneurship in different forms, right? We have low income, we have a billionaire entrepreneur, we have students, we have people that are really seasoned in it. We have things with different missions but they all have this common thread of people starting something on their own, going through the challenges that come with that and coming out on the other side or learning how to deal with the challenges rather and as you can see, because I was able to tour four or five of these type places in 48 hours, community is key. 


There is a reason that there is a coworking space for this or a hub for this or a place where there’s mentors or a place they’re giving tours. It’s because entrepreneurship only really works and you can really only succeed if you’re not going at it alone. Do you have mentors? Are you in a mastermind? Do you belong to a coworking space? Are you learning from people that have done what you wanted to do? Are you actually helping other people? If you can. I’m just trying to think of the exact examples I saw from these places, but the point is they are there for a reason. They’re there because you need the infrastructure, an entrepreneur to support you. You can’t do it alone. And I think doing it alone is where a lot of people really get messed up, really talk themselves out of things and they wonder why things don’t really go the way they want to. 


And it’s because they’re carrying this burden on their own. So let’s take a hint from a city that is evolving quite nicely and quite impressively that you aren’t meant to do things alone. There should be people in your corner, you should have people to ask how to do things and you can do whatever entrepreneurial endeavor you have your heart set on, you can do it. There’s nothing you can’t do and you will blow your mind with the things you accomplish if you get started and you have the right support and infrastructure in place to help you in making it happen. 


So those are my takeaways from my trip to Milwaukee. I hope you guys enjoyed this and if you have any questions about the trip, let me know. I’m very excited to share  next week or, yeah, I think it’s next week. The interview actually might be later this week. 


The interview with the founder, two of the founders of the Sherman Phoenix Initiative. There’s also some reviews on my website of the hotel we stayed in as well as just some travel guide of the city in general. Please feel free to reach out to me and thank you again to the Wisconsin Economic Development Corporation for sponsoring us on this incredible trip. I learned so much about the power of entrepreneurship, about Milwaukee, about the two together, and I’m really excited to have shared everything that I learned today with you guys. I hope you have an amazing week and I hope that this podcast episode, I know I kind of covered a few different bases here. You know my takeaways as a business owner, my takeaways of Milwaukee, my takeaways of entrepreneurship, it might feel a little scattered, but I hope you can pull out whatever inspires you most right now and take action from it. 


Does that mean you’re going to start researching if Milwaukee would be a good city for you to live in because you’re an entrepreneur and you are sick of paying so much for wherever you live? Does that mean that you are going to start being more open minded about your own business as an entrepreneur because you don’t know how you’ll be able to send your message later on, but you know you’re never going to find out if you don’t try? Does it mean that you are going to take action and find a community, find support, find a hub, find a mentor so that you are taking a hint from this incredible city that you’re not meant to do this alone, but you definitely can do it if you have the help in place? Whatever it ends up meaning for you, let me know and I hope that you guys have a wonderful week with this inspiration, with this knowledge, knowing that you do have the tools at your fingertips. Just take them and start working with them. All right. Visionaries, this is definitely to your biggest vision, and I hope that you guys enjoy this. I’ll talk to you very soon and thank you for tuning in.

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