Ep #60 | Best Friends & Business Owners

ImagineMore_August_HeadshotsTemplate copy.png

After a year of research and planning, Jeanne developed the concept of The Groomsman Suit. Day to day, she leads product design and development for TGS. Her focus on high-quality fabrics, construction and components, and meticulous attention to detail are evident in every TGS suit. Jeanne continuously advances the TGS product by leveraging her great relationships with key industry partners that she has cultivated throughout her career.

Being a passionate advocate for the TGS brand, Diana oversees marketing and branding efforts to bring maximum visibility and growth. She enjoys building relationships with engaged couples and industry partners and is committed to creating a fun, easy and thrilling purchasing experience for all TGS customers.



Shantel: Hi ladies. Welcome to the Imagine More podcast. 

Jeanne: Hi, Shantel.

Diana: Hi, Shantel.

Shantel: Hey! We are so, so excited to have you and I am certainly missing Chicago right now in the summer. I know you guys are there. We can't wait to hear more about that and your company. Is it just amazing weather right now there? 

Diana: Yeah! It's the best.

Jeanne: This is when the city comes alive. Three months of just gorgeousness and then ...

Diana: Yeah, I mean, it is hot today. It's a little sweltering, but we'll take it.

Jeanne: After you experience a Chicago winter, you take whatever.

Shantel: Absolutely. Well, let's kick things off by telling the listeners a little bit more about how you guys met and then how the concept of The Groomsman Suit evolved.


Jeanne: Yeah, well Diana and I met in the third grade.

Diana: Yep. At Saint Monica's.

Jeanne: Saint Monica's. I transferred from Saint A's and went to Saint Monica's, and we just-

Diana: Hit it off.

Jeanne: I don't remember the actual meeting, but ...

Diana: Jeanne was one of my only friends in elementary school. I was the chubby kid.

Jeanne: Oh my gosh.

Diana: She was the one that was my friend before I blossomed into the butterfly I like to think of myself as. 

Jeanne: She was always a butterfly. Not lying.

Diana: Not really. A heavy one. Very heavy one. Anyway, so we've been best friends since third grade, and we live a mile away. Our homes are a mile away from each other in Kalamazoo, Michigan where we grew up.

Jeanne: Summers, we would just ride bikes with each other and go to the little beach.

Diana: Yes, our families are friends. Our parents are friends. So we've had a good history, which has really proven incredibly valuable in starting this business together to have sort of that lifetime longevity of a relationship with somebody.

Jeanne: Yeah, it's basically like a family member at this point.

Diana: But one you choose. 

Jeanne: Yeah. 

Shantel: I imagine just that immediate trust. Because you guys have grown up together has helped you guys grow and scale the business, because there's not this figuring out period of what are my strengths, what are your strengths. I bet that's been really helpful.

Diana: For sure.

Jeanne: Definitely.

Diana: For sure. It just so happens too that what I like to do, Jeanne isn't particular fond of, and what totally bottlenecks me and I hate, Jeanne really excels at. So we balance each other out really well.

Shantel: That's amazing. So were you guys always starting companies when you were younger and the lemonade stands growing up, or did this partnership and the evolution of the friendship happen later on in life?

Diana: Jeanne was always designing clothes when we were growing up.

Jeanne: I was always tinkering on things, but, y'know-

Diana: She'd make your prom dress.

Jeanne: And I'd be like, can I make you a dress for prom, do you trust me enough?

Diana: I was like, there's not enough fabric-

Jeanne: No. No, I was constantly conning people into letting me make stuff for them, but-

Diana: You're very.

Jeanne: No, I loved doing that stuff but no, I don't think ... Truly, we never talked about starting a business together and Diana was going into pre-med for college and I was going to design school, so-

Diana: Could not have been further-

Jeanne: To even think of what that would turn into now is-

Diana: How our paths would coincide is like ...

Jeanne: Yeah. So we definitely took totally different paths in what we wanted to do career-wise but we always stayed in touch and we always sort of reconnected at different stages. So I was starting my career in technical design and had the opportunity to move to Boston just a little after graduating college, and started working for Talbots. And I called up Diana and said, you gotta come out here, you gotta come for a long weekend, see my new place, we'll live up, we're downtown Boston-

Diana: We're in our early 20s-

Jeanne: Yeah. So she came out to visit and-

Diana: The rest is history. I ended up getting a job that weekend while I was out in Boston- 

Jeanne: Of course.

Diana: Working for a non-profit. I just, when I put my mind to something, I do it. And then Jeanne and I were roommates for a few years in Boston. I kind of joke because Jeanne convinced me to move to Boston and then Jeanne convinced me to move to New York when we wanted to start The Groomsman Suit.

Jeanne: I start soft with like, would you like to come out for a visit?

Diana: Come out for a visit, and by the way, work on this company with me.

Jeanne: I have some apartments for you to look at.

Shantel: Hard sell.

Diana: And then collectively, I would like to think that we made the choice to move to Chicago together.

Jeanne: Yes we did.

Diana: And then we were kind of just dragging our hubbies along, which they've been really  good about. But it's been a fun journey for sure, as friends and then now as business partners.


Jeanne: Yeah, I think the stars really aligned with, as it relates to TGS, starting the business, Kevin, my husband and I, were living in Columbus, Ohio, just after ... Well, we met there and I was working there and just after we got married, he received a promotion with the company he was working for that relocated us to New York. So I was really excited about that. Knowing Diana was in Boston, it was much easier ... we hadn't really seen each other a whole lot over the timeframe that I lived in Ohio. So we reconnected when Kevin and I moved to New York and being in New York, the resources in New York are just ... People always tell you that, growing up, especially in the fashion industry, New York, New York, New York. And it always appealed to me to live there. I think it was more appealing in my 20s than moving there in your 30s. But we made the jump and having just gotten married, we went through the whole wedding planning experience and had to get our groomsmen suited up. And that was sort of the one task that Kevin was responsible for. I have two brothers, he has two brothers, and then he had tons of close friends. So we had a huge wedding party of nine people. Nine guys to get suited up, and it was on New Year's Eve. So naturally I said, “We're gonna do black tie. We're gonna get them all in tuxedos, make it super easy. Done and done, like check that off your list.” So he went the easy route, went to a big box rental store and picked out the tuxedos and then just told all his guys to order. So for me it was very hands-off, but I realized after the wedding and during the wedding, I saw all the guys suited up and sort of fiddling with their tuxes here and there and they really-

Diana: Switching jackets randomly-

Jeanne: Yeah! They were trading jackets with each other because one fit the other better. And I realized how poorly they fit, really. And that the guys were sort of struggling with them. But I let it go, it was such a fun day, it was not something to focus on. I then the next day had to return a couple of the tuxes for my brothers because they were flying out. And that's when I saw the price tag and the statement was on my mom's credit card because my brothers were younger. They didn't have a whole lot of money to spend on renting a tuxedo and I realized they were just a little over $500 to rent two tuxedos. And that to me just blew my mind. So $250, a little over $250 they spent for the tuxedo rental. And to wear it for one day. So that's when I think the impact of, Wow, this market is crazy, they're an absolute fortune off of something that doesn't really fit or look well but is kind of the only option guys have. So anyway, that's where sort of the bug was planted, like that ... there seems to be a hole in the market here. Then moving to New York, the opportunities opened up for me to look into maybe manufacturing options, wholesalers, something small to dabble in like, y'know, whatever. So it sort of was in the back of my mind. I did end up finding a really awesome supplier, suit supplier with years of experience in fit and had great manufacturers and had their own line of suiting and working with them we were able to develop the suits that we carry now. And Kevin and I decided we didn't wanna invest a ton of money in this and just, what's a way we can prove the concept before going all in? So we started talking about a Kickstarter, met a really amazing photographer, videographer, JJ Ignotz who's still our photographer today, we'd fly her into Chicago a lot, developed the Kickstarter for us, and that's when we had the luck of Diana coming to visit and taking a look at it for us.

Shantel: That's amazing. And so from there I imagine the Kickstarter was successful, and then you guys went, “Okay. We actually are going to launch this,” or was there still some, “Is this a good idea?” Like was there any questioning after the Kickstarter?

Diana: I don't think there was any question, like once we launched The Groomsman Suit, it really just took on a life of its own. We sold about a hundred suits and tuxedos in 30 days and we were like, “Oh! We've really gotta launch our website.” There was already sort of a preliminary website started and so we worked quickly to kind of revamp it and launch it officially and then it was really just off to the races. I mean, it became very quickly our full-time jobs. 

Jeanne: Diana was actually the first full-timer out of the two of us. I was actually on maternity leave as we were launching the Kickstarter, which was sort of the plan as it was just to have the time off to do it. But I was definitely in over my head. And I think Diana, when Diana came and took a look at it ... I've always turned to Diana for advice on anything I'm doing. Starting a new job, dating someone new. And so it was very natural for me to say, hey. I've got this crazy idea. It may be the stupidest thing I've ever done but I have these suits I wanna sell and I think we could do, y'know, maybe like 10 a day eventually. Eventually we could sell 10 a day. And that would be X amount of dollars and that's big-time.

Diana: And we could live on that forever.

Jeanne: That's big-time! But Diana having just finished business school and really was very high-level at several other companies, prior to coming to TGS. She had a way of looking at the business plan really just showing us what it could be. And I think having her talk to me about just the actual scale we could take this really got me excited and half the time I was like, “Are you sure Diana? Is this real?”

Diana: Yeah. It's the best! Working with Jeanne is the best. Because she really trusts me with what I think might be our potential, and it's so fun because she's always so excited about it.

Jeanne: Well yeah. I mean, the numbers she writes down of projections, I'm like, “You really have to reel it in, Diana.” 

Diana: This is not realistic.

Jeanne: This is impossible! And then when we exceed those numbers, I always look at her and laugh and I'm like, "Jesus. You are just like a little wizard." I didn't know that could even happen. So I think that gave me the confidence to sort of calm the nerves of launching the Kickstarter. I think it is scary any time you put a business out to everyone. You worry that you're not gonna hit that target, and then you have to tell all your friends and family that, "Ooh, well, that failed. That business failed." And no one wants to do that. So Diana was that extra needed boost of confidence. But not only that, I think her networking and just social ability in general to share concepts with people and get them on board and excited about it really made all the difference in the Kickstarter and hitting that target. So for me it was that moment of hitting that target and having Diana as that immediate sounding board for everything that I think we both realized we had something really special.

Diana: Yeah. I mean I think, and we're not really answering a specific question, sorry Shantel-

Shantel: It's okay!


Diana: I'd say that like, I think my strength is execution and sort of seeing longterm vision, but Jeanne really is like the innovator. And so never in my wildest dreams, like I'm not somebody that has necessarily ideas, brilliant ideas, I happen to be really lucky that my best friend does and then I can help take them to life-

Jeanne: You're being humble.

Diana: No it's true, like that's I think why we have such a great relationship.

Jeanne: We are very well-suited for each other. Yeah, and projections, I, that doesn't ...

Diana: It's fun.

Shantel: I love how it's ... I mean seemingly, it's pretty neat when I'm chatting with entrepreneurs on this show. There's so many people that it's just an organic kind of development. I mean they saw an idea, they saw an opportunity or a niche, and it's never super calculated or, it's not like they write a 10-page business plan before. They pop out an idea, they execute it, they try, they test, and then they continue to innovate and tweak the process and everything and it sounds like that's what it's been like for you guys which I think is really fascinating.

Diana: Yeah, we've been really fortunate to have immediate proof of concept from the launch of The Groomsman Suit. I mean, a lot of times it's not this easy with companies. They have to pivot, they have to tweak their go-to market strategy. I mean, truly from the moment we put this out it's really taken off. And that is the sign of a great business idea, right? Like if you really have to force something into the universe and it's fighting back at you, you really have to re-strategize and that's when a lot of startups have to pivot or maybe not even make it. But for us, it has just pulled us. Like, the need and the demand for affordable men's wedding wear in a reliable and convenient way has just pulled The Groomsman Suit to life. And so now Jeanne and I actually are just holding on for dear life.

Jeanne: Yeah! How do we keep supply-and-demand is really the biggest problem.

Diana: This monster!

Jeanne: It is absolutely ... It was not a forced business. It was a very slow built concept on a very simple idea. Y'know, five basic suits, that's all it is really. And exceptional customer service. As soon as we started getting feedback from customers very early on like, “Wow, you guys are amazing, this is the best service. Thank you for being so responsive.” We looked at each other like, wow, these guys really don't have-

Diana: Have not been treated well.

Jeanne: Have not been treated well! Because we're talking about, I mean, it was just the two of us answering emails and filling orders-

Diana: Yeah. And we're just being normal.

Jeanne: We thought it was normal, yeah.

Diana: I mean, this is it. This is all it is. It's a great product, and it's a great service.

Jeanne: That's it!

Diana: It's not rocket science, but it has really changed things.

Jeanne: Yeah. It's become more sophisticated since, but ultimately that's really the key.

Shantel: And I think that that, I imagine, is core for any successful company is staying true to that, one, customer service component, but also the products and the delivery, which I think Y=you guys have nailed which is awesome. And I loved how you called the company “The Monster.” Like it happened so fast and we're certainly going through, at least I can relate in the sense that sometimes it just feels, and I say “Train.” Like the front of a train and just like, holy cow, what are we doing? And trying to keep up and make sure we're being the best leaders that we can. But it is a wild ride for sure. I would love to kind of dive into day-to-day. So you guys touched on execution and longterm planning versus the innovator. How do you guys break that down into day-to-day responsibilities and the roles?

Diana: Well, I mean, it's pretty clear-cut. Jeanne really moves our product forward on a day-to-day basis. Working with our manufacturers, perfecting our design ... She's really amazing with the internal logistics to the company as far as like, our fulfillment center and ensuring that our orders are packaged and processed in the right way.

Jeanne: Yeah, we sort of just, it's a natural separation and there's very few times that things overlap that we both are like, “Should I get on this? Or should you get on this?” But Diana is definitely the planner, forecasting where we spend our dollars. She also does a lot of the order prediction so how ... So really the hardest part for us is to predict the size of the orders that we need for six months from now because when we're placing orders today we're not actually going to have them on hand in six months. So Diana does a lot of prediction and formulas to kind of forecast that which is really, really the backbone of everything because having inventory is the only way we can supply the customers. But as far as day-to-day goes, we both were so heavily involved in the customer service side for so long that I would say day-to-day that was our primary goal is just fulfilling orders and giving customers what they need. Now that we have employees and can delegate off a lot of that customer service volume to them as we grow especially, we definitely have separate roles where I am much more product-involved. But we heavily defer to each other. So if there is ... Ultimately at the end of the day, it's the decision we both make on everything so we're both 100% accountable for what is actually put out there and how things are executing in general.

Shantel: Is there anything that's still on both of your plates that you cannot wait to take off or delegate or that just kind of drains you as a business owner?

Diana: I mean, Jeanne just got done saying how fabulous I am at inventory management, but man, not really. I would hand that right off to an expert! Let me just tell you. It is something that keeps me up at night. But I mean, we are both probably doing more customer service than we should be. It's hard though because we both love that. I just, I love talking to customers. If I could I'd answer the phone all day long but I can't anymore, so-

Jeanne: Well, you know what, it's also the number one way we figure out how to improve processes, is feedback from customers. So if we ... It is a little scary to completely step out of it because then you lose a little bit of that personal interaction with people that we are needing to-

Diana: Serve.

Jeanne: Serve very well. So that's hard. But yeah, I don't know.

Diana: Some fulfillment stuff I think would be nice if we had like a fulfillment-

Jeanne: The nitty-gritty stuff. We have returns and exchanges constantly being processed and monitoring the inbound versus outbound. All these little technical things would be nice to hand off.

Diana: Some IT stuff too. But, I mean, we're getting there.

Jeanne: We both enjoy everything we get to do here, honestly, so.

Shantel: Well yeah. It's nice to hear some of those real answers of, there are gonna always be things but the bigger picture is very fulfilling and this is just part of starting a company.

Jeanne: Yeah!

Shantel: As best friends and business owners, how do you guys unplug, or is it kind of all hands-on-deck right now, all hours of the day, or have you guys been pretty intentional about trying to unplug from the business and just be friends?

Diana: I mean, I think that's kind of one of the best things that, are one of the things I think I'm the most proud of with doing this company is that Jeanne and I still hang out.

Jeanne: We unplug very easily with each other and shut off the work head.

Diana: Yeah, I mean it's fun. I mean, we see each other all day long and then on the weekends I'm like, “So, what are you doing? You wanna go shopping?”

Shantel: That's nice! You would think you'd get maxed out of the person.

Diana: Yeah. I'm like, “So, what about Thursday night? Do you wanna go out?” So I mean, I haven't always had that type of workplace environment where I wanna hang out. And it goes with, actually, the rest of our team too. Like I love our other teammates. I would hang out with them, but especially with Jeanne, I think it's just natural. I mean, she's like a family member so it would be weird if I only worked with her and then didn't see her on weekends occasionally or whatnot.

Jeanne: Yeah. And Diana and I are 100% TGS kind of all the time in our minds just because it's just what we think about a lot. But I do think having a partner is so amazing because she can go on vacation and I can make do while she's gone. Y'know, for the most part-

Diana: And be happy about it, and be happy that she's getting out, you're getting a break, and like-

Jeanne: Yes, and then vice versa where if you don't necessarily have that business partner to rely on when you leave and you stress when you try to-

Diana: For sure.

Jeanne: When you try to detach you get too stressed out and then it doesn't end up feeling like you detached at all.

Diana: I mean, I think we're still trying to find our work life ... It's not balanced anymore. It's not even like, maybe it's harmony. I mean the thing is that we love our jobs so much. We love what we do. It's also sort of our hobby. And then because we hang out all the time together-

Jeanne: We talk about our hobby.

Diana: But we do need other hobbies, which sometimes we go shopping. But we, I mean it's certainly like, I think for us now that we're able to bring people on and expand our team, we're exploring “What is our good routine, our day-to-day routine? How do we work best? How do we get into zones of productivity?” I know I'm really personally trying to figure that out. When do I work out during the day? So that we can be the most effective and still really enjoy our job. And even get to dabble in some parts of day-to-day customer service stuff that we don't always have time for but if we're really productive and efficient then we can, and it kind of keeps us rooted to the core of our business. 

Shantel: I love how you called it "harmony." I think that's such a great word. Balance, it's hard. And I don't know if it even exists. I think there's different phases in everyone's lives, but I liked the harmony piece, and even thinking through when do you work out? Like I recently realized the middle of the day, closer to kind of this two or three o'clock hour, is when I actually kind of hit the slump, and I need to refresh with something. And then it's just being diligent and putting it in the calendar so nothing else gets in its spot.

Diana: Yeah, I know. Absolutely. I mean we're always trying to figure that out. I think for us it's just having I think coverage too for customer service plays a huge rule and our flexibility and our routines, but-

Jeanne: And as we grow, it does become harder actually to figure out schedules because everything shifts a little bit. Whereas now Mondays are like the crazy day for us.

Diana: Insanity.

Jeanne: It's all hands on deck, but then as the week goes on, it gets a little easier. But yeah. We've, I mean I sort of have a ... I don't get to the gym hardly ever. But my schedule sort of focuses around the drop-off and pickup of daycare. And as long as I do those two things every day and come into work, I'm good!

Diana: You're not being put in jail!

Jeanne: I have, exactly. I have a routine and then I like to work a little bit at night. I'm more of a night owl. Diana's definitely an early bird. So, just sort of ...

Shantel: Well yeah. I love that, thanks for sharing kind of how you guys break that down. I just have a few more quick questions for you guys to wrap things up. And the first is, is there anything exciting on the horizon, some new developments in the company that you guys can't wait to launch or start talking about?

Diana: Oh my god, there's so much.

Jeanne: So much. Probably too much.

Diana: I always think like, what is there really gonna be this time next year, and we're gonna be saying the same thing. Like, last year there was so much going on. This year we have our showroom and new headquarters opening here in Chicago in a couple of weeks.

Jeanne: We just finished a photo shoot a couple weeks ago for new suit color development-

Diana: A used suiting line-

Jeanne: A kid's line ... The kids line is probably one of our favorite upcoming things because we get so many requests for kids' suits and we really do feel like ... That's like another moment we had in the business of realizing, oh, there's another hole in the market where youth suiting matching the adult suits for weddings, specifically for weddings. So that's something we're really excited about and should do really well with next year. And then we have been dabbling in women's development. Just creating a really beautiful fit for our women's line. Keeping in mind not all women wanna wear bridesmaids dresses, and sometimes your best guy friend is getting married and it would be nice to stand up on his side and maybe wear a suit and what he picks for his groomsmen. But we just wanna give more options for women in general for suiting. Whether it be wedding specific or just like they need a great suit fit for their body type. So we're working on that, and hopefully ... We have so much in development that we're at the point now where we're just trying to be really selective about what we launch and when we launch it, because our core collection that we offer right now is number one priority to keep supplying the demand.

Shantel: Well I can't wait to see all the fun pictures that came out of that shoot, and the kids especially. I'm sure it's adorable. Second question, for anyone who is exploring starting a partnership and picking that perfect partner to kind of go through life and that business with, do you guys have any advice on who to look for, qualities, anyone that wasn't best friends with that person already? Can I have some takeaways there?

Diana: I mean, finding a good partner I think is paramount to having a successful company. Complementary skills is really important. It will keep you from sort of stepping on each other's toes and give you each a focus to move the business forward. I mean, it's just so hard to say. Like-

Jeanne: It's hard to say because we know what we have is so-

Diana: Rare.

Jeanne: Unique. Yes, and so to think about finding someone who you don't have this close relationship with to start a business is sort of very foreign concept for us. I would think that that's like the number one hardest thing to do when starting a business, is to decide on ... either find a business partner, either you have the concept and you need help with separate skillset that you don't have, that sort of opens up the doors to, okay, seek out leaders in those fields of expertise, and or partner with a few people. I actually think that there's a trend now for businesses with multiple co-founders, three, four, five, which I think is really-

Diana: Smart.

Jeanne: Very smart. Because you can get people with very specific skillsets, all equal and important.

Diana: Provides more balance too, because I think when you have two people it could be a harder dynamic to strike a balance. But the more people you have-

Jeanne: Yeah! Exactly, you've reduced that power struggle.

Diana: It's deferred. The power struggle is certainly deferred.

Jeanne: And like, who's doing more than the other person ... If you don't have that deep, deep relationship with the person, I would think it would be very hard. You would have a lot more power struggle moments. You'd have your business that you're trying to nurture, and your relationship that you're trying to nurture which really does start to take away from the business if you let the business relationship and who's doing what sort of take over that dynamic. I would think that that would be very hard.

Diana: I mean, the thing is, so I think that's brilliant. Like, having multiple co-founders. I think too, you've gotta come up with a way of understanding conflict resolution or how do you communicate. Because there are some challenging moments, especially in the beginning as you're talking about the setup of the company and everything like that, and it can make for some awkward conversation. And if you don't have good communication, like collaborative communication styles, then that can be tricky. So I think figuring out right away how you communicate with people is gonna be really important.

Shantel: I think those are definitely great tips, so thanks so much for sharing. And last but not least, how can people get in touch with you and learn more about The Groomsman Suit?

Diana: You can chat with us-

Jeanne: Anywhere on our website that says Contact Us can eventually make its way to me or Diana.

Diana: Yeah. So thegroomsmansuit.com is our website. And like Jeanne said, we have different ways of-

Jeanne: Channeling those-

Diana: Yeah. And we're pretty close to the customer service so we're like one service agent away. So if anything comes through and says, "I wanna talk to Jeanne or Diana!"

Jeanne: We're right there!

Diana: We've got it.

Jeanne: Sometimes we even answer the phone you call, so-

Diana: And you might, you might find us on the other line. But yeah, we love to hear from people. It's been so fun to get support from other entrepreneurs, women in business-

Jeanne: Yeah! Diana actually set up this really fun social media page for us to share the startup story and journey from a more personal side. It's found.her is our Instagram handle and we post pictures of, like, our space being renovated and then new team members joining the team and-

Diana: Funny messages that customers write-

Jeanne: Funny messages, yeah-

Diana: In their order! I mean, it's really random.

Jeanne: Random, but really fun page I think for friends and family to follow, and then a lot of startup space people follow us and we follow back a lot of startup things. So it's very startup-y. And it's very much, it's a lot more personal. Like of pictures and things of myself and Diana and our families every so often. So if you wanna see the behind-the-scenes, that's really where to go, is follow us on found.her and then we have regular social media for The Groomsman Suit on Facebook and Instagram and can all be reached through there too.

Shantel: Great. Well I just followed found.her so thanks for that. And we can't wait to see as the launch of the new lines come out, and we'll certainly be sure to hyperlink in the notes below. But thank you so much for being on the show and carving out the time.

Diana: Thank you much Shantel!

Jeanne: Thank you! It was so fun!

Diana: It was so fun, yeah!