The Flyover Series is a collection of interviews with founders and key contributors of Chicago-based tech companies. Our goal is to help illuminate some of the terrific people and work in the Chicago technology scene.

This interview is with Jill Salzman, founder of The Founding Moms. 

So, to start, who are you?

Jill: Who am I? So many jokes, so little time! I’m Jill Salzman of The Founding Moms and a musician on the side.

Can you tell us a little bit about Founding Moms?

Jill: We are a collective of offline meetups and online resources for mom entrepreneurs. We are currently in 45 cities, 9 countries, with 8,000 members. And, I’m in the middle of a busy season of launching a couple new cities, so hopefully we reach 50 soon. We are launching an online portal in January to help all our members connect. It’s a very exciting and crazy time right now.

What is the genesis of The Founding Moms? What made you want to start this kind of community?

Jill: I didn’t want to start it. I didn’t intent to build anything like this. I was running a music management company and a baby jewelry company at the same time, and I was pregnant with baby number two, and wondering how the heck I’m going to run these two businesses with two babies in a home office. So I started a meetup for selfish reasons - “Hey, you have a baby and a business, come talk to me.” And about six months into that very low key monthly meetup, I discovered that we had 200 members in Oak Park online, and some woman asked if we could open up a chapter in Chicago, so I did. I realized I could open up anywhere and I’ve been doing that ever since. That was late 2009 and I was panicked about two babies and two businesses and then in early March of 2010, I opened up New York. At that point I thought, ok here we go let me formalize this into a business, and here I am four years later.

Why did you focus on The Founding Moms over your other two businesses, music and baby jewelry?

Jill: It kind of goes in order. I started the baby jewelry business because my music management business would go through the big roller coaster ride of, if they’re on tour you make money, if they’re in the studio, you don’t make money. So I thought, let me start a second company. I just thought I’d throw up a website and sell some baby jewelry just to make money, to fill it in. And then, I realized there were so many members to this meetup in such a short amount of time, it felt like a street team situation to me. And I was very familiar with street teams from the music business, and I thought I could create street teams for all of these mom entrepreneurs. And it feels bigger than anything I’ve ever done before, and it’s a market where members have income, unlike musicians, so I knew eventually I could build a product they would pay for. Honestly, I could over-analyze it, but it was a gut feeling that it was something bigger than anything I had done previously. And it turns out I was right.

How many years ago did you start your first meetup?

Jill: It was four years ago that I founded the first meetup that became a Founding Moms exchange. That first meetup had 200 members and then I just kept opening and opening more meeetups. People kept telling me to stop, to figure out my business model, but I kept going.

Is it safe to say it’s all worked out?

Jill: There could be more income coming in, but we have so many things in the works right now that it’s awesome. I love it all. I love it all.

How did you get started with the first meetup? What were some of the things that you did?

Jill: The very first meetup I remember showing up, hoping that five women would join me, with literally nothing, and I’m going to say literally again, literally nothing but a baby strapped to my waist. I was so desperate, I had no plans, I thought it was going to be coffee. After maybe three or four meetings I noticed that everybody was wandering, a bit aimless, some were bored, some wondering what they were doing here, and I realized why don’t I just write down an agenda, try and look organized, and pretend that I know what’s going on. So I showed up with an agenda one day and it changed the whole game. People thought I knew what I was doing, that there was direction, and since introducing that agenda it’s been fantastic and there’s been a lot of order. At every meetup I learn something and I change it up a little.

So the first meeting was more of a “Hey we all have something in common? “

Jill: It was just a hangout. It was “Oh you have a business and a baby, cool.” There was a lot of “what do you do?” I wish I had filmed those first several meetups, relative to what happens now where it’s wildly organized. People come, they know what to expect, they don’t have to introduce themselves, and they know what the whole thing is about. We didn’t have speakers for a number of months, now we have speakers at every meeting. There’s a whole entire hosting system that is systematized for all of the hosts around the world. It’s different, it’s morphed a lot.

What has been your process of building up the meetings through the years? Have you preempted the demand or has the demand preempted you?

Jill: At the beginning, I was preempting because I wanted to open everywhere. I would call New York; I would call friends in LA. I could go back and look but I want to say I reached out to the first eight to ten cities. And then it felt like it was becoming too much for me, so I threw a form up on the website and said “if you want to do this in your city, contact me.” So to this day, I no longer seek out. If you want to host in your city, you contact me, there is a form on the website, there’s a whole on-boarding process now. I stopped seeking out a long time ago. The only times I will seek out now is, for example, we recently had a host who had to leave because of a family emergency, she can’t host anymore, so I will reach out to the city and say “Is there anybody who wants to come step up?”

So each city has a host? Their own Jill Salzman?

Jill: Yes, the host runs the city meetups, to be me in her city, basically. She has to come on and figure out the local culture, and it’s kind of a very open source organization, so I give her a couple of tools, and she runs with it.

Is each meetup the same as Chicago? Do you talk about similar things?

Jill: No, I really hope not. In fact, in some cities I don’t know what they’re talking about. There’s an outline for each step of the way and everything that we do. Some take it very much to heart and do exactly what we’re doing, some don’t. But nobody could be doing the same thing everywhere because if I have a speaker who cancels last minute and I replace the speaker, then the topics change. 2015 will be the first time we all have a host call together. That’s going to be a first.

What else has changed about the meetups over the last four years?

Jill: So much has changed, it’s a big question. Let’s start with monetization. For the first three years there was no monetization. I offered everything for free, all meetings were free, and there was no online portal. As of January, 2014 we flipped the switch, so that’s a big change because there’s money coming in. About two years in I started taking on sponsorships, which is what carried us for awhile. It still carries us to some degree. That has always morphed and always changed in terms of how much money we ask for and what we can do. Obviously, the more cities we have going on, the more we can do. Membership itself has changed quite a bit too. On average we’ve gone from woman desperately crying “how am I going to do this?”  or “I kinda want to launch something” to a large majority of the members, maybe 90% of the members I see, who are already in business. Our meetups are kid-friendly, though most don’t bring their kids. They have that worked out already; they know how daycare and school works. We meet in the middle of the day. They are at the beginning of their business, but not business idiots.

Is this becoming more of a networking opportunity?

Jill: I hate that word, but it’s ok because I basically run a networking organization. I wanted it to become an educational forum really, where you come, and while we’re called The Founding Moms, we’re not talking about our children. You come and hear us, hear our speakers, and then you leave the meeting and think “Man, I’m gonna go try that and apply it to my business today, and hopefully, it’ll make me more money.” I look at it as a place to come and learn, where at the end of the meeting it turns into a networking feast. People have bartered services and bought each others services, and it’s been awesome.

Have there been any useful resources, in terms of technology and networking, which you’ve used over the past four years?

Jill: So many. Obviously, the whole entire business is built on Meetup.com so I’ve tapped into their technology for years. We’re still using Meetup.com but I can’t wait to get off their technology and build our own. But I don’t know anything about development, and I haven’t gone out yet and figured out how to do that. Part of it though, and I can’t gauge this yet, is paying Meetup what we’re paying to use their system. I could take those fees and use them for marketing. We use Meetup because their marketing is so powerful. Every time we launch in a new city, every single person who has the same interests that we list are notified within a 100 mile radius of where we launch. It’s a massive awesome promo. But, it’s also the only thing we’ve ever done, so is it really awesome? I don’t know we haven’t tested out an alternative. In terms of other technologies I’ve liked Evernote and we’ve used it a lot, and I’m obsessed with Mad Mimi, my newsletter provider. Their customer service is awesome that I feel like I know and love them personally. The newsletter that we send out has been so helpful to growing our company, and has gotten us so much money and so many things, that I cradle it in my arms every day.

Where are most people finding out about The Founding Moms?   

Jill: We’ve been asking that a lot. In fact, we’re just about to bring on a data person who might be able to answer that for us. I think it’s Meetup. I think people just troll Meetup and think “Let me look for a group” and then they join us.

What about here in Chicago?

Jill: There’s a lot of press that I do, so people hear about us that way too. A lot of it is word of mouth, which is fantastic and horrible because it’s the king of marketing and you can’t pay for it. Fortunately, our members talk a lot about “oh I’m going to the next exchange, you should come with me.” But, it doesn’t happen nearly enough. I know the ways that I do outreach but I don’t know what’s winning. But, about a month ago we revamped our blog, there’s a new person writing, it’s fantastic. For the first time in four years we’re getting comments on our blog. But I don’t know if that is bringing new members.

What’s the most difficult lesson that you’ve learned over the past couple of years with The Founding Moms?

Jill: I have learned that I for sure don’t know what I don’t know. I have learned that no matter how good I get at marketing and PR, and no matter how much I have conquered that area, there is so much more I could be doing, because it my view, that helps tremendously to get the word out, especially if you’re an international organization. There’s a lot in there that I’d love to do now that I know about what I could do. That’s a great catch 22. I keep getting savvier in the department, for someone who knows nothing, I know a lot more than I once did. But there is so much more that I wish I knew. I have a four year old and I put her down in front of code.org or Hopscotch because I desperately want my children to be able to code their own shit one day.

Where are you going next with The Founding Moms?

Jill: We’re going a lot of places. It sounds really crazy but I’m just going to say it. I’d love, in the next year, to open fifty more cities. That would make us 100 cities strong, which is just crazy. I would love to have myself on some national talk show, a lot more people will know we exist. Every time I hit something local, a lot of people will say “I’ve never heard of you in Chicago” and I wonder how they haven’t heard of us, because we’re pretty big in Chicago now. But the power of the press is good, and I‘d love to do a talk show, or meet Stephen Colbert. And, I would love for the online portal to sort of blow up. But it’s a forum plus web courses and that takes time since it’s hidden. I think that will take a couple of years.

Do you have another conference planned?

Jill: Yes, if we get the sponsorship money we will be having one in 2015. 2014 was an awesome success but quite stressful, only in the “do we have enough money to do this” department.

Was the first conference in October? How many participants?

Jill: Yes, the first conference was October, 2014 and we had a lot of cities show up, but about 120 people in the room. We had incredible speakers. It was a really great fun community building day. It was fantastic; everybody just walked away and said “Man, that was life changing.” So it was great and I want to keep it small again, but we need big money to keep it small and good, rather than big, and not so great, and expensive.

Are there any resources in Chicago that you have found particularly helpful for The Founding Moms?

Jill: I heart 1871 very much because I hear of a lot of Chicago resources through it. I also like General Assembly a lot and Entrepreneurs Unplugged. I know they just put on, or are putting on very soon, a conference called Elevate. I haven’t been, but they’re a great resource for entrepreneurs. I’m very face to face so the things I like are local meetups or events. I actually don’t know how many of the resources that I’ve used are from Chicago. We’ve used Basecamp in the past and they are from Chicago.  But this is the first time I’ve thought about it in that way, locally.

Do you think that a space like 1871 is a catalyst for speaking engagements?

Jill: Totally. There’s a Chicago resource called Ms. Tech for women in tech in Chicago, and they used to have a lunch that I would show up to. It’s really nice to be in a space where once you’ve done one speaking gig to a group of people, part of that group might be sitting in 1871 the next day. It’s really good PR all the way around.

Why are you based in Chicago?

Jill: I love living here. I do love the people and I love working with people here. It’s been an awesome experience.

You're from New York?

Jill: Yeah, it’s too expensive and people are crazy, and I love crazy people. I think I’m crazy but you know, Chicago is just a great place to build a company. I’ve also lived in LA and I would never want to go back to either city and build there.

What’s your number one takeaway for yourself that you think other people should pay attention to or focus on?

Jill: The best and worst advice is to listen to everyone and to no one. I say that because I do all of my market research by asking a lot of people, usually sitting around me in the day, what they think about a new marketing plan, or a website design, or this new graphic, and I love getting all the input, but then you can’t always listen to a lot of the input. And I say that because I see a lot of small business folks who hear a lot of input and get really confused and don’t do anything, or take it all to heart and get hurt. You have to take it all with a grain of salt, but ask people questions because they will throw a lot of great ideas at you that you will never have thought of yourself.