The Startup Ladies with Kristen Cooper

startup ladies.png
What we’re trying to do is raise awareness about the obstacle, identify people who have the capacity to write checks, educate them about startup investing, and connecting those funders to our founders.
— Kristen Cooper

In this episode, I talk with Kristen Cooper, founder and CEO of StartUp Ladies, a for-profit membership organization whose purpose is to increase the number of women who are starting up and scaling businesses. They do that by providing educational programs and creating a community for the next wave of startup investors: teaching them how to invest and connecting them to women and minority-owned businesses

Kristen shares the founding story of how she created a community of like-minded women who wanted to learn from each other. She made a list of the topics she wanted to learn more about and a list of people within that community that could teach on that topic. She shares the process of entrepreneurs and future investors use the online platform to ensure the funders are taking the necessary learning sessions in order to be prepared for conversations with investors.

Topics In This Episode:

  • How to create community in your space

  • Growing that community into a for-profit organization

  • The need for structure, consistency, and accountability

  • Importance of mental wellness for entrepreneurs

  • How to expand a physical community to other physical spaces

  • The kind of people you should have on your team in order to grow and expand

  • Missed opportunities for StartUp Ladies

Contact Info:

Visit the website: thestartupladies.org
Send me an email: kristen@thestartupladies.org


Transcript

Mike Kelly:                         
Welcome to the Startup Competitors Podcast. Today we have Kristen Cooper who's the founder and CEO of Startup Ladies. Welcome.

Kristen Cooper:                
Thanks Mike.

Mike Kelly:                         
All right, why don't we start with a quick overview of Startup Ladies?

Kristen Cooper:                
The Startup Ladies is a for-profit membership organization and our job is to increase the number of women who are starting up and scaling businesses. And we do that by providing educational programs in person and online. We create community and what we're doing is identifying and educating the next wave of startup investors. We're teaching them how to invest and then we're connecting them to women in minority-owned businesses.

Mike Kelly:                         
Maybe let's start with how you got your story. So when did Startup Ladies start and why and I'd love to hear the founding story.

Kristen Cooper:                
I was working for a software development firm out of a coworking space and there were not very many women. And at the time I was wrapping a technology project that I had started and had so much fun with and in fact, had such a good time. The founders of this software development firm invited me to come work with them and they promised they'd really teach me how to build technology and I would help them grow their network and help them with things operationally.

Kristen Cooper:                
So while I was there, I was really interested in finding other women that wanted to build technology and start up scalable businesses. And back in 2014, there were so few women here in Indianapolis that were in the tech space let alone leading tech companies. So I was really just in search of women that had similar passions. So what happened was one day I was negotiating a contract in the ladies' room of a coworking space with someone who I kep bumping into in the ladies' room. And what would happen is we would be washing our hands and just catching up with one another. And one day I had mentioned a project that we were working on and we figured out that we could work on it together.

Kristen Cooper:                
And I said to my friend, "You know, I think we could be a little more civilized and maybe we could start going to lunch." And I said, "I've met a couple of other girls here in the ladies' room." Because what I was doing was the sinks faced the door and since there we so few guys and I wanted to meet other women in this space, when they walked in I would just introduce myself. And so it was friendly and then led to business one day. And so I was like, "I'm going to invite a couple of the girls that I've met in here. We'll just go to lunch and it'll be nice that we-

Mike Kelly:                         
This is the best founding story ever by the way. Like it's fantastic.

Kristen Cooper:                
So we went to lunch and I invited seven people, women, and only three of us showed up but we really had a great time. We had a great conversation and we all agreed it was so much fun we do it again. And I said, "Well, I'm going to invite some of those folks." And I said, "There's some other women I know in the community that I think would just enjoy spending time with us. And if it's just once a month, no big deal."

Kristen Cooper:                
And I kept doing these lunches. And they kept growing because the purpose was to just get together talk about business and I kept asking women when did they want to start a business? Two, did they have any interest in building technology? And what was stopping them? And those three questions caused so many amazing conversations and we just kept bringing more people on. And someone who's been a great mentor to me who was starting up Eleven Fifty at the time that Scott Jones said, "Hey, I see that you're working in tech and I hear you're doing something with women and entrepreneurs, I'm starting up Eleven Fifty Academy and we're hosting different groups over here. Do you want to bring your group over for lunch?" And even that Scott Jones, I mean, he's skilled voicemail, right?

Mike Kelly:                         
Right.

Kristen Cooper:                
An invitation like that from Scott Jones is something that you only say, "Oh my gosh, yes and thank you." And I said, "Can I bring a few extra people?" And he said, "Sure."

Kristen Cooper:                
So we had 70 people at his house for lunch.

Mike Kelly:                         
A few extra.

Kristen Cooper:                
Yeah. So he paid for lunch and then he stayed the whole time and he was answering every question that everyone in the room had. It was just so much fun. But then it was after that people were like, "Hey, we had that you had a big group of people over at Scott's house, what are you going to do next?" And I was like, "Well, I think I'm done." Like that was it. Like we had a big group and that was successful. And [inaudible 00:04:43] said to me, he's like, "I think this is the time where you go do something with this." And I said, "Well, you know, this is fun and I've enjoyed their company but I really don't want to be a lunch and events planner."

Kristen Cooper:                
I said, "What I want," and I just started listing off these things as far as trying to have a better understanding how to build a scalable startup. And I said, "Yeah, I wish there was like a place where I could go and learn from all these people that I've met." And I was like, "I need like a study hall like about startups." And I was like, "I need like a Startup Study Hall." And he said, "Why don't you just go do that?"

Kristen Cooper:                
So because I had been a fundraiser for almost 20 years. I had built up a nice Rolodex and I made a list of all the things I wanted to learn. And I had about 70 different topics then I put a list of all the people I knew that were experts in those areas and I just sent them e-mails and I was like, "Hey, I know a bunch of women that would like to learn about this and we're interested in ... We're just noodling on the idea of building businesses and could you come and just teach us this one thing for like an hour and a half?" And so the first woman I asked, she's on our board now, Julie Warnecke, she owns Found Search Marketing and she works at Google and help develop Google ads.

Kristen Cooper:                
And she taught our first Startup Study Hall in search engine optimization and search engine marketing, which I knew nothing about at the time. And so we enjoyed ourselves and we thought, "Well, this was great. We need to keep learning it." But the thing we knew for sure is that we needed structure, consistency and accountability. The same thing that all these moms were providing their children to become scholars and athletes and musicians and artists but they weren't doing it for themselves. And so we thought, "What if we provided that?"

Kristen Cooper:                
So we spent three years doing these Startup Study Halls the first and third Wednesday of the month. And we had waiting lists and we had so many people come that people were saying, "Hey, we would pay you for this. I can't believe you're doing this for free." So I had put a board together that was purely advisory and they said, "Hey, you can keep doing this and you're going to burn out or you can really commit to it and start solving some of the really big problems that women founders have."

Kristen Cooper:                
So two Mays ago, I left sticks and leaves to do the Startup Ladies full-time. And so now, not only are we providing programming through Startup Study Hall, we've also got a program called Startup Investing 101 and we're working with, it doesn't manner, women, men, transgender, genderfluid people have an interest in investing in startups but don't know how. And so they've got capacity to invest at least $5,000. And one of the biggest obstacles, particularly for women in minority startups is that these folks don't have networks of wealthy people. So while it might be really easy for a lot of guys to go get 50, a couple hundred thousand dollars, like it's tough for women that don't have networks. They don't have family members or close friends that can write for 25 or $50,000 and that's what I want to change.

Kristen Cooper:                
So what we're trying to do is raise awareness about the obstacle, identify people who have the capacity to write checks, educate them about startup investing and then connecting those funders to our founders. And last year, in our first cohort, we had about 20 investors. Not all had made their investments yet but we moved $60,000 from the funders to the founders. And one of my favorite stories of financial success is Christine McDonnell who's the CEO of Codelicious who hopefully you'll interview some time. But she was able to secure $50,000 from two of our women investor members.

Kristen Cooper:                
So now we're tackling the problem of women who typically have some form of college education, they tend to be parents, incredibly busy, came up with an idea because they became an expert in their particular industry. They came up with the solution to solve the problem and they have no idea how to build a business, they have no idea how to build tech so they're looking for a community. They're looking for someone to teach them how to build a business in technology. They're looking for people to just tell them, "What do I do next?" And then they're looking for funding. And so those are the challenges that we're addressing.

Mike Kelly:                         
So the really big problems female founders have community, education, guidance and funding.

Kristen Cooper:                
Yes.

Mike Kelly:                         
Anything else missing from that?

Kristen Cooper:                
Yes.

Mike Kelly:                         
Bring it.

Kristen Cooper:                
I was just writing a grant application and they said, "What's the number one thing that surprised you in the work that you've been doing with entrepreneurs?" So you're a really good conversationalist and you can ask a question and you get someone to open up. Well, in my line of work as a fundraiser, I spent 20 years doing that and so when I would see one of the girls at Startup Study Hall, I ran up to her and I'd be like, "Hey, so and so, how are you? Last time I saw you, you told me you were working on this. Give met update." Something as simple as that would go from update to here's what's really going on to oh my God. And sometimes it would be a very tearful explanation of what they were feeling. And I would say that, "Not only was this happening with happening at Startup Study Hall but throughout my career this was happening with men too.

Kristen Cooper:                
So after this happened so many times I went to my board and my therapist and I said, "I'm making people cry left and right. I need you to help me to figure out what I'm doing 'cause I need to change it." And so they said, "Explain exactly what you're doing." And I said, "I would be in a situation where we're having a good time and I would say something along the lines of, 'How are you? What's going on? Last time I saw you, you were doing this, what's up?' And then tears and so I thought, 'Okay, I'm not being aggressive. I'm not saying anything mean.'" But what I learned was I had created a safe space for them to talk. I understood them as a person, I understood their business, I understood how to build technology and the business space so they were opening up. But it was happening so much, I was going to my therapist and I was like, "This is too much crying in my life. I don't want to be the shoulder for everyone."

Kristen Cooper:                
And so, I kind of did the same thing that I did with Startup Study Hall. I made a list of all the problems that people kept complaining to me about. And then I took the list and this was like about 50 or 60 different issues and I took them to two therapists with PhDs in psychology. And they said, "This is interesting." They said, "Categorize these different problems." Kind of like in a hospital you're going through triage so I had to categorize them, which I did. And then I gave them back to them to do it the correct way. And so some things popped up, they were major issue with stress, anxiety, power, race and gender dynamics. There were also some issues around caregiving and the responsibilities that were more weighted with women than their male counterparts.

Kristen Cooper:                
And so what we knew for sure was that there was a lot of emotional suffering going on and nobody was really talking about it. And while I am the biggest believer that every human being on earth should have a therapist, there's a lot of stigma around mental illness and mental wellness. In fact, some people can't even call it mental illness. They need you to say mental wellness. So until we have a society that teaches humans from the time they just arrive until adulthood how to understand themselves the behaviors of others around them, we're going to keep bumping into one another and hurting one another.

Kristen Cooper:                
So it made sense to me that not only were we teaching the business of how to build a business in technology, we had to figure out what are the psychological problems that entrepreneurs are facing? And what can we do to create educational opportunities for them to better understand themselves and their employees and their investors and theirs boards and all the people that they're doing business with so that they can be healthier. And there's so much talk around creating healthy corporate cultures. And I think a lot of the expectations are completely unrealistic. Managers aren't trained to really understand human behavior, a lot of humans aren't given the opportunity to fully actualize. They're not given the opportunity to really show up as themselves where they go ...

Kristen Cooper:                
So there's all this suppression or I should say there are all these maybe unaddressed feelings that are suppressed and then how do you expect that person to come to work and inspire others and create safe spaces? It's impossible. So we don't really have a culture where we're talking about those things. And so we thought we can address these things. We can create a space where experts come in, break it down, talk about the chemistry that's going on in the brain, talk about the behaviors, help them better understand what and why they're doing what they're doing as well as the people around them. And then give them tools to immediately apply so that they can begin to feel differently about themselves and create relationships that are healthier.

Mike Kelly:                         
That's a great ... Man, I got so much I want to unpack there. Okay, before I go to the next question, I just want to share one story that maybe empathizes with your experience. So I'm a big book giver, it's one of my favorite things to do. If I have somebody where as a thank you or as a clear next up, if there's an immediate thing that I can pull a book off the shelf. Like if somebody's struggling with sales I'll give them Pitch Anything, if somebody's struggling with coming up ideas I'll give 'em Zero to One, whatever. Like that for me there's just I have this short list of books that I can give them and it makes me feel better.

Mike Kelly:                         
One of my complete go-tos when somebody is like in that early, messy stage of starting a business is Resilience by Eric Greitens. And Resilience it's really tough book to read. Greitens is a former Navy Seal who's writing a series of letters to one of his best friends who's dealing with alcoholism and coming back into life and stuff like that. And just beautiful areas of series of letters that touch on like economics and stoicism and philosophy and just life and how it's messy, right?

Kristen Cooper:                
Yap.

Mike Kelly:                         
When I read that book, I read it at the perfect time for me. It really hit me in the right way and I've tried to read it every year since. And so it's one of my go-tos when it's like after you and I have had a couple of meetings and you're like, "Yes, this is just really hard." And this would be the book I would send you but with a handwritten note of why. This has never failed me. Every time I send that book, I will get either a ridiculous letter back of like everything that's going on in that person's life, professionally and personally or a phone call.

Kristen Cooper:                
And I've seen your wall of letters. You have hundreds of letters on your office wall. Mostly thank yous.

Mike Kelly:                         
Or this ridiculous phone call where somebody will start sharing with me what's really going on in their life that's happening all behind the stress of a startup. And like for me, this is great for two reasons, one, in theory through a book I didn't even write. I got to help 'em out a little bit, which is at the time that they need it, which is great. Two, and more importantly, like selfishly for me this is affirming. Like, "Oh yeah. Then I'm going to figure out either." It turns out they're screwed up as I am.

Kristen Cooper:                
Equally broken.

Mike Kelly:                         
Yeah, that's right. Exactly. That's exactly right. Like let me just [inaudible 00:16:56] dear friend of mine, she said this great thing to me. I was struggling a few weeks ago and I was texting back and forth with her and she's like, "Look ..." She's like, "I'll just come there and sit with you and we can just wallow in it together. We don't even have to fix it." To me, that was just great ... It was like this is great visual of like here's somebody who cares about me enough to just come and wallow in it with me.

Kristen Cooper:                
Yeah, that's a good friend.

Mike Kelly:                         
Yeah, yeah. And so for me, it creates these moments of like, "Well, at least I can be there and wallow with 'em and help 'em through it." So anyway, like what that experience that you had, I think is not unique. It is probably a little bit unique but it's not unique to just this fear of entrepreneurs you're interacting with. I think that is a universal thing, the stress of trying to start a business for the first time and figuring out what that means and I'm now literally swimming upstream in all these different ways and it creates all these downstream problems because finances touch everything you do. Like they touch all your relationships, they touch all these obligations and if you're starting your own business, you don't have money. And so it just amplifies all the problems in your life and they're interacting with you at that time where everything has now been amplified. So anyway, I wanted to share that.

Kristen Cooper:                
It's hard, yeah. But that's awesome that you do that. We need more people doing that for people. What a great way to inspire somebody else. Send them a book and a note. I mean, that just makes their day. I mean, first of all, we get so little snail mail, so what a great way to make someone feel better.

Mike Kelly:                         
Thanks. Okay, so I wanted to jump a little bit based on the last thing you were talking about which made me ... And I know the answer to most of this but I actually think you might say some things that surprise me though. So what is Startup Ladies today like tactically? If I become a Startup Ladies entrepreneur or if I become a Startup Ladies investor, what is my experience? Is that a series of regular occurring events, is there technology there that I'm logging into, is there ... Like what is it today?

Kristen Cooper:                
Yeah. It's both of those things. So we continue doing the Startup Study Halls where tonight I'm going to listen to Ryan Brock who's the CEO of Metonymy Media and he's going to be talking about how you can really connect with your customers in a way it keeps them and you can be more predictive about what they want so you don't just retain them, you grow with them. And how you represent yourself and the story of the company is really important for the longterm. And so he's going to teach us that.

Kristen Cooper:                
And so many of our entrepreneur members as I mentioned, they're experts in a particular industry. And it's awesome that you've come up with a problem that needs to be solved but as you well know, there are so many different departments around solving that problem. Maybe you're really good at sales but what about the marketing and the technology and all those other things?

Kristen Cooper:                
So at Startup Study Hall, this is where you're not going to become an expert. However, you are going to increase your knowledge base so that you become competent and confident in yourself to make good decisions about different areas of your business that you know so little about. And the community is amazing. I mean, everybody always has a great story and so you're physically there with people and we also have a private Facebook page online so people share celebrations, they're sharing opportunities for funding, they're sharing articles and videos. And occasionally I get on there and complain about how I'd rather clean a toilet than do accounting. Like that tortures me. Like we're all good at some things and really dislike other things.

Kristen Cooper:                
So it's this space where you can just share it and not be judged and not feel less than because when you're in front of investors, oh my gosh, it has to be like the shiny penny version of yourself, and that's hard. It's hard to maintain that all the time. So we also launched an online learning platform that we call Startup Study Hall online in November. So we started recording the Startup Study Halls with these executive mentors and then what we did was spliced them, provided additional notes and templates. And then this also allows you to ask questions of our team.

Kristen Cooper:                
So we're going to use this tool to better prepare people to secure around a funding. So at some point we'll say you have to get through each one of these Startup Study Halls and the cool thing is we have a dashboard which allows us to see how they're moving along the system. So I know that they're learning and that they have the templates that they need in order to go from idea to market and to be better prepared for those conversations with investors. Because why would you be good at that? If you've not been trained, how the heck can you be good at that kind of conversation?

Kristen Cooper:                
So yeah, the combination of the in-person community here in Indianapolis and Terre Haute and Bloomington and then the Facebook page where we're talking every day and then the online learning platform, it's given us a lot of great ways to communicate, to learn and to grow together.

Mike Kelly:                         
That's awesome.

Kristen Cooper:                
Yeah.

Mike Kelly:                         
You had said earlier, I think the quote was 70 areas, 70 topics that you wanted to learn more about and that was one of the things that really sparked it for you. So like right now, what are the two or three topics that you have used the most jazz that you're investing time in personally and learning more about?

Kristen Cooper:                
Okay. Well, it's funny, I was just watching a show called Grace and Frankie and there was a scene where this, oh my gosh, if comes on and they're having this disagreement and Frankie says, "Damn it, I am going to be friends with you no matter what," even though they are at odds with each other because she likes and respects even when they're disagreeing. So I feel like I have that relationship with finances right now.

Kristen Cooper:                
While, I don't really enjoy it, I'm really interested in becoming good at multi year projections. It's something that you have to become enough at in order for investors to want to sign a check and hand over their money. So while I understand at a big picture picture level but I'm working in quick books on financial statements that I have not worked on before. It's not sexy, it's painful for me but I understand the benefit of it so I'm making peace with it and getting closer to it despite the fact that it's torture.

Kristen Cooper:                
I think the other areas that I'm curious about are opportunities to further discover how we approach conversations around mental wellness. I think that the platform we're utilizing, that we launched in November, can be a great place for people to dive deep on topics that they may be uncomfortable talking with a manager, with their friends, an investor, a board member. So it's a place where you can be in your PJs at home and do a deep dive on, "Okay, I'm really feeling a type of anxiety I haven't yet experienced before," and walking them through that.

Kristen Cooper:                
So I have a really deep interest in developing more curriculum around mental wellness and the challenges that entrepreneurs face. And then the thing that we were just talking about before the show I think most of my life I've wrapped up my identity in work. So on a personal level, despite the fact that I'm working like crazy to grow the Startup Ladies, I want the spend more time pursuing some of the fun things in my life instead of spending almost all of my time on the work things in my life. But if they listen to ... What's this podcast coming up with you and somebody else where you're telling like the really fun stories of yourself?

Mike Kelly:                         
Oh my, thank you for that. So the podcast is Know Indy, K-N-O-W. And they just did a phenomenal episode. Or it's typically a two-part episode, they just did a great one with Josh Miles. Well, formally from Miles Herman. Josh has moved on to his next thing and he talks about that in the podcast which is fantastic. I think he just did a really good job with that. So I will be on the Know Indy Podcast which is done by Steven Tyler probably sometime in February or March, I'm not entirely sure when it goes live. But my guess is it will be in the next few weeks.

Kristen Cooper:                
I think the important thing for your viewers to know is that you share things that people ordinarily would not know about you and they're so interesting.

Mike Kelly:                         
Steven did a good job of catching me flatfooted when we kicked off and so we went on a couple of tangents. It was beautiful. He did that very well.

Kristen Cooper:                
If you like a good story, I would tune in to that.

Mike Kelly:                         
Yeah. All right, back to you. And well done. Okay, so if I'm an investor, first, I'd love to hear the pitch towards investors. Why should I be looking at female-founded startups versus other startups? Like give me that quick investor pitch, just from a macro level perspective.

Kristen Cooper:                
So first, female founders get a greater return on investment than their male counterparts. And PitchBook just released the fact that in 2018 the percentage of VC tellers invested into women-owned startups went from 2.19 in 2017 to 2.2 in 2018. So the numbers are still really low. So one of the things that we talk about with folks that have the capacity to write checks for at least $5,000 are the specific obstacles that women founders deal with. Then we talk about how we're addressing those problems. We also share how we're preparing the entrepreneur to be ready for investment and to lead a scalable startup, which gives the investors confidence. And then we put them together.

Kristen Cooper:                
And so it's actually really easy because we live in this me too era where you have a lot of women, especially over the age of 50, they've made their nut either by a successful career, maybe they inherited some money but they have disposable income and they've got the passion around wanting to see more women start up scalable businesses. So really, it's not difficult to convince people to want to do this, it's just leading them to the opportunity and providing the education so that they can invest in women-owned startups.

Mike Kelly:                         
And if somebody is listening and this isn't a wrap up, just feels like a good time to do it, if somebody is listening and they're interested in becoming an investor, perhaps even as a first-time investor, how do they get plugged into the community or with you to start that conversation? Get involved in one of the investor one-on-one sessions, things like that. What's the best way for them to do that?

Kristen Cooper:                
Visit the website, thestartupladies.org. Send me an e-mail, my e-mail address is Kristen, K-R-I-S-T-E-N @thestartupladies.org and we would be happy to invite you to a Startup Investing 101 so that you can meet fellow investors and learn how to invest and then we'll introduce you to some of the most talented women solving really big problems that have large total addressable markets that are going to generate some really significant revenue.

Mike Kelly:                         
Awesome. Flip that, so now if I'm like ... At what stage if I'm thinking about starting a business should I be engaging with the Startup Ladies community? Is that like don't bother coming unless you've already taken the leap and you're now jobless and destitute and trying to figure out how you get a product to market. Is it like, "No, it's something I'm interested in doing but I don't even know whether I would do it yet." Like how do you or who do you welcome from the community? I mean, I'm sure you welcome everybody but what is the best way for different people along that path to engage in the community?

Kristen Cooper:                
So the best thing to do is to register for a Startup Study Hall and keep showing up. If you are a part of a community then people know when you're there and they know when you're not there. And so if you keep showing up and you keep learning and you keep connecting, you're going to feel better 'cause you've got new friends. You're going to be stressed because you're surrounded by people who are a few steps ahead of you and you're going to be learning. So some of that fear you may have about starting up a company is replaced by knowledge and that's really powerful.

Kristen Cooper:                
So whether you're thinking, "Gosh, I really wish I was doing something different, I don't know what," you're a good candidate. If you're noodling on an idea and aren't quite sure if the idea is viable or scalable, come to a Startup Study Hall. If you've started the startup and you're stuck or you're stalled and know you're going to need investment, you definitely need to come. And then those folks that are scaling companies like Marcia Haut who has sold a couple hundred thousand women SmartNoggin Stik. She creates toys that help children develop their fine motor skills and learn object prominence. She's growing with us. So we have so many different types of ideas, products and service companies that are involved. You will learn, you'll grow and you'll connect with some pretty amazing people.

Mike Kelly:                         
That's awesome. You said a quote in there that I wrote down because it's an amazing quote, "If you're part of a community then people know when you're there and when you're not there," that's fantastic. How have you ... So let's talk about your scale up story, started here in Indianapolis, have chapters in Terre Haute, Bloomington and I'm sure plans for world domination. What is it like trying to expand what it largely a physically community to other physical spaces 'cause that's not an easy thing to do. I'd love your experiences in doing that and maybe some of your thoughts on how you're going to continue to do that in the future.

Kristen Cooper:                
So we did a macro and a micro level expansion study this fall. And at first we took a look at things like populations, the way Kauffman Foundation determines what a viable startup ecosystem is, the number of funds that invest in women and minority owned companies, the number of companies that have women in the C-suite and on boards. And there were several other pieces of criteria that we looked at at a macro level to determine is this an environment where women are celebrated, supported and invested in?

Kristen Cooper:                
Then we dove deeper and we identified 15 cities and then we started really understanding who the movers and shakers were, who were the developers, the coworking spaces, the funders, the law firms, the players. And the combination of the macro and micro study help us determine what cities that we would go into next that are very similar to Indianapolis.

Kristen Cooper:                
We also have learned that you need a leader who's going to be the face of the organization who's kind of like the person that ... Like when you go to a networking event and you're so glad that they're there because you know that you're going to be comfortable around them, you need that person. And they don't have to write the best code or know everyone, they have to be comfortable in their own skin and make other people feel welcomed and that they can truly be themselves. That person is going to help draw other people in and that we've done well. Shelley Klingerman's our leader in Terre Haute, Danielle Wolter Nolan is our leader in Bloomington. They both have all of those personality characteristics and they're naturally good connectors.

Kristen Cooper:                
So what we do is we begin with a small team of volunteers who are well connected and then we start inviting people kind of thinking in terms of orbits and the levels around the center, like the sun. So Shelley and Danielle are the suns in those areas and then we have lots of planets and stars floating around them but you keep drawing people in and that's how you build a community. And it's very similar to anything else. You may have an interest in music or painting or martial arts or dog rescues, whatever the thing is that you're interested in, there are plenty of other people around who are also interested. But if you have that shiny person there that's going to make you feel comfortable, they welcome others in. And we have the structure and we have the curriculum, so that's the easy part. It's finding those special people that can be the center of the network.

Mike Kelly:                         
Super interesting. As you were talking, I was replaying a conversation I had in one of my peer groups. I'm in a group of a bunch of other consulting companies like ours from around the country and a couple years ago at one of our meetings we were talking about office expansion. So how do you open up a new consulting business in Chicago or a new office in Atlanta or something like that? And I want to say we're pretty mid-sized for that group. There are some companies smaller than us, a couple of companies bigger than us. It's just the perfect place to be 'cause you can share some experience.

Kristen Cooper:                
If you mentor and [crosstalk 00:34:50]

Mike Kelly:                         
Yeah, exactly. I feel bad for the guys at the top end where it's like, "What are all you idiots doing down there?" Like, "We're here to learn from you buddy." But while we were talking about office expansion, from the people who've done it they're pretty much, "Look, there's two ways to do it. You can go and buy a smaller consulting company. Find that five to 10 person firm, acquire them. They have a reputation, they have talent that hopefully if you're doing it right, if you're buying the right firm that they have all of these things that you're going to need that you can now build off of. And you're bringing them a bigger brand which is going to accelerate their growth and it's just a lot of good things there. Or you can go in and try to spike the office from the ground up by trying to get the sun. You have to find that one person who in the market has such a strong reputation that they are a magnet for the type of talent that you want.

Mike Kelly:                         
Because if they're not and you're trusting Indeed job postings to bring you talent, then you're not going to be successful. And everybody who is bigger than us, who has done this, shared stories of, "Yap, we went into this office and it failed and we can point to the fact that the very first developer that we brought on staff they weren't that person. They weren't the person that ...

Mike Kelly:                         
And again, to your point, it has nothing to do with it's about being the smartest best developer in the room, it's less about that. It's more about their ability to be a connector in the community and attract that talent to them. And it is amazing that while you're saying that, it's the exact same thing that they were saying. And like, "No, if you want to expand to new geographic markets and you want to do it in this organic way, you have to go find those people. There's no other way to do it."

Kristen Cooper:                
And the good thing is they really stand out because when you start talking with people in the market, their name comes up over and over again. "You should talk to so and so. Have you talked to her yet?" So it's just for the validation that there are a couple of people that keep popping up in conversation and those are the people that you want to keep close to you 'cause they're the ones that are going to help you draw more people in.

Mike Kelly:                         
Right. Great. Switch gears just a tiny bit, I would be interested in ... So you mentioned accounting earlier and then maybe some other fun personal things, what non-work related fun thing are you learning right now?

Kristen Cooper:                
Okay. I can't say I'm learning, I can say I'm practicing.

Mike Kelly:                         
Love it.

Kristen Cooper:                
So I paint and my basement has a section where we're sitting at this countertop raised seat area in this cool boardroom at developer time. And my space is like an uglier-

Mike Kelly:                         
Coderoom is generous.

Kristen Cooper:                
My basement is an uglier version of this with canvases and paint all over the place. So I'm working on a painting that for me was a latch. Not compared to the story you were telling me before but Mike once did a chain-sized giant sculpture. What did you sculpt by the way? You didn't show that.

Mike Kelly:                         
No, we're moving on.

Kristen Cooper:                
Okay. Well, that should be its own podcast.

Mike Kelly:                         
It's in my show dang it, you got to start your own podcast.

Kristen Cooper:                
So I'm working on a painting that is ... It began from a photograph of my brother and I. We were lifeguards together when we were kids. And someone took it from a high dive so looking down over us. We were floating. And my head and feet are one way and Scott's are in the opposite direction. So it started as that, I tried to paint it and I did such a miserable job at it. My husband actually commissioned one of his friends to paint this. And to me, it's one of my fondest memories of my brother. And also swimming and swimming had such a profound effect on my life. And while I'm a better swimmer than the average Jane, compared to real athletes, man I am the lastest. But the metaphor different swimming situations for me has been life-changing and has been amazing.

Kristen Cooper:                
So the painting I didn't create but I had the canvas that I had messed up on and I love when you have a messy painting that is hideous, that becomes the foundation for something else. So now I'm using the background and I like to use a paint scraper and so I'm using that as a background and I'm putting layers of other things. And I really like abstract painting. I think it's very difficult to do. I'm not a skilled painter, I'm not trained but I found a painting that I started painting from. It looks completely different now but I am trying to work on that canvas and it's about three feet by four feet. So that'll keep me going for a year.

Mike Kelly:                         
It's a good-sized canvas.

Kristen Cooper:                
Yeah. So every time you go downstairs to get like, I don't know, like a can of beans, I might just play with it a little bit. So it's a fun thing to go and keep building.

Mike Kelly:                         
That's interesting.

Kristen Cooper:                
Yeah.

Mike Kelly:                         
I never felt like with painting I could tinker. I always felt like I needed to commit time so you don't have that. Like you're comfortable just being like five, 10 minutes in and out.

Kristen Cooper:                
Yeah. But I will say when I go to like a Wine and Canvas, it's typically a very social thing. And I, by nature, am a very social person except when I get to Wine and Canvas. I would prefer silence and that no one talks to me because we-

Mike Kelly:                         
You're the person with both headphones on at a Wine and Canvas.

Kristen Cooper:                
That's a great idea. I'm going to do that next time. But the teacher is very clear about what we're going to paint and when I look at it, I've decided what liberties I'm going to take. And then I'm at it for the three hours. And 100% of the time I'm behind everyone in the classroom until I get what I want to do. And then by the end, I'm usually the last one up but man, I pull it together. And I have been genuinely satisfied with everything I've done at Wine and Canvas. Of all the ones I've done, I have only gotten one approved for the wall, the rest just became foundational paintings. But I will say the exercise is really satisfying.

Mike Kelly:                         
The pottery places where you can go and pick a piece of pottery and paint it and they'll fire it for you and all that stuff, my wife has banned me from those activities. I'm not allowed to go anymore.

Kristen Cooper:                
Oh no.

Mike Kelly:                         
'Cause the last time we went, she painted like an ashtray or something, I don't even ... That's probably not, spoon holder 'cause we still have it. She painted a spoon holder which took her like a normal human amount of time, like 45 minutes. I spent 60 hours on a bowl that ... I mean, we still have it and it is pretty cool but she's like, "No, I'm never doing this."

Kristen Cooper:                
Could you just keep changing the idea around what you want?

Mike Kelly:                         
Nope. It's all just the execution, meticulous execution of the original idea and I'll text you a photo of it or something but it's ... I mean, it is really cool. I'm very proud of it but she was like, "No, never. I'm never doing that again." 'Cause ...

Kristen Cooper:                
Didn't it just feel good doing what you were doing?

Mike Kelly:                         
Yeah, I loved it.

Kristen Cooper:                
Because nobody's going to suffer, you can't screw it up, nobody doesn't get paid if you don't do it, right?

Mike Kelly:                         
Yap.

Kristen Cooper:                
You can just play with it. It's just pure play. I love that about painting. I once spent two and a half hours with my favorite painter on earth, Rebecca [Allen 00:41:50] who's in New York. I'll connect you with her the next time you go. She has this amazing gallery in The Bronx. We spent two hours mixing one paint color. And granted, she could do this much faster but for me, matching a color, doesn't matter what it is, I ... And you're somebody who's pretty meticulous but I'm talking like match it identically. We had more fun mixing different colors because every time we use either a different brand, acrylics or oils, it's a totally new color scale. So matching color was just ... It's more fun than I've had in ages. I could do that with a master for a very long period of time. I don't know how much we'd produce together but the exercise itself of mixing the color I find completely cathartic.

Mike Kelly:                         
That's cool.

Kristen Cooper:                
Yeah.

Mike Kelly:                         
All right, I'm glad I asked that question. Best business related book you read last year or listened to if you're an Audible person.

Kristen Cooper:                
Yeah. Scott Jones talked to me about the entrepreneur operating system and traction. And I found a lot of the ideas interesting. However, I am not going to thumbs up or thumbs down until I talk with people that have implemented this because I am a skeptic. I would like to be proven wrong but I don't think I will. So those two gave me lots of good ideas. I'm always happy to learn from somebody who thinks it's a-

Mike Kelly:                         
I think you're going to be proven wrong.

Kristen Cooper:                
Have you done like a Level 10 Meeting?

Mike Kelly:                         
I have not but I have lots of people in my network who swear by it. I was at a luncheon today where two of the founders in the room use it. There were just like preaching ... Literally one of the people was handing out Traction books, she was such a big fan, to transform her business. There's lots of people in that peer group I mentioned that are pretty big fan boys. I've read the book a couple of times. I've never-

Kristen Cooper:                
A couple of times?

Mike Kelly:                         
Yeah, I've read it twice. Well, because I read it ... I actually read it like ... You know that book has been out forever. Even though it has become ridiculously popular in the last 24 months, it's been out forever. So I read it when it-

Kristen Cooper:                
Who made it popular?

Mike Kelly:                         
I don't know.

Kristen Cooper:                
like, "This is our new thing. We're all paying attention to it right now."

Mike Kelly:                         
I have no idea. But I read it years ago and probably forgot it 'cause ... Which is one of my problems. I read so many books like you can't ... Anyway, I can't retain it. So I didn't retain any of it and then when it became popular again I was like, "Hey, what was that book about?" Like I remember concepts, like the accountability [inaudible 00:44:26] an accountability chart. So some of that stuff I remember and I was like, "Okay, well I ..." Like it was good. I thought it was a good book and I read it at the same time that I read ... What's the bakery, the apple pie bakery and it's one of the work on your business not in your business. I can't remember the ... It's one of the seminal-

Kristen Cooper:                
I don't think I might have read it if it was about apples. If it was chocolate I would have read it.

Mike Kelly:                         
No, it's one of the seminal books in building your business, I'm butchering this. But anyway, I read it the same time that I read that book which a bunch of people said I should read so I did, didn't blow my hair back but it was fine. So then it becomes popular and I was like, "Okay, I got to read this again." So I read it again, maybe-

Kristen Cooper:                
And it was so good you can't remember its name.

Mike Kelly:                         
No, no. Traction I read a second time.

Kristen Cooper:                
Oh, okay.

Mike Kelly:                         
No, I didn't read the ...

Kristen Cooper:                
The apple book.

Mike Kelly:                         
The other book.

Kristen Cooper:                
Yeah.

Mike Kelly:                         
It's one of the business fables. It's where like she's opening a bakery so the book is about how she gets stuck working in the business and never takes time to work on the business and so it never scales and that kind of stuff.

Kristen Cooper:                
Speaking of which, do you know that in Indianapolis we have a store that just sells burnt cakes? That's all they sell.

Mike Kelly:                         
Really?

Kristen Cooper:                
Yeah. It's at the mall.

Mike Kelly:                         
How long have they been in the business?

Kristen Cooper:                
I think they opened in the fall but they are, no joke, it's franchise and there's about 300 of them in the U.S..

Mike Kelly:                          That's not real.

Kristen Cooper:                
Burnt cakes.

Mike Kelly:                         
Not real.

Kristen Cooper:                
It's real.

Mike Kelly:                         
No.

Kristen Cooper:                
I mean, they have a storefront and all they sell are burnt cakes.

Mike Kelly:                         
I've no date to backup my belief but I just believe this in principle.

Kristen Cooper:                
I mean, I'm not offered burnt cake that often so I'm not sure what flavors are available in burnt cake. I'm open.

Mike Kelly:                         
Well, they're going to change that. That's awesome.

Kristen Cooper:                
Yeah.

Mike Kelly:                         
All right. So Traction, I think I'm going to try it in one of our businesses. I think I'm going to ... I made this-

Kristen Cooper:                
That would be great because then I can ask you how it works in real life.

Mike Kelly:                         
We'll see.

Kristen Cooper:                
Okay.

Mike Kelly:                         
But I have met enough people who are like, "Yeah, it's real."

Kristen Cooper:                
Yeah.

Mike Kelly:                         
That I'm kind of like, "Okay, I should pay attention. I should at least experiment with it."

Kristen Cooper:                
Yeah.

Mike Kelly:                         
Yeah. So I think I'm going to experiment with it.

Kristen Cooper:                
Okay, cool.

Mike Kelly:                         
All right, good answer. I like that. What is the biggest loss that ... When you look at ... How long have you been doing the Startup Ladies?

Kristen Cooper:                
Over four years now.

Mike Kelly:                         
All right, over four years. When you reflect on missed opportunity, what are maybe the number one or two stories that come to mind?

Kristen Cooper:                
I should have made it a for-profit membership LLC sooner, I should have started charging sooner, probably could have done that a year into it if not before then. And I-

Mike Kelly:                         
And why didn't you? Why didn't you do it sooner? You didn't think people would want to pay, you didn't think it could be a real business, it's just not on your radar.

Kristen Cooper:                
I don't know that I was fully thinking like a CEO in year one. I think I was just trying to build relationships and solve problems. I didn't realize that building a business was the format for building relationships and solving problems. So I would have, like I said, charged sooner. And then I think I would have figured out my financials sooner because we generated revenue in year one. I paid myself last year. What tech company does that in year one?

Mike Kelly:                         
That's awesome.

Kristen Cooper:                
Yeah. So I can show how we're, especially at this time ... I mean, thank you feminists that have come before me. You've created opportunities so now that women are taken very seriously. More women want to take risks and build scalable startups and more women are in positions to write checks, to resource those startups. So thanks to all of those factors. We now live in a time where I should and all the Startup Ladies should be successful. So I wish I would have had my financials in order to raise more money earlier on because what we could do if we had a couple of more staff, I mean, it would be historically transformational. And we're changing Indiana history right now. And I can't wait for us to be able to do what we're doing in other states.

Mike Kelly:                         
I'm in on that. That's amazing. All right, thestartupladies.org?

Kristen Cooper:                
Yes.

Mike Kelly:                         
That's right? You have meetings mostly Wednesday nights, is that right?

Kristen Cooper:                
Indianapolis.

Mike Kelly:                         
In Indianapolis.

Kristen Cooper:                
It's the first and third Wednesday and then in Terre Haute and Bloomington that changes and that's completely dependent on what those communities want to do. So I look forward to meeting folks at Startup Study Hall sometime soon.

Mike Kelly:                         
Thank you for coming on the podcast.

Kristen Cooper:                
Thank you Mike.