Kirsten Moorefield never intended to start a tech company. Yet here she is, the co-founder and C.O.O. of Cloverleaf, an H.R. tech platform that allows individuals and employees to be their best selves both at work and at home. She sat down with us at Rhinegeist Brewery – back where it all began in 2015 – to chat about her journey as a tech entrepreneur; the many, many challenges along the way; finding her support network; and what it means to be a female leader in this space.

Entrepreneurship journeys look different for everyone, but one thing is certain: When it comes to making something out of nothing, the journey IS the job. To kick off our year-long series sponsored by Main Street Ventures, we dove into the journeys behind five woman-owned Cincinnati businesses.

Interview by Gina Regan. Photography by Chelsie Walter.

Tell me about yourself.

I was born and raised in Cincinnati. I hated the winters, so I peaced out and went to North Carolina for college. I grew up as a wonderful rule follower. I never sold candy bars like some of those stereotypes of entrepreneurs. I didn't even do the magazine sales. I was terrified of selling. I felt like, “Why would I knock on people's doors and have them say no to me?”

I definitely saw problems in the world, and I wanted to solve them. I thought the best way to solve them would be through mission work or nonprofit work. I went to college to study what's wrong socially and economically in the world, and I came to the conclusion that nonprofit is just not the right way to solve the problems that I care about. I wanted to do it through business, which was surprising to me because previously I had thought that business was all greed and big conglomerates. But I realized that it's a really powerful method to solve problems in the world.

I couldn't find a business I wanted to work for. I heard a story about a guy who started his own business. He did not come from "that" family. He did not have money. He had zero business experience and he started a business that became really successful. All you gotta do is file for an L.L.C. and if you don't even know how to do that, you just Google it. It blew my mind.

I decided to go work for another business to learn some things, but that seed was planted. I left that job when I had my first son, and for some reason, when he was about six weeks old, I decided it was time to start a business [laughs]. I was sobbing to my husband saying, "I'm not a stay-at-home mom. I'm going to start a business.”

He very lovingly was like, "Let's pray about this for two weeks."

I was like, “Okay, but I'm going to do it.”

And the next night I came to Rhinegeist for a going away party for someone I used to work with, and I ran into another guy I used to work with: Darrin Murriner. He said, “What are you up to?”

I said, “I want to start a business.”

He said, “I'm starting a business! Come along with me!” So that's how it all started. That was in 2015.

At that point, had you any inkling of what kind of business you wanted to start?

Absolutely. I knew what kind of business I wanted to start, and Darrin was not starting that kind of business. I actually said, “No, but thank you. I'm so flattered.” But then I thought about it for a couple more weeks, and I realized that it was something that actually can change the world. So I joined forces with him, and we applied for OCEAN Accelerator. We got rejected, but Scott Weiss, who runs it, gave us great feedback, offered to mentor me, and we spent the next year interviewing potential customers.

I had no income, therefore paying for childcare was impossible. I was just trying to hustle through naptimes and things like that. It was a terrible experience, but I got out enough to do a lot of potential customer interviews, talk to some investors. We invested a couple thousand bucks in a developer overseas, and he built out a Minimal Viable Product for us. It crashed a lot. It had broken English, and Ukrainian error pages. It had its flaws, but we learned so much. People started paying for it, so we reapplied to OCEAN Accelerator and got accepted.

We started fundraising, and that was interesting. I never thought I wanted investors in a business because I had heard horror stories like, "They kick out the founders. They force you in the wrong direction." I do believe this happens, but there is a whole different side to it where the investors have actually been really helpful to us. We started fundraising around April 2017 and we didn't close until February of the following year.

That was a hard 10 months. After accelerators, there’s this thing called “the Valley of Death” where many startups shut down, because you don't yet have enough traction to earn enough money to support the founders or to prove to investors that this is something they're ready to invest in. And investors don't invest in you after they meet you; they invest in you 6 to 12 months later because they want to follow how you make your decisions, what progress you make, how you handle the hard things.

I truly believed that when you're on the right path, the doors open for you, and that's just not true. Sometimes you have to force your way through.

The summer after we graduated from OCEAN Accelerator, when we were in our “Valley of Death,” we had the hardest things happen to us. Darrin's house started flooding; his roof blew off twice; his transmission went out on his car. I had a miscarriage. My transmission went out on my car. I had another miscarriage. It was like punch, punch, punch. We didn't have an income at this point, and the revenue our company was making we were sending overseas to our developer or paying for marketing support to an hourly employee. It was just a really, really hard time. Thank God that Darrin Murriner is eternally optimistic, and we pushed through and got some really great investors who believed in us and funded us. In February 2018, we started hiring a team and rebuilt our entire product.

Since then, we've just exploded in terms of user base. So, yeah. It was a very painful, hard time, but the thing I want to get across to people is that I truly believed that when you're on the right path, the doors open for you, and that's just not true. Sometimes you have to force your way through. Sometimes the thing that's really painful isn't the sign of a closed door. It's the sign of a jammed door that you need to push. I want more people to know that even when it gets really, really hard, you can still push through and get to success on the other side. And success will look very different than you expected it to, and oftentimes it's better and so much more rewarding because you pushed through.

What is Cloverleaf? Why does it matter?

We are an H.R. tech SaaS – software as a service – platform. We have the technology that partners with assessment companies – think DiSC or 16Personalities – and we enable those assessments through our platform. So it's a much more user-friendly experience for the end users who can come learn about themselves, about how they can do their best work, about how they can be better in relationships. We offer an individual package where they can have ongoing coaching delivered to their calendar, their email, their Slack, where we can teach them, “Here's how you can lean into who you are wired to be.” Then we have a team package, where teams can better learn to work together. They can take that information about themselves and about their team leads and say, “Okay, so when Joe is asking me all these questions, he's not challenging me. He's poking holes to find out what the best solution is, and that's a good thing.”

We also have a slew of features for managers to learn how to have better performance management conversations. We have features that allow them to see across the data of who is a high performer and why, what's their thinking style, how to do better career pathing, and all kinds of big issues enterprises are facing with their people today, especially with unemployment as low as it is.

Why does it matter? Gallup has been doing their workplace engagement survey for 19 years now, and for 19 years, they’ve found that two-thirds of the U.S. workforce is disengaged, so obviously that means they're not producing their best work, and that's costing billions to the economy, and this really matters. But it also means that they're not satisfied. They're not fulfilled in the work that they're doing. We believe that work is satisfying. Work is energizing when you're doing what you're wired to do. There's work to some that is draining, but to others is exciting. We want to help people see that about themselves and their co-workers. We fundamentally believe that you can only go so far unless you're in a good relationship with your team. And you multiply everyone's potential when you have a high-performing team. So that's why we think it really is valuable to the world, and matters.

What has your experience as a female entrepreneur been like?

The hardest part for me, personally, about being a woman and an entrepreneur is being a mom. I think being a mom is hard for everybody, but when you don't have an income and you want to work, that's really hard because I would never sacrifice the well-being of my children and put them in a place I'm not comfortable with. In that phase, when I wasn't getting paid for most of the beginning of Cloverleaf, I just sunk so much of my time into trying to figure that out, balancing favors and family members. Things fell through a lot.

But I hope nobody reads this and thinks, “Then I just have to wait until after I start my business to have children,” because I don't believe that. While it was incredibly difficult, I would never change that I had children at the age and the time that I had them because I think that they make me a better leader, by far. They force me to disconnect when I go home, which I think is really good for my business and my team. I would never change that, but by far, it is the hardest part.

I hope more women see it's possible and that they can do it.

When I was in OCEAN, I said to one of the staff there, "I'm the only mother I know doing this." So she connected me with another woman, a mother, who was in the tech industry, and that was Christi Brown of iReportSource. Christi and I got together, had a great conversation, and decided, "Let's try to find more women doing this." Christi emailed Cintrifuse; Cintrifuse connected us with a couple; I emailed them all and said, “Hey, we'd like to form a group of women who are tech business leaders who want to talk about the full journey of starting a business: the emotional roller-coaster, the family challenges, the whole aspect of starting a tech company.”

We had, like, six opt in, and we still meet today. We've been meeting for over two years. We meet twice a month, and just talk about the real side of things, and I think if I didn't have that group, I'd have more to say about how hard it is to be a woman. They're supporting me and challenging me and they're here for me. We have an ongoing text thread: “Hey, who do you use for background checks? Who's your accountant? Oh my gosh. Today's a really hard day. Can someone call and just support me?” It's everything. It's the practical and it's the emotional. It's just the real-world side of doing this.

When we first got together, I asked the women, “Why are you here? What do you want to do in this group?"

Everyone said, "I want friends who get it." Because we all had friends who were stay-at-home moms, who were in the corporate world, who were working for small businesses. We had friends and family members across the gamut, but none of us had friends who were trying to found a tech company and invent something from nothing, and that's just different. We wanted people who we could say, "We just landed a lead investor," and for them to know how huge that is. So I think that's also a huge benefit to that group, and it would have been really hard for me to not have friends who understand it. Whereas men, there is just a higher population of men going for it and doing things and taking risks and figuring it out along the way than there are women, unfortunately, and I hope we change that. I hope more women see it's possible and that they can do it, and that when it's hard and when they fail, there is a lesson to learn and growth to continue on.

Do you have any advice for how to find mentors, and how to create this type of network that you have fostered?

Speaking out loud is so powerful, and people undervalue it. We think a lot in our heads without saying it out loud. It's because I said, “I don't know another mother who is doing this” that the group started. Any mentor I've had, I've had to verbalize: "I would like you to mentor me. I want your advice. Can we meet for coffee?” And you know, a mentor doesn't have to be someone who you say, "Will you please enter this long-term relationship with me and meet with me once a week, yada yada." A mentor can just be, "Hey, I'm heading up product now for the first time in my life. I need some help. Investors, do you know anyone who's doing really well in this area?” They make a connection. You just meet for coffee, and if it goes really well, you say, “This has been super helpful. Thank you so much. Can I reach out to you again in the future?” Which is a real life example of what's happening right now in my life, and that person has given me an incredible wealth of knowledge. You just have to talk about it out loud, and you have to do the very, very, very uncomfortable thing of asking for help.

Tell me about an influential woman in your life.

Kathy Beechem. I heard her speak years ago during a time in my life when I was looking for female mentors, and I thought, "Wow, if someday I could have her as a mentor, that would be amazing." Fast forward a few years: We got into OCEAN Accelerator, and she was on their board. We got connected and she agreed to start mentoring me, and I'm just so grateful I had the guts to ask her, because I admired her so much, and I thought, you know, total imposter syndrome, but she had opened the invitation to anyone in OCEAN if they wanted to meet. I am so, so glad that I did that, because in January she was diagnosed with lung cancer, and by March she had passed away.

Any meeting with Kathy was lightning. The first meeting I had with her, when we sat down, she had pen and paper, and asked me about my life, and within 20 minutes, she knew my deepest, darkest secrets, my biggest hopes and dreams. And she received it with care and with respect, and then challenged me on where to grow next.

I want to be the kind of leader that challenges people to become more than what they have been, and to accomplish more than they think they can.

She was a woman who fully went for it in life. Not just in business, not just in personal life, but in every conversation. If she was too blunt, if she was misperceived, she wasn't afraid of that. She actually, every morning, spent like an hour and a half praying and reading and repenting, which to her meant thinking over the last day and asking, "Is there anything I did that I don't feel good about?" And then she would text people. People notoriously got texts at 5:30 a.m. from Kathy Beechem saying, "Hey, yesterday I think I was a bit harsh to you. Sorry about that. Will you forgive me?" And I just love that because she didn't hold back in the moment, but she also wasn't afraid if she realized she had crossed a line to then go back and apologize. She was able to be very momentous and forward moving and successful and influential and impacted so many lives, and even when she challenged you, you felt honored that somebody saw you, cared about you enough to tell you, "You're wrong. Think this way. Try this belief. Go in this direction."

What kind of leader do you want to be?

First and foremost, I think about my home. I want to be the leader in my home who is present, never in a rush, who is unashamed to outsource work. I don't know if this is my American “pull yourself up by your bootstraps” mentality, but it's been difficult for me to come to terms with hiring help in my house. But I want to be the person who confidently leads my home, understands my strengths, leans into those, and doesn't feel the need to compensate for my weaknesses. I know my greatest accomplishment will be the relationship I have with my children, and the confidence that they have being raised by me, their resilience, the ability to face hard situations.

And by the way, I don't think this is a woman's answer. I think men should also think this way. People say, "Oh, don't ask that woman about her home life. How derogatory to ask her about having children." I think it's part of me, and it's part of Darrin, who is a man, who has children, who loves his wife deeply, and thinks about these things in his home. I think more people should ask him about it, because he has great lessons to teach.

Then I want to be that same leader in my business. I want to know my strengths. I want to be unashamed of my weaknesses and my need for help in certain areas, and I have such high respect for people who are good at what I'm not good at. I want to hire people who are smarter than me in all of those areas. I want to be unintimidated and unafraid of my business growing beyond my capacity. I want to be open-handed in saying, "This can grow so much more if I give freedom to my people,” if I am never in a hurry in trying to force people into what I think needs to happen before I honor what they have to say and their opinions. I let them take risks. I trust them and I reward them and I challenge them like Kathy Beechem when things go wrong. I love Brené Brown's definition of a leader, which is someone who “takes responsibility for finding the potential in people and processes, and who has the courage to develop that potential.” I just love that definition because I think a lot of us believe that a leader is strong-handed and says, "I have the answer. This is what it is. Go do these five things” – which I think is very limiting. I want to be the kind of leader that challenges people to become more than what they have been, and to accomplish more than they think they can.

There is no single definition of an entrepreneur. Check out our year-long series, "This Is Entrepreneurship." Sponsored by Main Street Ventures.

This Is Entrepreneurship: Cloverleaf’s Kirsten Moorefield