Some entrepreneurs have everything planned out, and when the time comes, they’re ready. As we sit in a tiny Oakley duplex surrounded by stacks of pads, perineal sprays, sitz, and more, Jess Kerr tells us she was not one of those entrepreneurs.

The postwell journey started with a moment of frustration on behalf of a friend struggling through postpartum recovery. What came next can only be explained through the perfect storm of a viral internet story, a stack of plain white boxes, and a woman determined to solve a problem.

By day, she works with startups at local accelerators The Brandery and gBETA. She comes from a family of eBay entrepreneurs, and she’s hilariously real (she told us she once thought “hot yoga” meant “you built fire from within”). Without further ado, meet Jess Kerr.

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 Kiersten Wones. Photography by Chelsie Walter.

Getting right to it, your tagline is “Childbirth is a mother.” Can you give us a glimpse into where that grab-the-issue-by-the-horns attitude came from?

I came up with that in like an hour because I was so in a crunch to get these boxes online. All these people were asking for them. The only people looking at these boxes were my pregnant friends who were very open about what they were going through, so I made it funny. And then the more people that saw it really liked it – it’s such a taboo thing; nobody talks about it… Why?

If you get a postwell box, you’re added to this closed Facebook group. And it’s so interesting because I’m a part of public-facing mom groups on Facebook (even though I’m not a mom), and people are like, “This is really embarrassing… But… I just don’t know if anyone’s experienced this?” It’s very beat-around-the-bush.

But in this Facebook group for postwell, people will just be like, “How long did your nipples leak after you gave birth?”

They’ll just straight-up ask, and all these moms will comment, like, “Four weeks!” “I had to sleep with these big pads in my bra every single night, and I had a tarp under our sheet ’cause I sweat so much!” They’re so honest. Everyone has already gotten this box, so they’ve gone through it or are about to go through it. It’s amazing.

Take us through the famous “aha moment” and the postwell journey so far.

I’ve hated going to baby showers for a long time. I remember getting my best friend’s sister onesies that had days of the week on them. She never even used them. Those onesies were my go-to gift. I’m at an age where a lot of my friends are having kids, so I just bought a bunch of those and would just give them and know that they may or may not ever be taken out of the package, and that really bothered me.

Everyone’s been to a baby shower: You sit around this one person, and they open all these gifts, and it’s all this stuff for the baby, and it’s so cute. And it can be cute – there’s nothing wrong with that – but I just remember thinking, “Nobody ever gave her anything for herself. Not a gift card; no slippers, socks, whatever.” That bothered me.

Four million kids are born every year in the U.S., but nobody talks about it. Why are we embarrassed to talk about it when all these people have this experience that other women could learn from?

But I gave her my onesies, and then two months later, she had the baby. On the way home from the hospital, she had to go to Target. The hospital gives you stuff after you give birth, but it’s not the best stuff, and it’ll last you for like, three days. She was leaking from every part of her body, and was in all this pain, and didn’t know she was going to rip as much as she did, so she went to Target with her boyfriend and the baby straight from the hospital. She didn’t go home first at all – she was in that much pain. And she called me and my friend, and she was just sobbing. She was like, “I don’t even know what to do to help myself.”

I immediately felt guilty – like, “You didn’t need what I gave you. You could’ve used a bunch of mesh underwear.”

Our suggestion was, “Just walk around the baby aisle and find a mom and just ask her what she used,” right? “Just ask someone who just did it.”

And she was so embarrassed; she was like, “I can’t just go up to someone and ask them about this. I can’t do that,” and I was like, “Why? Why do all these people have this experience?” I mean, childbirth is such a common thing. Four million kids are born every year in the U.S., but nobody talks about it. Why are we embarrassed to talk about it when all these people have this experience that other women could learn from?

I was just upset after that happened. I couldn’t stop thinking about how wrong that was. A lot of my friends are nurses and doctors, so I started interviewing them, and I would interview moms – I would get my hair done and interview every mom there and just start writing things down. It was crazy: It was the same 10 things that every single person said that they needed. I interviewed hundreds and hundreds of people, and it’s like, “Why isn’t there a whole kit you can buy with all this stuff in it? Why did I have to do all that digging just to find these 10 things? If it’s common knowledge to moms, to O.B.-G.Y.N.s, why is it not common knowledge to everyone else?”

So I started buying all that stuff and putting them in boxes, and that’s what I would give people at baby showers. And then they were like, “Oh, I wanna buy these for my friends – can I just get one?” So, I started selling them at cost to people, and they were like, “Just put it online, ’cause now my friend’s cousin wants to order one.” I put hearts on this paper; scanned it; sent it to this box printing company; got 50 postwell boxes. I sold about 20 over the course of a month – this was back in March [2019].

Then my friend’s aunt who works at The [Cincinnati] Enquirer heard about it, and I did an interview with her. One day, she called me, and she’s like, “It’s been a month now that I’ve been sitting on this. I’m just gonna hit send – like, right now. Are you ready?”

I was like, “I’m ready.” I mean, “Sure.” She published it, and I sold like five boxes that night. So now I’m down to 25 boxes left after my original 50. I was like, “This is amazing! Five – in one day!” I was over the moon, and I thought that was all that was going to happen from it.

I remember going to work the next day, and all these people were like, “Holy crap. Your interview is on the national news.” Like, what? U.S.A. Today owns The Enquirer, so they just pick up local news stories that are doing really well. Then I sold like 50 boxes in a day, within hours of that happening. Now I’m out, and then the next day, it was in POPSUGAR and then the next day it was on Yahoo! and then the next day it was in all these mom blogs…

It was so crazy because every story was a little bit different, but none of them had ever talked to me. By the end it was like, “Mom of five starts box with other moms” [laughing]. It’s like the telephone game; they were all just taking chunks from other stories. They were like, “Kerr says ‘that.’” I’m like, “I’ve never said that in my life.”It was wild; it was panic. I was like, “How do you stop it? This has to end.” Because I was out of these boxes. I did like a hundred in a week. I stopped the website and took it down for a day, and I remember me and my fiancé driving around to Walmarts and Meijers and Targets, and getting all of the plain white boxes they had. I bought this new printer, and I would just print on the paper “postwell” with the logo on it, and laminate it to a white box, and pack it. I was out of a bunch of stuff, so I would go and find similar stuff, and it was very hodgepodge. I would write a handwritten note in every single one that was like, “I’m so sorry. Please accept this box, and let me know if you need anything else and I will send it to you, but I don’t know what I’m doing, and I’m out of stuff, and I didn’t think this was ever gonna happen.” Every single one was worse than the last. Every single one was like, “What am I doing?” Circling the teardrops on the card – “the founder’s tears.” It was bad. I saved one for good laughs.

So, it’s been about four months since this all happened. What’s going through your mind right now, holding that hand-laminated box and looking at where you are today?

Oh, I think it’s hilarious. I was a wreck. I would come home; just lay on the carpet; just be like, “What did I do? What is happening?” I mean, I’m shipping these out of my little duplex apartment, and I would just lay there and be like, “I can’t send another one of these ugly boxes out with just my logo taped to it. This is ridiculous.”

My fiancé was like, “This is incredible! You’ve started something big.” He bought this map, and every time I would ship one out, he would pin another location and throw another mini-party, and I’m, like, on the floor.

I was just scared all the time, which is probably not in any story. I didn’t know if this was going to help people. I was just going off of what I’d asked moms at the hair salon. I wish there was a full year that I could do all this research and testing and design and everything, but it happened in like a week. I’m working now on going back and rebranding, coming out with a few more boxes, but it was crazy. It was not like this Cinderella… You hear these founders who were just ready for it, and I just remember my friend’s aunt from The Enquirer, Jennie Key, was like, “Okay, I’m gonna hit send; are you ready?”

I was like, “Yeah! Yeah, I’m ready. I got 20 boxes sitting at home, like, let’s do this!” It’s so funny now to remember that. I was so out of touch with how many people needed this.

So while all of this was happening, what did you hope would come out of it?

I hadn’t gotten any feedback on the boxes yet, which made me really nervous that I was sending out all of these boxes and I had no idea if they even helped. I work with entrepreneurs every day, and I never appreciated the courage it takes to put something out there. I was afraid to walk into Union Hall because all these people knew what I was doing and knew me as helping build these incredible startups. Like, this ugly brand and weird tagline and taped-together boxes – that’s what I was putting out there?

I think anyone has the ability to be an entrepreneur.

But then the first few moms who had gotten the boxes starting sending me notes, and that’s when it was like, “Okay. This is actually helping people.” That really helped me get over the fear. I would just take screenshots, and anytime I got really nervous, or anytime I would send a box out that I had to tape my logo onto, I would read them and be like, “They don’t care what the box looks like. They just care that it’s helping them” – which I think is kind of the whole point. It’s not a pretty process – giving birth or recovering afterward – and it doesn’t matter what the process looks like because it’s different for everyone.

I became obsessed with what the moms who got the boxes thought. I didn’t care what anyone else thought. And ever since then, every day I’ll get a note, and it’s like, “All right, why wouldn’t I spend my whole savings on this? It’s actually helping people.”

Can you read us one of the notes?

I got one the other day that was so nice. She posted it on Facebook in this moms group, and I don’t know her at all. It made me cry, and I never cry. She said:

@Postwell, your box SAVED ME. My mom got it for me, and I cried when I opened it. Our son was born with forceps, so you can imagine I had some serious healing to do. Thank you for creating such a carefully constructed box that addresses a huge need for women. Nobody told me how difficult postpartum recovery would be. I still have the handwritten note that you wrote in my box because it meant so much to be thought of in such a personal way. Ladies, you need this box for after you give birth and you need to give one to each of your friends at their baby showers. Business model well done.

Amazing. So, it’s really clear in your messaging that you’ve thought a lot about the ethics of how were you going to do business – even when it came together overnight. You don’t take money from the brands that are in your box; you buy from female- and mom-owned companies; etc. Tell us more about that.

I didn’t want this to become a subscription box where everything is given to that company for free just to get it into your hands. I wanted this to be the absolute best stuff – because at first I was giving it to my friends. I did all this research on the best stuff, and I think people really appreciated that. They trusted that what was in it was good.

I get offers now because it’s blown up so much that people are like, “I’ll just send you 100 hairties to put in the box.”

I’ll be like, “Thanks but no thanks.” I don’t do that at all.

Another big thing I think people are worried about is that when they order a box like this, their data is going to be sold. The data on brand new moms is really valuable to other companies who are targeting kids, so I’ve had people be like, “We want to partner with you to get your data and to market to these women,” because I do collect a lot of information about them to make the box as personal as possible. But I don’t do anything with it. It’s wiped every day. I only keep their address to send them a postcard at Christmas.

Knowing that every entrepreneur and their journey is unique, what do you think sets entrepreneurs apart?

I think anyone has the ability to be an entrepreneur. You have to have a lot of guts and a lot of courage to be able to tell people what you’re doing, and I think everyone has that ability – whether they realize it or not. I think you have to have a lot of tenacity and grit. Like, when I sold 100 boxes in a week, it’s like, “Okay, panic,” but then, “How do we do this?” Driving around all day just buying plain white boxes; you just have to make it work and put it in the hard work, and I love doing that. I mean, I’ll come home, work, and then at 10 o’clock at night be packing up postwell boxes for the next day.

How do you keep from going crazy?

I think if you love what you do, you’re not working. After I get done with my day job and I come home, and all I do is work on postwell, it’s like, fun. I don’t think of it as work. But I also run and do yoga – that’s mostly to be able to fit in my wedding dress, but it’s also very calming. I do hot yoga – the first time I ever went, I thought I was dying. I didn’t know it meant you were in a hot room. I thought it meant you built fire from within. [Laughs.]

Diving in a little deeper: How do you think we can get better, culturally, at not sweeping women’s health issues under the rug?

It’s weird because when I was doing all this research, I would study other cultures and how they approach it, and the U.S. is so taboo about it. In Mexico, it’s very common that when you go to the hospital, you only bring gifts for the woman. You don’t bring gifts for the baby; that’s weird there. In other countries, they have postpartum parties where right before you give birth, people bring you meals and compression socks and slippers, and that’s not a thing here. I think it’s just us catching on and not being so embarrassed to talk about it.

People have messaged me and told me that they bought a postwell box for their sister or their daughter or their wife because they were uncomfortable bringing up the conversation, but when they gave them this box, they could look at it together and talk about what all the stuff was. A mom actually wrote me a really nice note that she bought this for her daughter, who is about to give birth, and she had a really hard time articulating what her experience was. But with this box, she would just say, “Oh, I used this for the first two weeks, and then you’re gonna need more of these…” So maybe that’s just a start. I think the more we can just talk about it, the more women can have that experience, the better.

He said, “There are two types of entrepreneurs: Entrepreneurs who solve their own problems, and people who solve other people’s problems. They have the ability to sit and listen and empathize, and those are the entrepreneurs that do well.”

What else do you really want people to know?

I can really only say that this is just the beginning for postwell. By the end of the year, I’m going to come out with a lot more stuff. I have a few more boxes I want to come out with before I really invest a lot of time and energy in creating the community aspect. One of my good friends said, “You should do a partner pack that’s information and education and little pick-me-ups,” so I really want to do that soon. But the next box that’s going to come out is called the Motherload; it’s the Birth Box – which is the main stuff that you need for postpartum recovery – plus everything you need for breastfeeding minus the pump. I have some women who are about to give birth who are going to start testing those.

And then I want to come out with a box for during pregnancy; there’s a lot of stuff that you need right before you give birth, as well. And then I want to come out with the Birth Box but not with the same branding – so where this is like, fun, and you know shit’s about to go down, but it’s going to be incredible and you’re going to have this baby afterward… I want to come out with one that is very calming in its messaging that you could give your surrogate or the birth mom, if you’re adopting, or you could give someone who’s lost a child but is still recovering. It’s the same stuff, just not triggering to this motherhood journey. And then have a separate community for that.

What inspired you to add that?

My brother’s adopted; we adopted him when he was a baby. I always wondered, “What do you ever say or give someone to thank them for this gift that they gave you?”

And then a nurse friend of mine, her friend gave birth to a stillborn, and she was like, “What do you say or what do you do? Do you send them food or gift cards?” They didn’t take a baby home, so they don’t need the same stuff, but to physically recover, they do.

What else do you see for postwell’s future?

I think the next step is going to be developing some of my own products to put into it, and I’ve started that process a little bit. There’s a lot of things missing that people are putting together D.I.Y.s or hacks for – which a brand new mom has no time to do.

What are some of the best hacks you’ve seen?

A big one is pad-sicles. You get a normal pad, and then you squirt aloe vera gel and witch hazel on it, and then you roll it up and put it in the freezer. Those take a lot of time – that’s a big hack I’d want to figure out.

You’re incredibly empathetic. You yourself haven’t had these experiences, but you so easily put yourself into the shoes of others. Where do you think that quality came from?

I don’t know. I guess I’ve always been like that. My grandparents and parents are very similar. I was at this talk with Tim Schigel, who runs Refinery Ventures, and he said, “There are two types of entrepreneurs: Entrepreneurs who solve their own problems, and people who solve other people’s problems. They have the ability to sit and listen and empathize, and those are the entrepreneurs that do well.” I take that to heart. It’s a lot of sitting and listening, and not judging people, and just understanding what they went through to make sure no one has to have that pain or experience again. I think I always try to embody what Tim said and not just solve this for what I think I would want or how I would want it, but send it out and just listen.

Tell us about an influential woman in your life.

Oh, my gosh. Definitely my grandma. I talked about her in the TechOhio article because it talked about my whole childhood. I used to go around with my grandparents to these auctions, and they would sell stuff on eBay all the time. We’d wake up at 6 in the morning and go to this one flea market. She was just incredible. She was the risk-taker.

I remember they went to this wholesale auction and bought $10,000 worth of Disney Christmas ornaments in one day. They were like these local legends at this auction. My grandpa was like, “I just wanted to buy a box or two and test it,” and she was like, “These are gonna sell; I just know it.” Their balance is really inspiring to me. She has since passed away, but just that, if you’re going to risk it, go big.

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: Postwell’s Jess Kerr