The Story

Jason from Bento started a business that prepared and delivered pan-Asian meals on-demand. Lauren and Emma from Dating Ring wanted to reinvent online dating. Mary from Saint Harridan made sharp suits for masculine women and trans men. And Mike moved food across international borders, evading employees of a large grocery store chain. This episode, we return to some of the companies we followed in previous seasons and find out how their founders are doing—and what the label “entrepreneur” means to them now.

The Facts

David Herman and Mark Wilkening mixed the episode.
Mark Phillips wrote and performed our theme song.
Build Buildings wrote and performed our special ad music.
Additional music by Jpoetic, Get Better, Hot Moms Dot Gov, and the iconic Bobby Lord.

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Show transcript

LISA: From Gimlet, I’m Lisa Chow. This is Startup, the show about what it’s really like to start a business. We’ve reported on a lot companies and founders in the nearly three years since this show launched. We’ve updated you on our own company, Gimlet Media, but we’ve never reported back on any of the others we’ve followed. So on this episode, that’s what we’re doing. Returning to some of the founders who let us in as they raised money, built their companies, and shifted business models. A lot has changed for all of the people we’ll hear from in this episode. When we met them, they’d embraced being entrepreneurs. It was the identity that fit them best. But now years or months later… we’re checking back in to see — does that label still fit? And just a quick warning, there is some swearing in this episode.

LISA: One of the companies we followed in Season 3 … the season about endings and almost endings … was Bento. An on-demand food delivery company founded by two guys named Jason Demant and Vincent Cardillo. Molly Messick reported that story, and she has this update.

MOLLY: When our episode ended it was just over a year ago, and Bento’s founder, Jason, had just left me this message.

JASON DEMANT: It’s, uh, Wednesday, 3:15. As of 2:39 PM, our round is closed. Got the last 10K, pushed us over 100K. Yay!

MOLLY: A hundred thousand dollars was the amount of money Jason thought he needed to get the company to profitability. At the time he told me that it was the last raise he planned to do. By then Jason had been through a lot with Bento.He pitched the company as the restaurant of the future. A restaurant you’d never have to visit because its food would come to you. Delivery would be extremely fast, because as soon as you placed your order in the Bento app, the app would ping a driver nearby. Drivers would have ready-made dishes there in the car, prepared in Bento’s kitchen. And they would put together your order, grabbing the food from special bags designed to keep it hot or cold. Jason envisioned that someday Bento could be as ubiquitous as Chipotle, without the expensive storefronts. But it would be more than a restaurant. It would be a scalable tech company. At the time Jason and his partner Vincent started Bento, that vision seemed very possible. Venture capitalists were pouring tens of millions of dollars into on-demand food startups like theirs. Companies like Spoonrocket, Sprig and Munchery. Jason and Vincent were able to raise 1.5 million. But within a couple of months of launching, they struggled. They ran into problems managing their kitchen and controlling delivery costs. At one point they were losing $20 on every bento box they sold. After one especially rough day, Jason recorded this conversation with his wife, Sharon.

JASON: Next week is going to be awful. Like really, really awful… And so I think we may shut off tomorrow.

SHARON DEMANT: You mean like close Bento?

JASON: Not close Bento. By the way I’m recording this.

SHARON: Okay… Can you please explain more what you’re talking about, because it sounds like you’re closing down Bento.

JASON: We’re not closing it down. We’re basically, like, becoming a catering business.

SHARON: Oh.

MOLLY: Bento pivoted. By the time its transformation was complete, the company was selling its meals through third-party catering startups instead of delivering them directly to customers, and Jason’s co-founder Vincent had found a job outside the company. Jason had cut his own salary, and he was dipping into personal savings to cover basic expenses … which was kind of stressful because Sharon is a stay-at-home mom and they have two young kids. Jason needed more money to keep Bento’s doors open. And when we left him last May — he’d pulled off that 100 thousand dollar raise. He was optimistic. But turning Bento into something sustainable seemed like a long shot, and I felt nervous for him. After the episode aired, I stayed in touch with how Bento was doing through a monthly email that Jason would send out. It was meant for investors, but he’d added me to the list. And for a while it seemed like things were going the way Jason hoped. Catering orders picked up, and the company got closer and closer to profitability. But then came the September email —

JASON: So where do you want me to — you want me to just start at the top?

MOLLY: Yeah — yeah, if you wouldn’t mind just starting at the top.When I called Jason back recently, I asked him to read it to me.

JASON: Ah unfortunately this is not a positive monthly update. In the span of four days we lost 40 percent of our recurring revenue.We recovered half of the lost revenue, but that’s not enough. We have not fully paid September rent…

MOLLY: It lays out what happened in painful detail. In late August, Bento hit its magic break-even number — more than 20 thousand dollars in revenue in one week. But then came a fateful order from a big catering partner. It was an order for sushi burritos, and the partner sent them back.

JASON: They rejected our delivery because the burritos weren’t at the proper temperature. They had every right to reject. Our contract specified the delivery temperature and the burritos were not there. On top of that, two other catering startups that had been getting food from Bento slashed their orders. Jason started looking for opportunities to merge or get acquired by another company. But one by one, potential partners dried up, and by December Jason faced a choice. Keep going on his own, or close Bento.

JASON: I looked at all of the options that I was thinking about and I was basically out of them. And so that was the point I decided to shut it down and told my employees you know two days later and shut down a week after that, and that was pretty much it.

MOLLY: Were you taking a salary at the time Bento closed?

JASON: Yeah, 40 thousand dollars so not a sustainable salary. But you know, had I been more optimistic about the future I think we could have continued but I just didn’t know where that growth was going to come from anymore.

MOLLY: Right. You don’t have to answer this question, but I’m going to ask it.

JASON: Okay…

MOLLY: How much of your savings did you ultimately use to keep running Bento?

JASON: I’m not even sure I know the answer to that. I think ignorance is bliss when it comes to that. Uh, a good portion. It never got so low where I felt like I was putting our family in jeopardy. But obviously, you know the history of us having the conversation of “I think this is the last one” and then me continuing to take money out. So it went much lower than I thought I would go. But never to the point — where I felt like I was taking a humongous risk.

MOLLY: When Jason says “us having the conversation”, he’s talking about conversations with Sharon, his wife. They were at home at their apartment in Oakland when I called, and they’d just put their two young daughters to bed.

MOLLY: I’d actually love to chat with Sharon if she’s there and handy. Is she available?

JASON: Yeah, she’s here.

SHARON: I’ve been cleaning the house the whole time and listening.

MOLLY: Hi Sharon, how are you?

SHARON: Hi! Good, how are you?

MOLLY: I wanted to hear what Bento closing meant for Sharon. Because she’s been in this with Jason, experiencing the ups and downs along with him. And she talked to me about how isolated she felt while he was working long hours at the company.

MOLLY: Do you remember when he told you he was going to close the company?

SHARON: I remember him telling me a few times just because I feel like I’d heard it so much I didn’t believe him. So it’s like when he actually did decide to close it I kind of just said, “uh huh, okay.” And then when, you know, when he gave me like a date. I think that was when I really started to believe him.

MOLLY: And what did you what did you feel in that moment?

SHARON: Um you know obviously it was bittersweet but it was more sweet for me. Um. The emotional aspect was I don’t want to see my husband’s company shut down. You know the one that he worked so hard on and took so much out of our family and… It was kind of you know it doesn’t feel like a waste of time but it kind of just feels like I don’t know how I would put it. I don’t know if there is a phrase for that that’s not as negative as a waste of time.

MOLLY: The whole time Jason was working on Bento, Sharon had her sights set on a house. Someplace with a garage and a yard where the kids could play. Using up their savings so that Jason could keep running Bento really stressed her out.

SHARON: As a person who is obviously an important part of his life but not in the business, I felt kind of stuck. Because on one hand I wanted to be 100 percent supportive because that’s just how our relationship is. But on the other hand, you know, we’re losing this money that we’ve been saving and just knowing that it was being taken out with every time every time we went grocery shopping and every time we went to Target… I don’t know, it just kind of felt unfair that I wasn’t the reason why it was coming out. But then I was also supportive and I never told him to stop. So it was also you know I was also not making anything — doing anything to make a change.

MOLLY: After Bento closed Jason scrambled to find a new job. He landed one pretty quickly, working in sales at a small startup that uses consumer data and machine learning to customize websites.Sharon says the change has helped her feel less stuck and stressed. Money is still tight, but Jason comes home earlier than he used to, and that means she gets out of their apartment more often. Sees friends, goes to the gym. But Jason still hasn’t left Bento behind, at least not completely. He’s still in the process of winding things down … and sorting through what he’s learned.

MOLLY: Some of what you said made me think that. Had you known how things would go, you might have made the decision earlier to stop.

JASON: Oh yeah.

MOLLY: Yeah?
JASON: I mean you want to go even more what-if scenario. Like sometimes people ask “Would you do this business again or do you regret it.” I don’t know what the best way to phrase the question. The — I would… I am grateful for everything I learned and experienced through Bento. But if I could do it all over again I would not start Bento. I would much rather gain that experience and learn those things with a different business.

MOLLY: Wow that’s a big statement.

JASON: The the thing, the truth is I have zero percent chance of success with the business that I started. There was no possible chance I could have made that work. I truly believe that now. Now, had I started with the catering business, I could have made that work but that wasn’t a business I was interested in running. I would have never started with a catering business.

MOLLY: And you’re saying like you just learned through experience that there was no way to make the economics work if you were selling directly to customers. The model was just not going to work.

JASON: No never. It literally never had a chance.

MOLLY: Jason believes that not only because of his own experience, but because of what happened at other startups that tried to figure out on-demand food delivery. A company called Maple that had the backing of celebrity chef David Chang and raised a reported 50 million dollars in venture funding struggled with some of the same problems Bento did. Keeping costs down, and keeping meals affordable. It closed last month. So did Sprig, which raised 57 million dollars. Jason says one big takeaway of Bento for him is that he’s not good at setting rules for himself. He’s not good at saying “Okay, if we haven’t gotten the company to this level of revenue by this date, we’re done.” If he starts another company, he’ll want to do a better job of that. But on the other hand, he’s also glad he stuck with Bento and tried as hard as he did to make it work.

JASON: Jason Calacanis, my my biggest investor and probably one of the most important people that was involved with Bento in terms of the investor side you know he greatly admired my persistence. He literally we were having lunch and this was a quote from him. I shared it with Sharon of course. And he said of the people that he’s invested with and failed I tried the hardest.

MOLLY: (laughter): There’s honor in that, yeah…

JASON: I’m the king of the losers. But you know it’s — yeah I mean it was it was still it was still a compliment, right?

MOLLY: For now Jason is focusing on stability… building up some savings. He says he thinks about starting another company, but it will be a while before that happens.

LISA: Molly Messick is senior producer of StartUp. Coming up:

LAUREN KAY: There is going to be a billion dollar company that provides on-demand dates. And Dating Ring is going to be that company.

LISA: That’s Lauren Kay from Dating Ring. The company we followed for all of Season 2. Where she and her cofounder Emma Tessler are now… that’s after the break.

*BREAK*

LISA: Welcome back to Startup. Dating Ring, the company we followed in Season 2, had a bold plan to reinvent online dating. It wanted to take an ancient practice — matchmaking, and scale it. Which meant we sat in a lot of meetings like this:

EMMA TESSLER: So, alright I’m looking at your profile here. How’s it been going? John: I’ve only been out with one person. Okay, and — which one? Melissa.

LISA: This is Emma Tessler, cofounder and Dating Ring’s chief matchmaker, in a meeting with a client named John. She took notes as he told her about himself. He liked to run in Central Park. He had a rescue cat. He was looking for a woman who wanted kids. But at some point during the conversation, he said he’d been feeling discouraged by the whole dating process.

JOHN: Yeah, I mean I feel like I’m a little undateable.

EMMA: You are not undateable! Oh, I promise you, you’re not.

JOHN: I don’t know, I think when I go on a date I emit or give off a certain vibe that repels girls away from me.

LISA: After John left the room, I sat with Emma, to get her professional assessment.

EMMA: So I wrote, um, sponsors cats and dogs at the ASPCA. Is way sweeter than he looks, likes tall girls, athletic, smart, devoted, committed, wants a friend, he has a strong Staten Island accent, leaves his shirt unbuttoned really far, he wears a lot of hair gel. Them’s my notes.

LISA: What did you think about the — so you don’t think he’s undatable?

EMMA: No! Definitely not. To be fair, you would be hard pressed to find someone that I did think was undatable. I really do think there’s a lid for every pot.

LISA: Beyond listening in on meetings like this, we followed Dating Ring as they tried to raise money, as conflicts flared between the company’s cofounders, and as growth stalled. About a year into the company, Lauren, the CEO, was burnt out. She’d been getting rejected by investors, again and again, and this triggered a period of depression for her.

LISA: I just tumbled and tumbled and tumbled until I hit rock bottom. And I was just sitting at my computer, my fingers resting on my keyboard. And it was one of the first times I was working with employees who started working for Dating Ring. I was watching them work and I was thinking “Wow, i’m a useless person. I’m supposed to be the CEO. They haven’t worked around me before and I’m just staring, like, doing nothing.” Then almost a year later, Dating Ring came very close to running out of money. The company’s matchmakers were nervous about what would happen next. I talked to one of them, Shearly Markowicz.

SHEARLY MARKOWICZ: I never started looking for a job, I mean I’m going to tell you, everyone told me to look for a job, everyone was like, you are nuts cause I’d be like, they’d be like, how’s your company doing, and i’d be like ew, terrible. My company is doing real bad. You know, like, no new members coming in. It seems like we’re really like, getting down there.

LISA: By early 2015, Lauren and Emma had decided to quit fundraising, and turn Dating Ring into, what is known in Silicon Valley as a lifestyle company … a company that isn’t trying to grow rapidly, but is more focused on becoming profitable. That’s where we left them. And to be honest, when I stopped reporting on Dating Ring, I sort of expected they’d limp along for another couple months before shutting down. But that’s not what happened…A couple weeks ago… I made a visit to Dating Ring’s office in downtown Manhattan.

SHEARLY: Oh my god it’s so good to see you, come on in.

LISA: The company is still operating out of the same coworking space it did two years ago. But its founders — Lauren and Emma are gone. Shearly, the matchmaker though, she’s still there.

SHEARLY: My name is Shearly, and I’m the CEO of Dating Ring, currently, which is very exciting.

LISA: Shearly is now running Dating Ring, and the company has stopped hemorrhaging cash. It’s profitable, with nearly 30-thousand free and paying members in New York, San Francisco, Los Angeles, Boston and Washington DC. And the way Shearly’s made Dating Ring profitable is by cutting costs. She’s now the only full-time employee but gets by with the help of seven part-time matchmakers. She draws a salary but doesn’t have much equity in Dating Ring. Lauren still owns the biggest stake … but that doesn’t stop Shearly from pouring all of her energy into the company.

SHEARLY: It does feel like a baby to me and I care about it a lot and I feel invested in it and it’s definitely a weird feeling to feel invested in something that is mine but not mine. And that the people that we were in it together. Are not that they don’t have the same feelings about this baby anymore.

And I get this. For me, it was hard to imagine Dating Ring continuing to exist without Lauren or Emma. I wondered how they felt about it — about this thing — their baby — continuing on without them…

LISA: so how have you been?

LAUREN: Uh, Yeah. No I’ve been doing really well.

LISA: I called up Lauren, Dating Ring’s former CEO.

LAUREN: I left Dating Ring not too long after we finished recording and just entered a completely different phase of my life. Much calmer, ah much happier, and definitely not as exciting.

LISA: Lauren told me she left Dating Ring because running a small company that’s not pushing for growth just wasn’t something she was particularly interested in doing. And she knew that — because she’d already run one small business. Her first company, a childcare service called Smart Sitting, which she started in college. But Lauren said that even though she wanted to leave Dating Ring — not running a business felt really strange to her at first.

LAUREN: You know I started my first company halfway through college and then my second company while I was still working on my first. I was very I was always very busy, very type-A working on a million things. And all of a sudden I had a lot of free time and it was it was weird. And I was happy but I felt I felt really confused about who I was and what I was doing and you know my friends and family very much saw me as an entrepreneur and everyone would always say oh what are you going to do next.

LISA: This period of confusion lasted a year. Lauren considered applying for law school, business school. And she interviewed for a handful of full-time jobs, but her heart wasn’t really in it. She kept her spirits up by running and cooking. She was also tutoring students in math and test prep, something she’d always done, and she was making good money doing it.

LAUREN: And I was meeting with Emma, telling her that I was still unsure you know what would I want to do next. And she was like Lauren you’re you’re tutoring you’re you’re doing well financially you’re really happy. Why can’t you just do that? And I think it was really my conversation with her that sort of sealed the deal that that made me stop looking for anything else because I realized I was happy. Other than feeling like other people thought that I should be doing more.

LISA : And what do you think. I guess, was there something about the life of being an entrepreneur. You know when you did your first company and then dating ring. Was there something about it that you just didn’t want to return to.

LAUREN: Yes. So I was a very stressed and anxious person and I still am. But it came out a lot more throughout my life as an entrepreneur. And that’s not to say that I think it’s a bad job. I just think it really depends on your personality type and your anxiety levels how sensitive you are. And I just realized like there are definitely parts of my personality that I think made me great at running start ups and there are parts of my personality that that made me bad at it. And the most important thing is there were parts of my personality that just made me unhappy doing it.

LISA: And did it take leaving Dating Ring and having a moment where you didn’t have anything on your calendar to realize that? Or do you think you were realizing that even while you were working at Dating Ring?

LAUREN: I mean I knew that from from before Dating Ring I just I think I just sort of accepted it as this is how life is. I’d always been on track of like try to externally succeed as much as possible. And you just deal with the stress and anxiety and hours. But after leaving I realized no that’s that’s not the case. I don’t have to continually put myself into positions where I’m working 100 hour weeks and complaining about that and being anxious and being a bad girlfriend and being a bad daughter. And that’s been a huge other change. I mean I see my family almost every week now. I’ve formed relationships with my brothers as an adult with my parents. And before that it was just you know phone calls when I had time saying I was stressed and getting back to work.

LISA: But despite all of this, Lauren doesn’t regret her years spent trying to build the Uber of dating.

LAUREN: I think regardless of what I do with the rest of my life I’m I’m really happy that I had those experiences. I think I learned a lot in a very short amount of time. Um, I think sometimes people stay in their career for decades before realizing they’re unhappy and changing like I had my midlife crisis at 26. So I was able to fast forward a bit and focus on what’s important and spend more time with my family and you know get healthy. And, you know, save myself a decade or two there.

LISA: Lauren’s co-founder Emma, on the other hand, had never identified as an entrepreneur before Dating Ring. But she had dreamed of being a matchmaker — and so when she got connected to Lauren — who had just started the company — it seemed kind of meant to be.

EMMA: I loved being a matchmaker. I think what we did and what Shearly is still doing was so cool. And so I miss that for sure.

LISA: But Emma says after Lauren left Dating Ring…she realized she had some unfinished business to do. Emma had dropped out of college when she was 20 … She’d been depressed. When she was a sophomore, her sister had died of leukemia. Emma told me she also wasn’t very good at school…she hated being constantly evaluated. She’d skip class, not do her homework. But running Dating Ring had given her a new confidence and she felt like now was the time to go back. At first she says — she thought she could do both.

EMMA: I decided, “oh I’m gonna start school and I’m going to do Dating Ring part-time and school full time.” Because I’m like some kind of moron. And I couldn’t do it. Unsurprisingly… I mean everyone was like there is no way you can do it. And I was like fuck you, I can do anything. But no they were right and I couldn’t.

LISA: Emma officially left Dating Ring about a year after Lauren did, and is on track to graduate in January. She plans to get her masters, so she can practice therapy in New York.

LISA: When you left, tell me how you felt about not being involved in Dating Ring kind of day to day.

EMMA: I felt and still feel, it’s the same feeling, hugely hugely guilty. It feels super weird to birth a company and put every ounce of your energy into it and do that for four years and then have nothing to do with it. You know it’s like sending a four year old off to boarding school and you’re like OK bye bye! Like, send me some emails. Like you don’t do that. It’s a 4 year old…That was a lot of my identity was running that company and not having that is a huge loss.

LISA: But Emma says … there are a lot of things about startup life that she doesn’t miss.

EMMA: that sort of constant level of not knowing what’s in front of me and having my future be uncertain that not knowing is this company going to survive if it is going to survive. What is it going to look like is it going to be recognizable to me.

EMMA: you know I’m a student. Nothing is more planned than studenting. Right. I know when every final is going to be I don’t want every homework assignment is due and going from such a deep uncertainty to having everything planned for you is is a really big change in my stress level and you know how well I’m able to sleep and things like that that I just I didn’t take into account.

LISA: So you have no interest in running your own business?

EMMA: No no. did it sound like maybe I was gonna throw up like I had a small stroke you know. I mean that’s obviously not entirely true. Right. I want to go into therapy there is a certain level of autonomy in that where you. You have your own practice you make your own schedule or what Lauren’s doing right she has her own tutoring thing like both of us have have sort of held onto that idea of autonomy which I think is very appealing to us. And both of us like being our own boss but you know the idea of running a business makes me want to jump off a bridge.

LISA: I asked Emma and Lauren about their relationship to each other post Dating Ring. They both said they see each other….but much less frequently. Here’s Emma.

EMMA: It a little it feels like someone who you went to war with. You know she and I will be connected in a way that I have never been connected to anyone you know and we went through something and we built something together and we were married. But I think that both of us sort of reacted in like a traumatic way we’re like, oh, we do want some distance from that life.

LISA: Our next founder is struggling to find that distance. We met Mary Going in Season 3. By the time she’d started her custom suit business, Saint Harridan, she was already a serial entrepreneur. She’d started a website design firm just as the internet was taking off, and ran a successful hot sauce company for five years before selling it. Then she moved on to an idea that was particularly close to her heart… making clothes for masculine women and trans men. Producer Luke Malone has this update.

LUKE: Mary’s never been comfortable wearing women’s clothes. Back when she was a kid growing up in South Carolina, she would cry every time her mom tried to put her in a dress. She preferred pants, and a little sheriff’s outfit if at all possible. She has this particularly vivid memory of the time her mum made her wear a dress on her first day of school.

MARY: I screamed and cried and by the time we got to the school and I was dressed in this gross, yellow, frilly dress, I was screaming, hanging on to the edge of the doorway begging her not to make me wear that to school. Not to make me go into that classroom and let people see me in that dress.

LUKE: Mary’s pretty butch. As an adult, she started shopping in the men’s department. But she quickly discovered that men’s clothes don’t always fit her properly… shirts, for example, are tight across the chest or loose around the biceps. When it came to buying a suit for her wedding, she knew a men’s suit wouldn’t work…She tried on a bunch… but men’s suits are cut for men’s bodies, and the dimensions weren’t right. So she spent $1,800 getting a bespoke suit made. And it was a game-changer.

MARY: You know, the day of our wedding when I got to get married, I wasn’t distracted by hating my clothes, or feeling like I looked weird or bad or short or swallowed whole, which is what I usually felt like I looked like. I got to be me… And I also thought, I have to do this for other people, like I have to do this for other people. I can’t keep this to myself, it’s too good. And, so I wanted to start a company that allowed this to happen for people.And so she did. She started making custom-fit suits that were affordable…. closer to $800 than the $1,800 she spent having her own wedding suit specially made. She opened up a store in downtown Oakland and an online shop where her customers could buy shirts and jackets. She made it so that butch women and trans guys could go online and click a button just like anyone else. But Mary struggled financially. She had customers, but making suits is expensive, and there never seemed to be enough money. Last year, Mary cut her own salary… sometimes taking nothing, sometimes paying herself just enough to cover the rent. She and her wife… maxed out their credit cards. But the company kept taking on water, and Mary’s faith in herself was shaken.

MARY: At this point, we are into our 4th year, we’ve done three whole years we’re into number four, I feel like we’ve plateaued and I am the one who is standing there.

LUKE: When Mary was on the show last May, she didn’t know what was going to happen. After our story aired, she was focused on raising more money. But then, an investor … who had promised Saint Harridan fifty thousand dollars … pulled out. Mary called in favors to cover the loss. But as she sat at her kitchen table one night, looking over the company’s books, it hit her. The risk was just too high. Her investors—who now included her friends, family, and customers—stood a good chance of losing their money. And it wasn’t just that.

MARY: In order not to lose their money, in order not to make the whole thing fail I was going to have to work my ass off from morning to night. I was really going to have to do things that I’m sad to admit this. But I feel like I didn’t have the energy to do it. I was too tired. You know it’s like our business had been running on my adrenaline for five years and I was spent. After all of that hard work, all that adrenaline: she made a decision. It was over. She was going to close Saint Harridan. It felt like shit. It felt awful. I mean you know we can talk about crying like a little bit of tears you know I couldn’t breathe crying. It’s kind of like I have failed I have failed crying… sadness. You know?

LUKE: She told her customers, put a note up on the website, and filed for bankruptcy—both business and personal. Mary took it hard. She got depressed, and she started to gain weight. Which felt like another slap in the face. Because it meant the one part of her business she had left — the clothes she had made — no longer fit. Her Saint Harridan pants are too tight to wear right now… and she can’t afford to go to a tailor and get new ones. She’s back to feeling like she did when she started the business… frustrated that she can’t just go out and buy something off the rack that fits right. It’s a feeling she knows her customers can relate to…

LUKE: I mean because obviously that’s not a situation unique to you. There’s a lot of you know women and trans guys who feel the same way. So what do you think this loss the loss of St. Harridan has been like for them.

MARY: Some people have written to me and talked about what a big loss it is what a… You know that they’re so proud when they wear their shirts or their pants or their suit. Um, a person wrote me to say she’s so scared she’s going to spill something. It’s a loss. It really is a loss.

LUKE: Mary closed Saint Harridan five months ago. She landed a temporary job teaching a business class at a small college… and she’s spending more time with her wife and kids; she tells me she’s putting some space between the minutes. She’s also been looking for full-time work… but it’s been a bit of a struggle. Not the finding work part… but what having a full-time job would mean for her. Mary hasn’t worked for someone else in almost a decade and she finds it hard… Because her mind is somewhere else.

MARY: Everything I think, everything I read, all of it gives me ideas for businesses to start. And makes me want to start another business. That’s the hard part. That’s the hard part. Having to become somebody that doesn’t really feel in alignment with who I am. Because I have to be practical and make money for retirement.

LUKE: When Mary closed Saint Harridan she lost more than just a business. She had to turn her back on something that feels like a key part of her identity… running her own company, and being an entrepreneur.

LISA: Luke Malone is a producer of Startup. And before we go, we have some news about someone else who’s been on the show. Mike Hallatt from Pirate Joe’s. He made a business of driving Trader Joe’s groceries across the border into Canada and reselling them at higher prices out of a rented storefront in Vancouver. He’d been fighting off a lawsuit from Trader Joe’s for years… And last week … struggling to raise money to cover his legal costs … Mike agreed to close his store. When we caught up with him a couple of days ago, he told us that customers were still stopping by, hoping to snag one last container of sea salt chocolate almonds. But Mike himself… is over it. Sort of.

MIKE: I’ve had so much Trader Joe’s stuff over the years that you know there’s…part of me is like if I never have another Trader Joe’s product that’ll be fine. But you know I see the veggie burrito and I’m like “Oh, I could probably have another.” That’s a pretty damn good burrito. Oh and there’s the chile rellenos…yea I should mic up a chile relleno. God those are good…

LISA: But the days of incognito trips to buy thousands of dollars worth of gluten-free pancake mix and triple ginger snaps… they’re over. Next time on Startup… when you pitch an idea, confidence is key. And Mason Gordon definitely has confidence.

MASON: I kind of jumped up on his couch and I said, “The whole league is gonna be full of guys that dunk like LeBron James and Dwayne Wade. It’s gonna be INSANE!” And he was like get out of my office, you’re a maniac, and never talk to me again.

LISA: What it takes to create a brand new sport. That’s next week.

LISA: StartUp is hosted by me, Lisa Chow. Our show is produced by Bruce Wallace, Luke Malone, Simone Polanen, Emanuele Berry and Amy Standen. Our senior producer is Molly Messick. We are edited by Caitlin Kenney and Pat Walters. Production assistance and fact checking by Alvin Melathe.

Mark Phillips wrote and performed our theme song. Build Buildings wrote and performed our special ad music.

Additional music by J-poetic, Get Better, Hot Moms Dot Gov, and the iconic Bobby Lord.

David Herman and Mark Wilkening mixed the episode.

To subscribe to StartUp, go to Apple Podcasts, or whichever app you like to use. Or check out the Gimlet Media website: GimletMedia.com. You can follow us on Twitter @podcaststartup.

Thanks for listening. We’ll see you next week.

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