49 Molly Sonsteng: entrepreneur, magic maker

Molly Sonsteng is a producer and experience designer who believes play is serious business. She co-founded Caveday, a community that helps people find deeper focus and a healthier relationship to work, and she runs Madcap Factory, a production house that builds games and experiences designed to bring more mischief into everyday life.

Before any of that, Molly trained as an opera singer at the University of Minnesota and later earned a master's in Educational Leadership from Columbia. She taught preschool, ran a political campaign office, developed curriculum at Carnegie Hall, and produced early morning dance parties around the world. 

She also co-founded Inconspicuous Games, running secret field games in landmarks and public spaces for companies looking to shake up how their teams connect.

These days she splits her time between Caveday and Madcap, building experiences that get people out of their heads and into the moment.
 

Find and follow Molly on her website, Substack & IG:

www.madcapfactory.com

mollysonsteng.substack.com

www.instagram.com/mollysonsteng

And of course, Caveday, the online coworking body-doubling space.

www.caveday.org

Kathie’s note: You know those people who are so grounded they exude a “you look calm and friendly too!” persona? Unpretentious, accepting, calm, cool & collected, all that. That’s Molly! She was one of the first faces I saw when I joined Caveday on January 1, 2021. I found it on CreativeMornings, one of their first FieldTrips. According to my calendar, it was July 8, 2020. “CreativeMornings, Brooklyn, get shit done in the cave: deep work.”

I took notes about the breakout sessions the first couple of years. As a guide one day, Molly’s breakout prompt was to describe your activities as a child vs. today. I said, “As a kid, it was music, books, and staying away from my brothers. Today I like music, books, and Zooming with my brothers.” (I mean, we change but we don’t, ya know?)

Writers Rotation intro/outro recorded at Dynamix Productions in Lexington, Kentucky.

Transcript

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Molly [00:00:01]:
I'm Molly Sonsteng. I'm an entrepreneur and magic maker. Writing is my way to solve thorny questions and practice the art of storytelling.

INTRO [00:00:09]:
Hi, welcome to the Writers Rotation podcast. I'm your host, Kathie Stamps. I love words and writing and people and talking. So I'm talking to people who write all kinds of things in different professions. It's a Writers Rotation. 

Kathie [00:00:26]:
Molly! How are you?

Molly [00:00:28]:
What a treat to see you and hear from you.

Kathie [00:00:31]:
Okay, I want to know everything about Caveday. What is the Caveday origin story?

Molly [00:00:39]:
I love that question. Jeremy Redleaf came to me and our third partner, Jake Kahana, in the fall of 2016 and said, you know, he had been struggling with all the projects he was working on, and he was talking to someone and he said, I just need a— I need a Caveday. I need to go into a cave and just not be distracted. I need to go into a place where no one can get at me. And he took this Caveday for himself and he said, I want to make one. I want to do one for other people. Do you guys want to do it with me? So he pulled me in as  an event person. He pulled Jake in as a design person.

Molly [00:01:15]:
And the three of us came together to put together an 8-hour day on a Sunday where we invited all of our friends into a coworking space in Tribeca in New York and took everybody's phones away from them, provided all the food and beverage you might want for a whole day, and led this essentially day of coworking where we had sprints, you know, 50-minute sprints followed by breaks. And we had a coach on site that would help you if you got stuck. We had rituals built in from the very beginning. It was a one-time event, and it was so beautiful that we did it again. And the second time we did it, there was someone from Fast Company who wrote about their experience, and that article ran, and suddenly we thought, uh-oh, we better button up a little bit and turn this into something real. And so that was the origin.

Kathie [00:02:07]:
That's amazing. And then that was in real life, and then you went (online).

Molly [00:02:11]:
Yes, in 2017 we had our first event on January 15th. And from there, we started running them monthly as these long 8-hour days on a weekend. And it was more mostly for side projects, things you could never get to during the week. And then people were starting to bring in their everyday work. And then we started running them in Los Angeles on the weekends. Then we started running half days more regularly than on the weekdays. Then, you know, it just started becoming this like, oh, people need this kind of support and structure every day and for their regular work.

Molly [00:02:44]:
This is not just for creative side projects. This is for our own day-to-day work where we need focus and structure and community. And then it just became daily and we were doing them in person. And before the pandemic, in 2018 we started running virtual and in-person events. So we started to build this global community early. So by 2020, when everything changed, we were very well set up to transition fully to being a remote business. Our membership grew exponentially because people were suddenly at home and didn't know how to structure their time. So we were like, look, here's an offer for you. Come join our community.

Molly [00:03:22]:
I don't know if you ever listened to the podcast How I Built This. Guy Raz always asks the question at the end, “How much of what you've built was based on luck or hard work?”

Molly [00:03:34]:
And I would say we, you know, there was a lot of hard work that we had put in place, and timing is everything. We were one of the few businesses that really saw beautiful growth during the pandemic and because of the pandemic. So both hard work and luck.

Kathie [00:03:50]:
I know I started looking in, it was 2016, I kept searching “coworking space.” They're like, yeah, we have one on Main Street; you can get your post office box, you can get your phone number. I'm like, no, no, no, virtual. Yeah, we're virtual. I was thinking about it before you even invented it.

Molly [00:04:08]:
I love that. And, you know, something that we talked about early on was, community was not one of our pillars. It wasn't something we were—we saw that that was happening. We saw that there was this amazing connection, people feeling like, thank you,  I'm so glad to be here specifically in person. But we were very intentional to be like, well, that's a byproduct of what we've created. And now, 10 years later, what we have is very much a community. But we didn't go out and say, we're going to build a community.

Molly [00:04:36]:
It happened because of—from my opinion, it happened because of the things that we put in place. And we weren't trying to push it. It happened because the structure was there. We had the container where community could be formed, but we weren't like, we are building a community.

Kathie [00:04:52]:
Very cool. And you were, all three of you were in New York?

Molly [00:04:56]:
Yes, we were all in New York. Jake is now  in New Jersey, just across the river. I'm in Minneapolis, and Jeremy is still in Brooklyn.

Kathie [00:05:04]:
I found Caveday on Creative Mornings and joined in January of '21.

Molly [00:05:09]:
I remember.

Kathie [00:05:10]:
A friend of mine was saying, This is the longest commitment you've had to anything in your entire life. And I said, probably so! What is your background? You said event planning? What else?

Molly [00:05:23]:
I wouldn't say my background is event planning. My training is in music performance, in opera.

Kathie [00:05:30]:
Stop it!

Molly [00:05:31]:
I love when I can surprise someone. Yes.

Kathie [00:05:34]:
Wait, singing? An instrument? Or both?

Molly [00:05:37]:
Opera singing, like classical singer.

Kathie [00:05:41]:
Were you a coloratura?

Molly [00:05:42]:
I wasn't a coloratura, which is like the very high, very light; just below that. I would do more of the—the roles I took were usually  the light comedic roles that were not coloratura because that's a very, very high range, but usually more the comic relief in the story versus the like big rich soprano.

Kathie [00:06:08]:
That's so cool. So you studied music in school?

Molly [00:06:12]:
Yeah, I studied music in school. I worked in music education for quite a while. I moved to New York and worked at Carnegie Hall and was developing school programs for their education department. And then I went over to the Manhattan School of Music, which is on par with Juilliard, same applicant pool but less of an endowment, but still a fantastic institution. I was the director of admissions for years at the Manhattan School of Music. And then one day I kind of had this aha, where I realized I couldn't distinguish one day from the next, or week or month. Everything was just sort of blurring together.

Molly [00:06:51]:
I knew that there was more I had more to offer. So I quit my job, didn't know what I was doing, said yes to a lot of different kinds of things, including making beautiful moments for people and experiences. And that kind of fell into production and event planning, but I wouldn't—I don't call myself an event planner. I design magical moments for people that I care about. That is one of my zones of genius.

Kathie [00:07:16]:
Now, is that Madcap Factory?

Molly [00:07:18]:
Correct. You did your homework.

Kathie [00:07:20]:
I read your Substack, darling.

Molly [00:07:22]:
Yeah, that's why we're here writing, right?

Kathie [00:07:24]:
Okay, tell me about Madcap Factory.

Molly [00:07:26]:
Do you know what the word madcap means?

Kathie [00:07:28]:
Does it mean fun? Madcap… zany, crazy, that kind of fun?

Molly [00:07:33]:
Yeah, it's a kind of an old-fashioned word that's fallen out of our lexicon, right? So Madcap by definition means amusingly eccentric.

Kathie [00:07:42]:
I love it.

Molly [00:07:43]:
So Madcap was basically just a container where I could hold all of the fun, whimsical, creative ideas I had and was throwing them out into the world. And some of them stuck, some of them didn't. So Madcap is really just an umbrella that houses a lot of my creative work. So what's in there are really some really fun things. In New York City, I ran a variety show for first-time performers once a month for people who had never, you know, they wanted to try stand-up but they didn't have a space to do that. Open mics can be very, um, there's a lot of pressure for open mics to try something new. And, you know, where do you get that feeling as an adult to have a little bit of risk but still be supported? So this was an evening where it was a beautiful sort of variety show where there'd be stand-up comedians, singers, jugglers, magicians, poets, all trying for the first time. And it was such a beautiful event for experimenting.

Molly [00:08:44]:
And the audience was always full, always supportive, because they knew that, like, people would bring their own friends. I'm going to read some poetry that I've written, will you come support me? So it was always a full, full audience in a proper venue in the Village in New York City. So that sort of fell under Madcap Factory.

Molly [00:09:01]:
Yeah, it was such a special thing. That is on pause for who knows, maybe it'll never come back. And then I have a product called Small S'mores. Do you know about Small S'mores?

Kathie [00:09:11]:
That sounds familiar.

Molly [00:09:12]:
Small S'mores is everything you need to make teeny tiny bite-sized s'mores in a beautiful canister, including, you know, it's got all the ingredients for bite-sized s'mores, but it also has a candle, roasting sticks, and matches, all in this like beautifully designed canister that can drop in the mail. So that was something that I had this idea for, iterated on, and then now  it's really just a corporate gifting thing that sells at the end of the year for the holidays. And another thing I run within Madcap Factory is something called Inconspicuous Games, which you may or may not have seen on Substack. Inconspicuous Games is where we play field games like capture the flag, when it's like a childhood camp game that you would play, in secret, in landmarks. So imagine being in New York City and playing a secret version of capture the flag inside Grand Central Station or at the Metropolitan Museum of Art, where you are with your colleagues or with your friends on a team of 30 split into two, 15, 15, playing this game in a public space where no one else knows you're playing.

Kathie [00:10:14]:
Or do they?

Molly [00:10:15]:
Or do—well, it's really interesting.  I just played Inconspicuous Games with a round of people here in Minneapolis, and no one had any idea. We told security that we were coming in, so we have permission to play there, but the public had no idea that there was a game being played right in front of them. It's so remarkable to see how that, like, the adrenaline it creates. Like, you're feeling like you're getting away with something. You're sneaking around in a public space even though you have permission to do it. So those are some of the things that fall within Madcap. But then there's like the things that I do in my personal life, like making magical moments for people, designing really specific, unique birthday experiences for the people that I love, that it's not just like, let's go get dinner for your 30th. Who's—I'm not hanging out with 30-year-olds.

Molly [00:11:06]:
Like designing really highly specific, highly unique, highly meaningful experiences. For the people in my life. Kathie, basically my purpose for being here, the big here, is to help people feel awake and seen and celebrated.

Kathie [00:11:22]:
And there's so much creativity to that. Did you have a vivid imagination when you were a child? Did you read a lot of books?

Molly [00:11:29]:
That's a great question. I'm not sure where it started. I do remember in the third grade planning my very first surprise party for my teacher. I enlisted the help of all the other students and their parents and the principal. And I knew it was her birthday. And so it was like the first time where I was—it's the very first time I remember doing something like pulling off a beautiful surprise.

Molly [00:11:53]:
My parents are amazing, but my father would always do grand things for us. And there were always like mini—I think he sort of inspired me. I sort of was around it. And then I took those ideas and just kept building on it. And it's a muscle, right? Start thinking this way. I just practice the muscle all the time. So there's always new ideas. And during the pandemic, there were times when I just felt flat, like so many of us did, or I was numb. But once I started to practice again, it just feels like it's muscle memory.

Kathie [00:12:21]:
That's very cool. And how do you keep track of everyone's birthdays and things like that? Are you a digital planner?

Molly [00:12:28]:
I do have a remarkable memory for dates. When I'm getting to know someone, I'll ask like, oh, what year did that happen? Do you remember what month? I get to know someone by learning their timeline and then sort of putting my timeline on top of it. So like, where was I when they were—okay, June of 2017, I was doing this in New York and they were in Kansas doing this. You know, I just, I layer my life on top of theirs and it helps me remember who they are. And then birthdays I tend to remember, but I also track them down. I put them in my digital calendar.

Kathie [00:12:59]:
Sure. Okay, writing. I'm assuming you've done a lot more writing before your Substack.

Molly [00:13:05]:
Why do you assume that?

Kathie [00:13:06]:
Because you're such a good writer. You can't just open up a Substack and go, okay, boom. I mean, you have to know what you're doing.

Molly [00:13:15]:
I love writing about things that I care about. I don't want to write on a subject that I don't know much about,  or that I'm not researched in, and I love storytelling about the things that I care about and the things that I've designed. It's like a—it feels so natural and good. I've done a little bit of writing here and there, and then I actually wrote a book proposal last year. It's sitting on a shelf. It's just there.

Kathie [00:13:41]:
Nonfiction?

Molly [00:13:43]:
Nonfiction. Yeah, it's a lot of what the topics of the Substack—it's a field guide on making magic of the everyday. That's kind of what the proposal of the book would be, should I ever decide to pitch it. So that practice was really good. I was writing every day, and I want to do more. I love, I love it so much. It feels good to write, and I think the stories that I'm sharing  are really positive and beautiful and like alive-making. So yeah, if, if there were more time, I would want to be writing more.

Molly [00:14:12]:
But it's so—it's such a compliment that you say that.

Kathie [00:14:14]:
Well, yes, because it's true. I think every art form, you know, they kind of all have the same root system. I don't know. I haven't really articulated that.

Molly [00:14:24]:
Interesting.

Kathie [00:14:25]:
Opera singing, music, writing, painting, dance, all of them, all of the art forms have some sort of root system. And your opera singing is nothing but stories. All of the arias, all of the opera. Opera is the plural of opus. Anyway, they're all telling stories.

Molly [00:14:46]:
Yeah, and the practice itself requires practice. All art forms, if you're wanting, you know, diligence—if you're wanting to keep at it and have any level of skill, it requires diligence.

Kathie [00:15:01]:
Yes. What is the name of your Substack?

Molly [00:15:03]:
Madcap Field Notes.

Kathie [00:15:05]:
Madcap Field Notes. And when did you start it?

Molly [00:15:08]:
A year ago. 

Kathie [00:15:10]:
What's your cadence? Once a week? Once a month? Once a whenever?

Molly [00:15:13]:
I had the intention of writing every other week, and that felt stressful for me. So now it's—right now there's no cadence. It's just a, I've got a story to share, which I know is not the recommendation. At this point, would I love to have a big audience? Of course. I don't. Not yet. But repetition, repetition, you know, if I want to be serious about it, I have to be diligent about a cadence, right?

Kathie [00:15:40]:
It's what they say. It's just what they say. I had a newsletter. I did one once a month and then something happened and then I haven't done it at all. I do this podcast. It was twice a month, the first and second, you know, whatever it was, second and fourth. And then I was co-writing a book for the university and missed a month or so. And then just, you know, life happens.

Molly [00:16:05]:
Exactly. At this point, I think that there's—to be bogged down by a cadence and think like, if I don't do this, I can't do it at all. No. If you really—

Kathie [00:16:13]:
That's all-or-nothing thinking.

Molly [00:16:14]:
Exactly, exactly. No, thank you. I'm not here for that.

Kathie [00:16:17]:
That does not serve.

Molly [00:16:18]:
No.

Kathie [00:16:19]:
What are you reading?

Molly [00:16:20]:
Oh, currently I've been reading it for a bit because time and not prioritizing. But I'm reading the novel Rebecca.

Kathie [00:16:28]:
The old one? The real one?

Molly [00:16:30]:
Yes. I can't remember the—I can't remember her, uh, what is her name?

Kathie [00:16:35]:
Daphne… du Maurier?

Molly [00:16:36]:
Yes, Daphne.

Kathie [00:16:38]:
I just pulled that out of my head.

Molly [00:16:39]:
I know, we should know this. It doesn't matter. I mean, it does matter, but for the purpose of our conversation, for the people that we are, Kathie, we should know the answer to this.

Kathie [00:16:48]:
Rebecca, 1938!

Molly [00:16:50]:
Yes, that's right. It's sensational. It's sensational. I read Frankenstein, the original Frankenstein, before this, and I'm sort of in this Gothic—

Kathie [00:16:59]:
Can you believe that a teenage girl wrote that? Or however old she was. Mary Shelley.

Molly [00:17:03]:
I know. And then to read this book written by, you know, another Gothic novel written by a woman. I have a theme right now. And these classic novels, they're so—oh, they're beautiful. And this story is amazing. I think Hitchcock turned it into a film. Didn't know that. I'll have to watch it after this. Yeah, I tend to just read fiction. Of course I read things on the internet, but when it comes to really reading, I tend to stick to fiction.

Kathie [00:17:28]:
Do you read the book-book, the ebook?

Molly [00:17:31]:
Yeah, I read the hard copy. I have to.

Kathie [00:17:34]:
I'm an audiobook person.

Molly [00:17:35]:
It doesn't matter however we do it. It doesn't matter.

Kathie [00:17:38]:
Exactly.

Molly [00:17:38]:
Whatever works for you.

Kathie [00:17:40]:
Molly, thank you so much. This has been so much fun.

Molly [00:17:42]:
I love this, and I'm grateful to be invited.

Kathie [00:17:46]:
See ya.

Molly [00:17:46]:
Bye, Kathie. Thank you.

OUTRO [00:17:48]:
Thanks for listening to this episode of Writers Rotation. Like and subscribe for more, and remember, writing is a marketable skill. Smiling is a remarkable skill.