Entrepreneurs 101 – Haely White and Samantha Gutstadt, Don’t Call Me Mommy

Motherhood is a dramatic change in life, and Haely White and Samantha Gutstadt are dedicated to bringing in the comedic elements. After hosting a red carpet event together, Haely and Samantha came up with the idea “Shit No One Told You,” which was pitched and greenlit the very next day. Since then, the pair has worked together on various acting, advertising, and comedy projects, and they have proved to be the perfect team. Listen in as they discuss the start of their team, their growth through 2020’s production challenges, and a robbery that they helped to solve.

Samantha Gutstadt [00:00:03] There’s like a robbery going on behind us, but we don’t know. But there is and we have three cameras capturing the whole robbery from beginning to end.

Sam Jayanti [00:00:13] Welcome to Ideamix radio, I’m Sam Jayanti, and every week I chat with entrepreneurs, solopreneurs, career changers, experts and enthusiasts for insider tips that you can apply to turn your idea into a business. So sit back and enjoy today’s show.

Sam Jayanti [00:00:34] How do you take conversations about something as challenging, beautiful, and let’s face it, insane as parenting and create a comedy studio? Don’t Call Me Mommy is a content creation duo comprised of Haely White and Samantha Gutstadt, who create comedy about moms’ lives. They’ve produced several series, published work for Parents magazine, Romper, FabFitFun commercials and digital content, which together aside over 15 million views. Samantha and Haely, it’s a pleasure to have you on Ideamix radio today.

Haely White [00:01:10] Thank you so much. So happy to be here.

Sam Jayanti [00:01:14] Excellent. So tell us about Don’t Call Me Mommy.

Haely White [00:01:18] So we call ourselves a new kind of content studio. We found that we fit in almost in between like the influencer world and the advertising agency world. It happened very organically, but we’re a creative content studio, so we create everything from digital shorts to web series to podcast and hopefully soon television, all based around mom life. And now we’re branching out a bit.

Sam Jayanti [00:01:45] Excellent. What brought the two of you together to do this?

Samantha Gutstadt [00:01:50] So it’s a story I love to tell over and over. I never get bored sharing this story. Haely and I met actually on a red carpet as red carpet hosts because out of the 10 million jobs that we did when we first came to Hollywood, that was one of them. And, you know, we always stayed in touch and were friends. We didn’t work together at that time. This was years ago. And then I became a mom, and then Haely became a mom, and again, we just stayed in touch. We were both, you know, working on our careers, writing, acting, doing all sorts of things. And we went for drinks one day. I think my youngest was like three, and Haely’s was one. So we were really in the thick of it and we had a couple of drinks and started bonding over how crazy motherhood was. And Haely kind of like, grabbed my hand and was like, why didn’t anyone ever talk about all this stuff or tell me any of this? And we wrote some ideas down, you know, I actually wrote them on a napkin, I think. And I had a pitch meeting the next day and we sold a show. And I remember I called Haely and I was like, guess what? We sold a show. She was like, What show? And I’m like, the one we talked about last night was like, that wasn’t even a formulated show. And I’m like, well, we’re in business, so it’s kind of how we started.

Sam Jayanti [00:03:05] That’s amazing. I love that story. You know, credit to you guys for the spontaneity, for sort of that shared experience, but getting right to it right, like bringing up the brainstorm ideas that you had had the very next day in your pitch meeting.

Haely White [00:03:21] Yeah, it was hilarious because I was like, wow, I knew Sam was a go-getter and we were talking about it. I was like, yeah, you know “shit no one told you” is a really great idea, but it kind of felt obvious, like, hasn’t someone done that before? But then when we started writing it, it just flowed. There was just so much to say about it. And that’s when I realized, OK, we have a lot to talk about in this space.

Sam Jayanti [00:03:43] I love what you just said, Haely about asking if someone has done that before because that’s true of most art and literature that we all know, but there’s always a new take on things that every generation has needs, and these topics are sort of evergreen in that regard.

Haely White [00:04:02] Absolutely. And it was interesting because it was our particular journey at the time, and I didn’t expect it honestly to resonate with so many other people. Sometimes when you’re going through this, you kind of feel like you’re just dealing with it in a bubble. So when we put those first couple episodes out and they got like a million views, it was this shocking moment as, Oh my gosh. Women need to talk about this.

Samantha Gutstadt [00:04:24] Yeah, especially topics that weren’t so easy to talk about. I think we started our first two episodes with topics that felt a little uncomfortable. And I think maybe that’s what was so welcomed because it was something that was uncomfortable. But we were visiting it through a comedic lens and it felt really relatable I think to a lot of people, because it was something that was, I think a lot of women thought about, but didn’t feel comfortable talking about in their mommy groups with their mom friends.

Sam Jayanti [00:04:56] It’s so true. You know, there was an article in 2019 in the Times and I quote, “there have always been moms, but motherhood as a lively public conversation– a set of references to jokes, warring factions, cliches and grievances– has existed for just a little over a decade.” And social media and mommy bloggers were really on the rise between particularly 2005 and 2010, and I think we’ve seen that trend continue. Was it conscious for you both that you were sort of tapping into that relatively recent openness to talking about the realities of motherhood? Did you sort of perceive that as a gap? And and that was the gap that you were trying to fill and to add to that conversation?

Haely White [00:05:44] So no, is the short answer. I had no idea. Sam and I had both been producing content on our own and I had been doing a lot of comedy and about dating, and I had a web series about dating. And then after I had my son, I was like, this is so much harder than dating. What have we been thinking? So I had no idea that there was this rise of women being more candid and talking about it. It just was for me, particularly I don’t know about Sam, where I was at in my life and the comedy that I felt I needed to talk to right about to kind of process the change of my life, the drastic change.

Samantha Gutstadt [00:06:29] And then this is why we make such, I think, a good team because on the flip side of that, I had come in strategically, as you know, a year before Haely and I had met, I had noticed that there was this big sort of gap in what the content that was being put out there. I was starting in the blogger world. I actually had launched a blog for moms, so I guess you could call me a mommy blogger. And I had grown my social media platform in a very strategic way, knowing that I wanted to create content for moms. It was definitely lifestyle. It wasn’t comedy. But I always wanted to do comedy. So I already had started building up that sort of side of my business, and I was following a lot of mom bloggers and seeing the content that was being put out there. And I did feel like there was a space for these moments of motherhood to be told in a way through the lens of comedy. And that’s, I think, where Haely and I blended together like so perfectly because we always joke that, like, I didn’t have that mommy blogger knowledge and a bit of that knowledge and Haely came with comedy, so it’s like we smash the two together.

Haely White [00:07:46] I’m so grateful for Sam’s guidance because she did have this world set up that we just kind of and I could bring my comedy training and we just dropped into it. So it’s interesting to talk about it now because I didn’t really realize that it was so unconscious for me, and Sam was so different. It’s interesting.

Sam Jayanti [00:08:04] I mean, the complementarity between the two of you is sort of very obvious watching your content. And that said, I feel compelled to ask, how well did you guys know each other? Because to make a decision to partner on this and your content seems so seamless. Did it take time to get to that complementarity and discover that sort of yin and yang?

Haely White [00:08:27] So what’s so interesting when we met on the red carpet Sam and I were covering the same event and we were assigned to kind of ping pong these interviews together, and it was seamless. We both just kind of knew when to jump in. It was this very, just easy partnership. So it was funny when we started, when we started working together and filming, it really felt so natural. It always has, and that’s been the best part of it. It’s always just been like fun, truly and pursuing that, that fun. And then we got to kind of just keep going and following that.

Samantha Gutstadt [00:09:06] I echo that, like, you know, they say sometimes relationships just kind of happen and you don’t think about it and it doesn’t take a lot of work to just work. That’s kind of how I felt about my partnership with Haely from the beginning. I mean, we were thrown into shooting a series for a brand before we had ever even worked together, and we learned through our process. I mean, of course, there’s like hiccups like, you know, I sent an email agreeing to a budget before we talked about it, but it took like a quick conversation. Haely and I had such a great way of communicating that we like, say it, laugh about it and move on. And it was like, Boom, we’ll never do that again. It was just so easy in those little growing pains that we had at the very beginning. And that’s what’s I think been so wonderful and unique about this partnership.

Sam Jayanti [00:09:55] I love it. What either of you have done this on your own? Do you think?

Haely White [00:10:00] Yeah, I think so. But it wouldn’t have been as easy, I think. I know I was pursuing it on my own for a while and with another partner. But I’ve always just thrived working in partnerships. It’s just I think with anybody we’re saying before the podcast started, even like, answer these questions, we just kind of know when to flow. We know we really support each other in that way. So I think I would be doing it, But I don’t know if it would have worked out as well.

Samantha Gutstadt [00:10:32] I agree I was actually similar to Haely. I was, you know, doing starting to pitch stuff before, which is why I had a pitch meeting the next day and I had a partner as well and nothing had taken off. And as soon as Haely and I like put our heads together, stuff just started happening. So, yeah, I don’t know.

Sam Jayanti [00:10:53] On that note, let’s take a quick break. So, Haely, you decided to focus on comedy about parenting to start. Tell us why you started there.

Haely White [00:11:07] I can start on this one, I think the drama is too a little too obvious, right?

Sam Jayanti [00:11:12] It’s certainly true.

Haely White [00:11:14] No one wants to know about that. No, but Sam and I are both comedians. For me, that’s been my focus. I learned how to write comedy. I started in sketch comedy, so that’s just my passion and life and as a person and how I show up in the world. So it was kind of organic that that would be the way and the lens that I look at motherhood. But also they say that comedy is pain and there’s a lot of pain in child-rearing, so it felt very obvious.

Sam Jayanti [00:11:49] So you start working together and some of what you do, I imagine works, as you said from the beginning, and there might be some other things that you do together that don’t work and you go through a period of rethinking, pivoting, changing it up. Tell us about one of those times that stand out to both of you where you made that kind of pivot or change. Entrepreneurs and influencers and actresses like yourselves have to do so much of that. So what stands out in your minds?

Samantha Gutstadt [00:12:26] I would say, my idea of our biggest pivot was actually 2020. We are a three-year-old company. We were at the time, a three-year old-company, maybe two and a half years, and we had just signed some huge business. We had signed two or three like big big one-year deals or commercials, which is what we had been aiming for. So we were like, yes, like 2020 starting go 2020. This is like January, right? We’re like, Wow, this is going to be the best year ever. And of course, March happens and production shuts down, and we were trying to figure out how we were going to service these clients and shoot these like really big budget commercials that we were so excited about. And that, to me, was our biggest pivot. We put our heads together and we within that first month of COVID, we signed a deal with Parents magazine, who was a former client to shoot like 11 videos for them. We pitched several series of which they greenlit and we had to shoot those remotely. So now no longer do we have a crew. We’re shooting these on our iPhones, doing our own sound, our own cinematography, Haely’s directing to talent in Austin, me over here in one part of L.A. herself. You know, that was such a pivot, and I was so proud. I remember when I saw the edits. And I remember I talked to Haely and I was like, We pulled it off. And it was that moment that we had the confidence to continue I think creating and 2020 was one of our best years in terms of our business. And I think that’s because we pivoted and we were able to create and do it in a way that felt safe and that we are still able to service our clients. And so to me, that was like my wow pivot moment for sure.

Haely White [00:14:26] And I’m just going to say that I’m really excited for my husband not to be my cinematographer anymore. There are definitely.

Sam Jayanti [00:14:34] I bet he is excited too.

Haely White [00:14:36] He’s like again?? Kids screaming in the background. But like Sam said, it was so empowering for both of us. Well, let’s just say it, 2020 was our  best year. We actually ended up making the most money and having the most content. And although we’re both really excited to go back to real production with the team, it kind of shows you that the pivot is everything and leaning into those moments when you have to make a decision and you have to show up. I remember being in a wig. I was in this crazy mullet made for this character, and I was kind of going through a hard time personally with COVID. I’m an extrovert and I felt cut off from the world, and I remember having breakdowns in between in this mullet wig.

Samantha Gutstadt [00:15:19] And I remember just looking and you were crying in the wig.

Haely White [00:15:23] Yeah, the show had to go on. You know, I would wipe up my tears. I’d demand my husband come into the bedroom to film me, and I would work it into my performance. And it was one of those moments that you, you have to keep showing up as an entrepreneur, it doesn’t mean that you can stop. And I think on the other side of that, it’s really empowering.

Sam Jayanti [00:15:42] It’s such an important point that you’ve just made that I really want to stress for our listeners, you know, I think particularly people who undertake creative endeavors and some of the other guests we’ve had on Ideamix radio pointed out this exact same thing, that there’s this sort of conception that when you’re engaged in a creative endeavor, you should only work when there’s a bolt out of the blue of creativity. But the reality is showing up is half the battle right? And by showing up, the creativity can follow. But if you keep waiting for the sort of creative lightning to strike, you know and only show up when it does then it’s going to be a very difficult endeavor.

Haely White [00:16:27] That’s such a good point. I hadn’t thought of it like that, but even that’s even important for us. Like we’ll be in the edit and something didn’t work. We’ll be like, oh, we didn’t get that shot. Or, Oh no, you know, there’s lots of things that come up the entire time. So you’re constantly having to just think on your feet. And I think you’re right, it’s all about just being ready and showing up.

Sam Jayanti [00:16:51] Totally true. As you guys think about your trajectory and the variety of different content and partnerships that you’ve undertaken, what’s been your most effective method of finding new projects, of selling to new customers? I mean, this is obviously the thing that every entrepreneur deals with and is one of the toughest parts of the business is how do you grow and scale?

Samantha Gutstadt [00:17:22] I mean, I can start with this one. So, For us, a big thing, Haely, and I’ve actually, you know, spoken at events about this because we’re a small business. There’s just two of us. We don’t have a sales team, we do have an agent and managers. But at the end of the day, I like to take the responsibility that we are the captains of our ship. No one’s going to care about our business more than us. So I’m a big believer in like sort of a cold pitch, the cold open. I have always used the model of reaching out and being sort of proactive that way. I don’t like to wait for things to come to our lap and things do. Thankfully, we’ve built over the years that we do get offers. But Haely and I sometimes will put a list together of brands that we’re excited to work with ideas that we have. I’d say like every month or so, we get very fired up and like, write down a list of our goals big and small, and then we go after them. So if there’s a brand we want to work with, like I’ll DM them on Instagram and I’ll say, Hey, who can I talk to at your company to pitch? We put together materials. We make it as easy as possible for a company to say yes. And that’s always been my philosophy. If a company says no, the brand says no, I don’t see that as a no. That’s like a not right now, probably, because a lot of our no’s have turned into yeses and those are our longstanding clients. So that’s kind of been the model of how we’ve grown. It’s going after it. Kind of like brave knowing that you have something to offer, not taking no necessarily as a no, but as an open conversation that you can continue and follow up. Not in a crazy way, but in a gentle way. And to be the captain of your own ship because no one’s going to drive your business better than you and your partners, if you have partners. So it’s kind of, you know, I don’t know, Haely, what if you have anything else to add, but I feel like that’s been what we do, right?

Haely White [00:19:15] Yeah, I think the other thing that we’ve really had success with is just returning clients. We always try to do a follow up with all of our clients and just have a candid conversation like what worked, what didn’t work. You know, one feedback we got once was, you know, make sure that the thing that you deliver is the script you deliver. You know, I’m always going for the comedy and the edit and the improv, and it was a good note to realize that is very important. They signed off on that, and they’re not going to always want the comedy. So hearing constructive feedback from our clients has allowed them to trust us, and I think once you have a brand or business or a media platform’s trust, they will give you more work, and that partnership begins to snowball and build. So that’s also been a huge, a huge thing for us.

Sam Jayanti [00:20:01] You guys have said a few really interesting and important things in there, right? One sort of have goals and pursue them, but also retain the flexibility and the sort of responsiveness to be listening to what your clients are telling you and to react to that. Right? No doesn’t mean no, It could just mean maybe later. And so going back at ideas and not just discarding them as something that didn’t work is super important. And then I think you’ve built an amazing feedback loop with your clients because you have gone back and solicited that feedback and then actually done something with it.

Haely White [00:20:39] Exactly. And then they feel like, OK, good, they’re listening. And it’s only improved our communication, you know, and if we take a trip, we’ll make sure we go and seek out that client. We try to get in front of them. A lot of these people are in New York and we’re not getting face time. So I think and Sam is also really good at this, just always following up, always checking in, even if we’ve just finished something. And it’s kind of an ongoing journey.

Sam Jayanti [00:21:03] Totally. We’ll be right back. So, Sam, as you think back to when you started this as a side hustle, that’s now become more and more of what you do and turned into your full-time gig. Has it turned out the way you both expected it to?

Samantha Gutstadt [00:21:25] You know, I am surprised how organic it’s been, to be totally honest. I have been producing content for 15 years. I don’t want to age myself, but…

Sam Jayanti [00:21:39] You’re ageless.

Samantha Gutstadt [00:21:40] That’s right, honey. Don’t you forget it? But looking back, you know, what’s really interesting is that there’s just been this flow. I truly believe that when your intention is very clear and you show up as one hundred percent of who you are in the world, things come naturally. So I guess that’s it. And also, yeah, we’ve just been we’ve grown in a really beautiful way and we’re constantly educating people kind of about who we are because we are kind of this unique hybrid. You know, I came from advertising and I wanted to bring in that element of it with the branded side. And Sam was an influencer and producer and all these other things. So I think it’s been really fun to kind of bounce between these different mediums. And now we’re starting to branch into TV and it’s just been very organic.

Haely White [00:22:32] Yeah, I mean, I would echo that like this is everything I could have dreamed it to be. If I had sat down a few years ago and said if I could craft the career I want, this is it. And so sometimes I pinch myself and I’m like, I mean, we have a lot of growing to do, but getting to do all these things is exactly what I wanted to do.

Sam Jayanti [00:22:54] Amazing. You both found your sweet spot. It’s the perfect segue way into what do you feel is next for you both?

Haely White [00:23:05] My son going to school, that’s not in my home all my life, so what’s directly next? We’re launching two different podcasts. One is going to be based on our column. Everything is Embarrassing, which are embarrassing moments of parenthood, and that’s going to be a lot of fun. And I’ll let Sam talk about the other one.

Samantha Gutstadt [00:23:31] So the other one is a podcast and also a TV deal. You know, the goal for us has always been obviously, we love creating, you know, short content, branded content commercials. But Haely may really want to, you know, branch into scripted TV work and suddenly like this real-life thing happened to us. And honestly, I always say, and Haely says, it’s too like, you can’t write these things if they happen, It’s gold, right? Like these real moments. And so

Sam Jayanti [00:24:01] Exactly, it’s more authentic.

Samantha Gutstadt [00:24:02] Yeah, we were shooting probably one of the most ridiculous videos of our whole, you know, video career. It was an add on. We had been shooting for a client and we had a crew and we were like, oh, let’s just shoot this thing. It may not work. We actually never posted it because it was so outrageous. but …

Sam Jayanti [00:24:21] You’re going to have to send that to me so I can see it now that you told me about it.

Samantha Gutstadt [00:24:27] And like to set the stage. You know, we have a social media girl with a camera, two camera guys facing all one direction on my street. And then you have like me and Haely these like three guys in crazy outfits, dancing, OK? And Haely is literally in the middle of like a booty slap with a guy dressed like a B-Boy, like a rapper guy. And it was like a robbery going on behind us. But we don’t know. But there is, and we have three cameras capturing the whole robbery from beginning to end.

Sam Jayanti [00:24:55] So the robbery is going on like a real robbery happening, and you’re just not aware of it.

Haely White [00:25:00] Yes. So let me back up. So there we are in the middle of the street, high kicking, booty slapping, just being idiots. And this neighbor comes out running, crying. How long have you been here? How long have you been here? And we’re like, oh, I don’t, I don’t know. Is everything OK? Probably an hour. And she says, My house has just been robbed and we’re like, What? We have cameras facing in the direction. Well, guess who has more footage? We do. Yeah, we’re inside. We’re zooming in on the footage and suddenly we’re solving a crime. Next thing we know the police are there and Sam. Sam’s like, guys, we’re losing light. they wanted to interview us and she’s she tells the police officers to wait. So now everybody is watching us do this ridiculous sketch. So then they can interview us after about what really happened. But long story short, they hired a private investigator and guess what? They found, who did it and all thanks to us. So what happened after this is Sam’s like, we should take it to CNN and I’m like, Yes, let’s do it. And I’m talking to my husband and my husband’s like, absolutely not. You are not. Then they would know who you are. This is a terrible idea and a horrible idea, but it’s a great idea for a show. So that’s how “Influencing a Murder” was born. And now we’ve signed a deal to do it as a scripted. It’s a crime comedy podcast, and potentially we’re in talks to make it into a show.

Samantha Gutstadt [00:26:27] Yeah, and we won’t see more so, but that’s all we can say. It’s there’s a lot of buzz around it, and we hope that we can bring it to your pod wherever you listen to podcasts and your screens in the near future.

Sam Jayanti [00:26:41] That’s amazing. I love that story. You couldn’t have made this stuff up, but it’s just fantastic that you both seized upon this as a wonderful content opportunity to extend yourselves.

Haely White [00:26:52] Oh yeah. You never know when comedy will strike.

Sam Jayanti [00:26:55] I’ll always be ready for it. One last question. What do you feel are your goals for yourselves and your partnership three years from now?

Samantha Gutstadt [00:27:08] Great question.

Haely White [00:27:09] Yeah, I think for me personally, I’ve been directing a lot of Sam and I’s is stuff, and it’s really just what my appetite to keep going. So I would love to start directing some more film and TV and kind of explore that. And then for us, I mean, I’ll let Sam talk after, but I see Sam and I doing TV, film and basically having a production company where then we can have a lot of different creators and people bringing us projects that are kind of under that DCMM umbrella that bring that mix of kind of vulnerability and comedy. That’s really important to us.

Samantha Gutstadt [00:27:51] That’s great. I mean, yeah, like everything Haely said on the business side is the same things that I sort of have as goals for us, like just, yeah, everything, she said, building us up to be this like bigger production company where we do it all. And I picture us having maybe an office with like some full-time staff that work with us and just being this really amazing busy business that gets to do all these different things and has our hands like, you know, we can be executive producing a couple of shows here and still be on set shooting for certain brands here and just all of it. And then on a personal note, I would say I want to keep growing my personal brand, which is like my blog. I love writing and I love sharing, you know, fashion and beauty things with my audience. And I’ve been writing a little more, you know, with our Don’t Call Me Mommy content. So continuing to write with Haely is a partnership, and just all of that actually directed a music video for a friend. And I really enjoyed that. So just continuing, I learned a lot from Haely watching her direct for three years. So I called her after I was like, I learned from you and I tried it. And so just continuing to explore all those creative outlets that really, you know, keep me feeling like me.

Haely White [00:29:08] There’s like nothing you can’t do, Sam. Sam is truly the Renaissance woman.

Sam Jayanti [00:29:13] Well, we love the goals that you guys have for yourselves, individually and for yourselves together, and the way that you both support each other and are always learning from each other in addition to the outside world. So that’s really fantastic, and I compliment you both on that. It’s an amazing partnership.

Samantha Gutstadt [00:29:31] Thank you so much.

Sam Jayanti [00:29:34] Here’s something else you should know. In 2019, the market size of all products and services targeting millennial parents was estimated at forty-six billion dollars, and that’s only set to grow with the advent of the pandemic and the continuation of the pandemic. Thanks to the New York Times and Forbes for the data used in today’s episode. Sam, Haely, we love your story because you took a point of connection and comic dynamic between you and have really decided to share it with the world and turn it into a motivation and engine for amazing content. Thanks so much for being with us on ideamix radio today.

Haely White [00:30:14] Thank you.

Samantha Gutstadt [00:30:15] Thank you so much for having us.

Sam Jayanti [00:30:18] Thanks for listening today. You can subscribe wherever you get your podcasts. And while you’re there, please do review the show. We love hearing from you, so e-mail us at info at the idea makes dot com or Instagram DMs. Our episode this week was produced by the incomparable Martin Malesky, with music by the awesome Nashville based singer songwriter Doug Allen. You can learn more about Doug at Doug Allen music dot com.