A Journey Through Tech, Film, and Fashion with Cake's Founder Dave McLaughlin

Transcript

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I'm Carrie Brett and this is Shot at Love.

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Today's guest is Dave McLaughlin.

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He's a friend, a storyteller and a visionary who's redefined his life at every turn.

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He's gone from films to fashion, transitioning from making movies to making a difference in the tech world, and now bringing us something sweet with his latest creation, cake.

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He'll share his journey in startups, the courage it takes to start over, and why his latest venture Cake is more than just a slice of something decadent.

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It's a whole new way to support creatives and build community.

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Get ready for insights on resilience, reinvention and finding purpose in every chapter.

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You won't want to miss it, so stay tuned.

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Dave McLaughlin began his career as a screenwriter and independent filmmaker, selling selfies starring Donnie Wahlberg and Rose McGowan.

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He then wrote, directed and produced on Broadway shot in Boston, featuring Joey McIntyre, eliza Dushku, mike O'Malley, amy Poehler and Will Arnett.

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Fifteen years ago, dave transitioned to tech startups, launching and selling two companies before joining WeWork as vice president there, he contributed to its rapid rise as part of its leadership team.

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Wework was the fastest growing startup in the world before it famously imploded in 2019.

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This high profile collapse led to multiple book deals in the Hulu series we Work, the making and breaking of a $47 billion unicorn starring Jared Leto and Anne Hathaway.

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Today he's launched a third startup called Cake, an invitation-only shopping community.

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It is my honor to welcome Dave McLaughlin to the show today.

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Hi, dave.

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Hi, what a great introduction.

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Thanks.

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Coming from a filmmaker and a storyteller, that's high praise, so I'm excited to have you here today.

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Things have come circle for us.

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We have been friends for 30 years and we always find something to do creatively.

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You are just such a cutting edge person and your career is so fascinating.

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Tell us what you're working on now.

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So we started a new business called Cake that you mentioned.

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It's an invitation only shopping community.

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Our mission is to give great shoppers more, just more.

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And the idea is that there's a set of women who love fashion, who love shopping, who love discovery, and those women don't get rewarded in the marketplace the way that they should, because they spend a lot of time and energy and money shopping and they just don't get seen by the brands in the way that they should because their money is distributed across different brands and different retailers and so on.

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So it's not like the old days, you know, when you went to Bloomingdale's on a Saturday and you got all your points at one place.

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So we've kind of created cake to give these great shoppers more.

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The way it works is you have to be invited to join.

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It's a hundred dollar membership fee, a hundred dollars a year, and then you get exclusive access so you get to shop new releases from really coveted brands earlier than anyone else.

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You get gifts with purchase that aren't available to the average consumer.

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You get invited to experiences and events with other amazing people and you get thousands of dollars to shop the full collections of these brands these brands for a shopper who you know really wants to be on the leading edge of discovering gorgeous brands and making that part of how she shows up in the world and in her life.

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It's an incredible opportunity and the brands love it because those are the shoppers they want to meet.

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Right, the quality people that are so excited.

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I mean, you're building a movement, you're building something that hasn't really ever been done before.

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No, it's, it's a different take and it's really a reflection of, like the world right now.

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What happens for the brands is they're all super dependent on Instagram ads and and digital ads on other platforms, and so those companies like, if you think about it, meta, google and Amazon control something like 65% of all the digital ad spend, so they have huge leverage in terms of what they can charge brands to place those ads, and so the brands are getting killed on that strategy and they just need another way to connect with the kind of shoppers that they've designed their products for, and so we give them a new way to do that, and it's a way that is really, you know, we really love the brands.

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We celebrate the brands, we put them on a pedestal and then we make it so that it's amazing for the consumer too.

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We basically let the consumer and the brand connect in a way that's better for both and less money goes into, you know, facebook's pocket and more money goes into the pocket of the shopper.

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I like that.

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That's really good.

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It kind of reminds me a little bit of we work, in a sense, where it's something that's never been done, it's something that everyone's excited and you're building this community, and I think that was one of the strategies that really worked was that it was the place that you wanted to be seen.

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It was the place that you wanted to be and I know, working at the Improper Bostonian for so long, that was to be featured in the Improper to be at the party in Improper Bostonian, just to be featured in the improper to be at the party in proper Bostonians, just to be seen and included.

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That's a selling point as well.

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Do you see the crossover?

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Yeah, I think there are many things in life that way.

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You know, look, we want to do great work and we want to be with great people and we want to show up in a way that puts our best foot forward, like we all want that and we should.

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You know, that's, that's part of how we find the opportunities that are going to be really profound and transformative for us, and so that may be, you know, what I put on my body and that that looks great on my body and how I show up in that sense, and it's also who I associate with and where I find those people.

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And yeah, I remember, obviously, when we were making films and you know we were always kind of involved around the impropers, parties and all that kind of stuff.

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That was a fun time and there were always a whole bunch of great people doing interesting things and like, yeah, life has more energy when, when that's the case, right.

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Yeah, totally, and I think about it and I didn't realize all the different things.

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But we were these young 20, 30somethings who chose great clothes to wear and had an attitude and were kind of cutting edge on a lot of things and I think we didn't know it.

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We were just kind of doing it and didn't think about it so much like how we presented ourselves in the world, I think because we were so young.

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But I can remember you've always had this great sense of style, so I don't know if you thought fashion was going to be your future.

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I'll take the compliment, but I'm not sure it's totally deserved.

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You know, I think for me from a young age I've always been kind of greedy for things that give me energy.

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And so.

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I was always seeking out projects and people that I that I found energizing.

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And early on.

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That was writing plays and and writing screenplays and connecting with filmmakers and making independent films at a moment in time when independent film in America was really rich and exciting and so on.

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I'll be honest, I didn't think that much about what I wore or how I showed up in that.

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I just was.

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I just was jazzed to be around that work in that group of people that were doing that work.

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Right, and when I think about online dating and wearing clothes that makes you feel better about yourself and putting your best foot forward and showing up, I'll tell you all day long, it's energy that you bring, other than the pair of jeans, really, whatever gives you that courage or that charisma that in that moment, this business has been super interesting for me because I honestly never have have spent that much time thinking about fashion and thinking about, you know, the story that we tell with, with kind of what we put on and how we present ourselves, and I've really come to appreciate, you know, how creative that is, how fun that can be, how expressive that can be and here's the thing how personal that is.

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You know, because this business is really focused on women and and how women think about shopping and fashion is so different than how men think about it.

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Men are really needs driven and event driven.

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It's like I have a wedding, I need a suit for a wedding, or I have a job interview or whatever.

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For women it's just so much more textured, it's just so much more layered, it's so much more I don't know it's it's more expansive, like there's a greater range of choices and stuff like that.

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And one of the earliest things I did when I was starting this business is I just interviewed a whole bunch of women about tell me how you shop and and and took that through and it was so fascinating to me because very similar women shopped in very different ways, like.

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I'll give you a simple example how people um store the things that they find on the internet that they're inspired by.

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You know, there's some women who create massive Pinterest boards of outfits that they like and items that they found, and so on, and somebody else they just throw it in their basket on Instagram reformation or revolve or whatever and then they just leave it in their basket forever and they keep coming back to it, and so it's a pretty difficult, like the condition of the world now is we have this abundance of choice and that's an amazing thing, and yet, like how do I?

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navigate all that choice, cause it's a lot to to track and hold on to and think about and put together, you know, this item with that item and so on.

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So I found it really fascinating to learn more about that and to continue learning more about that.

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And I think what we're trying to do with Cake isn't it's not necessarily that deep all the time Like it should be fun.

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It should be fun to find amazing things and, and you know, you should feel special when you get special treatment from those brands that are designing and creating these amazing products.

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And that's what we're trying to do with Cake.

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It's really about this shopper who, in the kind of standard way of shopping, she's not seen.

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She's not seen for how special she is and how valuable she is and Cake is about.

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We can see her and we can celebrate her and reward her and give her more.

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I like that.

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It makes you think about this community piece and making connections and strengthening the connections with the customer through giving.

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I saw a friend this morning at Starbucks and I'm like I love your sweatshirt.

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She's like this is the brand.

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I start talking to her about cake.

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She's like I want to hear more about this.

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She has a huge brand herself.

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She has a yoga studio all women.

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So how do we all connect and grow this community?

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It's, it's pretty fascinating because it brings us all together in a way that I didn't know I'd be talking about this morning at Starbucks.

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I didn't know I'd be talking about it either.

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I think, um, I think the interesting thing about starting businesses this is my third business, if you don't count.

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You know films and plays and stuff which are kind of ventures in their own right, um, but this is my third.

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You know, startup, especially at the beginning, it has to be for someone.

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You know there's this saying we we refer to sometimes of like you should try to be everything for someone, not something for everyone.

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And I think, like, even if you take your photography studio, you know you have a persona or a few personas that tend to be your customer, that really you just nail it for, obviously, you can make photos for other people and other scenarios and stuff like that and you do.

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But like, the bulk of that is probably like a pretty specific set of personas.

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And the same thing is true for cake.

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It's a pretty specific shopper that you're trying to serve and empower and inspire.

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And then obviously, as the business grows, it can start to broaden.

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But at this point it's really like this shopper who she's an interesting shopper because she spends more than the average American consumer, but she distributes it, like I said, at different brands and retailers.

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She may shop Jenny Kane's site and pay full price and she may shop Zara and this kind of combination of high, low and how she puts that together, like she's a little tricky to um to describe her very simply.

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But but she wants newness, she wants, you know, fresh quality and she wants these kind of beautiful brands that are not brands that discount all over the place, that are not brands that you know it's easy to get special access to.

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Right, I like this and I like the exclusivity piece of cake and everybody wants to be invited in.

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We're going to talk about that exclusivity piece later in this episode and I think everyone needs to tune in because we have something special for the listeners at the end.

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But I want to talk about your resiliency, your ability to start new chapters and find a path forward, because things weren't always so pretty behind the scenes for you.

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You definitely grew and evolved and you had to always reinvent and create the next big thing.

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So let's start at the beginning, so that we can give some tips for taking chances and doing all the things.

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We met in Boston in our early 20s when you were this up and coming playwright and hotshot filmmaker.

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Okay, I'll take it.

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So I want to go back to that.

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Dave McLaughlin, you first wrote Southie and that starred Donnie Wahlberg and Rose McGowan very cool.

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And then I was able to be a part of your film on Broadway and be behind the scenes and I learned a lot during that experience.

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It was a really big deal back in 2006.

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Talk about what you learned from that or how cool that was.

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I think anytime you try to do something difficult, you expect a certain amount of adversity in that and like it's, it's just what you sign up for.

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So when, when you talk about you know things weren't always so pretty like, I just want to qualify that and say that's not in any like woe is me sense.

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That's just like part of the journey.

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I don't care what you're trying to do, like it's going to be hard, things are hard.

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You're not going to have your best stuff every day and you're going to hit some headwinds and all that kind of stuff.

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So in my case, early on in my twenties and my early thirties, that was about making films and, um, yeah, it's a challenging industry.

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Everybody understands that and the right you know, backing and all that kind of stuff when you're trying to make films.

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Like that's a challenging road.

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But again, that's part of why it's awesome.

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That's part of why it's epic is because it's so difficult.

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Right, and because it's so difficult, you made it.

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Everyone talks about writing a movie, a screenplay, getting it on Netflix or writing a book, and you did it, so you should give yourself a lot of credit and, for people who have dreams, you gave us the opportunity to dream big and bring Hollywood to Boston, which is really what you did.

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Well, you know what?

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I appreciate that and also, like, let's have a more honest conversation, if we can, like I'm proud of the work I've done and also, like I made two independent movies, I'm doing something different.

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Like what I'm trying to say is, um, we had some success with some projects and we had some failure with other things, and and that's fine, and I I don't actually love to talk about the success without talking about the failure.

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Makes sense, because I'm actually proud of all of it.

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I get it.

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And I think that it's good for people to understand that If I were out there listening to this and there was somebody on there talking about like everything in their life was, I'd be like you know, bullshit.

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I just think it's more interesting to talk about the reality of trying to do ambitious projects, which is some things click and some things don't and some things hurt badly and other things you know make you walk a little lighter, and all that kind of thing.

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I always think about this moment Lance Green and I Lance was an actor and a producer on on Broadway and Lance and Joey McIntyre and I were out in Michigan at a film festival in this little beach town on Lake Michigan and they converted a yacht warehouse into a screening you know, space for like 900 people to watch the movie.

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I watched the movie.

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We do a Q&A, we had this great conversation, you know it was kind of standing ovation and stuff like that and that felt good.

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At the end, lance and I were walking down the street in this little town and this couple came up to us and stopped us on the street.

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The guy was Jamaican and he started talking to me about his relationship with his father, because that was kind of a theme in the film and as he was talking to me he started crying.

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It was just this moment of like.

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This is why you make art is to connect with people, and that's a moment that literally two other people saw, lance and the guy's wife.

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But I've thought of that moment 1000 times since then because that was one of the most fulfilling moments as an artist and as a writer and as a director.

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That was a moment where you know a story did what it's supposed to do, which is bring people together and help them see each other as fellow travelers or whatever.

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I think that my work as a filmmaker was hot and cold, but there were moments in there that I treasure, that I would never, I'll never forget and I'll never not be grateful for.

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You know I'll never forget and I'll never not be grateful for, I think to me someone who has always dreamed big Jack Canfield said that you're never given a dream that you can't make happen.

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I think for the person listening, they want certain things in their life and this is not happening.

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But I think part of the reason it may not be happening and I know that we're all guilty of this is that we do hold ourselves back because of fear.

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We're afraid, we're afraid to fail, we're afraid to go to that meeting and say the wrong thing, or go on that date and say whatever and have whatever go sideways.

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And I think the way you frame up the misses let's just say positively allows you to move forward.

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And I like when you said the projects didn't die on the vine because the industry had changed, you found an unexpected path that led you to the next move.

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So you found this book called the Rise of the Creative.

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Is that the name of the book?

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Well, what happened was I had moved back to Boston from LA and I was reading a book by a guy named Richard Florida about the creative economy, and in that book he kind of had this thesis that all artists are entrepreneurs.

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And I just I had never thought about that before and it suddenly made me look at my own experience in a different way, where I was like, yeah, you know, I was writing scripts like that's essentially creating product.

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I was building teams, I was raising money, I was negotiating all these complex rights agreements around these um stories that I was writing Like, holy cow, I might be an entrepreneur, like that was literally how I, how I started to sort of frame myself that way and started to get interested in entrepreneurship.

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And once I got that idea in my head, you know, I just ran with it.

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My job at the time had me meeting a lot of there were a lot of really interesting startups in Boston.

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This was around 2006, 2007,.

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A little later maybe, and it's like when the smartphone was starting to really become prevalent social media you know, facebook launched in 2006,.

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Linkedin, there was all this kind of interesting wave of opportunity.

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And also in 2008, we had this big financial crisis, when the world was all doom and gloom and Boston was such a big finance community, you know, felt that really hard.

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But I was in these rooms with all these startup founders who it was like there was extra oxygen in the room.

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They were just energized about all the opportunity in the moment and I just love that.

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I find that kind of perspective a little bit addictive, I think, like I just find it exhilarating and I just you know.

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So now I had this new narrative in my head, because I happened to read a book that sort of gave me that narrative.

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And then I had this network that I was starting to build because I was just fascinated and curious and wanted to get closer to this stuff and meet people.

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And I found that it was a community that was really ideas driven, like it didn't matter what school you went to or any of that, as long as you showed up with like a and that kind of perspective, you were welcome in these conversations.

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And then I met these two guys from MIT and we partnered up and we started an early mobile payments company.

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This is in 2010.

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And we sold that to eBay when PayPal was still part of eBay, and that technology became part of PayPal's mobile payments stack, and then I took that and I went and started a video messaging company and that was something that we were probably a little bit ahead of the right time for it.

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It would have been better to start closer to the pandemic, probably, but we did a lot of business and I wound up selling that company in 2014.

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And then, as you said, I went to WeWork at that point, and I went to WeWork because I had I had kind of you know started a couple of companies.

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I felt there was like I just loved the energy of it and the experience of it and I I felt that I had some, some good strengths in that space.

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But what I really wanted to learn was what's it like when you're in a startup that's growing like a rocket shit, like like that just seemed so fascinating to me.

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I had a few friends that were in like what we call hyper growth startups and I and I just was like, wow, how do you navigate that velocity and that scale and not screw everything up every day?

00:21:46.067 --> 00:21:51.406
And I wanted to go to a company that would let me kind of build that muscle and build that capability.

00:21:51.948 --> 00:21:53.691
And somebody I knew said you should come to WeWork.

00:21:53.691 --> 00:21:56.215
And I thought, well, I don't know, I'm not really a real estate guy or whatever.

00:21:56.215 --> 00:22:00.171
And they were like look, just come down and meet with Adam Newman and you know, see if it's interesting.

00:22:00.171 --> 00:22:12.791
And so I did, and I got talking to Adam and and and started to understand the business and was like great, I just jumped in with both feet and and and had a ball Like it was so interesting.

00:22:12.791 --> 00:22:22.260
When I went there, you know, I was leading the community globally across 43 countries and leading the membership experience and involved in the business in pretty broad ways.

00:22:29.305 --> 00:22:31.048
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00:23:37.872 --> 00:23:51.012
It just reminds me of how he started the company, where he would literally be talking about it and then be like do you want a job?

00:23:51.012 --> 00:23:52.237
Do you want to start tomorrow?

00:23:52.237 --> 00:23:55.387
Like that's how he put together teams in a sense.

00:23:55.387 --> 00:23:57.830
Who Adam, it seems.

00:23:58.692 --> 00:23:59.372
Yeah, I don't know.

00:23:59.613 --> 00:24:01.034
I don't think he thought it all out.

00:24:01.034 --> 00:24:04.057
I mean, I don't think anyone could think it out that far.

00:24:04.057 --> 00:24:11.905
When I think you said, when you started there was 400 employees, it went to 1600 employees.

00:24:11.925 --> 00:24:15.510
the first year when I started, we were 400 employees and we grew to 16,000.

00:24:15.851 --> 00:24:19.015
Okay, and so that was an amazing kind of journey to be part of.

00:24:19.035 --> 00:24:24.560
Because, like, just, you know what happens when you're growing that fast is you just break all your systems all the time.

00:24:24.560 --> 00:24:39.634
And so if you want to challenge, you know you go into a company that's growing at that kind of rate and what happens is you figure out a way of working in that pace and that intensity and that velocity and then, because you're growing so fast, you actually break your own systems and then you have to remake them.

00:24:39.634 --> 00:24:51.846
And so for me, like someone who loves to just always be like re-imagining and re-envisioning and redesigning, it was a place to do that and just figure out how to take on more and support bigger teams and all that kind of thing.

00:24:51.846 --> 00:24:56.833
As far as Adam goes, adam's a fascinating guy, incredibly brilliant in a whole bunch of ways.

00:24:56.833 --> 00:25:13.471
The genesis of that company was before I was there, but but really you know they and he's told this story many times and people can find it but basically they found a landlord and they convinced the landlord to give them some space and they chopped it up and made it into coworking and other people had done coworking.

00:25:13.471 --> 00:25:18.340
There was an amazing company in Boston called Workbar a guy named Bill Jacobson, who's just a super guy.

00:25:18.340 --> 00:25:26.711
They were doing kind of flexible office space and coworking in a, in a little basement space, uh, right near South station, and so, like a lot of people had done it.

00:25:26.810 --> 00:25:43.778
But I think what Adam and that early team did is they had a vision for this as a wave and as a as a movement and transforming commercial real estate that nobody else had quite had, and he had this unique ability to go out and raise the capital to actually do that.

00:25:43.778 --> 00:26:06.855
And so it was a profound journey and, for all the things that the business you know got wrong and the ways that you know, it was a pretty fabulous implosion when it happened and it was incredible like to be in the middle of that and experience all that and then to experience coming out of that, getting back to Wall Street, having a successful SPAC, like all the things that we did from there.

00:26:06.855 --> 00:26:19.864
I think that, at the end of the day, that business created a category Like if you're starting a business now, I mean I'm starting one, I'm not signing a lease, I'm a WeWork customer now, you know.

00:26:19.864 --> 00:26:28.041
And so when you think about they really transformed the way that people use real estate, commercial real estate, which is the largest asset class in the world.

00:26:28.503 --> 00:26:36.307
It was pretty epic for folks that have watched the thing with Jared Leto and Anne Hathaway and so on.

00:26:36.307 --> 00:26:40.741
Like you know, that's a take on it and that's fine, and people always say to me is that what it was like?

00:26:40.741 --> 00:26:54.640
And it's like, yeah, well, somewhat, but like there's a much bigger story around that, and the main thing I would say about my time at WeWork is there was an awesome group of people there, like great, smart, driven, you know, funny, friendly.

00:26:54.640 --> 00:27:02.386
It was just a great group to be part of and a real privilege, even though it didn't work out the way that you know we had hoped it was going to work out.

00:27:02.867 --> 00:27:04.148
And I think that's what you have to do.

00:27:04.148 --> 00:27:19.316
You have to say we're in this, we're in it to win it, and you have to have this then like mindset for figuring things out, because you have all this coming at you and that's where you became really good at let's do this.

00:27:19.316 --> 00:27:22.465
It may not be perfect, but let's continue on.

00:27:22.465 --> 00:27:30.903
When you were doing it, you didn't think that you'd lose personally millions of dollars and all this like, but I'll collapse.

00:27:30.903 --> 00:27:37.377
I don't think you can ever attempt to do anything thinking that it's going to implode the way it did.

00:27:38.339 --> 00:27:40.705
It's in simple terms, like there are inputs and outputs, right?

00:27:41.146 --> 00:27:42.557
And so you can control the inputs.

00:27:42.557 --> 00:27:48.780
You know what do you do here, how do you work at it, you know all that kind of thing and you can't always control the outputs.

00:27:48.780 --> 00:27:54.143
I'm always kind of like look, is this a project that I'm fascinated by?

00:27:54.143 --> 00:27:58.480
Are these people that I want to spend this huge number of hours with?

00:27:58.480 --> 00:28:03.038
And then, if it comes together in the way that we believe it can, amazing.

00:28:03.440 --> 00:28:13.116
And if it doesn't, I still won, because, you know, I did this work that challenged me and stretched me and forced me to grow, and I made a new set of friends and a new set of relationships.

00:28:13.116 --> 00:28:25.986
And you know, like we're learning every day, Like we're all you know, none of us have all the answers, and so, the more that we can and this is maybe a personal statement like I don't know that everybody thinks this way or should think this way, but people can kind of pick their own path.

00:28:25.986 --> 00:28:34.368
But for me, I always want to be in situations where I'm really being challenged and and forced to just get out of my comfort zone and learn.

00:28:34.368 --> 00:28:45.060
And as long as I'm getting that, like I said before, I'm kind of greedy for that energy, and so I've just always sort of sought out things that give me that energy, you know.

00:28:45.394 --> 00:28:48.885
I think you are more greedy for the experiences.

00:28:48.885 --> 00:28:56.635
They say that the juice of life is who you become in the process, and so you look for real, challenging things.

00:28:56.635 --> 00:29:04.789
Obviously, look at your resume to grow and to evolve as a human being, I think.

00:29:05.255 --> 00:29:08.442
Yeah, I mean, you know, thank you, I'll take that as a big compliment.

00:29:08.442 --> 00:29:12.019
That is kind of the way I'm wired, and and again.

00:29:12.019 --> 00:29:16.518
Like you know, they don't all work and some of them are painful when they don't work and so on.

00:29:16.518 --> 00:29:20.326
So I'm not trying to put too much of a rose colored glass on that.

00:29:20.326 --> 00:29:21.076
But yeah, that is.

00:29:21.076 --> 00:29:23.059
That is sort of my DNA.

00:29:23.661 --> 00:29:33.422
But I think what's great about you is that when things fall apart because it happens I mean the Improv of Bostonian we didn't fall apart.

00:29:33.422 --> 00:29:43.817
We're just closed now after 28 years and that was a lot hard loss for me, but I can't really complain because look at the run that I had.

00:29:43.817 --> 00:29:48.227
I just feel super grateful that I had those experiences yeah, come on.

00:29:48.287 --> 00:30:02.042
I mean, you know, as your friend and and we've been, you know, friends a long time like, think of the, the rooms that it put you in, the people that you got to meet, how much you grew as a photographer, the different challenges of what you had to shoot.

00:30:02.042 --> 00:30:06.862
It's not even a question, that was an absolute blessing and you made the most of it.

00:30:06.862 --> 00:30:11.084
So I'm not saying it's a blessing like you didn't deserve it or drive it or whatever.

00:30:11.084 --> 00:30:18.279
I'm saying, like you know, life has a combination of like things that present themselves to us and then what we do with them.

00:30:18.279 --> 00:30:23.563
Right, and I just look at your time at the Improper and go like it was amazing, like what's even the question?

00:30:23.943 --> 00:30:26.222
I know and when I think about on Broadway.

00:30:26.222 --> 00:30:45.134
When I did that cover with Michael Mellie, amy Poehler, joey McIntyre and Eliza Dushku, amy was coming driving from New York after she just shot Saturday Night Live and we waited, like it was like I think I was on the set for like 14 hours.

00:30:45.295 --> 00:30:46.157
Well, those guys were.

00:30:46.157 --> 00:30:51.785
I mean, they were so generous in terms of how they participated in that movie and supported that movie.

00:30:51.785 --> 00:31:01.703
It was just this little movie, but you know, what we did really was we basically got all these great Boston native actors to come back and make this little love letter movie together.

00:31:01.703 --> 00:31:03.613
Again they were just incredible.

00:31:03.613 --> 00:31:10.215
I remember Will saying to me like hey, I don't need to get paid, but like like you know, is the food going to be good?

00:31:11.819 --> 00:31:13.683
And it's like, yeah, we'll make sure we have good food.

00:31:13.683 --> 00:31:16.176
You know, everybody just kind of jumped in that way.

00:31:16.176 --> 00:31:18.343
Again, you talk about the experience.

00:31:18.343 --> 00:31:29.544
Well, what an amazing experience to have friends who support you that way and who participate that way, this is a nerdy quote, but there's a guy named Joseph Conrad who wrote a lot about myth.

00:31:30.226 --> 00:31:39.275
He's the one who created the term the hero's journey and sort of like distilled, like what is the narrative arc of the of the great myths and that hero's journey?

00:31:39.275 --> 00:31:49.406
And, um, one of the features of the hero's journey and Joseph Conrad's words is the hero takes one step toward the gods and the gods take a hundred steps toward the hero.

00:31:49.406 --> 00:31:57.028
In other words, you got to put yourself out there if you want to create the possibility of the other things that can happen.

00:31:57.028 --> 00:32:04.628
And so, if we use the example we're talking about, you know, I had this amazing experience of these great friends being so generous and supportive to me.

00:32:04.628 --> 00:32:06.721
Well, that's a gift.

00:32:06.721 --> 00:32:14.904
But also that gift couldn't have happened if I hadn't sat down one day in front of a blank page and wrote the script and, you know, started the thing.

00:32:14.904 --> 00:32:19.131
So we sort of catalyze stuff and then we have to just be open to what happens as it happens.

00:32:24.974 --> 00:32:53.044
I think that's been a lot of my experiences, like starting things and catalyzing a sequence of events without knowing what they're going to be, and and there are some things in there that are incredible, like that conversation with that Jamaican man on the street in Saugatuck, michigan, and there are some things in there that are devastating, like when a business doesn't work or, you know when you realize you can't find the right distribution deal for the movie that you made or whatever it might be, or even even more micro things, when a conversation goes sideways with somebody who's on your team or whatever.

00:32:53.044 --> 00:33:00.665
Like there's just every day is challenges and you just kind of have to be open to it and understand that like.

00:33:00.665 --> 00:33:03.961
One of the other things I like to remember is it's usually not personal.

00:33:03.961 --> 00:33:18.583
You know, when something doesn't work out or somebody, even when somebody does something really negative to you which happens right, it's usually not personal, it's usually about that person's stuff and you know whatever they're going through and projecting and all that kind of stuff.

00:33:18.936 --> 00:33:32.979
But you're curious and you are open and you bring this energy that who knows what can happen, like some amazing things can happen today, and I feel like I'm a little bit like that too when I think of Will Arnett.

00:33:32.979 --> 00:33:42.306
He slept on your couch while he was trying to make it in the industry and now he just sold his company for his podcast.

00:33:42.306 --> 00:33:46.241
He's just created a new company for his podcast and got this incredible deal.

00:33:46.241 --> 00:33:49.122
And you didn't think that.

00:33:49.122 --> 00:33:50.299
He didn't think that back then.

00:33:50.299 --> 00:33:50.961
It's so cool.

00:33:50.961 --> 00:33:55.501
And when I got a chance to photograph him, it was not even planned.

00:33:55.501 --> 00:33:59.242
It was like, well, why don't I shoot all the actors while I'm here, we're waiting, and?

00:33:59.242 --> 00:34:05.585
And he did all these crazy poses and and I just went with it.

00:34:05.585 --> 00:34:15.605
None of it was planned, but those great moments came out of something that I had no idea was going to happen that day yeah, yeah, I'm a big believer, a big believer in what you're saying.

00:34:15.644 --> 00:34:21.902
Like you know, you kind of create these spaces and then you just sort of open to what happens and you try to be grateful for what happens.

00:34:21.902 --> 00:34:24.896
And you know, will's a great guy and a great friend.

00:34:24.896 --> 00:34:39.784
We had this period of time in our twenties where I was living in LA with my wife Beth, and Will was living in New York on the Upper West Side, and when I needed to be in New York I'd sleep on his couch and then he would come out for pilot season and he would sleep on our.

00:34:39.784 --> 00:34:40.668
We had a futon.

00:34:40.668 --> 00:34:44.585
We had a little one bedroom apartment in the Valley and we had a futon and he'd sleep on the futon.

00:34:45.215 --> 00:34:45.677
And.

00:34:46.358 --> 00:34:54.688
Will had a big voiceover career and so I remember one year he was there for like three weeks in a row in this 700 foot apartment and he's sleeping on the futon and everything.

00:34:54.688 --> 00:34:56.750
We're happy to have him, but also like it's a small space.

00:34:56.750 --> 00:35:02.898
He was getting ready to fly back to New York and we folded up the futon and stuck it in the closet and, you know, have a hug, and he leaves.

00:35:02.898 --> 00:35:06.795
And, uh, I turned on the TV and the first three commercials were all his voice.

00:35:06.795 --> 00:35:14.045
It was like GMC trucks T-Row price and I forget what the other one that he was doing at the time was and it was like, oh my God, you can't get rid of the guy.

00:35:14.085 --> 00:35:21.726
You know, he was incredible and supportive and, like we said when, when then I was making on Broadway, he was the first one to say how can I help?

00:35:21.726 --> 00:35:24.244
You know, do you want to come do something in this?

00:35:24.244 --> 00:35:25.614
And he was already a big star at that time.

00:35:25.614 --> 00:35:35.847
But it's been, it's been so fun.

00:35:35.847 --> 00:35:40.458
But, but this podcast that they've created, uh, smart list, is amazing.

00:35:40.458 --> 00:35:50.617
They came to Boston, they did this sort of thing on the road and and had a chance to catch up with them then and and and meet the other guys and so on and, um, yeah, just so happy for him.

00:35:50.617 --> 00:35:54.663
You know, I, I that's another thing I really feel is like I love seeing people do well.

00:35:54.663 --> 00:35:56.545
I love seeing good people do well.

00:35:56.545 --> 00:35:59.617
It just that's another one of those things that makes me happy.

00:35:59.617 --> 00:36:12.045
And I don't know, some people have a different reaction when other people do well, but I would just encourage people, like, just try to be happy for people and again, I think that's the right energy and it's a lot more fun.

00:36:12.427 --> 00:36:13.389
It is Well.

00:36:13.389 --> 00:36:24.463
That just shows you're such a true creative, because you know that there's enough to create and there's new things all the time, and you don't have this lack mindset and when someone wins, we all win.

00:36:24.463 --> 00:36:26.702
Really, I feel like that too.

00:36:27.574 --> 00:36:31.425
And you know, if you've tried to do anything, you know it's hard.

00:36:31.425 --> 00:36:35.797
Number one, it's hard and number two, there's a lot that's beyond your control.

00:36:35.797 --> 00:36:47.347
And so when something awesome happens you know this show that you've created, this photography business that you've built, pick any other person has some awesome things happen.

00:36:47.347 --> 00:36:54.407
I'm always just like that's awesome, because like it's really hard and and there's a lot that's a little beyond your control.

00:36:54.407 --> 00:36:59.045
And when somebody comes out on the right side of that, it's like how can you not cheer for them and just go, let's go.

00:36:59.335 --> 00:37:22.742
That that gives me energy to, kind of, you know, keep pushing at whatever I'm pushing at and that's why, when I started talking about on Broadway, and because you did something so big that we could all be a part of and we all have those memories, and my brother was in it- but here's what's cool, carrie.

00:37:22.981 --> 00:37:28.826
You know you're describing it as so big and yet I have to believe that almost every listener of this show has never heard of it.

00:37:28.826 --> 00:37:34.722
What's cool is anything that you're doing, whoever's hearing this.

00:37:34.722 --> 00:37:37.027
If that's big to you, that's big.

00:37:37.027 --> 00:37:50.907
It doesn't have to be the 10 commandments with Charlton Heston, right, like if it's you exploring something, discovering something, expressing something, learning, growing, getting a little better.

00:37:50.907 --> 00:37:51.757
That's big.

00:37:51.757 --> 00:37:53.702
It's not so much about.

00:37:54.403 --> 00:38:06.599
There were moments with that film like we went to the Galway Film Fla in 2007 and we won a big award and it was like, oh, that's pretty cool to take this sort of Irish American movie back to Ireland and and have it recognized there.

00:38:06.739 --> 00:38:09.507
That was like a nice moment from a recognition point of view.

00:38:09.507 --> 00:38:14.467
But it's not like that moved the needle for how that movie got released or anything like that.

00:38:14.467 --> 00:38:17.614
But it's not like that moved the needle for how that movie got released or anything like that.

00:38:17.614 --> 00:38:24.855
So there are moments that you know you have to just kind of define them as important to you and enjoy them, even if other people don't get it or don't care or whatever.

00:38:25.454 --> 00:38:28.304
And I think that's what it looks like.

00:38:28.304 --> 00:38:45.820
You just can't please everybody and as soon as you set your foot on a path to do something that's difficult and a little bit ambitious or whatever, just expect that a lot of people aren't going to understand it, people are going to criticize it, people are going to have something to say and again, it's not personal, it's like their own stuff.

00:38:45.820 --> 00:38:54.224
You just have to kind of keep going and keep building and you know, some people kind of come around and get excited about it and other people don't, and it's okay.

00:38:54.224 --> 00:38:57.047
People kind of come around and get excited about it and other people don't.

00:38:57.208 --> 00:38:58.070
And it's okay.

00:38:58.070 --> 00:38:59.331
It's not really about them.

00:38:59.331 --> 00:39:01.153
It's about you and the work you know, right?

00:39:01.153 --> 00:39:01.635
No, it's true.

00:39:01.635 --> 00:39:09.579
And when I think about this podcast, I really, truly said if one person listens and if I help one person, I already won.

00:39:09.579 --> 00:39:15.206
Isn't that great to ever think that, as you're telling these stories about Will, he's a fellow podcaster.

00:39:15.206 --> 00:39:16.347
He would love to listen.

00:39:16.347 --> 00:39:18.130
You know these are as you were telling these stories about Will.

00:39:18.130 --> 00:39:19.733
He's a fellow podcaster.

00:39:19.733 --> 00:39:20.353
He would love to listen.

00:39:20.353 --> 00:39:21.414
These are fond memories for him as well.

00:39:21.414 --> 00:39:23.275
Did I ever have you on the show that maybe someday he would hear?

00:39:23.275 --> 00:39:24.601
That's not the intent.

00:39:24.601 --> 00:39:27.103
The intent is let's show up.

00:39:27.103 --> 00:39:29.342
I'm excited about helping people find love.

00:39:29.342 --> 00:39:31.041
You're excited about your new company.

00:39:31.041 --> 00:39:43.960
This is why we're here today, and I think that's the way it's like, the true, genuine way to you know, just stay with this stay with this term show up, like I think so much of this conversation that we're having is about.

00:39:43.980 --> 00:39:57.925
How do you show up, how do you show up for yourself, how do you show up for your friends, how do you show up around the things that you want to create in your life, whether that's a relationship or a business or a piece of artistic expression or you know whatever like?

00:39:57.925 --> 00:40:05.306
How do we imagine these things and start to give shape to them and show up and kind of put in the work and so on?

00:40:05.306 --> 00:40:21.719
One of the biggest things I often tell people when they're starting something new is expect the dip, and the dip was a term that Seth Godin wrote this book, I think it's called the dip and basically what happens I'll see if you identify with this you you probably will which is like you have a new idea.

00:40:21.719 --> 00:40:34.646
Let's say, when you started this podcast and you're gung ho, you're fired up and you start and then, like the world doesn't fall down and faint because it's so amazing, and then you have this, this moment, like nobody gives a shit.

00:40:35.047 --> 00:40:35.755
Why am I doing this?

00:40:35.755 --> 00:40:39.945
You know I have other stuff to do like, is this really what I want to do?

00:40:39.945 --> 00:40:43.880
And you have that dip and and every time you start something new.

00:40:43.880 --> 00:40:51.704
And again, I've been married for 29 years, so I don't have a perspective on online dating and whatever, but but I imagine it's.

00:40:51.945 --> 00:40:53.777
I think it's kind of the same in a relationship.

00:40:53.777 --> 00:41:05.597
You know you get excited and then it's doesn't quite live up to that and you have to go in knowing that that dip is going to come and sort of like knowing how you're going to handle it and how you're going to push through it.

00:41:05.597 --> 00:41:11.539
And then you know you get back into this kind of positive energy of whatever that thing is, that you're trying to build and create.

00:41:11.539 --> 00:41:19.288
But if you go in not expecting the dip thing is that you're trying to build and create, but if you go in not expecting the dip, then the dip is much more devastating when it comes.

00:41:19.288 --> 00:41:35.684
If you go in knowing like there's going to be a challenge here and that initial momentum and whatever is going to wear off and there's going to be a moment where I'm going to question this, go in expecting that You're much more prepared to kind of navigate it and just push through it and then like everything good happens on the other side of the dip, you know.

00:41:36.065 --> 00:41:36.847
But I think you're right.

00:41:36.847 --> 00:41:39.601
It's like how do you show up?

00:41:39.601 --> 00:41:41.206
Do you show up?

00:41:41.206 --> 00:41:43.380
Do you try that new thing?

00:41:43.380 --> 00:41:50.005
Just expect great things to happen, but when the hits come, don't take them so personally.

00:41:50.155 --> 00:41:57.922
I mean, you've said that it's not personal- I don't say this judgmentally, but like I don't know how you don't try the new thing, like I really don't.

00:41:58.422 --> 00:42:02.967
Again people wire differently and not everybody needs that energy in the same way, I guess whatever.

00:42:02.967 --> 00:42:03.487
And that's fine.

00:42:03.487 --> 00:42:09.735
But for me the thing I was always afraid of was people go like oh, you start a company, there's a lot of risk in that.

00:42:09.735 --> 00:42:10.677
Hell, yeah, there's a lot of risk in that.

00:42:10.677 --> 00:42:18.369
But I always was kind of worried about this other risk, which is like that I just squander my gifts by, you know, not taking those chances.

00:42:18.369 --> 00:42:20.840
And I guess there's a balance of those two perspectives.

00:42:20.840 --> 00:42:23.509
Right, because you don't want to just be a cowboy either.

00:42:23.509 --> 00:42:27.945
It'd be okay to be like a literal cowboy, but but not like a, you know, a reckless cowboy.

00:42:27.945 --> 00:42:31.358
But but for me that's always been a little bit.

00:42:31.900 --> 00:42:38.789
Again, just the way I've been wired is like if I have a thought and I really want to explore it, like I kind of think, shame on me if I don't.

00:42:38.789 --> 00:42:41.563
And in different moments in life it's harder to do.

00:42:41.563 --> 00:42:45.666
You have obligations and you have, of course, like you got to kind of take all that into account.

00:42:45.666 --> 00:43:00.085
You get that gift of inspiration, even if that is trying to write about it for half an hour every day or just trying to like do more research on it.

00:43:00.085 --> 00:43:09.545
It doesn't mean like, oh, I quit my job and I go, you know, organize my life around that new thing, but there's usually some way to kind of give over part of your energy to that thing.

00:43:10.146 --> 00:43:19.481
And what I've always found and I kind of realized this when I was about 20, is that there are some things in life that are really difficult but somehow they give you more energy than they require.

00:43:19.481 --> 00:43:31.844
Like for some people working out is that, you know, I think depending on your sort of spiritual or religious practice, you know that can be that that it's like it's hard to commit to but like it just gives me more energy.

00:43:31.844 --> 00:43:38.280
And I've always, ever since I, had that realization.

00:43:38.280 --> 00:43:41.775
I've always just wanted to find those things like this is hard, but somehow when I'm doing it I lose track of time and forget to eat lunch.

00:43:41.775 --> 00:43:43.458
Oh yeah, you should probably do more of that.

00:43:44.161 --> 00:43:44.824
That's so cool.

00:43:44.824 --> 00:43:50.367
Well, dave McLaughlin, you are a gift as a friend, a gift as a creative.

00:43:50.367 --> 00:43:54.405
This podcast, I feel like, is a gift and you have a gift for the listeners.

00:43:54.405 --> 00:43:58.360
So tell them what is in store for them for listening today.

00:43:59.101 --> 00:44:01.106
As we said, to join Cake you have to be invited.

00:44:01.106 --> 00:44:07.996
What we're going to do for all of the subscribers and listeners for this show is extend an invitation.

00:44:07.996 --> 00:44:23.981
So I think the easy way to do it send an email to love at cake members C-A-K-E-e-m-e-m-e-r-scom, and we'll we'll respond and make sure that you get invited that's amazing.

00:44:24.101 --> 00:44:24.923
I love this idea.

00:44:24.923 --> 00:44:33.936
This is going to be really fun to track and I'm so proud of you and I'm so excited to see what is to come with cake thanks for having me on.

00:44:33.976 --> 00:44:38.744
It's been fun and I'm inspired by everything that you've built, and it's just great to be in the conversation.

00:44:39.286 --> 00:44:39.947
Thanks, Dave.

00:44:45.036 --> 00:44:45.958
Hi, I'm Dave McLaughlin.

00:44:45.958 --> 00:44:46.900
I'm the founder of Cake.

00:44:46.900 --> 00:44:49.646
Cake is a whole new concept in shopping.

00:44:49.646 --> 00:44:56.922
It's an invitation-only membership community for women who love to discover and shop the most coveted brands in fashion and beauty.

00:44:56.922 --> 00:45:02.117
And we've got a special, exclusive opportunity for listeners of Shot at Love.

00:45:02.117 --> 00:45:14.896

A Journey Through Tech, Film, and Fashion with Cake's Founder Dave McLaughlin

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