Winning Your ‘Now or Never’ Moments
Deciding to decide for yourself, can be the most powerful lever to improve our happiness and our success. Donna Khalife should know.
For Donna Khalife, her life was a series of rational, deliberate decisions that led her to the top Business School and job offers in Wall Street and Silicon Valley. And she took “none of the above”, choosing a life following her passions that has led her to the hills of Hollywood, a top rated author and today a Shark Tank alum who’s company Surprise Ride has raised millions after first being passed over by the Sharks
So how do you decide?
Experts say our decision-making process as either rational or emotional — meaning we are carefully deliberate, or just act and go with our gut.
Learn how Donna decided to act ‘rationally emotional’ by choosing to create her own path that in hindsight isn’t all that risky or crazy — and how you can do the same. It’s a fascinating conversation showing the power of winning in the decision-making moment.
Listen to the Episodes below, or see the full transcript of our discussion below.
Part 1
Part 2
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Interview Transcript (apologies for any errors in the automatic transcription):
Donna Khalife: When I was six, we fled in the middle of the night and my parents like spent all their savings to buy tickets to get on this boat that was going to Cyprus really. And My, my entire extended family couldn’t afford it and stayed behind. And I remember fleeing in the middle of the night. And one of the reasons that this memory is so vivid to me is because, I think in our rush to get out, I ended up wearing my brother’s shirt tee shirt and it was a superman shirt and it had a big giant s on it, which was totally fine. And all, it was good except when we got on the boat, there’s no lights when you’re fleeing in the middle of the night and not, you’re not even allowed to light up a cigarette or like a lighter because enemy forces can like see that. And it’s bad news for everybody. So I happen to be wearing a glow in the dark and coming out of my shirt. And I just remember being very scared as a little girl and hugging my mom to sort of like hide, but I like target on my chest that feeling of like, oh my God, I’m going to be targeted.
Eric Koester: Hey everybody. It’s Eric. On today’s episode, we’re going to have Donna Khalif in this new studio and she is the ultimate creator. I think what’s amazing about her story is we’ll begin by talking about the family’s flight from Lebanon and sort of being afraid for your life and how that in some ways has started a very traditional career for her that she decided it wasn’t for her. We’ll hear about the moment that she made the career counselor at Harvard Business School, basically be speechless. And frankly I was speechless too. We’ll talk about the power of buying a one way ticket and ultimately how these sort of capturing these moments of time. Donna is an author who describes her experience as an investment banker in a way that still empowers others even though she’s long since gone from there. She’s had an incredibly interesting entrepreneurial career. And we’ll talk about how she sort of hatched the original business idea that, that eventually got her on shark tank and now has, has turned into a global business surprise ride, how she hatched it basically on a Google document that she was working on a seven hour time lapse increments with her sister Rosie, who is now her co founder.
Eric Koester: I think it’s interesting to see the story of Donna as she went from this very traditional investment banking, doing the right thing mindset to basically quitting going to become an actor or an actress in Hollywood, making her way through Hollywood, but ultimately deciding that for her entrepreneurship is the path and you’ll hear her stories about how she’s become such a great storyteller and, and, and how her adventures have been along the way. It was fun to have done it in the studio. I really, really enjoyed hearing her story and I think you will as well. All right.
Eric Koester: I’m stoked to have you here. Everyone, this is Donna Khalife and I pronounced that right just because you said it 30 seconds ago. although it’s butchering its original pronunciation as it may be
Donna Khalife: However you pronounce my name is cool, but it does have the word life in it.
Eric Koester: Ah, that’s good. I hadn’t known that before. My name is also notoriously difficult to pronounce. There’s like a Weirdo and an e and it’s different in German, so I always tell people I answer to anything with a c and, and whatever else is in the middle and I’m all good. All good. so we’ve, we’ve known each other for awhile now and I’m really excited to sort of. And it was fun like as I was sort of sharing some of the stuff I was doing, I was learning a bunch of things about you and I was like, oh my God, you’re like the perfect example of some of the things I’ve been finding with students in research. And so it’s fun. It’ll be fun to sort of chat today.
Donna Khalife: Super Fun. And I love what you’re working on. So interesting. And I didn’t even realize that I was kind of the epitome of the students that would be a good fit for what you’re working on this kind of interesting for both of us.
Eric Koester: Yeah, your trajectory it’s like the trajectory of most sort of successful people, entrepreneurial people is there’s this moment when you create something and that is the thing that teaches you and and it’s fun. So. Cool. Well, I wanted to start a little bit because I think that you were sharing with me when we, when we’re together for drinks a few weeks ago, just kind of like the adventure even to get to America because I think this is sort of an interesting story of how you even got here and the, the many bounces that you had to, to wind up getting it. But why don’t you just start and tell sort of.
Donna Khalife: Yeah, it is, it’s been an interesting journey. so I was originally born in Dubai and my parents were working there at the time and then, were from Lebanon. And so we moved back to Lebanon and it was during the civil war and that part of the world unfortunately has been in that war zone for a long time now for decades. and, and when I was six, we fled in the middle of the night. My parents spent all their savings to buy tickets to get on this boat that was going to Cyprus really. And My, my entire extended family couldn’t afford it and stayed behind. And I, remember fleeing in the middle of the night and one of the reasons that this memory is so vivid to me is because, I think in our rush to get out, I ended up wearing my brother’s shirt tee shirt and it was a superman shirt and it had a big giant s on it, which was totally fine and all was good except when we got on the boat. there’s no lights when you’re fleeing the middle of the night and you’re not even allowed to light up a cigarette or like a lighter because enemy forces can like see that. And it’s bad news for everybody. So I happened to be wearing a glow in the dark, coming out of my shirt and I just remember being very scared as a little girl and hugging my mom to sort of like hide the target on my chest, that feeling of like, Oh my God, I’m going to be targeted and, and that’s what stuck with me from that night.
Donna Khalife: And we went to Cypress and then slowly made our way to this part of the world. And actually the reason we ended up in the US. So we landed in Montreal, Canada. So I grew up there. So I speak French. Everyone always asks me where my accent. It’s a, it’s a, it’s a bunch of different places. but my mom years later won the green card lottery. It’s a real thing. Yeah, totally. We didn’t believe it. We got them in a envelope and we were like, this must be a scam. My mom won the green card lottery and was able to give it to the rest of the family and that’s how we moved to the United States. And now I’m a US citizen and proud to be one. And, so grateful to be here to think back to being six years old and in some ways, you know, having all these little things along the way that I’m sure at the time you probably were like, this just must be what it’s like to grow up, not realizing sort of this is super weird and super tough. And, and, it’s, it’s crazy to think. Yeah, I didn’t really have a, the realization that, that was kind of a unique experience until I was much older and also even more recently with everything happening in the world and pictures of kids fleeing on boats now. It’s sad to see that history repeats itself. and it, it’s made me aware of that, you know, growing up like sleeping on the ground floor because there could be bullets like coming through the window any minute was not normal.
Donna Khalife: Just something that we kind of, we, we, I grew up in what, we, we as a family called survival mode. And it’s something I’ve carried with me in any difficult time or chapter in my life that like, get into survival mode. Yeah, yeah. You can survive, I will survive this, figure this thing out. And it’s interesting. As an adult to reflect on all of that, did you, did you find that you sort of repressed some of those memories? Was it something that like, I mean, I’m guessing you’re sort of in survival mode all the way for a lot of your younger life? Like what was the point that sort of these started reflecting on like how crazy that was such an interesting question. I, I do think you, you repress them and I think it starts with parents repressing them. Be Honest. As a family, we were pressed them the moment when I started really tapping into it.
Donna Khalife: I will probably get to this, but I started the company with my sister Rosie. We landed on Shark tank and some of the questions from the producers were around like, what’s your story? And we talked about those things and started to kind of explore them. And when we watched the segment, I’m with my family life, they later said to me like, oh, there were tears. There was this sense of like, I can’t believe you talked about those things. There was embarrassment or shame from siblings and parents and we had this moment where we looked at each other as a family and we’re like, those things really have to make those up. They were just this acceptance. So I think it’s, I think the whole unit sort of operates under denial mode for a little while until you’re like, okay, now I think I’m safe and right to talk about.
Eric Koester: And it’s the it then as you wanted not to define you and as much as it influences you, you want to not to define you. And then it sort of, it doesn’t always define you, right? You, you as an entrepreneur. And I think there’s a lot of research that shows how many immigrants and children of immigrants become entrepreneurs. And because of that, there’s actually some interesting research that I’m, maybe not research but anecdotes. They Andreessen Horowitz, the venture capital firm talks about. And several of the partners say they looked for people to come from dysfunctional families or dysfunctional backgrounds. And the reason they found is that if you’re able to manage through chaos in the family unit, you’re much more likely to be able to manage through chaos in business life and in those things.
Donna Khalife: I think it totally sure,. You don’t want to label yourself, you don’t want to be like the war refugee, immigrant, etc. But, and I think this happens for a lot of people who are faced any significant obstacle in their childhoods and you’re seeing it now with the me too. Me too movement where women and men are coming out and saying like, this actually happened and it’s taking a lot of courage to do that. And so yeah, it’s an interesting process, But I think you can apply any lessons learned in surviving the local things to entrepreneurship.
Eric Koester: There may be glamour and glitz that people think, but it belies its sort of the iceberg beneath the surface is much bigger than the little bit above the surface. It looks so. So rosie, I’m so, so you’re, you’re, you know, when the green card lottery you’re in, in America. And, one of my students actually Is writing a book on the immigrant mindset and talking a little bit about what it’s like to be an immigrant and a sort of like the way that parents even sort of manage in some ways their children through education and choices they make. did you find yourself sort of feeling like, I’m thankful to be here. I’m going to follow the sort of standard path as, as you’re sort of growing up.
Donna Khalife: Oh, absolutely. I think, it’s funny because I’ve recently noticed how many of my close friends are either immigrants or sons and daughters of immigrants. it’s something I realized when I was in college. I looked around and I was like wait, surrounded by a bunch of sort of first generations and I’m technically zero generation. I was a kid when it came to this part of the world. And there’s tremendous from parents to kind of fit the mold of like dr. Lawyer joke running joke. When I went to college, I went in as an engineering major, biomedical engineering last university. I got a scholarship to do engineering. I got a lot of support, for that I was just loved math and I love numbers and I thought, well this would be a good place to use it because again, those were the three choices brought up with and when I made the switch to business and finance and they also studied international relations because I thought in awareness of what’s happening in the world was just clutch to being right. But I, but I really knew I was going to go into business. My dad took me aside senior year of college, right, like, you’re almost done to graduate. He took me aside and said, you sure you don’t want to switch back to engine?
Donna Khalife: No, it’s late. but it’s, I didn’t really have their support in that way. It was, I had to pave that way. Had to teach them that you could make a living and a career out of business. they saw business as like the thing you don’t learn when she wanted to like run a convenience store or something. You can just teach yourself a while to teach them that. Like there’s a place called wall street. Really, you have to learn the ways and you know, there’s a sort of advanced thinking that goes into all that.
Eric Koester: You shared something with me before, is that as much as you were sort of having the traditional business experience, you also sort of had a little creative flair and you are the sort of, you, you tapped that creative itch, you know, talk about your, sort of, your, your side hobby while you’re in college.
Donna Khalife: So I, when I was growing up, I always loved acting and theater and I did have a unique childhood in the sense that my dad was an artist. So although my parents had the immigrant mindset, I had a very unique immigrant upbringing. My dad was the starving artists. Like there’s really no other way to explain it. Yeah. He lived for his passion. It was in his blood. He had to create art. That’s how he expressed himself. And I grew up with my dad always saying there are those who make money in those who make history interesting by, for a guy who grew up in poverty in Lebanon and came to America, could a very smart man, could have done things differently. But, he really believed in making history. Right? And so that was always in the back of my mind, I think as a young girl.
Donna Khalife: And so I went to BU, I studied finance, then I went and I worked on wall street, very sort of like traditional, you know, career paTh. And then I went to business school at Harvard and I got my MBA You had, you had like the, I mean that’s basically the path, right, of anyone who’s in business, you know, like if you’re, if you’re not going to be a doctor or a lawyer or an engineer or even an immigrant path, it’s just she stressed as an immigrant. I was surrounded by people who grew up with parents telling them it must be going into banking.
Eric Koester: You’re at one of the most prestigious firms on wall street. I mean, you sort of have done all of those right things.
Donna Khalife: I did those.
Eric Koester: I know you and it was always funny because I know you and I, I, I don’t think of you as. I mean I know those people, right? Like who, who go that path. It’s hard for me to like think back of that because you do have this sort of creative flair and you said even while you were in college you were doing theater and things like that.
Donna Khalife: So those electives, I was like the non theater production, met some fantastic, amazing people that way. But when I went there, worked on wall street, I think it allowed me to stand out in some way. It allowed me to perform at a higher level because you’re being, you’re being modest here. I mean you were like great at your job, right? Like frank four years in a row because I started. so I not only that’s like, this is like the premier topic, like investment banking is like, this is like the cat’s meow of sort of the world of high finance and investment banking is for those who don’t know.
Donna Khalife: I mean, it’s basically like you’ll eat and you don’t sleep and you work, like that’s kind of it. It’s the printer you spend a lot of time at the printer, the printer and a lot of time doing all kinds of things. It runs the gamut and I, when I was going, so I got a job at jp morgan, which was tough, tougher and continues to be on the street. But then within that you get to choose your group, right? Are you going to focus on an industry or a certain product? And not surprisingly, I went for the toughest group, an acquisition, right? Remember someone saying like, that’s the toughest group data into some part of me was attracted to that. Right? I’ve, I’ve since learned to listen, but I also loved the concept of mergers and acquisitions. Like why do companies merge with companies that seemingly don’t relate?
Donna Khalife: And I remember thinking about just like pepsi buying a frito lay’s chips company, this is a long time ago, right? What are the synergies and wanting to learn about how you value a company. You know, how much a pair of pants, like how do you value a company? So it’s really interesting, but I did end up choosing a path within investment banking that was extremely difficult. I was surrounded by men probably. I don’t know if I ever worked with a single female. At least there’s a oftentimes as an entry level class where those, yeah, it’s fairly diverse gender wise, but it, it sort of even within my class. So, the year that I joined, there were eight of us that got selected to be in the room, how many slots they had and that was one the one girl out of the eight, so surrounded by seven guys who have become really good friends, but there’s a competitiveness at the star.
Donna Khalife: Right. It’s interesting. YeAh, it was really interesting and it was difficult because you didn’t really have mentors who were women to look up to when it turned to and it just, you have to be that much more, I think emotionally aware of, you know, I’d walk into a boardroom.
Donna Khalife: So the beauty of M&A work is that you get to work with ceos and boards as they make these really big decisions can affect your twenties and you’re dealing with a big deal. It’s crazy, right? You’re like, why did they let this person in the room? But that’s the world that is like there’s just sort of. Because you just have to have the highest, smartest people there. They burn them out oftentImes. But there are new operators in
Eric Koester: Two years at four. So it’s kind of like dog years. But you know, I think being a woman really helped me because I was able to connect with those ceos and those board members on the level that maybe some of my male counterparts didn’t.
Donna Khalife: So I think it’s always been interesting to be the only woman in the room. And even in entrepreneurship now to some extent, I’ve been in situations where I’m sitting there and I go, if this was a black and white image, someone just snap the photo and you would think it was 1950. I’ve been in those situations than in that row, which is crazy. It’s entrepreneurship is supposed to be at the forefront of innovation, but not that continues that bias because he did you think there’s an interesting thing that I oftentimes, I mean, I meet a lot of aspiring entrepreneurs, particularly those that are these transition points and they the brightest of the bright or oftentimes and consulting or banking, you know, like yourself. what’s interesting is there’s research now showing that some of those firms are actually really good. Jp morgan mckinzie, they’re actually really great at creating future founders.
Eric Koester: Did you recognize that the time that you were sort of, you were exercising the muscles that you now sort of use all the time today? Did it, was it clear to you that there was something happening there? It was completely unclear. I think you’re in survival mode, right? Going back to that theme, when you start in one of those traditional jobs, whether it’s banking or consulting or even just corporate America, right? law is a great example. you’re young, you’re, it’s your first job as cool. You’re just trying to blend in. Don’t notice how I say the, the, the grasp, the tallgrass gets chopped or something like that, like don’t stand out, just get out, just like, just like blend in, you know, provide the value that they expect of you and kind of cruise along, and, and just absorb all of that I learned.
Donna Khalife: And so I had no idea what skills I was getting. I just knew what had to be done. They put my head down and work really hard and I made sure to take breaks. I mean, I lived in New York city and one of the rest cities in the world to jumpstart your career. But I think it wAsn’t until years later that I realized, wow, the amount of responsibility I had as a 21, 22 year old is a very special. And that I think in some ways set me up for being an entrepreneur. As you know, as an entrepreneur, you’re reaching out to people you don’t think will reply, you know, and you’re trying to, put something out in the world that’s never been created. You know, it, it kinda mirrors thE amount of responsibility. I should not have this much with billion dollar companies as a young age.
Eric Koester: You will get to this a little bit. You, you eventually wrote a book on your experiences as a banker, but I wanted to kind of pull out a quote that I saw was really interesting and you know, you probably did at the time you really, you might not have known that going to be an entrepreneur, but. No, it’s funny that you say it. So you wrote, I’m banking is the bootcamp of jobs. It’s extremely challenging. Takes a lot of hard work, long hours and exposure. You learn working with top level business leaders and corporations can definitely opened the door to multiple careers outside of the bank. Now what’s interesting about that right is if, if you probably could take away the word banking and say entrepreneurship or whatever it may be, it’s fascinating to sort of think that there is a large number of sort of successful entrepreneurs who got their start in high level finance, investment banking, high level consulting, because I think of that, right?
Donna Khalife: You basically are thrown to the wolves and if you make it, there’s, you know, you can make it in anythinG. True. Yeah. You really do. You learn. it’s about learning quickly absorbing what’s happening around you, learning from the greats, learning from the people, the leaders. Am I going to do. I’m thinking quick on your feet, which is not a skill you learn in school. Really not have to learn outside of school and you have to put yourself in. Those situations don’t really happen on their own. You could be in another job where that’s not happening. I don’t, I don’t remember writing that. That’s. Yes. Yeah. No, I think it’s your words. You know, I, I remember now that you, I don’t, I don’t remember making that connection between investment banking and entrepreneurship at the time. Well, I think it’s one of the things is why I think it’s sort of, this is an interesting episode to have you on because I think there is this sense that people often feel like they’re selling out.
Eric Koester: If they take a traditional job and go into banking or consulting or law or finding whatever it may be, and I think what part of your story is interesting and we’ll get to some of the things that you, you’ve gotten to do since, but like this is, if you don’t have a company in mind, man, you learn a ton and get a ton of responsibility from best with banking. So it’s not like, oh my gosh, I’m, I’m, you know, this is terrible for me. I’m, I don’t have a startup idea. I should I. Why would I take this job on wall street? No wall street prepared you to be successful today. It absolutely does. And I have some words of advice for people who do go to those stats. So I, I’ve always said this. So since I’ve written the book has gone out and spoken to to various universities about this and I’m actually a believer in going with a traditional path.
Donna Khalife: It’s hard for me to say, to advise students to go entrepreneurship straight out of school. When I say to them, if 100 percent, no, this is what you want to do, by all means follow your heart rate or that, but if you’re at all unsure, I’m going the traditional path sets you off, but in a very nice way to have that optionality. However, those are also careers that really have been built over decades. Many decades of investment banking isn’t old street. so as law and consulting and all of these and is there incentive systems are such that it’s very hard to leave them. That’s right. So, right. So it wasn’t easy for me to walk away from them and I still get moments today where, you know, I still get moments where I’ll have old colleagues say, hey, look, come back.
Donna Khalife: With that comes a promise of, you know, high paychecks and all these seemingly great, you know, job situations. But so I walked away. I was six months away from another six figure bonus and I had to say no to that. No, I’m going to go, I, I, I know this is not the career path for me in the longterm. And then make that switch now. how did you decide the next step was business school, right? You went to business school. Did you do, were you looking at business school as a transition moment for you or how to like, so you weren’t thinking of it as like, I’m going to go the longterm and be this is my next level up at the bank. It’s sort of a new way to transition. Yeah. So I, even when I was applying to business schools, I had many meetings at the firm where they would sit me down and go, are you sure you want to go to business school?
Donna Khalife: So that was already in a post mba role. So there was no. Oh I see. Oh. So it wasn’t like this is like a, this is not a level four years and I’m already getting paid. Like hey, I’m literally training people coming out of harvard and wharton. Literally. I actually recruited at harvard at morgan and that’s partly why I wrote the book because I recruited at harvard business school and some of these other schools with my jp morgan hat on, like having your second career at, sent me down and go, are you sure you want to be going back to business school and what are you interested in? And I remember talking about micro finance, no really working in social entrepreneurship and I’m teaching people how to come out of poverty. And they’d say to me, well, well, we have a group that does that put you in a. And this was during the subprime mortgage crisis where they were laying people off. So friendliness, sit down with me and try to get me to say mental, right? so this is what I mean about anyone who does decide to go in traditional paths needs to sort of keep their heart in check because it’s quite easily caught up in the adult. So, but I decided to go to business school as what I called the reset button. It’s interesting. I always think of business school as a potentially a reset button.
Donna Khalife: It’s a way for you to take two years to re-explore what, what might be your purpose in life, what you do. That’s how I approached it. So I went there with an open heart, not sure where I was going to land, thinking navy was going to be micro finance in my business school interview. They said, where do you want to be? What would be your dream job? And I thought that’s what it was. I explored that too in my first and second year and I decided it wasn’t for me. So, if you like. So first off, generally getting into harvard sort of says you can write whatever ticket you want next.
Eric Koester: There’s not grades, right? Like it doesn’t get caught up in that. Yeah, right. Like whatever. Right. So you’re, you’re basically there and you sort of get to decide what’s next and you’re looking at as a reset button where you attempted to go back to wall street. Oh yeah. I had the same recruiters that I’ve worked with, you know, every, every, hey blonde while we’re here, why don’t we sit down with john again, take me out to dinner
Donna Khalife: time with friends and all that. But, I, I caught the entrepreneurial bug a little bit and I made it a point during my second year to take a lot of entrepreneurship classes. I thought what an amazing ability to start something from scratch and grow and get people jobs and products that they love. And so I applied to silicon valley jobs and I kept kind of finance as my backup number two or maybe something they would open up that was so interesting in the microfinance here or whatnot. And then, I was the career rep for my section, which means the whole thing. Yeah. In charge of helping people figure out where they want it. That’s how important it was for me to really call it my heart. I was going to be open all career paths. And so. And then I went to my career office.
Eric Koester: You told me the story. This is a by the way, but I just gotta set it up. This story. I’ve actually shared this story with other people after you sell it because it’s so. It’s amazing that the, it’s amazing story, but I’ll let you tell it and I just think it’s funny with the career office. Yeah, exactly. These are the things I’ve been though either
Donna Khalife: on their team that went out and spread the good word and help others, during the recruiting process. And I would do training classes, how to interview and resume cover letters and all that. So I knew the career office well and I went in and I sat down with the coaches and they said I am going to reject these job offers. I had jobs in silicon valley, New York finance and and actually in education because education was in an area that I was interested in, that I’ve always been interested in. And they said to me, and these are companies that were recruiting efforts, have they have relationships with them. And I said, I’m a, I want to go to hollywood and I want to do.
Eric Koester: And she looked at me, I wish you would have taken a picture of her face when you said that because it’s like so
Donna Khalife: much loss. Yeah. Excuse me. And then there was a moment of wow. So ken and I and I sat there and I said, is there anyone you could connect that could just like banking wall street or becoming an actor? This is what you guys do, right? It’s harvard and they have, you’re connected to a lot of different people. And I said that could maybe help me with this transition. She looked at me and she said, in all my years here at harvard, no one has ever rejected these job offers to go to hollywood, just like, are you sure you want to be doing this? and I think her heart was breaking into a. Because I knew these were really good job, offer lots of interviews and all that. and I was scared shitless, right. I am not confident in his decision making. My dad looks at me. I remember the moment when I said this parents probably my dad for probably a couple of months. We’ve kind of just walk and look in and shake his head, like eastern mustache, like powder. So it was, it was not easy for me to arrive at this decision, but I knew that if I went into any of these jobs
Eric Koester: I was not because I had the experience with it. I knew it was hard enough and I. Was there a moment that sort of.
Donna Khalife: There’s always sort of this glorification of the moment when you knew you had to do this, was there something that you remember to say like, this was the moment when I said I can’t do this. When I Said I can’t oR can’t, you can do this, you can do that. I’m not going to go. I’m not going to go the, I’m not going to do what I just did. I’m going to do this crazy thing of become an actress. There was a moment where I call a friend who was in hollywood, an old friend from, from undergrad who I’ve done shows with. She’d been out there since undergrad. And I remember getting on the phone with our late one night and saying, hey, I’m thinking of moving there. And she was just like, all optimism and excitement was contagious and I really think actors and artists have this amazing ability to be optimistic. And I think that kinda got me like, I can do this, do this. And how many, how many moments did you sort of sit there and say, maybe I’ve made a mistake. Oh, goodness. Unlimited. I mean, I almost, I feel like I almost broke every meaningful relationship in my life with my parents and my family. What are you doing? Eventually they got on board and my mom was more supportive, with my partner at the time.
Donna Khalife: Wait, are you sure you want to be a one way ticket to hollywood? And so many times all through me moving there, like the first three days I remember thinking I’m going to break this lease and I’m going to move back home and feeling that scared being so absolutely grateful. But I did it with someone when you first told the story. And I’ve always wanted to say I bought a one way ticket to blank and you know, and I think it was hollywood two suitcases packed, pack them up and he showed up to an apartment that I hadn’t seen the craigslist and booked. And it was, I called it camp hollywood right below the hollywood sign. Oh really? Yeah, it was, it was, it was like the basement of someone’s house. It’s right below the hollywood sign in the hills. And it was because I basically lived outside dirt would come in through the window spiders by the end of my time there.
Donna Khalife: I was like talking to spiders just called it camp hollywood, but a life changing experience that now that it’s been some time, did people say like we thought you would make it a week or like did you, what, what do people say now that you’ve sort of come and come out the other side and have this life you have today. What did they say? Yeah, I mean, I think thAt, so the fun thing was, it was interesting to see. And this is something good for entrepreneurs to know your family and your loved ones always react as if they’re under threat, you know, they always react as if our safety is at stake. Right. And your friends and maybe more distant friends will come from a place of being really inspired by doing. I had that happened and that just goes for in life for everything you do now or in any difficult choice to make.
Donna Khalife: So I had a whole group of friends kind of really live like to share their story. So I did that. I documented it a little bit and they shared it with them. and I stayed away from my family just a little bit and kind of share more of a positive. and eventually they were on board. That’s awesome. Like it always happens, right? Eventually they find, and breaking into hollywood is not easy for anyone, but you would have thought it was interesting when you were sharing your story about breaking in is that you approached it sort of less, almost like an actor per se, but more as like, I am in the business of me. And you know, it’s like, it’s interesting to think about that is like, okay, everyone’s like, why are you going to be an actor? And you’re like, no, I’m just playing what I learned in my prior life into this new world and almost you sort of whatever to navigate through it, you know, what may have taken other normal people a decade in like months, very, very much like a startup and coming out of business school or I had been so entrenched in startup mindset, it just thought of myself as the brand and in fact there was a one year reunion at harvard and they wanted to hear from entrepreneurs and I put my name in the hat and I was like me and and they were so happy to have the present at event.
Donna Khalife: But I, I really approached it that way. Again myself. A timeline, quarterly checking and how do you explore? It’s like product market fit. And so I approached it and I took classes and I applied and audition to things and product market fit was going to be whether I got some of those. So I really kind of interesting and then it had the budget initial budget to survive the year of the lot of these mac robin, but were there moments when you thought looking at it now that one thing breaks a different way that we can be talking to donna, the actress was there sort of like you’re attacking this as you know, you’re getting yourself in there in a different way. But again, someone probably might’ve looked at this as a 10 year thing. You said like, I got a year, I’ve got to figure that in. What was some of the interesting moments that were maybe one, one, one a eyelash away.
Eric Koester: Wow. I think that if I stayed longer, you might be talking to donna, the actor. I think there is. I think it is possible to apply the principles of business and entrepreneurship to an artistic career path and get their faster, get there better. I do believe that. I think that if I’d stayed in it, I could have. I decided that it wasn’t for me, for a number of reasons. it wasn’t the type of career that I wanted to pursue in terms of unpredictability and I come from such, but others can, I love that they can. but the moments that I think my quarterly checkins were very painful would check in and go, hey, what have I learned? What do I still want to do? And also how do I, what do I want to do that’s fun so that I can look back at this and go, well, I have one, right?
Donna Khalife: So I remember the moment where, I joined a sketch comedy troupe perform on hollywood boulevard at theater and sketch comedy and the format and really be part of a truth moment saturday live, right? Some of these people do go on saturday. but that was something that I felt was missing from my experience. Having those quarterly check ins were kind of, okay, where am I in three months? Flies by. It’s like a blink of an eye. That’s one thing I learned three months is short time and have those realizations like I want to. So one of the things I was interested in was hosting and so I said, okay, I want to take a class and explore what it’d be like, improv comedy needed more dramatic acting road, come out of the tiers, feel depleted because you just played the role of a young girl who had been abused. It was just like he really lived that experience. and so I think those check ins are important to make sure I was having the most varied experience and they’ll probably go to life than just fascinating. And I think the other thing that was used, used shared is you sort of had to figure out how to
Eric Koester: make money in various points and, and you know, as you said, at one point kind of the opportunity that we talked about earlier, your book came about as, you know, you didn’t as much pursuing as sort of a, hey I want to write a book, but like hey, this is a way to maybe make some coin. so how did that all come about? And
New Speaker: yeah, that’s interesting. So, so I, I absolutely, and I needed to figure out a way to make a living and cover my goal, but I, I got, I got an email from a new publisher, so a startup that was doing books that would respond to people’s searches in google, what were some searches that were maybe had an unmet need and they would reach out to people that could be experts. Friend of a friend somehow connected me to this publisher and never thought of writing book. It was really not in my plan and I was like, okay, this is maybe a way that I was going to get to make some loyalty. Yes. And also solidify this chapter in my life that was slowly changing. I’d given this verbal advice so many times that people would call me all the time. Can I get some recruiting advice seminar? Wouldn’t it be nice to spend that hour talking about dumb and their situation and just have them read book? We could really use that time and the more value added way. That’s really where I was like, sure.
Eric Koester: I also love that the, the, the donor hustler was like, were like, originally they wanted you to just write on jp morgan. You’re like, I’ll only do it if you lead me to whole
New Speaker: enchilada. So they me. And they were like, no, we really. One of the searches on google that goes on that is how do I get a job at jp morgan woUld be perfect for that. Yeah, we want you to write that book. And I remember hanging up and thinking about it and I didn’t. It wasn’t one of those questions where I didn’t really need anyone else’s advice. I’m not going to write the book about jp morgan because I knew that the industry was, the advice would be applicable to anyone. It says sets them, fell back on the phone and I was like, I’ll only do it if it’s about banking, but you could certainly run some ads on, you know, you could really make sure that book answers those people too. That’s fine. But there’s no reason.
Eric Koester: It’s interesting and I think you said something that I sort of struck me, which was sort of to document that phase in your life which was know 100 hour weeks hustling your way through it and, and that high level stuff and it was, the book was a lot of ways for you to document that one in and almost like cement your expertise as a like let me show you what I know as opposed to like you’d be defined by three years or four years of, of time somewhere. how have you seen, because since then, you know, the book is, you know, several years old now, how do people see you? Like some people, you know, you’re an entrepreneur now, but people still reach out to you. Okay.
New Speaker: Say, hey, I read the book and I’d love to talk to you. And it’s fascinating because yeah, I do have this other life now as an entrepreneur and in completely different. I think what’s interesting is a lot of these traditional careers, the advIce is timeless. I knew that when I was writing the book that although you could update some of it and I, and we did, we did a version two point, oh, totally do for version five, but the types of qualities that they look for in a candidate hasn’t changed the interview questions, the three financial statements and the things that solidified finance and accounting have a change and it goes to sacred law consulting and all these fields. so it’s, it’s interesting. But I, I knew that my memory was going,
Eric Koester: yeah, you don’t have the experiences like it’s not recent anymore. The story.
New Speaker: Exactly. And I think there are moments in life when all of us become experts at things, even if it’s a hobby you’re suddenly in love with, or maybe you become vegan and you’re suddenly obsessed with what that transition feels like and then 10 years later you’re going to be in time and you can’t really speak to that, but what would it be like to really document that and have that advice serve people for a long time.
Eric Koester: When you saId you even defined, that was sort of what your approach was with the living vicariously through you and la, so it’s sort of, it kind of sounds like it’s part of your, you know, your view these as chapters and you’re going to write the chapter as it’s sort of happening to make sure that you document that and maybe it’s to a little bit of your, your upbringing a little bit, sort of not losing sight of some of those intense important memories, that I think is forcing you to sort of document those experiences as you go.
New Speaker: I think it’s interesting too, we live in a time in the world where you can document right? It, you know, what, what did that entail? That entails me sitting in coffee shops typing away on the laptop. yeah. And another time that made it difficult typewriting. Yeah. I don’t even know what it looked like, you know, evolving. What writing a book would it look like? Right now we live at a time where
Eric Koester: you can grab your eyes talking about becoming vegan and what that process is documented. Why not. It’s kind of amazing to think that the, in some ways I would say because of the ease of doing it and I think that some tea that makes it even more scary, you don’t have the excuse of before was like, oh gosh, this was so hard to do, like I can’t do it, but but you’re right,
New Speaker: like all of these things are right at our fingertips. and we were almost living in a world now where there’s so much of it that you think, oh, I don’t have anything to add to the conversation. and I recently, I put myself through this filter several times where I go, but what’s my game? And I recently had this epiphany that was following. I follow several bloggers and I was following a blogger and I looked at her story and I realized that there’s nothing, there’s nothing. This would not have passed my test. I would’ve said, oh, well, not adding anything to the conversation, but every human being is unique. The way you share your story, specifics of your story. You’re not bringing all these things are you need. So I really think every single human being could add something to remember that it’s really important to know that it’s not as if you don’t have to convince everyone that you’re an expert or have credibility.
New Speaker: It’s just that a small communities is looking for you. One will listen and it will resonate, right? Whether they have the same exact chair experiences or just something about your voice, who you are, it’s clicking. And we Often forget that that happens. So everybody’s unique. Australian. Everyone contributed something. I, you and I have a shared experience of sort of both working in a law firm. You were in investment banking. And I think the other thing that I see is that people don’t always share this transition that they go through and, you know, none of them. I loved being in la and in london being in baking. And so it’s not as if like, I was like, oh gosh, I hate this. I got to go into entrepreneurship. I was loving what I was doing. I just knew this was the better thing for me is that one was bad.
New Speaker: Was it good? so I get a lot of questions the same way of like people, how do I become an entrepreneur and make useful piece of advice is be really great at your job, love it, and then find something that will, will get you there. And I remember having a moment banking where I thought if I put in this many hours and this much love something that’s my own, wouldn’t that be cool right here? I was getting some fraction. What from was not really about control any of it, but it can add value. They really hone in on what they’re good at and that’s like the perfect tea up there. so. So, tell me about this decision to start a business with your sister and it’s, it’s been fascinating to observe and watch and the trials and tribulations of entrepreneurship, but I just, I want to hear this story about how you decided to start this and then we can take a little bit through some of the venture sInce part of the ways.
New Speaker: In many ways I. So I was in los angeles doing the hollywood thing, really enjoying it. And I knew that this, it’s funny because I think that was always there to transition to new talent partnership, the way to go, we, you were an entrepreneurial ways, but it was like going from left brain, right finance to dabbling in creativity and like improv and sketch comedy is this unfiltered medium where you really have to just let yourself go. And then transitioning. And so I knew coming out of that year that I wanted to pursue acting in some shape or form on the side, but I really wanted to start a company and something that had some bigger impact. Some me. So back to the making history. It’s funny, it’s a statement that I think about all the time. Even now it’s very easy to lose sight of them, a returning money to investors and exiting and all these things.
New Speaker: And you forget why did I do this? So I knew I wanted to start something meaningful. And I started exploring ideas, with my sister who was halfway across the world. She was, she was in london at the time studying abroad as part of her undergrad. And then in Lebanon, at the american university there I’m also taking courses and we started this google doc where we would just, I would write ideas and she would wake up and there’s this the seven hour time since she would write these, that I would wake up when she was a. And I think that. So we zoned in on this one idea which was a giving kids a creative outlet like what we grew up with and we’d watched her nephews kind of glued to the ipad and both parents working full time and really empathizing with the plight of a parent who wants to give their kids those activities for this busy.
New Speaker: So we came up with this idea of shipping something to them on a regular basis that would give them that outlet and everything they need arriving at their doorstep. A subscription based activities for kids. And you’re both across the world. We’re brainstorming this seven hour labs. She’s. She’s literally has. no she’s not. I mean she’s a student, she’s not starting something and I’m thinking I’m going to start something. And then we just. We became so passionate about some of the google doc got to 30 pages, 40 pages plus from this one idea. We had a bunch of other ones. It’s kind of funny to think back at memorial, one of them was I’m bringing, bringing left knee, which is a strange yogurt from Lebanon to american and now it’s like you can buy a bunch of places. But and this idea really spoke to us and I think from that passion we thought, well, what if we learned to code a bit, throw up a website and let’s see.
New Speaker: We were very mvp startup mindset. Let’s see if anybody will put in their credit card. And that’s kind of how were you both living in the same place? Or was this all you were doing? this entirely remote at that point were still separated. funny enough, someone. So we did this and we put the site live and we learned how to do shopping cart, a merchant bank to accept credit card. All these things. We taught ourselves this. And we put the website live and an hour later we got an order. We hadn’t told anybody and we got an order and it was for a little boy named aiden and I remember writing this person and saying like, how did you hear him? Because I didn’t under. I thought it was, she thought it was a bug. She thought something wrong. The theme where, my, my cofounder and sIster things, donna, what did you, what did you do right?
New Speaker: What did you do? And, and this woman, the cool wrote us back and said, I saw on one of our, we had started an angel list profile. We did. We bought all the profiles on every spelling of the big dreams and she said, I saw this and I just signed it and we didn’t tell her that she has had gone live for an hour. But we were like, wonderful. We will have the product here shortly. And we’re like, look at each other. And we’re like, we have to create a product. That’s amazing. Have you met her? Ever since? We stayed in touch with, has been wIth us and she actually didn’t even know that she lives the first customer really. And four years later we said to her, did you know that idea? It turns out that also, we had so many things came out of this project that we didn’t expect. There were kids who had, you know, speech therapy, difficulties, who used our activities as a way to connect with their parents. We had kids who had disabilities who this was the thing that they look forward. And so we learned a lot talkIng to our customers that we didn’t set out to do.
Eric Koester: I love one of the things I’d love for you then to talk a little bit about the sort of, you know, your, your, your, you did make it to a television show, a not as an actress, but as an entrepreneur part of it. I think that’s interesting. It’s just me processing it is. I think one of the things that, that experience sounds like when you were in la taught you, is to be a better storyteller, to be able to sort of position yourself because you know, sort of shark tank which will spoil the lead you dId already earlier. So I’m not spoiling lead, but shark tank, it is really, it’s basically theater. I’m wrapped his entrepreneurship. And so talk about that, how that all came to be and in some ways how you crafted a story that sort of caught the attention and sort of took off. Like,
New Speaker: so when I was in hollywood, one of the things I learned is, you need everybody needs a hug and writing the book was really my focus was so that I could be known as the author and that was my, you know, that was the way that I approached people. And one of the things I also learned in hollywood is you can’t really make it there anymore if you don’t have a following. That’s fascinating. but we’re living in a world where you’re going to be put on a show or as a host. You have to already have some really interesting stuff to anybody who wants to do anything today. having a platform, having a following, having a voice is a big ticket. Attention. Someone told me to attention is the new currency today and you look at all these shows like the voice and so you think you can ask all of these where there’s judges.
New Speaker: A lot of times those judges are celebrities off, daddy has a new p, p diddy has a new show and these are the networks want the celebrities because that’s what’s going to draw people in for justice that you didn’t know, but they were expert it, you know, so, so having, but they also still interesting in those shows. They still want fan of voting to sort of determine who goes next to the celebrities help. But they still wanted to see who has the most audIence. And, and it’s interesting. It’s all about that. It’s about the attention. Yeah. and so I, you know, when I was writing the book to, I made sure that we would get like amazon reviews all these things to kind of bring it together. But when we, when we launched surprise ride at the beginning, like we had no clue how we were going to get people.
New Speaker: So I started to apply some of those things in entrepreneurship and one of the things was networking, like keeping your network up to date on what you were doing, right? So I remember sending an email to all friends and family at the beginning and saying, hey, I left la. Here’s what, here’s how that went, and it was really wonderful and now I started this company and here’s what it is and I’d love to have you sign up a kid in your life. And so that’s how we got our first 50 customers, really was just friends and family. Then I worked there. So I think a lot of the things I’ve learned in hollywood to life in a way, putting yourself out there not being afraid of rejection. Yep. Angel list profile without having any product yet. Not taking things personally because you go into an audition in hollywood and they’ll sit back and go, oh, I don’t know if I want someone with those features.
New Speaker: I had someone with that talking about it. You could do the randomness thing. How do you walk away from that experience and not feel crushed? Well, it’s not your performance or your talent, it’s just that you don’t fit this role. It may fit another row. Perfect. So a lot of those experiences ended up being very useful and I think spared me a good amount of heartache. And how did the, how did the connection to sort of the show even happened? What was the sort of the advantage? So we, when we first launched, we launched out of an accent, so we signed up for an accelerator program that was out of the boston area called beta spring and I actually flew out there and spent four months out. They’re based in dc, but I went out. Oh, did you really hit this? Yeah, I’m really took the leap and rosy at the time was finishing up school.
New Speaker: She got a four point. Oh really has it? I think when you’re doing things you love, somehow it goes into everything we’re working on. but they taught us that every you are to come up with 15 ways that you’re going to market your startup and you write it on a whiteboard and 15 ways every morning sounds like a, you start getting desperate and start writing things like walk to the corner store and just start writing, writing things and everyone would always tell us you should go on shark tank. And so, we always a smile, but I heard that the producers were looking for tech companies at the time and so we got the producers email address and I wrote him and I said, we’re huge fans of the show and one of the reasons we love it is because the products are so innovative.
New Speaker: And the other one is the story’s so interesting and here’s our product and here’s our story. That’s interesting. Threw that up on the dark. Like I was like, you know, 15 things. So she, you knew the story mattered because of sort of your experience in la, right? Yeah, it did. The story, the story. I knew that, it’s not just some television, but we live in a world where storytelling is and that’s what makes, that’s the joy of life. And so I didn’t expect a reply within five minutes. He wrote back and can you hop on a call? Wow, that’s kinda cool. So I hopped on a call and they still had no idea this anywhere, other 14 things on the list yet to cross off that day. Like I got things. and I hopped on the call with them and they told him a little bit more and he said, great, this sounds cool.
New Speaker: I don’t know if she’ll go anywhere. I don’t know if the, you know, the exact set at the network will be into it or it sounds really interesting. Can you send me a video answering these questions? And so I think we were going through the audition process and this is what you go through when you’re casting and at the time it was a holiday weekend and rosie was on the cruise. I was like, how am I going to do this? The second she landed back, I just grabbed her and I was like, we’re auditioning for shark tank with film, a video, we have 24 hours. I line up videographer atlanta and we’re going to do this. And she was like, okay, all right. Yeah. And so, people were very generous with their time and helped us out and that’s the community aspect. Ask for help.
New Speaker: And I’m very grateful for that, for them, for doing that really pro bono them, we didn’t have any money, had no money like when you good. And I remember asking him like we’ll call it, he does the video and he was like, well, for a company like you would expect it to be, you know, pretty nice. And I was like, I’ve learned not finish if you always just say yes. So we did that through the whole shark tank process. There were definitely many times where they’d be like, are you going to be able to get clearance to show this, to get this thing on tv? That is someone else’s creation because our kids are made of other things, right? and we’d always be like, oh, of course you have to call like the inventor of something popular. And so, that’s how we got on the show.
New Speaker: It was just, I think trying like, it’s like the simple stuff, right? Ask you never know. And then saying yes and really being showing up when we first, when we were going on shark tank or boxes were playing cardboard boxes with a sticker on your flat out. Kids didn’t care. They would, you’re on national tv, you know, so they, they, we’ll film and sometimes not eric, not really equality. And so we knew we had some that have nice boxes. He designed the boxes that you see today, blue and orange bowl and we got a batch of 20 shit ton of money. Right. That’s what you got to eat. No. The funny thing, so someone wants to describe, they said that they failed on shark tank because you didn’t get investment, but that really all along was not the point. The point is, was entirely as you said, attention.
New Speaker: And so like, how did, how did you think about that as you were like, you sort of, you winning is basically just making the broadcast look alive. Our goal was, was actually to just get them the says to get some feedback on our product, right from people who were brought to market my products like lori and kevin o’leary, who’s in our space education. So this company, and to tell a, I mean damon ended, go through the list. These are like brand exper. Mark cuban is brilliant in so many ways and robert’s software guy, we kind of went in wanting to get feedback on the product and knowing that it would be itching to a national audience. It’s really nerve wracking. And when you go on the show, you’re standing there and then all of a sudden they’re like a whole day there for a couple of days.
New Speaker: and all of a sudden it’s, you know, their county of the countdown, the doors open and you go down and you say your pitch and they don’t cut and edit into that. So if you mess up your one, two minute pitch, that’s it. So some people were in there for three minutes because they’re asking questions to conversion rate on your site, optimized things. That’s been. How old were you? How old is the company at this point? At this point comes three months, took my child crunched up. Why am I on this planet? It’s not a real business yet. It’s still early concept phase. I mean other people have been doing this for decades and here’s you a three month old company. So horrible. It’s really just to get feedback on product and have them fall in love with it and share that passion and they all did and of course to get investment because we didn’t really have any time and we got an offer from robert didn’t accepted fast enough, very dramatic. And Interestingly enough it made for a really interesting story, a good story. And I think people really enjoyed watching.
Eric Koester: Did you do that? I mean maybe it’s who knows, but just your improv training help you sort of feel like that being in that moment. Like you were able to manage through it. Because I’ve watched it and it’s, it’s, you know, you, you seem at ease, although it’s sort of dramatic in the way that it’s done.
New Speaker: Super nerve wracking. and then they have to edit it down a team all the time now in probably have, I have a book that’s about how to use them for other settings and I’m a big fan of if you’re looking for hobby or you want to do something outside.
Eric Koester: I’ve, one of my authors, jimmy is we’re writing a book called the farce of the sale on how improv can help with selling. And it’s interesting to hear him. I didn’t think about it, but he was saying like, it’s just how you interact with humans.
New Speaker: So yeah, I was just going to say it’s not just the relationships, it’s about kind of having that awareness to tap into listening to paul, what are you feeling and then reacting. So and when you don’t know this, but when you’re standing there, they’re all asking firing questions at you at the same time. So it looks very kind of q and a, but in the moment or like, do I answer this question or that? so I think improv definitely helped. They did some whAt felt like case questions. I felt like I was some of this didn’t make it on, but laurie asked me a question like, if you had 100,000 orders and how much would you have in inventory and I’ll let you know. We both stood there kind of like this is great and it’s like slowing down that moment, taking that deep breath, slow in that moment. So it’s maybe a minute or 30 seconds long, but it feels like and really responding from a place of calm. And I remember we responded and then kevin was a great answer. So, and so they moved on from that. So
Eric Koester: done. So yeah, I think improv simple.
New Speaker: It’s funny because my time in la absolutely hope that whole experience just being comfortable and I always looked at my sister and cofounder rosie with such awe and amazement that she really was able to also show up and carry herself so beautifully without that training. So, I mean, I think some people, either have it or it’s, it’s, it’s that you feed off each other’s energy.
Eric Koester: Right? Right. Yeah. I mean, I think it’s just fascinating to sort of think about how those elements define you and teach you in those different, different ways. I think it’s both. It is interesting to see people oftentimes think of entrepreneurship as the glamorous likes tech entrepreneurship, starting a startup quote, un quote, but you starteD a business as an actress. You started the business as an author and I’m, and this is where the natural outcropping of of that you learned all those things, but yeah, exactly. Just still,
New Speaker: it’s still the same. And how do you think about this? You some ways get defined by these elements and those ones and and even, you know, you’re defined by the story that’s put out there about surprise, right? As a tv thing. And now you have, you know, you think of this as, you go back to your original pitch is we want to inspire more children. And so there’s a big story behind surprise ride. How do you think about layering in those elements that those elements of creation that define you to not let it sort of stop you from evolving as as you need to go? Oh, it’s a tough one. I mean, I think when you’re a the public and the press will just latch onto whatever is interesting and it’s really up to us as founders to keep weaving in things that matter, to stay authentic brand.
New Speaker: it is really just. It’s such an important practice and if you can really hone that skill of being authentic and not being filtered and listening and all these things like being filmed for a national tv show or doing a press interview or so much easier by talking to your team members matter. You don’t have to pretend to think, what did I tell this other person? What’s going to sound like? So to say as a manager to get them to the right goal and let me just tell them how I feel. It’s disappointing. What’s exciting? Give them the benefit of the doubt they’ll make of that what’s needed. So I think We just make sure to stay authentIc to ourselves and all of these settings to make sure that the surprise right story evolves as it was intended have, but it’s hard because also I think, you know, we’ve talked about, getting kids to put down gadgets and then we often ask ourselves, well, what are we doing right?
New Speaker: It’s what are we doing to instill in our team the value of putting down gadgets breaks. And so we really spent the last year doing a lot of mindfulness work because as founders, you’re plugged into your phone, you’re managing so many things that customers, investors. so that’s been interesting to kind of come full circle and go, hey, what about us? Where do we fIt in here? Right? we don’t, we don’t oftentimes think about it. And I think you, you’ve talked about there’s these natural points in your life when you sort of said like, you hit the reset button. And in some ways, and I think even as entrepreneurs we don’t do that a lot because we’re sort of in survival mode all the time. It’s sort of this reoccurring thing that you have this skill of being in survival mode, but then sometimes means like are you surviving for the right way or the right thing and it’s particularly in businesses and I think yours, yours is no different that there’s this sense of like, all right, I need to like pause and I remember that was one of the biggest mistakes that we made was not like pushing pause.
New Speaker: We’ve raised 15 million bucks and we didn’t pause and say like, all right, now what do we do this for? Did we come in? What were doing? Which is wrong. I’ve made that mistake so many times. It’s funny that you said pause because I was literally thinking of that was just a few moments ago. I think it’s such a powerful concept and for anyone listening it may seem kind of cliche or something you would glance over was this boss, but it’s really about just taking moments either in your day or in your life, really honoring them and just taking breaks. I think it’s so easy to think, I can’t afford 10 minutes right now. Such a busy day of so many things to get done. I can’t afford a pretend everybody can afford five or 10 minutes. Really. I mean, unless you’re operating, you can take five or 10 minutes to just breathe and check in with yourself.
New Speaker: And it’s amazing what those moments are very powerful. and I love the movement, you know, area and huffington is leading this movement towards, you know, with her business to pausing or there’s a number of people really trying to encourage this. But I, I, we’re doing with our team. So we lead every team meeting every week with a meditation. Oh really? Interesting. And it’s been wonderful to keep giving our team the permission to do that for other day. And for them to have a nIce big space for them to do that. But giving them that permission because I think team members often feel like they must be going. That’s what looks good. They should be doing as leaders to say to them, hey, we want you to take those pauses are very valuable. So that’s been a really nice, simple way in the company to embody pausing.
Eric Koester: So what’s it been like now you’re, you know, you’re, you’re soonish, you’ll be your 10 year reunion for harvard business school graduation. What’s it like to reflect back with some of your classmates on, you know, their journey versus yours and you, what, what’s, what’s something interesting conversations you have now looking at this woman who says, I’m turning that all these jobs to become an actress and now has sort of come come as an entrepreneur and has interesting stories to it?
New Speaker: That’s a tough question. I think that they come to expect of me a little bit of wackiness yeah. As soon as I left there and went and did something and it’s fine because I had a number of classmates who came up to me and said to do that to me is interesting this year. One of them who’s actually running for congress now. Yeah. So it’s funny to see though where everyone’s heartless and how they listen to all that. But I think they’ve come to expect them to be somebody who maybe is a bit of a rebel, afraid to explore where they were. but the next thing is, I think that I feel so grateful that I shouldn’t go back to that reunion and say I’ve had. It took me a while to get to a place where I felt really appreciative for all of it because while I was living through entrepreneurship can feel like you’ve been through, really thrown into the laundry and you’re just on repeat.
Eric Koester: People say it’s the loneliest job is because the public perception of what people see, they see you’ve been on shark tank, you must be a millionaire and you’re like, you have no idea. Like I literally am like hustling my face off to do everything. and like you said, that you’re fulfIlling orders and you’re doing these things. And I think that the, there, it’s great that there’s a glorification of it, but it’s probably less different than being a starving actor in la or actress in la than it is being an entrepreneur is. It’s the same principles of being lean, being scrappy, being thoughtful, having to do it all for yourself and try to compete. You’re competing. It’s gigantic. Huge companies with huge budgets, television ads. And so you are,
New Speaker: the scrappiness is really powerful and you’re creating these things, we call them our babies, you’re inventing and creating these products and services and you’re really putting yourself out and be judged. Yeah, you’re putting a lot of love into them and you know, you’re expecting a lot in return people to pay for them to tell their friends about it. But, I’ve had many moments of tremendous lovingness as an entrepreneur and sets of depression called you kicking me and you know, you’ve been such a great source of optimism and energy and this is how it is. We got to keep each other seeing how it is. You’re not having a unique experience that I think it’s helpful to hear that from the trailer. As founders. does It remind you of some of those moments of sort of same sort of depression, loneliness when you were an actress?
New Speaker: Yeah. One hundred percent and a in there. I think, they allow artists to allow themselves to be more emotional. It’s interesting. I’ve had fellow actors like fry, dish and connection and I think as entrepreneurs and as business people really, I saw this in business, in the harbor. It was hard to share the difficulties, you know, when I started there, my mom was actually a diagnosed breast cancer or my school and I spent a lot of my first year going into treatments with her boss, such a blessing arbor one of the top cancer institutes. And I remember having not being able to open up about it, the business world, but these type a personalities not being able to open up about the experience and having a friend say, hey, you spent a lot of time with your mom. Right? Then realizing like she doesn’t know what’s happening. My mom won’t be here, but I think it’s important to keep reminding ourselves to talk about these things. It’s an invitation for people to really talk when things are tough.
Eric Koester: It’s a good reminder. I think I, I find myself too. It’s sort of, no one wants to be burdened with these things. but I think the broader point of all of this is it is this sort of mindset of putting yourself out there and we oftentimes forget that when you take a risk, other people do live vicariously through you and sharing those things can endear you more than anything. And I think it’s why you and rosie are such good storytellers. Generally the public face I got, you know, you are the brand that you’re embodied. but we oftentimes don’t take time for ourselves to sort of share this is what we’re.
New Speaker: And also I think we get so attached to the outcome of this startup has to result in x, y, z. and I think it’s important to remember that there’s a larger plan for all of us. Right? That’s right. Yeah. And I think ever since I’ve really been grounded in that, that kind of comfort. Yeah, good reminder. Especially for students who are starting out whenever they’re trying to create, sort of like what’s my next career move obsession with them. That was good career. But remembering that, you know, I started as a banker, a lawyer and
Eric Koester: sure we are still figuring out. Right, exactly. Yeah. This will be just be phases and I think you’re, I think what I like is your, one of the thing that’s consistent about you and I think other people can learn from is you are documenting those and whatever the right medium is at the time that we even talked about, like, you know, is now the right time to do a video series or podcast, whatever. I think that’s an interesting insight that sometimes people think they need to create something that’s magic. And what you were saying Is like I tell people about my experiences when I’m in la in la being an actress or I document experience as an investment banker and I share that or I tell my experiences as an entrepreneur. It’s an interesting insight that creating something of value that creates your own credibility could just be sharing your experience.
New Speaker: And every one of us has to. Every single human being that may resonate. Yeah.
Eric Koester: That’s interesting. What’s the, what’s so one more question and then we’ll talk. I have a quick like fast one for you, a couple of fast ones for you. What’s it like, you know, you started a company for kids and at the time that you don’t have kids, so now you have a daughter who’s as cute as hell and what is, what’s it like, what’s changed about your approach both as an entrepreneur and also as an entrepreneur for a kid’s? how have you seen yourself evolve as an entrepreneur, as a parent? but also then as as a customer now of your potential products or eventually
Donna Khalife: it was really fun because when we started the company we were on, that was really what was driving us. We were just, you know, young people who realized that kids these days growing up differently, I actually really, I wish more people got into some of these industries that they may not fit into the perspective you bring. and we had more time on her hands than a mom so that a parent was. So that was really neat. As as a mom now I feel really, I feel the pain that we’re solving. I have an 18 month old and there are times, even with 18 month old that I feel like, how do I raise this little girl to not grow up in a super hyper connect technology addicted world when toddlers, 80 percent of toddlers, two to three year olds know how to use this one and it’s, it’s actually hired.
New Speaker: and you know, the american pediatric association recommends that they only use face time, 30 minutes communicate with family and we’re all other things that. And I also feel the pain of spend my time a few hours so we can only read books so many times, play with blocks so many times. And so how do we, how do we as a company provide products for parents to help make those moments, we call them moments of love Is, are these really precious moments as, as, as family. How do we facilitate those moments for them, make them seem less so. It’s a, it’s definitely given me a firsthand perspective. but I, I think that overall working in the kids space. Yeah, that’s true. We’re just all kids at heart.
Eric Koester: It’s neat to see. I didn’t get it will be, it’s going to be fun to see as the evolutions in every business and I think as you go through the next phases of surprise, right? I think it’ll be interesting to see how she colors from your experience with her and I think it’s good that the problem that you thought that was out there, you validated it with, with, your own child and now it’s sort of like, all right, now as we sort of think about the next phase, what do we, what do we, how do we maintain that deep empathy with others and ourselves to, to iterate fast.
Donna Khalife: Remind me how unpredictable you put somebody out there for a minute or you put something out there that you think is cool and they play with it for the next five years. It’s really also allowed me to remember that when we’re designing and developing products, it’s really about shipping and putting it out there and seeing what the reaction is and not sitting on it. Kids are just so unpredictable. We had a
Eric Koester: so, so quinn our three year old who had her first sort of real understanding of santa this year. We were kind of like, like, we’re going do understand that I guess we’ll do santa, so we give these, like we gave a few small gifts like books and stuff like that and we were over at a friend’s house and to your unpredictability point someone said, what was the, what was the best thing you got? And we were trying to like scramble. We had like a stocking were like, oh, she puts some things in there. So we like literally grabbed a few dumdums and threw them in there and sort of said like, oh, like we put something in the stocking. She, without prompting, she said the Best thing santa brought me was lollIpops. But I was like, we brought you all these other thIngs and like the only thing you want is lolly pops, like, what are you?
Eric Koester: So yeah, you just, you can’t predict them. You can’t predict them. That’s right. That’s right. I love it. Well, this has been so fun and it’s been, like I said, we’ve sort of been learning these pieces and researching and chatting with you, so it’s really fun to to. I think the big takeaway that I would just sort of to summarize these things is that we don’t have to sort of be picking our forever anything. It’s always elements, but I think the important part that you laid out a that we sort of unpack today a little bit is when you make a change, spending the time in the moment sort of document that and not lose sight of it is is an important piece because I think you will always be known as an author who’s an expert in investment banking probably for forever and you will always be known as an expert in sort of what it’s like to be in business school and what it’s like to be an actress and what it’s like to be an entrepreneur and even as you have other chapters that sort of taking a moment and reflecting. I think there is. Every one of us has a story and by sharing that story is pretty powerful and we have somewhat of an obligation to document those moments for others. When you’re in it, you know, and learn so Much.
Eric Koester: Eventually you lose. All right. So sharing that with, you know, the younger generation or olDer generations, it doesn’t matter, but how can you share some of that and inspire someone else in one direction? Amazing. Well this was so much fun. I, there’s like a bazillion things in here. I’m trying to, like, I always write sort of these episode notes and I’m like, man, there’s going to be like, it’s gonna be like pages to write. So this is super fun. yeah. And thank you so much for, for this. And everyone that do check out donna, she’s an amazing human and I think the company is one that is is, is just a fascinating story and I think it’s a fascinating mission at the core of this [inaudible] dot com. And and I think I’m, I’m anxious for how old she does. Quinn need to be before. She’s really like a good, good fit for me, so at fritos and choking hazard, but she’s. Yeah, she’s three. She just turned three a few months ago. Start doing the activities now to help her out. I’m in. All right. This is good. Now. I’ve been. I’ve been waiting. I’ve been waiting and now that I’m in I’m going to do it. So now quentin, I can have activities together. Awesome. Down donna. Thank you so much. Surprise, right and awesome.
