Launching a Startup at 15, Creating Your Own Luck & Achieving the Life You Actually Want with Catherine Connelly, Author of Designing Success

catherine-connelly_3_10-08-2024_101019: and then we were eventually acquired in 2020 to the parent company, of eHarmony in a 500 million deal. And so that brought us back private.

And so I left in 2023. people that were there for very long time, we had fantastic retention, especially compared to tech industry. And I think part of it was people were respected and everyone had this Curiosity, wanting to learn, wanting to be on the working on the next cutting edge things.

And so I think that's why we kind of grew together. And so all through all these different phases of the company, we had our team to really rely on and really, be supported by.

Hello, marginal listeners. I'm so glad. Have you back with us this week? I hope everyone's taking care of themselves this week. And if you're really looking for an inspiring conversation full of heart. Part, we have the episode for you this week. I sit down with. Catherine Connelly, my trip. To her office is at 25 was one of my first business trips ever. And the kindness and authenticity she met me with then is still absolutely. True to this day as is evidenced by our [00:01:00] conversation. Catherine is incredibly decorated.

She co-founded my. Yearbook at the age of 15 and grew it to become the meat group and NASDAQ. As Dak listed dating in live streaming company. In our episode, Catherine talks about launching her startup in high school. Cool. And the challenges of entering the public sector at such a young age, She speaks to the many evolutions of my yearbook. Your book leading up to a $500 million sale in 2020 and. How throughout it all people always remained core to our company's success.

We also cover themes from her brand new book, including. How kindness has a way of coming back around and how accessibility for one. Group actually doesn't mean sacrifice for another

If you're interested in designing a life, you actually. I actually want, give this episode a listen and then be sure to pick up Catherine's new book. Designing success lessons from 20 years as a female tech entrepreneur, The book is available in paperback this week. And you can find. Online, anywhere you buy books. So with that, let's get into it.

abby_3_10-08-2024_101019: it's so good to be here with you today.

catherine-connelly_3_10-08-2024_101019: Great to be here with you too. Thanks for having me, Abby.

abby_3_10-08-2024_101019: Of course. This is very [00:02:00] bizarre because we actually go pretty far back, not to date ourselves, but I, I always like to talk about when I first meet people and with you, it's a particularly special story because I think I was maybe 25 years old and I was working at one of my first ad tech jobs. Startups. And it's funny because at the time I was taking business trips, but the majority of my business trips were to Israel of all places. I didn't take a lot of domestic business trips. And at the time you were, I think at that time your company had been part, had been integrated into the meet group. you were in Pennsylvania and you were a client

and I set out to go on a business trip to meet you in person. And it was a very big deal for me because I believe that was the first time I was on a train. Again, I had flown cross country. I don't know that I had been on a train, so the

catherine-connelly_3_10-08-2024_101019: Okay.

abby_3_10-08-2024_101019: here doesn't really

catherine-connelly_3_10-08-2024_101019: And to clarify, like New Hope, Pennsylvania was where the [00:03:00] company was located. So, you know, you're coming from, you know, West Coast, we're not in New York. If you fly into New York or Newark or Philly, either way, you're getting on a train. The train's like an hour. and then the office was like, at least 30 minutes Oh,

abby_3_10-08-2024_101019: Uber driver in all of New Hope, Pennsylvania, because that Uber driver was the Uber driver who drove me from the train station to my hotel and then from my hotel to your offices. he, it was the same person every time. And I said, how many of there are you?

And he's like, I don't know. Apparently not very money. we were on a first name basis by the end of the trip, but yeah, it is not the normal business trip destination, but yeah, I met you there the only way I can describe it is you were just so kind because, um, As a vendor, you go on a lot of business trips and you meet with a lot of clients and clients, especially in the industry we were in, a lot of clients know that [00:04:00] vendors whining and dining them is kind of a perk. And particularly in our industry, there weren't a lot of perks associated with some of those jobs. So I do feel like some of the people who worked with, uh, media companies. Took advantage, right? And not even just racking up huge bills, but also really treating us as though we were vendors, like kind of othering us, right?

Like, I would sometimes get the feeling like I was there in service of them. And I just distinctly remember when I met with you, I felt like I was Not being treated like a vendor. I was being treated like a person.

catherine-connelly_3_10-08-2024_101019: Well, I aim to treat all people like people. Um, but what was also lovely when you visited us is, We so rarely got visitors because we were so off the beaten path. And it was like, Abby's coming here. Like, that's fantastic. I, you know, it was mutual.

abby_3_10-08-2024_101019: Yeah. I just remember we, I think it was around the time you were getting married or you had just gotten married. And when we were at lunch, you were telling me how you met your husband and [00:05:00] it just felt like two human people having a conversation and sad to say that was not the standard for a lot of my business meetings.

So it just stuck so prominently in my mind. I figured it was worth sharing. And then. That theme of kindness, I think, is really pervasive because, in all honesty, when I first started this podcast, one of my first kind of pie in the sky guests that I thought of was you, but, you're an incredibly big deal and I know that you probably won't say it.

So I'll be the one to say it. You've had an incredibly successful exit. You sold your first startup to the meat group um, While I had idealized having you on the show, I figured Catherine's kind of the big leagues now. Surely she wouldn't want to be on a show like this. And you have been of the biggest supporters of the show since day one.

So you have such an acute ability to Just really reach out to people and touch them on such a personal level, no matter what level you're operating from. So I [00:06:00] had to speak to that because I feel like for those who don't already know you, that is such a defining quality of who Catherine is and has always been.

catherine-connelly_3_10-08-2024_101019: Thank you.

abby_3_10-08-2024_101019: Oh

catherine-connelly_3_10-08-2024_101019: You're so

abby_3_10-08-2024_101019: This is

catherine-connelly_3_10-08-2024_101019: sweet. You're

abby_3_10-08-2024_101019: Oh

catherine-connelly_3_10-08-2024_101019: sweet. Um, no, I, I, and, and thank you so much. And I, I've been absolutely loving the podcast, as you know. you know, I think that is, you know, that is something I want to put out in the world as I do try to be kind. I do try to, um, you know, celebrate the achievements of others because I think that, you know, that's, that's how we draw each other closer.

that that's the best way to go through the world.

abby_3_10-08-2024_101019: Yeah.

I completely agree. And you've even. You know, mentioned being kind to people actually, it does not. This is why you should do it, but it does have a way of coming back around,

catherine-connelly_3_10-08-2024_101019: It does.

abby_3_10-08-2024_101019: You do find serendipity and kind of these odd coincidences when you make really meaningful connections with people that are true connections. Somehow they have a way of working to your advantage later [00:07:00] on.

catherine-connelly_3_10-08-2024_101019: Right. And I think that that's, you know,

So, so my, my brother, Jeff, who I started my company with, he likes to quote the, um, the poet Rilke, and, uh, one of his poems is like, talks about fighting heartlessly. And really that's how our, we were able to really navigate our space for as long as we did.

So we were at the meet group for, well, the whole story, but like for 18 years. And in order to basically survive here, Board and investors long enough to be, you know, running a company for 18 years in order to, have other people in your industries. Because at the end of run at the meet group, we were doing, you know, lots of B2B deals.

And those types of relationships came up because we were able to reach out. Pick up the phone and talk to people in the industry and they thought highly of us. and so being able to, you know, kind of have that in the world means that you create your own luck because when you're connecting with people in a real way, in an authentic way, and in a fair way.

And you're not, and you're also not being like, full of yourself or puffed up or just, if you're not being heated, if you're being completely, you know, rational and all of that, people [00:08:00] want to continue to work for you. And what you see is, all of our careers are, you know, long enough for this Relationships to reverse multiple times.

And so, what you see is the actions you make leave awake and you want to be aware of that as you're, as you're thinking, like, when you get that rude email, do you fire off the first thing you think, uh, for instance, and, and I think that that was something that we were always very good at, like being like, Oh, yeah.

Let's, let's take a moment, let's regroup and, and just, stay in like that, calm, rational mode, cause you know, that's how we were able to build the company for as long as we did.

abby_3_10-08-2024_101019: Yeah. And it's a differentiating factor, right? people, investors, they're working with companies like this all the time. And if they remember you as the one that meet them with that level of energy. it is, it is kind of a competitive differentiator. So, I can completely, having worked with a lot of different, uh, founder communities, can definitely see how that would make you stand out in a good way. But, um, [00:09:00] so you mentioned starting the company with your brother. I would love to get into the humble beginnings of your startup. Um, where it started, with whom it started. If you could take us all the way back and Yeah. Tell us the origin story of your startup.

catherine-connelly_3_10-08-2024_101019: the company's name was originally my yearbook and we started, got started in 2005. So I was 15, I was a sophomore in high school. My brother Dave was 16, he was a junior in high school. Dave and I were talking, we thought, we were relatively new in our high school. And so, you know, we're trying to meet friends and we're like, wouldn't it be interesting if we could put yearbooks online?

So that's how the idea of my yearbook was born. And we're just like, okay, well, sure. Why don't we just build this? and I guess I should actually backtrack a little bit further. Cause that's already kind of crazy. The 15, 16 year old, we're just kind of like, yeah, we can make that. but the reason that we had that kind of partially ridiculous naivety, but that's ridiculous.

Like, Oh, we can do this. Uh, was because growing up, we watched our brother, Jeff, who's about 10 years older than Dave start and sell his first company. Um, and he [00:10:00] started it when he was at Harvard. And when we, And when he graduated, he moved to an office and he moved out west and we would visit him during the summers.

Our parents would just ship us off there for a few weeks in the summer to hang out there. And, you know, so we, we were familiar with stars. We were familiar with this energy, with this just, It was so different than like, bring your kids to work day with that. We would go to with our parents really.

Oh, we want, we want to this. And so when Dave and I, got the idea, we knew that, entrepreneurship was an option, which, you know, most kids don't, I think now maybe they do a little bit more, but see, I'm seriously, most kids don't, they have so many other things on their minds. Um, rightfully so.

And I think that, you know, being able to just say, okay, well, all right, well, how, how do we do this? And so we pitched the idea to Jeff. over dinner. you know, we're having like chicken cutlets and we're like, so we have this idea for a company and he loved it. He was actually aware of Facebook, being a Harvard alum, he was aware of Facebook and they were only in a few schools at the time.

And he was like, okay, this is, He's like, I, I understand how this could work in anyone to [00:11:00] join us. And so then it was the three of us the, his first company was essay and resume editing. So not really in this thing, Um, so, you know, we did a lot of Google Googling where we found Google to really be the age equalizer, because I think, As we're building, we weren't in any way qualified.

We had MySpace accounts, which again, mid aughts, that's what you had. had a Zynga that's just what we What we used. So it's not like we had any like special development skills. None of us code or anything like that But we were curious stuff and we knew that we could in scrappy enough They were like, okay, let's find out how to do this.

Let's google all the questions We have we found a development team, uh using elamps and they were based out of mumbai and so we would send them hundreds of pages of specification sheets just like pen on paper wireframes detailing and illustrating like You everything the site would have and what, what it would do, which, 2005, every site was doing everything.

So they, it was a lot. and we were, uh, you know, so we would be sending them to our developers, you know, chatting with [00:12:00] them until, you know, sometimes two, three in the morning, we'll still have to get up for seven 30 in the morning homeroom at our high school. You know, I could not do that today be up until 3 a.

m. and then repeatedly get up at 730 and be a functioning human being. So I think being young definitely had its own superpower there. that's how it started was. So we got our 1st, you know, a few 100 members to join from our high school. We were you're Fun shirts to school every day that said things like answering the questions that matter most.

Who are your friends friends and are they hot? silly things, but cheeky because, you know, high school. we ended up continuously, you know, getting people from our school to join. And what was fantastic, what we knew is like actually working when it clicked. It was when people were coming up to us, in the cafeteria around the track and saying, Hey, I joined my yearbook this is what I you should add.

And it was like, this is like what we're building as like a high school. And that was really cool. cause it became like kind of like our high school thing, our project. And you know, it was, it was clearly resonating with the other students. So we were able to open it up to all schools. We didn't have a huge [00:13:00] advertising budget, obviously.

So what we. Ended up doing was we, had a bunch of user generated quizzes and, on my layout things and like glitter letter generators and silly, silly things like that, but people use all the time on my space. And we had a huge stock of them and we created those.

And so, when people would take a quiz, before they would get their quiz results. So it'd be like, you know, what friend's character are you? And, and, we would take registration screen and they could skip it, but a lot of people registered and then they would share their quiz results on their AIM profiles on their Zynga.

And that's how we took advantage of the viral channels at the time and ended up getting our first million members within nine months. And so of launching to all schools. insane growth very quickly. very lucky in sense of like right idea at the right time with an execution that happened to work.

I think that, as we were building, you know, then that's when we finally opened our office so all that time we didn't have an office and we, then we opened it after we got our first million members in 2006. And, uh, that's, and we had been located [00:14:00] in, New Hope, Pennsylvania that whole time.

abby_3_10-08-2024_101019: Wow. Okay. So just to go back to the very inception of this all, you talked about how your oldest brother was an entrepreneur. So he was already in the startup realm. And because of that reason, you and your younger brother, well, still older than you, but younger than your eldest brother. that this was even a possibility and I think that's so, so key because that is a taken for granted thing that most of us don't have. there is this theme of Founders who believe at a very young age that they could build their own business are usually, you know, they have a sibling who's done it, or they have parents who are entrepreneurs. And I just think it's really, it's a really important call out because had you not had the brother you had, and also had you not had the parents you had, because I'm sure that your parents saw your brother do it successfully. That made them feel more comfortable having you and your other brother do it. They saw the potential upside. They saw what this [00:15:00] could look like. And for a lot of us now, I mean, I'll speak to it. my parents are still a little bit nervous about some of the entrepreneurial endeavors because they've largely worked for, particularly my dad worked for other people. So having somebody within your inner circle, take the first step makes such a market impact on everybody else and in their lives modeling that this is even a feasibility to start your own company, creates so much access for everybody else that's surrounding them.

catherine-connelly_3_10-08-2024_101019: For sure. And the easiest way to know that you can do something is, is definitely seeing someone have, has done it before. And it's not just, we saw like he had a successful exit. but we also saw the rest of it along the way. Like we saw him on family vacations having to be at a an internet cafe the whole time because something was happening with his company.

So we saw like, you know, the hard things as well. I think that that also helped. Cause like when we got into it, we knew. This is going to be a lot of work, but You get through it, you do the next thing. And to, to what you were saying about my parents, [00:16:00] for sure. I'm a mom now.

Um, I, my kids are, are younger. They're almost five and almost two, but the, the idea of like, Dave and I are young and we're talking throughout the night, while school's going on and my parents are just allowing it. Uh, cause they know what we're, what we're doing. And obviously that takes a lot of trust from your parents too, to realize they're building something.

They believe in it and to still support it from that point. is huge. And, and I know we're going to dive into this more, but I think it's also, you know, very realistic that my mom, you know, she's was. One of the few women in her field. So when she went to college, which was after she had my brother, so like, she wasn't didn't go right after high school.

She went back to school to become an electrical engineer So I always had that message from her too, that it's like, you can do whatever you want basically. And, and also the other lesson from her was, she, she liked the idea of entrepreneurship cause she always had something to say about her bosses.

abby_3_10-08-2024_101019: it's funny. I've spoken with my co founder about this, Brian, because he had a [00:17:00] business in high school he ultimately ended up dropping out of high school. But, um, we've met other entrepreneurs too, who they had businesses in high school, much like you. And a lot of times your, their parents would discourage that because having a business in high school is a distraction from good grades in high school, which will then get you into a good college, which will then probably get you the corporate job, which as far as our parents were concerned was the ideal pipeline.

So it's so cool that your parents, in all honesty, you staying up until the wee hours of the morning could have taken a toll on the grade you got in your quiz the next day, but they wanted to encourage you to go in the direction of where you were passionate, even if it was a little bit at odds with following this very traditional path of, you know, and I'm sure you probably still got great grades in high school knowing what I know about you. Maybe it would have been a little less palatable if it was really cannibalizing your grades, but still the fact that. Um, your [00:18:00] parents didn't see it as a perceived threat at all is, I think it just created so many opportunities for you and your brother that, isn't really the standard. So that's incredible that your parents were able to be that for you,

catherine-connelly_3_10-08-2024_101019: also when you're a teenage entrepreneur. There's a lot of work your parents have to do that like is unusual. I remember we had like a press interview and like, you know, you don't always like know right away. I can't remember. It might've been Cosmo Girls something, but they were doing like photo shoot at the house.

and my mom's like, So I have to leave work early and clean the house. you know, the things that, I didn't have a driver's license. So she was driving us places. Like there is, you know, so many things like that, that like, know, your parents support and little and big ways, obviously, made a huge difference for me being able to keep building.

And that was true when I went to college too, it's because, you know, obviously then you're out of your parent's home. But, I'm in college, and the very first thing, like, seriously, first class, I found out that, my midterm, was going to conflict with, some planned travel I had.

I was asked to speak at the [00:19:00] World Knowledge Forum in South Korea. It was kind of a big deal. Uh, and it conflicted with the midterm. That professor, um, first day of class going through the syllabus was like, if you're going to miss the midterm, you should drop out. , drop this class, not drop out.

, and there'll be no exceptions. And so, of course, I'm like, come to him. Hi, I'm actually going to be missing the midterm, but, and in explaining my situation, he was so excited to support me. He was just so supportive, so happy for me. And was like, I'm happy to take it early.

And I want him to be clear, like, I do need a special circumstance, but I, I'm not trying to get, get one over on you basically.

abby_3_10-08-2024_101019: right? You weren't trying to get out of it.

catherine-connelly_3_10-08-2024_101019: Right. I was like, I will do it. I, I took the exam when I came back, , it was fine. And you know, he was so, so immensely supportive and just continued throughout, my time in college, one of my, mentors I had my, my sophomore year, I actually had her for three classes.

Um, and she was always incredibly supportive of like what I was building, what I needed, and it just made it so that it was kind of a safe place to ask for help and to feel like [00:20:00] you're going to have that support. And I know how lucky I was because, going through this, I did have other young entrepreneur friends who are like in the same exact life stage, which is also nice.

but, and I was connected to one of them recently and she said, so when she was in college, she had the same experience where like most professors were more than happy to help accommodate her, to help, help her build something, except for one professor who happened to be a social entrepreneurship professor.

but for

abby_3_10-08-2024_101019: bit more. I think that's really interesting. Um, because you would think that being an entrepreneur, other entrepreneurs would support you or. Being somebody in a startup, other people in that startup would support you. But I mean, I've spoken firsthand about my experiences.

startups by nature of being really small and being very under resourced and being very competitive. I feel like a lot of people are operating from a place of scarcity. And, you know, I feel like I've had even female managers who. Felt that they couldn't stick their necks out for me because it would put them in a vulnerable position because they were [00:21:00] the only other female in the organization.

So it, maybe it's not, you know, it's not just a coincidence. I don't know. I don't want to project too much onto this professor. know nothing about him, but it's not the first time I've heard of somebody within this network of startup culture, not advocating for others. Let's just put it that way.

catherine-connelly_3_10-08-2024_101019: sure, for sure. And I, yeah. And like I said, I don't know anything about that professor either. So I don't know if he what was going on there, but it, but it is interesting. And, and you're, your experience is, is totally resonates with, you know, so many people who have had that where someone just isn't, they're not willing to put your neck out.

And I, I, I totally agree that scarcity is a huge part of that. especially when it comes to, getting funding and things like that. Like You want to be supporting people. You'd also, but at the same time. You realize it's like, oh, well, if like, there's only this much money and it's like, well, my company to get it.

Um, and so you definitely start to see that. luckily though, I've had in my own experience, just. [00:22:00] So many supportive people, and there's been like, and I feel like most of my. Most of the negative things, unfortunately, have been from either completely outsiders, or just, they didn't mean to, a microaggression, like, it's like, I didn't realize I was making this difficult.

when I went to college, I was actually originally kind of keeping my yearbook as my secret double life, because in high school, I actually did. Get some, a fair amount of negativity from my peers, which my brother Dave, didn't. And I will say Dave is significantly cooler than me. So that maybe plays a part.

but with that said, I remember I was on CNBC, and my teacher turned it on in the classroom because, , he's proud of me. He's like, and it had been taped earlier, I think that day, and he was put, put it on. And the first thing I had was one of the students next to me saying, wow, you look really fat on TV.

so that was mean, and it was just one of those things of ways to put someone down. I had another situation where we're Spanish class and this was completely unprompted. [00:23:00] The kid in front of me just turns around and says, you know, you're making us all look bad.

and it wasn't making him look bad in Spanish because like, was not very good at Spanish. So it was not about the class. Um, it was, it was things like that, or I was applying for a scholarship and, One of the girls in my class heard that and she said that, wasn't appropriate because I had this business and that's, it's not okay to also look for academic scholarships.

so I, I had just like these, like, little comments, but I think as humans, we hear the negativity and we keep track of it and we might keep of it far more than we keep track of the positive I do this, I'm, I'm a jerk.

When people say like, nice things or , when teachers would like write a nice note on a paper, I totally saved that, uh, because sometimes it's just nice to look through and be like, oh wait, I do know what I'm doing. but so when I went into college, I was afraid of having that same negative reaction because unfortunately as women, , success and likability are, negatively correlated. I [00:24:00] was concerned about that. And actually going into college, there was a negative article about me in one of the Georgetown owned publications that wasn't Georgetown student publications.

But it was just one of those things where I was like, maybe I should keep this to myself a little bit. And it wasn't actually until, and I mentioned my, my mentor earlier, that teacher kind of almost, out of me in the classroom because she was just like, Hey, Tell us about it. and that's when I started actually talking about it to my peers, as well as, you know, the professor said, had to ask for help and it just made, it was just a completely different experience. peers were so supportive. They thought it was cool. They'd , we're like, wow, you're building this.

That's amazing.

abby_3_10-08-2024_101019: I mean, let's be honest when you're in high school, you're just insecure. that is such a foundational period in your development where you're coming into your own and we're all operating from a place of scarcity, regardless of, how well resourced we are.

Like we all have this perceived, idea that everything is kind of, you know, [00:25:00] A zero sum game. And if somebody else succeeds, it's going to cannibalize or create loss for somebody else. especially when you're going through puberty, and everybody's trying to find their footing, it does become just more of a combative place.

And maybe what we see is when we. grow up a little bit and our frontal lobe is a little more developed. I don't know. I'm speaking completely out of turn. I should have my husband talking about this as an educator and not myself, but, I don't know. Maybe there's just a maturity element to it too. When you're in college, seeing somebody else really successful creates more of an abundance mindset, right? Oh, Catherine's able to do this. And she's in my class. This girl in my class was on CNBC. Maybe that means, I could one day be on CNBC. So kind of like a little bit of that reframe that just happens with growing up a little bit. Maybe there's something to it.

catherine-connelly_3_10-08-2024_101019: think there's something to be said about growing up a little bit, but I also think there's something to be said about when you're in college, being able to choose who you associate with in a way that you're not as able to do in high school where, your main affinity towards people might be a zip code.

When you're in college [00:26:00] and taking the same courses, there's usually a little bit more, that kind of has that um, you Reaction. Cause I think it's a huge part of it is growing up. Yes. But I think like part of it too, is just at that point in my career, I had already started to choose the people who were supportive and look for that and not try to be , Oh, someone's saying something negative about me.

Well, I'm going to go talk to this person instead. And I think that that's tough because I think, adults do it too. Adults sometimes put other people down for their successes or just think, okay, well, if we're both going for this job, Then, you know, I'm going to try to, do something to hurt this other, other person's chances.

that happens. That always happens. And I think, being able to navigate how you want to go around the world will be figuring out how to surround yourself with the right people who are supportive of you. Because it is a skill where I think, could take some training to develop, , because.

People go into situations, they want to be liked, and, you know, that might mean connecting with someone who, you know what, [00:27:00] you shouldn't care if they like you. and that's, and, and I think that that's, that's difficult because, there's a kind of a natural tendency to want to, like, please someone.

You should go into things assuming people like you because if you want to have like that, there's like that whole acceptance prophecy where it's you assume people like you, they'll be more likely to like you because you're probably approaching this situation from like, you know, more warm, more friendly yourself.

But you shouldn't want to be like, just because you want to be liked, you should be want to be liked for who you are as a person, for things that you actually value. And then, keep that mind with the other people you're connecting with too. Cause I think that that's, you know, one of the things that's like the people I was surrounded with at the company, we had an amazing team and I'm so blessed.

I got to work with them. That was , so privileged. Like, you know, obviously I love working with my brother, but. throughout the company. It was just the kindest people. Cause I remember coming home from, college one summer. So the summers would be the time where I would be there for like the full stretch.

Otherwise it's mostly doing things remotely. And because of that, especially as , We hired a lot more people after our [00:28:00] series be like, there was a lot of people. I didn't know other than , exchanging emails with or being on a call with. And, you know, at the time, we weren't really doing video calls.

It was, actually a phone call because I didn't have Wi Fi my Wi Fi in my dorm. So even like coming back to the office is like, oh, this is weird.

I don't know as many people as I should. And I remember one of our, um, our database administrators, he sees these things like, Catherine, come to Dunkin Donuts with us. And so if he came with things like every, at that time, I, I'd go to the Dunkin Donuts with all of the DBAs.

And it was fantastic. And I got to know them, well, but it's, it takes that, and you know, that's a relatively small action of just saying, Hey, Come get coffee with us. Come with us. Like being able to make that invitation, being able to like show up for someone who, you know, I'm sure he realized that I was feeling a little a little lonely because I'm also significantly younger than everyone there, , and, welcoming me in and so then that, so that was just something that, , the company did.

I was just surrounded by good [00:29:00] people. And so that, and I think that that kind of shows and how I navigate the company's growth and stuff is like, You know, we had a very respectful team and a very good team. I think that that is why we were able to accomplish so much together and wanted to continue to work together.

abby_3_10-08-2024_101019: yeah. I think it's a really underestimated thing. I think are all people based businesses, and I see a lot of startups not prioritizing people prioritizing ideas and skills that lend themselves to certain ideas. But, especially early stage founders, don't get attached to ideas because they're likely going to change.

I mean, Catherine story is a little anomalous. The fact that you launched something and that thing is what became incredibly successful. A lot of early stage founders need to pivot and try on different ideas and, you know, I think one of the things that I always say is what is pervasive is the people, the people you're building with and the why behind the products that you're building.

And if you're not really intentional about the people that you invite [00:30:00] into your company, the investors that you bring onto your cap table to, to invest in your company, that could cause a huge detriment to the success of your startup. And I think it is. Such an underrated thing not enough people are talking about, so I'm so glad you bring it up.

catherine-connelly_3_10-08-2024_101019: Yeah. So I will say we actually did pivotal time. Um,

abby_3_10-08-2024_101019: did.

catherine-connelly_3_10-08-2024_101019: yeah.

abby_3_10-08-2024_101019: me

catherine-connelly_3_10-08-2024_101019: So, um, so when we first, like the initial idea was basically the Facebook for high school That didn't last into like a month until, until launch basically. so then we became about meeting new people and that we did stay with. So we stayed as for my yearbook, which again, the name, not really about meeting new people, but we stuck with the name until, actually until 2011, we went public and a spec like deal. with a, uh, the company was, uh, KPOS that we merged with this a hundred million dollar deal. We were bringing basically all the revenues the deal. Um, and. now we had these two brands, My PoS, and then we're like, okay, let's be called MeetMe now, because we're about meeting new people.

And the name My Yearbook didn't make sense, so obviously we test it with our users. We figured out, how to [00:31:00] rebrand, which is a whole thing. But then that kind of entered this MeetMe era, where now we're primarily a mobile app. we started as web. I mentioned, , how busy the homepage was.

So we launched on cause like the mid aughts, but now, you know, 2010, 2012, when we were developing mobile app, we had to be very choosy with what stuff we got rid of. And so it was a completely different company in that sense. And now of course you had Android teams and iPhone teams and all that as well.

then we're a meet me for a while, primarily ad based, The ad market started doing poorly. And so we're like, okay, well, what do we, what do we do basically? And

abby_3_10-08-2024_101019: money,

catherine-connelly_3_10-08-2024_101019: yeah, we need to make money. We don't want to be, as tied to just the ad markets, which, there's a whole bunch of supply that just flooded the market.

And that , brought down ad rates. And what we ended up doing was. We saw live streaming as our feature. And so live streaming one to many live streams used to have one person talking to, people who join and in China, it was already incredibly popular. And so we were watching a site, an app called Momo.

And so we saw [00:32:00] them building. We're like, if we can make this work for the West, in the U S like that. Could be really interesting. So we figured out how to kind of adapt it to so that could work for users. And it wasn't something that was like, you know, Twitch was around. but even Twitch doesn't monetize through gifting in the same way. and so basically as a viewer, you're sending the streamer gifts, the streamer gets, um, portion of that gift revenue as, as does the company. And. What it makes it so that which is interesting from like a monetization standpoint is that a lot of monetization features kind of hurt engagement, because like their paywalls or something like that.

But with Livestream, what was interesting about it was it actually helped the content because then to the streamers. We're going to create better content. There was they were motivated to create better content. and of course, you know, we built up a whole our whole talent team and our whole everything that the company built up to support that that hadn't existed before.

And so, you know, I kind of mentioned before, , qualifications are overrated when we were starting as high schoolers. But that was true throughout our, throughout our history. It's like, there was no live streaming experts. we had to become live streaming [00:33:00] experts. There was no guidebook for how to moderate live streams.

We had to figure out how do we make those decisions? Cause that's, that's a huge decision. you're finding yourself in meetings and you're talking about very serious things, like obviously keeping teenage users off the site and things like that. But then there's also things like, can someone eat a popsicle on the live stream?

What other phallic objects should we not allow? and it sounds like a silly question, but it's an answer you need to, things you need to answer because there's, , it's not hard to find, Awful content on even YouTube or even, um, like Twitch, it's, it's pretty easy. And so we didn't want to be that we wanted to make sure that we created, there's moderation capabilities to go with it.

But to do that, you had to answer questions that. There were no answers to, while I was there, we also published a transparency report to try to share with the outer industry. Like, this is what we're doing. This is where we think others should be. So that way others could share what they were doing too, because there needs to be a lot of communication on those aspects of business to grow because, you know, it's, safety isn't A differentiating factor.

It should be the table stakes. Like [00:34:00] so that we always had to develop. And so as we grew, so then we had live stream as a whole thing.

We acquired a whole bunch of apps, uh, to become the me group. and we did that because, we believed in live streaming. We're like, if we putting all these resources in it, let's have a bigger reach, let's get other apps that are like ours and become a bigger company. And so that's what we did with our acquisitions. and then we were eventually acquired in 2020 to the parent company, of eHarmony it's a large German company, but the e harmony was to be the most owned brand in the U S in a 500 million deal. And so that brought us back private. And, and so then it was like another different, thing where we were also working on our B2B business, which we just started, excuse me, right before that acquisition.

and so I left in 2023. And I think that, the people that I worked with, a lot of the, we had people that were there for very long time, we had fantastic retention, especially compared to tech industry. And I think part of it was people were respected and everyone had this Curiosity, wanting to learn, wanting to be on the working on the next cutting edge things.

And so I think that's why we kind of [00:35:00] grew together. And so all through all these different phases of the company, we had our team to really rely on and really, be supported by.

abby_3_10-08-2024_101019: that's incredible. I think it's a testament to the leadership as well. I mean, people always say people don't leave companies, they leave managers. And so I'm sure the way that you hired, you were ruthless about hiring, you were Managers are executive leaders that would hire other great middle managers who would hire great individual contributors.

Like it really does start at the top and with the core founding team as well. With the core founding team, you set the cultural DNA again, like the value system, like you said, that is going to be pervasive throughout the entire organization. So yeah, sure a totally a testament to what you and your brother collectively decided, you know, this is the who of, of who we want to make up, meet me, at the time. But I would love to get back to were very young and you were hiring people senior to you and you're one of the youngest people in an organization you owned, [00:36:00] which is. So anomalous. We get a lot of people on this show who have very early entrepreneurial itches, and they'll start businesses very young, but it's very rare that they Go public or they have such a media presence so young.

So I'd love for you to speak a little bit to that because I think that in and of itself is a way that you are a very vulnerable person in that position. You're not just a woman, but you're a young woman flying to different parts of the world. being subject to media scrutiny. Tell us a little bit more about that because I think that's so unique and in a lot of ways, I'm sure so, so challenging.

rubber.

catherine-connelly_3_10-08-2024_101019: Especially when it came to, so when we were first public, Yahoo finance message boards, were

abby_3_10-08-2024_101019: always

catherine-connelly_3_10-08-2024_101019: buzzing, and

abby_3_10-08-2024_101019: there was photos of

catherine-connelly_3_10-08-2024_101019: of me on my,

abby_3_10-08-2024_101019: You You

know,

catherine-connelly_3_10-08-2024_101019: on my myYearbook profile, obviously there's photos of me and there's , a photo of me at my cousin's wedding.

So I'm wearing a nice dress. and some of the day traders, I guess, took that photo, posted it and started making vulgar comments. And I was 21, it was absolutely [00:37:00] disgusting. And, and things like that, were common on this message, versus obviously if you go into message boards, like.

it's like the worst of the internet. you would hope that finance ones were different. They weren't no, of course not so they were just awful and it of course is hurtful and disgusting but It's also like you said, like my age, and what really helped me get through that wasn't just I'm not going to listen to that or whatever.

It was really just that I had another woman in my company reach out and say, Hey, you know, I see you. That's not okay. And kind of talked to me about some of her experiences going through, going through her career because she was, , a little bit older than me

and she told me like how she navigated it. And. Being able to have someone reach out and kind of take me under her wing was incredibly helpful for dealing with that because it is a lot of pressure where it was difficult was definitely dealing with investors or sometimes dealing with outsiders. I remember, uh, one investor An activist investor was questioning Jeff and he was trying to drill into like, why am I but he wasn't [00:38:00] talking about me.

He was like alluding to my title, which I'm actually not sure if Jeff knew what my official title was at the company at the time. it was like VP of brand strategy or something. And, yeah, centric. So that wasn't something we would talk about. But Jeff When he realized what the question was, he's like, are you talking about my sister and co founder of this company?

and so he, you know, took it right back to like, course she's, of course she's doing this. when you would have those, you know, it's one thing to defend yourself, but when someone else defends you, it's that much more powerful, and then you're able to, realize and have the confidence, like, I belong at this table, um, even though I might be, a decade younger or something that, I still belong here,

abby_3_10-08-2024_101019: I think it's so critical too, because in both of those examples, , the woman who reached out to you was older, you know, she had more tenure, even though it's funny because you hired her, she was older. So in a lot of ways, she, the power dynamic was, she was someone who had a lot of credibility in that situation.

Same with your brother. , unfortunately he may have not been that much older than you, but he was a male. And

catherine-connelly_3_10-08-2024_101019: Oh, he was 10 years older too.

abby_3_10-08-2024_101019: Yeah. [00:39:00] Okay. So he was 10 years older again. So it's, it's great to have people who, while it's easy sometimes to want to alienate people with more privilege than you in certain situations, to the extent that they can be allies, that is incredibly powerful for you because they're going to have leverage with their words in a way that you just can't.

in a moment like that, I'm sure you were almost shocked into submission. I love when people are. Always questioning women, like, why didn't you say anything? And sometimes it's when these things are happening to you. It's an outer body experience. You don't even have words. You, you're literally shocked into, into submission. And so to have somebody else with a little more agency in the situation, come and speak on your behalf is, So, so critical. So I've always been a big, strong male allies, strong, whomever in the industry has a little bit more, credibility or leverage or just privilege, rather than othering people like that, if they're being helpful to invite them in, they can be your biggest [00:40:00] advocates.

catherine-connelly_3_10-08-2024_101019: Yes. And you know, I think that something you said before, like, yes, even though I was in this system, like hiring people and like, when it came to finding who your mentors are, your mentor doesn't have to be someone who, well, first of all, I have a lot to say about mentors. Cause I think that, that no, there's no like unicorn mentor for most people. What you want to look for instead is people that can kind of guide you when you need to be guided. And so that's going to be, you know, when I turn to the woman in my company to help me with those specific issues, or like my brother, huge mentor of mine for, for different things.

And, and, and even like my peers, even in people in completely different industries, it's finding parts of your stories that align and that can, that can support each other. And. What's amazing with working with people, too, um, and just advocating for others, because back then, you know, yeah, I had some power, but, your power increases as your career goes.

And then you're able to say no to things that you didn't used to be able to say no to. It's, something, it's a privilege that you don't really recognize it. [00:41:00] Unless you think oh, wait, I didn't used to be able to say, no, I'm not going to take that opportunity because of this.

You have to be like, I need to say yes to everything. it's different as you, as you get older, or as you get more experience and, and you're, and you have that power, But what you find that when you begin advocating for others, is that it brings you up to and when we mentioned before, like sometimes it's, you know, because the scarcity, like there can be some situations where people didn't want to stick your neck out for you.

And that's awful, but it's also not supported by research. The research,

abby_3_10-08-2024_101019: Yeah.

catherine-connelly_3_10-08-2024_101019: when you advocate for someone else, when you're trying to get something good to happen for someone else, when you say, Hey, did you hear this great idea that they had and you amplify their ideas.

You look good too. Um, the depression, people have a view, makes people more likely want to work with you as well. So if everyone can just take into their, their workplaces that want to amplify, that wants to help and to, you know, kind of have that no strings attached, like it's going to bring everyone up

abby_3_10-08-2024_101019: Yeah, we Catherine you and I talked about this [00:42:00] it was funny. I was talking to my husband about this notion of how creating accessibility for one group of people creates accessibility for everybody, right? there is this perceived threat and you talk about this in chapter 13 of your book, which I was privileged enough to be able to read in advance. There is this perceived threat that if Somebody, if a marginalized group gets some level of accommodation, it is going to require a sacrifice from another group of people. And that's just largely untrue. And yeah, when you kind of create like an education, it's called universal design. Everybody wins. And one of the examples I think of this, you talked about I think lactation tents at a marathon for women, for athletes who are breastfeeding. I thought of it during my time at Facebook. Facebook was incredibly accessible place, especially for new mothers. And they, had, lactation rooms, like rooms where you could breastfeed as a woman. And nobody was slighted by it. Yes, maybe there was a couple instances where, when we were short on conference rooms, sometimes people would want to take [00:43:00] advantage of the mother rooms to use them as conference rooms, but then they'd be ushered to, no, use another room. It is funny. I think people get this idea, they have this preconceived notion that, It's going to threaten them. I think about this not to get too political, but I think about this when it comes to the idea of gender neutral bathrooms. I know the idea of gender neutral bathrooms makes a lot of people very upset, but when you go a gender neutral bathroom and there's two of them, what does that mean?

That means, Shorter lines in both bathrooms for both sets of people for all people and but again, talking about it. Certain people get so heated, but the practicality of it when you're actually confronted with it. It's like, Oh, everybody can acknowledge. This is actually just a way better system in general.

Catherine. Why do you think? certain people, and I'll admit to this, too. There's certain ways that I can kind of think that something might be or create scarcity for one group of people. Why does our mind [00:44:00] go there? Why are we afraid of universal design and sometimes creating access for everybody?

catherine-connelly_3_10-08-2024_101019: I mean, I think that we just kind of default to panic mode. and so Oh, something is changing. I don't like that. Let me, let me push back on that. some of it has to do with messaging too. In my book, I talk about how a lot of the DEI backlash partially was because how it was handled in a lot of organizations is actually through anti harassment training, things like that.

It's actually shown to actually. Worse for DEI than actually thinking of the actual actions that are being taken. It's not, and I think when you think of the actual actions, like, oh, it's the same bathroom, and now hey, this is a whole pooling principle thing, like there's no longer a huge line. that's fantastic.

but that's a, a solid action that whereas when it's talking about the, the principles people feel. I think they panic when they don't understand what the repercussions are. I mentioned this too, like men are, and there's a fantastic article by in Bloomberg about this recently too, but it was, it was like, men, um, think that DEI initiatives like that hurt [00:45:00] them and they don't realize Their privilege is still, is still intact.

and there's a one study that showed women within STEM fields have to have a 4. 0 GPA to be, have the same level of interest as men who have 3. 75. you know, one group can start rising up, it doesn't mean that you're still, that you're affected.

It just means that everyone has to. work together and listen to each other and see, okay, well, what are the actual actions we can take to create the diverse workforce so, so lactating women have a place or, you know, people that are lactating have a place that they can, they can do that.

a lot of this, a lot of this is once you actually think about it, Oh, that's actually not that hard. Let's, let's do that. I have to plug my friend, uh, Tiffany use book. anti ableist manifesto. and that just came out today, literally today.

abby_3_10-08-2024_101019: Right.

catherine-connelly_3_10-08-2024_101019: Um, but I, I interviewed Tiffany my book and of the things that she talks about is like, there's accommodations versus there's accessibility and accommodations is putting that, um, that [00:46:00] bandaid on at the end being like, Oh, let's try to fix it a little bit.

And accessibility is just thinking as you're building. new spaces. How can we make it so that we center the right people? men have been centered so much in how everything has been structured.

And Now it's not so much that we're Oh, so let's say let's center women. Like, that's great. Let's center women. Sure. But just in general, rethinking how everything is structured will help everyone. Because when you think about like parental, parental leave and things like that, men want it too.

Men of this generation want it too. if we can think of like what everyone needs at the, you know, and center. More needs there, then then you can create an environment where people can go in and just feel feel like they belong and feel like they can give their best because they're not holding back a piece of them because they're, you know, not not comfortable or because they know that.

a part of them will make them [00:47:00] othered. and so if you can create an environment and make it more accessible from the start, um, then you're going to welcome more diverse talent. And, there's been so many sides of the show. If you have, if you have diverse talent, your company's going to do better.

abby_3_10-08-2024_101019: A hundred percent. Yeah, even just from again, if we just go back to the practicality, which I think a lot of people think these things are impractical. DEI is impractical. Creating accessibility is impractical. there's substantive research that says if you hire diversely, you have less bias in product.

You have just less, uh, erroneous features, things just get checked and and and diverse perspectives get accounted for, which is so much better for that to happen before you launch your product out into the ether. And then you get a lot of backlash, right? Because something was missed.

catherine-connelly_3_10-08-2024_101019: Right.

abby_3_10-08-2024_101019: another thing I'll say is, I do think that It's really important to acknowledge one's own privilege in a situation, even with universal design, even if we're coming into spaces where everything feels very [00:48:00] equitable, I generally find that. When people are afraid of change, it's because they themselves feel a sense of lack. They themselves feel as though they're already missing out and they're going to miss out more. I feel that the people, I'll, I'll, you know, say it more broadly, the men in my life who don't feel by women's success, generally are men who are very, Understanding of their own privilege in a situation. And I think that's good because once and this isn't true of, I mean, there's a broad spectrum and there's so much intersectionality, it's more than just gender. There's race and everything. But I think when you can acknowledge, and I do this myself too, the amount of privilege you carry in any given situation, because let's not neutralize that everybody carries privilege in a given situation. Once you honor that, I feel like you can get a little bit more comfortable because you know, You do have so much that you're not really, even if conceivably you did have to sacrifice a little bit, you'd [00:49:00] still be operating with so much. I think where I do see a lot of that fear and fear of change come from is when people feel like they're already having things taken away from them left and right.

But, but if you acknowledge that you actually have a lot of things already afforded to you, maybe that liberates you a little bit from some of that fear.

catherine-connelly_3_10-08-2024_101019: Right.

Right. I think it does. And a lot of times too, it's like we're talking about like, well, what doesn't work One of the things that does work for increasing DI and things like that is flexibility in, in your work. So being able to have flex time, being able to, you know, maybe work remotely.

Those are things that everyone found out how much they benefited by, um, in the, in the COVID and that was something that had been completely closed off as an option. And now you find out Oh, if we can create a flexible workplace, then we're actually going to keep more people.

and it benefits everyone. Cause it doesn't just benefit you. If you have, say you're in the sandwich generation, you're caring for like an older relative, as well as like a child or something like that, where, you know, you might need some [00:50:00] flexibility because of that. It also benefits you if You're driving to work and your brake light goes on, or, you know, something like that, or you need to go to the doctor's appointment, everyone needs some amount of flexibility, and you might need a different flexibility than someone else does, but being able to figure out, like, how to build workplaces that honor that those are the types of changes that, that can make a huge impact and that really do help everyone.

But there's like the fear of like, well, this is how we always did it. So this is how we need to do it again. And that's just not a good reason for doing anything.

abby_3_10-08-2024_101019: does create a little bit of that abundance mindset and everybody if everybody's being afforded something great, that gives them more time, more flexibility. Yeah, I just feel like we're, we're less likely to feel abrasively towards other people. and again, I think you were a testament to that in the way that you built your company.

I mean, everybody there was treated with a certain degree of, dignity and kindness, and it made for a less combative workspaces. I mean, I know a lot of corporate environments where there's opportunities. That's absolutely not the [00:51:00] case. So yeah, we see the proof in the pudding time and time again. So I'm so glad that you are speaking openly about the way that you ran your company.

and I know you get a lot more into this into your book, designing success. So Catherine, this book is actually, by the time this episode airs, it's going to be out in

catherine-connelly_3_10-08-2024_101019: Yes.

abby_3_10-08-2024_101019: audio.

catherine-connelly_3_10-08-2024_101019: Yay.

abby_3_10-08-2024_101019: I would

catherine-connelly_3_10-08-2024_101019: Or a paperback and ebook. Audiobook will be in April. I'm staggering it a little bit.

abby_3_10-08-2024_101019: Okay. Well, they can listen to this podcast on repeat until the audio version comes out

catherine-connelly_3_10-08-2024_101019: Yes.

abby_3_10-08-2024_101019: like an aperitif. But, I would love for you to clue our audiences a little bit more into what they can expect of Designing success. Tell us a little bit about it and then where folks can purchase it if they so choose.

catherine-connelly_3_10-08-2024_101019: Yeah. So designing success is know, basically lessons I've learned through my 20 years building as a, you know, female tech entrepreneur. And so I go into things that, you know, will help you design your own life in a way that supports your actual goals versus the goals of like what.

society has said it should be. [00:52:00] So it's kind of a way to really defeat burnout. so for instance, how to set boundaries more effectively, how to be a more efficient decision maker, how to engineer serendipity and foster connections with the people, how to create more time in your day. and so it's, it's really just about, you know, through my lens of entrepreneurship, figuring out like, how can we all, create the life that we actually want. um, and it was a lot of fun to write. I found out I love writing when I was doing it. So yeah, a designing success as should be, we'll be on Amazon, Barnes and Noble, all of the, you know, where you get your books.

abby_3_10-08-2024_101019: So exciting. I can't wait. I'm going to be that person that goes to Barnes and Noble and I'm going to read or I'm going to find the book and then I'm going to put it at the storefront. Like I'm going to put it at the front of one of the display areas.

catherine-connelly_3_10-08-2024_101019: Oh, actually, I should say, um, barnesandnoble. com.

but actually, yeah, to get your book, into bookstores, you, You need to request, like, each individual bookstore. It's not like Barnes Noble, like, corporate.

You actually, like, go to each Barnes Noble and, like, be like, can you list my book? So if, if you want to ask your Barnes Noble to [00:53:00] carry Designing Success, that would be great.

abby_3_10-08-2024_101019: Perfect. That's where I'll be. And I think it's so timely. This is the perfect time for this book because I know a lot of people in corporate right now are dealing with burnout. it's really tough too because it's an hard job market. So a lot of folks feel that they don't have agency, to speak up for themselves in their corporate environments.

So a lot of people just feel incredibly stuck. And I don't think it could be a better time for a book like this to enter into someone's life.

catherine-connelly_3_10-08-2024_101019: Thank you.

abby_3_10-08-2024_101019: Well, Catherine, this has been such an incredible conversation, but I expected nothing less of you. Um, we know where to find the book. If folks want to get in

catherine-connelly_3_10-08-2024_101019: Oh, yeah.

abby_3_10-08-2024_101019: individually to speak with you about anything else, learn from your experience, is there a way that they can best, reach out?

catherine-connelly_3_10-08-2024_101019: Yeah. So my website, uh, see connelly. me. So C C O N N E L L Y. me. and I also do, virtual office hours about once a month. And so, happy to connect with more people, but yeah, that's the best, the best place to find me.

abby_3_10-08-2024_101019: I'm sure we'll have folks taking advantage. Well, Catherine, thank you so much [00:54:00] for giving all that you give and all you've continued to give throughout the years. This has been such an amazing conversation. So thank you again so much. And thank you for being such an advocate of the show.

You're, this wasn't a micro moment of kindness. This was a huge act of kindness and I'm forever, forever grateful for it.

catherine-connelly_3_10-08-2024_101019: Thank you, Abby. Thank you so much for having me on. I love talking to you and, you I loved the opportunity. So thank you.

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