Business Breakups with Bonnie Bogle

Business Breakups with Bonnie Bogle

 
 
00:00 / 00:44:11
 
1X
 

Breaking up is hard to do—whether you’re ending a business relationship or a marriage. Bonnie Bogle’s done both, and she’s here to tell us about the good, the bad, and the it’s-just-plain-complicated.

Bonnie cofounded Mapbox, one of the largest providers of custom online maps in the world. But after growing the business from zero to more than 200 employees, she left it all behind. Now she’s the director of Brazen in Philadelphia, where she works with startups at the start of their journeys.

Bonnie tells us about what it was like to launch Mapbox with her husband as her business partner—precisely at the moment they decided to get divorced. She also shares what it was like to leave that same company after building it into a massive success. Oh, and how she knows the secret behind McGruff the Crime Dog’s life story.

Who cares if this is super unusual? Yeah, we’re getting a divorce, and we’re starting a company together at the same time, and screw it! Let’s just do it. We both want this.
Bonnie Bogle, cofounder of Mapbox and director of Brazen Philly

We chat with Bonnie about:

  • Why living in Peru inspired her to create her first company, build open-source websites, and ultimately provide access to better maps
  • How everything Bonnie learned running operations for a quickly growing startup became the backbone for how she’s helping other new businesses launch and grow
  • How to decide whether and when to let go of something you love

Follow Bonnie: Twitter | Insta

We also dig into…

  • When leaving a job is bittersweet, so you hang around for a month (or more)
  • Toxic companies, toxic bosses, and realizing when you gotta GTFO
  • Crying in the work bathroom: the worst, but also sometimes totally ok
  • Breastfeeding at meetups, in Parliament—and wherever the hell you want to (if you want to)

Sponsors

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Transcript

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Jenn Lukas Hey, welcome back to No, You Go, the show about being ambitious—and sticking together. I’m Jenn Lukas.
Katel LeDû I’m Katel LeDû.

SWB And I’m Sara Wachter-Boettcher.

KL Our guest today is Bonnie Bogle. She’s someone I met about six years ago in DC when she was Head of Operations at a company called Mapbox. And she cofounded and bootstrapped Mapbox. Back then, it was a few people and pretty soon it was hundreds. And then last year in 2017, Bonnie walked away. So we’re going to talk with her about all of that and her journey—building the company and deciding to leave it and what’s next. It’s kind of a cool story.

SWB Yeah, I really liked chatting with Bonnie because I think we talk with folks a lot about starting new stuff but we don’t talk that often about when do you decide that it’s time to go? Especially when it’s something that’s really close to you—right? Like, she spent a lot of time building the company and to walk away from it was a huge deal. So, I think we should talk more about knowing when it’s time to leave… whatever! Leave a job, or leave a side project, or leave a company you started.

KL Yeah, seriously. I think about this with National Geographic because I was there for over six years before I joined A Book Apart. And there were lots of reasons I left, many of them were positive like looking for a new challenge or working with difficult people. I also had just never worked with a smaller company, which was interesting to me. But—I don’t know—there were also a bunch of negative reasons or reasons that didn’t feel so positive that I left. And I realized at a certain point that I’d gotten to a certain level of management and I think I had gotten exposed to—you know—some toxicity and some politics and some bullshit I just wasn’t really loving. And that made me unhappy and that was spilling over into how I was interacting with my team, which sucked. And it was in the middle of the summer I think and we were dealing with a whole bunch of projects, like a whole bunch of deadlines were hitting and our team was understaffed and somebody was out for vacation for a couple weeks coming up and then somebody else on my team asked if they could take the same two weeks off and I like…said no. I just basically was like “no you can’t” because I felt like I just couldn’t be with like one less person and thinking back on that, I’m just like I can’t believe I had that conversation with that person.

[3:01]

JL What was it like having that conversation with that person?

KL Yeah, it was terrible! Like I think back on it and I was feeling a lot of stress and like I said, I think that was kind of spilling over into how I was dealing with my team and I felt so shitty that I had treated that person—you know kind of like not—not with a lot of respect by just being like “no because I say so.” Like that’s terrible! And I—I don’t know—I think at the time I didn’t—I felt like I didn’t have any other choice but really I did and it just makes me so sad that that’s how it went down.

SWB I’ve definitely felt like I was in a situation where I was struggling so hard to keep my head above water myself that it was really hard to make space for advocating for the people who were reporting to me. And that’s definitely one of the big reasons that—that I left the job. I mean I remember managing a team and I realized that I was spending so much of my time managing up, so some of that was—you know—making sure that I wasn’t getting the short end of the stick with management. Part of that was also being the shit umbrella—right? Which is where like you want to prevent the shit from upstairs [laughing] to come down on your whole team [KL laughs] and so—you know—when there were questions about things like what everybody’s workload was and whether—this is at an agency—so whether everyone was sort of fully utilized, as they say. So like how billable are people? Are they making enough money for the company is fundamentally what that means. And whenever those kinds of conversations came up, I had to fiercely advocate for the people who I was working with and make sure that they were essentially protected—right? That nobody was perceiving them as not contributing enough because they were working very hard. That was very consuming for me and I did not feel like I had enough space or time or energy left to do a lot to support them or sponsor them—give them opportunities to shine or to grow. And that is something that I really wish that I had done differently and I think ultimately the kind of—kind of like you mentioned, Katel—toxicity that I felt coming at me all the time, that’s when I basically decided like “I gotta get out of here.”

[5:12]

KL Yeah, this is also just making me think back to that time. [suppresses laugh] And I was in an office with big windows that like looked out onto the floor where the rest of my team was and [laughs]—two of my team members sat directly outside my office and I just remember like sobbing [laughing] because of something, like some meeting I had come from and being like so overwhelmed and I just looked up and they were [laughs] watching me and I was like “oh god, [laughs] this is bad.”

JL Oh my god [laughs]. [KL sighs.] I have a line when it’s time to go and that’s crying at work. And not because it’s not okay to have feelings—

KL Totally.

JL —but if any place is making me cry, I am like “get the fuck out, you do not need to be in a situation like this.” [KL laughs] And I know that’s easier said than done—right? It’s not always easy to just be like “okay, I’m going to get a new job…like tomorrow!” But there’s just a line of respect that I need people to have at work. Not just to me but me to them and everyone all around. And so there was—I had a job this one time and someone yelled at me. [KL sighs] And I am so not okay with people like yelling, scolding people. And I just started crying. And I couldn’t stop, I mean I was just like—I closed myself in—in office in attempts to stop crying because I didn’t want to leave the office and have other people see me cry. And that was it for me, like mentally. I still ended up working at that place for a couple more months but it was like me creating my exit plan.

SWB Yeah, I feel like those kinds of events can be like a wake up call. But I do wish, Jenn, that you had been that little angel over my shoulder for all the times I was crying in the bathroom. [laughing] Because I’ve cried in a lot of work bathrooms! [JL laughs] And it didn’t really occur to me to be like “wait a second, you shouldn’t have to be doing this!” And I think it’s fine like look, if you cry in the bathroom, it’s okay. Everyone cries, it’s fine. But to look at that and say okay, it’s not just something wrong with you that you’re crying in the bathroom, it’s like what’s going on that is enabling that to happen over and over again.

KL Yeah.

JL There should just be signs in the bathroom. [laughs] You know, not no crying—it’s okay, your feelings are okay—but like no to that—

SWB But like—
JL —asshole who made you cry. [laughs]

SWB Yeah, [laughing] exactly.

JL You know, and there’s times—again if everything else was perfect and this was just a random situation where—I don’t know—someone was having a real shit day and I accidentally got yelled at—you know? But it wasn’t. It was representative of a toxic situation that I just shouldn’t have been in anymore and it was time for me to go.

SWB One of those moments for me was when I was actually being harassed by this guy who did not work for my company but he was a vendor, so it was a third party service we used a ton, so we had this really close vendor relationship with them. And I went to their big vendor conference because my team was responsible for this relationship and we’d been like—just like normal conference things. We’d been out at drinks with a coworker from my company and—you know—went back to the hotel, I am going to my room to go to bed because I am a reasonable adult. And I started getting all these gross texts from him trying to get me to come to his hotel room to play.

KL Eugh.

SWB And it was—it was very gross. And I had spent the whole evening thinking like—you know, we had talked about—I don’t know—the farmer’s market that he likes to go to with his wife and how he had just dropped his daughter off at college. Like I thought we had been having a very normal conversation! He thought that he was like teeing up this whole extra scenario. So it was super gross and obviously he was gross, but one of the things that was a huge sign for me was that after that happened, I did not feel like I could talk to the owners of my company about it. I did not trust them. I did not trust what they would say or do about it and I did not feel confident that that scenario would end in a place that was any safer for me. I knew, for example, that one of the owners of my company, like the vendor relationship we had with this other company was so important to him that I was like “he is going to prioritize that relationship over me.” [KL sighs loudly] Which like—

KL Not—not okay.

SWB So because of that, I did not go to them. And it was just like I reported to the owners. I was a director reporting up to the owners and I had this team of like six people who worked for me. And a couple of them worked with this vendor all the time. And so at one point I quietly sat down with these other women and warned them about this guy. And I look back on that and I think what a sad state of affairs—right? As their manager, I was effectively telling them that they couldn’t trust that they were working in a place where they would be safe—right? I was effectively warning them about a creep as opposed to preventing a creep from being in their workplace. And I don’t think anybody should be in a workplace where somebody is going to harass or assault them. And obviously, self included—right like this should not have been happening to me—but that was definitely a moment where I was like “oh my gosh, I can not do right by them.” And I regret it in some ways. I mean, at this point, I would absolutely push this issue forward and I would go to their company and I would make a stink about it to them, I would make a stink about it to the owners and I wouldn’t shut up about it until something changed, even if that meant that like I was pushed out. But at the time, I felt really scared of that and I also felt like I had no idea where to even start. That was when I really realized—this is an environment where I am not going to be able to affect any change that is good for anybody, myself included, because this obviously objectively awful thing has happened and I don’t feel safe enough to even talk about that, so what the fuck [laughs nervously] am I ever going to be able to fix here?

[10:58]

KL I give you a lot of credit for—I mean, you know—going through that and looking back on it. And obviously it’s so hard to not have feelings of like “I wish I had done this.” But I think that that is something we fall into when we’re sort of—a little earlier on in our careers and we’re managers and when you’re in an environment when the responsibility to like do the right thing is—is only and constantly being placed on you, that’s not necessarily fair. It’s not that you’re not going to do the right thing but when you don’t have a structure—like you said—through which to kind of make things better, that’s—that’s really tough.

SWB I’m curious. Have either of you ever left a job that you really loved and that was like a place that was good and you felt really close to, but you felt like for whatever reason, you had sort of gotten what you needed to get out of it?

JL Totally, yeah. I have a couple of times actually. My first job out of school—I worked at Lockheed Martin—and though that might have not been the [laughing] perfect fit for me—I don’t know if everyone would imagine me working there—I worked with a bunch of really great people. But the issue with working at Lockheed Martin is you’re working on a lot of confidential things and if I ever wanted to find another job, I couldn’t really show my portfolio. Because I was more the web design field—right? [laughing] So it wasn’t exactly the perfect match for where I wanted to go in my career trajectory, so I knew that I sort of had to make a move because if I stayed there, it wouldn’t follow my career goals in life. So even though it was a really great job with really great people, it just wasn’t the perfect fit for me and what I wanted to do. So the long term picture made it sort of easier for me to leave that job and try something new.

SWB Jenn, I know also that you ended up working at Happy Cog a few years later—an agency—and that you were there for several years. And I remember when I met you, you worked there. And I just really strongly associated you and Happy Cog. [JL laughs quietly] You’d been there a long time, you seemed so crucial to that place. And so I’m curious, did you feel that way—like Happy Cog was a big part of you and was it hard to leave a place that was—that you felt so close to?

JL Oh yeah, I still say “we” when I talk about Happy Cog. [KL laughs] You know, so I’m like “oh yeah, we did really great things there,” it will forever be a “we” for me. I absolutely loved it, felt very invested in that company and the success of it, still do follow them and always—like “oh what’s everyone doing now?” The thing is though—you know—I was there for six years. And I was doing a lot of speaking and I was just doing a lot of different work and I always wanted to try freelance. And it was really a good point in my career and my personal life for me to go out on my own. I had done—tried doing freelance once and that was right out of school and let me tell you, [laughing] that was not a good time for me to try freelance. But it just felt like this was a really good time for me to go out on my own and try consulting and focus more on the speaking. I was running Ladies in Tech at the time and I had a lot of just like writing and speaking engagements and I was like “I’m going to go for this!” So I had enough confidence to be brave to leave that job and try something new that I wanted to always try.

SWB Was there a sadness about leaving a place that you did feel so connected to and almost felt like, like you said it was a “we,” like you felt such a part of?

JL Totally, it was one of those things where the people I worked with will always be my friends and—you know—there was even like, “hey if you want to come back and work at the office, you can.” Which I definitely felt like I could, but I also sort of needed to separate because I needed to feel that separation. But you know, you keep in touch and you know—you just—you move on and there’s other things.

KL Yeah, it’s funny that you say that because when I left Nat Geo—I mean, that was super bittersweet. And I remember that I gave a month of lead time—

JL Yes [laughs]

KL —and I kept—[laughs] and I kept telling myself that I was doing that to make sure I handed off things and that everything was smooth but looking back, really that was for me to—[laughing] to be able to let go.

JL Yeah, when I left I gave six weeks! [KL laughs]

SWB Yeah, I think this is something that Bonnie talks about a little bit about just sort of that—how do you let go? And feeling like you’re ready to let go and that it’s time to say like “okay—you know—this thing that I thought of as mine and us is no longer going to be mine and I am going to let it go out into the world and it’s going to do what it’s going to do.” And I think that that’s a really important part of growth—you know—when you have to let go of this one vision about yourself and your job and your life in order to pursue this other vision of yourself and your life.

[15:26]

JL I can’t wait to hear more about that! [music fades in, plays alone for five seconds, and fades out]

Interview: Bonnie Bogle

KL Today we’re talking with Bonnie Bogle, the director of Brazen in Philly, a community for women entrepreneurs. I met Bonnie when we were both living in DC and she was in the midst of running and growing Mapbox, one of the largest providers of custom online maps for websites and apps. And she’s gone from writer to entrepreneur to community leader and we can not wait to hear what’s she’s up to. Bonnie and I ran into each other in April and I almost squealed with delight at realizing that we live in the same city again. So needless to say, Bonnie, I am really happy you’re joining us. Welcome to No, You Go.

Bonnie Bogle Thanks, it’s great to be here.

KL So I want to just go back a little bit. You started out as a writer for the National Crime Prevention Council and the Nonprofit Technology Network. It seems like you’ve always sort of wanted to do work that benefits the public good. Can you tell us a little bit about—you know—just sort of starting out and what your early career was like?

BB Sure. What brought me first to Washington, DC, was I went to college at American University and was lucky enough to have a lot of internships and then one of the ones that was probably most influential on me was when I worked for the local NPR affiliate. And that was where I realized the public good of community radio and also where I realized that my lifelong dream of being a journalist was actually not the right fit for me. [laughs] So when I did start off my career being this writer for—you know—something that was crime prevention, which was interesting to me on the local level but then also within technology was appealing. And also I was at that nice age range where coming out of college I knew how to use a computer better than most people, like that moment in time where the internet was on the newer side of things, so that was also an easy job to land.

KL Did you ever meet McGruff the Crime Dog?

BB Oh my gosh, so I actually, I wrote in his voice—was largely what I did when I was there. Because what I did was I ran the children’s website. I was not tall enough to actually wear the dog suit myself [KL laughs] thankfully, however one of my claims to fame in that job was I wrote the life story of McGruff, on how he actually became the Crime Dog.

KL Oh my gosh, that’s very cool. [laughs] I love that.

SWB I have so many follow up questions about McGruff but I feel like they would derail this entire interview. [laughter]

KL Well, we’ll do a follow up.

KL So skipping ahead, you started your first company Development Seed when you were twenty-three and then three years later you co-founded another one called Mapbox, as I mentioned before. Can you tell us a little bit about that journey?

BB So, right after college I was actually living in Peru for a year and that was where we started Development Seed. I was down there with Eric Gunderson who is actually—he was the cofounder of Development Seed and later Mapbox as well—and we were following everything that was going on in the United States, which was open source technology and being used in some campaigns—like particularly Howard Dean’s campaign in interesting ways that we hadn’t seen before. So really what we were seeing was people being able to post stuff on the internet, when before it was super tricky unless you were a programmer and also very expensive. And meanwhile, we were living in Peru where we saw that every, single person was online but every website that they went to, somebody had created it from a different country. So our initial idea was to build open source websites, particularly using open source content management systems, so that people locally—particularly non-profits—could make websites and talk about their work. So we started there and that was kind of the very, very, very early days of Development Seed. We shortly thereafter ran out of money and moved back to Washington, DC, picked up another co-founder—Ian Ward—who stayed in Peru and—but then we started working with international development organizations. And that was—really like for me kind of how we started with Development Seed. I came on full time after the company had been up and running for…about three years? We worked with these international development organizations—at first we were just building them websites, but then we quickly started specializing and doing a lot of work with data visualizations, content management systems, like I said, internets back when that was a thing. And yeah, and we were slowly growing a team. And really what we realized as we were doing this was that we were hiring people who were very interested in building very cool technology, which is not really where you excel in the consulting game where a lot of what you want to do is build replicable technology so that you can—you know—spit it out very quickly. So we just kept trying to sell new things and we built new things and got better and better at doing that. Which was really fun, we built a name for ourselves. And then we had two different runs at doing—at making products. Both were moderately successful in that we sold them both but then also our third product that we tried building as Development Seed was what turned into Mapbox. So that was—our clients needed maps. And our clients were working in places like Africa and Haiti and—you know—the Middle East, Afghanistan. And at the time, the maps that existed online—it was just Google—there weren’t any maps of those places. It was maybe you would see a capital on a map, so we had to figure out how to actually put street maps up there. A lot of the work we were doing was humanitarian relief, so people getting from point A to point B was super important. So we figured out how to make maps—a lot of that was through convincing—you know—countries to give us their data, which was surprisingly easy to do. We hired some interns to help us with that. And then we had to figure out how to put it online—that was much more complex. But that need that we saw from our international development clients and this is—you know—the Red Cross, World Bank, that was really what kind of helped us come up with the idea of Mapbox and build the basis for it.

[20:56]

KL It’s so cool when you hear about people solving real problems and real life challenges where—I mean—were you able to see sort of the positive results of that?

BB So yes and no. I would say it was one of those that we could see the possibility for the positive results of it but that was also kind of what ended up being a bit of the slog of the consulting work that we were doing was that we were building these—these tools that we thought honestly could solve these problems. I mean—you know—famine in Africa—you know—delivering supplies after earthquakes in Pakistan. And we saw the potential but we weren’t always seeing—either we didn’t get any information back on how people were using it or the information that we did get back showed that the government pays a lot more money in order to build products than to fund their use. So that was something that was—honestly kind of pushed us even further into not wanting to do consulting work and really wanting to focus on our product. Because we loved the—the mission of what we were working on was something that was very important to us. But honestly it gets super draining when you see that what you’re building, what you’re pouring hours into, what you’re working for like sub market rates at in order to be able to put this thing out there and then to see it not used…I think we all saw that—went through that. And that’s just part of how the world works—I understand that. But it was one of those things too that tipped us over. We’re like, “yeah, doing our own product, that could be cool, that could be something that’s up our alley.”

KL Right, because you have real control over it.

BB Exactly.

KL So you started Mapbox with your then-husband and you were in the process of splitting up, right?

BB Yes. So it was me and my ex-husband and there was a few other people that we all kind of deemed ourselves as cofounders of Mapbox. And timing was interesting because we had our first like big win with Mapbox in 2012 when Foursquare started using us.

KL Yeah.

BB And that then kind of then launched us into this “okay, maybe this can be something.” And we decided to go for it, we actually had a bit of a team vote about it, there was about ten of us in the room that said okay, let’s go for VC funding, it’s the only way we’re going to blow this up and really compete. And yeah—and then a few months after that was when me and my ex-husband—we decided to split up.

SWB That sounds super hard! How did you get through that period of like exciting professional stuff happening, big things, big decisions to be made, while also dealing with really hard personal stuff?

BB So, I got together with my ex husband when we were in college, we were juniors in college. It was my first big relationship, so it was also my first big break up, so I had no idea how to do that either so that was a nice complicating factor in the midst of all this too. I think at that point because we had been working together for so long, we were both decent at compartmentalizing personal and professional, so that was helpful. We also didn’t tell anyone at first, which was helpful in that nobody talked about personal stuff at work in regards to us splitting up because no one else knew. So I could go into this—you know, both of us could go into this safe spot where it wasn’t going to be like—you know—you got the pity eyes or whatever it may be that could throw you off your game. So we did some things to protect ourselves and we did that for a while. But honestly for months, I was really on the fence of “is this a place that I can stay” and it took me a while to get past that. And a lot of that was trying to figure out, can I work on this thing that I want to knowing that it means that life will be as us as two individuals and not as us as a couple? And when we did finally tell a few people—the other cofounders—they all basically said, like, “we can’t do this without you.” And that was this reaffirming thing for me that was really helpful. So it was a lot of reassurance from my coworkers that built up my confidence enough to be like—and also just talking with my ex—to be like, who cares if this is super unusual? And yeah, we’re getting a divorce, and we’re starting a company together at the same time, and screw it! You know? [SWB and KL laugh] Like, let’s just do it. We both want this.

SWB Kudos—kudos to you! Because I feel like I am so much pettier [KL laughs] than that and I would like to think I would be the kind of person who could handle it and like I am not confident I am that person.
[25:01]

KL Well, speaking of—you know—sort of stepping into that role and not necessarily having a traditional background in business, was it hard to figure everything out?

BB So I wasn’t the one that went after our funding, so I wasn’t the one pitching, which I think was—was good, that’s not that something I think I’d be particularly good at. I didn’t have the pressure of that and also the rejection of that right as I was going through a divorce, thank god. But I had the supporting of the company on the backend. So really what it was was trying to figure out how to not only create this new company and figure out how to get it set up so that we could actually take on VC money, while at the same time running the other company—Development Seed—to make sure that we could actually pay our bills and pay our team. So it was almost like I had two full time jobs during that time, one of which I had been doing for a while, so knew what to do and one of which I had absolutely no idea what to do but that was the future, and so if I screwed that one up, we were all done. [SWB & KL laugh quietly] I also had both the curse and the luxury of knowing exactly how much money we had in the bank and when we were running out of it.

KL Yeah.

BB And we had a lot to get done. And it was a good time overall too for—like I dove into work harder than I ever had before and that was probably just what I needed. I had something to focus on and we got a lot done and we were building this thing that was about to be so exciting.

KL Did your role sort of ever change or evolve—I mean I’m sure it did—but in context of Mapbox growing because it sounds like it grew quickly and big.

BB So, yeah, I mean my role definitely changed and a lot of that happened honestly overnight with funding in that basically when funding hit, not only was I doing all of the running the company, running operations behind it and just really everything on kind of the backend of the house. But then also we had this opportunity for the first time where we could really figure out how we wanted to grow and we knew that we were going to grow quickly, we knew we were going to double in size as far as team size. But also we had—we had money for the first time. We had never had any money before, we always had like maybe two months in the bank. So that was this freedom of we could do it the right way because we had resources and we were very lucky in that we had investors who were supportive of us as well. So really it was a lot of—at that time—was a lot of envisioning of who we wanted to be when we grew up, as a company. And something that was important to me and to the other co-founders as well was creating a business that was a place that we were very proud of, a place that we wanted to work and that—you know—had the values that we wanted to put forth. And yeah, we wanted to build an environment where everybody could thrive and felt supported and had space to do what they thought was best for the company. And that was a lot of my job was trying to figure out how to create the foundation of a company that we could be proud of and then how to grow that and have that not break as we grew as fast as possible.

SWB So I know that Mapbox has grown a ton and it’s become—you know—a pretty good sized company but also you left the company relatively recently, right? So can you tell us about that? What was it like to grow this thing and then make an exit and what made you decide to do that?

BB So I was there—I left about a year and a half ago. And I helped grow the company from 0 to about 225 people. I had been working with the combination of Development Seed and Mapbox—for ten years, so I hit my ten year work anniversary and that was a nice pause for reflection. You know, I mean, I can’t tell you how much I grew based on the opportunities I had career-wise, but also I worked with the same leadership the entire time. And essentially I mean, like I didn’t really have a boss but if I did, it would be the same group of people being my boss. And that felt like a lot. And I had also hit this point where growing a company is very, there are so many interesting things about it, but it was almost like at that point, I was—we were past some of the building stage. Obviously everything’s still growing and building—now too—but I was doing a lot of the things again or for the second or third iteration on them. Which was necessary, because there was the thinking through of how do you do this for a larger company. But it was almost like I was solving the same problem. So it was really fun to come up with our onboarding plan for our team and how we best brought on new hires the first and second time, but doing it the fifth time, that wasn’t really fun anymore. And I was able to pass off, obviously, a lot of work as my team grew, but it was also not really…I wasn’t sure if it was exactly giving me what I wanted career-wise overall. We were also going through this transition internally at Mapbox where we had started as a flat company, which worked really well for us for longer than I—honestly than anyone ever thought it would. But we were coming up on the point where that absolutely had to change, it was no longer working and we were talking through how to fix that. So, a lot of the internal debate at that point was whether or not we were going to—like how to put in management structure. And a lot of what went with that was a lot of the systems and work that I had built over the years. So it was time to change but I wasn’t—frankly, I wasn’t winning the argument on how to do that. Meanwhile, we were also having the conversation about what was next for the company where we were discussing basically like do we go for another round of funding? And the answer to that was yes. We decided to go for as much funding as we possibly could, but then I knew that that was another three- to four-year commitment of running as fast as possible. At this time I was splitting my time between San Francisco and DC, so like personally the toll of doing that was pretty heavy. In the beginning it was so much fun, but after three, four years I was exhausted all the time and I missed having a life in a single city. Yeah and it just seemed like all these factors were kind of combining together so that it meant that it was—it was a good time for me to leave, it was good for me personally because I would get a break. I could try something else out new career-wise, which I was hungry for, and also company-wise it would give the company a fresh start, as we were doing kind of like a massive cultural and internal organizational change for me to be able to step away and so it wasn’t like “that was the old way under Bonnie and this is the new way under—you know—Series C, this is what this looks like.
[30:55]

KL Yeah. Well now you are the director at Brazen, where you’ve been launching the Philly office. Tell us more about Brazen and what you’re doing there.

BB Sure. So I started with Brazen beginning of the year and really what we want to do is help women entrepreneurs grow their companies. So we work with people who are doing startups like high-growth startups, which—you know—like Mapbox and other ones. But also people who are just trying to go from being the only person at their company to hiring four people, five people. So really going after some of the small business pieces too. And we focus on the operational pieces on like how do you actually do like that? And these common questions that everyone has who is running a business—you know—like how do I hire, how do I—financially how do I plan for this? Legally what do I do? How does this work? What is—you know—when do I go after financing? So that’s kind of like our bread and butter is focusing in on those things, which is really interesting for me and what really drew me to it because that was all the stuff that I had to learn as I was going through my work with Development Seed and Mapbox and which I had no idea what I was really doing with up until I had done it. And it’s a steep learning curve, it is for everybody. So kind of like Brazen, our goal is in order to kind of help people with those tangible questions that they have as they’re going through it, but also connect them with other entrepreneurs so they have people to ask questions to. I know when I was—when we were getting Development Seed off the ground and I felt completely over my head all the time on—you know—like oh how do we run a business, I don’t know I’ve—you know—I’ve never done this before. All my friends were working nine to fives and whenever—you know—I would talk about work, they’d roll their eyes at me. [KL laughs] They’ve gotten much better about that over the years, but our idea with Brazen is to fill that need for people.

KL I love that this exists.

BB Yeah, thanks! I think as a resource it’s really helpful. It’s something that I—looking back, I wish I had had access to.

KL How has it been working for a company that’s already established versus running your own thing?

BB Yeah I mean it’s a lot of—like asking for permission is something that I haven’t had to do in over—you know—basically my entire career. So that part has been strange and I’m—and I’m—frankly, I just don’t really ask for permission. I just go out and do stuff and if it works, it works. And it’s been—it’s been good. Like it’s—Brazen has a startup mentally, so that’s great. And it is interesting not carrying the stress of it too because that was something that I’ve also had for so long that I really I wanted a break from. And that was really important as I was thinking about what I wanted next career wise, so yeah, I mean that part’s been nice. Like I stop work when I eat dinner and then I don’t normally go back online unless there’s—you know—unless I’m excited about something.

KL Yeah, I totally get that. And I think it’s really nice when you can kind of take a step back and—and see what you’re missing in your current situation and say like “okay, this is the thing I need to move to next.” So, you are also expecting a child soon, right?

BB Yes! In October.

KL That’s so exciting, congratulations!

BB Thank you.

KL I’m sure that that has also something that you’re considering in terms of what you’re working on now and—you know—what’s next for you.

BB Oh, definitely. And I—and I feel like I’m in this funny spot where—and this kind of fits my personality—but where I did—you know—last year I did this full life pivot where I left Mapbox, I had been living in DC for—since college. So that was about eighteen years and I decided hey I’m going to quit my job, leave the company I helped start and move to Philadelphia where I don’t know anyone—except unless I went to high school with them or they’re related to me. And my boyfriend. But it was a big change and part—I mean, it was something I wanted to do for a long time but also I really wanted to focus on my personal life because I had done a crap job of that for a long time. So particularly after like when Mapbox started and got full up and steam, I—I worked. That’s what I did. And I loved my job, I loved what I was doing, so that was—that was fine. But it was—it was fine for a moment in time and I was ready for something different. And then now I feel like it’s—I’ve gone like swung completely to the other extreme because now we’re having a baby soon! And we just recently bought a house in the suburbs and have this master plan of splitting our time between living in Philadelphia in the city and then being out in the suburbs because—to be closer to my boyfriend’s two kids. And I own a car now for the first time since I was in high school [KL laughs] and everything has shifted drastically in the other direction, which is both really exciting and also confusing sometimes. [laughs]

[35:10]

KL So, I’ve just got one last question for you. If you were to—you know—tell someone who was looking to start a company or something just wildly new, do you have any sort of advice that you would give them based on all of the kind of amazing experiences that you’ve had?

BB Don’t think twice. Just—if someone has the itch to go do their own thing, I always tell them to do it, to try it. Because otherwise you’re going to overthink things. When really, starting your own business is more about getting stuff done and getting out there, even when you have no idea if what you’re doing makes any sense. Because then as soon as something is out here, you can make it better, you can fix it, and you can get reactions to it. But it becomes real once you get started. So yeah, I mean I think that would be my biggest piece of advice is go for it. You know obviously it’s always good to think through financially to make sure you’re in a good spot and all those things, but if you can, take the—take the jump. It’s an exciting ride. You’re going to learn more than you ever will working for somebody else, just because of the amount of pressure and the amount of risk that you’re going to be taking yourself. And even if it doesn’t work out, then—you know you took the plunge and went for it and you can go back to doing what you were doing before.

KL Yeah, I love that.

SWB And maybe some of our listeners would be interested in getting some guidance and support from a community like Brazen!

BB Yes! That would be awesome! So Brazen—we are in six cities now, Philadelphia being one of them but also in Chicago, Saint Louis, Detroit, Denver and Dallas. So, if you’re in any of those areas, check us out.

KL That’s so great. Thank you so much, Bonnie, for joining us today. It was really, really lovely to talk to you.

BB Oh wonderful to talk to you! [music fades in, plays alone for five seconds, and fades out]

Career Chat

[Ad spot]

SWB It was so cool to talk to Bonnie about knowing when it’s time to make a change. And speaking of career change…it’s time for our weekly career chat with Shopify. What do we have this week, Katel?

KL Well, I was looking at Shopify’s job listings, and I found one for a Product Operations Manager, where they’re looking for someone who can be a team player, coach, and referee all-in-one. I love this because I know a lot of folks like who have this skill—and it’s so critical to being a manager!

SWB Totally! And, you know, one of the things I really love about Shopify’s job listings is that they’re not overly prescriptive, like you must have 5+ years of X, or you must have a bachelor’s degree. They just feel a little more human. Like check out this one for the Director of Partnerships in Channels. They’re looking for “a senior strategy and business leader” and you’d be doing stuff like developing strategic relationships, or improving product integrations, or building teams across different offices. But then at the bottom of the posting, it says: “Experience comes in many forms, many skills are transferable, and passion goes a long way.” And they go on to talk about that if your experience is close to what they’re looking for, that you should consider applying even if you’re not an exact perfect match to everything that they list. And I think that’s so great.

KL I love that. SO. If you want to solve problems you’re passionate about and work with a team that’s making commerce better for everyone, visit Shopify.com/careers to see which role might be right for you! [music fades in, plays alone for five seconds, and fades out]

FYOTW

KL So, I’ve got a fuck yeah to share. So last night, I hosted about twenty women and two men from a volunteer group that I work with here in Philly. And it was really cool, we don’t meet up that often and so we all got to hang out and it was great. And we had someone giving a presentation and it was great—super informative. And she brought her one year old baby with her so she was—you know—giving her presentation, the baby was hanging out and she started to get a little uncomfortable at a certain point, kind of fussy. And so mid-sentence, the woman who was talking just looks up at the room and says “does anyone mind if I breastfeed?” And this is a group of people who, if you’re going to breastfeed in front of twenty some odd people, this is the group to do it in. And so we all just started laughing because we were just shouting like “yes of course, oh my gosh.” You know, in this group, of course do that. So it was really cool and it just made me think I was so glad to be in that room and be a part of it, but I was also like “fuck yeah, she should be able to do that wherever!”

JL Also fuck yeah for hosting [laughing] twenty-two people in your house!

KL [laughing] Thank you, thank you.

JL Because, impressive. But it’s great that we can feel this way, but I hate that we even have to feel this way.

KL Yeah.

JL Like there shouldn’t even be a question like “does anyone mind if I breastfeed?” or even, like, the hesitation. People should all be able to feed their children wherever and however they want to at all times.

SWB Totally! I think like fucking breastfeed everywhere, anywhere. Like kid’s got to eat, it’s not a big deal, people breastfeed, it’s not a big deal. Something that I saw recently was that there’s a lot more emphasis on people breastfeeding in public spaces. In fact, really public spaces. Did you all see back in the summer—I think it was in June—there was a member of Parliament in Canada who took a quick break to breastfeed her son right during the middle of Parliament.

[40:00]

KL I love that.

JL Yeah, and the year before—Larissa Waters in Australia also breastfed in Parliament. And the more that people do it, the more it gets normalized. And it sucks that we have to normalize it, but we do because [laughs] people have such strong, uncomfortable feelings to it, which makes me really upset. You know—I was just thinking—you know—maybe we need to create a Foursquare for breastfeeding. [KL laughs]

SWB Like a breastfeeding scavenger hunt where it’s like [laughing] you have to breastfeed in this whole list of places and you win some prizes.

JL Yeah I mean, it’s like one of those things. Like as you know, I breastfed my son. And when I first starting breastfeeding, I did personally feel uncomfortable breastfeeding in public. Luckily, I have the support of a lot of friends and I’d like—you know—mention these groups, which are great if you don’t have other mothers that you’re close to if you’re looking for a thing, there’s breastfeeding support groups online that are—that are awesome at this that will help give the confidence so that you don’t feel like you ever have to ask “can I breastfeed” because you shouldn’t. You should go into a restaurant, a park, if you [laughs] have to be at some sort of meeting with your child for some reason, you should be able to feel comfortable to be able to breastfeed your child there and without even ask or hesitation and no one should feel weird about it because that’s just—you know—what we do.

SWB Totally! And I do think—you know—if you feel uncomfortable breastfeeding in certain scenarios or if you feel a little more private about your body, that’s totally fine—right?

JL Yeah, sure!

SWB This is not about pressuring anybody to do things that make them uncomfortable, but it’s about the ways in which we feel like we can’t do a thing that we should be able to do because other people are going to think it’s weird or shame us or make some nasty comment. I remember when I was on a city bus in Germany with my sister-in-law who was breastfeeding their baby. So—you know—she just lifts up her shirt and starts breastfeeding in the middle of the city bus. And I remember I asked her—you know, her and I are close—and I asked her, what was it like to get comfortable doing that? Was that something that you immediately felt comfortable doing, or did it take a while, and how did you get comfortable doing it? And she said it was a little bit weird at first, but she said, like, really it was within a week or two of just being like “gotta feed this baby”—right? Your priorities all shift around and she’s like “baby is hungry, need to feed baby” like you just—you just sort of normalize it very quickly. And—you know—they’re lucky enough to live in a place where I don’t think she gets a lot of flack for that in Eugene, Oregon. [laughs] But in other places that’s not true—people will say something to you and like…no, don’t ever do that.

JL And, you know, just to re-emphasize, if breastfeeding in public is not something you want to do—I mean, certainly don’t do it. But anyone who does want to do it or needs to do it, you know, should be able to without any judgement. And I think it’s up to all of us to provide those supportive spaces—you know? I shouldn’t have to go up to someone and be like “well, would you rather see my child breastfeeding or hear him cry?” There should never have to be that statement. I shouldn’t have to convince anyone of this. And so I think it’s, one, being accepting but also—you know—if you do see those people who are judging, tell them a little bit more about why this is okay. So, fuck yeah to breastfeeding in all places that you feel comfortable breastfeeding.

SWB Fuck yeah! Well, that is it for this week’s episode of No, You Go, the show about being ambitious—and sticking together. NYG is recorded in our home city of Philadelphia and produced by Steph Colbourn. Our theme music is by the Diaphone. Thanks to Bonnie Bogle for being our guest today.

KL If you loved today’s show as much as we did, don’t forget to subscribe and rate us on Apple Podcasts, or wherever you listen to your favorite shows. Your support helps us do what we do, and we love that! See you again next week!

[Music fades in, plays alone for 32 seconds, and fades out to end.]


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Welcome to Strong Feelings

Best friends and business partners Katel and Sara let it all out in a weekly show about work, friendship, and feminism. Because life’s too short to bottle things up.
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