How I Got Here: Episode #7

Mike (00:06):

Welcome to How I Got Here, a podcast from The Garage at Northwestern, exploring interesting journeys of young professionals working at exciting companies. And the role that entrepreneurship played in getting them there. My name is Mike Raab, and I love dissecting nonlinear and non-traditional career paths and the lessons that we can all take away from those who forged them. In this episode, I’m joined by Rachel Cantor, the head writer of Sidekick, a newsletter from Morning Brew that curates recommendations around smarter living. A job she landed, believe it or not, by tagging the company in a tweet. Since she was a teenager, Rachel has followed her curiosity down many paths, including starting an online news source For Teens, By Teens as a high schooler, running the largest student organization at her university, and starting her own personal recommendation newsletter. In this conversation we discuss the benefits of following your curiosity, how Rachel thinks about entrepreneurship, and why sharing your work publicly can lead to unpredictable outcomes. I hope you enjoy this conversation with Rachel Cantor. All right. Well, Rachel, thank you so much for being here with us today.

Rachel (01:16):

Thanks for having me.

Mike (01:17):

Of course. So typically I usually start these conversations when you’re entering freshman year of college, but you were actually a pretty tenacious high schooler as well. Can you tell me about what the Daughter was and how that got started?

Rachel (01:32):

Yeah, so I attended a summer program after my freshman year of high school. I think it was my freshman year. It was about social entrepreneurship and I kind of fell in love with this idea of starting a business that does good in the world. Tom’s really pioneered that model. I was really into it. And so one of my friends and I, we thought it would be a good idea to start a business together, focus on something we were passionate about, which was teens feeling, being informed about the news. We felt like we knew what was going on in the world, but our peers didn’t. And the news wasn’t as accessible. I mean, now we have great newsletters. We have lots of sites that kind of distill things down, but we felt like the Wall Street Journal, the New York Times, things that students were reading weren’t really reaching them. So we started an online news source by teens, written by teens from all over the world, called The Daughter. And I started that my sophomore year and led it throughout high school.

Mike (02:35):

And so throughout your kind of time working on that in high school, I guess, had you planned to continue working on that in college, and kind of how big did you scale it or how many people were working on it?

Rachel (02:47):

Yeah, so we had a team of about, what was it, me and my friend running it, the co-founders, and then we had a bunch of writers. I don’t remember how many, but I do know that we had over 12 countries represented then. And we had writers from all different states and I just recruited them from reaching out to summer journalism programs and also a bunch of high schools and where I was from, where she was from.

Mike (03:12):

What do you say your biggest kind of learning or takeaway from that experience would be?

Rachel (03:16):

My biggest takeaway is that for me personally I really learned that I love to do my own thing and just create and build things. And I didn’t realize how young people can actually do pretty cool things. I know that sounds simple to say, and yeah, young people can do pretty cool things, but it really didn’t take that much work to reach out to a bunch of clubs, recruit students. And then that was an opportunity for them to showcase their work, put it out in the world, and then also practice their journalism skills and writing skills and put them to use. And I loved building that with my friend and every day was different. I learned how to code a Squarespace website. I learned what it means to do cold outreach. I reached out to a bunch of bloggers around that time to learn from them. And I think after that I was like, “Okay, I really have this desire to build and create things and I want to make that a big part of my life.”

Mike (04:17):

Yeah, I think that first experience that you have agency in the world or that you can create something that other people are interested in, is really important.

Rachel (04:26):

So important. And it didn’t work out, the startup, but I learned so much from that falling apart too.

Mike (04:33):

Right, you wouldn’t go back and not do it just because it didn’t ultimately succeed.

Rachel (04:36):

Exactly.

Mike (04:38):

Right, so you have this kind of experience with entrepreneurship as a high school student. When you’re entering college, what is it that you choose to study and what do you think you’re going to do after school eventually?

Rachel (04:50):

I chose to study communications. I was always passionate about marketing. My dad works in marketing, so I kind of grew up in this agency environment and I loved the creativity and the idea that you could understand a brand and then create campaigns around that and create a brand voice. So I was passionate about marketing, passionate about media, chose the communication studies major at Northwestern and pursued that all the way through college. And so because my dad had that agency experience and that’s what I really knew, I thought that for me to launch my career in marketing, that going the agency route was kind of the best thing to do. So I joined a student run marketing agency and was a part of that for three years. And then I kind of had this moment in college where I remembered what I built in high school, and then also got involved in some other things at Northwestern and realized that, “Oh, I can flex that marketing mindset, but do it at a startup or my own company, and kind of combine my two passions for marketing and entrepreneurship.”

Mike (05:57):

Right, makes sense. So it sounds like originally the agency was kind of like the North Star of the goal, but as you have these other experiences. And maybe you can talk a bit about either internships or other jobs or student projects or organizations you worked on, you realize that an agency might not be the most exciting thing for you, but that there was another way to get kind of marketing experience?

Rachel (06:20):

For sure. And my first internship in college was at Refinery29. I had this really cool opportunity I could not pass up. At the time Refinery was my dream company. I used to read it every day before high school. I read it in college, and I had this opportunity to go work in video, which was something I had no experience doing at all, and go learn there. And so that was my first time dipping my toes into media, and also working at a company that was very developed, but also very scrappy at the same time. And I liked the challenger mentality there, where I could take on projects on my own, even though it was such a big company, and I also loved that it was built by women and I was surrounded by women. And I realized that was really important to me, either to work for female founders or be surrounded by passionate, inspiring women. And I loved that experience. But then after that was like, no way am I going into video at all. And never thought I would be in media. And after that-

Mike (07:29):

I want to just hit pause for a second because it’s a super cool story how you got that opportunity in the first place. You were like a 17-year-old at a business conference or something. How did you get the Refinery29 experience?

Rachel (07:44):

When I was a senior, Fast Company, which is a great magazine about business, about startups, entrepreneurs, they launched a big conference called the Fast Company Innovation Festival. And it was the first year they were ever doing it. It was in New York City and it was basically a lineup of amazing speakers and then site visits to companies all over New York. So it was like the founders of Warby Parker and Birchbox, and then site visits to Refinery29, Adobe, Eileen Fisher, who was doing cool things in sustainability. So I was like, “This is the coolest thing ever, I want to go.” And I found a way to get a ticket, make my way to New York. And then it was funny, a week before the conference they were like, “You’re 17 and we have alcohol sponsors, so you need to be chaperoned.” So my mom came with me and they’re like, “We’ll give her a ticket.”

Rachel (08:40):

And I went to New York, I went to Refinery29 and I listened to this talk from the chief content officer about the future of video and what Refinery29 was doing to innovate in that space. And then afterwards I approached her just asking a question. I don’t remember what the question was, but she looked at my name tag and looked at me and she was like, “You look so young. What is a 17-year-old doing at this business conference?” I was like, “Well, I’m just really excited about what you guys are doing. I just want to learn about this. This is the kind of space I want to be in.” And she took me on a private tour of the office, introduced me to all these people who were like celebrities to me. And then at the end of it, she was like, “You should intern here. Would you like an internship?” And that’s how I got it.

Mike (09:30):

That’s amazing. And I think we’re seeing examples of, it seems like you’re unafraid to put yourself out there or reach out to someone or ask a question, or like you said, reaching out to other journalism programs to see if they want to write for you. Where do you think that confidence or brazenness or whatever you want to call it comes from?

Rachel (09:52):

Honestly, I think it’s just my curiosity. I’m very curious about a lot of different things. And I just ask questions and I think when people are asked questions, when they notice people are taking interest in them or what they’re doing, they’re really receptive to it and excited about young people who are interested in similar things or interested in the space. And it’s funny, those moments can be the scariest, like approaching someone really high up at a company you love and you’re 17, but after you do it, it usually pays off. At least that’s kind of how I ended up in my current role. And a lot of like the learnings I got from my time at Northwestern.

Mike (10:32):

Right. You’ve got nothing to lose.

Rachel (10:34):

Exactly. What’s the worst case? They say no.

Mike (10:37):

And I also find that the more you do it, the more comfortable you are doing it.

Rachel (10:41):

Over time you just flex that muscle.

Mike (10:44):

Totally. Okay, so you had this internship in kind of media and content at Refinery29, maybe it shifts your perspective of agencies. What were some of the other experiences that you had as a student that kind of changed your mind?

Rachel (10:58):

I participated in The Garage’s 10-week summer program wildfire, working on a student run startup there. And then I ended up interning at a marketing agency, which is where I really made the decision where I would not at all pursue that path. But I think one of the biggest learnings I had was my senior year. I ran the largest student run organization at Northwestern, which is Northwestern’s Dance Marathon. It involves over a 1,000 students every year. The organization fundraises a lot of money. And I oversaw 20 people on an executive board, selected a beneficiary, did a bunch of different things, almost like a CEO would do. And I learned so much from that experience, just managing people, but also building an organization and also applying that startup mentality to a student org. Because it was a 46-year-old, I guess, now 47 or 48-year-old organization. And it’s like, how do you build upon what’s been done in the past and innovate to really create change?

Mike (12:07):

Yeah. And so I’m curious, you had this experience working with a startup at The Garage, you worked with a couple of different teams, I think, but like you mentioned, you’re also trying to be entrepreneurial with the student organization that you’re managing. How do you think about what, or how would you describe what entrepreneurship is and how you apply it?

Rachel (12:27):

Yeah, so I used to think that entrepreneurship was all about starting a company. That’s kind of how I used to define it. And then when I had the fellowship at The Garage, which is the Little Joe Ventures Fellowship, basically all about supporting entrepreneurship at an undergraduate level. There were five of us selected our sophomore year. And then our junior year we took a trip to LA and learn from entrepreneurs, visited companies. And there was an entrepreneur, Dr. Sam Prince and he said, “Entrepreneurship is not an identity, it’s an activity.” And that was the biggest aha moment for me because I realized, “Oh, I don’t have to start a company in college to be an entrepreneur. I can really just apply that mindset.” It’s really a mindset to anything and everything I do. And that can be running a student org. That can be what I do in my current role now. It can be how you approach learning in the classroom. It applies everywhere.

Mike (13:30):

I love that from Sam Prince, because I think tying your identity to anything, especially if it’s like a startup can be very dangerous if it fails.

Rachel (13:38):

For sure.                                                 

Mike (13:40):

And or if you desire to “be an entrepreneur” but don’t feel like you’re making any progress. Like if you have imposter syndrome around that.

Rachel (13:50):

Definitely, it totally changed everything for me and really is how I apply or how I approach everything now.

Mike (14:00):

Yep, and so you had the experience at the marketing agency and realized that wasn’t for you, but it sounds like at this point you’ve collected a bunch of different experiences and perspectives. I’m curious how you were thinking about, because you know, I think typically students kind of go down a very specialist path and each summer take a more serious internship that’s deeper. How are you thinking about being a specialist versus a generalist, both as a student, but also looking forward in your career.

Rachel (14:32):

Yeah. I mean, I’m very much of the mentality of being a generalist rather than a specialist. Or at least when you start out I think being a generalist is the best thing you can do. I know people who’ve always said, “Take a linear path, you do X, Y, and Z to get to this place.” And for me, I honestly really know what I wanted to do. I had this idea of working at a fast growing startup in marketing, but one, I didn’t really know how to get there. And two, when you work at a startup, you have to wear a lot of different hats. And I think it’s helpful to understand all parts of the business, whether it’s from content to business operations, to strategy. So anytime there was an opportunity I was excited about, I just pursued that. And that’s what I tell people is, “I think you should just follow what you’re curious about and also what you want to learn.”

Mike (15:26):

Yeah, I think that matches what you said earlier about your just kind of inherent curiosity about the world and different things really well. And so, you’re starting to get more exposure to entrepreneurship and startups, and I believe you took kind of a career trek out to San Francisco at one point.

Rachel (15:44):

Yeah.

Mike (15:44):

Can you describe that and any kind of thoughts that you had after that trip?

Rachel (15:48):

Yeah so I went to a bunch of different tech companies in San Francisco with Northwestern, right before my senior year. And we went to all different companies from LinkedIn to, I think, a startup that just raised like a series A, to Lyft, to Facebook. And I saw these big companies and it’s definitely impressive what they’re doing and the free lunch and all of those perks are really attractive. But to me, I realized that I want to have a bigger impact, and to do that, to really see your work come to life and be an entrepreneur and build things. I think it’s best, at least it was best for me to start at a smaller scale. And that’s when I really sat on this idea of a startup that maybe isn’t at square one, but is on its way and growing really fast.

Mike (16:41):

Yeah, makes a lot of sense why you would want to go work at it kind of a smaller startup and have a bigger impact. So, you mentioned that was kind of before your senior year, and communications majors typically don’t go through the formal recruitment process in the fall that some econ majors will. So how were you thinking at that point kind of beginning of your senior year about your job search for what you would do after school?

Rachel (17:05):

Yeah, so I started looking for jobs in the fall, and then, like you said, quickly realized that the jobs I was really looking for didn’t really come out until the spring. And I always think that’s really hard for people who want to pursue creative careers, because you see your friends taking these finance or consulting jobs and they’ve secured them in the fall, and sometimes even right after their summer internship. And it’s hard to be struggling on that path while people have so much security. But I knew that what I was looking for would come out much later in the year. So I just did, I just learned what I could, talked to as many people as I could, and really learned from their experiences, and planned on starting that process much later in the year towards the end of winter/spring. But then COVID changed everything kind of, but I still continue to have those conversations and still discover what I actually wanted to do.

Mike (18:08):

Hopefully some of that flexibility and adaptability of your entrepreneurial mindset were helpful when COVID hit?

Rachel (18:15):

Yes.

Mike (18:17):

How did you eventually get hooked up with your current role at Morning Brew?

Rachel (18:21):

So, when everything happened last March and quarantine began, I was in that process of figuring out what I would do post-grad, talking to a bunch of people, networking, applying to jobs. And while I was doing that, I was really interested in starting some kind of project. I’ve always been that go-to friend for recommendations, whether it’s podcasts, books. I love talking about direct to consumer brands, so brands like that. And I honestly just thought it would be cool to put all of my recommendations in one place and centralize them in a newsletter. So I launched a weekly newsletter with my own personal recommendations. I started with a small audience. It was about 50 people. I grew it really quickly and continued to write every single week. And from there landed a freelance writing job at a sustainable startup in San Francisco called Brightly, which is actually like kind of a mini Refinery29, but of sustainability. And started writing their newsletter and creating a new revenue stream from that newsletter for them.

Mike (19:35):

So I want to dive into a couple of things here, but the first is you mentioned you kind of started with a small audience and grew it. Was that natural growth where you, buying advertisements, how did you kind of grow your newsletter? And then yeah, secondarily for the Brightly kind of freelance writing opportunity, did they come to you? Did you seek them out? How did that opportunity come about?

Rachel (19:59):

I grew my audience for my newsletter completely organically. I started, the first post I ever did was an Instagram story, and that’s how I got my first following. And then I posted about it on Facebook and those were the initial subscribers. And then I kept writing every week and then my friends would pass it along too, and it was like I said, kind of just a side project that I didn’t really think would turn into anything. And at first I really wasn’t sure if I wanted it to be anything, but then when it started growing really quickly and I realized how much value it was adding to people’s lives, I was interested in actually investing time in growing it.

Rachel (20:44):

And I had a conversation with a blogger from Chicago who is a friend of mine. She’s really active on Instagram and does a lot of paid partnerships, and I really value her advice. And I reached out to her and said, “I want to grow my newsletter. I don’t really know what that looks like.” And she’s such an expert at growing her brand and her blog. So I looked at her and she was a subscriber of my newsletter. And she said, “You know, Rachel, what you’re doing is actually really creating value for people.” And that was the moment where I totally shift my mindset about self-promotion. I think self-promotion can come across as like bragging. And that’s why I really didn’t want to promote my newsletter. I’m just, I’m not that type of person and I didn’t want to post all the time on social media about it. But then when she told me to look at it differently and see how the work that I was putting out was actually creating value, I started creating regular Instagram story graphics and posting them on my account. And that consistency along with my friends posting those graphics, sending them to their friends, who sent it to their friends and all of them posting, grew to a much larger audience.

Rachel (22:05):

And then even on LinkedIn there were posts too, like The Garage posted about the newsletter I wrote. And that led to a bunch of really interesting people subscribing to my newsletter. There was the chief people officer at eBay who subscribed to my newsletter, which was very random, but super cool. And then it was actually through that Garage posts that I got introduced to Brightly and the founders reached out to me directly.

Mike (22:32):

That’s amazing. It sounds like this would be such an energizing experience to have it kind of growing organically and people excited. And like you said, you’re creating real value for them. So what was the experience of kind of being a freelance writer for Brightly like? And how did that eventually lead into your current role at Morning Brew?

Rachel (22:54):

So being a freelancer is interesting, because you are your own company, you are an entrepreneur basically. So it was, creating a schedule for myself that worked. It was cool because they introduced me to a bunch of people at the company. And I sat in on all of the all hands meetings, just because it was helpful for me to understand what was going on so that I could apply that to the newsletter. But I learned a lot about what it takes again to run a fast growing startup. And then also learned that I liked this creative pursuit of writing, which I’ve never thought would be a career for me. I’ve always loved writing. It’s always been a big part of my life, but I didn’t think that I would pursue it as a full-time career. And it was only when I started creating my newsletter and writing for Brightly that I realized that one of my greatest strengths is not only the writing, but the actual curation that comes with it.

Rachel (23:49):

There’s a true art and science to it. And I it’s always been something I’ve done, but I did not realize that it was a career path. And so when I put together my weekly newsletter, which I was doing on top of writing for Brightly, there was a link from Morning Brew that I included. It was their Mad Libs. They made these really fun Mad Libs during the summer. I put them in my newsletter and then kind of channeling that self-promotion I was talking about earlier, I threw out a tweet, very random tweet with a link to my newsletter and then tagged three brands. It was Morning Brew, the host of a podcast, and then a local Chicago business. And just put it out there. Maybe someone would like it. Maybe I would get a new subscriber. I really had no idea. And then the managing editor of the main Morning Brew newsletter, The Daily, which has like over 2.7 million subscribers saw my tweet, read my newsletter, loved it. And then called, DM’ed me on LinkedIn about a job at Morning Brew.

Mike (24:52):

That’s amazing. I think one of the things I’m kind of hearing over and over again in your story is the advantage of putting stuff out into the world. And I think sometimes people can be nervous or shy to put their work or put themselves out in public. I guess, how do you think about putting stuff out into the world?

Rachel (25:15):

I think that’s one of my biggest pieces of advice is to just put yourself out there and put your work out there. I’m very much a perfectionist, but the moment I realized that what I put out there doesn’t have to be the end product, really changed everything for me, because you can always iterate. When I first started my newsletter, my personal newsletter, I had a format that I thought would work. And then it evolved over time based on what readers were liking and what kind of content they wanted to consume. So what I started with was not what I ended with, and it wasn’t the perfect newsletter when I first launched it. So I think really channeling the mentality that the first thing you put out into the world doesn’t have to be the best thing you put out into the world is a good piece of advice.

Mike (26:04):

Yeah, I also feel like it just highlights the unpredictability of the benefits or the potential that can come from other people seeing your work. Whether that’s on Twitter or Instagram or whatever, it’s just like, you don’t know who’s going to see it and reach out and offer you a job at Morning Brew.

Rachel (26:20):

Yeah. You never know. And you only get those kinds of opportunities if you put yourself out there.

Mike (26:27):

Totally. So tell me a little bit about what work you do at Morning Brew?

Rachel (26:31):

Yeah, so I write The Brew’s latest newsletter. It launched in November, called Sidekick, which curates a bunch of recommendations from the internet for smarter living and has about 150,000 subscribers at the moment. So when I joined The Brew, I was writing an existing newsletter that was kind of a previous iteration of Sidekick. And then all in the background developing what Sidekick is today. So really learning what it takes to launch a newsletter, write that for a much larger audience than I’ve ever written for. And then also working on larger scale projects surrounding the newsletter, the brand, and kind of what it looks like beyond email.

Mike (27:12):

Sounds like a lot of fun. And it also sounds like it’s kind of exactly what you were looking for when you mentioned as a student you wanted to work with kind of a smaller startup and kind of marketing, but then you realized that you’re a really talented writer and curating stuff. It sounds like they’re always kind of tailor made for you. How is the experience of, is it what you expected when this is what you desired so many years ago?

Rachel (27:35):

Yeah, I think it’s amazing to work at a fast growing startup. Things move really fast and I mean, I’ve been doing things that I’ve never done before and wearing a bunch of different hats, but it’s been really fun. I run a social media for my own newsletter and I’ve never run social media for a brand before, but every day I learned something new. I also think when you work for a fast-growing startup, you get to work with a ton of really creative, smart people. And that’s probably my favorite part of working at Morning Brew is, I can Slack the founders of the company and we can set up a call tomorrow, or I can work with all different people from all different backgrounds and understand kind of their process and learn from really great talented writers too. And then also what it takes to build an audience and what it takes to build a media company.

Mike (28:36):

Yeah, sounds like all good learnings and experiences. Okay, maybe just a couple more questions here. Looking back, what recommendations or advice would you give to a freshmen, Rachel, when thinking about your career or your job after school?

Rachel (28:55):

I definitely would echo what I said earlier in that don’t be afraid to put yourself out there and take a risk. And that doesn’t have to mean building a company in college. That can mean writing a newsletter. It can mean just starting a little side project or just experimenting about something you’re really curious about. So I would say that. I would also say that something I wish I knew earlier was the power of Twitter. I hate to recommend a social media platform. It feels very odd, but I think when I was in school, everyone told me that I had to be on LinkedIn and that LinkedIn was the main way to connect with people. But what I’ve learned from my job and how I got my job is literally through Twitter is that depending on what type of industry you want to go into, those people really live and breathe Twitter. And it’s a very cool space where you can learn about so many different topics and also kind of share your own creations and your own work and a little bit about yourself too.

Rachel (29:57):

Especially if you’re interested in startups or you’re interested in tech, or venture capital, or direct to consumer brands. Those founders and the people really building these companies live in that space. And so I wish I joined Twitter a little bit earlier so I could find those people, because I really didn’t know where I could find them.

Mike (30:18):

Right. I mean it’s, I think some people still think of the job hunt as this archaic thing of like applying online or LinkedIn and interviews and stuff. But the truth is, if you follow your curiosity like you did and find the smart people in the industry or companies you want to work with and start asking them questions, or having conversations, or showing them your work, that’s probably a much higher likelihood of some opportunities coming out of that.

Rachel (30:48):

Definitely. And that’s also another piece of advice I would give to people is to reverse engineer the job process. Like for me, I think my story is just an example of when you create something, sometimes the reward is so much bigger. I would spend hours looking on LinkedIn. And to me, I think actually creating something, something you are passionate about is so much more powerful and valuable than just scouring the internet for jobs. Especially if you want to work at a really innovative, disruptive company like the Morning Brews of the world. I definitely don’t know if this advice would be applicable to someone looking for a job at JP Morgan, but I think for startups, they care really about what you actually create versus what’s on your resume. And when I interviewed for my job at Morning Brew, I think I only really talked about the newsletter that I created, my own personal newsletter. They saw my resume and they knew what I did in school and what internships I had, but they only asked me about my own creation and what I learned from that.

Mike (32:00):

Right, I love that. It’s so clear that you are already doing the work that they’re looking to hire someone to do, and you could prove it, because you were doing it for free and just because you wanted to.

Rachel (32:10):

Yeah.

Mike (32:11):

I love it. I think that’s great advice and a great place for us to end. So, Rachel, thank you so much for joining.

Rachel (32:18):

Thanks for having me.

Mike (32:19):

Of course. If there’s one lesson I would take away from Rachel, it’s the power of creating something and sharing it with the world. If Rachel hadn’t started her personal recommendations newsletter and been unabashed about sharing it and tagging Morning Brew in a tweet, she wouldn’t have landed the job she has today. If you’re passionate about or interested in something, I encourage you to talk about it, write about it, build solutions and share your work with the world. You never know what might come of it. How I Got Here is a podcast from The Garage at Northwestern and is produced by Melissa Kaufman, Ben Williams and Elisabeth Wright. If you enjoyed this episode, please rate and review us on your favorite platform.