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Coffee with a Journalist: Jennifer Ortakales, Business Insider

Coffee With A Journalist - Jennifer Ortakales Dawkins, Business Insider

Episode 33 of Coffee with a Journalist is joined by Jennifer Ortakales Dawkins of Business Insider. At Business Insider, Jennifer covers small business and entrepreneurship for the “Strategy” team focusing on launching and scaling new businesses. During her talk with host, Beck Bamberger, Jennifer jumps into her takes on crafting stories that are helpful to entrepreneurs, covering breakout stars in the small-business space, and fulfilling readers’ desire for high-quality content. 

Click below to listen to the full conversation and read below for highlights from the interview:

Her Work Inbox

Beck:

Love it. Okay. Okay. Your inbox, your inbox. How crazy is it in there? Are there a lot of pitches? Do tell.

Jennifer:

Oh, yeah. The inbox is like a never-ending journey every single day. I feel like I get in to work in the morning, or log on these days, and there are already at least 30 in my inbox waiting for me from either the previous night or early in the morning. And sometimes I’ll ignore those because I have to just prioritize looking at the news and figuring out what I’m covering that day. And then from there, it’s just constantly pouring in. So I don’t even know how many I usually get on a daily, but it’s probably close to 150, 200 emails a day.

Beck:

Okay. That’s quite the batch. Now, with all those that you do get, how do you manage and filter? Do you read every single subject line? Some people, they will open every single one, which is crazy to me. But how do you manage it?

Jennifer:

I don’t know how anyone would do that, but I definitely have a system for myself that really helps. I’m a very organized person. So for me, I’m visual. I like to keep things organized with labels and filters. So first thing I do is typically organize any important emails or ongoing threads with a label. Sometimes it’s like calendar and events, so that’s something I know that is coming up. Or maybe a current event to cover.

Jennifer:

And then I’ll have PR pitches or possible sources. That’s actually one that I use to file away any pitches that I get that I think, “Oh, this founder or CEO seems really interesting, but I don’t really have the time right now to do anything on them.” I can put it in this bucket for later, and maybe revisit them. So it runs the gamut from current stories I’m working on, story ideas, pitches, studies and reports. Any companies that send me studies and reports that might be of interest for our readers, I’ll file those away as well. That way, when I’m working on a piece that might be relevant to that report, I can access it easier.

Jennifer:

So for me, it’s all about labeling, all about color coding in my inbox. But then I would say as far as actually getting to the daily grind of all these emails that I get, that are not labeled, before I even go into that process, it’s definitely just scan through the subject lines. If nothing jumps out at me, just trash it. I have to be super selective these days, because there are so many founders, so many entrepreneurs who want to be covered, and it’s great.

Jennifer:

And there are so many great ideas, but we just can’t cover everyone. So it really is all about that subject line for me. If I don’t understand what you’re trying to communicate, or if I don’t understand what the business is by the time I scan through that subject line, probably going in the trash bin, unfortunately.

Beck:

And then it’s gone? It’s gone forever? It’s not in your system? Mm-hmm (affirmative). Makes sense. Now, you mentioned that you’ll save a report, some data that comes out, something like that from a pitch. Do you return back to those three weeks, three months, a year later? I know some people do return to those, but almost in a timeframe that you go like, “Holy cow, I can’t believe they resurrected that.” Does that happen for you?

Jennifer:

Yeah, sometimes. I wouldn’t say a year. I think by that time, usually reports and studies are a bit outdated. Or there’s been something else that comes out that’s more interesting, or more relevant. But I would say that yeah, maybe a few months from now or maybe even six months tops, I might return to something. But I would say usually the timeline for me would be a couple months.

Jennifer:

Probably by the time it’s like three months old, not likely to look at it because there’s probably something that’s come out since then. But yeah, I’ll definitely return to them. And especially because I write a lot of evergreen pieces, so just because a report comes out does not mean I’m going to write an article about that. But if I’m writing an article that’s related, I will return to that report to see if there’s some interesting insight for that net graph or that lead.

How She Writes Stories

Beck:

Just as background. Got you. Related to how you come up with stories, and I’m looking at your latest list, you just had on the CEO of Spotify, you had something about craft breweries, you had best platforms for scaling your side hustle. You have a wide realm of what you write about, although retail and small businesses is definitely the focus of it. How do you come about deciding a story to do?

Jennifer:

I tend to look in a lot of different places. Obviously, the news and what’s happening, what is trending among entrepreneurship or what industries are doing well, what companies are coming up, that’s all stuff that I’ll consider. But I’m also looking for the breakout stars or the people who are just proving really, really successful business strategies that they can explain how they did it. And then that way, other entrepreneurs can replicate that. They’re providing replicable success, so that’s really important.

Jennifer:

And I think there are so many different businesses and ideas and founders out there that to me, the most important thing is, can you prove your success? And can you give us some really helpful tips and advice that other entrepreneurs or even aspiring entrepreneurs can utilize? And actually, it’s not just a success story of I did this from one to a hundred in a year, but there’s nothing to back that up. There’s no tactic, it’s a lofty like, “Oh, I just did my best, or I dreamt it up.”

Jennifer:

That’s not the kind of stuff that’s helpful. So we try to be helpful. And that means we need to really vet entrepreneurs and look for the most interesting information, and even data behind their success.

Beck:

Got it. So it’s the sharing, it’s indicating? And then really, what can someone read to take away and implement themselves?

Jennifer:

Yeah.

Beck:

You guys do, by the way, I have to give credit to Business Insider, with a different angle on the funding announcements, which are very cliche in this tech world that we’re in. But you guys do the analysis of the actual deck, which I think is so critical and interesting. Because you read an article and you’re like, “Oh, these people got $10 million, but I want to see what exactly convinced people to give you $10 million.” So I think that’s really great.

Jennifer:

That’s actually great to hear because that’s something that we are always trying to tap into, and we’ve found that our readers really like those. So I think it’s like you said, that visual, tangible results of we earned this much, but here’s exactly how we did it. And people want that, they want something that’s replicable. They want something that they can copy and paste, and maybe put their own spin on, but they want some sort of reference or guideline for them.

Her Thoughts on the Future of Journalism

Beck:

So I’m scanning back up on your long, long, long, long, long, long, long resume of all the various things you’ve done. And as we talked about, so you’re recent. 2016 graduate, so it’s not like you’ve been in the industry 25 plus years, and we have folks on here who have. But what’s your take on the future of journalism?

Jennifer:

No, it’s interesting, even just from there. I haven’t been in the industry for as long as so many other seasoned journalists, but I think it’s interesting how when I was in college, the focus was still on print. They were still trying to make sure that journalists were going to be multifaceted and very fluent with digital media, but I declared my focus in print journalism.

Jennifer:

And now, I think that it’s funny to think about that as even being something you had to do. Because today, I don’t know what Emerson does at this moment, but I think that at this point, it’s like maybe you can go into either broadcast or digital. But that print specification is not really the most promising for your career outlook. And I think that anyone who studies digital journalism will be fine in print as far as the learning and the techniques and everything that you need to know.

Jennifer:

So I really think that, obviously, as we know, digital is the future. And unfortunately, print is just never going to be the same. But I also do think that it’s multifaceted. And I think that something that we’ve even seen at Business Insider is our subscription just growing so much, that really indicates to us that people are willing to pay for high quality journalism and inside information if there’s a story that hasn’t been told from any other outlet. Or even if it’s just access to more high profile people.

Jennifer:

I think we’re crossing that bridge now where, before, we were in a place where everyone expected content to be free. But especially now with streaming services and Netflix, Amazon Disney+, all of these companies, you have to pay for their content. They’re not allowing things to be free, so neither are we. Journalism has to be paid for. We’re also a business. And so I think that subscription model is just going to grow, as you’ve seen with Business Insider, and so many other companies are also starting subscriptions.

Jennifer:

To what degree? Not really sure. Obviously, there’s still room for free content and news, but I think that for the most part, there has to be some sort of business model there where you are paying for content that you’re consuming. Because, how else are we going to survive?

Beck:

Yeah.

Jennifer:

And I think that also changes things. In college, I was always so interested in investigative journalism or features and profiles. And that stuff is great. And actually, Business Insider does a lot of amazing pieces like that. But I also think that there’s a huge appetite for bite-sized pieces where readers just want to know the one tip that they need to know for the day, or that one piece of insight they need to know for the day. And so pieces don’t always have to be super long.

Jennifer:

We don’t always have to publish 1,000, 2,000 word story to get to the bottom of what readers want. Sometimes they just want a 400 word story. And that can still be really high quality, and it can still be maybe even a really great interview. But you just break it down into smaller pieces. So I could interview a founder or a CEO of a company. And instead of writing a huge 2,000 word profile on them, I could do a couple 400 word, maybe 300, 400 word stories about specific insights that they gave. Or specific topics that they talked about during that interview.

Jennifer:

So I think it is transforming into something that you’re creating more content for varying interests and a variety of different people who want different things. But at the center of it, it has to make money obviously, to survive. And …

Beck:

Yeah, it does.

Jennifer:

Unfortunately, we’ve seen so many publications folding and layoffs, so that can look really discouraging. But I think when I look at how long, even just for the past few years that I’ve been at Business Insider and seeing their growth, they really are a testament to being able to grow in the midst of an industry that’s actually having a lot of difficulty.

Beck:

Something could be said, too, to your point on, oh, it’s a shorter story. And Business Insider does such a great job with that, where they put the bullet points of the main summary right at the top. And you’re like, cool. I read the headline, I can read the summary, and then I’m like, “Ooh, okay. I want to know more.” Boom. Then you go throughout the whole article.

Beck:

I think there’s just a lot of smart things that’s going on over there. That is a showcase of how you can monetize, have gated content, still have some that you can access otherwise, but the gated content model and so forth. Super interesting. I’m glad you’re at one of those places right now.

Jennifer:

Me too. I am very grateful to be at Business Insider, and doing what we’re doing. I think that they’re very innovative and always trying to improve from the last story. And ultimately, the thing that I’ve always been drawn to as an employee there is just how well they cater to the readers. If readers are the ones that we are writing for, we should be writing what they want to read, obviously.

Jennifer:

And it seems like a very basic thing, but I think a lot of publications lose sight of that because they want to do that ultimate journalism or that dream goal piece. That’s great, and you should pursue those pieces. But you also have to know that your job relies on making readers happy. And if they’re not enjoying your stories, then you’re not going to enjoy your job.

________

For Jennifer, a compelling pitch is all about understanding her beat and showing the value that is helpful to her readers. To be sure your next pitch to great journalists like Jennifer is as valuable as possible, read our article, Your Complete Guide to Pitching the Media. We cover everything from the 5 elements every pitch should include to how to send that follow-up media pitch. 

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Mathew Cruz

Mathew started at OnePitch in January of 2020 as a Marketing Apprentice. He currently serves as the SEO & Content Marketing Specialist handling content creation from social media to the OnePitch blog. Mathew studied Integrated Marketing Communications at San Diego State University. In his free time, he loves creating art, visiting museums, and traveling.

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