Ben Bergman of Business Insider joins me and Jess Mah on sharing his journey and the inside scoop on tech journalism.
In this podcast, we talk about the following:
- The Nature of Tech Journalism – Ben discusses how tech journalism differs from other beats, why he’s drawn to covering venture capital, and how tech startups create interesting stories because founders aim to build the next big thing, not just profitable businesses.
- The Legal Aspects of Journalism – Ben describes the extensive legal vetting process that occurs before publishing stories, how he handles threatening letters, and his commitment to protecting anonymous sources even if it meant going to jail.
- Interviewing High-Profile Figures – Ben shares his experiences interviewing notable tech figures like Adam Neumann, discusses his approach to preparing for interviews with high-profile subjects, and explains how he tries to ask questions others haven’t asked before.
- And many more!
Table of Contents
Video
Watch the full episode on YouTube here.
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Full Transcript
Ben Bergman: People don’t start tech companies to create a mildly profitable business. They create it to create the next Airbnb. Well, you just have to have better sources. It’s really the same for every form of journalism. And you’re only as good as your last story. Poker is just, you know, in terms of assessing risk versus reward. I’m not allowed to invest in companies. I’m not allowed to take any consulting fees. I’m not allowed to be paid for stories.
Jess Mah: Ben, welcome to the pod.
Ben Bergman: A pleasure to be here.
Jess Mah: Yes. Wondering if you can tell everyone 30 seconds about yourself.
Ben Bergman: So I’m a senior correspondent at Business Insider, where I cover the very exciting world of venture capital and startups. Before that, I was a producer at NPR for a long time and then a reporter at the NPR station here in LA. I did the Knight-Bagehot Fellowship at Columbia Business School, and I was the founding senior producer of The Journal, the daily podcast for The Wall Street Journal.
Jess Mah: That is baller. That’s awesome.
Ben Bergman: Thank you, thank you.
Noah Berkson: Tell us about that process of starting the podcast for The Journal.
Ben Bergman: So this was after I did this fellowship at Columbia Business School. I had always been a journalist, and I thought it would be interesting to try to be on the other side, to be more on the management side of media. And this was, of course, when The Daily had launched and was enormously successful. And so I got a six-month gig, Gimlet Media, and they did this partnership with The Wall Street Journal to be the competitor to The Daily. And so we were testing all this stuff out and in the origins of starting the podcast. And it was a great experience, but it was not for me. I really missed being a journalist. I love being a journalist. I didn’t like being more of a manager and being in meetings all day.
Noah Berkson: Have you always known that you wanted to be a journalist?
Ben Bergman: Yes. So I had a newsletter when I was about 10 years old called Benny’s Bulletin. My mom started the first parenting magazine in the country, and I would go up and work around her. And in high school, I would read The Daily News every morning. In college, I got to intern at The New York Times. So I really always have.
Noah Berkson: What was the first interview that you remember doing?
Ben Bergman: Well, I remember when I was in middle school, APEC, the Asia-Pacific Economic Cooperation, came to Seattle, and Bill Clinton was there, the president at the time. And I got to go cover that. And then he came to actually one of my classes in college, and I wrote that up for the college newspaper. And that did pretty well.
Jess Mah: And then did you ever imagine you’d actually be successful as a journalist and be able to interview, like, Adam Neumanns and Dalai Lamas of the world?
Ben Bergman: Well, I hoped so, but I wasn’t sure. I mean, journalism is such a hard field to break into, and I thought I might give it a try and be a lawyer if that didn’t work out. But really, journalism is all I wanted to do. But I had no idea that I would be a tech journalist or what kind of journalism I would do.
Noah Berkson: Why tech journalism?
Ben Bergman: Well, I always tell people, you can plan and say exactly what you want to do, but it never really works out that way. But I think I became a tech journalist because I did the program at Columbia Business School, and it’s where the action is. Tech is the most exciting, interesting people. People don’t start tech companies to create a mildly profitable business. They create it to create the next Airbnb. And so that really makes a lot of interesting people and a lot of interesting stories. And I used to cover politics, and politics is very important, but everyone covers politics. There are hundreds of reporters, but I’m really one of only a handful of reporters that covers venture capital.
Noah Berkson: What’s the key to being successful as a journalist in politics? If you’re going to be the top of the top, what do you need to do differently than the other 99%?
Ben Bergman: Well, you just have to have better sources. It’s really the same for every form of journalism. It’s not the writing that’s the difficult part. It’s getting the information. And you look at the top reporters, like Maggie Haberman or Jonathan Swan, and they just have great sources. They’re able to break stories that no one else is able to.
Noah Berkson: So it’s really a network that you need to create over time that allows.
Ben Bergman: You to get those cultivating sources, finding sources, and getting them to tell you information.
Jess Mah: And you’re a really popular person. You have a ton of friends. You throw great parties, from what I hear.
Ben Bergman: Where did you hear that?
Jess Mah: From you? Is that from me? Is that… Is that part of what makes you successful? Because you’re making genuine, authentic friendships with people. And because of that, people are more likely to advise you on what to talk about.
Ben Bergman: People always ask, is this for work or for fun? And it’s all really part and parcel of the same thing. And I do love people, and I love hosting people. That’s why I host poker games every weekend at my house. That’s why I do love having parties and events and going to a ton of stuff, because I think it’s meeting people. Everything comes from meeting people. Whether it’s a job opportunity or playing on an amazing tennis court or getting a story idea, it doesn’t come from sitting at your desk.
Noah Berkson: How does that change the way that you build relationships with people? Because I imagine people go like, oh, I want to be your friend, but also I’m a little wary about maybe what I tell you. Is that going to end up in an article? Or could there be some negative repercussion?
Jess Mah: From this if I get too hammered at Ben’s house, it’ll be published tomorrow.
Ben Bergman: Well, it’s funny because I’d say most of the time it’s the opposite. Like, people are so excited to pitch their startup or get me to write about them that, you know, that. And sometimes I’m like, oh, is this person just wanting to be friends with me to get me to write about it? But there are people who definitely are afraid of reporters or afraid that I’m just going to write up something that they say. And that’s not how it works. I’m not, you know, I will, you know, get ideas or someone will say something, but I don’t think people understand, like, the level of reporting that it takes to go into a story. So I’m not just going to write up something that I hear at a random party.
Noah Berkson: How often does that happen where you feel like people approach you or try to befriend you, and it’s like you realize that it’s kind of clear that they just have the wrong intentions?
Ben Bergman: Well, you know, we are in somewhat of a transactional town, and I think, you know, that it depends where you go. You know, I’m reticent to go to Tech Week events or something like that because that can happen a lot. And I try to be open to everything because just like a VC always wants to have a wide purview and hear lots of ideas, you never know where a good idea is going to come from, and you never know who’s going to have value in a certain way. But it’s nice when it’s not just purely transactional.
Noah Berkson: Do you feel like a lot of conversation as a journalist? Is it pretty transactional? You feel like as you’re meeting people, as you’re doing stories, is that generally the way that you feel when you’re going into a story?
Ben Bergman: No, I would hope not. I think there’s clearly people who just want something, but it’s not entirely wrong either. I also try to provide value to people as well, whether it’s giving them publicity or getting word out about something or giving them information that they want as well. Because it can’t just be a one-way street in any dealing that you have.
Noah Berkson: Do you have any example of something where you’ve written an article about a company, and it’s just been, it’s helped them in a huge way, been super beneficial to them personally, to their business?
Ben Bergman: Yeah, it happens a lot. I mean, because we do a lot of lists. People love lists, whether it’s the rising stars of VC or the best startups to work at. So we put a lot on the map. And in terms of a VC firm, I wrote about this firm, Trek VC, because they use an AI algorithm to determine future unicorns. And they said that got them so many deals once we wrote about them because people hadn’t really heard of them. And then everyone was like, wow, here’s this firm, they’re doing well, maybe we should let them on our cap table.
Jess Mah: Wow, that’s sweet.
Noah Berkson: You’ve had, I guess in another example, negative things about companies where it’s been very harmful to them or that’s created enemies for you out of writing about companies?
Ben Bergman: Yeah, that’s part of the job. I really don’t think you can be a journalist if you’re afraid of what people think. And I never want people to just… No one’s going to respect me if I just write nice things all the time. At the same time, I never want to just be known as someone who writes hit pieces or is negative for the sake of being negative. But after I’ve written critical stories about companies and VCs, people always reach out to me either to say, wow, I’m so glad you finally wrote that, or here’s another idea, or we respect you if you wrote something that was accurate. Not a hit piece, but something that everyone talked about but no one has written about.
Jess Mah: Yeah, well, speaking of which, over the past year I’ve had a lot of people mention an article that you wrote about Mark Suster, and they were commenting on what it was like to be on the board of a company with Mark Suster also on the board and how they perceived him to be reacting to the story. And most of the feedback was he didn’t take it very well, and he was a bit pouty and sour about it. What was that like for you? Are you worried about making enemies? Because LA is a pretty small town. How do you think about that?
Ben Bergman: Well, yeah, I mean, I think that story was a little more difficult than normal because Mark is a legend here in LA, and I live in LA, and it’s a small venture community. But, you know, Mark and I still talk all the time. He still invited me to Upfront Summit, which I appreciate. And, you know, the feedback after that story, I mean, there were a few people who thought it was too harsh, but at least to me, it was overwhelmingly positive. And, you know, I think that was a story that needed to be told. I think I spent a lot of time, I spent a ton of time with Mark, which I appreciate him being so open with me. And, you know, I think it was tough, but it was fair.
Jess Mah: Yeah, I agree with that. I thought the way you articulated the story was very well-rounded. How about some of these other people you’ve spent time with, such as Adam Neumann? Do you have any reflections on what it’s like to talk to people who are so iconic?
Ben Bergman: Well, you can’t think of it as that, right? It’s hard, especially with someone like Adam Neumann, who is larger than life. I mean, there’s no tech person that’s really talked about more. Well, probably Elon Musk, but certainly Adam Neumann is up there. And I watched the TV show about him, and I asked some of the people at SoftBank, I’m like, what is it like when I’m going to meet Adam Neumann? I just watched the show with Jared Leto, and they said he’s even more charismatic and good-looking than Jared Leto. And it’s true, he is even more charismatic. And I think it pretty quickly goes away that, oh, I’m talking to Adam Neumann. You have to treat it just like any other person and not be intimidated by someone, whether it’s the Dalai Lama or, you know, Pete Carroll or Brad Pitt.
Jess Mah: How did you prepare? Like when you talked to Mark or Adam, just focusing on the business people you’ve interviewed, what is it like to come up with your question list? And how do you think about being different from the dozens and dozens of other interviews they’ve already had?
Ben Bergman: First of all, I read every interview they’ve done or watch every interview to see what they’ve talked about. Because I think hopefully one of the reasons people like it when I interview them is because I’ve done the research and also asked different things. So I try to find different things to talk about because a lot of times people just get asked the same questions over and over again. So I think it’s really important to do your homework.
Jess Mah: But since these people have been interviewed so many times before, do you always have that confidence that you’re going to be able to pull out some special nuggets that no one else has done before? Or do you worry about that? You’re like, you know what? Like, this might end up being another boring article?
Ben Bergman: Well, I try to, and then I probably wouldn’t publish the story because most of the things I do, at least until recently, were always behind our paywall. And so for someone to read something that I wrote, it had to be good enough that they would pull out their credit card and subscribe. So if I’m just writing something that everyone else has written, then no one’s going to subscribe. And that’s what I cared about writing.
Noah Berkson: Has it changed the way that you’ve done journalism in the last five or 10 years? Because now it is very different where someone needs to look at the headline and say, I’m going to pay to read that article, which I still think is crazy, but I understand that’s the way to make money. Does that change the way you think about your writing or the way you think about interviewing?
Ben Bergman: Well, for sure, because, you know, for instance, like every startup founder, most of the ones who are coming up to me want me to write about funding announcements or things like that. And, like, there’s just no way, unless it’s like OpenAI or something, that I’m going to write about it. Just because that’s everywhere. That’s not what people are going to come to us for. So I really do have to look for those things that are unique, and that’s why I spent so much time sourcing and talking to people. That’s like 90% of the job is finding the story that no one else is.
Noah Berkson: So what’s your end goal as a journalist? What’s the kind of North Star that you want to orient to? Where you say a founder might want to build and sell a company or make tons of money, what are you orienting towards?
Ben Bergman: For me, my goal is always to write about what people are talking about, but has not been written about. So you mentioned the story on Upfront and Mark, and that was something that, you know, I’d heard for years, and no one had written about. And so those are the kinds of stories that I like. That stuff that is kind of known but no one’s ever covered before.
Noah Berkson: And when you’re reaching out to people for an interview, is a lot of that cold? Is that like cold reaching out, cold email, just from your Insider email, or is that warm intros? How does that work?
Ben Bergman: Well, it depends. I mean, if it’s someone like Adam Neumann or something, that’s going through their PR. But a lot of my work is reaching out to employees of companies. Right now I’m doing an investigation on a startup, and there I just reach out to employees on LinkedIn cold. It really varies.
Noah Berkson: Are people generally really receptive to that?
Ben Bergman: No. So I probably will do about 100 reach outs and maybe get two.
Jess Mah: Wow.
Noah Berkson: Wow. Are there any articles that you regret publishing as you look back and say, like, I wish I wouldn’t have published?
Jess Mah: That, or you wish that you perhaps approached it in a different way? Maybe you’re too negative, or you’re too positive, and now you only realize that after.
Ben Bergman: I mean, no, I mean, I’m sure there have been ones that I would, you know, earlier in my career that I maybe, you know, look back on, and I’m like, that could have been better. I’ve learned so much. Or the benefit of hindsight, something else will come out. I can’t immediately think of something, but I’m sure if I read it that I would regret it.
Noah Berkson: How much now do you think having a personal brand is important to your success as a journalist, as opposed to who you’re writing for, who you’re working for? But your personal brand, how does that play into it?
Ben Bergman: Well, I think it’s immensely important as much as that word is kind of cringe, and it is. But I think having my personal brand on Twitter or LinkedIn or other stuff is very important because you see the biggest journalists of our time, at least in tech, are people who, you know, their names, like Taylor Lorenz, Kara Swisher, Alex Heath, I think much more than, you know, the outlets they’re at. It’s not as if everyone’s going to The Wall Street Journal or The New York Times. And, you know, it’s a very turbulent time in journalism and tech journalism. So I think the safeguard against that is having your own brand.
Jess Mah: Do you worry every month about missing out on the next big article or story? Are you thinking, wow, I haven’t had a big hit in like three months. Maybe I lost my mojo. Has that ever crossed your mind?
Ben Bergman: All the time. All the time. Because this is such a competitive business. And it’s also, you can see what everyone else is doing, and we all know each other so well. So when I see Kate Clark publishing a great story at The Information or Berber Jin and Tom Dotan, the story about the OpenAI funding, I’m like, God, I wish I would have gotten that. So that happens all the time. And you’re only as good as your last story. I mean, I can be like, wow, that story did great. That did so well. But then it’s like I got to write another one. And sometimes, you know, I’m like, what am I going to do? Although I will say when I was a more general interest business reporter, when I was at the NPR station here at KPCC, I would sometimes worry about what was my next story. But I feel like covering venture, there are about 100 stories I want to get to do.
Noah Berkson: You spend your day just reaching out to people just to see what you can get. Is that like the majority of your time spent? Is it just kind of putting feelers out to see what’s out there? Or is it, hey, I think I have this hunch about this. Let me start to go investigate it.
Ben Bergman: It’s probably a mix. I mean, when I’m working on a story, which is the best thing, that’s like the place I like to be in and have a lead and getting far on a story. I’m reaching out to people with a very specific thing in mind. But also a lot of it is just coffee chats and catching up with sources, seeing what they’re saying, seeing if they have any great tip to share.
Jess Mah: What are the metrics for success in a story?
Ben Bergman: Well, so they’ve recently changed at Business Insider, at least for me, it was all about the new subscribers that you would bring in. And we’re very metrics-driven, unlike a lot of journalism organizations where there’s supposed to be more of a firewall between that, and you’re supposed to publish good stories and not worry about it. But we’ve always been more metrics-driven, but actually recently we just changed it to a new metric where we’re judged on the amount of time our existing subscribers spend on stories. And I think that’s a good change. But it’s definitely changed the kind of stories that I do.
Jess Mah: I see. Could you talk about that some more?
Ben Bergman: Yeah. So like a lot of times I’ll do stories that are not breaking as much, but a little bit more what people are talking about. So, for instance, I did a story on how VCs are seeing the election, and I wasn’t really breaking any huge story there. Similarly, I did a story on Character AI and the string of kind of these acqui-hires that I wasn’t breaking a big thing there like I would have been doing before, but I was doing more analysis. And those stories were very popular with our existing subscribers, but they weren’t necessarily bringing in a huge number of new ones.
Noah Berkson: There was, as you say, there was Matt Taibbi who had that IRS visit because of something that he wrote. He had some negative press on the Biden administration or was kind of hurtful. Do you think about that when you’re writing any pieces where you’re like, this could actually be very negative for me, and I need to worry about the repercussions that this could have?
Ben Bergman: I really try not to. I try to let the chips fall where they may. And most of the time… I mean, I shouldn’t say most of the time, but a lot of times I’m being threatened to be sued, right? And if I’m worried about that, like, that’s not a great place to be. And I wouldn’t write a lot of the stories that I’ve written. And I’m fortunate to have a great legal team and a company that is willing to stand up to me. If I didn’t have that, I would be a lot more worried about it.
Jess Mah: Wow. So has Business Insider or any other entity you worked with been sued because of your articles? And what is that like behind the scenes?
Ben Bergman: Well, I don’t want to jinx it, but, yeah, I don’t think we’ve actually been sued. We get a lot of threatening letters, and they can look scary, but, you know, luckily our lawyers, you know, see through that, and we’re, you know… But I don’t think people understand the amount of vetting that we have to do behind the scenes for a story and also how many stories we work on for months that never make it into print.
Jess Mah: Wow.
Ben Bergman: Because our legal team feels that we don’t have enough to go to print.
Noah Berkson: So they’re really vetting every story before that goes out.
Ben Bergman: Yes.
Noah Berkson: How often does that… How often do they come back to you and say, hey, we need more here, or there’s not enough done here, like, we can’t publish yet. Is that a common occurrence?
Ben Bergman: Yeah, very common. Very common. Because they say, oh, well, you don’t have, you know, the sourcing on this, or you have these anonymous sources. If this person sues us, that’s probably not going to be enough to get us to win. So you need to get more documentation for this. You need to get more evidence for this. And, yeah, I’ve had a lot of big stories that have not been able to be released because legally they just aren’t cleared. But I think we got to be aggressive, but we also have to be cautious in that regard.
Jess Mah: So even if you know who the sources are, if they’re not willing to go on the record and have their name be published in the article, then it’s not as valuable.
Ben Bergman: It is because… Or it’s not because I wouldn’t be able to give up the sources. And people always ask me that, if you’re sued, will you give up? And I won’t. So therefore, if I’m on the stand and someone’s saying, how do you know this? And I’m saying, well, this anonymous source. And they say, well, who is it? I wouldn’t say. So I think, legally, that does make it more difficult.
Jess Mah: I see.
Noah Berkson: To what extent would you go to protect a source?
Ben Bergman: I would go to jail for a source. I mean, that’s what Judy Miller did at The New York Times. And I’m not covering national security, so it’s a little different. But, yeah, I mean, I take that very seriously.
Noah Berkson: What is the key to asking good questions?
Ben Bergman: Listening. Because most people just have their sheet of questions, no offense, and they’re moving…
Jess Mah: On to listen to anything on this list.
Ben Bergman: No, no, you got… No, but… And they just want to ask the next question. And it’s the same when you’re on a date or whatever. It’s like you need to listen to the person, and that’s what has the good questions. And also, I think Larry King famously didn’t prepare for interviews, and that was his style, because he wanted to be the everyman. But I think you should be prepared and know what the person has done and where to go and what hasn’t been asked before.
Noah Berkson: What’s been the most embarrassing interview you’ve done, from the sense of you just realized you weren’t prepared in that interview for what was going to happen, or you hadn’t done the research, or you slipped up?
Ben Bergman: Well, I don’t know. I mean, I don’t think I’ve ever luckily done that. And the interviews I do now are very different, right? Because when I was doing interviews, when I worked in public radio, the whole thing would be aired like you guys aired. It’s a podcast. So the questions you ask are sometimes very important, even if you don’t get the answer. But for the questions now, I’m just trying to get information. And I think another key is just to keep asking the question until you get the answer. Because a lot of people don’t do that.
Jess Mah: They just want to dodge, or they get distracted.
Ben Bergman: Exactly.
Noah Berkson: This friend of mine, Cal Fussman, he used to have breakfast with Larry King every day, famously. But he had this story about interviewing Mikhail Gorbachev, and he got this interview, interview with him, and it was supposed to be… It was an hour. It was an hour-long interview. And he gets there, and they’re like, oh, wait, we, you know, it’s maybe it’s supposed to start at 1 PM, and they’re like, ah, you got to wait a little bit. He’s still behind. He’s still behind. He’s still behind. He’s like, well, this is going to cut into the interview. And they’re like, well, yeah, like he, you know, he needs to be done for the next meeting. The next meeting. And so he, they end up coming out and they say, hey, you have, you have 10 minutes. And he’s like, well, 10 minutes, I need to interview this world leader, right? And he’s talking about nuclear arms. And he’s like, how am I? And I have to translate it. Everything I say is going to get translated to Russian and then get translated back. And he’s brainstorming, okay, what do I ask him to try? And like, I need to get something from him. But, you know, normally you have five minutes of pleasantries when you start writing an interview. So he’s like, I have basically like a couple minutes to do it. And he ends up kind of throwing away the script of what he was going to talk about. And he goes, what was the biggest lesson that your father taught you? And he asked him this question, and the guy translates it, and you just see him just kind of change his whole mood because it’s not the question he thinks is coming. He thinks it’s going to be something about nuclear arms and what he thinks about that. But he was like, that was really the key to a good question in an interview is how do you get kind of aim for the heart instead of aiming for the head. And I think, like you were talking about earlier, a lot of people when they get interviewed, they know the questions that are coming, and they’re just have this like kind of recorded track ready to do that. You almost know the question. You know the answer that’s going to come out of their mouth. How do you get people to open up when you’re interviewing them in a different way than any other reporter?
Ben Bergman: Well, I think it’s figuring out, you know, where they’re coming from too. And it’s different doing the kinds of interviews with famous people like Adam Neumann versus when I’m on a call with a source, right, which is really the most important thing I do. And getting people to open up is about understanding their motivation. So people always ask, why do people come to me? Because if you’re an employee at a company, you’ve probably signed an NDA. So why would you talk to a reporter? And it’s about finding their motivation. Do they have a story to tell that they think is important? Are they unhappy with the company? Do they feel that they’ve been mistreated? Maybe they’re a competitor of the company. Maybe they feel like this is just a really important thing that they want to get out there. So it’s about that and about listening and feeling like you’re going to tell their story accurately and fairly.
Noah Berkson: And I imagine early on in your career as a journalist, you get a lot of access, and you get access probably in a different way than most people get access to important people, powerful people, political figures, whatever that is. Did you feel a lot of kind of imposter syndrome when you go in the room with somebody, and you’re probably fresh out of your, you know, you’re fresh in your career or young in your career, and in no other way would you both be in the same room having a conversation?
Ben Bergman: For sure. I mean, that would… It still happens a lot. I mean, just like the people I get to meet, and I’m like, how do I get to do this? And who am I talking to? This person? Or even when I did the Columbia fellowship, we had a two-hour dinner with Jamie Dimon, and I’m obsessed with credit cards. So I’m quizzing him about the Chase Sapphire and how it makes money for them. But again, it’s like seeing everyone as people and not being intimidated by people. I think the only person I really kind of clammed up on is when I got to interview Pete Carroll after they won the Super Bowl, because I’m from Seattle, and I’m a huge Seahawks fan, and that was the only one where I got a little tongue-tied.
Noah Berkson: Is there anyone today that you have not interviewed you really want to interview?
Ben Bergman: There’s a lot of people. I mean, I think for everybody, tech journalist like Elon Musk is sort of the Holy Grail, although he’s certainly out there a lot. So I’d probably be, I think, Jeff Bezos, I’d really want to interview because he doesn’t do a lot of interviews. And I think he’d be so interesting. And I’m from Seattle, seeing the rise of Amazon.
Noah Berkson: If we were going to brainstorm this right now, how you get that interview with him, how do you go about that?
Ben Bergman: So, yeah, it would be reaching out to his people and being like, okay, I know you don’t do any interviews. You’re on your giant yacht and building your space company. But here’s what I can offer you. I’ve watched your company since the beginning. I literally grew up next to you. And I’m interested. And here’s what I can provide. Because for people like that, he can go anywhere, and someone like Adam Neumann can go anywhere. So why is he going to go to me?
Noah Berkson: What can you provide? What could you provide to Jeff Bezos right now that he can’t get elsewhere?
Ben Bergman: Well, hopefully he’s listening. I would just, again, like being there in the shadow of Amazon and understanding the company so well and able to convey that. But I don’t know, it’s probably not a great pitch, so that’s probably why I haven’t landed.
Jess Mah: Here’s another idea. To what extent would you be willing to actually shadow him for a month? If that was the terms, you had to be 24/7 with him for a month, and then you could write about him. Would you do that?
Ben Bergman: So I’d have to be on his yacht in the south…
Jess Mah: Everywhere.
Ben Bergman: Okay, that sounds terrible in the twin…
Jess Mah: G550, but you have to drop all your other stories and work for a month. Is that a sacrifice you would make? Have you had to make any sacrifice like that where you spent a whole month or even three months just on one story?
Ben Bergman: Well, yeah, as far as the first question, yes, I would drop everything to go meet him. And I think oftentimes that’s how you get to know someone. You know, when you’re writing a profile, you want to see them in action, right? And because people themselves aren’t usually that able to talk about themselves. When I write a lot of profiles, and usually the most interesting stuff I get is not from talking to the actual subject of the story. And a lot of times the best profiles, they don’t even get access to the person. So it’s about talking to people they’ve worked with or known for a long time. But spending time with them is immensely important. I haven’t had to drop everything for a story, but there are stories that I’ve worked on for six months or a year, along with a lot of other stuff. But a lot of the stories I do take a long time, and a lot of it is because of all that legal review, where I’ll have to keep going back and keep working on a story.
Jess Mah: But what if you have the subject, like in this case, Jeff Bezos, on your side and helping provide, you know, other people you could talk to, and they’re obviously supportive. Would that make it easier, actually, for you to get this ad in three months or two months?
Ben Bergman: Yeah, that would definitely make it easier. But I would also have to talk to other people as well, right? Because, you know, I’d want to talk to, you know, because when someone gives you people to talk to, they’re probably going to be, you know, friendly, and you definitely want to hear that, too. Yeah. But you also maybe want to reach out to people who’ve not had a…
Jess Mah: Great experience and get a full, well-rounded view. But then how do you paint that picture of like, hey, I want to give you a great profile, Jeff, and therefore you’re going to invite me on your yacht and to fly around on your jet with you to shadow you, but at the same time, I might try to pick up some dirt on you at the same time. That’d be very difficult for them to wrap their head around, for sure.
Ben Bergman: And I think that’s why most of the stories I do don’t involve that level of cooperation, because that’s access journalism. And that used to be more common because it was like, oh, Steve Jobs, we’re going to put you on the cover of Time magazine. And so we’re probably going to be more friendly, but now that’s not that important. And most of the best stories do not come from access. They come from sources and getting the information. And then once you have the story, the person would come in to give the interview, because they have to. But I worked on a very long story. One of my first stories at Business Insider was about Whitney Wolfe Herd, the co-founder of Bumble. And so I talked to a lot of former employees and people she’d worked with, and she never spoke to me for the story. They did answer a lot of questions via email, but I never spent time with her.
Jess Mah: Do you think that the story would have been considerably different, perhaps even more positive on her, if she had cooperated?
Ben Bergman: I do. I mean, I think there’s usually a benefit to people providing access because it usually just makes you more sympathetic as a reporter when you spend time with someone. And I think everything is in shades of gray, and when you talk to someone and find out their motivation, you’re just naturally going to understand them better. And I think that will be reflected in the story. So I think… I think the story I did on Mark benefited him as well as me, from him spending a lot of time with me.
Jess Mah: Yeah. So then what percentage of the time do they cooperate versus decline and answer very shallow answers via email?
Ben Bergman: I think with most of the bigger stories, they will cooperate eventually, but it can take a lot of wrangling. And I think they have to see that you’re serious and that you’re going to do the story with or without them, so they might as well cooperate.
Noah Berkson: I was going to ask, do you ask a lot of times for introductions from the friends that you’ve made through this and say, hey, will you introduce me to Jess? Because I want to interview her or do a story about her? Do you use those, or is that kind of like off limits? I don’t want to ask.
Ben Bergman: No, not usually, because I probably would just reach out directly to the person or to their PR people, or a lot of times the PR people will reach out to me because they’ll have people forward the email to them. So they’ll just say, hey, what are you doing? Can we help? And I say, well, I’m not quite ready, but I’ll let you know before we publish the story.
Noah Berkson: Yeah. Who would be the person you’d go to if you wanted this Jeff Bezos interview? Who would be the person to try and get that introduction if you had to name one person that you would go to to ask?
Ben Bergman: I don’t know. Well, you know, Andy Jassy actually lives on my block in Seattle, so maybe I could knock on his door and…
Noah Berkson: Ask him, would you be as bold as to do that?
Ben Bergman: Probably not, but maybe I should be. I mean, you know, fortune favors the bold, right?
Jess Mah: Yeah, exactly.
Ben Bergman: Yeah.
Jess Mah: Would you want to transition towards doing longer-form journalism or perhaps even writing biographies and books on subjects, or would you prefer just doing what you’re doing today, long-term?
Ben Bergman: You know, I really like the mix of what I do because I always have a couple long-form features I’m working on that take six months or a year to do. But I also, I’m a beat reporter, so I’m covering day-to-day VC for now, though. For now. But I do like that mix. And I also think, frankly, it makes me more valuable because there are a lot of very good feature writers, there are fewer good VC reporters.
Noah Berkson: You host this poker game. You’re really into poker. Has poker taught you anything about journalism?
Ben Bergman: Well, it’s taught me a lot about life. It sounds like a cliché, but I think it’s true that poker is just, in terms of, assessing risk versus reward. For instance, I thought about it when I was applying to that fellowship at Columbia. I was like, there’s a small chance that I’ll get this. So I’m putting in all this effort and money into getting into the program. And I had actually tried a couple times, but if I get it, it will be this huge payoff. And I think that’s the same way you think about poker because you have a 30% chance of making a flush when you have two of the same suit. So it’s still a low percent, but it’s a big payoff if you make it. So you’re willing to put quite a bit of money into the pot. So for sure. And I think poker just attracts friendly, interesting people. And if someone asks me to hang out, and I say, great, do you play tennis or poker? If they don’t, it’s probably not going to work out.
Jess Mah: Both of them are in-person activities. Poker, you’re essentially reading your other participants with journalism. How important is it for you to meet your subjects in person versus on Zoom versus just do a telephone call?
Ben Bergman: Well, yeah, I mean, everyone wants to do Zooms, and I really do not like Zoom meetings. I think for me, I just get very little value from Zoom meetings. They were great during the pandemic, but it’s just, it’s very stilted, and you’re not really going to get, you know, where you get stuff is, you know, when you’re at a coffee shop or doing a walk with someone or, you know, at an event, and they mention something. So it’s not great. The phone is better than a Zoom because people are a little bit more casual, they’ll open up a little bit more interesting. Zoom is so formal.
Jess Mah: Wow.
Noah Berkson: Did you think that business school was really valuable for you?
Ben Bergman: It was, I think for one thing, like learning the mechanics. Because I did politics major in undergrad, so I had no idea about corporate finance, accounting. So doing those… Not that I could do a discounted cash flow if you asked me to right now, but just sort of like having that confidence and knowing that background. But the most important thing was meeting people and just being around really smart people from there. And that just opened up a whole other world for me. And I knew that I wanted to cover business instead of just be a general interest journalist.
Noah Berkson: So you’re saying that meeting the people at Columbia was a better network than the network that you get every single day or the access that you have to everybody?
Ben Bergman: Well, I wouldn’t necessarily say that. I mean, being a VC journalist now, I really do meet such great people. But as you know, and now some of the best people I meet really are through tennis and poker. So it’s all great. But yeah, I mean, that Columbia network is great as well.
Noah Berkson: If you were going to be doing something else, and you had to leverage the network that you’ve built today through journalism, what would you be doing?
Ben Bergman: Well, I mean, the easy answer would be be a VC, right? A lot of people make that transition from journalist to VC, and I think it’s a similar skill set, right? Because your network is so valuable, you’re getting information that people don’t have, and you’re also telling stories.
Noah Berkson: So I’m thinking about this, like, Dot LA was kind of that, right? They had some or like an investment arm, I think, Sunnyside or something that was tied to LA. So it was like, hey, we not only invest in you, but also promote you. Does that model work?
Ben Bergman: Well, I mean, 75 and Sunny is Spencer Rascoff’s family office. So completely separate from Dot LA. You can’t do both at the same time, right? And at Dot LA or Insider, I’m not allowed to invest in companies. I’m not allowed to take any consulting fees, I’m not allowed to be paid for stories. Because I really think if you’re doing journalism, it has to be about the story. And once you start mixing them, it’s not journalism anymore.
Noah Berkson: Do you think you would make a good VC?
Ben Bergman: I think so. But I think the difficulty for me, though, would be that I tend to look at a company, and I’m like, how the heck is this going to succeed? There’s 50 competitors. There’s all these obstacles. Here’s what can go wrong. VCs have to be very optimistic. They have to be, okay, this will be the next Uber. I definitely don’t think I could be a startup founder. I’m around startup founders all the time, and I respect them so much, but that is not the mentality I have. And actually, there are also journalists like Eric Newcomer, who’ve gone into a more entrepreneurial track, starting their own Substacks. I like being at a company where I have that salary. I have the benefits.
Jess Mah: You have a legal team.
Ben Bergman: I have a legal team. And I know if I don’t have a great story for two months that I’ll still have a paycheck coming in and can make the rent.
Noah Berkson: You’ve been here for five years now in LA. What has dating been like?
Ben Bergman: Oh, wow, that’s a turn. You know, it is… It’s great. I mean, I enjoy dating. I think a lot of people say how horrible it is, but since I love meeting people, right? I think that it’s usually fun for me. And there’s very few dates I go on that I’m like, oh, you know, I wish I wouldn’t have gone on that. I definitely think dating in New York is better, at least for guys, but it’s good here as well.
Jess Mah: So when you and I met on Hinge, I didn’t know this, by the way.
Ben Bergman: Yes.
Noah Berkson: Just for context, Jess, Ben’s gonna come on the pod. She’s like, wait, I think I went on a date with him, and I…
Jess Mah: Didn’t get asked out on the second date. What the hell?
Ben Bergman: Well, yeah, let’s do it. You were flying off. If you had to rate this date…
Noah Berkson: What was, like, a scale of 1 to 10, what would that be?
Jess Mah: Brutal. And then what’s your negative feedback for me?
Ben Bergman: No, no. I actually… I would have loved to, or still would love to go out on a second date with you, but you were… You know, it’s tough. Dating is very, like, immediate, right? And… And it’s tough when you’re going out of town, and you were, you know, leaving, right? Yeah. And… But we had fun. We had lunch, right? We went to Earth Cafe.
Jess Mah: Yeah.
Ben Bergman: We went to Earth right before New Year’s, and then I was gone for a month or two.
Jess Mah: Yeah.
Noah Berkson: So to bring this full circle, we made this whole podcast just to get you on here so Jess could ask about why you didn’t ask her.
Jess Mah: I know.
Ben Bergman: We’ve been sitting here…
Jess Mah: We’re really trying to make more dating prospects for me.
Ben Bergman: Yeah, no, I mean, we’ve been sitting here talking about sourcing and startup valuations, and now you get to the…
Noah Berkson: We get to the fun stuff.
Ben Bergman: Yes.
Jess Mah: It’s like… It’s… For me, I have met so many incredible people from just dating them that I think so much of my business success has come from just that. If I’m being candid, that is one of the best advantages to being a woman in business. Is that the case at all for you? Has it?
Ben Bergman: You do not hear that very often. Wait, so how do they help you?
Jess Mah: Because I meet very interesting and accomplished, successful people through dating, and because of that, I get to ask them interesting questions. Just like what we’re doing right now.
Ben Bergman: But is it… But, I mean, do you… But sometimes it’s like a mix, right? Or it’s weird to mix them if you’re, you know, go into business with them or…
Jess Mah: No, I don’t do business directly with them, but I learn from them.
Ben Bergman: Okay. Okay.
Jess Mah: And then I hear all the inside secrets on their life and what really happened. Because a lot of these people are very high-profile. I mean, I think I’ve dated five, six billionaires.
Noah Berkson: Wow.
Ben Bergman: Okay.
Noah Berkson: Well, no wonder I’ve been written about.
Jess Mah: And I’m like, so, what’s the actual secret here? What actually happened behind the scenes? And I hear the real stories, and I’m like, wow, no journalist has been able to cover this and has any intel here. And, of course, I’ll never leak it. I treat it just as sensitively as you treat your anonymous sources. And I promise full discretion, because the stuff I’ve heard and know about from these people, it’s just, like, it will blow your mind. And how could you create that without having to sleep with them?
Ben Bergman: But what happened to these billionaires? They sound great. No, I didn’t want to hear those stories.
Jess Mah: Well, some of them are still around.
Ben Bergman: Yes. So what was the question?
Noah Berkson: What would your… Like, how could you do that today? Or, like, how could you leverage this network of people you have in maybe a different way than you’re doing it? Maybe just to learn more about business, learn more about how these people operate? Maybe not for a story, but just more to learn. Like, do you leverage a network in that way or reach out to people in that way?
Ben Bergman: Yeah, I mean, I try not to think of it as, like, leveraging, but again, yeah, it’s, like, always being curious. And one of my powers, I think, is my network and connecting people and knowing so many people, and I think that’s tremendously valuable, bringing people together.
Noah Berkson: How many people do you just reach out to? Not because you want to write a story about them or because it has something to do with your job, but just because you’re like, hey, I want to meet these people. They sound interesting. And… And given the position you have, you have good access. And probably most people would be like, yeah, I’d love to grab a coffee with you.
Ben Bergman: Probably not. No. I mean, if I’m reaching out to you, it’s probably for a story or because you’re a good tennis player or poker player. Yeah. Very few. If it’s just like, oh, I think you’re interesting. Very few. And, yeah, I mean, as far as what you were saying about the dating, too, I mean, I definitely… If I see someone on Hinge or Raya is a VC, of course I’m like, oh, that’s interesting.
Jess Mah: Double duty.
Ben Bergman: Yeah. But I try not to do that to, like, make people feel like I’m interviewing her.
Jess Mah: Well, you’re not actually attracted to her. You’re not gonna go on a date just to see if there’s any business…
Ben Bergman: Yeah. Or people are like, oh, are you gonna, you know, write about what I say? Or, you know, like, you know, write a story on what… You know, if I’m going out with someone from like SpaceX or something, I’m naturally like curious. So that is, you know, what I’m gonna talk about. And I probably gravitate towards people in tech, so a lot of people are in it, but I definitely wouldn’t want to be seen as doing that.
Jess Mah: You have a very good Hinge profile, by the way.
Ben Bergman: Oh, really?
Noah Berkson: What makes it good?
Jess Mah: His photos show him in like very different contexts, and he’s got some great, great photos that show his professional side, and, you know, they’re all very happy, smiley. They’re not too serious. They’re just him. It’s not like 10 other people in the photos. And I don’t know, it’s just a great profile. I remember out of the tens of thousands of profiles I’ve probably seen, his is definitely a top five or top ten.
Ben Bergman: Wow.
Noah Berkson: Wait, who opens on Hinge? Is it the guy that opens, or is it the girl, or anyone can open?
Ben Bergman: Either one. Either one.
Noah Berkson: What’s your opener?
Ben Bergman: I usually try to not have, like, a line because I think that, you know, some people have this, like, catchy line, and I’m like, okay, well, I’ll…
Jess Mah: Go on and see…
Ben Bergman: They just say it. The catchiest line.
Jess Mah: What did Ben say on him?
Ben Bergman: No, but I try to make it organic and, like, about something specific on the person’s profile.
Jess Mah: I think with the messaging was very good too.
Ben Bergman: Well, yeah, because I think it was about your jet. That’s what caught my eye.
Jess Mah: Oh, I took those photos out eventually.
Ben Bergman: You’re attracting… Yeah, but I think that that’s what I opened with. But I mean, I’m glad I had a good profile, but hopefully I always want to undersell and overdeliver because there’s some people who have a great profile, and then you meet them, and it’s so disappointing. So I hope that…
Jess Mah: Well, hey, we’re still here. We’ve been talking for a while, and it’s just like we could talk for hours.
Ben Bergman: We could, yes.
Noah Berkson: One of the things I wanted to ask is, like, you mentioned an article. You said that I love to be a journalist because… Because it’s like having this front-row seat to history, which I really liked. What do you think right now? Or that maybe you’ve covered in the last year or right now, looking forward, what are those things that we’re going to look at in the next 20 years, 50 years that is going to be looked at as history?
Ben Bergman: Well, yeah, I mean, I think the obvious answer right now is AI, and it just happened so suddenly. I mean, I remember I came back from a ski trip last year in Japan, and I felt like when I came back, like I was gone for two weeks. Like, all of a sudden, it’s all anyone was talking about. This was like February of 2023.
Noah Berkson: Niseko. Yes, I was there in February 2023.
Ben Bergman: Really?
Noah Berkson: Okay, that’s… Wow. Should have crossed paths.
Ben Bergman: Yes, we should have. And… But, you know, that is another reason why I love tech too, because it kind of feels like the center of the universe sometimes. And I think it’s undercovered relative to a lot of other things. And there’s just so many interesting things happening right now for AI. And I think it has a lot broader applications than the big crazes of the past few years, which were like crypto and Web3, which were pretty niche. But I just think AI we will be looking back on this period for a long time.
Noah Berkson: Do you feel like there’s anyone, like reporters that don’t respect the coverage of venture and of tech that kind of look at it as, like, that’s not… What’s the important thing on the hierarchy of journalism?
Ben Bergman: Oh, for sure, for sure. There’s a lot of that. And look, I recognize that. But there are far more important things in the world. I mean, there’s reporters who risk their lives every day covering wars and conflict zones. And we need reporters to cover the school board and the county council. And those things don’t get the same sort of resources as tech journalism. And I’m spending my time on yachts and fancy parties with VCs. So I definitely, I get it. But I also think what I do is very important. I think tech is important. I think tech journalism used to be very fawning. It was like, oh my God, Steve Jobs, the iPhone. Look at this cool new product. And then it got very critical, and it was like, we’re going to tear down this company. And I don’t think either approach is good. I hope we find more of a middle ground because I always try to be critical, but I don’t want to be a reporter who… I think there are reporters who just think anything a tech company does is evil or capitalism is evil. And I definitely don’t think that. I think, again, it’s those shades of gray.
Jess Mah: Do you think you might get tired of tech journalism, though? Like 30 years from now? Will you be interested in pivoting and trying some other types of journalism?
Ben Bergman: Well, it’s hard to say. I mean, I definitely am not tired of it because I just feel like, it’s always something new and a new challenge and a new story to tell. But you’ll have to have me back in 30 years.
Jess Mah: Okay.
Noah Berkson: Lastly, have you had any dates off of this? I’m just thinking about this. Have you had any dates where you’ve went on a date, and someone’s just tried to kind of pitch you? Like, you realize that their whole going on a date with you is to kind of, like, pitch you to tell their story of their company?
Ben Bergman: Luckily, I don’t think I’ve had that. I try to… I mean, for one thing, like, I don’t think most people would know, like, who I am. I don’t put that, like, exactly where I work or what I do on my profile.
Noah Berkson: And you still swiped on this?
Jess Mah: Yeah.
Noah Berkson: No context.
Jess Mah: Yeah, I didn’t look him up ahead of time or anything.
Ben Bergman: Wow.
Jess Mah: I just went in totally blind.
Noah Berkson: I feel like those are the power things people put, like, here’s what I do as the way to lure people in.
Jess Mah: I mean, I knew he was in journalism because he had some photos, and I think said something about that for a long time.
Ben Bergman: Yeah. But I keep it vague. You know, I don’t have my full name. I don’t have the publication. And dating apps generally are not the time to be modest. But, you know, you don’t want to, like, put it all out there. And, you know, I remember, like, for a while, I had a clip of me on CNN, but that was, like, too much. So I try to, like, have enough to get them to go out, but not, like, just put it all out there.
Jess Mah: So no photos of you with famous billionaires on yachts and…
Ben Bergman: No, no, I’m not putting my Gulfstream…
Noah Berkson: Ben, this has been awesome.
Jess Mah: Yeah.
Ben Bergman: Thank you so much.
Noah Berkson: Really appreciate you coming. This is fun.
Ben Bergman: This is really fun.