Q&A with Alex Konrad from Upstarts Media

One thing about LaunchSquad: we like each other. So much so that after a recent new client win, they cited our “internal team rapport” as a key part of their decision. But as a distributed team in the post-COVID era, in-person face time is harder to come by. We recently gathered LaunchSquadders in New York and San Francisco to celebrate our 25th anniversary; the NY gathering alone was the single largest in-person meetup we’ve hosted since before 2020. It was a moment to reflect, plan ahead, reset our values, bond with teammates, and engage in the uniquely remote-work ritual of commenting on people’s height when meeting for the first time outside Zoom.

We also invited influential journalists to join us at each meetup, asking them to go deep on the trends of today and what they see as most important in the evolving PR-media landscape. In Williamsburg, I had the opportunity to sit down with Alex Konrad, former senior editor at Forbes, where he spent 12 years covering the startup and VC space (and fielding probably one too many emails from LaunchSquad). Today, he’s the founder and editor of Upstarts Media, a tech publication launched on Substack in February that covers the startup ecosystem from inception to IPO. Since launch, Alex has established an editorial reputation for thoughtful, incisive coverage of the landscape — covering the biggest startup milestones, the darkhorse entrants who shoot to the top, and the latest teams to watch in AI.   

Below is an (abridged) version of our conversation. We went deep on why Alex thinks so many reporters are building their own properties, his method for weighing the plethora of AI startup hopefuls in his inbox every day, and how to pitch Upstarts successfully (hint: it has to do with aligning incentives and absolutely nothing to do with DMing him on Instagram). 

Emily Busse (LaunchSquad): We’ve gone through a few recent eras in journalism: an expansion of properties with the rise of digital media, and then perhaps a bit of a contraction with shifts in ad revenue and shrinking budgets ... and now it feels like a new moment with many reporters starting their own properties — newsletters, podcasts, full outlets. When you look back at this in the context of your own career, what about your trajectory is different from what you expected or envisioned? Or is this exactly how you hoped it would play out?

Alex Konrad (Upstarts Media): It's a real progression or, sort of 180 in a way, because when I started my career, I was as traditional as they come. [...] My first actual media internship was only paying for 2 or 3 days a week at WNYC Radio here in [New York] because that's the amount of days they could afford to pay us. It was $10 a day. I was SAT tutoring the rest of the time to actually live here.

The break in my career was the opportunity to either intern at CNN in Washington, D.C., on a political TV show, or Fortune magazine, interning for the magazine there. My decision was pretty simple: which would allow me to have more impact as an annoying, hustling student? At Fortune, I asked if there was any possibility for interns to write for the print magazine. They said no one had ever done it, but it wasn't against the rules, theoretically. So that became my mission, and I got a 400-word, one-page story in the magazine before I finished the summer. It was about Robert Redford talking about First Amendment protections, an issue really important to him with Sundance, to protect a documentary filmmaker who was getting sued at the time by Chevron over his documentary on the Amazon rainforest pollution.

Basically, I joined Fortune right after I graduated from college, and I was like, “I'm gonna work my way up through traditional media.” After a couple of years there, I got to Forbes and worked my way up from literally the bottom of Forbes to our most senior tech reporter. I was like, this is great. 

But then I think me and a lot of my peers, we achieved some of those goals, and we were like, is that all there is? What's next? The pace sucks, we’re writing similar stories over and over, and we've hit a ceiling for growth. 

You're seeing a moment now where journalists are starting to feel restless or get an entrepreneurial spirit that, when I started out, would have seemed crazy. 

EB: In the Q&A you did with Hunter Walk recently, you said something that stuck out to me. The quote is, "I can't speak for every reporter, but the tech versus media narrative is usually wildly and cynically overblown." We talk a lot about this with our clients. Don't mistake a shrewd question for an attack, and don't lose an opportunity to tell part of your story by going defensive. Can you expand on what you meant in that moment, and how you now balance your journalistic responsibility with the need to build trust with your sources?

AK: With the whole ‘tech versus media’ narrative, there are a couple of very basic things that I think about. First is, I do think there was an over-exuberant moment where media was kind of rah-rah cheerleading the tech industry. I think Upstarts focuses on startups and tech leaders who are punching above their weight, trying to have a positive impact, which is a subset of the tech industry today. That is why we say we want to cover inception through IPO. I can go early, I can talk to folks who are not getting all the attention, and part of why I wanted to start my company was that I was really bored by the idea of joining the Elon Musk beat, or just writing endlessly about new releases from OpenAl. Sure, that journalism will exist, I'm not saying it has no value, but I also see it as a commodity and just not that interesting to the ecosystem.

With this industry, like 10 years ago, it was easier to think that maybe the whole tech industry was all startups. At least that was sort of the mindset: they're all challengers, it's all interesting, it's all fascinating and great, and let's take them at face value on what could be possible. Now it's more nuanced. There has to be balance. There was a natural pushback by publications like my former employer, Forbes, The Wall Street Journal, etc., to be a little more critical, a little more incisive. Let's think about the real user ramifications. I think Cambridge Analytica and some of the stuff that happened with Meta was a real eye-opener for people about how this could impact millions of people. And so, I think there was a natural correction.

From the startup side, from the tech side, people were like, "Well, why are you suddenly being jerks to us? What changed?" They were expecting a very positive and sort of cheerleading press. And I think in the tech industry today, some people still want that to come back. You see venture capital firms and startups trying to launch their own publications, and basically be like, there isn't enough cheerleading, you know, everyone's too cynical. I think, as with most things, the truth is somewhere in the middle. I think there are still plenty of positive coverage in traditional media.

I found that often the most acerbic and antagonistic people on social media are very meek and polite and nice in person. I think there's a bit of play-acting or posturing, but I also think people have decided that there is business value in saying, "Trust us, don't trust anyone else who might not say what we like, listen to me directly." The Go Direct movement has very clear incentives, and Charlie Munger's comment, "Show me the incentives, I'll show you the outcome," I think really applies to this whole narrative of tech versus media. At the end of the day, my wife is a VC who invests in consumer companies. I have friends who are founders who work at startups. I don't wake up in the morning imagining myself other than all of them. We're all just people trying to get through the day. And I think that's true for most reporters, and I also think it's true for most tech people when they actually stop and think about it.

EB: Unpaid coverage is often referred to as “earned” from a tactical perspective, but it also does speak to the fact that it does feel more earned, more credible, when there is an arbiter of this space (a journalist) who is talking to you and telling your story from an objective perspective. Do you think that’s still true?

AK: I think there's two levels of that. I think there's earned media in the sense that you've been put through the paces, which is what we hope to do. I think it's really healthy for a startup, or even a bigger tech company, to have that kind of shock therapy of, "Well, we thought that everyone would care about these things with this launch. What are these other things? This is feedback that we did not anticipate.” It's very different from marketing. And then I think there's also earned media in the sense of anointing or creating the nice headline that people want.

I understand that game, and I think with Upstarts, we have to compete against it. I'm only publishing 8 to 10 stories a month, usually, and so every one is pretty in-depth. I just say to founders straight up, “If you want a 400-word, hard-paid-up story in Bloomberg where all you're gonna do is screenshot the headline at the top and post that on social, and you don't care if anyone ever reads the story, I'm not gonna try to convince you not to do that. Maybe that's the end result you want. But if you actually want people to read the article and enjoy it, thumbs up.”

EB: In an interview from when you launched Upstarts, you said, "We're in a moment where so much tech media coverage is focused on big tech politics, big policy debates, but not so much on the startups I love to write about. It was hard to get those founder journeys out there at the time, and I'm hoping to do my part to tell those stories." When you announced Upstarts, a lot of us at LaunchSquad, especially on the B2B side, were excited about it. It feels like it has been harder in the last few years to find earned opportunities for legitimate articles that go in-depth on startups from an unpaid, journalistic view. Why do you think it that is, and do you feel like that initial mission is proving out so far?

AK: Yeah, so this is a really meaty question. I've been thinking a lot about this as I reflect on the first 6 months, and we're going to be doing a reader survey soon. I think there are a couple of interesting competing points happening right now. 

One is there is just a raw, higher volume of startups and tech news out there than ever before. We flooded the zone with funding announcements, with launches. I mean, at Forbes last year, I felt like I had written every unicorn funding announcement I wanted. The numbers kept getting bigger and bigger, so the bar just kept getting higher for what would impress me. I could have written new funding announcements or startup launches every day and still been behind. So I think the volume is just a real problem.

Then the other question is, how do we value this news? This is where I've been really grappling. In my experience, startups are desperate for Upstarts to write about them more often than not. The great professionals they work with are excited to bring those stories to us. Where I'm still not fully sold is that I can convince all of you, or these startups, to read about each other. These stories have a pretty high floor, but a low ceiling, from what I can tell. If you think about media as a revenue-driving business and a hits business, it can be tough, because it's rare that even the best startup launch from stealth and funding exclusive will actually go viral or drive meaningful subs.

If I look at my stories that are the most trafficked or drove the most paid subscribers, they were still kind of the stories that you'll hear founders complain they don't want to see more of, like scoops or more investigative pieces. I did a piece scooping that Meta was partnering with Midjourney, or I did one about a secret startup in the UK that was gonna do missiles and raise $100 million. Those stories drove a ton of readers. 

And so I think the challenge I have, and I put to all of you as well, is how do we find a way to get people to vote with their eyes and their attention and their dollars to help those smaller stories? Because I think they're really important. I know you guys do too, and every time I write an in-depth story about a startup, they love that they've gone through the process, they want to share the story. My word of mouth is really strong. But I think the reality is that if I were just trying to be top-of-funnel growth, I would not lean into those stories as much.

EB: We should talk about Al, because I feel like we have to. We just did a summary of our newly signed clients; I think all but one is using Al in some capacity. I know you have said you love Granola—and it's a big hit here with us too—but are there any that you don't love? You don't have to name names; it could just be a use case you think is not quite there yet.

AK: I still don't believe that the writing tools like Claude or ChatGPT are actually better than me at structuring or writing a story. I don't think that'll necessarily last forever, but I do think that today, if you were a skilled, experienced person at writing a marketing email, or a pitch, or for me, an article, I still think these tools are just raising the floor, not the ceiling. It allows someone who is not a journalist to fake that they're a journalist with a fake blog post. But they all kind of look the same. They all have these little traits that I think are still the uncanny valley, where you see it, and you're like, "Oh, this feels like Al-generated content."

My feeling is that there's already thousands of articles out there that no one is ever gonna read, and so I can only win if the curated, small number of articles I write really feel like me. People ask me all the time, ‘Do you use ChatGPT, do you use Perplexity?’ I will use them occasionally for a little bit of research, where I still have to trust but verify, so it doesn't save me a ton of time. But yeah, for now, my process is still pretty analog, in the sense that I'm writing in Google Docs, but I just don't think it's there yet.

EB: We're constantly navigating this balance, especially with the Al agent boom. On one hand, it can feel like you are saying the same thing as everyone else to reporters — and I’ve gotten that feedback directly, of "Hey, because you said 'Al agents,' I'm out.” You get lost in a sea of pitches. But at the same time, if you don't talk about Al, it can sometimes feel irrelevant. In the AI space, stories have to be so specific and so timely to cut through. How do you weigh stories in the Al world? Does it have its own set of criteria since it is so saturated, or is it just part of your overall calculation?

AK: Reporters have themes and beats that they care about, and trying to hit those is always smart. But if it feels forced, it's a miss. Injecting Al into the pitch makes sense if you're writing to my former colleague Rashi Shrivastava, who writes the Al newsletter for Forbes. Her question is, "What will I put in my Al newsletter?" So if you don't say Al, that is probably a miss. But someone like me is writing about the wider startup ecosystem. I'd say probably 60% of my stories feel more Al-focused right now, but I'm not like, "Oh, this was not an Al startup, I'm not gonna write about it." 

Authenticity is really important. For me, it's about the bigger trend that a startup is tapping into. Why would people plausibly care? With my story this morning, it's a security startup, but it's about securing Al agents because they're gonna run amok. That feels very comfortable. So that's sort of an Al story, but it's also a security story. But if it was just a security story, I wouldn't want them to be like, "And also Al!" You know what I mean?

EB: Yes, we’ve seen it become increasingly important to counsel clients about talking about AI in a way that’s authentic and truly central to their story or product. When it's intrinsic to what they're doing, it's a much more solid story.

AK: Yeah, one trick I've done with founders is to say, "Take out all references to Al and your Al products. Do you still have a company that you think is winning? Is it still interesting?" If you can have a whole conversation without it, you are not an Al company. You maybe have Al features, you're Al-enabled. If you literally can't talk about your business without talking about Al, then maybe you're an Al company.

EB: Do you have any specific advice for pitching independent journalists? You've talked a little bit about paying attention to beats and staying authentic, but anything else you would add?

AK: I think you still have to bring layers of context to an independent journalist; it's just now much more focused on them and their little business. For Upstarts, it's like, "We can see Alex is writing a lot about these topics. We can tell that he has no time. So how do we help him grow his subscribers, which he's trying to do, while writing a cool early-stage startup story that just feels good for the Upstarts brand?" That's how you would best pitch me.

My top advice is, if it feels like a stretch, just don't do it. I just don't have the luxury of writing something as a favor to somebody. I hate when I have to have that conflict with somebody and just be like, "Come on, if you were me, would you take this pitch?" And they're like, "No, but maybe?"

EB: When do you feel like a pitch is particularly sticky for you? Can you give a specific example?

AK: A pitch that can present the case for why this will drive the conversation with the Upstarts community and feels relevant is sticky. A pitch that can matter-of-factly say, "Here's the scenario where I think this is a win for you guys, and here's why we're excited about it," that's helpful. The extra bells and whistles kind of cost me time. Just cut to the chase. I don't need five or six paragraphs. I need bullet points: Here's who they are. Here's why we think you would be excited. Here's why we're excited. And then even better, "We can be flexible with you on the timing." That is probably the number one thing. A pitch asking, "Can you write about this company for 7 AM tomorrow morning?" That's a no.

EB: Okay, before we go to audience questions… quick lightning round. Rate the following from 1 to 10. One being “doesn't matter,” or you're not that excited about it. Ten being "this is important," or you're into it.

EB: The ‘AI supernova’ as the new unicorn.
AK: 8, but not necessarily for why you would think.

EB: Exclusive pitches. 
AK: 10

EB: Embargoed funding pitches: 
AK: 7

EB: Tech leaders as politicians.
AK: 5.

EB: Celebrities as tech leaders.
AK: 3.

EB: Founders announcing news on X or LinkedIn as the primary channel. (aka Going Direct)
AK: Neutral 5.

EB: A cold email pitch from someone you don't know.
AK: 5.

EB: What about a cold phone pitch.
AK: 0. And please don’t DM me on Instagram. That’s -10. 

EB: Vibe coding. 
AK: 5.

EB: In-person briefings.
AK: Really depends, so nets out to a 5.

EB: The AI wrapper / AI-washing conversation.
AK: 4.

EB: Decade-old companies refounding as "AI native."
AK: Potentially … well, it really depends. I accepted a pitch on a company that is otherwise not super famous or exciting, but they're giving me all their numbers on how much they had to pivot and throw away revenue to rebuild. I think it'll be interesting to the founders just for the numbers, not really for the company itself. So in that sense, that one was an 8. But they can easily be snoozy. 

EB: The return of the in-person tech conference.
AK: 6, trending down.

EB: The Forbes Midas List.
AK: 7. Still the best option.

EB: OK, thanks for indulging that. We’ll take a few questions from the audience. 

Audience Member: Your response on supernovas had an asterisk… can you expand on that?

AK: Yeah, I think it's really interesting to just see how startups now fast-follow on to, like, a couple, like, any tactic they see really seeming to resonate from a marketing standpoint. So there was the Clooney video-type announcement, and sort of seller lifestyle. A bunch of startups, especially on the West Coast, piled into that. I think you're also seeing this trend of, being the “fastest revenue of all time,” and, “we are the craziest growing company; we had 100 million revenue before we even started!” And I think that is the race to the bottom as well. 

The whole supernova thing is really interesting, because, on the meta level, clearly this resonates with people, and I'm curious why it matters. And because I'm also just very curious how sticky all of this is. I’m almost the ‘BJ Novak takes notes GIF’ from The Office. Every startup is like, “We're a supernova, we're growing faster than ever,” and I'm just like, “Yep, let's check on  them in a year.” Maybe it’ll be really great, but maybe it’s, like, WeWorky? And I covered the rise and fall of WeWork, so I know what that looks like.

Audience Member: What reporters or outlets do you follow regularly and trust for news?

Alex Konrad: I do have an aggressive newsletters tag of traditional and new media that I read every day, like Newcomer and Big Technology. I also read a few newsletters that are not tech-related but just help me stay up to date, like After School, Feed Me, and Embedded are three that come to mind. I get The Information alerts; I love a couple of the reporters there still. I tried to hire them when I was back at Forbes. Now I encourage them to go independent! Same with a couple of reporters at Bloomberg. Basically every publication there are three or so reporters that I follow closely on social media and will read most of their work. [...] But I would say I usually don't go to the homepages of news sites anymore, not even The New York Times or Bloomberg. I get my news from social sharing or newsletter digests that are like, ‘this is our big story of the day.’

Audience Member: Business Insider recently announced they're going to let reporters use Al for the first draft of their stories. As models get better at writing and more people are using Al for first drafts, what does the role of the writer become?

AK: At a place like BI, the writer becomes more like a social media manager, handling the posting and the prompting. It feels much more like marketing, much less like journalism. The only possible excuse is that a lot of journalists are very inexperienced and young right now, and if your client is talking Al to a 23-year-old who's gonna make basic mistakes from lack of training, maybe the Al first draft actually patches some of those mistakes. But that is a low bar to clear and not very inspiring. I think we're going to see a bifurcation between curated craftsmanship from established folks and the majority of journalism trending towards commodity and bullet points — kind of like Axios did before Al. And the saddest thing is that a meaningful number of readers do prefer that. Attention spans are down.

Audience Member: My clients are VCs. When you're writing about one of their portfolio companies and get on the phone with the VC, what types of insights do you actually want to hear from them?

AK: The number one way a VC can develop a good relationship is to be willing to push the startup to share more than they would otherwise, or to facilitate on background. I will often ask VCs, "Can you push them on sharing valuation or revenue numbers?" It's better to just share the numbers than have a scoop come out later. 

I will also ask VCs for a gut check: "When you did diligence on this company, what were the biggest risk factors, and how did you get comfortable with it anyway?" The startup might be less comfortable saying, "Here's why people say we suck," but the VC can address it. Journalists hate to feel like they missed the big picture on something. It's a horrible feeling to publish and have someone ask, "Well, did you even ask about X?" and you're like, "No, I did not." Better to talk about the tension or the rebuttal upfront.