When I ran the Cloud 100, there were a couple unnamed cloud CEOs who had the very fancy Elon-level security, and I was like, 'You are not Elon. I get why Elon or Sam Altman has intense security. You are not those guys.'
Alex Konrad has spent his whole career deciding which startups the rest of us hear about. Then he went to Forbes in 2012. In February 2025, he left to start Upstarts Media. What is the number one trait that you see from the most successful people you've interviewed?
The founders who are almost...
If you've built a company, raised a round, or written a check in tech over the last 15 years, my guest today is the person you wanted covering you. Alex Konrad has spent his whole career deciding which startups the rest of us hear about. He started at Fortune in 2010 covering New York companies like Foursquare and Zocdoc, back when tech coverage still basically meant Silicon Valley. Then he went to Forbes in 2012 and stayed more than a decade, writing all kinds of cover stories on people like Marc Benioff, Frank Slootman, the Collison brothers, and many more. He ran the Midas List for 10 years and co-created the Cloud 100, which means for a stretch there he was ranking the industry as much as covering it. In February 2025, he left to start Upstarts Media, independent on his own. Since then, he's built a Substack, a live events business, and the Upstarts podcast. He sat down with people like Melanie Perkins of Canva, Winston Weinberg of Harvey, and Jesse Zhang from Decagon. He is building the media company of the future. I've known Alex for over a decade. I followed his work the entire time I was building BetterCloud. And I'll admit it, I begged him to cover me more than once. Um, I have a lot of respect for someone who leaves a great seat to go build something on their own. And I've been looking forward to this conversation for a long time. Alex Konrad, welcome to Not Another CEO Podcast.
Wow, thank you so much. I'm pumped now.
Um, okay. First question out of the gate, a little different than I asked most of my guests. For you, first question is, how do you decide who to cover?
Yeah, so it's changed a bit over my career. You know, a lot of people in media, they start with a niche or a focus. And for me, I had to pick one that no one in Silicon Valley was covering. And so that was adtech. So for a minute there, I was all about the New York adtech people. And then I kind of evolved to cover the most interesting sort of big names who weren't yet a household name in tech. So you mentioned Melanie Perkins, um, the Whiz CEO, like some of these folks who were about to go public or about to get acquired, you know, but hadn't had a ton of coverage. That was what was most exciting to me at Forbes. Now at Upstarts, I'm looking for a sweet spot of, you know, a real upstart mindset founder, someone who's taking on a really big industry or they have a crazy swing technology and they have a bit of validation. So, I know it's more than an idea, but I can go earlier and bet on someone maybe if it's, you know, the first article ever written about them.
And you, how many pitches do you get? I mean, it must be a lot. I have one of those email inbox agents that is looking at my pitches and giving me like the top five each day because it's probably more than 20 a day.
Yeah.
And so, and how many do you cover in a week?
So I have some help at Upstarts, but I am still the only writer, editor, podcast host. And so it's a real challenge. You know, when we're in season, I am, you know, doing a podcast once a week. I'm trying to write at least twice a week and I'm sometimes doing events and stuff like that. So to do more than two articles a week really strains the care and the effort I want to put into something.
And one of the things I noticed even when you were at Forbes and today, I talk to founders about this a lot, like a lot of the tech media, it became so transactional that the quality, and I'm talking about even 10 years ago, whatever, and still today, the quality of the content and the quality of the stories was just so, I felt very surface level. And I think that's one of the things that I always looked at your stuff and still today, and it's you go the next level.
I try. I mean, it's partly because I, as a craftsperson, want, I'm passionate about wanting to make the best product I can, right? And I don't feel good having to put something out there in the world that I don't think is the best version of that thing. But of course, running a business, sometimes you have to make trade-offs. And, you know, the extra 10% of quality that costs 50% more time is not going to make sense. So that is something that I grapple with, honestly. And I think another thing that I can't stop is that I just have a love for the game. I just love doing it. So I work probably way harder than I need to. I work all the time. And I take it so personally. You know, part of my brain is like, I should be covering every startup piece of news that matters in the world. I can't possibly do that. And so I have to kind of tell my brain to pump the brakes sometimes.
Um, we were talking before, like media has changed a lot. Um, I mean, when I started working in tech, it was TechCrunch was kind of the outlet, and if you got a TechCrunch article, I remember getting my first TechCrunch, I sent it to my parents, I sent it to all my friends, like, you know, that was the thing. And to be honest, nothing against TechCrunch, but I haven't read TechCrunch in years. I mean, I literally have not visited the website in years. And I feel like it's just changed a lot. There were so many outlets for a long time covering tech. I mean, in the peak for me in that 2010, 2015 kind of that window of time, I mean, there were so many people covering it, and it feels like it's gotten less and less. A lot of the brands that were around, they kind of went to the wayside. And like, you've been on the other, you've been in it, you know? So what are you seeing?
Yeah, there's a couple ways I think we could take that question. One is more meta, and that is that I do think we are in this very fragmented information environment where one thing that kind of always bemuses me is I'll see on social media someone complain, 'Why is nobody talking about this thing? Why has no one written about this or looked into that?' And more often than not, someone in the world has done that. It's just you didn't see it. And this is something that I see firsthand, especially with Upstarts now. I will write about something and I just can't get in front of everyone that I wanted to. I'll get in front of some people, of course, otherwise I wouldn't be operating, but so many people who I think would benefit from that article just never see it because the algorithm doesn't show it, because they just aren't getting exposed to Upstarts. Maybe they even subscribe and I'm buried. They got 20 newsletters that day and they just never open that one. So there is a challenge of just getting in front of people with things. But I think the reason I thought of this is because you mentioned, 'Oh, TechCrunch, where is it?' You'd be surprised when I do my research on really cool companies that I want to write about. A fair amount of the time, not every time, but a fair amount of the time, one of the only outlets that has covered one of these up-and-coming startups is TechCrunch. And I cite them and I link to them. And I also maybe never saw that article. So if so, I might go in saying, 'Oh, no one's ever written about this company.' And then I'm like, 'Oh, last year actually TechCrunch did do a piece. It's just we didn't notice.'
Some people obviously did, or they wouldn't change an operation.
So I think that's one thing, is there's just all these little echo chambers and sort of fragmented silos where some people might be getting information and you and I just never ever see it. So that's one thing I have to deal with. And it's also, on a personal note, it's humbling as a founder because I still get messages from people who have also known me for a decade who are like, 'Wait, are you doing a new thing? Like, what is it?' And I'm like, I've been doing it for over a year now. I talk about it as loud as possible. Like, where are you? But you have to understand, for whatever reason, they just haven't engaged with my work. They didn't see my LinkedIn post or whatever. And so now I have an opportunity to re-explain who I am, right? But you're like, wait, am I screaming into the void? Why is nobody seeing that? And so I think that's one piece of this. Then I think also there is a disconnect where a lot of tech media right now is being written either by non-journalist insiders for other people on the inside, or it's reporters from the outside writing for a general business audience or populace that is not in the tech industry that might even be very skeptical about things like AI. And unfortunately, there's a lot of business reasons that I think those kind of diverge. And so if you're in the tech industry, you're like, 'The only press coverage about startups or about AI or whatever is so negative, right?' And then, what do I want? I want the VC podcast or whatever that talks about how awesome it is. Upstarts actually tries to play in the middle where we try to be still very journalistic, fair, asking the hard questions, but also I'm a founder. My wife, you know, works at a startup. These are my people, too. And so I'm very empathetic, but also still being a journalist. And sometimes I'm like, you know, hey, if I'm going to beat myself up to be in the middle there, I would love everyone to see it. Which goes back to the beginning, right?
It's, um, I was actually talking to people here at the podcast studio before we came in, and we were talking about the algorithm and playing to the algorithm. And that for me is one of the things I've been most frustrated with. Same thing. It's like, do you want to play to the algorithm or do you want to actually create the content that is the high-quality, in your case, journalistic, you know, really good quality content, but it may not be the hypey thing that exactly hits that, you know, that fast-moving kind of algorithm. And that's a really, I mean, to be honest, that's one of the reasons that I went, I don't post very much on LinkedIn. I do sometimes, a couple times, you know, maybe once a week, whatever. But I stopped doing it at the volume because at some point it was just all tied to the algorithm. And the algorithm has changed to the point where it's like if I don't hit that right hook with the right thing, it only gets served to, you know, 10% of my 20,000 connections or whatever followers. Whereas on Substack, that was one of the reasons I like Substack is at least you control the, at least you know that the audience will receive it. Now, will they read it or whatever? That's different, but at least you know you can push that.
Yeah, I hear you. For me, it's a constant push and pull. I would say that Upstarts is trying to lean in earlier and take more of a chance or more of a stance on technology and founders. Like I said before, they maybe have as much validation. And so we will write about companies coming out of stealth or new products. Like I will play with apps or hardware devices and be able to be one of the first people to talk about it. And I think that is so fun and important. At the same time, if we only did that, it would be limiting for Upstarts because those big names, those big AI labs, you know, they do draw in a lot of people. And so there's a real kind of balancing act for me, almost like the old joke about Hollywood where it's sort of one for me, one for you, where they would make the artistic, you know, indie film and then they'd make the blockbuster. I have to on some level think about a balance like that as well.
Um, what did you feel was the move to start, because it's a big thing to start your own media company. Um, was that move because of who you wanted to cover? Was that move how you want, like, why did you do that? Why did you leave Forbes?
I'm a very intentional person, um, to a fault. You know, I'd say my wife is the fast-moving, join the new startup, you know, bounce around the industry, um, very decisive person. I'm the one who has the decision tree mapping. If I do this, I do that, you know, this is what happens, three steps down. I blame growing up, I was a competitive chess player. And so a lot of time, actually more time than you're actually playing, you're just analyzing. We called it kibitzing. You know, you'd be looking at, okay, if you had done this move, would you have been in a better position, or were you expecting them to do that move and then you were going to do something else? And it's a lot of kind of counterfactual role-playing of like what could have happened with this board. I kind of think about life that way in a lot of ways, maybe to a, you know, I'm like, 'Oh, if I had made that decision six months ago for a partnership, where would I be today?' And people actually tell me like, at some point you have to stop. You have to just move into the future and not obsess about the sort of past decisions. Um, I think why I bring this up is because I was tempted to leave Forbes many times over the years. I think anyone who spends more than a decade in a job has those moments. Why did I stay? I loved the team. I loved the, you know, doing high-impact work. We won an award the year before I left for our coverage of Sam Altman's brief firing and rehiring at OpenAI and the Silicon Valley Bank crisis and all this stuff. And it felt like I'm on the pulse doing work that matters, reaching a wider audience. And I felt like if I left Forbes, I'd lose that wider platform and accessibility of the work because so much of our work was also not under a huge paywall. Um, at some point though, 15 cover stories in, we don't have a podcast studio. Um, and I just look at the future and it's like, okay, I could do a cover story about Sam Altman. I could do a cover story about the Anthropic CEO, Dario Amodei. I could do one about the next AI person. You know, maybe I go after Elon Musk. But you could kind of just almost play by numbers what would be next for me. Um, and I'm sure this is true in other careers, too. It's sort of like, how do I top what I just did? The decision tree can look narrower and narrower unless you just blow things up, flip the board, start over. And so that's kind of where I was from a career standpoint. Then when I was thinking about what do I want to do, I just thought it'd be so much more exciting to build something from scratch, be an entrepreneur, control my own destiny versus go run it back and have, you know, some other media company say, 'Do another Midas List or do another Cloud 100 list. We want you to do the Sam Altman cover story.' You know, that wasn't that exciting to me. No offense, I'm sure I would have done a very fun Sam cover story, but just I could almost just see it in my head already. There wasn't going to be anything surprising or exciting to me. And with Upstarts, I think the challenge is, can we make startup news relevant, sustainable? Can we build a community that cares about that 99% of companies and founders who don't get the cover story?
Right. Right. What are you looking like when you're actually talking to a founder and you're going to cover them and no one's covered them before, or maybe some small article? What are you trying to... I'm asking this because like I feel like at least thinking about my conversations with you was like, okay, back then in BetterCloud, I'm like, I got to sell this guy. I got like, you know, like how do you have those, how do you get to the real meat of it because you're about to publish a, it's a big deal for that founder and like how do you get past the first like layer, that first filter?
One framework I use is I almost imagine an article as an argument. So it's sort of like I am giving a three-minute, whatever it takes to read the article, let's say three or five-minute argumentative speech to you to get you to care about a technology or to get you to learn about a founder, right? Or something. I could lose your attention many times over those three to five minutes. Are you giving me the materials, the hot takes, the exciting technology that will keep my attention enough to then keep everyone else's attention? And so this is something that I'm always thinking about to some degree. Do you have any numbers or customers or momentum that gets our attention? Do you have technology that is inherently interesting, or if not, is it such an important market or sort of just high-impact area that we can make something boring seem interesting? Do you have a compelling personal story? Does your company have a compelling backstory? Did you pivot? Did you stumble into this in an interesting way? Did you get crazy bad or good advice? All of these are the ingredients that allow me to tell that argument. One thing that I see in bad writing that I try to avoid myself is when an article feels disjointed. This could be your own blog post. I'm not saying you specifically, but any founder in their personal writing or in an article. Every sentence has to count, has to build on the previous. So we are telling one story, one argument, and all it takes is one disconnected or boring piece and people check out. You know, that's why if I'm being really boring on this podcast, I'm counting on you to move me along fast so that we keep this audience compelled. Does that make sense? So I will see something and I'll be like, why is, you know, that's a whole different article or that's a whole different point that shouldn't be there. And so how this is tactical for a founder is I want those ingredients given to me. I want more ingredients than I could possibly put in one story so you can trust me to figure out how they fit together. And that's where the magic happens.
When all the, you've interviewed, so like really the biggest of the biggest names and then all these upstarts now, what is the number one trait that you see from the most successful people you've interviewed?
You know, I think that there are obviously exceptions, so I want to caveat that, but I think that the founders who are almost sick in the head because they just have a love for the game and they are building not for wealth, not for Twitter popularity, but because this is all they know to be doing and they couldn't live with themselves if they weren't still working on that company. That is usually the trait that I can just see and say, 'Okay, if I were an investor, I'd put money with this person.' Or if I were looking in another universe to have to work for someone, I'd want to work for that person. It is often the CEO who I think is like, this market seemed like we could make a venture-backed business, or I saw another guy doing this and I was jealous and I thought we could do it better. Um, or I want the lifestyle, you know, I wanted to go to YC, I wanted to be anointed a leader. Um, I just feel like those people are the ones who over-raise when they can, over-hire when they can, get into Twitter fights when they should be, you know, focusing on their business, and I think they burn out faster.
Yeah, I've asked a couple of people this question. Um, one of them was Adam Bryant from the New York Times. Well, not anymore, but who wrote the Corner Office, and he talked about this, you know, it's like it's the thing around founders need to have that obsession, something a little sick, you know, because it's a terrible, it really is such a hard journey. And I like that you say that because I think that that is the thing. And I do think when we get to these like the peak of bubble, which I believe we're in today, you end up with all these people jumping in the game to be a founder when they're not built for it. And we've seen multiple cycles of this, right? I mean, when I started covering tech, it was not nearly as cool to be a startup founder in 2010, I would say, broadly speaking. You know, I went to an East Coast Ivy League school and going to tech was getting a job at Google or Facebook. You know, that was exciting. It wasn't like everyone wanted to be an entrepreneur. Now, you go back to those schools and there are so many founder programs. There's Dorm Room Fund. There's like, you know, you could raise all this money and have a business before you're, you know, in your second year of college, right? And it's just completely different. So I think we have seen cycles there. Um, you know, there have been also moments where, you know, a bubble bursts like, you know, the ZERP era and suddenly, you know, it's harder to raise and people are like, 'This isn't fun anymore.'
So I definitely think it can, you know, it's not great to just be doing this because you see everyone else doing it.
Um, part of why I also give the answer of the love of the game is because I do think that it can be hard to get too specific after that without having survivor bias and being like, 'Okay, well, this worked for Frank Slootman, it's going to work for you, or this worked for Melanie Perkins, it's going to work for you.' You know, Frank, I don't know if you've met him, but like he's a very Dutch CEO. He kind of can be a little bit of an, but he was so effective and he was your classic hard-edged sales guy. You know, he told me things like, you know, if people are trying to talk smack about each other behind their backs, I just bring them both into my office and I'm like, duke it out in front of me. I want full transparency. Which you could say, okay, maybe that's really effective. If I were a CEO, I might be like, well, this also sounds disruptive. What if we just didn't have any funding? Um, but you know, his advice, like I think the best advice he ever gave that I heard was, um, he always wanted to be close to the engine room of the business. So whatever is really making money, driving the business forward, or, you know, creating the product, he wanted to be as close to that as possible. That's great advice, but of course we can find exceptions. People who were a designer or something and then they built an amazing tool in that space, you know. Um, this, you have Notion, Ivan like famously goes to Japan and like gets into streetwear and like has this cultural immersion in Japan and comes back massively informed to really build Notion. So I'm not saying everyone should go to Japan either, right? I think maybe one other common trait that could be widely applicable is I do think that you should be trying to cultivate one superpower. Like I think there should be one thing that you as a CEO or a founder can do better than anyone you can hire at least early on. If you can hire an all-star team who are better than you in every way and you almost just become a little obsolete there and you're more the vision and the face, like that's probably a great problem to have. And I think we both know modest founders who would say they've gotten to that point where they're like, 'Everyone here is smarter than me.' And that's a great problem, but early on when it's harder to sell what you're doing, harder to get people to believe in you, I do think a founder should be able to sell their product better than anybody else because they know it better than anybody else. I think they should be, you know, arms rolled... sorry, I'm sorry. They should be...
No, I was going to say they should have their sleeves rolled up.
Oh, yeah. To know their product, know how it works, be able to do customer support, like actually do those things. And then I'd be curious how you would answer this, but like for me, um, I'm better at sales than I thought I was, but I'm still, my 10x engineer equivalent is storytelling. I really think that I can just tell a better story faster, deeper than the average person. And even if you put me in front of a bunch of other great journalists, I believe I could write that 2,000-word in-depth piece 10 times faster than most of my peers. Like because it just clicks in my brain, and it is a superpower. I'm not saying I'm the best, but I do think I am really freaking good at it. And I think every founder should ideally find something in their business where they're like, 'Yeah, I'm freaking good.'
I agree with that. Especially, like you said, especially in the early days, something that separates them. I actually didn't, when I was early days of BetterCloud, I didn't even appreciate that this was my superpower, but as time has gone on, I think it is my ability to motivate people.
There you go, that's a huge one.
You know, and I didn't even think that was it. And now as I reflect, like getting people excited, my wife says I'm like Chris Farley from the, you know, living in a van down by the river. She's like, you get so amped up and, you know, you get the people going and through the tough times and through this and making people believe that we're going to get there. And so I didn't appreciate that. And I'm like, I'm actually not great at any other, I mean, I'm good at some stuff, but like that actually is the superpower.
