S12E7: From Tech Reporter to Media Founder with Alex Konrad, Founder of Upstarts Media

So much attention right now, whether it's from social media or traditional press, is focused on politics and big tech and only a couple players in AI. I like hanging out with early-stage companies too. I think the stories of founder journeys are really important. And so Upstarts really gives me the flexibility to go from inception through IPO, trying to share that sort of high-signal story that I think matters for this audience.

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Welcome back to The Room Podcast. Today we're excited to take you inside the room with Alex Conrad, longtime Forbes journalist and now co-founder of Upstarts Media, a new venture reshaping how early-stage tech stories are told. For over a decade, Alex has had a front row seat to the defining moments of the startup and venture capital world, including interviewing leaders like Satya Nadella, Sam Altman, the Collison brothers, and Masayoshi Son. From launching the Cloud 100 and editing the Midas List to helping shape the cultural impact of 30 Under 30, Alex's work at Forbes has left a lasting mark on the tech media landscape. Now with Upstarts Media, he's stepping into the founder seat to build a modern community-first media company. Think live video, curated events, a new podcast, and a sharp focus on the builders, investors, and stories that are often overlooked by legacy media. In this episode, we talk about what Alex has learned from being in the room with some of the most powerful people in tech, how he's thinking about the future of editorial in an algorithm-driven world, and why he believes conferences as we know them are dead. Madison McIlwain and I walked away from this conversation feeling both energized and deeply curious about what comes next for the future of tech storytelling, and we're so excited to share it with you. Let's open the door.

First of all, Alex, thanks so much for joining us in The Room today.

Yeah, thanks for having me on.

We love to start at the beginning with all of our guests, so we're curious, where did you grow up and how did that shape your view of the world?

I grew up in New York City, like actually New York City, not when some people claim that and they grew up 30 miles away. So I grew up on the Upper West Side of Manhattan and I loved it. In terms of how it shaped the world for me, I was taking the subway and mixing it up with different people at a very young age. I think it made me unfazed by a lot of things because I was wandering St. Mark's as a 14-year-old exploring a lot. I think it made me curious and self-sufficient. And then I've always loved New York for just being very no-nonsense. So even now as a tech reporter and someone who's in the tech community here, I like how we can meet at a coffee shop and not be the big game in town. No one really cares about a funding round or something, whereas you go to San Francisco and it's like everyone's spying on each other. So I, I love that New York vibe. No, that's Great.

And the curiosity thread definitely makes sense given what you've done with your career. In that vein of early identity, did you always think you would become a founder?

I didn't think I would be a founder necessarily. I wanted to be some sort of storyteller bringing info to the world in different ways. For a while, I thought maybe I would be an author. I thought I might be a foreign correspondent. And then in college, I was actually playing with the idea of being an archaeologist. So my major was like stitched together as the Indiana Jones major before I realized that in real life, Indiana Jones would probably go to jail pretty fast.

Yeah, that is probably true. It's funny you mentioned college. Of course, you went to Harvard for undergrad. Go Crimson on this call. You really graduated into this early 2010s, I would call it like a tech boom post-recession, and ultimately you didn't write a book. You didn't become a geologist. You started writing at Fortune as a tech reporter. Tell us about that early career step.

Absolutely. So Harvard had a great program for undergrads. They still do called the IOP Director's Internship. And this was really clutch because especially back then, but consistently in my career, media has not had a lot of money. And so to break it in the industry at Harvard, you would work for the newspaper or one of the alt-weeklies or something, but they didn't have journalism classes. And then you really had to get that sort of internship. Thankfully through the IOP, I was able to get that internship at first WNYC in radio. I think they paid me like $10 a day, which was half spent on a MetroCard, so that was brutal. I was an SAT tutor to actually make ends meet and staying at home. And then at Fortune, I got to do my first reporting and I was so excited because they said no intern had ever written a print story for the magazine, but it wasn't against the rules. So it became my goal to write a print story, which I did. And then I was like, do I want to do politics or tech? They seem like the only growth areas and startups just really resonated with me. I wanted to cover the nascent tech scene in New York. I was not interested in going to DC and doing politics. So the rest is history.

But you can't leave us on that cliffhanger. What was the story as an intern that you got printed?

It was actually so funny because there was this big court case happening where a filmmaker had made a documentary about Chevron in the Amazon, and Chevron had sued him asking for his notes, saying that he was not a journalist protected by the First Amendment. I was way over my head. I had no idea what was going on with that. We had a very senior reporter who was actually writing about that. But as a sidebar, there was a group of newspapers and celebrities in media who were trying to support this filmmaker led by Robert Redford. So for my hustle, I got to call Robert Redford and ask what he thought about all this for like a sidebar one-page article that made my mom super proud because she loves Robert Redford.

That's an incredible first print article story. Every mom would be proud of their son writing about and talking to Robert Redford. So quite the pivot.

But it's been all downhill since. I've not spoken to Bob ever since, so she's still waiting.

Well, you've certainly interviewed some other household names, albeit in a very different industry. Let's fast forward a little bit to your career at Forbes. Over your decade at Forbes, you've had a front row seat to some of tech's most defining moments, interviewing leaders like Satya Nadella, Sam Altman, the Carlson brothers, Masayoshi Son. When you reflect on those conversations, which ones stand out most, either because of what they've revealed in the moment or how they've aged with time?

You know, all these interviews had very different experiences, like trying to follow Marc Benioff around the world was a hilarious challenge. He dared me to meet him in Japan, so Forbes flew me like middle seat economy, direct flight flight to Tokyo on one day's notice, and I was there for 48 hours. He ends up taking me to like a karaoke bar. I feel like he was just trying to mess with me, but it was a really interesting reporting experience. And that was a great story early in my career. Masa was interesting because it happened right before COVID lockdown, and he was even starting to hear from all of SoftBank's interests in Asia that everything was shutting down. So they weren't sure they even wanted to meet with me. And I think it was the day before Things started to really shut down in New York. So that just stands out to me as just a surreal interview. The world changed so much while I was working on that cover story. Going to cover Canva early on with Melanie Perkins is probably my favorite cover story I ever did. We got to write about Canva early and I had to fight to get that on the COVID Melanie was not a billionaire. The company was still not a huge, well-known business yet, but I just found her story really inspiring. And I got letters from young people, especially young women afterwards saying they wanted to be like Melanie. So I feel like that story made me really proud.

Well, I certainly was a reader of that story, and that was definitely a data point in just my career journey thinking about wanting to become a founder. So I think firsthand can really talk about how these stories do really shape the population's opinion on what they can do and accomplish, especially young women, early career. Hopefully we have Melanie on the podcast. That would be a fun full circle moment.

Yeah, I want Melanie on my podcast too, so we'll have to pass her off.

We'll call it a collect on that one.

Yeah. Yeah.

I think one thing that always gets Madison and me going is when a guest says, I actually have never told this story before, or I, I can't believe I'm saying this, but what have you learned about power, vision, or vulnerability even from being in the room with some of these industry giants?

For a lot of these folks, they are just so competitive that they always have to be winning something. I think that's the thing that's always blown my mind is they find out what a journalist makes for a living. I had a CEO offer me $1 million to quit my job on the spot and take over their website. I wasn't even sure if they were kidding and I'm like 90% sure they were serious, but it was just insane. But these folks, they live in a different reality in some ways than us, but at the same time, they are still relentlessly driven, competitive, insecure. And I think that was the biggest thing for me was once I profiled a few billionaires and spent time with these leaders, I realize that the game doesn't change that much in some ways. It's just like your connection to reality is different. Like Sam Altman still texts people like everyone else. It's just, he has probably hundreds of texts a day and some of them are about buying a new mansion or something. They're very different texts than me, but like, he's still just a dude. Right now he is a dad with a baby who probably spits up on him. So there you go.

We're all just humans trying to build cool things in this world.

Whatever level of success you reach, a lot of these most successful people, they just find another goal. It's almost like they can't help themselves. I've met very few people who just retired and went to a beach. Like, I'll tell you one story I haven't told before, which is I was working on a story about a startup studio that I ended up not publishing because the vibes were kind of weird. And the PR person for that unnamed studio quit halfway through the project. And I was like, huh, maybe it's because the vibes are weird. Turns out, no, it had nothing to do with that. They had made $50 million in Bitcoin and just retired in their 20s and were like, I am done. Mic drop. I haven't met a lot of people like that. I really respect that person to have that sort of comfort in themselves that they were just like, I'm out.

Yeah, it resonates for both Claudia and myself, that hedonic treadmill, if you will, that you get used to having these gold stars and then you kind of have to ask yourself, what's the next gold star? What am I even doing it for?

Yeah, and I think if the gold star can be good for the world, great. I'm psychotically working too hard on this brand because I'm passionate about it. Definitely not the easy route, but if the gold stars are ego-driven or something, obviously that can take us to not so great places.

Whenever I talk to founder friends that have maybe reached a milestone like exiting their company or raising another big round, it's always interesting to see what the next goal is. And it's such an interesting tie into their motivation around building the business. We've heard on this podcast funding should be for the ability for you to grow your business and achieve very tactical goals. And sometimes you talk to founders where it's like, great, let's raise like another $500 million. And it's like, why? Because we can. And so it's always interesting to see that bifurcation in how people think about why they're doing what they're doing.

You know, it's interesting there just to pause for a sec. One of the first lessons that I heard in my career was Stewart Butterfield, the founder of Slack, who was very good at his job, led Slack to obviously huge success. He actually was one of those people who said always raise if the money is cheap enough. But then I feel like what he didn't anticipate is how people took that so far during sort of the Zerfy times where we had founders taking over $100 million off the table. That I think is very different than what Stewart meant, but I'd be curious if he would still believe that today.

2021 was a very interesting time to report on funding, secondaries, all of that interesting stuff. Beyond general reporting, let's talk about lists. Forbes loves a list. You've pioneered coverage from the Forbes Midas List to the Cloud 100. Can you pull back the curtain on the why behind the lists and how they were critical to Forbes's overall coverage strategy of the technology and venture capital ecosystem?

The Midas List was started in 2000, and they have run it every year except one year where they took off for the 2008 financial crisis. When I took over, I think it was still a valuable brand, but we really wanted to expand it because we thought there wasn't a lot of transparency in the venture capital industry. And this was really relevant to founders to know which VCs actually have a track record, are actually out there in the market. Trying to take that brand to the next level was an early challenge for me that allowed me to meet so many great investors and also their best founders. My favorite part was that I got to talk to all these companies in the process of getting to know their investors. And I think that's one thing that's really valuable for Forbes with these franchises is the networks that they get. People like to make fun of the Under 30 list, but so many super successful people are 30 Under 30s. We just don't talk about them unless they get in trouble because success is not always the best meme. But I did meet through the Under 30 list, a lot of people who now run VC firms who are leaders of big companies. Sam Altman, for example, was the first callout of the first ever 30 Under 30 venture capitalist when he was still running Y Combinator. So I would have never met Sam early in my career if not for that list. And so I think the way it allows reporters insight into these industries and access, especially early in their careers to these people, that's the most valuable thing for me.

No, you're so right. The Forbes 30 Under 30 list has really become a lot more than just a list. It's a viral cultural and professional sort of moment for our generation. Speaking for Madison and myself, it was a major moment for us to be on the 2024 media list. While our output and work didn't change after getting that recognition, it really validated not only what we've been doing, but also put us in community with a lot of other interesting people. You were often the editor of the Venture Capital List. From your vantage point, how has the ecosystem around 30 Under 30 matured over the past few years? And what surprised you about the community it's become really?

There have been highs and lows where in the first few years, especially with the VC list, I felt like it was fish in a barrel because I was new to this. We didn't have any copycats from other outlets. Everyone was just an absolute killer. And a lot of those people are some of my favorite people still in VC today. Then I say there was a bit of a dip where VC got popular and maybe I was partly guilty in helping to popularize it with some of my stories, such as Life and people were maybe trying to join the list for the wrong reasons or even become VCs because they thought it was a glamorous job. And I think that was the less fun part where I would take comfort in profiling and promoting VCs who were not on the coast or they did not have big web presences. We of course had our like Gen Z VCs and stuff on the list, but I was always proud about those immigrants or those sort of diamond in the rough type VCs who had helped Amplify, and I felt that way about the founders on our list too. Nowadays, VC is just such a more mature industry that the last year I did it, I was looking at these people and I'm like, how have you done all this stuff? You know, in your 20s, you know, how did you start a podcast or write a book or launch a company or whatever and get everything done? It feels like the bar just raised. Same as if I were applying to college again, God knows what odds I would have had to get into Harvard today.

No, thank you for peeling back the layers there and humanizing it. When you mentioned almost your own access point to meeting some of these talented people who you yourself feel like you wouldn't have otherwise had access to, kind of sparked something for me. Like we met Alex York, who's become a friend of ours, and she moderated a panel we did this summer at our conference. And I hadn't been thinking about it. I assume you guys are in every room. On the outside looking in, reporters have all the access and people want to talk to you guys, but the flip is true too. It sounds like you guys are also trying to break in.

Totally. And now that I'm in my 30s, a lot of those last couple lists of under 30s that I worked with are helping me meet people from the next generation, founders 10 years younger than me, or investors who text very differently than I do and are way cooler than me. But thankfully, I can use the community to kind of meet those people, try not to embarrass myself, and refresh my network. Because my paranoia is that as I get older, all my network will get older too, and we'll lose touch with where things are really moving in tech.

You answered our LinkedIn DM, so I feel like you're doing really well.

LinkedIn is the future. Good to know.

Yeah.

And shout out to Alex too. She also answered our LinkedIn DM, so we're big fans of that platform. But let's talk about Upstarts. You're launching your own career journey and pivot for you in a number of years. So first of all, congratulations on taking the leap, Pho.

Thank you so much. It's been crazy.

I'm sure it has. So tell us a little bit more about the vision.

Yeah, so Upstarts Media was founded on the idea that startups are at their best when they challenge the status quo and punch above their weight. To try to achieve a lasting impact in the world. And it's an upstart mentality that I also feel like I share in the media industry. And so my goal is that anyone who's part of our community as a reader, as a listener coming to our events, can embrace something of an upstart mindset themselves. They don't have to be necessarily in startups yet, or they could be in, in a tech job or a law job, whatever, but they could be getting something from, I think, the best of what startups should be about. And I feel like so much attention right now, whether it's from social media or traditional press is focused on politics and big tech and only a couple players in AI. I like hanging out with early-stage companies too. I think the stories of founder journeys are really important. And so Upstarts really gives me the flexibility to go from inception through IPO, trying to share that sort of high-signal story that I think matters for this audience.

Incredible. It reminds me of the venture truism that emerging managers' first funds usually outperform on an absolute basis than a multi-stage manager, oftentimes because they're hungrier. You're ready to get out there, and it sounds like you yourself are excited to have that hunger and translate to getting to share the stories of those individuals who are on the journey too. You've described elsewhere Upstarts Media as being a multiplatform endeavor, and you hinted at that there, but everything from live video, the Substack, to perhaps a future plan for a podcast, which we love. What does a modern community-first media company look like in your eyes?

You have to embrace that meme, you can just do things. I think that being nimble, being experimental is absolutely critical because nobody really knows where audiences are going right now. We know that people are getting their news on Instagram Reels or TikTok. We know that they're not necessarily reading through a whole article. And even as I invest a lot in a newsletter, I'm mindful of the fact that some people are going to start aggregating newsletters via AI. So I really need to think, how am I reaching my audience as directly and organically as possible so that they are loyal and interested in what I have to say. Yes, you can aggregate me, but I hope that you want to feel part of my Upstarts community and be along for the ride with me, which is why being a founder myself is so fun. Because I'm learning a lot of this from first principles now, the hard way. How do I open a commercial bank account? How do I handle taxes? There's a million blocking and tackling questions that I'm going through as well. And I think that empathy and the fact that I'm doing it too is hopefully going to resonate with folks because I'm going to just have to try things and not everything's going to work. I've enjoyed doing live video initially. I hope to launch that podcast, but also things are going to go wrong. And I think that if I'm close to the community, my hope is that they will accept that things can be a little rough around the edges at first.

They absolutely can. If this podcast is an example of that, for sure. And if you need a bank, let us know. We're close with the Mercury team.

I know them well. But I still had to figure it out.

And that's so real, right? Like dogfooding your own product is such an important part of the experience. And maybe if we take a step back for a second more on the lens of where you're coming from and now where you're going, there is this growing tension of traditional media and the more decentralized creator-led platforms. I think officially you're a creator, we're gonna call you that. So why has legacy media been struggling to build this authentic connection with the startup community?

There are a couple ways to answer that. On one level, we've had this kind of moment of distrust between, I think, the tech community and traditional media. Partly this is a response to media getting a little over-positive and exuberant in the past, and then naturally things are cyclical. Folks were like, hey, maybe we should have been a little more mindful about WeWork as a $45 billion company, you know, and stuff like that. And I think people naturally got a little more critically minded, especially as some of these tech companies have gotten so powerful. We have a tech billionaire in the White House. And so the media, I think, is trying to do a job there and it's trying to answer an audience who are often not people plugged into the tech community. The average American might have very different views about what they want, you know, in tech coverage than the community itself. And so I think that's a challenge of traditional media is that their audience isn't always those insiders on X or LinkedIn, you know, is, is maybe our echo chamber. For me, I've always tried to write for an insider so that it's credible and empathetic and fair, but also with the accessibility that someone else might plausibly read the story. My mom reads my work. I don't want to bore her to death. My cousin who's early in his career reads me. He was just calling me earlier with some feedback. So I really want to get a wide audience reading Upstarts, and I think that'll hold me accountable. But it's just really hard, I think, at a big media company to make everyone happy there. We can move faster as creators and stay closer in an authentic way because we're building alongside them, if that makes sense.

It totally does. And also no mercy from the cousin. Oh my goodness. We're just figuring it out.

It was pretty good feedback, but you know, I, I'm asking for it.

I love the hustle.

That's like my little brother is giving me feedback on this for sure. And yeah, it's interesting, especially when working with our entrepreneurs in my last firm or just in general on the pod, people love the halo effect of a Forbes article. There's something really really powerful about that. And this tension with new media is that the credibility is something that takes time. How are you thinking about building a foundation with Upstarts that's going to build into a legacy that's as lasting as Forbes?

I also think a lot about how there's been these great media brands developing that are not necessarily journalistic, but they are journalism adjacent. You guys are obviously very good at interviewing, whether you would consider yourselves journalists, maybe not creators. Sure. And we've seen Tech Bros Podcast Network. We've seen a bunch of other podcasts be successful. I'm very mindful that a lot of great work is happening in those content creation areas. And so then I think, okay, how does traditional media and new media like me and these journalism adjacent creators, how do we all coexist? I think the TL;DR is that we will all find a niche. I think people will still want that Forbes article for certain audiences or milestones. I think they'll want to talk to Mario Gabriele or Tech Bros, or hopefully the two of you. In other moments. And then I think Upstarts will hopefully have some touchpoints that will feel really authentic too. And so my job now is to wave that flag about where Upstarts should be the fit, but I'm not gonna be the only solution. Awesome.

It's gonna be fun to see how the community reacts to it. I think already on the internet, we're seeing a really positive response for you, and we believe this too. There is a need for broader community engagement for early-stage builders and investors, and you're kind to attribute some of that to us. And we definitely have felt that in the last 5 years, that's been core to the podcast community and have even seen that URL to IRL experience where people are looking for this information online, but then they also expect to be able to find you on the streets. So that's been a part of why we've launched Inside Summit, which is our conference every year, started last year. We're doing it again this year, really focused on the under-35 founder landscape. So for you, as you're doing this multi-platform approach, how are you going to be thinking about events as a complement to media?

I'm going to try to start smaller. I don't want to compete with you or the Acquired Show or any of these amazing productions because I'm probably not as good at that. But I want to do boutique events close to the community. I have one cooking with the Stanford HAI Lab to talk about some results they have coming out to an AI founder small community. I'm trying to co-host things that feel that they resonate with my audience and also the Upstarts brand. And then I think we go from there. Maybe someday I have a bigger event, but I always think that I want to throw an event that you two or a founder would be excited to go to. And for me, my true north there is small, curated, high-touch. It's not ticketed and big, although that is of course where a lot of the money is for big media companies. There's a reason that events get so big.

So we'll see. We jokingly call our event Not Your Dad's Technology Conference, and I have license from my own dad to say that. And one of the things we've noticed actually, it's just a small little thing, is, you know, our generation likes craft coffee. We like a barista bar and I don't know, call it bougie, but if I go to an event and there's only drop pour coffee, I'm kind of like, guys, we couldn't have gotten a great barista up in here. And so there's just some generational differences too. We've had the chance to speak to other media founders like yourself, Jessica Lessin from The Information, Jane Metcalfe of Wired, and you're no stranger to venture as well as we've established. So are you seeking venture dollars to get this off the ground?

Great question. I spent a lot of time debating this and I met with folks about possibly taking investment. Ultimately, I decided for me, I would be taking money for the wrong reasons. I'd be basically doing it to feel more legit and be able to pay myself a salary so that I didn't feel stress. But actually, maybe the stress is healthy in a way because I need this business to really resonate with the audience. So I decided to bootstrap and really push for product market fit, resonate with that audience, be subscriber-driven, and then also partner-driven. So I'm lucky to have Brex as a launch partner. I'm going to work with other companies that I think meet my Upstarts audience. And then I'm really grateful for the support I've gotten from those paid subscribers so far. They're going to be voting with their dollars, and I think that'll be healthy and terrifying for me. So ultimately, I was so tempted to raise money and try to do a bunch more stuff, but I decided, nope, let's see what works. And then maybe I can scale once I figure out what's really resonating with the community. The VCs are like, You're not raising money? What? Are you trying to do a lifestyle business? I'm like, no, I'm just trying to figure out what actually works. But I think VCs think, you know, to the hammer, everything's a nail, right?

The dirtiest word in Silicon Valley is lifestyle business, I've come to realize.

Oh yeah. When I heard that, it was devastating to me, Claudia. Uh, okay.

We're not doing this for the gold star though. We're doing this to change the world. So this is okay. We're okay with this reality.

I also wanna have fun though. I think being a founder is a lot of work. I was grinding till late in the morning or early in the morning, I should say, when the night in the morning. Become the same thing. I was doing that a lot this week and I expect I'll be working really hard. I wanna make no illusions that being a founder is easy and all sunshine, but I do think that controlling my own destiny and being able to build in public and ship all this stuff with the audience is fun to me. And so as much as it's a lot of work, I feel so energized to be doing that. I'm sure you both have felt that as you've built out this brand as well. It's super special.

We're co-owners of this business and A, doing it together is amazing. And then B, getting to be like, yeah, that was us. That's pretty sick.

The room is now a house or something like that. Okay.

Okay. I love that. Coming to you season 13. I was at Altimeter's investment day in October, and I think Brad Gerstner might've said the end of the blue link era is now, like 16 times. He was just death to the blue links. And I think what he meant by that was Google is shifting under our feet. Search paradigm is shifting. Of course, that's going to impact media and readership and loyalty. There is no right answer, and I don't even know how to ask the question, but if we believe that blue links are dead, how do you think building an audience for the future is going to shift with AI?

We talked a little bit about traditional media, and I think that this is a huge challenge for big online organizations, not just in media. And I think the challenge there is that everyone built for Google and they built for SEO and they built for sort of an online advertising network that is getting undermined a lot by AI. I think the future of Perplexity and a Google search that is a lot like Perplexity is coming. And so what that means for all these business models is a lot of pain. I think what it does is it pushes what I'm trying to get ahead of here with Upstarts, which is that close relationship with an audience where if you don't need to Google any article, why are you reading something? How are you finding my work? And so that's why good sense of taste is going to be so important because I think that AI otherwise kind of disintermediates all of us.

Something we're thinking about is how to create more generative search experiences and long-form content. So we can talk more about this, but we're working on a project internally with some friends to allow for you to search really contextually specific questions. On the body of our podcast and then generate that in a timestamp-first way such that if you only really care about your fundraising journey, you're gonna listen to 5 minutes of this podcast and not the rest. And in the future, we think that's gonna be okay because you could listen to the same 5-minute clip from 10 episodes cuz all you wanna hear is about fundraising. And we think in the future there's gonna be more opportunities for that, which we're excited about.

I love that idea for exposure to new audiences. But I think my gut feeling is that you need— do you guys have a name for your fans? Is it roomies or something like that? Or—

I think you just made that happen. Okay.

So you have your roomies and I'm gonna have my upstarts and those people need to feel a relationship with us. I heard from a very successful podcaster once, as I was thinking about doing all this stuff, that they had reached a point with their audience that they don't really see a noticeable difference in listenership when they have a huge name on versus is a kind of less known person because their listeners just have a relationship with them. They trust them to, to spend their commute with. And so I think, you know, if I do a podcast about nuclear energy, I would love that to pop up in research about new startups in nuclear. But at the same time, I would not like a future where no one listens to this whole podcast and someone is just getting one excerpt from it, because that's no fun. We're having fun. They should join us and have fun with us.

Access to information becomes more and more commoditized. What is that next? Personality layer that folks are actually leaning into. I think even for us, season 1 and 2, like our podcast cover art was an image. We weren't on it. We were posting from The Room podcast channels, and then we were like, we should be posting from our own channels and we should put our faces on there because ultimately we want folks to not only hear the wisdom of our guests, but also just our contextual experience as we go along for the ride with our guest. So. That makes complete sense.

I was talking to an investor this week about how they consume newsletters, and they had built a tool that just sent a digest to themselves of all the 10 newsletters they subscribed to with sort of one takeaway from each one each day as their way to speed read all these newsletters. And I was like, wow, that sounds so efficient. Do you enjoy it? Do you like reading that thing? And they were like, no, I hate it. It feels like taking medicine. And I was like, Well, there you go. Like, you've won, but at what cost? That's a great question.

Just to get into the nitty-gritty of your founder journey, would you consider Upstarts Media an AI-native company? And in what ways are you using AI in your workflow from editorial decisions to distribution?

You know, I think it depends how we define AI-native. I would say I'm using AI tools from day one. My first article was about Granola AI because its note-taking app was the first one I didn't hate. And creating a little smart template for audience feedback calls was actually really fun for me. I almost had so much fun pulling the insights that I had to remind myself, no, you have to do something with all this info. Cause it felt like I was just like in collection mode. That was the archaeologist deep down inside me, but I use Granola for that. I use AI to transcribe calls. I'm going to be using all those tools for my tagline of Upstarts, which is startup news starts here. My wife and I plugged that into ChatGPT and all these different iterations to see if there was a better one. We ended up thinking, actually, we love Startup News Starts Here, but we looked at probably 50 AI-generated alternatives to double-check. So, I'm going to be playing with all these tools myself, but I am not like an AI company because at the end of the day, my work is the product, and if AI could do my work perfectly, no one would pay to subscribe. They'd be like, I can do this myself.

A unique point of view, personal brand. We haven't abstracted that away yet, nor do I think should be.

Right. There are podcasts that are all fake people. They're like AI avatars, but it's a novelty that people listen to for 20 minutes, but they're not subscribing right now because it's not fun. There's nothing interesting in it. It's just sort of what a model thought you might want to hear.

We chatted a bit about your career at Forbes. We've chatted about kind of upstarts, where we're at today as we look to the rest of 2025, 2026. What's next for Upstarts and for you personally?

Upstarts is going to hit the West Coast later in the spring, speaking at a couple conferences and doing things like small events. So if folks are curious to team up, they can email my partnerships@upstarts account, or they can just ping me on Twitter or whatever and try to get involved. So I'll be out there meeting with the ecosystem. I'm really hopeful to have excuses to go to other places too, like Austin, Boston, even London. I really love London. So trying to find ways to get Upstarts on the road. And then I think another stretch goal for me would be to experiment with short-form native video. So one of my good friends is the amazing tech comedian Alexis Gay, who you should definitely have on someday. And her videos are so funny, so topical. So I plan to annoy the heck out of her learning how to try to do that as well, just to try to have fun and reach an audience in a different way.

I think Madison and I are like Instagram Reels. Chat is littered with Alexis's videos. They resonate, they hit home. Also, good luck on your journey on short-form content.

Claudia and I found that the hardest thing to do.

Oh, I'm gonna be horrible. But the thing is, I have to try, right? Because if a lot of people are getting their news from Instagram Reels, I need to at least attempt to be there. I can't just be like, oh, I have a good Twitter following, so I'm just gonna stay there forever. Like, that would not be very smart.

Okay, hot take topical question. Who do you think's gonna take Twitter or TikTok on?

Do you have an opinion? Who's going to buy TikTok? Yeah. I still feel like it's going to end up being a really boring company like Oracle because they have the political connections with the White House and they won't put their own brand onto it. So I think that Larry Ellison is still my bet, as unexciting as that would be. But it would be interesting if one of these LA groups or one of these sort of dark horse candidates won. A lot of them have no chance. I will eat my figurative hat. If Perplexity or AppLovin or one of these companies actually buys it. I've been so tempted to start tweeting every time I see one of these, like, I'm still trying to buy TikTok because sure, anyone can say they're trying to buy TikTok. What do you think, Madison? Who's buying TikTok?

Well, actually the Perplexity founders were in my class this week talking about why they would've bid in for TikTok, and I actually really liked what they had to say. It made me think more like them or Amazon would perhaps be the winner versus Oracle, which really doesn't have an effective direct-to-consumer angle or strategy at all other than The Sun and their production company with Paramount. So that to me is where that one breaks down.

I just feel like some, a company like Oracle would basically just leave it. They would just be doing the data side and then they would leave it to be independent and nothing would really change, which I think is what a lot of users would want. And as long as VCs and everyone made money, I think a lot of people would be pretty happy with as minimal change as possible. I think Aravind is a genius here because if Perplexity is out there making their case, I don't think they have the money to do it, but if they at least sound incredible about it, it makes him look smart. It makes Perplexity seem big and savvy. So like there's zero downside for him to, to be beating that horn.

And one other thing I'll add is it just sparked my memory of the YouTube acquisition for Google, right? Like arguably Alphabet would be in such a different position if they did not take YouTube off the market in what, 2003, 2004? 2004, maybe 2006, but just right around then you might remember. And I think that really changed the trajectory of Google as a content company. And so I could see it not being crazy if the right backers are with Perplexity on this, but who's to say?

We need to like have a link to like a poll. Are you with Alex? Are you with Madison McIlwain?

I think the other interesting what if is if someone buys TikTok and messes it up, why hasn't X relaunched Vine? Why aren't we running that back or trying other things. The idea that everyone's just given up that TikTok is the end-all be-all is I think shortsighted because who knows if TikTok's algorithm, all the magic was in China and suddenly everyone hates the feed and then it's like, why don't we have another tool here? Elon, if you're listening to the room, you gotta bring back Vine.

Shifting gears as we come up on time today, Alex, we're gonna ask you our hero question for the podcast. We ask, who is a woman in your life that has had a profound impact on you and your career?

Most of my editors have been women, and the first editors who ever took chances on me at Fortune were Lee Gallagher and Jen Rheingold, and they put up with me as a really annoying college kid and gave me that rope to figure things out. I think one of my first series was Your Next Job, where I talked to people to like make up jobs that could exist in the future, and let's never fact-check what those were because they were certainly all wrong. But they were huge in my career and most of my editors since have also been women who were really helpful to me. Then I think there's those leaders like Melanie, who we talked about, who continues to just prove me right that she is doing so much. Just for people who don't know, she's obviously worth many billions of dollars now with Canva's valuation in the tens of billions, but she's pledged 99% of that to her foundation. And if you ask her, like, she wants Canva to be a trillion-dollar company. So that she can have bigger impacts helping the world. She has no interest in being rich and retiring to the beach. I think her husband proposed to her with a $17 engagement ring. Melanie, I think, is doing it for all the right reasons. And when I write about someone like that and they keep it up, that gives me a lot of energy as well.

We'll tag Melanie when we release this episode.

Nice. Definitely tag her as Melanie Canva though, because one time I tagged a Melanie Perkins and it was a random person and I felt really dumb.

Alex, thank you so much for your time today. Thank you for joining us on the podcast, sharing your story. We're so excited to see what goes on with Upstarts and can't wait to collaborate in the future.

Awesome. I can't wait to have my podcast live so I can reciprocate and have you on and give you all the interview treatment sometime soon.

Thank you so much for joining us at The Room Podcast. If you want more from The Room every week, Subscribe to our newsletter at theroompodcast.com/newsletter.

We'll be back next week with a new episode, an inspirational guest, Tuesday, 10:00 AM Eastern, 7:00 AM Pacific. See you in the room.

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