Why He Left a Decade at Forbes to Build Upstarts From Scratch - Alex Konrad - Upstarts - EP#116

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 Conrad 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 Conrad 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 COVID stories on people like Mark Benioff, Frank Slootman, 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 Conrad, welcome to Not Another CEO Podcast.

Wow, thank you so much. I'm pumped now.

Okay, first question out of the gate, a little different than I ask 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 ad tech. So for a minute there, I was all about the New York ad tech 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, the Wiz CEO, like some of these folks who are about to go public or about to get acquired, you know, but, 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 5 each day because it's probably more than 20 a day.

Wow.

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, 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, so to do more than 2 articles a week really strains the care and the effort I want to put into something.

And one of the things I notice, you 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 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.

Whatever, you know?

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 gonna 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, I— part of my brain is like, I should be covering every startup piece of news that matters in the world.

Hmm.

I can't possibly do that. And so I have to kind of tell my brain to pump the brakes sometimes.

We were talking before, like media, media has changed a lot. I mean, when I started working in tech, it was TechCrunch was kind of the, 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, and to be honest, nothing against TechCrunch, but I haven't read TechCrunch in, in years. I mean, I literally have not visited the website in, in years. And, and I feel like it's just changed a lot. There were so many outlets for a long time. time covering tech. I mean, in the peak for me in that 2010, 2015, kind of that window of time, I mean, there was so many people were covering it and it feels like it's gotten less and less and like just 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, what are you seeing?

Yeah, there's, 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 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 opened that one. So, so there is a challenge of just getting in front of people with things. that 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, 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. Well, some people obviously did, or they wouldn't write an operation, right? So I think that's one thing is there's just this— 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.

Right.

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, 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, like, where are you? But, but, but you have to understand, for whatever reason, they just haven't engaged with my work. They didn't see my LinkedIn posts or whatever. And so I now I have an opportunity to re-explain who I am.

Right.

But, but you're like, wait, like, 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, and 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. This is my— 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— yeah, I was actually— I was talking to people here at the podcast studio before we came in and I was talking about— we were talking about the algorithm and playing to the algorithm. And that for me is one of the things I've been— 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 journalistic, 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, that fast-moving kind of algorithm. And that's, 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, with the right— it only doesn't get 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, they do draw in a lot of people.

Right.

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.

Yeah.

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. Do you—

what did you feel was, was, was the move to start? Because it's a big thing to start your own media company. Any company. Was that move because of who you wanted to cover? Was that move how you want— like, what was— why did you do that? Why did you leave Forbes?

I'm a very intentional person to a fault. You know, I'd say my wife is the fast-moving, join the new startup, you know, bounce around the industry, 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 3 steps down.

Yeah.

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 would be, 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 roleplaying 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 fault. You know, I'm like, oh, if I had made that decision 6 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, not obsess about the sort of past decisions. I think why I bring this up is because I was tempted to leave Forbes many times over the years.

I'm sure.

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 lose that wider platform and accessibility of the work because so much of our work was also not under a a huge paywall. At some point, though, 15 cover stories in, we don't have a podcast studio, 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. And I'm sure this is true in other, 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.

Right.

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 Altman 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 Right, right.

What are you looking— like, when you're actually talking to a founder and you're gonna cover them and they're— no one's covered them before, 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, I'm always like, okay, back then in BetterCloud, I'm like, I gotta sell this guy. I gotta, like, you know, like, how do you— 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 3-minute, whatever it takes to read the article, let's say 3 or 5-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 3 to 5 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.

Mm-hmm.

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. Not saying you specifically, but any founder in their, in their personal writing or in an article. Every sentence has to count, has to build on the previous. 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, 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, 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, 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. Hmm. 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, or I want the lifestyle. You know, I wanted to go to YC. I wanted to be anointed a leader. I just feel like those people are the ones who overraise when they can, overhire when they can, get into Twitter fights when they should be, you know, focusing on their, their business. And I think they burn out faster. Yeah.

I, I've asked a couple of people this question. 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 needing to have that obsession. Something's 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?

Yes.

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, 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.

Right. And it's just completely different. So I think we have seen cycles there. You know, there have been also moments where, you know, a bubble bursts, like, you know, the ZIRP era, and suddenly, you know, it's harder to raise, and people are like, this isn't fun anymore.

Yeah, exactly.

So I definitely think it can, you know, it's not great to just be doing this because you see everyone else doing it. 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—

No.

He's a very Dutch CEO. He kind of can be a little bit of an asshole, 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— I 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? But, you know, his advice, like, I think the best advice he ever gave that I heard was he always wanted to be close to the engine room of the business. So whatever is really making money and driving the business forward or, you know, creating the product, he wanted to be as close to that as possible. That's great advice.

Mm-hmm.

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, the CEO of 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, right, right. I think, 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, right? 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, arms rolled— sorry, I'm sorry.

Arms length.

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, I'm better at sales than I thought I was, but I'm still— my 10x engineer equivalent is storytelling.

Mm-hmm.

I really think that I can just tell a better story faster, deeper than the average person. And even if, 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, 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 really freaking good.

I agree with that. I agree with that. Like you said, especially in the early days, something that separates them. I actually didn't— when I was early days of Better Call, 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— except my wife says I'm like Chris Farley from the, you know, living in a van down by the river. Yeah, she's like, you get so amped up and you get the people going, you know, you get the people going and through the tough times and through the this and, and making people believe that we're gonna get there. And, and so I, I didn't appreciate that. And I'm like, I'm actually not great at any other. I mean, I'm, I'm good at some stuff, but like that actually is, is, is the superpower.

And that's fascinating because You know, candidly, I worry how good I'll be at that because I am so much the equivalent of the 10x engineer in my niche, right, that often that meant I was the most senior, you know, IC. I was the almost lone wolf rainmaker. And does the lone wolf rainmaker always become a great manager of people? No.

No.

Yeah, I've had a mixed record as a manager myself. And so I think as we think about scaling Upstarts, as I aspire to have writers, employees working with me, that'll be something that I'll probably ask someone like you for advice on.

Yeah.

Because I don't, you know, things I worry about is, you know, it's not good when a founder is too negative to employees because they're not just immediately getting everything the way that it makes sense in the founder's brain, or if the founder lives and dies by their company, Yes, you want employees who work crazy, crazy hard, but it's a little different when it's not their business. So I certainly wouldn't want a scenario where Alex, the Upstarts CEO, is ragging on people for not being living and breathing Upstarts quite the same way I do. You know what I mean?

100%. It's actually of all the CEOs that all the founders specifically that I advise, the number one thing that I hear them all say to me in frustration is. Why does nobody care as much as I care?

Yeah.

In almost every conversation, how could they not? Do they not see that we need to do— and I'm like, they're not the founder. Like, even the ones who care the— I mean, I've had people who care the most, like, almost like they're the founder. They're still not the founder.

Right. And I've seen this as well, talking to hundreds, thousands of founders over the years. I think the best thing you can do is find that career development, or that product, or that opportunity that they become obsessed with. And it's like their own little quest that feeds into your bigger quest, right? But to just be like, your mission is that our company is successful, it's too big, right?

Exactly.

Yes.

Exactly. Actually, that's where I think my motivation, my superpower there, was being able to key into what is that thing, and then knowing in the back, even if I have 100 employees, at least my best ones, knowing what is that thing that's driving them so that I can put that in front of them.

And steer things.

And steer them kind of there. Yeah.

That's amazing. So I aspire to be good at that someday.

Yeah. Let's go to the investor side, because you did the Midas List for a long time.

I did, yeah.

Can you just explain for people who don't know, what is the Midas List? I'm pretty sure most people don't know.

Yeah, I'm so sorry for anyone who has to learn about this. The Midas List is the definitive— global ranking of the world's top venture capitalists. It's something Forbes has done since 2000.

Oh, since 2000?

Yeah, it's been around for a long time. I took it over in 2014 and I ran it and expanded it and hopefully improved it for a decade, which was, I think, one of the longest runs anyone has had. It continues to be, I think, a data-driven, really earnestly trying to be as sort of impartial ranking of venture performance by partner at these firms.

So, and what, what now, having done that for over a decade, what do you think makes the best investor?

Yeah, I've gotten this question a lot, and the answer can change a little bit based on my mood. You know, am I feeling the quantitative side? Am I feeling the more passionate side? I think that, first off, similar to our founder who's obsessive, the number one thing that I hear from the leading tech CEOs who have worked with investors is they want an investor who does feel like they're part of the team, who they can call in crisis, who is going to be calmer than them when things are going bad and more excited than them when things are going well. And I think that at the end of the day, the number one thing I hear, and this is whether it's Sequoia, Andreessen Horowitz, the very biggest firms in the world, when you ask people who's your favorite partner at these firms, it is often the person who picks up the phone, who might be a billionaire, but still, you know, flies somewhere random to help close a deal or a candidate.

Mm-hmm.

It is just that hustle. I think when an investor is acting more like they're an oracle that you should be grateful to be sort of getting little nuggets of info or help from, There's only a very small number of people whose names rhyme with Kinshasa or something who can maybe pull that off. Yeah.

Yeah, that's— I'm thinking about, as you're saying, and I'm laughing because I'm thinking about the investors that I've had over the years. And I've had people who— I had one who I didn't take as our investor who said to me, Dave, you remember every morning when you wake up, And then he said his name, that I say to do— that's literally what he said to me, that you, David, remember what I tell you to, like the oracle. And I was like, this is— is he serious? I don't know. Like, am I— he was dead serious, you know? And versus one of our investors I was talking about, Enrique Salem from Bain, and he would do our calls, our status calls, like 6:00 AM Pacific time on Fridays, you know?

Mm-hmm.

And he never missed it. You know, if a board meeting, he'd like fly in from wherever for the day and then fly out the same day. And, you know, and just was hustling, I would say, and sometimes more than me. You know, I was like, this guy's hustling, you know?

But I do think the hustle can reflect in different ways. Like, one thing that I always kind of laugh or push back on is there is a bit of a culture of like performative hustle. So I wrote a cover story with, with another reporter, George Anders, very early in my career for Forbes on Sequoia.

Mm-hmm.

And I went really deep on Sequoia. And, you know, there was Doug Leone was there. And this, this is kind of refiltered in years since. But, you know, Doug Leone is the kind of guy— and he used to run the firm— where you'd show up at 4 a.m. at the office hoping you were the first one there and like, he's already there. Or it's like, oh, I went swimming, I worked out at 4:30. You know, what were you doing? And I've, I've taken phone calls after midnight from him about stories. And I do think that, like, that stuff, if it, if it fits his brand, if it helps him, is great. I don't think you need to swim at 4:30 in the morning to be a great VC. I don't think that you need to be the very first one in the office to, like, a ludicrous degree.

Yeah.

If I'm showing up at 3 a.m. at the office and I'm asleep by noon, I don't really see how that helps anybody.

Yeah.

But, but Doug is more of like a sales type. investor, and his advice is very market sales driven. So I think that's what you want from him. But you could be a great sort of product helping or strategy helping VC where you want something very different. So I think like in every firm, you know, look at Sequoia, you have the Doug Leone type and then you have Alfred Lin, who has been number one on the Midas List a few times, who has his own like legendary portfolio. And I at least don't see him bragging about the 4 a.m. swimming. I think he's more likely to be doing the tequila shot or, you know, having a good time living his life. But he's still arguably as good an investor.

So how much luck do you think has to—

like, all of business has luck, right? I mean, like upstarts, I— the most I can do is get a lot of shots on the goal and hope that some work out. But sometimes my my favorite articles, the ones I am really proud of, don't hit, and ones that I spent less time on really hit.

Mm-hmm.

So, I mean, every day I see that there are some things I can't control. I think this is especially true in VC as well, where sometimes you back a founder because you love them and they pivot into something huge like a Slack. Sometimes you back an amazing founder and they don't pivot or it doesn't work out. And they were arguably as good as Stewart Butterfield in some ways, but they just didn't find the next Slack. I think we can see some patterns, but we can't overindex on, you know, just those results. So the Midas List, for example, is, I think, a really valuable tool to see who has a consistent, really impressive portfolio. But I don't think anyone would say the Midas List is the definitive only metric. for success. Like, I think it's the best ranking out there, but rankings are limited in their value.

Right.

And I'll give you an example. You know, take Airbnb. The investor at Sequoia who wrote the check to Airbnb is not the one who took the board seat and spent years helping Brian Chesky build a generational company that went public. Was it the guy who wrote the check? who wasn't there who is the genius, or is it the one who was on the board who really helped, or is it some combination of the two? This stuff gets a little kind of gray, a little convoluted, and so I try not to be overly kind of prescriptive about what makes great. Yeah, yeah.

I think, I think that for the, for the business, for the business of venture, where the returns— the only really deals that The deals that matter are only the ones that are the 100x returners. I mean, really, at the end of the day, that's what matters. And that, to me, luck is such a big part. But to your point, I think a lot of times the founder, the investor, they, they maybe make their luck, you know, like in some ways, or they put themselves at least in the position to be lucky, you know, to do that pivot that then hits.

Which is hard because in this environment, I think if you're a founder or an investor, there is a lot of incentive to almost go overly big or go home. Because if, to your point, the goal is that 100x return, if someone who YOLO'd their way into a 3-level-down, you know, SPV for Anthropic shares at whatever, like a $60 billion valuation, and now they're up over 10x and they're like, I'm a genius, If that person's making a ton of money, should you just go do the same thing? Or like, why am I even writing a $3 million check to a small startup at that point? That can be one sort of incentive. And then on the founder side, you might feel pressure like, why am I trying to build a software SaaS business when the AI labs are just going to eat me? Or—

Literally, I think that's exactly what it sounds like.

Right. And I will say, as upstarts, as the founder and as just someone who kind of— this is— these are my people. I really resonate and respect the people who don't get obsessed with just biggest number possible and are like, I'm going to build a valuable product that people love that will help them. And success for me could be a $5 billion company or even a smaller company that had impacts versus my only metric of success is I could build something as big as OpenAI and Anthropic.

Right.

Because plenty of VCs right now, if you look at their checks, They are writing insanely big seed, A, early-stage, you know, checks into companies, often without a product, because they're like, this person's track record or the area they're in has a higher percentage chance of reaching a trillion-dollar company. And that's all I care about.

Yeah, I think the way you're saying it is so— I've been feeling this so much recently because I have these— I meet a founder, let's say, Have a product, couple customers, but they're early and they're going out to raise a seed. And they go to some investors I introduced them to, and the investor's like, Dave, they're not really thinking big enough. I'm like, I'm pretty sure they're gonna get to like $50 million in 2 years. Like, not big enough. You know, Harvey did that in 1 year. And I'm like, okay, but like, let's put it all in. But but to this, the problem is they're motivated and incentivized. the investors to look for the people who come to the table with these huge visions. And you end up with a lot of— I'm not saying they're all like this, but you end up with a lot of the Adam Neumanns and Elizabeth Holmes because you have to tell a story. You literally have to. If you're an operator CEO, like you're in the weeds, you know how to build the business, you can't fundraise.

Yeah.

Because you have to go tell a huge story to get that check.

Yeah.

And then you have the people who are great at storytelling But on the flip side, can't operate.

Storytelling is a weapon. I guess this might be good for me. I think storytelling should accelerate your story for good and bad. It shouldn't be the entire story. And so if you're a great salesperson selling magic beans, it should catch up to you eventually, which we've seen with some of these flameouts. But I think what's interesting is Would you rather have 10 founders who are amazing hype people and have a, let's say, 1% or less chance of reaching a trillion-dollar business, but it's all or nothing? Or would you rather have 10 founders who are solid, running between the lines, higher percent chance, I don't know, 5% chance of building a $1 billion business, But none of them are going to be a trillion-dollar company. I think—

I will always take— me, always the latter.

Well, I think the firms with huge assets under management, AUM, for people like, like to get that 10x on a multibillion-dollar fund, they might say, you know what, I'd rather take the 10 crazy trillion-or-nothing folks. And so I think founders need to be really mindful of that when they think about who they're partnering with and also be very honest with themselves about which camp they're being put in.

I agree with that. It's interesting because I look at it and I say, I think the latter there's actually a way to do that and invest in 10 people who have the obsession, who love the game, who are operators, and that are going to get to maybe not $1 billion, but hundreds of millions each and, and can build really real companies. And I think you can get that ratio to like 20%.

Yeah.

You know, in terms of hit rate, but none of them are going to be most likely a trillion.

I'd be, you know, I don't invest at Upstarts. I'm like purely journalistic, you know, and if if that ever changed, we would have a lot of scale, and I'd really communicate it to people clearly. But I think it's important to have clear delineation there right now.

Yeah.

So this is all a hypothetical, but if I were investing, I do think that I subscribe more to the idea of great founders can find the great market, because there is this sort of cliché in Silicon Valley that a good founder or great founder even can't make up for a bad market. They can't just create something out of nothing. I think, though, when you see how many companies pivot these days in this AI era, when you see founders just show great resolve, creativity, I think that great founder will find the great market. So if you back the great founder, even if the market seems too small or not great, they will realize that, they will evolve, or they'll prove everyone wrong and Show the market was bigger than people thought. So when I hear, oh, this company, its TAM, its total addressable market, is too small to be compelling, I actually kind of reject that.

You, for you building upstarts, I'm curious, like how's your founder journey been?

Yeah. So in a way, we feel like a normal startup. In a way, I feel like sometimes I'm just that. creator trying to get views on Instagram. And then sometimes I feel like a good old-fashioned small business because I am bootstrapped. And so having seen the cycles of layoffs and sort of growth doom loops that media companies get into, it was important for me to Upstart to be really sustainable from day one.

So you decided like—

I was like, I met with folks, I thought about raising money, and I opted out of doing it. And so I'm only growing the business profitably from revenue. And there are tradeoffs for that. You know, on the one hand, we control our destiny. I can do a lot of things. I feel very stable. On the other hand, there is the question of like, should I be going for that trillion-dollar equivalent? Should I be going more, you know, throw a lot of things at the wall? And so I think that that is a tradeoff that I grapple with. The other thing that I think you just don't realize until you're a founder is how precious a commodity time is. And focus, and so this is something I still am candidly learning after more than a year. Is how do I keep forcing myself doing some sort of failsafe, like escape hatch? Like hey, you just went down a rabbit hole or started talking to a person or got caught up on something that is not the most important thing you should be doing. It's not the highest impact thing. Like like that course correction is something that I'm still working on because I can be the kind of person who goes really deep down a rabbit hole. And then I'm like, why did I spend a day thinking about retention flows when this is a small percentage of my business and this is not the most important thing I should be dealing with right now? You know?

Yeah. How is the personal part of it? I mean, I know your wife is in startups herself.

Yeah. Yeah. Very different. You know, my wife works at Clay. She's 5 days a week in an office with a fast-growing team. And I see kind of that startup version. I'm much more the closer to a garage. For me, it's just like a home office and then taking meetings around New York. But I'm very much a solo, solo founder there. And I think it can be lonely. I think I try to check in with other friends who have startups, but they— we all have very different kinds of startups. And so this is something that I also learned is that everyone's baby is so different. that there are some things we can commiserate about, but like, there isn't anyone doing quite the same company as me, right? There's even great media people, but their media business is different. And so I'm sure this was the case for you too. There are some things that just— I don't really have anyone to fully appreciate or talk about it with.

Yeah.

And so I've, I've joined a lot of chat groups with, with founders, some who live in Brooklyn near me, some are, you know, independent media people. to try to like pool best practices. Or one of those group chats is actually literally called like New Media Therapy, and it's for us to just vent and talk about that, you know, like because we'll have crazy silly things derail my day. Like someone maybe doesn't love the newsletter or they didn't intend to keep signed up and they were too lazy to unsubscribe. So they hit me with like multiple chargebacks for like small amounts of money. But that's so annoying. I'm paying fees. Chase, if I accept it, is going to ding my business like this lazy chargeback on their end, which maybe maybe even an AI agent is doing automatically, like maybe they're not even doing it at all. It's actually like really annoying to me. And while the money is small and obviously not gonna affect my business too much, it can like really get under your skin, you know, like when a customer is just crazy. And so to have someone to like vent about that with, then other people are like, oh yeah, I've had that happen too. You know, I don't know if you ever had like a crazy customer, but—

Oh my God.

That one person can bother me more than the 5 people telling me, good job, buddy.

I have stories of customers. I mean, I had a customer at Vocalocity, the first company in Atlanta, who one of our support people— this is great. I don't think I've ever told this story. One of our support people posted an email exchange with this customer because the customer was cursing at them and all this stuff. And they posted— 20— 2006. Yeah, posted on a forum, and it was the whole exchange, and deleted his email from everywhere except for the very end of the email.

Oh no.

So on the forum, this guy Googled his name, the customer. Yeah, and pulled up the forum with this thread, and it's all these people bashing this guy.

Oh my gosh.

And he calls me, he's like, I'm gonna sue you. And I'm like, for what? You know? And then he sends me this thread and I was like, oh God, this isn't good. So I go to the Sporker. I'm like, dude, you got to take this down. He's like, I, I was taking it down, but he started to attack the forum owners. He started to send legal letters. And this is like this underbelly of like this group of people was not people you wanted to mess with. They started creating websites about the guy, like, oh my God, like dozens of websites.

Yeah, I can't—

it like kept going and going and going. And it was the craziest thing. And this guy literally showed up to the office to beat up the— he like came to our office physically. We had to like keep the door closed, call the police. It was the craziest thing. But like that kind of thing, I mean, I've dealt with— that was the worst. And he was threatening people to— anyway, it was crazy. And then I said to him, listen, you know what? We're going to cancel your service and I will refund you for the 3 years that you've been a customer. That's what I said. I'll refund you 3 years. I'm so sorry. He's like, no, I like the phone service.

So for me, I do. If, if, if someone does complain or if they do something like that, I always just want more data as a founder. You know, like, I want to have a product. My product is my storytelling, whether it's the pod or the newsletter. But I want to know how I can be doing a better job. And I will say one thing that has been interesting in my journey so far is often when I respond to this supposedly angry person, Hey, I get it. I'm happy to offer you a refund. How can I do a better job for you? I never hear back. And I'm like, are they embarrassed? Are they like, this guy's getting more work from me? Like, they thought I was a faceless person, and now here I am being like, excuse me, here's your money, but like, why do you hate me?

Right.

They're just like, oh crap, that's a real person. So who knows? But it is funny because like, obviously when the business is going well, you don't wanna spend too much time on that stuff. But I am a bit of an obsessive person. Like, you know, I am paranoid. How can I be doing a better job?

Of course, of course. And it's your— you are the brand. I mean, the two things are—

It is very personal.

—connected.

Yeah. Yeah. Although not as personal as someone showing up and—

Legit, it was— I could talk about that one story for— it was crazy.

Well, I have been working— I won't say for their privacy what story, but I was working on a cover story once for Forbes, and I was at their office. And this crazy similar thing happened where people come up to the CEO, and they're like, we have a situation. There's a man with a backpack who has, like, talked their way into our office, said they had an appointment with someone they didn't, and they, like, are asking people where you are. Like, they're looking for you, the CEO.

And you were in the office?

I'm sitting with the CEO when they hear this, and they were like, oh my gosh. Like, they'd never dealt with the situation before. So we had to basically hide, the CEO and me, because they didn't know. And then finally security showed up and checked to make sure this guy didn't have like a bomb or something.

Right, right.

It turned out he had just like weird pamphlets in his backpack and he wanted to like yell at the CEO about something. He wasn't trying to commit violence, but you never know. And we left to go to an event together. I'm shadowing the CEO. And as we leave, we see the guy standing with police like on the corner. And I see the guy recognize the CEO. And I'm like, we just got to get out of here. Like, it was crazy. Thankfully, I think nothing ever happened after that. That was a few years ago. But— and it was interesting in real time to see a founder go from, like, nobody knows who I am, to, like, oh, now I get why some CEOs have security guards.

Oh, I can— when they talk about Zuckerberg, like, all these people having security guards, I'm like, it's probably a good idea.

Although I will say, again, I'm not going to name names, There are a couple. When I ran the Cloud 100, I dealt with a lot of, you know, software SaaS CEOs. 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.

I want to talk about one article that you published recently that I really— that the terminally online founders. Can you just share a little bit what that like?

Yeah. So I wrote this piece about how tech CEOs and also investors are just on a spectrum of highly online to terminally online. Kind of depends how charitable we're being. And it was sort of like, why are these people spending so much time on Twitter/X or just on LinkedIn online in general? you know, trying to stay up on news, trying to weigh in with people? Is it actually for their business? Is it some sort of like compulsion? What's leading to this? Because I'm guilty of this myself. And so I pinged a few founders, a few VCs, kind of people who just were in my feed a lot because I was like, if I'm seeing these people in my feed a lot, I know they're very online because I'm very online too.

Yeah.

And I literally just pinged them and I was like, hey, I think you're very online. Do you want to talk about it? I have some thoughts on maybe like, why are you doing this? And people were pretty receptive to talk about it. And I think there was a real range of responses. You know, some people said, you know, candidly, Alex, it's a really fine line between is this helping me or is this creating, you know, psychosis and brain rot? And then there are other people who are like, I frickin love it. I want to stay plugged in. I want my employees and the public to see how plugged in, plugged in I am. And I think what's different about this moment is with all this AI stuff going on, the pace of news, what it takes to be highly online and plugged in is more than ever before. Yes, I think that's the big difference, right? Like, your— what is an impressive screen time is like 26 hours a day.

Yeah, I mean, I read that. I know some of those CEOs that responded, and I I think being online to the degree that many of the— I think it's too much. I mean, I don't operate day to day as a CEO today, but there's so much shit to deal with in your business that, that you literally, to your point, you could be online for the entire day consuming content. By the way, mostly doom scrolling because everyone else is crushing it more than you and This company is doing that, and and you it's literally I I have I can't like if it it kills my my energy. It kills any execution because I just get sucked into the to that thing. And so I look at and I say if you're a CEO of a of a company that's scaling fast with hundreds of employees and all that, I don't know you know and I say that and then on the flip side, a lot of my advice to founders, especially in today's world, is when nothing really differentiates your product because everyone's vibe coding everything. There's actually a benefit to you being vocal and having a brand. So it's—

It's such— it's such a double-edged sword. It is really playing with fire because to your point, CEOs who do have a public brand have an advantage of customers really knowing who they are, knowing what they stand for, putting a face to the name. You know, one of— one of the CEOs here in the city that I really admire is Ryan Daniels at Crosby. He's become a friend, and Ryan is just always online talking about not just legal AI, which is where he is, but you know what's going on in AI more broadly. Like he had a funny post the other day about getting his wife, who's a doctor, to try Instinct, the AI assistant. And I think Ryan's personality shines through in a way that Crosby might not be naturally as well known otherwise. You know, and we were talking about Merge and Shenxi Ding. Shenxi is one of the people who was in my article as like the terminally online, and she was like, "I forgot." I love it. And like, I think it's helping Merge's visibility that Shenzi is out there. On the flip side, you can go too far. You can end up in fights with people that are unnecessary. I've, you know, I've been blocked in the past for telling someone like, hey, man, I think you should log off. Like, like, they're like, who the hell are you to say that? I'm like, oh, my bad. But now I try not to even do that. I just let it go. I let it wash over me. But like, I will see people that just seem angry online and I'm like, why?

Yeah.

Why are you letting it ruin your day? And I do also have admiration in a way for the founders who, for whatever reason, think they can afford to just have no presence.

Right.

Like another New York company, Basis, who came on our podcast. I shared the podcast episode this summer and the co-founder tweets, you know, sharing this on behalf of my co-founder Matt, who's too busy to have a Twitter account. And I was like, honestly, Matt, that's kind of goals, like, like cool for you that you just don't even need to be on there. So, you know, I think my advice to founders tends to be if you naturally want to be online, if you enjoy it and your extroverted side of you can be an asset to your startup, you should lean into it, but you should try to find healthy amounts of it. Like maybe you literally put on your calendar 3 times a day, I will spend 15 minutes on Twitter and that is it.

Yeah.

And then you're not just constantly checking it all day. I think that can work. I think it's hard to force. So if you have no online presence, you aren't the kind of person to throw hot takes out there. It can be very hard to fake it. Yeah. Like, you know, like, I think the internet, we sickos like me can spot someone who's not forcing it. Yeah. Who's not in it for the love of the game. Yeah.

All right. Last question for you. Where Where is Upstarts 3 years from today?

Yeah. So I want to grow Upstarts and stay sustainable. I want to have fun and I want to grow the business. And these are sort of points that should not be in tension as much as possible. Sometimes that can be harder than, than it is to say. So in a couple of years, Upstarts should be helping people build a career. It should be bigger than just the Alex Show. There's a reason that We are Upstarts, plural. It's meant to be an inclusive title so that anyone who's reading or watching our podcasts is getting real advice, real help to be an upstart themselves, or find from people like you that little lesson that could help them in their own journey. They could be an upstart in a big tech company or in something completely different from tech.

Mm-hmm.

It doesn't have to be go be a founder. But of course, you know, we are pro-entrepreneurship as a brand. But I also want Upstarts to be the people who partner with me, work with me, learn from me. It's not just the Alex Show. And so there was, you know, never for a second did I think I'm going to name this thing after myself.

Right.

And so that means we have to scale responsibly. We have to help people. And so I hope we have a better community. I hope that, you know, people have a sense of an Upstarts brand where they want to come to our events. They're like, that feels like an Upstarts thing. You know, that feels like an Upstarts community moment that I'm benefiting from. And I want those kind of next generation of startup builders, founders, aspiring ones to say, oh, if I see something from the Upstarts brand, this— there's a good chance this will help me in some way in my career, or it'll just unlock something I wasn't thinking about. And so it's that impact that I think I judge more than just dollars or You know, clout or virality. Yeah. Love it, Alex.

Thank you for doing this with me.

I know you're very busy. Oh no, I could have gone for three hours, man.

Thank you very much. And for those watching, I hope you enjoyed it. Watching and listening, I hope you enjoyed it. And if you did, please share this out with your network. Subscribe to Upstarts, and we'll see you for the next episode of Not Another CEO Podcast.