Sprinting a Marathon: Alex Konrad on Building a Media Brand

Yeah, it's and sometimes both, right? So, that's what I'm figuring out at Upstarts every day.

You know, I think young Alex dreamed of being Indiana Jones, but then found out that real life Indiana Jones would be in jail right now for committing all sorts of international crimes. And so, not a great career move, it turns out. But in college, I did study pretty much every class you would think an Indiana Jones would need across the gamut. And then I had to hard pivot into a place that would actually pay me to do what I love, which is tell stories.

I was lucky enough to have some ties like friend-of-a-friend type thing to a couple Pulitzer Prize winning journalists and I did write them in college and say, 'Hey, I think now I want to become a professional journalist. What should I do to really kickstart my career?' And of course, I'll never forget the feedback I consistently got was don't do it. Which was not exactly what college age me wanted to hear. Maybe it actually helped because it made me stubborn in a weird way. And I was like, well, all these successful people are saying not to do their business. You know, they're just pulling up the ladder behind them. I'm going to figure it out. Little did I know, you know, now I would say probably to people, do it, but here are the caveats, right?

Yes, for sure.

Although I've tried to get better at absorbing the feedback of my elders and wiser people as well over the years.

I appreciate that. Some days I feel younger than others. You know, running a business, I'm aging way too fast now. So, there you go.

So, I grew up in New York City and I was lucky to go to Harvard and that's where I studied all these kind of silly things. Journalism was actually not a major at Harvard. And so, people write for the newspaper, they do other extracurriculars, but it's almost if you want to be a journalist, it's a challenge of what intellectual pursuits can prepare you. I wish I had taken computer science. I did not. But I did take, you know, anthropology and some other things that were helpful. And then got fought really hard to get that summer internship at a publication and start writing for them.

I also think I'm sure you've done this many times, it's a skill to just force yourself to cold call people or write people that you think are probably going to say no to you or tell you to buzz off. And I think that just building up those calluses to just make the ask, try to get the answer even if people think you're annoying. That's a big part of being a journalist. You know, it's hard to want to always be liked and also be good at this job.

I do for Fortune magazine in New York. And I found out that no intern had ever been published in print in Fortune. And so I made that my personal challenge and mission to achieve.

Yeah, I wouldn't tell the story if I didn't achieve it. That'd be pretty depressing. So I did pull it off with a one-page article and then they offered me a job and I started the first workday after graduation.

As a journalist, especially in tech reporting, but probably also politics and lots of other areas, I feel like you could either be a heat-seeking missile where you go really for the in-demand buzzy topic or beat and just really catch a wave there. Or you can do the opposite, which is kind of the approach I took, which is what is the green field? What is the area that nobody's paying attention to? So, maybe if I do something that people care about, it'll stand out because there isn't as much competition. And so I started to write, this is back in 2009, 2010, about startups here in New York City because most tech reporters, they still are in San Francisco, but an even higher percentage were on the West Coast at the time. And so I felt like there were these cool companies here like people might remember Zocdoc or some of these other companies, apps that they use, Foursquare, that were not getting a lot of attention. And so I started to really try to write there and build some trust. And then for the magazine story I kind of hitched my wagon to a phenomenal veteran reporter now who writes about big lawsuits and sort of court cases. His name is Roger Parloff. And you know, I sort of hitched my wagon to some of these mentors and then eventually someone had a big project and it was such a big project that Fortune said, 'Oh, we should have a one-page secondary story that sort of corroborates or elaborates on what the big one is doing.' And the main writer is way too busy for that. And so that's where I got to raise my hand and be aggressive and be like, I'll do the baby piece. And then I just tried to not screw that up.

I was really excited and it ruined me forever because I thought that being a journalist we would get to talk to cool celebrities all the time because I got to interview Robert Redford for that piece and which really impressed my mom and that's when I was like okay this is a good career because my mom is like losing it that I spoke to Robert Redford. He said, 'Call me Bob.' And I was like, 'Oh my gosh.' And then I also had a huge company Chevron mad at me. And so I was like, 'Wow, this is like straight out of Devils Wear Prada or something. This is really exciting.' That prepared me maybe or insulated me for years of grind to get back to that kind of thing. But it was like a very funny trial by fire for sure.

Thank you. I tried. I ended up going to Forbes 18 months after I started at Fortune and I ended up spending 12 years at Forbes where I worked my way from the most thankless job which was the editor of the homepage of Forbes.com back when people cared about homepages and I was literally programming which journalist articles should go on there and making the headlines fit. And I just tried to do that as fast as I could in the day so that I could do some reporting in the afternoon. And then I proved my value again as a reporter and got put on the tech beat at Forbes. And then yeah, it was over a decade of really fun times in tech reporting there.

Yeah. So, my father lives in San Francisco. It's a second city for me. And I would spend a lot of time there crashing on his couch. But I've always been based in New York City. I think being in New York covering an ecosystem that is a little bit focused somewhere else was harder but also liberating in a way because I wasn't caught in the bubble of the hype train or everyone kind of affirming each other and I think bringing a little bit of a cynical New Yorker's view to some of these startups was a healthy thing and so I would say it's a harder degree of difficulty but once I cleared that I really enjoyed being here and I resisted any pressure to ever move out west.

Yeah, I mean I had a couple interesting ones. The first cover story I wrote was about an investor who was on Shark Tank for a long time named Chris Sacca and he was involved with the early days of Uber. So as Uber was becoming very contentious and the investors were fighting each other, I was kind of thrown into that world a bit. And so that was really kind of interesting and exciting to be cited in some of the books that came out about Uber and all of that. And then I got to travel the world for a cover story on Marc Benioff which was surreal. Ended up singing karaoke with him and some Japanese CEOs in Tokyo for that story which was an experience. A funnier story, when I've had a beer, you know, we're not there right now, but I'd say the most rewarding one was going to Australia to write a cover story about this amazing entrepreneur named Melanie Perkins. She's the CEO of Canva, which is valued at over 40 billion. It's a leading design software tool, but not just for other tech people, for everybody. You know, I use Canva for my graphics, brick-and-mortar stores, grandparents can use Canva. It's a real kind of every person's tool. And Melanie is just this amazing down-to-earth woman. Grew up in Western Australia, you know, mixed background, wasn't really someone that venture capitalists would identify as an obvious investment. And she and now her husband and their third co-founder built this global iconic business from Sydney. And so it was really cool to get to be one of the first journalists to tell that story. I had to really fight to put her on the cover of Forbes. They were nervous about putting a less proven tech company like hers on there and I was like trust me or I will fall on this sword but like we will look good. And she's now been on the cover of most business magazines and I'm always really proud that we were able to lean into that one.

It helps me now. So, selfishly, I'm glad that I played some small part.

I think I should have predicted more than I did. I saw plenty of signs. You know, one of my good friends was running an AI company 10 years ago on the West Coast and he was showing me some of this stuff. A Bloomberg reporter ended up joining OpenAI early on, Jack Clark. He then left and became the co-founder of Anthropic, which is now, you know, arguably their biggest rival. And you know he will be one of the like five journalists ever to become a billionaire I guess. So good for him but also I think he cares more about the impact. But so you know you see someone like that leave Bloomberg to go to OpenAI. You hear about all this. I knew Sam Altman the CEO of OpenAI from when he was an investor, you know, long before OpenAI. And so I saw the ingredients but I will be honest that I did not expect it to break into the mainstream as fast as it did. I think when ChatGPT came out and we had that aha moment, I was having it alongside everyone else. I think one thing that my experience allowed me to do was move really fast once it was like, okay, it's here to start reporting on it and trying to explain it to our audience back then at Forbes. We did a great video about explaining what this was. We did a huge feature story about kind of the leading companies in the space, but that was all right after ChatGPT. So, I wish I could say I called it and I planted my flag there beforehand, but I didn't.

I mean, if we're going to play that game, my weirdo friend in college was telling me to buy this weird thing called Bitcoin, and I was like, 'Okay, bro. I don't see what this is.' But, you know, unfortunately I think he sold his when they were like $100, and so he got a few pizzas out of it. Not billionaire status. But yeah, if I could go back in time, it'd probably just be buy a bunch of Bitcoin and tell nobody. So, yeah.

Yeah.

Yeah, it's a tough give and take because I think that AI can help journalists a lot on the research side, on the production side. You know, I bet there's some sort of AI in this software that we're taping with right now that's helping frame us and make our faces look a little at least my face probably needs a little work to look better. So, thank you AI for that. But you know, there's a lot of little daily things that AI is doing for us, in our email or spell check and I think that all of that doesn't feel scary, and I've embraced AI for things like prepping for my own podcast. I might be like, what is a question that this CEO has answered a hundred times because I don't want to be 101 asking that question, and it can be really good for research like that. Where I don't want AI to get too involved in my flow is the actual creation of the articles, the writing itself. And I think part of it is not because I don't think it could ever be good or sort of high quality, but I think that my readers are having a relationship with me. They have a trust and a track record for Alex's work. And I think if you start to outsource that, like let's say even to a human ghost writer, that would not be a good experience. It would not be delivering on my promise to my audience. And so I think the more you start to cut corners with the value and the product that you're bringing out into the world. That's where these tools might be tempting but are I think ultimately disastrous for journalists. I think on the flip side, it can be very tempting for big organizations to say, 'Oh, let's just automate our sports reporting or let's automate our market updates.' You know, no one likes to write those anyway. And I think intellectually, yes, probably no one likes to write a basic earnings article, but I do think it's a slippery slope where it's like, oh well, we got away with that. What if we automate this slightly more complex story and you just kind of keep going until you don't stand for anything? And I think at some point the readers would reject it and say this, if they're not willing to put the human effort into this, why should I put my human effort into reading it?

Yeah, you know, I really try to avoid whenever I talk about media, I don't want to get too doom and gloom and like a downer, but I think on that specific question, it is a real challenge. And I don't say that to complain, but I think you are spot on. I'll give you an example. I wrote a couple weeks ago about a new app called Extra. It's a free email app and the whole premise is that it's supposed to be the first post-AI reinvention of an email inbox for your personal day. And the idea being, you know, we might spend so much time on our work email. We might have multiple accounts. I certainly do. And by the end of the day, you don't really want to check your personal email for, you know, when's that package arriving or did my meds come or all this sort of annoying stuff like that. And so this inbox reinvents it as just sort of a to-do list or like a here are the five things you need to know from your inbox. What's interesting about that is it also summarizes here are the three newsletters that you got today that we think you might actually enjoy reading. Now I could see that being good for those three newsletters if it actually showcases them in a more prominent place versus the promotions tab or some other inbox where you never see it. But, you know, if I subscribe to 20 newsletters and it's only showing me one to three a day, that really sucks for all the others. And that's a big concern for me because I have an audience that is a loyal audience that followed me over from Forbes, knows my work, but how do I reach those new people? How do I make them believe in me and Upstarts, especially if they're getting put into that little inbox, where it's just like, here's three of 20 newsletters that you could be reading. If they don't already have the association with me, I'm very nervous about how I would create that brand recognition and loyalty, with AI sort of as the middleman. Does that make sense?

I put in one month's notice, which felt like a fair amount after 12 years, but there's never really a good amount.

So, I've had restless moments in my career, of course, where I thought, is this the best use of my time? Is this the reporting that is the highest impact? You know, we all have doubts like this. Usually, I would fight through them. It would just tell me to maybe refocus a bit or work a bit harder, be pickier in my stories. But I think that a couple summers ago, I just really felt like two things had happened. One, I'd met all my objectives at Forbes. You know, I'd written 15 cover stories. I had managed a couple of their top franchises for a decade. And I just didn't want to look in the mirror and say, 'Oh, now I've been here 10 years, I've been here 20 years.' And the last 10 years, I just basically did the same stuff as the first 10 years. And I think if there had been exciting projects or platforms that really felt like I could keep growing in a meaningful way, maybe that would be different. But I did feel like I was going to start chasing side quests and sort of coasting a bit, maybe working a half day and no one would notice. And that's fun for a week, but it's not something that would get me out of bed in the long run. So there's a personal restlessness. Then I think on the flip side, professionally, I felt like a lot of traditional media was being sucked into covering Elon Musk and Sam Altman and some of these big few sort of billionaire names over and over and over. And you know, when you have these huge tech companies with a lot of influence, I think it's very important that we have fair aggressive reporting that is looking at these companies. But personally, I wasn't interested in being reporter 500 on the Elon Musk beat or just basically writing about whatever these guys tweeted every day like it was news. And so starting my own thing also allowed me to just kind of control what stories do I want to be covering at this point. You know, I maybe have my preferences and I have the founders that I want to be writing about 15 years into doing this. And it's also a chance to showcase people who might be getting overlooked by traditional media. And so that's why I got really excited about doing my own thing. And we launched Upstarts early last year. So it is a publication focused entirely on the startup ecosystem from inception through IPO. The name is obviously a play on startups and also the idea that I'm an upstart, you can be an upstart. Like we can all be upstarts if we just embrace a little bit of that entrepreneurial spark. And so that's what we've been doing. It's a newsletter and now it's a podcast and I also do events. So, a lot of fun, a lot of work.

I think the biggest difference for me was something that I'd heard before but I had to experience firsthand which is it is sort of like you are sprinting a marathon at all times. You know like you can't just slow down because you are going the long distance. It's a sprint every day and you don't get to really rest on your laurels or say oh we had a great day let's take a couple days off. At Forbes, I was kind of like a big game hunter where if I delivered a really big story, I did kind of feel like, oh, I could just go to a museum tomorrow or I could just not respond to email for a couple days and no one's going to come after me because they know that I just went through this intense experience. But as a founder and also running a small business, there's no one saying to you, 'Congrats, you had a big day yesterday. Take today off.' Like, you have to keep running the job. And so I think that was the biggest adjustment. But I found that just pushing yourself to do the annoying things, you can get a lot done as an entrepreneur and as a small business. And so it's been really rewarding, too.

Yeah, so we've published over a hundred original reported articles. Some really fun ones. We had a couple big scoops like when Meta last summer was trying to buy a bunch of video AI startups, we broke that story. We broke a couple M&A stories. And we've had some sort of fun articles in the ecosystem that were still punchy. And then we've also had a few interviews with people who don't really do press that really made me happy. So, I did one with this 80-year-old CEO of a company called Esri. It is the sort of geospatial software that underpins all the maps we use, like where people build a new Starbucks. Like, this guy kind of invented all of it. And he's still working. He's, you know, I think he's worth about $10 billion, but he still works full-time in his 80s. He's very low profile, though. And I think because I was an entrepreneur and I was like, you know, I'm hustling here, he agreed to do an interview with me and that was really fun because it was not just exciting, I think, for my audience, but he actually gave me business advice that was helpful. Like, you know, one thing he told me that I take to heart and I'm happy to share with everyone is he said, 'You'll think that there's one big question or problem facing you each day and if you just do really well handling that, your business will go great.' It's actually the 20 little annoying things that you're putting off for that one big thing that if you just consistently force yourself to execute on those 20 little things that compounds and your business will be more successful. So, don't just overly focus on the one big existential question. Just make yourself do the little annoying things. So, that's something that I've really tried to take to heart. And I'm glad that he was able to talk to us. I hope he'll talk to us again. And then with the podcast, we've been really lucky to have some amazing CEOs on. Melanie from Canva came on as our first guest, you know, I think because we had bet on her early, but I've had CEOs like the CEO of Harvey. We've had a nuclear energy CEO. We had this amazing CEO named Selene Halua, who's doing a dog longevity drug to make my dog live longer, come on the show. Just some really cool stories. And so I feel so lucky that I get to talk to people like that.

Yeah, it was a mixed bag for sure. I put up a signup list when I announced I was leaving Forbes and I got a few thousand people to kind of sign up for updates and that was a nice way to sort of hit the ground running. But as much as some people follow my work, I still run into people in the ecosystem who are like, 'Wait, you left Forbes?' And I'm like, 'Yeah, it's been almost a year and a half now.' But I think everyone's running their own race. They're focused on themselves. When you associate someone for a long time with a certain brand, they probably just didn't bother to check like, 'Oh, is Alex still there or not?' And so I do have to kind of suppress any ego or expectation that people will know what's going on with me and just remember that we're all crazy busy. We all are juggling a lot of info and I just have to kind of repitch myself to even people who know me all the time. There's a little bit of almost like a humiliation ritual of like people continually not knowing what Upstarts is, but at the same time, it's like, why would you? Like, I don't blame, if one of my friends started a business and I missed it, I hope they wouldn't take that personally either. And so, I've gotten very good at just laughing that off and explaining what we do. And I might do that for the next 10 years and I'll be okay with it.

Yeah. I mean, I'd say first I was lucky that I left fully by choice and, you know, I'm sure could always be like, never mind, and go back to Forbes or any of those places and they would take me back. But of course, I have no interest in doing that. I hope that I can be an example that this works and that new brands and voices can shine through quality reporting because I think just broadly speaking, the world needs more quality reporting. And as you noted, it feels like there are more stories and crazy things happening every day and fewer people who are qualified to really ask the tough questions or tell the right stories about them. At the same time, I don't want to give false hope to people that this is incredibly easy to do. You know, it was one of those businesses that I'm sure this would resonate with you in your career. Like I spent a long time building the credibility and the network to go do a lot of what I do. You know, I don't think this would have succeeded if I tried 10 years ago even, let alone at the beginning of my career. And so I think that there is something about sort of I want there to still be a system in journalism and media where people can train, they can learn, they can have the mentors that I was lucky to have. I hope to be one of those to people, but I can't solve the problem entirely, but I hope that we can be both an example and a trainer for a new gen to build off of what Upstarts is doing, improve off of it. I plan to hire people and grow this brand over time, but I also hope that we never become like what I left where sort of there's tension in traditional media between rewarding your star employees and reporters and making the bottom line, right? Because I think the reality is a lot of traditional media struggle to be profitable. And at some point when you're an employee delivering a product, you are creating a margin for your employer. And I think it's just structurally really hard for any big publication to fully reward their star talent and still run the business as it currently stands. I think that's why you see so many of us saying, 'Okay, well, we'll just do it ourselves. Don't worry about it and we'll make it work financially by finding partners, by finding audiences, and just sort of taking it into our own hands.' So, I think that is a solution. I don't think it is like the solution on its own, if that makes sense.

You know, that's a great question. I think overall yes, but I think it's also humbling because I am used to talking to people who are way smarter than me in their field and there's a lot of people out there smarter than me and I've learned that from the thousands of entrepreneurs I've met with. And so I think on the one hand, it's not rocket science to start a business, to honor your obligations, pay your taxes, do all that stuff. It's just kind of annoying, but it can be done. And I think I felt good about that. I think on the flip side, you have to just sort of sometimes not overthink things. I think I have been around all these geniuses who had a breakthrough technology or something. What I'm selling is not a breakthrough technology. You know, I'm trying a different flavor of podcast. I'm trying a different flavor of media company, but it's still a media company and my journalism is still the core product. And so, in that sense, what I'm doing is not crazy disruptive. And I think just not overthinking it and just thinking, you know what, we're going to just show up, do what we say we're going to do, deliver a good product, try to have fun with it and show that we're having fun to the audience. That will sort things out. That has been sort of my response to when I meet with that nuclear energy CEO or that person making my dog live longer. And I'm like, I would have never thought to do a business like that. That's just like a completely different world for me.

Oh, I have fun with it and I'm always networking. I hope we will stay in touch. I hope anyone who is enjoying this conversation can reach out to me on Twitter, email, like just responding to people and being curious and actually liking talking to people is such a skill that I hope everyone can embrace. And so I've done it for a long time and I enjoy doing it, but I have to keep doing it every day, you know. So the day that I am sick of talking to new people will not be a good day for my career or for I think my happiness. So long may I continue.

I appreciate that. If you have any suggestions of a good hat for the sort of journalist archaeologist, that's one thing I don't have as you can see, but I'll embrace the unearthing part of it for sure.

Absolutely. So an easy way to find the newsletter and all our written content is upstartsia.com. It's free to subscribe. There's some paywalled stuff if you love it, but totally free. And then similarly, you can find our podcast wherever you get your podcasts. That's Apple, Spotify, YouTube. It's the Upstarts podcast. And I will be excited for any feedback on how we can, you know, improve and grow the show and what we're doing in the years to come.

Thanks so much for having me. I hope we can check in some time and see how we're both doing.