I’m grateful to have reconnected with Alex Konrad, former Forbes senior editor and creator of the Midas List Europe and Cloud 100 lists – and honored to be the first comms pro to connect with him in his new venture.
Now the founder and editor of Upstarts Media, Alex is the latest example of someone who charted a new course in the emerging “new media” realm. At Upstarts, Alex covers a topic near and dear to his heart – startups, particularly founders who, as Alex described it to me, “haven’t quite figured it out yet.”
Alex and I dug deep into what readers can expect from Upstarts Media, his desire to experiment with multimedia, and the valuable advice he’s gotten from peers.
Forbes taught me the art of storytelling in a way that’s really difficult to learn on your own today. What I mean by that is when you write for a magazine, every word counts: you have to make every word justify its spot in the print layout. It's so much easier to write long than it is to write short.
[Being deliberate with every word] is something that, as a new publication, I have to be disciplined about. I have to re-earn their attention every paragraph. Forbes taught me that a 400-word story has your attention for a finite amount of time. If you want it to be an 800-word story, you have to be twice as good to justify why they should spend the extra time, and so on.
My goal with Upstarts is that, because I'm only writing a newsletter twice a week with original reporting, I'm not covering every startup story, so I want every startup story I cover to matter. I don't think I'm doing my job if the reader isn’t plausibly getting to the end.
The caveat for the audience is that the podcast is still in development. I want to ensure my newsletter is in a good place before I fully embark upon it. My biggest fear is that I throw too many plates in the air and they all crash down.
How I'm thinking about the podcast right now is that it will slot in between daily, more topical talk shows and more evergreen formats. On one end, you have the old morning radio show formats – The Daily is an example of a podcast that’s done an amazing job with this – and then, on the other end of the spectrum, you have these sorts of multi-hour shows, like Acquired, or one-hour-plus interview formats, like Invest Like the Best.
For me, the gap in the market, and where I’d have the most fun, is in between: weekly interviews around a topic or a theme I think we should be discussing more. So it's not ‘tell me your life story,’ but ‘let's talk about one thing that, unless you’re chronically online like me, you didn’t necessarily fully pick up on this week.’ Or it could inform you when you talk to someone you know over the weekend.
I think one challenge for me, where the Upstarts community can give me feedback and help me out, is getting the balance right between content that has an evergreen nature, in the sense that you could look it up later and it’s still helpful – because we're all so busy – and content that can be so evergreen that it's never valuable in the first place. I don’t want it to become sanitized in a way that cuts out the juice. I have to figure out the balance there.
I had a somewhat unique situation where I was at Forbes for 12 years. That’s a long time in media. And I loved my team. My boss, whom I didn't want to leave, was John Paczkowski. He’s incredible and someone I respect. I also really respect the team I had at Forbes, from editors like Katharine Schwab to reporter friends such as David Jeans and Emily Baker-White. If anything, I feel like I stayed longer than anticipated because of that team of killers.
Giving that up was hard, but I also felt I had achieved all my objectives at Forbes. I needed to take a risk to flex new muscles and push myself to the next level of my career.
It's hard to exceed the expectations that I have now, building a new business. I'm trying to do things I never had to do before, from business development to community building, to figuring out a content strategy, all while still being a good reporter. It's a big swing chance to go to another level in my career.
I also believe this is a moment in media where going independent has a tailwind. It’s a pivotal moment for in-depth, original reporting around the startup ecosystem. I’m happy to go more in-depth there if it’s helpful.
This is a moment when so much media attention, for very understandable reasons, is focused on big tech politics and policy questions. I wrote a cover story on AI policy, and I believe that’s important, but I've always enjoyed and found that I could contribute a lot covering startups and the founder journey. I do a good job of explaining how things work, figuring out what motivates a founder. And so when I thought about what articles I enjoy writing, and what stories I think my audience resonates with, it really was that startup journey up to and around the IPO. When things were not fully figured out.
The best advice I got was to not overthink and build in public and ship experiments. Those people said your audience will be rooting for you, and they’ll be well aware you are out there on your own, trying this stuff.
On Substack, I look up to Alex Kantrowitz of Big Technology and Alex Wilhelm, who used to work at TechCrunch and has a Substack, Cautious Optimism. Eric Newcomer is another friend who has been so impressive and helpful with Newcomer.
Another old work pal is Polina Pompliano, who writes The Profile. I also read journalism-adjacent newsletters, like The Pragmatic Engineer by Gergely Orosz, who's done amazing work. I've read a lot of Packy McCormick's writing from Not Boring and Lenny Rachitsky’s Lenny’s Newsletter. All the leading tech community writers have done an incredible job building an audience and close relationships with them. I can learn so much from them.
It was great to do a story on Microsoft's turnaround with Satya Nadella and go deep with a public company. I've also done interesting ones around AI. One was more of a trend story on Marc Andreessen versus Vinod Khosla and Reid Hoffman. That was its own challenge.
If it’s just one profile, it has to be Canva and Melanie Perkins. I profiled Canva in 2019. It was the first big feature about them; the company was valued at $3 billion and not as well known because it was based in Australia. And Melanie is such an interesting tech leader. She and her husband, a co-founder of Canva, got engaged with a $30 engagement ring they found at a bazaar in Turkey. They’re Australian backpackers at heart, and they're both worth billions of dollars, but it all goes to the Canva Foundation to have an impact on the world. I’ve had people tell me they got into tech because of her story. So, from an impact standpoint, that meant a lot to me.
That was a good story! Let’s talk about it. I was thinking back about my favorite profiles in terms of quirky experiences I did, and it was a top-three quirky bucket list experience. I mean, board games in the middle of the Pennsylvania Poconos.
I almost missed the fight. I rented a car to drive to a hotel, and it’s this mountain lodge place. I still have [Appian founder Matt Calkins’] board games.
Understanding founders' passions and other things they do, even if it feels unrelated to their day job, tells you a lot about who they are, how they build, and what's driving them in a way that can make their companies more relatable. It all makes more sense.
Camping with local founders in the Utah foothills was a way to get to know Silicon Slopes. Singing karaoke with Marc Benioff in Japan alongside the CEO of Rakuten was a unique way to understand the world of leaders that Benioff rubs shoulders with. Observing Calkins winning at board games was an experience, too.
I'm interested in how I can create more multimedia stories. Coming soon to Upstarts, for those interested, will be a joint emergency pod-style episode with a founder whose startup I'm covering. We’ll both be guests on another person’s show to discuss the story. I did a live video with the CEO of Runway a couple of weeks ago. I want to do more impromptu video chats. There are so many ways to connect with startups and leaders in the industry, where the timing isn't right to do a full-fledged feature.
Over time, I plan to standardize covering one exclusive funding round and one possible deep dive on a fund or new fund announcement from a VC, every month. I'd like there to be systemization to that, where people can pitch me, and it's meritocratic: I'm looking for what, I feel, is the most interesting for the Upstarts audience. For now, send me stories that are interesting to share with the Upstarts community versus a more traditional publication – quirky or fun ones.
I want Upstarts to be inclusive for the entire startup community, where people who never pay still get value, so we'll have sponsors and other ways to make that work. But then, I also need to ensure that anyone who pays to subscribe gets great value and feels good about supporting me. And so to the extent that clients or companies can share a hot take with me, or say, ‘we could be part of an interesting trend that people aren't aware of,’ I’m interested. I know that by doing that, you’re trying to go against the news cycle to create your own. For anyone who feels like they're not using the buzzword of the moment, that could be a good reason to connect with Upstarts.
I heard a founder say recently at an event I attended, “I'm always paranoid that I can be doing more. I feel guilty even being on the stage right now, because it's an afternoon I'm not working on my business.” That resonated with me in a new way.
I want to be out there sharing the word about Upstarts, engaging with our community, and meeting audience members, but I also need to report. I'll be speaking at Startup Grind at the end of April. I'm considering doing some sort of subscriber meetup while I'm in the Bay Area. If I spend two days in San Francisco, I need to get as much out of that as I can. Similarly, I'm thinking about other cities I can go to where I could cluster a big event with a small Upstarts-focused one and reporting opportunities.
We've only been live for two weeks, so I appreciate people's patience as we ramp everything up. The benefit of the Founding Upstarts’ WhatsApp group is that it offers a direct line to me. I can share tidbits of news that don't rise to the newsletter, you can get early word on events, and my feedback on your responses. It's a real commitment for me. These individuals are serious about this news and pay attention to my work, so I'm very hopeful it's a high-quality discussion.
A number of the first Founding Upstarts are coming to my launch party towards the end of the month. I plan to find as many ways as I can, within reason, to bring those Founding Upstarts close to what I'm doing, to ensure they feel like they're part of the community and proud that they are.
If anyone has an idea for something I didn't mention, or where I could be engaging with people, I’m building in public at Upstarts Media. I welcome feedback.
For anyone asking how they can support me, the most obvious way is that if you haven't subscribed, go to Upstartsmedia.com and sign up. And if you haven't paid or are considering paying, that will be the best way to allow us to build all this faster.