It's probably the most exciting time ever to be building a startup and also arguably the most chaotic.
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Welcome back to the Further Faster podcast. I'm your host Jeff Becker, general partner at Antler here in New York. Today we have Alex Konrad in the studio. He has over a decade of experience as a senior editor at Forbes. He's had the best seat in venture capital for over a decade doing amazing things like editing the Forbes Midas list, expanding it into Midas Europe and the Brink list. He is the creator of the Cloud 100. He covered the SVB collapse and the Sam Altman saga around his ousting and he won an award for that work. He has 15 major cover stories on Stripe, Canva, Whiz, and so many more. I can't wait to learn how to be a better podcaster from Alex today in the studio. Thanks for being here.
Yeah, thanks for having me. And you know, now I'm a founder, so every day all those accolades don't mean much when I'm trying to remind people who I am.
Yeah. Well, you know, you actually say nobody cares, right? This is what he thinks.
Yeah. It was actually, I've heard it from a few founders, but it was really said well to me recently by Ryan Peterson, the co-founder and CEO of Flexport, where he basically said that by default, nobody cares about your startup and that that's a healthy thing, you know. And I think, you know, his point was your startup should always be tapping into something bigger to earn people's attention, but by default, we're all running our own race. And that's something I try to really take to heart in life. Especially when you know people are like, 'Oh, did you start something new?' And I'm like, 'Yeah, I've been doing this for a year and a half now, but happy to explain what it is.' Yeah.
Well, let's tell people what it is. We're now the founder of Upstarts Media, the blog, the podcast. It's been amazing to watch.
Well, you're explaining it, you know, perfectly for me, but yeah. So, Upstarts is a new media brand. We have a Substack-based newsletter. We do some events, and then we have a weekly show, video first, like this on YouTube where we talk to emerging startup leaders every week. It's a lot of fun.
Amazing. Well, from my seat, it feels like a lot of people care. I see them posting your content. I see them sharing it. What's your experience of being a founder now that you're on this side of the table?
Yeah, I mean, I think controlling your own destiny is so refreshing. And I am working the hardest I ever have in my career. And it's just sort of natural. You can't really imagine not doing it. You know, like the idea of walking home from a dinner with my wife and not checking the notifications on my phone and not getting back to people because it's like 10 p.m. just doesn't even occur to me now, you know, whereas I think when I was even a pretty senior employee at a bigger company, I was resentful or I was kind of trying to carve a little bit of my time back, you know, like there have to be limits. And I think when you're a founder, there's just so much that you want to do that you don't have time to do that you never think to yourself, oh, like should I be unplugged right now? You know.
Totally. And but you have interviewed some of the most iconic people in venture. I imagine you've just learned a ton from them. What are the things if you can share for the listeners that you're bringing into this role that you've learned having sat across and interviewed some of the best minds in the game?
You know, I think one of the biggest things is you have to really love what you're building because if you are trying to do it cynically and reverse engineering a big company, running a startup is a terrible business to do. Like go make money at Google, go make money at OpenAI if you can get the job there. But like, you know, don't do the startup for the glory, for the money. You have to actually have a love of the game. I think that's really feels obvious, but it's tougher in this moment where it's AI everything and people are like, 'Oh, AI is disrupting all these verticals. I should just pick a vertical and start a company there.' If you don't love that vertical, it's going to be a lot of years of grind, right, for maybe an outcome. And so for me, that's one thing is I love to talk to founders who have been working on their company for, let's say, over a decade.
I recently did an interview with Eric, the CEO of Zoom. He's just finished 15 years of building Zoom, you know, and they went public six years ago. And it's like, why is he still doing it? He's a billionaire. Like Zoom had this massive moment during COVID, it's still around, but like if he wanted to retire and ride off into the sunset, I don't think anyone would hold it against him, but he just has a love of the game, of the impact, and I think you'd have to pull him out of that company. And so that's been one of the big lessons for me.
Yeah. Are there things that you've noticed in the earlier founders now that you're interviewing the upstarts that help you understand if they're doing their life's work or if they're kind of chasing a moment? Do you have any ideas?
Yeah, that's a great question. I think that I've decided that the people who are investing in the lifestyle, unless there's a very tactical reason that I can see for why they're doing it, that's a big red flag for me. You know, I think if you are speaking at a bunch of conferences, renting a Lambo for your launch video, I want to know like why that's helping the business, right? Because one of the first things that happened to me, and this might resonate with you, too, is maybe a month into starting Upstarts, I spoke at a conference in Miami and the whole time I'm like, why am I here? I should be back working on my business. Like, god damn it, I'm in Miami. And you know, maybe a few years ago I'd be like, oh, free couple days in Miami. Let's go party. And instead I'm just like what an opportunity cost and a founder basically says this on stage and I was like that guy gets it and that was a real switch moment for me for sure.
It's like the founder guilt of when I'm at home I'm not working on the business there's so much to do but when I'm at the business I'm also not home and there's so much to do and how do you balance that and how do you get comfortable in that because I think with anything meaningful that you're working on the road map is endless like you could just work and work and work and I'm curious how you balance that. How do you think about what's important?
Yeah, I think that we're in a moment of performative grind culture for a lot of people and I'm definitely allergic to that. So like one thing is you will not see me brag about how many hours I've worked in a week or like you know complaining that I'm working on a weekend cuz I feel like all founders should be working on the weekend and we don't have to advertise it.
You don't have to be bragging that you work on the weekend like it's your business, you know? And it's the same as our parents and our grandparents small businesses that they didn't call startups that didn't get a lot of attention or accolades. You know, my mother-in-law ran a women-only gym in upstate New York. My father-in-law, you know, built his own chiropractor business. Like I've had on my own family side, you know, we've had entrepreneurs, too. But this was just like a grind, you know. No one was like, you know, hell yeah, they're working the weekend at the gym, you know, living the dream. Yeah.
And so I think that for me that's just table stakes and then it's about how do you work smarter because I think pulling an all-nighter is not good for either of us. At least in our sweet spot of our career. Maybe when we were in our early 20s that seemed glamorous but now it's like there's a real opportunity cost in pulling an all-nighter and being wrecked the next day. So unless the business needs that in that moment that's not working smarter. Yeah.
You know, and it's how many founders have said to me that running a business is like sprinting through a marathon, right? You know, and it's like so I have to try to keep myself back in a way because I don't know about you, but I'm someone who can definitely overdo it and feel a little burned out. And you don't really have the chance to do that as a founder.
I think when founders are like a bit of a professional OCD. It's like a puzzle you got to fix. And so there's always something there's always another piece to put in there. It's like when do I stop? When do I put this thing down and come back to it with fresh eyes?
I wanted to touch on this performative grind culture you mentioned. I think the media is really rewarding the high valuations, the hustle culture, but I've noticed in a lot of your reporting that's not the thing you're focused on, and I'm curious your approach to that and your view on that for founders and for people that are covering it.
Yeah. I mean, again, I think one nice thing about calling my own shots is I don't need to write about companies that I don't want to be profiling or promoting unless I think they're doing something really interesting or it speaks to the wider ecosystem. And so, if you have some stunt around how hard you're working or how you're sleeping in the office or something, you know, that might impress some people, but it doesn't impress me. And so, I just don't need to shine a light on that. Now, if I was trying to write a story that was raising serious questions around what kind of people go join a startup where they sleep in the office, like maybe if you could make the case that you get a different kind of engineer or something and there's a real business value, then it's like, okay, we can have that debate. But just the idea of sort of eulogizing some of this grind stuff, it's just not appealing to me at this point in my career. You know, I've written about startups for over 15 years. I've met with thousands and thousands of founders, as have you. And so I think those trappings of legitimacy just don't appeal anymore. And I do gravitate towards outcomes for customers, outcomes for everyday people, potential for impact for these startups more than like what is the glitz they're getting along the way.
Yeah, I think we noticed this in the SVB coverage in the ZERP era. In some ways it feels the same from a media perspective or maybe the caliber of people chasing the caliber of ideas and what's getting funded and so just trying to like kind of pull the weeds back a little bit and be like what's durable here.
Well, I think one problem is you know the valuations and the funding rounds for these AI companies are so insane that it makes small numbers look even smaller. You know I had a company try to pitch me the other day a $2.5 million funding round and I almost think that number doesn't matter anymore. It's like pitch the merits of your company, pitch the idea you have, but no one's going to care that you raise $2.5 million when a pre-product AI company could raise $2.5 billion. So I think the numbers are all out the window. That said, that could be liberating, you know, because if the numbers don't mean anything anymore, don't live and die by those numbers. You know, get people to care about other milestones you have like customer wins or traction. And don't, you know, try to impress people with whatever your series A was or your seed.
Yeah. So, how do you choose a story to tell? I mean, there's all these stories out there. They feel kind of easy, like low hanging fruit on a big round, but then the ones you're telling seem to be like the real meat. How do you identify that?
Well, the real trick is you have an autoresponder on your email inbox, okay? And anyone who can sneak past it and find the way through it is showing the hustle that you should write about them.
No, I mean that's half kidding but half serious.
You're going to get a lot of people following up two three times now that watch this.
You know, you think that, but I find that people are very lazy. And they are outsourcing a lot of this stuff to like ChatGPT. Yeah. And the sheer volume of email pitches I get that are clearly AI generated and even AI generated follow-ups that are trying to guilt trip me. Yeah. Are kind of surprising. Like these are also very smart founders. So I'd love to have those people on, you know, one of our shows and be like, did you think this would work? Like what data suggests to you that this does work? Because it's really low-hanging fruit. I think for me the serious answer there is that I have very trusted networks that I lean on more than ever. You know, referrals from other founders, referrals from investors. I like, you know, companies that have been on my radar and the founder reaches out and I kind of already have some familiarity. You know, that said, like you don't want to be overly close. I'm sure it's like you as an investor and I will take that hail mary cold intro from a founder I've never met. But I think the bar is higher to impress when you're just coming in totally cold.
Yeah. You kind of touched on this laziness like what we're seeing in our business is the presentation layer is totally collapsed. Yeah. I'm getting, you know, 100 Claude-built decks a day. Yeah. It's hard to tell what's real and what's not. Even people I really respect that are writing great stuff, you're seeing like phrases like 'here's the flip' and you know the things that AI is writing.
Yeah. I mean we've reached a point where everyone writes in X blog posts all the time at least if you're a VC. Yeah. I have no interest in reading those posts because I don't have time to find the one out of five that a human actually wrote, you know. So like one framework I have for people is just if you're doing something with the AI, the AI tool, expect an AI tool level response, you know. Don't send me an obviously Claude or ChatGPT generated pitch and get upset when I don't send a long thoughtful human generated, you know, pass email back. Right. I'm curious if it's the same, you know, passing as a VC.
Yeah. I mean, I think that you can tell instantly if someone has taken the time to be different by design, if they are, you know, evaluating what's in front of them and doing things differently because it's going to give them a leg up over someone else. And I think where AI might be great in terms of helping people get closer to center, like things like politics, in venture, it's different. I'm looking for outliers. I don't want someone who's gonna present to me what Claude presented to them.
Yeah. And so it may sound obnoxious a little bit, but I do think that if you're a founder trying to fundraise or get press coverage, if I'm trying to get in front of let's say a hard to get founder to come on my podcast, you should be playing angles to maximize your chance of success. And the more that you're able to hustle and kind of show the creativity to get to that person, I think it is validating to them to improve your chance that they will say yes, whatever it is. You know, there are plenty of founders who I can't get to come on my show that I'm trying to get them. And at the same time, there are all these founders kind of coming into my inbox trying to get coverage. And so, we all have that person that we're trying to reach. And I think you have to show the hustle to get to them.
Yeah. Tell me more about this playing angles. Do you have some examples or how do you think about getting, I mean you've been in the best rooms. What are some angles that you might recommend or things you can share?
Well, I think you know being in person in front of people is always huge. You know, like how many founders have said to me that one of the big lessons they learned is get on the plane. I think that's also a YC tenet. You know, for better or worse. I don't know if we're allowed to talk about YC on this show, but it's okay. Yeah. Well, you know, one of the long mantras is just get on the plane. And I think that's true for everybody. And so if you can find a conference or a scenario where you rub shoulders with a person who's impossible to get a lot harder for them to say no in person, right? So I was at a conference called HumanX early this year and there was an unnamed AI unicorn founder whose PR team had said, you know, they don't have time to talk to you. I don't think they really knew what Upstarts was. Like I could tell, you know, they were kind of like, who is this guy? And that's fine. And you know, people don't always know a new brand. So yeah, I just found them in the green room and I just went up and was like, 'Hey, how you doing?' Like, 'Good to see you. Let's chat for 5 minutes. Hey, do you want to come on the show?' And then I emailed them directly and CC'd the comms team. And it's a very different story, right? Very different. So, getting in front of the person, I think, is number one.
I think number two is finding something they really are passionate about. You know, I think we see this especially with the Collisons with a lot of the cool work they're doing, but founders are often passionate about a topic or a problem in the world that may overlap with their company, may not always be directly. If you can genuinely approach them about something you know they care about, I think they will make time. Yeah. Right. Like I was just reading that Jensen agreed to donate a leather jacket to a Silicon Valley charity auction. Amazing. And like I'm sure Jensen replies to like less than 1% of outreach he gets. But for a charity auction that resonated with him, he was like, 'Sure, you can have one of my leather jackets.'
Great. I love it. We got to figure out where to go bid on one of those.
Yeah. I mean, that's for you. I can't afford that, but I'll let you do it. No, we'll just stay to the green.
Okay, fair enough. Yeah. Yeah. I love it. When you're in the rooms with these people, how do you prepare? How do you think about the angles you want to go after and approach because you've been able to break some amazing stories and cover some amazing events in venture. You're not only there, but you're there very early. I'm curious some of the approaches and tactics.
Yeah. Well, I think you just said it, which is you want to be there early, right? I think that there are probably founders that you've wanted to invest in where by the time you met them it was kind of too late for there to be an opportunity and maybe if you had been able to just by chance or hustle befriend them two years earlier you would have had a shot on the goal and I think that is the case when you're trying to interview or write a story about people too is building the relationship before both parties need something is going to be so much more genuine. You know, I write a lot about founders that I'm just meeting, but I think my most fun interviews, my best stories are when there has been time to build a rapport. For example, someone I know, you know, is Celine Halioua, the CEO of Loyal. One of my favorite interviews of the past year, she came on the podcast and it was like a reunion of friends who are just on a riff. And I think that really shone through in the interview and it made for a better, you know, user experience. It made for a more fun interview. And that's something that required a bunch of work in advance, you know.
I noticed it when I watched just the banter you guys had, the rapport. It was just so natural. But she's also amazing. What she's building is legendary. And it's just so interesting to watch. And here she's made so much progress in such a short time, right? Dog longevity resonates with people. She is passionate about it. She's got charisma. So it does make for an easy interview and you can't fake that. You know, if someone is really dry in front of a camera, there's not a lot you can do about that.
But I do think that spending time with people does often help. A tip that another podcaster gave me that I don't always use, but I'll give to you and anyone else who wants to start a show, please, is try to have coffee or take a walk with your guests in the day or two or even the morning of your taping. Yeah. To kind of just get through some of the nerves and the sort of chemistry stuff so that then when you sit down it's like you're in the middle of the conversation.
That can be hard for me when some of these CEOs like they come in with a whole team and they're like you have 53 minutes and then we're all out of here like the Uber will be here in 55 minutes and I'm just like that doesn't set up the most friendly conversation.
Yeah. It's like an entourage and a military schedule.
Yeah. And it's also then it's just like you're checking off a box. It's not like the CEO is just hanging out to sort of talk to a peer, which of course my startup is smaller than all of theirs, but that is more the vibe we're going for.
Do you have any go-to questions or things that break the ice? Things that can warm you up to a Sam Altman or, you know, Keith or any of the one-name investors and founders you've met?
I mean, I usually just talk about stupid stuff I've seen on Twitter. Yeah. I think like I'm a highly online person and so whether it's something that we were both joking about or it's something that I can maybe share with the people, I am definitely the annoying friend who is like did you see this meme? Did you see this? Did you see this? And then what's funny is my wife is like that too. And so a lot of our marriage now because she also works in startups and we both work a lot of hours is Twitter DMs to each other. Did you see this? Yeah. Did you see this? Yeah. It's our love language I guess.
Did you see the Brian Chesky news this week?
Yeah, of course. I was sharing that with a lot of people. I've been tweeting about it up until this taping. I find it so interesting for people who are not aware of this and I was the friend telling people how basically the CEO of Airbnb posts this thread online about possibly doing a side business in crypto. And everyone believed it and then he deleted it and everyone was like, 'Oh, did he just delete it because people were making fun of it?' and then it comes out, oh, maybe he's hacked. And I just thought it was such a like 2024 in a nutshell kerfuffle for me. So, that is the kind of thing that distracts me all day.
Yeah. Like both totally believable and interesting that someone with that profile could get hacked and then the way he announced it. And it's the funny thing about social media still is like, you know, someone like Sam Altman, you try to do a scheduled interview with him and they will say, 'Oh yeah, we're free, you know, maybe in 12 to 18 months or something.' Actually, I won't say who, but I have someone booked for an interview with me already in mid-October. Wow. You know, and we're talking now in the middle of the summer. So, I think like it's a reality that people book out this stuff really far. But then on social media, like I wrote an article about the CEO of Figma, Dylan Field, making kind of a joke at Sam Altman's expense, and Sam tweeted 'too soon' at it. And of course that blew up, right? So that was the comment that I got that was unsanctioned by the PR team.
Did you see Dylan and Sam Altman were in that show Mafia? It was the Founders Fund. They're playing a game. You seen this?
Yeah, it was really smart. It was a, you know, I grew up calling it Werewolf. Some people call it Mafia, some people call it like assassins or something. But yeah, it was that game where people lie to each other, right? And they had a lot of big wigs and it was honestly very clever of their fund to kind of get those people doing this kind of lying game with each other, right? The only thing that could have been spicier is if they'd gotten Dario from Anthropic also play against Sam.
That's it. Yeah, maybe we should do an Upstarts Mafia.
You know, I did think to myself like is there an angle here for me? I do think generally speaking VC firms, new media brands, we should all be more creative in trying to do fun stuff like that. I give them a lot of credit for just like having fun. It clearly resonated with people.
Yeah, I loved watching it. Are there types of content or things that you've been toying with that you maybe new formats or new creative structures as you bring it up?
Yeah, I mean I think we are looking at hopefully doing live podcast tapings. That could be a lot of fun. I'm trying to think about more interactive events that are not just dinners. You know, obviously founders are so busy. We talked about how, you know, everyone goes to something and they're like, what could I be doing right now for my day job, for my business? And so thinking about are there sort of like more role-playing type games or prediction challenges? Yeah. Yeah. Where founders could maybe have some fun and also be gaining some insights or unlocking a different part of their brain. I would love to do more there. Yeah. Nothing to announce just yet, but I can tell you that I was talking to a founder about this literally yesterday.
What is the media not talking about right now? What are the stories that maybe aren't getting enough attention?
Yeah, I think one challenge is you are kind of bound when you're in an attention economy by what people actually are reading and spending their time on. And this is a real challenge for me with Upstarts because some of the most viral pieces we've had, the ones that drive the most subscribers are around the heat-seeking missile topics that I think are less exciting or sort of quirky or just differentiated to be covering, you know? So startup leaves OpenAI to do a new buzzy AI startup or you know scoop around some big funding round or acquisition that you could have read a similar story in The Information or Bloomberg or Forbes that doesn't feel signature to Upstarts, people will still go to those articles and so to some degree my challenge is I'm trying to lead people to the curated coverage that maybe they wouldn't read otherwise. I think that's a challenge that I can do because I have faith in the long game. I have a bit of a platform. But I think if I was, for example, only trying to grow my subscriber base as big as possible or if I had venture backing and growth was my top metric, you would see me get pulled into the same articles that everyone else is doing. And I don't think it's bad intention that reporters overly cover SpaceX or OpenAI or something like that. But the sad reality is that those stories do well. You have a business. And so it's sort of like how much am I giving the customer what they want, right? It's like the mad lives of major media versus something I actually want to cover that's interesting and useful to the world.
Yeah. No, it'd be like, you know, if a founder had a confectionary business and they could get us all hooked on candy to a new degree, like, would that be a bad thing? Would they be able to sleep at night? Would they be like, 'You know what? I'm only going to give them so much candy.' Like we're cutting off our own customers from too much candy, right? And I think some of this coverage around the big AI companies is the candy right now.
Okay. Yeah. The 2024 trend will be candy maxing.
Doesn't go well with look maxing. Yeah. Maxing, looks maxing. How do you draw the line between optimizing for likes and views versus the good stuff?
The hope I think is that in this moment of lots of information, lots of hype that people do over time trust curated voices, authoritative voices. And I think, you know, someone like Ben Thompson with Stratechery has done an amazing job building a loyal audience and a trusted brand. He's someone that I look up to a lot. You know, there are some podcasts like this too, Acquired. I think everyone thinks, okay, they are very tasteful. They choose their battles. They do not follow the zeitgeist. They create one. And I think that's where we aspire to be with Upstarts. It's a daily struggle though because you will write some pieces or have some guests that don't hit the algo that don't go viral, you know, and it doesn't feel as good, you know, from an endorphin standpoint, but you're maybe trying to just have the slow game of, you know, we are showing a body of work. We are showing a body of trustworthiness that will pop and sort of pay off down the road.
Yeah. Yeah, but I think it's a really tough challenge and it's one that frankly keeps me up at night all the time.
Yeah, I commend you for it because I can when I read your posts and I see your blog and your podcast, it is not like the rest of the media. It does feel like I'm getting real information and real content and things that matter and learning as opposed to reading a headline.
