Kevin O'Connor on backing visionaries, the future of VC, internet history and more | E1861

8 Dec 2023 · 56 min

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In short

This Week in Startups: Episode E1861 - Kevin O'Connor on Backing Visionaries and the Future of VC

Episode Summary In this episode of "This Week in Startups," host Jason Calacanis welcomes Kevin O'Connor, co-founder of DoubleClick and current venture capitalist at ScOp. They discuss the evolution of the internet, the impact of AI on various industries, venture capital dynamics, and the qualities that define successful entrepreneurs.

Key Topics and Discussions

  1. Early Days of the Internet
  2. Initial Impressions: O'Connor recounts his skepticism about the internet in the early '90s, noting that significant developments like T1 lines and web browsers sparked his interest.
  3. The Theme of the Internet's Evolution: He highlights the core theme as reducing friction, enhancing efficiency, and ultimately democratizing access to knowledge.
  1. The Rise of AI
  2. Current AI Landscape: O'Connor reflects on the transformative potential of AI, particularly with the advent of ChatGPT and its impact on industries like Hollywood and music.
  3. Long-Term Expectations: He anticipates a seismic shift similar to that of the internet era, emphasizing that AI could enhance productivity across various fields.
  1. Venture Capital Insights
  2. Investment Strategies: O'Connor discusses the importance of investing in companies that have achieved product-market fit, specifically those generating around $1 million in revenue.
  3. Building in a Down Market: He emphasizes that downturns can create opportunities by filtering out less viable companies and focusing on sustainable growth.
  1. The Concept of "Death-icorns"
  2. Emergence of Unprofitable Startups: O'Connor introduces the idea of "death-icorns," referring to startups that raised significant funds but failed to reach profitability, often due to debt-financed growth.
  3. Advice for Founders: He advises entrepreneurs to prioritize solving real problems and maintaining financial sustainability over chasing inflated valuations.
  1. Qualities of Successful Entrepreneurs
  2. Traits of Visionary Founders: O'Connor outlines the importance of resilience, a strong sense of urgency, and the ability to pivot based on data-driven insights.
  3. Delusional vs. Visionary: He highlights the fine line between being a visionary and delusional, stating that he often prefers backing those who may appear delusional but have a compelling vision.
  1. Future Trends in Work Culture
  2. Remote Work Dynamics: The conversation explores the challenges and benefits of remote work, including issues of socialization, mentorship, and productivity.
  3. Impact on Talent and Hiring: O'Connor discusses the competitive landscape for talent, particularly as remote work allows for a wider pool of candidates, sometimes leading to lower salary expectations.
  1. AI's Long-Term Viability
  2. Commoditization of AI: O'Connor warns against the notion of AI becoming commoditized, suggesting that proprietary data and specialized applications will be key differentiators in the market.
  3. Future of Language Models: He anticipates that while foundational models will be widely available, competition will center around unique applications built on top of these models.

Key Takeaways

  • Adaptability is Crucial: Entrepreneurs must be willing to adapt and pivot based on data and market feedback.
  • Focus on Core Problems: Successful businesses are built on solving significant problems rather than chasing trends or high valuations.
  • The Importance of Strong Leadership: Founders with charisma and vision can inspire trust and support, making them more likely to succeed.

Conclusion Jason Calacanis and Kevin O'Connor's conversation provides valuable insights into the evolving landscape of technology, venture capital, and the traits that lead to successful entrepreneurship. Their discussion emphasizes the need for resilience, adaptability, and a focus on solving real-world problems as essential components for success in the startup ecosystem.

Episode Links

  • Subscribe to This Week in Startups: [Apple Podcasts](https://rb.gy/v19fcp)
  • Check out ScOp Venture Capital: [ScOp](https://www.scopvc.com)
  • Follow Kevin O'Connor:
  • [Twitter](https://twitter.com/kjpoconnor)
  • [LinkedIn](https://www.linkedin.com/in/kevinoconnorsb)
  • Follow Jason Calacanis:
  • [Twitter](https://twitter.com/jason)
  • [Instagram](https://www.instagram.com/jason)
  • [LinkedIn](https://www.linkedin.com/in/jasoncalacanis)

This episode serves as a valuable resource for anyone interested in the intersection of technology, venture capital, and entrepreneurship, particularly in today's rapidly changing environment.

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Transcript

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0:00the best line i ever heard the hardest thing about being a vc is um figure out their founder is delusional or visionary uh it's very fine line line if they're right they're right they're wrong then they're probably delusional i'm willing to beth the delusional ones for sure because if you're delusional and you say yeah you know i think there's something out there and you leave spain on a ship with some provisions yeah you got to be pretty delusional to think you're gonna hit land because you might not i like the delusional ones because if they hit land now they're visionary like you're saying well i'd say i'd put that in the visionary camera delusional are the ones that just refuse to listen this week in startups is brought to you by Northwest Registered Agent.

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1:21and DevSquad. Most dev agencies only offer developers. Why? Because product management is hard. Get an entire product team for the cost of one US developer plus 10 % off at devsquad.com slash twist. All right, everybody, welcome back to the program. Our guest today is Kevin O 'Connor. I met him 28 years ago in 1995. I was running a little magazine called Silicon Alley Reporter and kevin had just started an internet advertising company called double click you remember double click what by google eventually it was founded uh i remember going to poppy tyson on 23rd tree we talked about it the last time you were on the show kevin which was episode two three four so here we are a decade since your last appearance on this week in startups and uh i guess we're getting close to 30 years since you and i met in new york at the dawn of uh the internet so welcome back to the program, Kevin O 'Connor.

2:20It's good to see you again. It's been a long time. It's a, we see each other every 10 years. We do an episode. You know, an interesting place to start would be when you look back on what's transpired since 1995, when we were on those dial-up connections, and then we started getting T1s and ISDN lines, and the browser started supporting rich media, and you put some of the first ads on the internet. When you look back at what happened to the internet, what is the theme as an entrepreneur and now an investor that sticks with you the most? I think our original hypothesis, and when I first saw the internet, probably early 90s, I wasn't impressed.

2:542400 bond modem, the browser hadn't come out. And I was not impressed. It really wasn't until the T1 lines came out and the web browser, I said, to have a system where anyone in the world can access the world's knowledge for free, that's a big idea. It's going to be huge. I remember our original business plan. I forget what we had. I thought we forecasted something like 10 ,000 servers and maybe 100 million people would be on it in 10 years. People thought that was crazy. And it was crazy. We were way off. It's like 100 million servers or websites and a billion users online. So I think the theme is...

3:36Back in the old days, people talked about the new economy. And I always thought that was kind of BS. There was no new economy. It was just about reducing friction. And that's what I think that's been. That's been the promise. And that's what's happened. Just made things more efficient, more timely, cheaper. And when you look at that efficiency now, AI has emerged and all this information that was put online, three decades of people just pouring their hearts out and scanning every piece of information, every piece of art, mapping every nook and cranny and scanning every book and writing every comment under every video and every blog post now has resulted in.

4:15what feels like some form of intelligence or knowledge processing that could be very transformative. So what's your expectation here as we just wrap up the first year of chat GPT being a public phenomenon? Obviously, you know, 3.5 of open AI's chat GPT kind of was the starter's pistol last November. And here we are taping this November of 2023. Is this going to be a similar story or a bigger story than the internet itself well you remember back in 9500 companies were pitching ai even back then right they're going to predict everything that you're going to do and and ai faded away because it just never delivered on its promise and i don't think chat gpt the 3.5 version it was interesting you know like it was the best chatbot out there uh 4.0 blew my mind away and definitely realization that this is a fundamental shift i mean usually once every 10 years, there's some cosmic shift, whether it's EC, so network, to internet, to mobile, to SaaS.

5:16And we're due for another seismic shift. And there seems to be two camps forming on AI, as there always is with technology. It's the hand-wringers, like it's the end of the world, everything is over. Oh my God, chicken little. To the optimist, like I am, which is technology is great. What could possibly be wrong with something that can actually turn information into knowledge and make people smarter, you know, more intelligent, make better decisions. It's, it's phenomenal. And when you look at the impact you think it's going to have, we can parallel it with the internet. And I'm with you. I mean, it seems like there's a ton of upside here.

5:53There's going to be some downsides, obviously. We used to have typing pools, we used to have messengers, we used to have people sending postal mail, FedExes, a lot of those things got hit pretty hard when people got email um but you know when you look at the first year and you think hey in year two because in the first year it feels like people are playing with it and starting to implement it but in year two i think it's going to get more serious so where do you think we're going to see this land in 2024 what industries will have the most impact on well i think the surprising thing at least in my mind uh we always thought i was a i was a developer for the last 10 years and you of the computer sciences exploded over many, many years.

6:38And everyone went into it thinking that job will never be at risk. That's a safe job. Now, the safe job. And now it's like, I remember being on a call with a company. They were telling us, I do venture capital now, they're telling us how complicated and sophisticated the technology was. And I was kind of calling bullshit on them. And I asked ChatGPT to write the code of their product that I posted in our chat. I said, there's your product right there. So jobs like that where I think legal is going to be dramatically affected. I think accounting. It's so hard to predict technology. The internet everywhere back in the days, they're trying to figure out what was going to be hit the hardest.

7:21And when you look back, I'm not sure any of us predicted. None of us predicted Amazon. Amazon was a bookseller. yeah so you know it has a strange new technology has a strange way of affecting it's going to affect every industry to some point i think large language models have its place as a foundational model i think large language models are probably more like the internet it's going to be the stuff that's built on top of it or for the verticalization to highly specialized language models that are going to probably have the biggest impact yeah it's quite paradoxical if you narrow the scope of the language model to code, it does a better job.

7:58And if you point it at a code base, well, it's going to educate the new developer as to that code base. So starting day one at Slack or Salesforce, it's just you're going to get up and running so much faster, you're going to be, you know, it's going to complete half of the of the code snippets you write. And it does make sense to me that accounting and legal also fall into that there's a corpus of work that is finite that is rule-based um and that is repetitive right i mean and there is some thread here we could pull if it's repetitive and there's a finite rule set and it's there's a corpus of work it could be you know automated and ai could could do it pretty quickly huh well hollywood's going to be greatly affected right you do think that yeah this is a big debate Oh, it's going to be...

8:47I mean, think about it. It's a finite number of stories. It's the same story that came out of Greece 3 ,000 years ago. It's just being retold with different characters. The fact that any of us would be able to put that... We'll be able to build our own movie. I think then it becomes a little bit like YouTube, which is... Or Instagram, where the amount of content is exponentially increased. Most of it is just total garbage. but there's going to be that phenomenal once that sort of rise to the top that go viral same thing with music i mean music is pretty you know you can imagine i mean my prediction is that definitely within the next five years uh the number one song will be written by ai that makes total sense we've had many number one songs that were um using samples right and rehashes of old songs so if ai can interpret all of that base of knowledge yeah it's going to hit one for sure There's no doubt about that.

9:43And yeah, there's only a finite number of movie tropes, you know, quest, comedies, rags to riches, beat the monster, tragedies. It's a certain hero's journey. It's a certain corpus that, yeah, I think writers are going to become bionic when they start using this. starting a business used to be such a painful process you needed to get a lawyer there were tons of fees it was a mess but not anymore just check out northwest registered agent they're going to help you form your company fast remember speed matters and then they're going to get you the docs you need to open a business bank account instantly then they're going to provide you with mail scanning and a business address and they're going to do all that keeping your personal privacy intact.

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11:07NorthwestRegisteredAgent.com slash twist. So you've recently become a venture capitalist, I understand. Congratulations. Since 1995. Since 1995, by the way. Well, I mean, I thought of you more as a company builder than a venture capitalist, but... I was both. I did the VC in my sort of spare time or in between jobs. But you are right. The last three years, first time I actually did a fund. Got it. With other people's, well, a lot of my money, but a lot of other people's money too. So why start a fund? And why do that here, you know, at this point in time? What stage you're trying to invest in?

11:43And what's the thesis of the fund? I do think that doing a startup, which I love doing, I did three of them. Let's say it's a young person's game. It takes 100-hour weeks. It takes a lot of focus. As you get older, you get more wise. And I think that's sort of... I've been doing venture for, like I said, since 1995. I've done really well at it. I love technology. So our thesis has really been on, if I had to sum it up, it would be SaaS slash AI companies with about a million dollars in revenue. So let's call it seed, sort of early A. And our specialties, we're all operators and we help these companies get to the next level, which would be sort of growth equity.

12:26So if they have a million in revenue, that's when you want to meet them or you want to put a million dollars into them? When they have a million in revenue. So we feel like the pre-seed is, I've always said ideas are cheap. There's a billion really bad ideas out there. For someone to actually get to that million-dollar level, that means they've proved product-market fit, which is a big risk. They've been able to track people, some capital. So they really de-risked it in our eyes. What they don't know is how do they take it to the next level. There's a lot of unanswered questions. A lot of this founder-led sales.

13:02A lot of it is how do I scale? How do I deploy capital efficiently? efficiently and so you know by by being operators having sort of sort of been in their shoes that's attractive to founders now they like it you know vcs a lot of vcs come from sort of the opposite extreme yeah i mean there's an argument for people who understand finance um and who haven't been in the trenches in some ways they can really have a good analysis um like bill girley of you know the marketplace dynamics they can be thoughtful about making the share price go up and then there's no substitute for people who actually have run a business right and been an operator and know exactly how hard that is and i think at our level by the way i think bill girley's always been one of my heroes i met him when he was a he was an analyst he was covering us double click back in the back in the uh the mid-90s what was he like tell me when you met him what it was like he was still he was very tall even back then still yeah he's consistently remained tall that is one thing i will say about bill girley's career you meet a lot of research analysts and most of them are good bill girley was just he was a new level he was he was the one guy that really really understood not just our business but he just he just had a great sort of macro view of what was going on and we always enjoyed conversations with with with bill where she wasn't retired is he retired i guess he's i guess that's a really interesting question because i he's theoretically not at benchmark well he's not at benchmark he's not in the new fund he's still on the boards he was on and he's still frisky and likes to hang out with founders and meet founders so i don't know that he's exactly retired and there was something about the venture community where they wanted to kind of set people out to pasture at a certain age maybe it's 60 years old etc and like hand over the firms to younger folks i think that was a key component of benchmarks philosophy is kind of forcing people out and letting young people take over but i think that for really great investors maybe sticking around would be pretty great for the founders and people live longer now and they're healthier and sharper in their 50s and 60s and 70s like no closer there he's like yeah you can basically drag me out of here i'm i'm not going anywhere but no closer yeah as active as ever so i i don't know what bill's deal is i think he should just do seed investments yeah two million dollar uh seed investments when you look at how being a founder has changed.

15:27When you and I were starting in the 90s, the idea of building an internet company was, well, you're going to have to spend a million bucks, a half million bucks on setting up your servers and hardware. You're going to need to put a half million dollars down on an office space and get a lease, put a letter of credit down. I mean, you were blowing a couple of million dollars just firing up a startup. Now, two or three people go to an accelerator, they get some free credits from Azure or whoever, and they're up and running and they build something on the weekend and get 10 customers. So it feels like many more startups are being built at a much lower pace.

16:00So how is that going to change things as we go forward here? And then it's quite possible AI makes things even faster for founders in terms of finding product market fit. I think you have two things going on. One is there was a long drought of entrepreneurs after the dot com crash, right? Everyone kind of fled to safety. And then things came back and I came back roaring with free money. And I think the venture market was oversaturated. There was just too much money. It was back in the dot-com days where people were just chasing any deal and any price. I actually think downturns like this are going to be good because there's just a lot of junk out there.

16:35And I'm amazed at what people are investing in. So I think raising money is much more difficult. Now, we've shifted, I think, more from growing at any cost, which I never understood. I think that's just where people... You take a large sum of money for a model that's not quite perfected, and you just lose more money. And I think those days are over, and it shouldn't be over. Just a bad way of doing business. But a year and a half ago, back to the age thing, one of the things you do get with age is, I have to do like four of these cycles. You know what's in the basement. You know when things go bad, they're way worse than you ever expected.

17:12You remember those days. Yeah. So getting people to cut back early and convincing them that, look, you got to conserve money. We got to trade off growth with burn. And that's okay. If you get through the cycle, it's better. I do think with the AI, the fact that any person can describe a business model at some point, not today, but can describe what they want to do and not go to expensive, often overpriced engineers to get it done. And like you said, it's all the groundwork is there, you know, putting up data centers. I don't know if you remember the data center. tyson you had one yeah and then you had the building on 32nd on the west side with the basketball court on the roof was that 32nd street or something remember it was west of them yeah 33rd 33rd west of uh madison square garden you had a basketball i remember we played hoops on the roof one time where we shot some hoops we did um double click you brought your team yeah you brought your stack west west fourth street yeah we had well you know we used to play at Chelsea Piers a bit and we had a pretty good team.

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19:21They love startups. Vanta.com slash twist. That's V-A-N-T-A.com slash twist to get a thousand dollars off your stock too. The key thing you did right talking about boom and bust cycles, you raised that secondary for double click. You also were able to sell some shares yourself and lock down a win. So explain how founders should ride the cycle. I am in agreement with you. the valuations I'm seeing on startups, because we do do pre-seed with our accelerator, and we do seed right around the point in time you're talking about, typically 500k, but 500 to a million is pretty close. And the same kind of thesis, right?

19:55You figured something out, you got some traction, you can't fake it, generally speaking. So this moment in time is the time to build. And there are some advantages to building in a down market. What are the advantages to building in a down market and then hey you know in another 5 10 15 years if it's a crazy up market what's the proper thing rational thing for founders to do in both markets compound question there uh i mean always like i tell ceos and everyone never your number one job is not run out of money so the three main reasons companies go to business the first one is they solve no known problem uh which i think gets back to the the the dot com as well as today where people are investing in cool technology let's say crypto or nfts exhibit you know our current examples they'd solve no known problem blockchain okay great another another ledger been around nothing new so a lot of money goes towards that so yeah i think people are focused more on you solve a problem the next reason they run they go out of business is they don't raise enough money and then the third reason is they raise too much money look at all the uh we were calling death of corns i don't know if that's a word we made up or that's a word give me that one up yeah death of corn sell okay death of corn so all these these companies that raised 100 million dollars last year they're going out of business it's like yeah what the hell kind of governance is that i i don't i don't understand yeah that's just not responsible so let's just as those are just bad you know again business doesn't change economics doesn't change and and we really push that on our on the founders you've got to build Business is really simple.

21:35You find a big problem, you solve it better than anyone else, and good things happen. People give you money. And if you do a really good job, they give you a lot of money, and then you get this thing called profit. And then once you get profitable, then you don't have to depend on anyone. But on the flip side, if you do get into a, as we tell founders, you get into the growth phase where you have a playbook, it's replicatable, and you have a high degree of conviction, then you got to use capital. A lot of people are like, well, I can borrow money. That's a lot harder these days. But the whole debt financing, debt financing of a tech company is just, I'm sorry.

22:11It's absurd. Get some debt as a sort of insurance policy. But if you got to use debt to grow an unprofitable business, you're screwed. Everyone's screwed. It was incredible. I guess in the Zerp environment, I had Series A companies that didn't really have product market fit. They were truly seed companies figuring out product market fit. but they were getting serious a evaluations and then yeah different banks were like well we have this money sitting here so we'll give you you raise 20 we'll give you 5 million you raise 30 we'll give you 10 million and then the founders just tack that on to their runway okay i have 18 months of runway i'll just you know i'm spending a million a month so i raise this 10 i raised 20 so i got 20 months and then i got 10 million in venture debt or seven that's seven more months and i say no you're not supposed to use it for that rainy day fund but don't use it as runway because then a VC has to look at your deal and say, okay, I'm paying down 7 million in debt.

23:04I'm putting another 20 million in and 7 million goes out the door to pay a bank. That doesn't make any sense. And in a down market with this globalization happening, how do you think about work moving around the planet? Because there's something unique that happened with remote work. You and I were in the in-office culture for two thirds of our career. And here we are, you know, a lot of people want to work from home. So do you believe in work from home or do you think people should be in offices? We'll start there. Yeah. I mean, I was talking to the, uh, uh, I'm going to forget his name now. He's at the Hoover institution, but he's, he's like the expert in, in sort of this whole work from home.

23:41And I was like, what, what's the answer? We just ended up a binary answer. There is no answer. I'm really torn. You know, I, I think for certain jobs and for certain types of people working at home is great. I think that it's really bad socially. And I think you get more done when you're in the office. Yeah. So for our work, I can do board meetings now with a five-minute notice. I'm in a board call as opposed to traveling for three days and wasting time. That's great. But most people aren't that disciplined. A lot of people are disciplined. They need mentorship. They need help. They need socialization.

24:14Yeah, there's a socialization part where people get weird working from home, staying at home all the time. They need mentorship. That's a lost part of this. And I'd say the top 20 % of performers are more effective at home. it's probably about another 30 that are equally effective in the bottom half are not nearly as effective as if they were in an office being mentored and part of the yeah i'm trying to reverse this at my companies and it's just incredibly hard because you have such a great talent pool of people at my venture firm with 22 people and then we can hire people faster than in silicon valley people don't want to be here anymore and it's too expensive to be here so i would get a lower quality person who wanted to be here versus this incredibly high quality person at a lower price will stay longer it's it's incredibly frustrating in some ways but it does seem to be reversing i'm curious i'm curious for you i mean you're you're a uh uh you're an opposite side of the spectrum as i am you're extroverted very extroverted yeah it's got to drive you crazy not to be it's socializing it's maddening and um i am now reversing it so i'm going to get like a space just so i could have like a co-working type space for my founders in my portfolio because I do need to be out and about.

25:25I host events. I do jam sessions. One of the things that I learned from Travis from Uber, he'd have these like jam sessions. Chris Sacco would do them too. We're just five or six founders. We get around, just hang out, have dinner, or just hang out at somebody's house and talk about their businesses for a couple of hours and try to help each other think through problems and strategies and blind spots. And so I'm sort of codifying that where I do these jam sessions every couple of weeks, bring together 20 founders. you know, go to our law firm, Wilson's and senior Femwix office, get a big conference room and just talk for four hours.

25:58And it's really, really energizing for me. And then doing the pod, you know, I get to talk to you and other, you know, investors, founders from around the world. And that does fill my bucket and give me that energy. But I think this has been great for introverts who, you know, they get to focus more and getting rid of commutes. If we didn't have the commute issue, I think this would be like people would be much more open to coming back to work here in the valley apple i think is four days a week now or four days a week in the year there might be three or four right now zuckerberg's kind of forcing people back and then roblox said either come back to the office or res you know resignation accepted um so i think they did it like a gentleman's riff basically you know we're going to reduce the force by the number of people who don't want to come back to the office so i think it'll start changing i also notice that people looking for work from home jobs are saying that they're having a hard time finding them.

26:49You know, as you get 1000, you know, 1000 applications, because anyone could be exactly that job, right? So now and then if you're a Silicon Valley person who wants to work from home, you've got the expensive Silicon Valley, but you want to work from home, you don't want to get on the bus, I understand it. But now you're competing against somebody in Portugal, argentina manila canada whatever it is and those folks are going to have a cost of living that's one-fifth one-tenth of the cost of living you have so they can accept a salary as much lower and all the management kevin have learned how to manage remote workers and that's actually the thing that is really mind-blowing to me once you learn how to manage a remote worker in south america canada portugal manila whatever it's no different it's all the same you're in a slack room you're on zoom you're doing huddles you're using notion or coda oh it's all the same so i think it also increases efficiency you could have somebody in the job in the role within two weeks whereas what would a job spec take getting somebody in new york you double click you paid people to move to new york you paid them to come out for an interview like think about those days a reload the concept of a thirty thousand dollar relocation package that was a thing right yeah danny siegel a guy I used to work with, he had a great observation when COVID first started hitting.

28:03He's called it the great reshuffling of America. And his theory was that people are going to move to somewhere where they wanted. But once that pendulum swing back, what you're going to see is that people in the office can promote it because they're there. It's FaceTime. People who are remote, you send them an email and they're gone. You have no personal relationship with them. So I think you're going to probably see a bit of a pendulum. I think a lot of it comes from the top down. You have executives who have second homes that don't want to go back. they want that we all thought commuting would be easier now that everyone works at home but turns out no one's actually working they're all driving driving around to go to go golf and do stuff we have plenty of examples in our companies that where people have multiple jobs um that's the crazy part they're not doing doing a job you know it's just it's we'll see i think it's going to swing back there's a reddit it's either overworked or overemployed and it's over employed over employed uh and if you read this reddit it is awesome because it's people trading strategies on how to fool their bosses and have two three or four simultaneous jobs there's a lot of times developers or you know marketers and they're like here's all the techniques to be on two conference calls at the same time but have the line of sight on your two laptops and i had this happen where somebody said hey um we got this great google um executive who wants to come work for us and that's great yeah he's willing to take a pay cut i'm like oh that's amazing right it's entrepreneurial so donnie wants to keep his job at google and they'll says he has 40 hours a week for us but he'll do it at like a third of his salary from google he said uh is that ethical well it's his problem not ours and i said is it because when google finds out and he's writing code for you during work hours do they own that code well there's a word for it yeah it's called Fraud.

29:52Fraud. Are you looking to build a SaaS product, but you need help on the technical side? Listen, developers, expensive. We all know this. And they're hard to find. But if you use DevSquad, they're going to help you validate your idea and bring that concept to market in three to six months. How do they do this? DevSquad is a fully managed agency that can handle product development end to end. This means you're not going to just get developers. You're going to get technical product managers, designers, and more, all for the price of just one US developer. This means you can focus on what you're good at, product strategy, sales, marketing, and they will do all the idea validation, the real user testing.

30:29And they are able to do this because there is amazing top talent in Latin America, an entire product team for the price of just one U.S. developer. Think about how much you're going to get done by leveraging DevSquad's amazing talent in Latin America. A technical product manager, that's your main point of contact, right? And then you're going to have product strategists, UX designers, DevOps, and quality assurance alongside that product manager, making sure that your product and your project is a success. So you pay month to month, no long-term contracts, no lock-in. Starts at just$40 an hour.

30:59And then they can scale depending on your needs. So I want you to visit devsquad.com slash twist. That's D-E-V-S-Q-U-A-D dot com slash twist to get more details and to get 10 % off your first month. In fact, Ivan Berkovich, one of our partners, just wrote an article on the over-employment problem. And we're getting a lot of pushback of people saying, well, that's just the employee-employee relationship is transactional now, so there's no meaning to it. So it's okay to commit fraud? What's the limiting factor here? You're stealing. The reason is you see this transaction because you're a negative, pessimistic person, and that it just becomes self-fulfilling prophecy.

31:36How can you possibly compete with a full-time employee and an equivalent full-time employee you can't yeah so you'll be the first one to go uh as they should be and they'll end up i used to say when you have two girlfriends you have zero girlfriends you know it's like it's when you have two jobs you'll end up with none yeah very very weird moment in time that yeah the the relationship between employers and employees is quite transactional and it this is one of the things that loss is loss is the culture right we the culture of companies really mattered people would stay with a company. And now switching is taking one laptop, putting it in a box, sending it back to your old company, opening up the new laptop, logging into a new Slack, logging into a new notion, Coda, Salesforce, whatever it is, HubSpot, and then just starting over.

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32:21And you do it in like the same day. There's no culture to, I guess, in some ways, that is efficient. But in other ways, something's lost. Yeah. Yeah. I mean, look at the tech market, that it's tech employment. Like you see these number of jobs filled every month going up. Those are people with part-time jobs. Everyone's trying to avoid the full-time. So they're taking another part-time service-oriented job. I mean, the tech industry is in a full-on recession right now, that depression. You know, I think a lot of people moved when the moving was hot. You know, that became very transactional. I'm going to take who's paying me the most.

32:56The best advice I had in college, the guy says, never take the job that pays you the most because there's a reason they have to pay you the most. It's like, because it's a crappy job. So find a company. Like, I don't think it should be transactional. I think it's easier when you're remote and you have no personal connection to the person. So, yeah. When you look at AI companies, there's this derogatory term, AI wrappers. Hey, they're just wrapping ChatGPT or Claude or, you know, whatever language model with some accoutrement, but they're going to be displaced by the primary model. OpenAI wins it all, destroys all competition.

33:30What's your take on that? So we have probably five AI companies now that were doing it before. My last company, we ended up being bought by Amazon and Alexa doing natural language processing. Large language models can answer some of those questions, but they can't answer all of them because you have to actually have the data. You have to have real-time data. A lot of the AI companies we're invested in now are using the large language models for classification purposes. They have their own models, but they're using it for the long tail. And it's quite good at that. But it doesn't build the application.

34:02So people are seeing it, again, as a technology to be used. And it's a very good technology, but it's not the app. I mean, it's not the total solution to the problem they're trying to solve. So one of the companies called Rogo, what they're doing is they're taking... Think of it as sort of an investor analyst, junior investor analyst. They're taking all the proprietary research from the investment bank, all the decks, all the thousands of decks they've done for clients, and they're adjusting all this private data. You forget, large language models are all public data. All the LLMs are going to look pretty similar.

34:37It's going to be that private stuff, the stuff that no one else has, that's going to be the differentiator, I think, in AI. Whether it's medical, legal, less so, because most legal stuff is public. I think legal is going to be dramatically changed. but again i don't think large language about i don't maybe they'll shift to that maybe they'll get a vertical component something that's more real time i don't know do you think the language models become commodified and you know it seems like open source models on hugging face are getting better and better and falcon out of the uae is you know available uh in an open source way and it just feels to me like all these language models are going to for 90 of tasks be good enough and they're going to be indistinguishable in the same way you know you open up any laptop and you fire up a browser it's all the same right the browser doesn't matter it's the content on the other side the service on the other time so it feels to me like it's all going to get commodified and you know like bandwidth it feels like bandwidth in some ways remember they built out all that bandwidth worldcom and everybody and then they overbuilt it they all went out of business and then people bought the bandwidth on pennies on the dollar it feels like that's what's going to happen to me i could be wrong i don't know no i think you're right i think it's going to be it's It's going to be very...

35:46Someone tried to get us to invest. They want to do an LLM. And they needed$100 million. I was like, are you kidding me? So it's going to be two or three players at the most. They're going to have the LLM. It's going to be like text-to-speech APIs or speech-to-text APIs. It's kind of magical in the beginning. And there just becomes a single API call or translation services or something. It's such a good analogy, Kevin, because I bought Dragon Dictate three times in my life. Just, you know, as a writer and a communicator, I was like, you know what, when my hands are tired, I just like to be able to talk into it.

36:20Spent hours training it when I was running the magazine and the blogging company. And it, you know, worked well for me. And then now you open up your iPhone. I don't know if you saw like the latest version. My Lord, when you hit the microphone key, it works flawlessly. And Apple's not good at this stuff. They tend to be like the worst at it. And the Apple's latest version of speech to text is better than any Dragon Dictator or anything I've used over the years. And it's free. is built into your phone. And so it does, I think it's a very good analogy. That's something that used to cost$5.99,$3.99 is just essentially free now.

36:54So if you remember, find the best turn to the graphic, we were building, unbeknownst to us, until Google talked about the knowledge graph. It turns out we were like, well, wait a second, we got a way bigger knowledge graph than Google does. And we were basically collecting all this sort of real-time information from everywhere from stocks to colleges to you name it, we had it. And trying to convince people, we were talking to Apple at the time and Amazon and Google. And Apple was about to buy us for Siri because Siri had a problem. It couldn't answer a lot of stuff. We always approached the problem as more like Jeopardy.

37:29You have to know the answer first and then figure it out the questions easy. Everyone in the AI area was focused on understanding the question. And it was an ass backwards way of approaching it. And we got in this big political issue apple was going to extend an offer for us and then they pulled it the last second and it was because their head of engineering at the time was convinced that ai would solve all problems and he ended up he ended up i don't know if he got fired or losing his job not that long after because ai does not solve all the problems especially at that time you have to have the answers find the best and you were organizing hey these are the best headphones these are the best laptops is the best ski mountains and by putting all of that into tables that's when you kind of had the aha moment of hey this semantic data is going to lead us somewhere no okay great we thought we could connect the two together and it would be it'd be interesting when we're trying to convince those companies that we had they could use our data to our their voice services they didn't believe it somebody uh it was actually iver berkovich and and dylan uh winslow did a hackathon and they ripped out alexa's brain and they put our brain into it it literally just took an afternoon uh to be able to tap into our knowledge graph and and uh they took a video of it and they sent it to to uh jeff bezos and i guess jeff sent an email with somebody saying who the hell are these guys why are they better than we are uh without anyone knowing about them so it really came down to the data understanding wasn't a problem that was trivial it was the mass in the data turned out to be a pain in the ass you have to you have to tap into i think we had something like 600 different databases data sets that we were pulling in from all over everything from help data to you know real-time bls data stock data how do you think about entrepreneurs today not to be curmudgeonly old men here but the traits that are timeless across the decades across the generations that you find lead to just incredible outcomes and the incredible founders who have incredible outcomes?

39:36What are the traits that you see? What I typically look for all employees, I call it SAGA, which is smart athlete, great attitude. So you can't teach IQ, so you got to be smart. You got to be competitive as hell. You got to hate losing. I love that question. Do you value winning more or do you hate losing? It's to hate losing. It's like you can't fail. I think it's just a great attitude. I think with entrepreneurs, I have this sort of test I give people to colleges and there's 10 questions and how they score. It whittles down to just a couple of people. And the final question is, are you delusional?

40:10Because no one's sort of like a perfect 10. But a lot of it is just this sense of urgency. It's not mañana. It's today. I got to get on this now. This is an opportunity. It's somebody who's willing to sort of look at data that has a high conviction in what they believe, but are also open enough to realize everything in life is a hypothesis. If the data shows you wrong, then you change it and be able to know that you can switch. I look for charisma. You know, charisma is a bit of a pejorative term, but charismatic people are, you know, they're visionaries. People believe in them. The best line I ever heard, the hardest thing about being a VC is figure out their founder is delusional or visionary.

40:52It's a very fine line. If they're right, they're visionary. If they're wrong, then they're probably delusional. I'm willing to bet on the delusional ones for sure. Because if you're delusional and you say, yeah, I think there's something out there and you leave Spain on a ship with some provisions, yeah, you got to be pretty delusional to think you're going to hit land because you might not. I like the delusional ones because if they hit land now they're visionary like you're saying well I'd say I'd put that in the visionary camera delusional are the ones that just refuse to listen they just they're just hell bent on I am right everyone else is wrong I don't care how much information is coming you know you're biased you know they just won't listen at all I see yeah that's a yeah I thought delusional as in like I could do something that nobody's ever done before but yeah i get your point if you define delusional as they're pig-headed and they will not change their mind in the face of new data you know that is what's wrong with american politics today you could have new information and people will just not change their position in the face of new information you look at what happened to science and coveted what happened to media would have the politicians the data was so obvious i'm having an argument right now with with a COVID health expert, how they completely screwed up our country based on it by just simply not looking at the data.

42:12The data was so obvious from day one, why they didn't listen to it. It just became so political. It became political. And then once you give advice, you can't say, well, you know what? Now, based on the statistics we have, hey, we're six months into this, we're nine months into this. If you're surfing at the beach and you're outside and you're healthy and you don't have comorbidities, you're going to get COVID at some point, but you're going to be fine. and if you're old and you've got comorbidities you really don't want to get this thing so stay home and limit your interactions uh and yeah if you get a cold make sure you come to the hospital so we can give you one of these drugs but yeah it was pretty crazy how nobody could think sensibly for two years well a lot of people could think sensibly but they were shot it down you know if you remember the great barrington declaration you know jay baccati of uh stanford i mean he was great he was he was just seen as ridiculed as you know crazy and pixie dust and you know he's completely right you know we all knew remember with omicron that's talking about covet yeah no it's okay they said they said uh oh the vaccine will stop you from getting getting covet and we all had omicron like everyone we do had like literally it happened to me three weeks after i got the vaccine i got the vaccine i went to sax's christmas party his super spreader uh spectacular as i called it i got omicron and uh i didn't know i had it my wife said i heard i sneezed twice we were skiing and she said you you got covid and i said i don't feel anything i went to bed i had a little bit of hot sweats i went skiing two days later i felt fine i tested positive for covid for 19 days i felt it was the meekest cold for 12 hours i've had in my life probably oh i i'd rather have i'd rather have covid than a cold we were in we were in the caribbean we couldn't couldn't get back to the country because we kept testing positive and the worst thing that happened the nurse made so much money yeah just every day three hundred dollar test three hundred dollar test trying to give back to the states i mean it really is like i'm now moved to the point where i'm very resentful of i don't resent the first year because i think people were trying to do the right thing and it was unprecedented it was spreading but i'm really resentful of like year two and how they position the vaccine like it's absolutely you have to take it because you're going to become a blocker and i was like you know what that makes sense to me if i don't spread it i'm a blocker great we go to a party there's eight blockers there's two people could spread it hey chances of spreading get go way down and even that wasn't true yeah look we got it we ended up traveling all over the world by the way it's the best time ever to travel every place we went there was no lines we went to airports where there'd be no people it was great we were when i looked at the data i'm going okay not old not morbidly obese no comorbidities my probability of dying is zero yeah like it's not gonna happen so we just went all over it was fun but you know i convinced my kids to get it just because they were uh in their 20s i was like you don't need it like there's no way you need it but your life is going to be painful like you won't be able to do it you won't be able to travel yeah the whole thing all right no more about covid yeah no i mean there's some lessons there too from like uh the censoring on youtube and stuff like that is very interesting having a podcast and then having your podcast flagged and i'm like but we're having an intellectual discussion about this you don't need to flag my podcast it's just like oh my god we have to you here's what you have to believe and i'm like really i have to believe that and i have to put this warning on your content i'm like on this week in startups really okay so i wrote an editorial the wall street Journal defending big tech probably about three years ago.

45:48And my argument is like, it's very libertarian argument. You don't want to go to their site, don't go to their site. It's their property. They can do whatever they want. I didn't realize that the government was actually interfering, you know, basically doing censorship, using them on their behalf. To me, I was like, I want to retract that editorial. It was unbelievable that they were doing censorship and i think that's why people have have lost trust lost trust in so many many of our institutions i think what elon must you know for freedom of speech you know he's he can be a bit crazy often uh but you know you got to love the freedom of speech there's downsides to it yeah i mean it was it is a very hard thing to champion freedom of speech because that means you have to champion some things that are pretty gnarly and you have to tolerate some things that maybe are ugly and that you don't agree with uh but our generation i think that was like a core tenant and it's just very weird to watch generations feel like they're going to be like absolutely disturbed because somebody said something they don't agree with it's bizarre they need you don't need to be protected from words like they're just words like we're in the dictionary yeah it's weak very weak like there are true there are no trigger warnings in life you know bad bad stuff happens to very suddenly.

47:06That's the thing I look for in entrepreneurs. We're back to the entrepreneurial question is some amount of resiliency and some core beliefs that you believe in that, you know, you're not going to just be shaken from like, if you believe that this thing should exist in the world, and you're resilient, and you're going to fight the fight for that thing. And you have that belief in the thing. Now, of course, you have to have some amount of smarts and some amount of, you know, hatred of losing, and you'll get there. But man, I do like principled people. And then, you know, they can be hard to get along with, but the world absolutely needs them.

47:36What do you think about valuations now? Just to go on to another tangent, you know, things have gotten crushed in the public market starting to come back, we had a pretty good year here, it feels like things are stable. But private market comps, public market comps is pretty gnarly for SaaS, and you've chosen SaaS. Where do you think this all winds up? You said you wanted to invest in companies with a million dollars in ARR, let's say, what should they be valued at today? And what will they ultimately be valued at? So we invest in companies outside Silicon Valley, primarily for that reason. I just don't...

48:05We're down in Santa Barbara. If a company comes to us, they could throw a rock and kill 10 VCs. Why are they coming to us? Why would they take money? Clearly, most... Huge percentage of great companies come out of Silicon Valley, but it's also even a greater percentage of money is in Silicon Valley. So the competition is extremely, extremely fierce. I look at some of the valuations where people have given like 250 times revenue. I just, I don't get it. I don't know how you grow into it. Maybe I'm, maybe I'm missing something, but you know, we tend to look at, you know, obviously growth rate, retention, churn.

48:40We just, and then we do, you know, we think is a reasonable number based on growth rate. You know, it's above, you know, most public, no public company growing at 200%, 300 % anymore, but we just don't go crazy with valuations and maybe we lose some deals. yeah that's it was that's part of ventures you lose deals and those deals some of those deals go go off and do great things and founders have kind of figured it out too they know how to in today's day and age back in our day it just wasn't a lot of information or insights into how the whole system worked even understand how a convertible note worked or how rounds were priced it was all kind of in a black box you had to really go discover that information now it's all out there and how to run a process is all out there so founders know how to run a process and get the valuation they want if they're trying to optimize for valuation but i'm not sure optimizing for valuation is a great idea um like you said before about optimizing for your salary is not a great idea well i have a lot of sort of canned speeches i give to to to entrepreneurs um you know i think some of the biggest mistake you mistakes you'll see like on these death of corns they've piled on so much preferred, they'll never see a penny.

49:52They could build a great company, a$100 million company, not bad. I'd take one of those and they'll receive nothing. So taking out too much money is just as bad as not having enough money. It causes bad habits. We can usually get around the valuation. I mean, it's a tough market to raise money in. If you've got a great company, it's pretty easy. you know there's a lot of vc funds that are not able to to raise raise another fund there's gonna be i'd say 50 of vc funds will be gone you know within a year i'm raising my current fund and we're halfway to our target we hit our first target and now we're going for the stretch goal and it has been 10 times as much work as when i raised the the previous uh funds and a lot of the other fund managers i'm talking to have given up they're just out of the market and you're starting to see the layoffs happen quietly at venture firms you wouldn't see it because people stay as you know they're partners but they're not getting paid anymore they're getting a small draw whatever they're kind of winding down i would call them zombie funds and then they're maybe hoping next year they can go raise a fund or the year after but for those of us who have money to deploy this feels like the greatest time ever because you get to see a lot of companies people are running their companies in an intelligent fashion and they're focused on what matters product market fit customers revenue so it feels to me like this is the best possible time to be an investor i mean that's always irony right when when the market our fund was a 2021 vintage and um it's doing great yeah yeah on a relative basis but you know when valuations are high people will only give you money when they're when they're low you know they're at once and what's nervous we're about halfway through our our fundraise as well i've never understood why one of the models i think that's broken adventure i don't know what your gp commit is but you know most of these VCs, there's not a big GP commit.

51:41No. Well, why not? Why not? Yeah. To me, it's the best place. Best place I can put my money. I'll have a couple of million dollars into my fund. Yeah. So it's, yeah, it's not, I've got a lot of skin in the game. And if you believe in yourself, yeah, there, I think there were a lot of folks who were putting in like well below 1 % of their fund, like the entire partnership, five people might be like 1 % of the fund. And it's like, really? You have a quarter million dollars in your fund? Wow. That's incredibly risk-taking of you. Yeah. How much does your second home cost? I think I'll be like 20.

52:18The first one, it was probably about 30%. Yeah. 20%, 30%. I don't take salary because I want to use it to invest in other people. I mean, I don't have any income. I'd rather have capital gains, Kerry. Yeah. Kerry's the way to go. Absolutely. Are you have you moved to the institution raising money from institutions yet? Yeah, we're just starting that process. So I've meeting with sovereign wealth funds, family offices, you know, like larger family offices. So I guess those aren't institutions fund to funds. But yeah, you know, we're not going to add$100 million fund size ever be a fit for CalPERS or Harvard, you really need to get to like, you need to put in$50 million checks is my understanding.

53:00And yeah, they're reducing the number. so those institutions are pretty hard i think family offices fund to funds to the extent they exist and sovereigns are you know the the likely route for any sub 500 million dollar fund we haven't done we're about trying to raise about roughly the same we just started first time going to going to more fund to funds institutions we haven't done sovereign haven't done anything offshore yeah are you having any success there or yeah i think it well not yet but i've been meeting a ton of people and i think that they are very interested in having a seat at the table and the people who have a seat at the table are on pause so then you have this interesting market dynamic okay the people who in the u.s are over committed they have the denominator problem stock market came down their venture portfolios didn't get marked down so they went from 10 allocation and venture to 25 they haven't liquidated their tiktok or their stripe or other companies that need to go public and so they need to get their venture commit down to 10 % again or 15 % from 20 or 25.

54:01And that's going to take equities going back up or returns coming in and clearing some of that venture position. So I think they're largely on pause for 22, 23, and 24. So if you're Harvard, if you're Yale, if you're Stanford, it's just going to be a big, long pause while you... And then you've already committed to great firms. So there's no rush here, right? They're thinking in decades. So for fund managers who need to raise during these two or three years it's going to be very hard it's going to be very hard and i have a track record so i think i'm you know in a good position but i would say it takes 10 times as many meetings to raise half as much yeah the first one was a bunch of emails say doing a fun you interested boom yes that's okay we're finding there's like the smaller funded funds or the smaller smaller institutions that they don't have it much venture exposure so but you are right the larger ones yeah massive checks as people are saying pencils down right now yeah people are pencils down right now and that's okay um it'll come back and as long as you have some money to invest you and i have our own money so you keep investing and you're going to get the pick of the litter right now it's not like deals are taking you know five days two weeks to close they're taking two months six months to close a deal so on the on the buy side when you're investing you have plenty of time to get to know a founder again and due diligence which is good for everybody it's great for the ecosystem all right I got to jump.

55:23Kevin O 'Connor, great to spend time with you and let's catch up next time you're in the Bay Area.

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Today’s show:

ScOp’s Kevin O’Connor joins Jason (1:39), exploring the early days of the internet, its initial promise, rapid growth, and the recent pivotal changes brought on by AI (1:39). They also discuss tactics for building in a declining market, the emergence of “death-icorns” (19:30), what he looks for in founders (39:18), and much more!

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Timestamps:

(0:00) Jason welcomes Kevin O’Connor of ScOp Venture Capital.

(1:39) Exploring the early days of the internet, its initial promise, rapid growth, and the recent pivotal changes brought by AI.

(5:55) Discussing the impact and future prospects of AI as we approach 2024.

(8:41) Delving into the potential influence of AI on sectors like Hollywood and the music industry.

(10:03) Northwest Registered Agent - Get a 60% discount on your next LLC at http://www.northwestregisteredagent.com/twist

(11:11) Transitioning from founding companies to establishing a fund and supporting new startups.

(15:25) Examining the evolution of founding a company, market dynamics, and fluctuating trends since the 1990s.

(18:22) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(19:30) Tactics for building in a declining market, the emergence of “death-icorns,” and the pitfalls of debt-financed growth in unprofitable businesses.

(27:57) The pendulum swings back after “the great reshuffling of America” and the phenomenon of over-employment.

(29:53) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at http://devsquad.com/twist

(33:13) Identifying unique opportunities in AI investments.

(36:50) Recounting a near acquisition of Kevin’s company Graphiq by Apple for Siri integration.

(39:18) What Kevin currently seeks in entrepreneurs before making an investment.

(47:35) Discussing current valuation trends and the competitive nature of losing deals in venture capital.

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LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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