Kevin O'Connor on backing visionaries, the future of VC, internet history and more | E1861
This Week in Startups
Jason Calacanis
4.2 • 1.4K Ratings
🗓️ 8 December 2023
⏱️ 56 minutes
🧾️ Download transcript
Summary
This Week in Startups is brought to you by…
Northwest Registered Agent. When starting your business, it's important to use a service that will actually help you. Northwest Registered Agent is that service. They'll form your company fast, give you the documents you need to open a business bank account, and even provide you with mail scanning and a business address to keep your personal privacy intact. Visit http://www.northwestregisteredagent.com/twist to get a 60% discount on your next LLC.
Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at https://www.vanta.com/twist
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 http://www.devsquad.com/twist
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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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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
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Check out ScOp Venture Capital: https://www.scopvc.com
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Follow Kevin:
X: https://twitter.com/kjpoconnor
LinkedIn: https://www.linkedin.com/in/kevinoconnorsb
Follow Jason:
Instagram: https://www.instagram.com/jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
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Thanks to our partners:
(10:03) Northwest Registered Agent - Get a 60% discount on your next LLC at http://www.northwestregisteredagent.com/twist
(18:22) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
(29:53) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at http://www.devsquad.com/twist
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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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Check out Jason’s suite of newsletters: https://substack.com/@calacanis
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Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
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Subscribe to the Founder University Podcast: https://www.founder.university/podcast
Transcript
Click on a timestamp to play from that location
| 0:00.0 | The best line I ever heard, the hardest thing about being a VC is |
| 0:03.2 | Figueginal or visionary. It's a very fine line. |
| 0:07.2 | If they're right, they're a visionary, if they're wrong, then they're |
| 0:09.8 | probably delusional. |
| 0:10.8 | I'm willing to bet on the delusional ones for sure, because if you're delusional. I'm willing to bet on 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 going to hit land, |
| 0:22.8 | because you might not. |
| 0:24.4 | I like the delusional ones, because if they hit land, |
| 0:27.3 | now they're visionary, like you're saying. |
| 0:29.1 | Well, I'd say, I'd put that in the visionary, yeah, right? |
| 0:31.3 | Delusional are the ones that just refuse to listen. |
| 0:34.7 | This week in startups is brought to you by Northwest registered agent. |
| 0:39.4 | When starting your business, it's important to use a service that will actually help you. |
| 0:44.0 | Northwest registered agent is that service. |
| 0:47.0 | They'll form your company fast, give you the documents you need to open a business bank account, |
| 0:52.0 | and even provide you with mail scanning and a business address to keep your personal privacy intact. |
| 0:58.0 | Visit northwest registered agent.com slash Twist to get a 60% discount on your next LLC. |
| 1:06.0 | Vanta compliance and security shouldn't be a dealbreaker for startups to win new business. |
| 1:11.0 | Vanta makes it easy for companies to get a sock too report fast. |
| 1:15.9 | Twist listeners can get $1,000 off for a limited time at vanta.com slash twist and dev squad most dev agencies only offer developers why because |
| 1:28.4 | product management is hard get an entire product team for the cost of one U.S. developer plus 10% off at Dev Squad.com slash |
| 1:38.3 | Twist. All right everybody welcome back to the program. Our guest today is Kevin O'Connor. I met him 28 years ago in |
| 1:46.5 | 1995. I was running a little magazine called Silicon Alley reporter and Kevin had just |
... |
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