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Investing 101 Conversations

Contrary Research Radio

As part of Contrary Research, I host a podcast digging into the stories of the most interesting private tech companies and industries.

Podcast Appearances

“90% of VCs Are Neutral to Negative Value”: Kyle Harrison on the Evolving Game of Venture Capital

The venture capital landscape is evolving, and a founder’s choice of fund size and partner could make or break their business. In this episode, CJ sits down with Kyle Harrison, General Partner at Contrary and writer of the Substack Investing 101, to make sense of the changing incentives and power dynamics in the field of venture capital. He explains how capital agglomerators and cottage keepers are playing dramatically different games, how the ethics of backing competitors have changed since the advent of AI, why a fund's size is its strategy, and what the potential pitfalls of dilution could be for founders. The conversation also covers why the line between hype and tangible business value in AI is so blurry, the role of narrative as an economic driver, and why the most valuable thing a VC can offer might just be "borrowed credibility.” — LINKS: Kyle Harrison on LinkedIn: https://www.linkedin.com/in/kyle-harrison-9274b278/ Contrary: https://www.contrary.com Investing 101: https://investing101.substack.com CJ on X (@cjgustafson222): https://x.com/cjgustafson222 Mostly metrics: https://www.mostlymetrics.com LINKS MENTIONED: “The Unholy Trinity of Venture Capital”: https://investing101.substack.com/p/the-unholy-trinity-of-venture-capital “The Horse, The Jockey, or The Whole Race?” https://investing101.substack.com/p/the-horse-the-jockey-or-the-whole Endowment Eddie on X (@endowment_eddie): https://x.com/endowment_eddie “Institutionalized Belief In The Greater Fool”: https://investing101.substack.com/p/institutionalized-belief-in-the-greater “The Unbundling of Venture Capital”: https://investing101.substack.com/p/the-unbundling-of-venture-capital “The Productization of Venture Capital”: https://kwharrison13.com/essays/the-productization-of-venture-capital — TIMESTAMPS: (00:00) Preview and Intro (02:25) Sponsor – Navan | Rillet | Pulley (07:16) VC Models: Cottage Keepers Versus Capital Agglomerators (11:24) Balancing Taking On Money and Finding Great Investments (16:46) Sponsor – Brex | Aleph | RightRev (21:06) Founder-Friendliness: The Ethics of Backing Competitors (26:49) When Fund Size Sabotages Outcomes (32:50) The Sins of Omission Versus Commission (36:26) The Dilution Trap for Operators in Venture-Backed Companies (38:48) Underestimating the Magnitude of the Outcomes (41:09) AI Hype, Valuation, and Real Business Impact (46:18) Market Psychology: Narrative and Story As Economic Drivers (49:07) Valuation: Cursor and Windsurf (53:40) The Unbundling of Venture Capital: What Founders Really Hire VCs For (1:02:43) Things To Consider When Choosing a VC (1:05:33) FTX Lessons & Compounding Growth (1:11:12) Kyle’s Predictions for the Future of VC — SPONSORS: Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti. Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics. Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics. Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo. Mark Andreessen Photo credit: JD Lasica, CC BY 2.0 https://creativecommons.org/licenses/by/2.0, via Wikimedia Commons Vinod Khosla Photo credit By Jay Dixit - Own work, CC BY 4.0, https://commons.wikimedia.org/w/index.php?curid=146472964 ##VentureCapital #VC #Startups #Founder #FundSize

“90% of VCs Are Neutral to Negative Value”: Kyle Harrison on the Evolving Game of Venture Capital
Kyle Harrison, GP at Contrary on Techno-Optimism, Talent Vortexes, & Writing “Investing 101”

In this episode, Molly O'Shea interviews Kyle Harrison, General Partner at Contrary and writer of the popular Investing 101 substack, discusses his career in venture capital and the focus of Contrary. Contrary is a VC fund that backs companies from seed to scale with an emphasis on talent and research. They aim to identify the smartest people early on and support them throughout their careers. Contrary has a very impressive research arm that produces reports, memos, and conversations to provide insights into private tech companies. Kyle shares his approach to writing and the importance of putting his thoughts into words. The conversation explores the themes of hard work, ambition, and the divide between different work philosophies. It also touches on the power of storytelling and the influence of narratives on shaping reality. The discussion highlights the importance of nuance and individual beliefs, as well as the cycles of hype and deflation in the tech industry. Overall, the conversation provides insights into the dynamics of the startup ecosystem and the evolving perspectives on work and success. Follow us on Twitter https://twitter.com/MollySOShea https://twitter.com/kwharrison13 -- Resources * https://www.linkedin.com/in/kyle-harrison-9274b278/ * Investing 101: https://investing1012dot0.substack.com/ Popular Investing 101 Pieces * The Blackstone of Innovation: https://investing1012dot0.substack.com/p/the-blackstone-of-innovation * Institutionalized Belief in The Greater Fool: https://investing1012dot0.substack.com/p/institutionalized-belief-in-the-greater * Puritans of Venture Capital: https://investing1012dot0.substack.com/p/the-puritans-of-venture-capital * Historical Futurism: https://investing1012dot0.substack.com/p/historical-futurism * Renaissance of Rise & Grind: https://investing1012dot0.substack.com/p/the-renaissance-of-rise-and-grind Check out * Contrary: https://www.contrary.com/ * Contrary Research: https://research.contrary.com/ Trending Reports: * SpaceX: https://research.contrary.com/company/spacex * Notion: https://research.contrary.com/reports/notion * SHEIN: https://research.contrary.com/company/shein * Midjourney: https://research.contrary.com/company/midjourney * Ramp: https://research.contrary.com/company/ramp * Anduril: https://research.contrary.com/company/anduril Deep Dive: * The Openness of AI: https://research.contrary.com/reports/the-openness-of-AI * The Great Bank Unbundling: https://research.contrary.com/reports/great-bank-unbundling Foundations & Frontiers by Anna-Sofia Lesiv (https://twitter.com/annasofialesiv): https://www.contrary.com/foundations-and-frontiers * The Decentralized Future of Nuclear Power: https://www.contrary.com/foundations-and-frontiers/nuclear-power * The Rise of Robots: https://www.contrary.com/foundations-and-frontiers/robotics * The Evolution of Chips: https://www.contrary.com/foundations-and-frontiers/evolution-of-chips * The Mars Colonization Tech Stack: https://www.contrary.com/foundations-and-frontiers/mars-colonization * The Future of Aviation: https://www.contrary.com/foundations-and-frontiers/aviation * Building Brain-Computer Interfaces: https://www.contrary.com/foundations-and-frontiers/brain-computer-interfaces * Subscribe to Sourcery: https://www.sourcery.vc/ Companies Mentioned * Lyft: https://www.lyft.com/ * TVC: https://www.tcv.com/ - TIMESTAMPS: (00:00) Preview and Intro (00:56) Kyle Harrison: A Journey from Filmmaker to Venture Capitalist (06:16) The Evolution and Strategy of Contrary VC (09:35) Open Source Research in Venture Capital (15:37) Finding And Helping The Greatest People On The Planet (17:47) Investing 101: The Art of Writing and Reflection (21:00) Reflecting on Personal Writing: Hits and Misses (23:17) Exploring the Impact of Social Media and Work Culture (23:57) The Philosophical Divide in Work Ethic and Ambition (27:30) Techno Optimism and the Power of Positive Narratives (28:52) Reflections on Storytelling and Reality (34:20) The Influence of Location on Perspective and Innovation (39:07) Looking Forward: The Age of Acquisition and Hype Cycles (45:56) Wrap

Kyle Harrison, GP at Contrary on Techno-Optimism, Talent Vortexes, & Writing “Investing 101”
The Centralization of Power in AI // Kyle Harrison // MLOps Podcast # 181

MLOps podcast #180 with Kyle Harrison, General Partner at Contrary, The Centralization of Power in AI. // Abstract Kyle Harrison delves into the limitations imposed by language, underscoring how it can impede our grasp and manipulation of reality while stressing the critical need for improved language model performance for real-time applications. He further explores the perils of centralizing power in AI, with a specific focus on the "Openness of AI", where concerns about privacy are brought to the forefront, prompting his call for businesses to reconsider their reliance on it. The discussion also traverses the evolving landscape of AI, drawing comparisons between prominent machine learning frameworks such as TensorFlow and PyTorch. Notably, the episode underscores the vital role of open-source initiatives within the AI community and highlights the unexpected involvement of Meta in driving open-source development. // Bio Kyle Harrison is a General Partner at Contrary, where he leads Series A and growth-stage investing. He joined Contrary from Index where he was a Partner, and before that he was a growth investor at Coatue. His portfolio includes iconic startups and public companies including Ramp, Replit, Cohere, Snowflake, and Databricks. He also regularly shares his analysis on the venture capital landscape via his Substack Investing 101. // MLOps Jobs board https://mlops.pallet.xyz/jobs // MLOps Swag/Merch https://mlops-community.myshopify.com/ // Related Links Website: https://investing1012dot0.substack.com/ The Openness of AI report: https://research.contrary.com/reports/the-openness-of-ai ⁠ --------------- ✌️Connect With Us ✌️ ------------- Join our slack community: https://go.mlops.community/slack Follow us on Twitter: @mlopscommunity Sign up for the next meetup: https://go.mlops.community/register Catch all episodes, blogs, newsletters, and more: https://mlops.community/ Connect with Demetrios on LinkedIn: https://www.linkedin.com/in/dpbrinkm/ Connect with Kyle on LinkedIn: https://www.linkedin.com/in/kyle-harrison-9274b278/ Timestamps: [00:00] Kyle's preferred beverage [00:20] Takeaways [03:52] Hype in technology space [09:20] Application Layer Revenue [14:44] Stability AI Lawsuit [18:08] Concern over concentration of power in AI [20:20] Transparency concerns [23:35] Open Source AI [25:57] To use or not to use Open AI [30:51] Lack of technical expertise and business-building capabilities [35:09] AI Transparency and Accountability [37:50] Traditional ML [41:47] Finding a unique approach [45:41] AGI limitations [47:43] Using Agents [49:46] Agents getting past demos [54:39] Tech Challenges & Hoverboard Dreams [58:04] Both AI hype and skepticism are foolish [01:27] Wrap up

The Centralization of Power in AI // Kyle Harrison // MLOps Podcast # 181

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