Investing 101 Conversations
Speculative Obsession (with Michael Dempsey)
Venture as a Thesis Delivery Mechanism https://investing101.substack.com/p/speculative-obsession-with-michael
www.youtube.com
A Return To Artisanal Venture (with Rex Woodbury)
Building a Venture Firm With Authenticity https://investing101.substack.com/p/a-return-to-artisanal-venture-with
www.youtube.com
The 7 Deadly Sins of Venture Capital (with Dan Gray)
Mapping The Systemic Flaws in the Venture Ecosystem https://investing101.substack.com/p/the-7-deadly-sins-of-venture-capital
www.youtube.com
When History Rhymes (with Beezer Clarkson)
The Wisdom of Cycles & The Importance of Thinking For Yourself https://investing101.substack.com/p/when-history-rhymes-with-beezer-clarkson
www.youtube.com
The Loudest Models (with Trace Cohen)
https://investing101.substack.com/p/the-loudest-models-with-trace-cohen
www.youtube.com
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.
Contrary Research Radio on Apple Podcasts
Business · 2023
podcasts.apple.com
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
www.youtube.com
Intel, chips and America’s future
Podcast Episode · Riskgaming · 08/13/2025 · 49m
podcasts.apple.com
TBPN | Tuesday, August 5th
TBPN.com is made possible by: Ramp - https://ramp.com Figma - https://figma.com Vanta - https://vanta.com Linear - https://linear.app Eight Sleep - https://eightsleep.com/tbpn Wander - https://wander.com/tbpn Public - https://public.com AdQuick - https://adquick.com Bezel - https://getbezel.com Numeral - https://www.numeralhq.com Polymarket - https://polymarket.com Attio - https://attio.com/tbpn Fin - https://fin.ai/tbpn Graphite - https://graphite.dev Restream - https://restream.io Follow TBPN: https://TBPN.com https://x.com/tbpn https://open.spotify.com/show/2L6WMqY3GUPCGBD0dX6p00?si=674252d53acf4231 https://podcasts.apple.com/us/podcast/technology-brothers/id1772360235 https://www.youtube.com/@TBPNLive
youtu.be
AGI, Seriously + Foundation Model Polyamory (With Kyle Harrison)
This week, Tom breaks down his scoops on how the big foundation model providers are doing.and much to the chagrin of our resident skeptic, they’re earning lots of real revenue! OpenAI is on track to crack over $12 billion in revenue this year, and Anthropic projects it will double its ARR to $4 billion by the end of the year. But have we hit the AGI moment? Eric relays his o3 experiments as evidence. Madeline gets into the perpetual VC optimism in spite of market turmoil and why AI has early stage investors mostly unphased. In the second half of our show, Eric interviews Contrary’s Kyle Harrison about his viral foundation model market map and why AI has led many VCs to embrace startup polyamory.
www.youtube.com
Kyle Harrison: Contrary GP on Talent & Research-Driven Investing
Kyle Harrison is a General Partner at Contrary. Contrary is a talent and research-driven investment firm. We back a small number of exceptional people and the companies they build, from seed to scale. He is an investor in Ramp, Replit, Anduril, OneSchema, Zepto, Moment, Nomic, Pave, Patch, Modern Intelligence, Teamshares, Leland, Synthesis, Armada, Power, and more. Prior to Contrary he is a Partner at Index Ventures and Growth Investor at Coatue Management and TCV. Topics: - Supporting Founders from Seed to Scale - The Role of Research in Venture Capital - The Importance of Storytelling in Investing #VentureCapital #StartupInvesting #TechTrends #Entrepreneurship #InvestmentStrategy
www.youtube.com
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
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Down Round: Capital Inferno Heaven (feat. Kyle Harrison) on Apple Podcasts
Show Down Round, Ep Capital Inferno Heaven (feat. Kyle Harrison) - Apr 9, 2024
podcasts.apple.com
#17 - Kyle Harrison on Venture Capital, Mormonism, and Driving Your Own Life
Listen to this episode from The Idea Exchange on Spotify. Kyle Harrison is a General Partner at Contrary Capital, a San Francisco-based Venture firm, and is the author of "The Investing 101 2.0" newsletter.Kyle's Socials:Twitter: https://twitter.com/kwharrison13Personal Site: https://kwharrison13.com/Substack: https://investing1012dot0.substack.com/Contrary's Website: https://contrary.com/
open.spotify.com
Venture Capital: Kyle Harrison
#venturecapital #investing In this week's podcast, we speak with Kyle Harrison, GP at Contrary and long time venture capitalist. We go through how he spends his day - how to find companies, how to determine which ones will skyrocket in the next 10 years, and what the biggest misconceptions are about his industry. Visit colbyhoward.com for more!
youtu.be
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
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Audience of One: #037 - Kyle Harrison on Investing in People, Talent Vortexes, Writing, & Tradition vs Progress on Apple Podcasts
Show Audience of One, Ep #037 - Kyle Harrison on Investing in People, Talent Vortexes, Writing, & Tradition vs Progress - Oct 4, 2023
podcasts.apple.com
Redefining AI - Artificial Intelligence with Squirro: Kyle Harrison - Navigating the AI Investment Landscape on Apple Podcasts
Show Redefining AI - Artificial Intelligence with Squirro, Ep Kyle Harrison - Navigating the AI Investment Landscape - Sep 5, 2023
podcasts.apple.com
Category Visionaries: Funding the Future: Kyle Harisson, General Partner at Contrary on Apple Podcasts
Show Category Visionaries, Ep Funding the Future: Kyle Harisson, General Partner at Contrary - Aug 23, 2023
podcasts.apple.com
The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified: 386. Finding Product Market Fit As a Venture Firm, How to Identify World-Class Founders Before Anyone Else, And Debating Whether or Not Venture Has Hit The Bottom (Kyle Harrison and Eric Tarczynski) on Apple Podcasts
Show The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified, Ep 386. Finding Product Market Fit As a Venture Firm, How to Identify World-Class Founders Before Anyone Else, And Debating Whether or Not Venture Has Hit The Bottom (Kyle Harrison and Eric Tarczynski) - 5 Jun 2023
podcasts.apple.com
VC Contagion: Is Venture Capital Killing Itself? | The Newcomer Podcast
For this week’s Newcomer podcast, I talked with Contrary general partner Kyle Harrison. We spent the first part of the episode talking about his piece VC Contagion: Is Venture Capital Killing Itself? I just published the essay exclusively in Newcomer. Then, on the podcast Harrison talked about Contrary and its research strategy. The firm has published reports on Stripe, OpenAI, Databricks, and many other private companies. We also discuss whether, when it comes to the private markets, information really wants to be free. Harrison talks about the gossip economy that powers the venture capital industry.
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The Generation Hustle Podcast: GHP #96 - VC #18 - Backing Bold Founders from Seed to Scale with Kyle Harrison! on Apple Podcasts
Show The Generation Hustle Podcast, Ep GHP #96 - VC #18 - Backing Bold Founders from Seed to Scale with Kyle Harrison! - Feb 28, 2023
podcasts.apple.com
Sand Hill Road on Apple Podcasts
A place to talk about startups, venture capital and tech. For a full download, double-click on sandhillroad.io A place to talk about startups, venture capital and tech. For a full download, double-click on sandhillroad.io Sand Hill Road has quickly become a favorite in my feed! Erasmus is a fantastic host.
podcasts.apple.com
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch: 20VC: Why 75% of Active Investors Will Disappear in the Next Few Years, The Death of "So So" Venture Firms is Coming, The Rise of Blackstone of Venture Firms and What That Does To Venture Returns, How the World of LPs is Broken and more with Kyle Harris on Apple Podcasts
Show The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch, Ep 20VC: Why 75% of Active Investors Will Disappear in the Next Few Years, The Death of "So So" Venture Firms is Coming, The Rise of Blackstone of Venture Firms and What That Does To Venture Returns, How the World of LPs is Broken and more with Kyle Harris - Oct 21, 2022
podcasts.apple.com
Unlimited Partners: Kyle Harrison, GP at Contrary | Cinematographer Turned Investor, Time as a Resource, Ramp, Pave and Investing in Talent on Apple Podcasts
Today's Unlimited Partner is Kyle Harrison, General Partner at Contrary, a venture fund that "identifies and invests in the world's top talent. Backed by iconic founders from Tesla, Airbnb, Facebook, and more" in early stage rounds. Kyle joined to lead their Breakout Fund. He's also a writer with hi...
podcasts.apple.com
Through the Noise: E17: Kyle Harrison - Backing the Bold on Apple Podcasts
Kyle Harrison is a General Partner at Contrary, a venture firm backing some of the boldest entrepreneurs of our time. Since inception in 2018, their portfolio includes the likes of Anduril, DoorDash, Ramp and Synthesis. Kyle joined Contrary in May this year to Co-Found Contrary's later-stage practic...
podcasts.apple.com
Other Media
Ramp is trying to get the US government as a customer after seeing a tweet from DOGE
Expense management startup Ramp is being considered for a charge card pilot program by the U.S. government’s General Services Administration, the company
techcrunch.com
VCs Who Bet $300 Billion on AI Say DeepSeek Will Fuel Industry
Silicon Valley investors are putting sunny spin on the tech industry’s AI model panic.
www.bloomberg.com
What Is Venture Capital Now Anyway?
The opposing paths taken by two powerful firms — Benchmark and Andreessen Horowitz — embody a profound debate about the future of an industry that funds and fosters American innovation.
www.nytimes.com
