Understanding equity at tech companies, with Billy Gallagher of Prospect
Why do billions of dollars of stock trade hands based on napkin math and vibes? Billy Gallagher, CEO of Prospect and former Rippling employee, joins Patrick McKenzie (patio11) to walk through the information asymmetry that costs less-sophisticated employees massive amounts of money. From understanding when to early exercise options to navigating 83B elections and tender offers, they discuss the critical decisions that have a shot clock ticking the day you sign your offer letter.–Full transcript available here: www.complexsystemspodcast.com/understanding-equity-at-tech-companies/–Sponsor: Framer is a design and publishing platform that collapses the toolchain between wireframes and production-ready websites. Design, iterate, and publish in one workspace. Start free at framer.com/design with code COMPLEXSYSTEMS for a free month of Framer Pro.–Links:Prospect: www.joinprospect.com/–Timestamps:(00:00) Intro(00:44) Billy's professional journey(01:07) Equity management challenges(02:29) The importance of equity compensation(04:53) Equity grant structures in startups(06:09) Understanding vesting terms(07:09) The value of equity over time(08:48) The myth of options as lottery tickets(11:23) Career tailwinds from startup experience(14:25) Breaking into the tech industry(15:16) The role of equity in compensation(17:49) Employee equity plans and dilution(19:59) Sponsor: Framer(21:06) Stock options vs. RSUs(21:55) The decision to exercise options(27:11) Tax implications of exercising options(33:03) The role of HR in equity management(36:14) Bootleg spreadsheets and vibes-based investing(38:09) Navigating tax complexities in different scenarios(41:31) The importance of extended exercise windows(44:18) Challenges with tax residency and remote work(49:43) The role of accountants in managing equity(53:41) Understanding the 83(b) election and QSBS(01:01:03) Tender offers and secondary sales(01:08:38) Strategies for exercising and selling options(01:12:28) Navigating financial decisions in startups(01:16:59) Wrap
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1:18:31
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1:18:31
The $4,000 insurance policy designed to never pay out
Patrick McKenzie (patio11) reads his essay on title insurance, a service designed to never be performed with a "laughably low" 5% loss ratio compared to 50-80% for almost all types of insurance. The typical American moves every seven to eight years, paying a $500 annual tax for basically no good or service. This is due to a quirk about how America records real estate ownership: it mostly doesn’t. Confused? Welcome to the joyous anarchy that is American real estate.–Full transcript available here: www.complexsystemspodcast.com/the-4-000-insurance-policy-designed-to-never-pay-out/–Sponsor: Framer is a design and publishing platform that collapses the toolchain between wireframes and production-ready websites. Design, iterate, and publish in one workspace. Start free at framer.com/design with code COMPLEXSYSTEMS for a free month of Framer Pro.–Links:Bits about Money, Working title (insurance) https://www.bitsaboutmoney.com/archive/working-title-insurance/–Timestamps:(00:00) Intro(01:59) What is "title," anyway?(02:48) Distributed versus centralized database design in property rights(04:50) A quick digression for privacy-minded buyers(08:21) High confidence and complete confidence are different(11:28) Title insurance and title searches(14:33) One very quirky risk transfer and a statistical artifact(19:14) How title insurance is sold(20:03) Sponsor: Framer(21:34) How title insurance is sold (cont’d)(23:36) Is there anything to be done here?(25:47) Potential innovations in title insurance
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28:31
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28:31
How deposit insurance actually works
Patrick McKenzie (patio11) reads his Bits about Money essay on deposit insurance, explaining this critical financial infrastructure, with some thoughts on its performance during 2023. He covers what deposit insurance actually covers (and critically, what it doesn't), how fintech users often misunderstand their exposure to counterparty risk, and the anatomy of bank failures. This is infrastructure you rely on as much as electricity: ubiquitous, critical, hopefully invisible, and worth understanding before it matters again.–Full transcript available here: www.complexsystemspodcast.com/how-deposit-insurance-actually-works/–Sponsor: Framer is a design and publishing platform that collapses the toolchain between wireframes and production-ready websites. Design, iterate, and publish in one workspace. Start free at framer.com/design with code COMPLEXSYSTEMS for a free month of Framer Pro.–Links:Bits about Money, https://www.bitsaboutmoney.com/archive/deposit-insurance/ –Timestamps:(00:00) Intro(03:10) The covered peril(07:07) Anatomy of a bank failure(12:55) Keeping your bank hydrated(19:58) Sponsor: Framer(23:20) Orderly bank failures(28:25) The cost of insurance(30:15) The ultimate backstop(31:48) Deposit insurance as ubiquitous infrastructure
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33:06
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33:06
Home improvement lending with fewer bankers and more computers
In this episode, Patrick McKenzie reads his essay about the financial infrastructure that makes buying windows painless. When a window installer can originate, underwrite, and fund a $25,000 loan in 15 minutes before leaving your house, it's because four parties—window companies, facilitating platforms, specialized banks, and capital providers—have built a system that actually works. Patrick explains how modern consumer lending learned from 2008 to create better underwriting, clearer compliance, and properly distributed risk, all in service of enabling commerce in the real economy.–Full transcript available here: www.complexsystemspodcast.com/home-improvement-lending/–Sponsor: Framer is a design and publishing platform that collapses the toolchain between wireframes and production-ready websites. Design, iterate, and publish in one workspace. Start free at framer.com/design with code COMPLEXSYSTEMS for a free month of Framer Pro.–Links:Bits about Money: https://www.bitsaboutmoney.com/archive/window-modern-loan-origination/ –Timestamps:(00:00) Intro(02:46) Why not just have banks loan money for home improvement?(06:43) Modern installment loan origination as a service(09:58) Sponsor: Framer(11:09) Modern installment loan origination as a service (part 2)(15:17) What's the actual product offered?(19:03) How does this pie get divvied up?(24:12) Is this unsecured lending?(26:12) Should we be happy this Rube Goldberg machine exists?
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30:05
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30:05
Talking to the Bank of England about systemic risk and systems engineering
Patrick McKenzie (@patio11) shares his remarks to the Bank of England on critical vulnerabilities in financial infrastructure. Drawing from the July 2024 CrowdStrike outage which brought down teller systems at major US banks, Patrick discusses how regulatory guidance inadvertently created dangerous software monocultures. He also examines the stablecoin market, its impressive growth, and the elephant tethered to the room. He also delivers a message from Silicon Valley to other centers of power on the urgent necessity of waking up regarding AI, which almost the entire world currently far underrates.–Full transcript available here: www.complexsystemspodcast.com/talking-to-the-bank-of-england/–Sponsor: Framer is a design and publishing platform that collapses the toolchain between wireframes and production-ready websites. Design, iterate, and publish in one workspace. Start free at framer.com/design with code COMPLEXSYSTEMS for a free month of Framer Pro.–Links:The Bank of England: https://www.bankofengland.co.uk/ Bits about Money, Why the CrowdStrike bug hit banks hard: https://www.bitsaboutmoney.com/archive/crowdstrike-bug-hit-banks-hard/ Scaling Laws for Neural Language Models" by Kaplan et al: https://arxiv.org/pdf/2001.08361 Stripe Annual Letter 2024: https://stripe.com/annual-updates/2024 –Timestamps:(00:00) Intro(01:48) The importance of implementation-level understanding(03:00) Single points of failure(04:25) Can a 22-year-old engineer close all the banks?(05:18) The CrowdStrike incident: A case study(08:34) The culture of "shut up and shuffle"(09:54) Blameless postmortems(12:25) What actually happened during CrowdStrike(18:01) Five whys: Root cause analysis(19:03) How software monocultures are created(22:54) Understanding endpoint monitoring software(25:25) Distributed systems and the nature of CrowdStrike(31:22) The economics of software monocultures(33:29) Why wasn't there defense in depth?(37:05) Why was recovery so difficult?(40:32) The domino effect across financial institutions(43:36) What went right: Electronic systems remained up(45:10) This was a near miss(49:29) Potential policy responses(54:03) Switching gears: Stablecoins(01:01:37) The elephant in the room: Tether(01:15:32) Who loses if Tether implodes?(01:16:59) AI and the future of trading(01:26:47) AI risks in the trading space(01:30:41) Closing
We live in a world where our civilization and daily lives depend upon institutions, infrastructure, and technological substrates that are _complicated_ but not _unknowable_. Join Patrick McKenzie (patio11) as he discusses how decisions, technology, culture, and incentives shape our finance, technology, government, and more, with the people who built (and build) those Complex Systems.
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