Startup Employees

topic on 6 shows · 14 statements across 12 episodes

the Y Combinator Startup Podcast Latent Space the Official SaaStr Podcast Capital Allocators TBPN 20VC

14 statements about Startup Employees, every show

20VC Insight
O'Driscoll: Optimal employee equity timing precedes secondary tender offers
“The whole trick for employees, just like it is for VCs, is to join something that isn't doing a tender offer today, get a healthy grant, and join a company that within a year or two, when you've vested 50, 60% of your thing, starts doing tender offers.”
Rory O'Driscoll Jul 9, 2026 ▶ 1:23:34 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
Startup employees frequently mishandle their equity and tax obligations
“If somebody with my background at this point in the game is screwing up startup equity, I'm sure your average startup employee is also probably screwing up their startup equity.”
Dave Thornton Nov 6, 2025 ▶ 4:26 Dave Thornton – Unlocking Venture Access Through Stock Options at Vested (EP.469)
Financing employee stock options creates proprietary data on opaque private companies
“If you help a broad base of startup employees, you will end up with a ton of differentiated data on private companies that may or may not be out there in the world otherwise.”
Dave Thornton Nov 6, 2025 ▶ 15:16 Dave Thornton – Unlocking Venture Access Through Stock Options at Vested (EP.469)
CAPITAL ALLOCATORS Assertion Supported
70% of startup employees abandon their stock options upon departure
“At the moment, around 70% of employees abandon their stock options, and employees tend to own 10 to 15 points of the cap table of a given startup.”
Dave Thornton Nov 6, 2025 ▶ 38:34 Dave Thornton – Unlocking Venture Access Through Stock Options at Vested (EP.469)
Junestrand: Startup employees must scale exponentially rather than linearly as company grows
“The company is growing exponentially, so you need your teammates to scale exponentially as well. If people scale linearly, at some point it's a really large delta, and then, you know, things aren't working out anymore.”
Max Junestrand Aug 26, 2025 ▶ 22:14 How This 25-Year-Old Built A $675M Legal AI Startup (With No Legal Experience) · Y Combinator
Palazzolo: Unbalanced AI acqui-hires are eroding employee-founder trust
“There's a sense that whenever you join a startup, like, you're gonna be compensated for the risk that you're taking on of joining, like, something that's unproven, and then now you're having these situations where, like, yeah, some people do get rewarded for t…”
Stephanie Palazzolo Aug 6, 2025 ▶ 46:32 The AI Agenda: GPT5 leaks and the business of AI News — Steph Palazzolo, The Information
TBPN Opinion
Glyman: Many startups have not marked to market, stranding employee equity
“I still think a lot of companies haven't taken their medicine. They actually haven't just marked it to market. And I think that a lot of employees who've been working hard probably are still underwater.”
Eric Glyman Mar 6, 2025 ▶ 8:32 Ramp's CEO Eric Glyman reflects on the journey to $13 Billion and their exciting future
Seibel: Great startup employees are motivated, not discouraged, by severe bad news
“I've been often surprised at like sharing bad news. Like, oh, we only have two months of runway. Right. I would think would be demotivating, but for great startup employees, they're like, all right, how the fuck are we going to fix this? And then you can get j…”
Michael Seibel Feb 23, 2023 ▶ 18:00 The Hard Conversations Founders Don't Want to Have · Y Combinator
SAASTR Insight
Lemkin: Startup employees rarely get rich without a $10B+ exit
“You know, it, it's very hard for most employees to make money on anything that doesn't have a ten billion dollar plus outcome. It's very hard to get rich as an employee.”
Jason Lemkin Feb 3, 2023 ▶ 24:03 What Venture Looks Like In 2023 | SaaStr Founder Jason Lemkin + 20VC Host Harry Stebbings
Seibel: Employees copy founder behaviors because founders define company success
“They will copy what you're doing because you define success in your company.”
Michael Seibel Jan 11, 2023 ▶ 27:23 The Secrets To Setting Smarter Goals · Y Combinator
20VC Insight
Smith: Startup employees treat equity as a lottery ticket with zero value
“If you think about how most engineers, or really a lot of individual employees in their risk profile, how they think about equity, if you talk to many of them, even the most savvy people often really think of equity as a lottery ticket. And if you think of it …”
Sarah Smith Apr 29, 2019 ▶ 21:36 20VC: Why Lead Lime's Series D Funding Round, Why Engineers Are Underpaid & Why 74% of US Venture Firms Still Do Not Have Female GPs
Garg: Early startup employees stay longer when founders share hard times transparently
“Sometimes you think you're protecting people by not telling them, but actually your closest employees, especially when you're four to six, if you bring them into the challenge, And if they are challenge oriented, they will stay with you. But if you hide it, th…”
Ooshma Garg Sep 8, 2018 ▶ 29:01 A Conversation with Ooshma Garg - Moderated by Adora Cheung · Y Combinator
20VC Insight
Dan Lewis: The best indicator of scaling is hiring your own replacement
“That is the best indicator as to whether someone's ready to scale with the company and step up and take on a bigger role and more responsibility is, are they able to step back and recognize that they need to hire someone to do their own job? Can they be comfor…”
Dan Lewis Mar 23, 2018 ▶ 24:40 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
CAPITAL ALLOCATORS Assertion Contradicted
Hamed: Banks lend to founders but ignore rank-and-file startup employees
“Banks have provided liquidity to founders all the time with PGs, but there's no one who's really been serving employee 20 through 2000.”
Ali Hamed Feb 19, 2018 ▶ 27:34 Ali Hamed - Novel Asset Investing (Capital Allocators, EP.40)

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