Stock Options

topic on 12 shows · 28 statements across 21 episodes

BG2 Pod Startups For the Rest of Us the Knowledge Project BigDeal David Senra My First Million the Official SaaStr Podcast Capital Allocators Top Founders the a16z Podcast All-In 20VC

28 statements about Stock Options, every show

BIGDEAL Assertion Supported
Sanchez: Between 70% and 90% of stock options end up worthless
“I read a study the other day that said somewhere between 70 and 90% of stock options end up worthless.”
Codie Sanchez Feb 27, 2026 ▶ 52:40 Wealth Expert: Do THIS Every Time You Get Paid | Morgan Housel
Fried: Startup Stock Options and RSUs Are Largely Bullshit
“No options, no RSUs, no stock, no, like, any of that BS. I find almost all that to be pretty much BS, unless you're like a really well-established public company.”
Jason Fried Feb 15, 2026 ▶ 1:34:01 Jason Fried: Your Only Competition Is Your Costs
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)
KNOWLEDGE PROJECT Assertion Contradicted
Parrish: Most Share Buybacks Merely Cover Up Stock Option Dilution
“You know, if you look at most buybacks, they're just covering up stock options.”
Shane Parrish Oct 28, 2025 ▶ 1:01:42 Forensic Account: The Bubble No One is Talking About | Anthony Scilipoti
Scilipoti: Stock Options Must Be Accounted for as an Operating Expense
“I think stock options should be an expense. And if they're not an expense, I borrow from Buffett and even the chair of the accounting has said things like this, that, that if it's not an expense, then what is it?”
Anthony Scilipoti Oct 28, 2025 ▶ 1:03:48 Forensic Account: The Bubble No One is Talking About | Anthony Scilipoti
KNOWLEDGE PROJECT Assertion Contradicted
Diller asserts 80% to 90% of employees immediately cash out vested options
“What I have learned is that most people, you think that giving large populations options in the company's securities, that they would hold on to them. And what you find out is 80, 90%. The first moment that they, quote, vest, they cashed them.”
Barry Diller Sep 30, 2025 ▶ 50:43 Barry Diller: Building IAC
20VC Insight
Riparbelli: European startup employees still view stock options as lottery tickets
“In Europe, I think people, again, for good and for better and for worse, right? I think people are, they think less like that, right? As you of course know, like stock options in Europe, people still view it as like, A random lottery ticket, not really as part…”
Victor Riparbelli Jan 15, 2025 ▶ 57:57 Victor Riparbelli, CEO @Synthesia: OpenAI vs Anthropic vs X.ai - Who Wins and Why | E1246 · 20VC with Harry Stebbings
MY FIRST MILLION Assertion Contradicted
Puri: Two-thirds of late-stage startup employee stock options are underwater
“Two thirds of employees right now that are working at these companies are working for options that are actually worth zero, and they probably don't even realize it yet, meaning they got a pay package of stock options at a 24 dollar strike price. That stock is …”
Shaan Puri Sep 13, 2024 ▶ 5:18 10 Startups w/ Stock Grants That’ll Make You A Millionaire | Sara’s List 2024
BG2 Insight
Gurley: Startup option dilution drops from ~10% early on to ~3% near IPO
“When a startup would get started in early years, you might have as much as, say, 10% dilution from options. You might hire three executives during that year, and it's a big grant, but then as you move towards being public, people would typically, and these are…”
Bill Gurley Mar 21, 2024 ▶ 6:19 Ep5. Stock Comp, AI Cold War, Valuations for LLM | BG2 with Bill Gurley, Brad Gerstner, & Bob Mylod · Bg2 Pod
BG2 Insight
Gurley: Black-Scholes values one RSU at roughly 2.5 to 3 options
“There's an argument from Black Shoals that a single RSU is worth about two and a half or three options. So if you could switch From these options to an RSU, this investor thought dilution might drop from, say, four percent to 1.2% or something like that, and t…”
Bill Gurley Mar 21, 2024 ▶ 6:46 Ep5. Stock Comp, AI Cold War, Valuations for LLM | BG2 with Bill Gurley, Brad Gerstner, & Bob Mylod · Bg2 Pod
ALL-IN Insight
Calacanis: Early-stage startups are shifting equity to top 10% and outsourcing rest
“The trend I'm seeing with startups, like early stage startups, seed stage startups, which are really indicative of what startups will do later on, hiring people, cash basis, paying them hourly outside the United States, not having to worry about stock options,…”
Jason Calacanis Feb 17, 2024 ▶ 59:13 E166: Mind-blowing AI Video: OpenAI launches Sora + Is Biden too old? Tucker/Putin interview & more
ALL-IN Opinion
Sacks: Eliminating stock options for rank-and-file startup employees is a terrible idea
“But the fact of the matter is that Silicon Valley had a share of the wealth mentality where the rank and file employees did participate in the ownership of the company and they got equity. And it was highly motivating or it is highly motivating. For not just l…”
David Sacks Feb 17, 2024 ▶ 1:00:18 E166: Mind-blowing AI Video: OpenAI launches Sora + Is Biden too old? Tucker/Putin interview & more
Gaynor: A stock option is economically an interest-free loan
“An option is basically an interest free loan.”
Tom Gaynor Jan 23, 2024 ▶ 1:48:35 Tom Gayner: Invest Like The Best
Gayner Automatically Rejects Investing in Companies That Issue Heavy Stock Options
“If I saw a company that was using a lot of option stuff, I would just put my pencil down and say, I just don't like that. So it's in the too hard pile, and I'm not going to try to calculate that to the fourth decimal point. I just don't want to be part of it.”
Tom Gaynor Jan 23, 2024 ▶ 1:48:54 Tom Gayner: Invest Like The Best
20VC Assertion Not checkable as stated
Seibert: Many tech employees are trapped at startups with underwater stock options
“A lot of folks, you're right, are trapped in companies with high valuations where their options are likely underwater.”
Jeff Seibert Nov 22, 2023 ▶ 51:11 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Shopify lets employees choose their own cash and equity compensation split
“These switch to a very simple system where everyone gets a number. This is what you make every year. And so everyone agrees what, like, the ground truth is of compensation. And then you can say, we want this in cache. Do you want this in store options?”
Tobi Lütke Nov 15, 2022 ▶ 44:29 Tobi Lütke: Calm Progress
Godin: Stock options are a massive demotivator in almost every organization
“You know, one of the challenges of the whole stock option thing is entrepreneurs and founders think that other people will be as motivated by owning part of the company as they are. They're not, not even close. It's a sort of a prize pool at the end of the gam…”
Seth Godin Feb 23, 2021 ▶ 1:18:10 #105 Seth Godin: Failing On Our Way To Mastery
Cooney: Cash profit-sharing is better than stock options that often yield nothing
“I mean, we look at, you know what's the stock shop, stock options or share options and all that, but We just found that as the income comes in and as we're profitable, we wanted to go direct to them. I'm tired of the stories of people that get stock options an…”
Michael Cooney Dec 19, 2020 ▶ 10:14 WhatConverts Hits $2.1m Revenue, $300k Profits in Call Tracking Space
Walling: Profit Sharing Better Aligns Incentives Than Discretionary Bonuses
“Lastly, bonuses are tough because incentives aren't exactly aligned, are they? Because something about profit sharing that's nice is if the company doesn't turn a profit that year, people don't get the profit sharing. Whereas if the company doesn't turn a prof…”
Rob Walling Oct 20, 2020 ▶ 7:01 Episode 519 | Profit Sharing, Stock Options, and Equity (A Rob Solo Adventure)
Walling: 90-day post-termination option exercise windows are unethical
“You usually have about three months, and if you don't buy the options, they just revert back to the company, and you get nothing. And that's an interesting, I don't really like that. I actually disagree with that. I don't think it's super ethical, and I feel l…”
Rob Walling Oct 20, 2020 ▶ 13:47 Episode 519 | Profit Sharing, Stock Options, and Equity (A Rob Solo Adventure)
SAASTR Insight
Wilson: Calculate annual advisor equity by dividing $12,000 by share price
“The way that I've structured it is real simple. What would I pay this person as a consultant? You know, if I were to meet them at a party and say, Hey, I really have this problem. Can you help me to do this? How much would I pay them? Now, of course, this will…”
Andy Wilson May 20, 2020 ▶ 28:56 Lessons from Logikcull: $0 to $10M in 19 Months: The How, When & Why + 10 Mistakes Along the Way
a16z Insight
Lohman: Stock options strictly outperform RSUs for high-growth pre-IPO startups
“There's really no scenario where RSUs are better than options in that model. And so from a pure upside, from a pure opportunity perspective, from a flexibility perspective, from a tax perspective, from an administrative perspective, there are lots of advantage…”
Greg Lohman Jan 2, 2019 ▶ 22:55 a16z Podcast | All Things Compensation
a16z Assertion Supported
Horowitz: Pre-2000s accounting laws forced 90-day startup option windows
“And the then accounting laws basically said that if you gave an employee more than, you know, a very short window to exercise, you would potentially create a very large accounting charge, which would make it impossible for the company to ever go public or be a…”
Ben Horowitz Jan 2, 2019 ▶ 1:19 a16z Podcast | Beyond One Size Fits All for Startup Employee Options
a16z Assertion Supported
Horowitz: Startups kept 90-day option windows even after accounting laws changed
“So they changed the law and the law, the new law kind of made it okay to have a longer exercise period, but nobody changed the practice.”
Ben Horowitz Jan 2, 2019 ▶ 2:11 a16z Podcast | Beyond One Size Fits All for Startup Employee Options
a16z Insight
Horowitz: 90-day option windows create a wealth disparity for startup employees
“If you're rich and you have 90 days to exercise, that's fine because you can buy your stock options. But if you're not rich, then you can't. And so now we've created this class thing.”
Ben Horowitz Jan 2, 2019 ▶ 2:23 a16z Podcast | Beyond One Size Fits All for Startup Employee Options
a16z Assertion Not checkable as stated
Schultz: Candidates stopped negotiating for options after 2000 tech crash
“So if you look back in, you know, early 2000, like nobody was really thinking, nobody was negotiating options for a while. No, it was like, I need to be paid cash. I don't really care about options.”
Shannon Schiltz Jan 2, 2019 ▶ 29:46 a16z Podcast | Compensation Isn’t About Paying the Most, It’s About Being Consistent
a16z Insight
Morrill: Overhyped equity options create severe retention crises during repricings
“It's almost like we've taken stock options and we've hyped them up more than we should have, because then you do have this trust problem where if you do have to do something for the survival of the company, Now you're telling a couple thousand people, hey, we …”
Danielle Morrill Jan 2, 2019 ▶ 21:01 a16z Podcast | Raising Money and Valuing Startups -- What Happens When Things Don't Go As Planned?
TOP FOUNDERS Assertion Not checkable as stated
Epstein: Most Detroit Companies Do Not Offer Stock Options
“Most companies, In our area don't give equity or stock options, right?”
Jeff Epstein Sep 17, 2018 ▶ 8:39 1150 Detroit Based Referral Program software passes $600k in MRR

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