The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

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why aren't all 14 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Opinion
Reber: Microsoft screwed up its acquisitions of Yammer, Skype, and Wunderlist
“I think Microsoft has Screwed up multiple acquisitions like Yammer or Skype, and they promised me when we sold it that they will try their very best not to screw up Wunderlist, and I think they did.”
Christian Reber Feb 15, 2021 ▶ 10:23 20VC: Wunderlist & Pitch Founder, Christian Reber on His Personal Relationship with Risk, Money, Whether the Sale to Microsoft was a Mistake, What Great Product Designs Means Today & Why Founders Investing External Capital is a Distraction
Insight
Multi-Billion Dollar Consumer Businesses Must Be Free or Better and Cheaper
“If you want to build a truly mid-market, kind of, you know, I'm focused on businesses that will become large, enduring, multi-billion dollar businesses, and I think in order to build one of those, You either have to figure out how to give something away for fr…”
Sarah Tavel Apr 6, 2016 ▶ 21:56 20VC: Greylock's Sarah Tavel on What Founders Need From A Good Investor and Why Products Need To Be 10X Better & Cheaper
Assertion Not checkable as stated
Silverman: eBay spent four months seeking Skype CEO before hiring him
“When they asked me to run Skype, I was at eBay. Honestly, they spent four months looking to find anyone else, and no one would take that job because, you know, it's in the telecommunications industry, which is highly regulated, and international phone calls we…”
Josh Silverman Jan 18, 2021 ▶ 7:48 20VC: Etsy CEO, Josh Silverman on 2 Defining Traits of Great Leadership, The Danger of Attaching Happiness To Milestones, How To Structure Teams To Optimise for Experimentation and Agility &Whether You Learn More From Success Than Failure
Assertion Supported
Hommels: Skype lacked a business model when he invested
“So at the time when I invested in Skype, there was no business model, because with Skype out wasn't even invented.”
Klaus Hommels Nov 27, 2024 ▶ 53:17 Klaus Hommels: Why "Portfolios are Merely a Construct to Make LPs Happy"? | E1231 · 20VC with Harry Stebbings
Opinion
Babayigit: Skype Could Have Dominated Far More Than It Did
“And it was dominating the voice over IP market, and it could have dominated so much more.”
Akin Babayigit Jun 26, 2023 ▶ 6:58 Akin Babayigit: How Tripledot Studios Became #1 Fastest-Growing Company in Europe | E1030 · 20VC with Harry Stebbings
Insight
Kuusi: A tech company's biggest impact is its talent ecosystem, not its product
“Like if you think about like, you know companies like PayPal and Skype and so forth, like, you know, these companies, I would argue the biggest impact of those companies wasn't the services they created. It's the people that they touched and what those people …”
Miki Kuusi Nov 28, 2022 ▶ 1:13:00 Miki Kuusi: How I Scaled Wolt to $8B; Why I Sold to DoorDash | 20VC #953 · 20VC with Harry Stebbings
Assertion Partly supported
Silverman: Pivoting Skype to video calling dramatically altered its growth curve
“Pivoting Skype from audio calls to video calls was probably the most powerful way to drive engagement. And so we made video calling the centerpiece of Skype for that out, changed Skype's brand, really, and mission to be about video. Shipped an amazing product …”
Josh Silverman Jan 18, 2021 ▶ 23:31 20VC: Etsy CEO, Josh Silverman on 2 Defining Traits of Great Leadership, The Danger of Attaching Happiness To Milestones, How To Structure Teams To Optimise for Experimentation and Agility &Whether You Learn More From Success Than Failure
What-if
Openwave could have built Skype or Twitter by diversifying beyond telecom carriers
“If we had taken the time to think carefully about who our customer base should be, you know, we could have built technologies like Skype, like Twitter as opposed to just continuing to build technology, selling to Orange or Singular or Nextel or AT&T, the custo…”
Rich Wong Dec 4, 2017 ▶ 17:38 20VC: Accel GP, Rich Wong on When Is The Right Time To Scale A Startup, Optimising Initial vs Follow-On Investment Decision-Making & The Globalisation of VC In Recent Years
Assertion Not publicly verifiable
Skype reached 400,000 users within 20 days of launch
“It was three, 400,000 users after 20 days, and the rest is more or less history.”
Morten Lund Jan 4, 2016 ▶ 6:11 20 VC: Morten Lund on Skype, Bankruptcy, Fintech and Why "Banks Are Full Of Lots Of Stupid People Doing Nothing"
What-if
Chris Dark: Skype's success depended entirely on its exact launch timing
“If they'd done it two years earlier, Wouldn't have worked. Two years later, it would have been too late.”
Chris Dark May 4, 2015 ▶ 19:21 20 VC 033: The Pros and Cons of Venture Capital, Atomico and Entrepreneurship with Chris Dark, President International @ C2FO
Assertion Partly supported
Lemkin: Andreessen Horowitz tripled its money on Skype in 12-14 months
“And the reason it was a structurally weird deal where they got a good deal. Now they took risks. Skype was a aging platform, but they bought it from eBay, right? Is that eBay needed to divest it? They had enough of it. There was no synergy and Andreessen went …”
Jason Lemkin Jan 29, 2026 ▶ 16:58 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Assertion Not checkable as stated
Hinrikus has been financially independent since 2002 via Skype options
“I was also lucky to make money from being the first employee at Skype from stock options. So in that sense, I've been financially Independent since 2002, three.”
Taavet Hinrikus Apr 28, 2025 ▶ 58:07 Plural Partner, Taavet Hinrikus: Why Founders Will Realise Multi-Stage Funds Damage Seed Rounds · 20VC with Harry Stebbings
Disclosure
Kutcher's early angel portfolio included Skype, Alibaba, and Foursquare
“I invested in Skype and Alibaba and Foursquare and this platform called Brizly, which was like a Twitter client And just started putzing around and finding my way towards interesting companies and interesting people and had some early success, which then led m…”
Ashton Kutcher Feb 17, 2020 ▶ 7:08 20VC: Ashton Kutcher on Early Lessons From Investing in Airbnb and Spotify, Why VC Ownership Requirements Are Becoming More and More Egregious & What Being Good At Product Truly Means
Disclosure
Webb: eBay evaluated the Skype acquisition using a waterline risk framework
“When we were looking to buy Skype at eBay, we used that analogy to say, okay, if it doesn't work, is it going to hit us above the waterline where it's going to be ugly and we're going to have to fix it, but it's fixable? Or is it going to hit us below the wate…”
Maynard Webb Sep 28, 2018 ▶ 18:52 20VC: How The Best Founders Approach Bet The Company Decisions, How to Put Your Board to Work & How To Optimise Strategic Thinking on Boards with Maynard Webb, Founder @ Webb Investment Network & Everwise
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