Skype

includes Skype 4.0

14 statements across 13 episodes · 3 bullish · 2 bearish · 13 people on the record · first statement May 4, 2015 by Chris Dark · said 106 times in 52 episodes since 2015 · across every show →

Mentions by year, the whole family

brought up most by Josh Silverman (25), Harry Stebbings (18), Akin Babayigit (11), Chris Dark (5), Taavet Hinrikus (4), Jason Lemkin (4), Steve O'Hear (2), Sitar Teli (2)

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0510201520162017201820192020202120222023202420252026episodes it came up in
0045810201520162017201820192020202120222023202420252026episodesmentions per episode
2026 3 mentions in 1 episode
2025 8 mentions in 5 episodes 2 per episode
2024 6 mentions in 4 episodes 2 per episode
2023 14 mentions in 3 episodes 5 per episode
2022 1 mention in 1 episode
2021 29 mentions in 4 episodes 7 per episode
2020 2 mentions in 1 episode
2019 3 mentions in 2 episodes 2 per episode
2018 6 mentions in 6 episodes 1 per episode
2017 7 mentions in 6 episodes 1 per episode
2016 9 mentions in 9 episodes 1 per episode
2015 18 mentions in 10 episodes 2 per episode

every mention, scene by scene, with the transcript →

Everything said about Skype, oldest first

May 4, 2015
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
Jan 4, 2016 positive
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"
Apr 6, 2016
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
Dec 4, 2017
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
Sep 28, 2018 neutral
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
Feb 17, 2020
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
Jan 18, 2021 positive
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
Jan 18, 2021
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
Feb 15, 2021 negative
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
Nov 28, 2022 positive
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
Jun 26, 2023 negative
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
Nov 27, 2024 neutral
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
Apr 28, 2025
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
Jan 29, 2026
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
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