DocuSign

10 statements across 8 episodes · 6 bullish · 1 bearish · 6 people on the record · first statement May 7, 2015 by Jon Staenberg · said 63 times in 33 episodes since 2015 · across every show →

Mentions by year

brought up most by Brendon Cassidy (11), Harry Stebbings (9), Josh Breinlinger (6), Jason Lemkin (6), Mitchell Green (3), Jason Calacanis (2), Jake Saper (2), Fred Turner (2)

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036201520162017201820192020202120222023202420252026episodes it came up in
002346201520162017201820192020202120222023202420252026episodesmentions per episode
2026 10 mentions in 6 episodes 2 per episode
2025 11 mentions in 6 episodes 2 per episode
2024 15 mentions in 5 episodes 3 per episode
2023 5 mentions in 4 episodes 1 per episode
2022 5 mentions in 4 episodes 1 per episode
2021 1 mention in 1 episode
2019 3 mentions in 2 episodes 2 per episode
2017 8 mentions in 2 episodes 4 per episode
2016 3 mentions in 2 episodes 2 per episode
2015 2 mentions in 1 episode

every mention, scene by scene, with the transcript →

Everything said about DocuSign, oldest first

May 7, 2015 positive
Disclosure
Staenberg invested in DocuSign and Avalara during later funding rounds
“I'm in DocuSign, which I did later in Avalara, Those are two Seattle companies later.”
Jon Staenberg May 7, 2015 ▶ 10:39 20 VC 034: 250 Investments, AngelList Syndicates and Microsoft with Jon Staenberg
Apr 5, 2017
Assertion Not publicly verifiable
Breinlinger: DocuSign lost 25% of revenue overnight after regulatory shifts
“DocuSign was a fascinating story because we had led a round, and then shortly after that, some regulations changed, and basically they lost 25% of their revenue overnight.”
Josh Breinlinger Apr 5, 2017 ▶ 20:52 20VC: Why Spray & Pray Investing Is Wrong, Why Data-Informed VC Beats Data Driven VC & What To Look For When Investing In A Marketplace with Josh Breinlinger, Managing Director @ Jackson Square Ventures
Apr 5, 2017 positive
Disclosure
Breinlinger: Three of four Jackson Square Ventures unicorns required bridge rounds
“At Jackson Square Ventures, the partners here, we've invested in four unicorn companies, and three of them, Equalogic, DocuSign, and Responsys, they all had bridge rounds.”
Josh Breinlinger Apr 5, 2017 ▶ 20:29 20VC: Why Spray & Pray Investing Is Wrong, Why Data-Informed VC Beats Data Driven VC & What To Look For When Investing In A Marketplace with Josh Breinlinger, Managing Director @ Jackson Square Ventures
Jan 21, 2019 positive
Assertion Supported
Greenspring Associates Direct Portfolio Includes Sonos, DocuSign, and Alibaba
“On the direct side, their portfolio includes the likes of Sonos, App Annie, DocuSign, and Alibaba, just to name a few.”
Harry Stebbings Jan 21, 2019 ▶ 0:27 20VC: The Framework LPs Use To Assess Emerging Managers, What Concerns and Excites LPs in Potential Opportunities & The Current State of Seed Today with Hunter Somerville, Partner @ Greenspring Associates
Mar 8, 2024 negative
Assertion Not publicly verifiable
Cassidy: DocuSign lost S&P deal by ignoring evaluators and end-users
“DocuSign had just, that's all DocuSign did was go C-suite, Salesforce's endorsement, but there was all, there were two other layers of people, right? Evaluators and users that were, and then we just basically, Sam and I were like, yeah, And at that, at this po…”
Brendon Cassidy Mar 8, 2024 ▶ 42:10 Brendon Cassidy: Why You Should Never Hire Someone You Do Not Know in Your First Five Hires | E1124 · 20VC with Harry Stebbings
Jun 12, 2025
Insight
Jason Lemkin: Big venture returns require TAM explosions for top players
“I think the venture lesson, be visionary, but relentlessly honest about TAM. Because it's a TAM story at the end of the day. If you have a number one or number two player in the space and you see a TAM explosion happening, that's where you get a big lift, righ…”
Jason Lemkin Jun 12, 2025 ▶ 39:34 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Jun 12, 2025 positive
Disclosure
O'Driscoll: Scale invested in DocuSign at $1 and $2 per share
“We did the round at a buck and two bucks, right?”
Rory O'Driscoll Jun 12, 2025 ▶ 38:01 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Aug 7, 2025
Disclosure
Scale Venture Partners invested in HubSpot, Box, DocuSign, and RingCentral in 2009
“Yes, I remember that was in O-Nine. We did HubSpot, Box, DocuSign, and I think RingCentral.”
Rory O'Driscoll Aug 7, 2025 ▶ 45:37 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Sep 18, 2025 positive
What-if
Lemkin: EchoSign would have sold for $1B as #2 to DocuSign
“Even if EchoSign had just done okay, and we'd gotten up to a hundred million, just the folks that DocuSign turned down would have come and bought us for a billion bucks. Like, I wouldn't have had to do anything just being number two.”
Jason Lemkin Sep 18, 2025 ▶ 1:09:08 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Feb 26, 2026 bullish
Opinion
Rory O'Driscoll: DocuSign and Toast are absurdly cheap at 7-8x revenue
“I mean, I was looking, thinking about companies like Toast. I was thinking about one of our own DocuSign. At eight or seven or eight times revenues, these things are absurdly cheap.”
Rory O'Driscoll Feb 26, 2026 ▶ 5:59 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
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