Episode 43: The Square IPO
Acquired16 Aug 2017

Episode 43: The Square IPO

Unicorns and ratchets and lawsuits, oh my! Our heroes dive into the history of Jack Dorsey’s famous “other” company, Square. Was the Square IPO a canary in the coal mine signaling doom & gloom for the so-called unicorn companies of the early 2010’s, or a mispriced and misunderstood diamond in the rough? Acquired weighs in.

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© Copyright 2015-2025 ACQ, LLC


Topics Covered Include:

  • Square’s deep origins in the early 90’s in St. Louis, MO with the initial meeting of its co-founders, Jack Dorsey & Jim McKelvey
  • McKelvey’s side glass blowing business and the “inspiration” for Square that came much later in the late 2000’s
  • The complicated involvement of Washington University (in St. Louis) professor Robert Morley, who had worked for years developing payment card reading technology
  • The company’s early meeting with Scott Forstall at Apple, and its “significant” impact on the its name and design
  • The real disruptive innovation of Square and its business model (hint: not just building a mobile card reader)
  • Square’s massive payments deal with Starbucks in 2012 and its impact on the company
  • The evolution of Square’s business from a simple card reader to cloud-based Point of Sale (PoS) system and entire suite of merchant tools & business management services
  • The drama leading up to Square’s IPO (including at Jack Dorsey’s “other” company, Twitter), dynamics and narratives affecting its pricing, the effect of IPO “ratchets”, and the company’s performance over the ~2 years since

The Carve Out:

Episoder(206)

Episode 13: Push Pop Press (Facebook Instant Articles) with Todd Bishop

Episode 13: Push Pop Press (Facebook Instant Articles) with Todd Bishop

Ben and David are joined by Todd Bishop, technology reporter and co-founder of GeekWire, to discuss Facebook's 2011 acquisition of Push Pop Press. Sponsors:WorkOS: https://bit.ly/workos25Sentry: https://bit.ly/acquiredsentryServiceNow: https://bit.ly/acquiredsnMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!© Copyright 2015-2025 ACQ, LLCHighlights Include: The founding story of Push Pop Press by Kimon Tsinteris and Mike Matas.The evolution of Facebook Creative Labs, Facebook Paper, and eventually, Facebook Instant Articles.Facebook's role in the changing media landscape today.GeekWire's experiments with Facebook Instant Articles, Google Accelerated Mobile Pages, and live video.The Carve Out: The Startup Podcast Season 3 The Future of Technology is in Your Ear (Link to product) The Risk Not Taken

6 Jun 20161h 3min

Episode 12: Snapchat

Episode 12: Snapchat

Ben and David tackle their first failed acquisition: Facebook's 2013 offer to buy Snapchat. They cover the fascinating story of Snapchat's creation and growth, their blossoming business model, how it would be different inside of Facebook, and what the future holds.Sponsors:WorkOS: https://bit.ly/workos25Sentry: https://bit.ly/acquiredsentryServiceNow: https://bit.ly/acquiredsnMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!© Copyright 2015-2025 ACQ, LLCItems mentioned in the show:The Inside Story Of Snapchat: The World's Hottest App Or A $3 Billion Disappearing Act?Inside Evan Spiegel's very private Snapchat Story

23 Mai 20161h 3min

Episode 11: PayPal

Episode 11: PayPal

Ben and David return to technology acquisitions by examining a classic: eBay's 2002 purchase of PayPal.Sponsors:WorkOS: https://bit.ly/workos25Sentry: https://bit.ly/acquiredsentryServiceNow: https://bit.ly/acquiredsnMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!© Copyright 2015-2025 ACQ, LLCItems mentioned in the show:  How the 'PayPal Mafia' redefined success in Silicon Valley  - Tech Republic Instagram Will Be a $3 Billion Business This Year: Analyst President Obama and Bill Simmons: The GQ Interview"The Carve Out": Antifragile: Things That Gain from Disorder -  The Bill Simmons Podcast - Chris Sacca

9 Mai 201659min

Acquired Episode 10: Virgin America

Acquired Episode 10: Virgin America

Ben and David deviate entirely from the stated purpose of the show, tackling this non-technology acquisition that is so recent, we have no idea if it went well yet. But, the April 2016 acquisition of Virgin America by Alaska Airlines was so fascinating, we had to do it!Sponsors:WorkOS: https://bit.ly/workos25Sentry: https://bit.ly/acquiredsentryServiceNow: https://bit.ly/acquiredsnMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!© Copyright 2015-2025 ACQ, LLCItems mentioned in the show: Louis C.K. - Everything is Amazing and Nobody is HappyAlaska Acquires Virgin America Investor Deck“Measuring The Moat” Paper - Michael J. MauboussinBusiness Adventures - Twelve Classic Tales from the World of Wall StreetCarve Out:Michael Mauboussin: "The Success Equation:Untangling Skill and Luck" | Talks at Google

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Episode 9: Writely (Google Docs)

Episode 9: Writely (Google Docs)

Ben and David continue the cloud productivity saga with Google Docs. They examine the suite of acquisitions made by Google with a focus on Writely in 2006. They tackle:The nuts and bolts of the Upstartle (company behind Writely) acquisition, founded by Sam Schillace, Steve Newman and Claudia Carpenter.SaaS offerings in cloud productivity today.Was this a good idea for Google?Google's future bets.A new section: The Carve Out!Sponsors:WorkOS: https://bit.ly/workos25Sentry: https://bit.ly/acquiredsentryServiceNow: https://bit.ly/acquiredsnMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!© Copyright 2015-2025 ACQ, LLC

29 Mar 201649min

Episode 8: Acompli, Sunrise, and Wunderlist (w/ Kurt DelBene)

Episode 8: Acompli, Sunrise, and Wunderlist (w/ Kurt DelBene)

Ben and David have special guest Kurt DelBene on to discuss Microsoft's acquisition of Acompli, Sunrise, and Wunderlist. Kurt is the EVP of Corporate Strategy and Planning at Microsoft, and joins to discuss Microsoft’s cloud-first, mobile-first strategy, and the importance of being cross-platform in the modern era. They cover: How the app of Outlook Mobile on iPhone and Android came to be.How to decide whether to build vs. buy, and how it plays into the strategy for Office.How to preserve a culture and a team, and how Javier Soltero came to run all of Outlook at Microsoft.The origin of Outlook on the PC, originally led by Brian MacDonald as “Ren”.How to balance a business with competing priorities, and a decision-making framework for acquisitions in a large company.How to measure the success of an acquisition, and how sometimes, it’s not by measuring revenue at all.Sponsors:WorkOS: https://bit.ly/workos25Sentry: https://bit.ly/acquiredsentryServiceNow: https://bit.ly/acquiredsnMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!© Copyright 2015-2025 ACQ, LLC

29 Feb 20161h 3min

Episode 7: YouTube

Episode 7: YouTube

Ben and David test the widely-held belief that YouTube was one of the most successful tech acquisitions of all time. In today's world of next-generation video platforms, mobile video, streaming, and chord-cutting, was it actually a great purchase by Google? As discussed in the show, here is Sequoia's original YouTube investment memo - a rarely-shared gold mine for anyone interested in startup investing.Sponsors:WorkOS: https://bit.ly/workos25Sentry: https://bit.ly/acquiredsentryServiceNow: https://bit.ly/acquiredsnMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!© Copyright 2015-2025 ACQ, LLC

3 Feb 201651min

Episode 6: Lucasfilm

Episode 6: Lucasfilm

Riding closely on the tails of Star Wars: The Force Awakens, Ben and David cover Disney's 2012 acquisition of Lucasfilm. In the episode, they mention Walt Disney's original flywheel diagram, seen below.Sponsors:WorkOS: https://bit.ly/workos25Sentry: https://bit.ly/acquiredsentryServiceNow: https://bit.ly/acquiredsnMore Acquired!:Get email updates with hints on next episode and follow-ups from recent episodesJoin the SlackSubscribe to ACQ2Merch Store!© Copyright 2015-2025 ACQ, LLC

19 Jan 201640min

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