| $200M2025-01-27 | Perk (formerly TravelPerk) | Hillary Ball, Mark Crane, Joel Cutler |
| $200M2025-01 | Perk (formerly TravelPerk) | Mark Crane, Joel Cutler |
| $47M2024-03-12 |  Empathy | General Catalyst, MassMutual, Worklife, Index Ventures, Brewer Lane Ventures, Latitude, Joel Cutler |
| $47M2024-03 | Empathy | Joel Cutler |
| $200M2024-01-24 |  Bilt | General Catalyst, Eldridge, Prosus Ventures, Left Lane Capital, GID, Camber Creek, Kenneth Chenault, Joel Cutler |
| $200M2024-01 | Bilt | Kenneth Chenault, Joel Cutler |
| $57M2023-10-17 |  Nirvana Insurance | Lightspeed, General Catalyst, Valor Equity Partners, Joel Cutler, Hemant Taneja |
| $57M2023-10 | Nirvana Insurance | Joel Cutler, Hemant Taneja |
| $150M2023-06-29 |  Lemonade | Joel Cutler |
| $150M2023-06 | Lemonade | Joel Cutler |
| $60M2022-11-30 |  Joy | General Catalyst, Niko Bonatsos, Joel Cutler |
| $60M2022-11 | Joy | Niko Bonatsos, Joel Cutler |
| $27M2022-06-14 |  Sesame | Joel Cutler |
| $220M2022-06-08 |  Multiverse | General Catalyst, Lightspeed, D1 Capital Partners, GV, StepStone Group, Index Ventures, BOND, Audacious Ventures, Kenneth Chenault, Joel Cutler |
| $27M2022-06 | Sesame | Joel Cutler |
| $220M2022-06 | Multiverse | Kenneth Chenault, Joel Cutler |
| $22M2022-02-23 | Nirvana Insurance | Lightspeed, General Catalyst, Instacart, Joel Cutler |
| $22M2022-02 | Nirvana Insurance | Joel Cutler, Hemant Taneja |
| $120M2022-01-12 | Perk (formerly TravelPerk) | Mark Crane, Joel Cutler |
| $120M2022-01 | Perk (formerly TravelPerk) | Mark Crane, Joel Cutler |
| $72M2021-12-17 | Well | Joel Cutler |
| $80M2021-12-02 |  Zego | Joel Cutler |
| $80M2021-12 | Zego | Joel Cutler |
| $72M2021-12 | Well | Joel Cutler |
| $67M2021-10-13 |  Blank Street | Joel Cutler |
| $67M2021-10 | Blank Street | Joel Cutler |
| $30M2021-09-30 | Empathy | General Catalyst, Aleph, Primetime Partners, Phoenix Court Group, Entrée Capital, Joel Cutler |
| $130M2021-09-28 | Multiverse | General Catalyst, D1 Capital Partners, GV, Index Ventures, BOND, Lightspeed, Latitude, Audacious Ventures, Kenneth Chenault, Joel Cutler |
| $100M2021-09-08 |  Beauty Pie | General Catalyst, Index Ventures, Balderton Capital, Insight Partners, Joel Cutler |
| $100M2021-09 | Beauty Pie | Joel Cutler |
| $30M2021-09 | Empathy | Joel Cutler |
| $130M2021-09 | Multiverse | Kenneth Chenault, Joel Cutler |
| $24M2021-04-27 | Sesame | Joel Cutler |
| $13M2021-04-06 | Empathy | General Catalyst, Aleph, Joel Cutler |
| $24M2021-04 | Sesame | Joel Cutler |
| $13M2021-04 | Empathy | Joel Cutler |
| $150M2021-03-10 | Zego | Rob Moffat, Joel Cutler |
| $150M2021-03 | Zego | Joel Cutler |
| $44M2021-01-19 | Multiverse | Joel Cutler |
| $3M2021-01-01 | Nirvana Insurance | Joel Cutler |
| $3M2021-01 | Nirvana Insurance | Joel Cutler, Hemant Taneja |
| $44M2021-01 | Multiverse | Joel Cutler |
| $—2020-12-16 | Beauty Pie | Joel Cutler |
| $26M2020-12-14 | Well | Kenneth Chenault, Joel Cutler |
| $—2020-12 | Beauty Pie | Joel Cutler |
| $26M2020-12 | Well | Kenneth Chenault, Joel Cutler |
| $15M2020-09-30 |  Bloomscape | Joel Cutler |
| $15M2020-09 | Bloomscape | Joel Cutler |
| $230M2020-06-26 |  Oscar Health | Joel Cutler, Oliver Heimes |
| $230M2020-06 | Oscar Health | Joel Cutler |
| $19M2019-09-01 | Sesame | Joel Cutler |
| $19M2019-09 | Sesame | Joel Cutler |
| $25M2019-06-01 | Well | Kenneth Chenault, Joel Cutler |
| $25M2019-06 | Well | Kenneth Chenault, Joel Cutler |
| $300M2019-04-11 | Lemonade | General Catalyst, OurCrowd, GV, Allianz, SoftBank Vision Fund, Thrive Capital, David Thevenon, Joel Cutler |
| $300M2019-04 | Lemonade | Joel Cutler, Ron Stern |
| $20M2019-02-26 |  ROCKETS OF AWESOME | Joel Cutler |
| $20M2019-02 | Rockets of Awesome | Joel Cutler |
| $170M2018-03-27 | Oscar Health | Joel Cutler |
| $170M2018-03 | Oscar Health | Joel Cutler |
| $120M2017-12-19 | Lemonade | David Thevenon, Joel Cutler |
| $120M2017-12 | Lemonade | Joel Cutler |
| $16M2017-06-20 |  M.Gemi | Joel Cutler |
| $65M2017-06-06 |  Cadre | Joel Cutler, Founders Fund, General Catalyst, Khosla Ventures, Foundation Capital, The Goldman Sachs Group, Inc., Breyer Capital, Thrive Capital, Jeff Jordan |
| $16M2017-06 | M.Gemi | Joel Cutler |
| $13M2017-01-03 | ROCKETS OF AWESOME | Joel Cutler |
| $13M2017-01 | Rockets of Awesome | Joel Cutler |
| $34M2016-12-05 | Lemonade | General Catalyst, Aleph, GV, Thrive Capital, Sequoia Capital, Sequoia, Tusk Venture Partners, Joel Cutler |
| $34M2016-12 | Lemonade | Joel Cutler |
| $7M2016-07-26 | ROCKETS OF AWESOME | Joel Cutler |
| $7M2016-07 | Rockets of Awesome | Joel Cutler |
| $400M2016-02-22 | Oscar Health | Joel Cutler, Oliver Heimes |
| $400M2016-02 | Oscar Health | Joel Cutler |
| $50M2015-11-02 | Handy | Joel Cutler |
| $50M2015-11 | Handy | Joel Cutler |
| $2M2015-10-07 |  Paribus | Joel Cutler |
| $2M2015-10 | Paribus | Joel Cutler |
| $100M2015-04-30 | Warby Parker | Joel Cutler |
| $150M2015-04-20 | Oscar Health | Joel Cutler |
| $100M2015-04 | Warby Parker | Joel Cutler |
| $150M2015-04 | Oscar Health | Joel Cutler |
| $18M2015-03-24 | Cadre | Joel Cutler |
| $14M2015-03-24 | M.Gemi | General Catalyst, Forerunner Ventures, Breakaway, Joel Cutler |
| $18M2015-03 | Cadre | Joel Cutler |
| $14M2015-03 | M.Gemi | General Catalyst, Joel Cutler, Forerunner Ventures, Breakaway |
| $140M2015-02-11 | Jet | Jeff Crowe, Joel Cutler |
| $140M2015-02 | Jet | Joel Cutler |
| $70M2014-08-26 |  The Honest Company | Joel Cutler |
| $7M2014-08-06 | Wildcard | Joel Cutler |
| $7M2014-08 | Wildcard | Joel Cutler |
| $70M2014-08 | The Honest Company | Joel Cutler |
| $15M2014-06-27 | Chloe + Isabel | Joel Cutler |
| $30M2014-06-11 | Handy | Joel Cutler |
| $15M2014-06 | Chloe + Isabel | Joel Cutler |
| $30M2014-06 | Handy | Joel Cutler |
| $80M2014-05-14 | Oscar Health | Joel Cutler |
| $80M2014-05 | Oscar Health | Stanley Druckenmiller, Joel Cutler |
| $30M2014-01-07 | Oscar Health | Joel Cutler, Oliver Heimes |
| $30M2014-01 | Oscar Health | Joel Cutler |
| $60M2013-12-20 | Warby Parker | Joel Cutler |
| $60M2013-12 | Warby Parker | Joel Cutler |
| $25M2013-11-11 | The Honest Company | ICONIQ Capital, Joel Cutler |
| $25M2013-11 | The Honest Company | Joel Cutler |
| $10M2013-10-22 | Handy | Joel Cutler |
| $10M2013-10 | Handy | Joel Cutler |
| $3M2013-07-25 | Trover | Joel Cutler |
| $40M2013-07-19 | Oscar Health | Joel Cutler, Founders Fund, 8VC, GV, General Catalyst, Fidelity Investments, Alphabet Inc. |
| $3M2013-07-01 | Wildcard | Joel Cutler |
| $3M2013-07 | Trover | Joel Cutler |
| $3M2013-07 | Wildcard | Joel Cutler |
| $—2013-06-01 | ViajaNet | Joel Cutler |
| $—2013-06 | ViajaNet | Joel Cutler |
| $30M2013-01-03 | Room 77 | Joel Cutler |
| $30M2013-01 | Room 77 | Joel Cutler |
| $2M2012-10-16 | Handy | Joel Cutler |
| $2M2012-10 | Handy | Joel Cutler |
| $42M2012-09-09 | Warby Parker | Joel Cutler |
| $42M2012-09 | Warby Parker | Joel Cutler |
| $15M2012-08-22 |  CouchSurfing | Matt Cohler, Joel Cutler |
| $15M2012-08 | Couchsurfing | Matt Cohler, Joel Cutler |
| $28M2012-07-02 |  Jumptap | Joel Cutler |
| $28M2012-07 | Jumptap | Joel Cutler |
| $27M2012-03-23 | The Honest Company | Joel Cutler |
| $27M2012-03 | The Honest Company | Joel Cutler |
| $9M2011-11-18 | Chloe + Isabel | Joel Cutler |
| $9M2011-11 | Chloe + Isabel | Joel Cutler |
| $110M2011-07-25 |  Airbnb | Jeff Jordan, Joel Cutler |
| $110M2011-07 | Airbnb | Reid Hoffman, Joel Cutler, Jeff Jordan |
| $11M2011-06-09 | Room 77 | Joel Cutler |
| $11M2011-06 | Room 77 | Joel Cutler |
| $19M2011-05-25 | ViajaNet | Joel Cutler |
| $19M2011-05 | ViajaNet | Joel Cutler |
| $20M2011-04-01 | Jumptap | Joel Cutler |
| $20M2011-04 | Jumptap | Joel Cutler |
| $11M2011-01-04 |  GroupMe | Joel Cutler, David Weiden |
| $11M2011-01 | GroupMe | David Weiden, Joel Cutler |
| $5M2009-08-12 | FanSnap | Joel Cutler |
| $5M2009-08 | FanSnap | Joel Cutler |
| $5M2009-05-07 | Pobts | Jeremy Levine, Joel Cutler |
| $5M2009-05 | Pobts | Joel Cutler |
| $5M2009-01-22 | FanSnap | Joel Cutler |
| $5M2009-01 | FanSnap | Joel Cutler |
| $8M2008-12-09 |  Roost | Joel Cutler |
| $8M2008-12 | Roost | Joel Cutler |
| $6M2008-11-24 | FanSnap | Joel Cutler |
| $6M2008-11 | FanSnap | Joel Cutler |
| $26M2008-08-26 | Jumptap | General Catalyst, Redpoint Ventures, Valhalla Ventures, Archer Venture Capital, Joel Cutler |
| $8M2008-08-15 | GameLogic | Joel Cutler |
| $8M2008-08 | GameLogic | Joel Cutler |
| $26M2008-08 | Jumptap | Joel Cutler |
| $14M2008-04-11 | Pobts | Jeremy Levine, Joel Cutler |
| $14M2008-04 | Pobts | Joel Cutler |
| $8M2008-03-28 | Reveal Imaging Technologies | Joel Cutler |
| $12M2008-03-28 | Reveal Imaging Technologies | Gabe Ling, Joel Cutler |
| $12M2008-03 | Reveal Imaging Technologies | Joel Cutler, Gabe Ling |
| $8M2008-03 | Reveal Imaging Technologies | Joel Cutler |
| $200M2007-12-01 |  Kayak | Robert Abbott, Joel Cutler |
| $200M2007-12 | KAYAK | Joel Cutler |
| $4M2007-06-18 | GameLogic | Joel Cutler |
| $4M2007-06 | GameLogic | Joel Cutler |
| $6M2007-01-01 | Roost | Joel Cutler |
| $6M2007-01 | Roost | Joel Cutler |
| $22M2006-10-04 | Jumptap | Joel Cutler |
| $22M2006-10 | Jumptap | Joel Cutler |
| $10M2006-09-01 | Pobts | Jeremy Levine, Joel Cutler |
| $10M2006-09 | Pobts | Joel Cutler |
| $18M2006-02-08 | GameLogic | Joel Cutler |
| $18M2006-02 | GameLogic | Joel Cutler |
| $100M2006-01-23 |  ITA Software | General Catalyst, Battery Ventures, Sequoia Capital, Sequoia, Spectrum Equity, Joel Cutler |
| $100M2006-01 | ITA Software | Joel Cutler |
| $17M2005-12-06 | Jumptap | Joel Cutler |
| $17M2005-12 | Jumptap | Joel Cutler |
| $4M2005-03-01 | Jumptap | Joel Cutler |
| $4M2005-03 | Jumptap | Joel Cutler |
| $5M2005-01-01 | Reveal Imaging Technologies | Gabe Ling, Joel Cutler |
| $5M2005-01 | Reveal Imaging Technologies | Joel Cutler, Gabe Ling |
| $7M2004-12-01 | Kayak | Joel Cutler |
| $7M2004-12 | KAYAK | Joel Cutler |
| $9M2004-01-14 | Kayak | Joel Cutler |
| $9M2004-01 | KAYAK | Joel Cutler |
| $1M2003-05-22 | Reveal Imaging Technologies | Joel Cutler |
| $1M2003-05 | Reveal Imaging Technologies | Joel Cutler |
| $7M2003-02-06 | GameLogic | Joel Cutler |
| $7M2003-02 | GameLogic | Joel Cutler |
| $2M2002-07-15 | GameLogic | Joel Cutler |
| $2M2002-07 | GameLogic | Joel Cutler |
