With a few dozen software exits under his belt (including Box, Square, Mulesoft & JFrog), nobody knows enterprise investing like Sapphire Ventures’ President + PartnerJai Das. Likewise, Floodgate co-founder + Partner Mike Maples Jr. is often credited with pioneering seed investing as we know it, with names like Twitter, Twitch and Lyft in his portfolio. Together, they join Nick Chirls, GP at Asylum Ventures, and Beezer Clarkson, LP at Sapphire Partners, to share how they pick winners at their respective stages. What does it take to spot someone who sees the future before it’s here? How do inflection points like AI impact an investor’s thesis? And are there more opportunities in the market for VCs today? Plus, Jai and Mike discuss the one throughline from seed to growth to lead to a successful exit: the management team.

Learn more about Sapphire Partners: sapphireventures.com/sapphire-partners

Learn more about OpenLP: openlp.vc

Learn more about Asylum Ventures: asylum.vc

Learn more about Sapphire Ventures: sapphireventures.com

Learn more about Floodgate: floodgate.com

Subscribe to the OpenLP newsletter for a monthly roundup of the latest venture insights, including the newest Origins episodes, delivered straight to your inbox.

CHAPTERS:

0:00-Introduction & the Burning Question4:08-Intro to Sapphire Ventures

6:02-Intro to Floodgate7:56-Setting the Stage at Seed

10:30-Inflection Points: We're Going Through a Sea Change of Mass Cognition

13:43-What’s Happening at the Growth Stage

15:17-More Choice in the Market

16:10-Importance of Management Team

17:44-Mike’s New Book “Pattern Breakers”

23:09-The Three Things Floodgate Looks for in a Founder

25:25-Founder Future Fit & Pivots

27:56-In Enterprise Software, You Don’t Always Have to Build a New Category29:52-AI: Over-Valued? Under-Valued?

32:50-Is There Anything Left in AI Non-Consensus?

34:37-How Sapphire Approaches GenAI Investing

37:31-The Exit Market Today

44:10-How to Approach Founder Liquidity

A look at what’s to come on a brand new season of Origins, where we’ll dive into the VC ecosystem with the people who know it best, to learn how the people behind the capital really make decisions.

Learn more about Sapphire Partners: https://sapphireventures.com/sapphire-partners/

Learn more about Asylum Ventures: asylum.vc

Nick Chirls, GP at Asylum Ventures, and Beezer Clarkson, LP at Sapphire Partners, go inside their recent conversation with Alt Capital’s Jack Altman to answer their burning question: What does the journey look like from VC-backed founder to angel investor to institutional VC? How does one successfully jump from investing their own capital to taking on LP dollars? Where is Jack comfortable taking bigger bets? Plus, the two of them go in-depth for the very first time on Nick’s new firm, Asylum Ventures.

Learn more about Sapphire Partners: https://sapphireventures.com/sapphire-partners/

Learn more about OpenLP: https://openlp.sapphireventures.com/

Learn more about Asylum Ventures: asylum.vc

Learn more about Alt Capital: https://www.altcap.com/

Subscribe to the OpenLP newsletter for a monthly roundup of the latest venture insights, including the newest Origins episodes, delivered straight to your inbox.

Jack Altman of Alt Capital has led quite a life in Silicon Valley. He’s gone from angel investing to founding a venture-backed company (HR platform Lattice), back to angel investing today, taking on outside capital as an institutional investor at Alt Capital. Jack sits down with Nick Chirls, GP at Asylum Ventures & Beezer Clarkson, LP at Sapphire Partners, to discuss learnings from his impressive career arc, including how to build a reputation by avoiding zero sum games, making decisions quickly as a founder, the differences in investing your own money and someone else’s, how to build a track record as an angel, and being a generalist both inside and out of the office. Plus, having just welcomed his third child into the family, Jack discusses the importance of ruthless prioritization - how to say no to the low value-add dinners and meetings if it means you get to be home for bedtime.

Learn more about Sapphire Partners: https://sapphireventures.com/sapphire-partners/

Learn more about OpenLP: https://openlp.sapphireventures.com/

Learn more about Asylum Ventures: asylum.vc

Learn more about Alt Capital: https://www.altcap.com/

Subscribe to the OpenLP newsletter for a monthly roundup of the latest venture insights, including the newest Origins episodes, delivered straight to your inbox.

CHAPTERS:

00:00-Introduction

02:59-Nick’s new fund, Asylum Ventures, is Live!

07:22-The Burning Question

11:02-Jack Altman Introduction

12:55-Ruthless prioritization: Balancing Work & Family

16:40-The Best Idea You Say No To

19:21-Working with a Wide Scope of Founders

22:07-Building a Reputation in Venture

25:03-Venture is Noisy: Speak Softly but Carry a Big Stick

27:52-The Other Altman

30:42-From Founder to Angel to Institutional Investor

38:11-Fundraising Strategy

42:10-Investing Your Own Money vs LP Capital

45:52-Outro

Nick & Beezer go inside their recent conversation with Jason Shuman and Will Quist to discuss the right way to be a contrarian investor, how to do no harm as a VC, and dive into the answer to their burning question: do VCs actually add value?

Learn more about Sapphire Partners: https://sapphireventures.com/sapphire-partners/

Learn more about Notation Capital: https://notation.vc/

Learn more about Primary: https://www.primary.vc/

Learn more about Slow Ventures: https://slow.co/

What do Primary GP Jason Shuman and Slow Ventures Partner Will Quist have in common? At first glance, not much, given how differently their firms approach firm building and VC "platforms." At Primary, their Impact team outnumbers investors 2:1, while Slow consists of 3 GPs, and 3 GPs only. But in a surprising twist, they agree on more than one would expect.

They both see non-consensus investing as carrying big risk but also big opportunity. They are both seed investors and their respective firms go to market in very different ways. They sit down with co-hosts Nick Chirls, GP at Notation Capital & Beezer Clarkson, LP at Sapphire Partners, to talk about zigging when the market zags, identifying truly disruptive companies on day zero, and how much impact VCs actually have on the companies they partner with.

Learn more about co-host Beezer and her firm at Sapphire Partners: https://sapphireventures.com/sapphire-partners/

Learn more about Notation Capital: https://notation.vc/

Learn more about Primary: https://www.primary.vc/

Learn more about Slow Ventures: https://slow.co/

Learn more about OpenLP: https://openlp.sapphireventures.com/

Subscribe to the OpenLP newsletter for a monthly roundup of the latest venture insights, including the newest Origins episodes, delivered straight to your inbox.

Chapters:

00:00-Introduction & The Burning Question

06:06-Will & Jason Intros

09:13-Defining the S Curve

11:06-Positioning Your Firm to Win

15:08-Identifying Winners on Day Zero

18:31-Being Non-Consensus and Right

25:46-What is the Value Add of VCs?

32:43-Setting KPIs

35:36-”You Sell Something”

38:30-Outro

Joanna Rupp, Managing Director of Private Equity at the University of Chicago, sits down with Nick & Beezer to shine a light on the often opaque world of endowments, including what separates an endowment from a foundation, how they consider small funds v. big funds and the fallout from an avalanche of capital being thrown at VCs. Then (announcement!) Joanna and Beezer evaluate Nick’s new venture fund - the key pieces of diligence, what he needs to prove in the next few years for another investment, how to build a relationship with his LPs, and more.

Learn more about Sapphire Partners: https://sapphireventures.com/sapphire-partners/

Learn more about Notation Capital: https://notation.vc/

Visit the University of Chicago’s Endowment’s website: https://investments.uchicago.edu/

Read Ted Seides’s blog post: https://www.capitalallocators.com/the-investment-office-playbook-what-managers-dont-see/dinvestors.com/blog/the-three-body-problem-finding-the-new-stable-points-in-venture-capital

Visit OpenLP as your go-to resource for LP thought leadership: https://openlp.sapphireventures.com/https://www.linkedin.com/company/openlp/

https://x.com/open_lp

Nick and Beezer sit down with Frank Rotman, a founding partner and CIO at QED Investors to talk about his early days as the chief credit officer of Capital One, the fundamental flaw in the way founders and investors have been funding startups, the purpose associates serve and how those associates can better their skills, and how VCs can avoid being left in the exhaust of larger firms.

Learn more about Sapphire Partners: https://sapphireventures.com/sapphire-partners/

Learn more about Notation Capital: https://notation.vc/

Visit QED Investors’ website: https://www.qedinvestors.com/

Read Frank Rotman’s post on the Three Body Problem: https://www.qedinvestors.com/blog/the-three-body-problem-finding-the-new-stable-points-in-venture-capital