Ed shares 28 years of lessons as an enterprise inception investor on The Peel Podcast
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Outline here:
Timestamps: 3:48 Evolution of early stage investing 5:11 Inception stage investing 10:32 Backing bold founders reinventing the enterprise stack 11:20 Repeatable ways to build enterprise businesses 12:04 The 5 P’s of early stage investing 14:12 Backing Guy Podjarny and Snyk 18:18 Knowing when to follow-on 19:18 The 3 Ch’s of a good board member 22:01 How Ed’s board role changes over time 24:20 Balancing founder friendly with returns 27:20 How to build customer relationships 30:24 Advice for closing customers 33:47 Creating the Seed category in 2009/10 37:31 boldstart’s $1m Fund 1 39:00 Why Ed didn’t join a large firm in 2012 39:55 boldstart’s $16.5m Fund 2 40:26 Why LPs passed on the first funds 43:11 Leading rounds in Kustomer, Snyk, BigID, and Block Daemon in Fund 3 47:09 Why $112m Fund 4 was the hardest to raise 50:52 Ed’s approach to LP fundraising 55:12 Inside Meta’s acquisition of Kustomer and sale back to the founders 59:52 Backing Rahul from Superhuman a 2nd time 1:00:52 The different GTM playbooks 1:02:20 Importance of contract size and time to close 1:05:07 Why AI makes security more important 1:06:11 When to switch from founder-led sales 1:07:46 Backing ProtectAI after a conference 1:08:28 Balancing in and outbound sales 1:09:55 Winners and losers in AI 1:15:26 Building the boldstart team 1:19:33 Lessons being an interim CEO 1:22:18 How ZIRP pulled revenue forward 1:29:08 The death of high growth software 1:32:58 Identifying startup opportunities incumbents won’t crush 1:35:00 Second order effects of AI 1:36:46 Using “Intuitive TAM” to size new markets 1:38:04 Investing before there’s a market map 1:38:57 Balancing family, fitness, and career