# Ed shares 28 years of lessons as an enterprise inception investor on The Peel Podcast - boldstart ventures [← News](/news/) News · 2024-06-20 # Ed shares 28 years of lessons as an enterprise inception investor on The Peel Podcast ![Ed shares 28 years of lessons as an enterprise inception investor on The Peel Podcast](/wp-content/uploads/2024/06/049-ed-sim-boldstart-ventures-cover-art.jpeg) Apple Podcasts Spotify > 🎧🍌 New [@ThePeelPod](https://twitter.com/ThePeelPod?ref_src=twsrc%5Etfw) with [@edsim](https://twitter.com/edsim?ref_src=twsrc%5Etfw) > > Ed’s the founder of [@boldstartvc](https://twitter.com/Boldstartvc?ref_src=twsrc%5Etfw), backing bold founders reinventing the enterprise stack at the inception stage. > > Our 100+ minute convo covers key moments building boldstart, from its first $1m fund in 2010 to over $850m in AUM today. Ed takes… [pic.twitter.com/3YEsdSSsLQ](https://t.co/3YEsdSSsLQ) > > — Turner Novak 🍌🧢 (@TurnerNovak) [June 20, 2024](https://twitter.com/TurnerNovak/status/1803788927305728036?ref_src=twsrc%5Etfw) Outline here: Timestamps: [3:48](https://x.com/TurnerNovak/status/1803788927305728036?t=228) Evolution of early stage investing [5:11](https://x.com/TurnerNovak/status/1803788927305728036?t=311) Inception stage investing [10:32](https://x.com/TurnerNovak/status/1803788927305728036?t=632) Backing bold founders reinventing the enterprise stack [11:20](https://x.com/TurnerNovak/status/1803788927305728036?t=680) Repeatable ways to build enterprise businesses [12:04](https://x.com/TurnerNovak/status/1803788927305728036?t=724) The 5 P’s of early stage investing [14:12](https://x.com/TurnerNovak/status/1803788927305728036?t=852) Backing Guy Podjarny and Snyk [18:18](https://x.com/TurnerNovak/status/1803788927305728036?t=1098) Knowing when to follow-on [19:18](https://x.com/TurnerNovak/status/1803788927305728036?t=1158) The 3 Ch’s of a good board member [22:01](https://x.com/TurnerNovak/status/1803788927305728036?t=1321) How Ed’s board role changes over time [24:20](https://x.com/TurnerNovak/status/1803788927305728036?t=1460) Balancing founder friendly with returns [27:20](https://x.com/TurnerNovak/status/1803788927305728036?t=1640) How to build customer relationships [30:24](https://x.com/TurnerNovak/status/1803788927305728036?t=1824) Advice for closing customers [33:47](https://x.com/TurnerNovak/status/1803788927305728036?t=2027) Creating the Seed category in 2009/10 [37:31](https://x.com/TurnerNovak/status/1803788927305728036?t=2251) boldstart’s $1m Fund 1 [39:00](https://x.com/TurnerNovak/status/1803788927305728036?t=2340) Why Ed didn’t join a large firm in 2012 [39:55](https://x.com/TurnerNovak/status/1803788927305728036?t=2395) boldstart’s $16.5m Fund 2 [40:26](https://x.com/TurnerNovak/status/1803788927305728036?t=2426) Why LPs passed on the first funds [43:11](https://x.com/TurnerNovak/status/1803788927305728036?t=2591) Leading rounds in Kustomer, Snyk, BigID, and Block Daemon in Fund 3 [47:09](https://x.com/TurnerNovak/status/1803788927305728036?t=2829) Why $112m Fund 4 was the hardest to raise [50:52](https://x.com/TurnerNovak/status/1803788927305728036?t=3052) Ed’s approach to LP fundraising [55:12](https://x.com/TurnerNovak/status/1803788927305728036?t=3312) Inside Meta’s acquisition of Kustomer and sale back to the founders [59:52](https://x.com/TurnerNovak/status/1803788927305728036?t=3592) Backing Rahul from Superhuman a 2nd time [1:00:52](https://x.com/TurnerNovak/status/1803788927305728036?t=3652) The different GTM playbooks [1:02:20](https://x.com/TurnerNovak/status/1803788927305728036?t=3740) Importance of contract size and time to close [1:05:07](https://x.com/TurnerNovak/status/1803788927305728036?t=3907) Why AI makes security more important [1:06:11](https://x.com/TurnerNovak/status/1803788927305728036?t=3971) When to switch from founder-led sales [1:07:46](https://x.com/TurnerNovak/status/1803788927305728036?t=4066) Backing ProtectAI after a conference [1:08:28](https://x.com/TurnerNovak/status/1803788927305728036?t=4108) Balancing in and outbound sales [1:09:55](https://x.com/TurnerNovak/status/1803788927305728036?t=4195) Winners and losers in AI [1:15:26](https://x.com/TurnerNovak/status/1803788927305728036?t=4526) Building the boldstart team [1:19:33](https://x.com/TurnerNovak/status/1803788927305728036?t=4773) Lessons being an interim CEO [1:22:18](https://x.com/TurnerNovak/status/1803788927305728036?t=4938) How ZIRP pulled revenue forward [1:29:08](https://x.com/TurnerNovak/status/1803788927305728036?t=5348) The death of high growth software [1:32:58](https://x.com/TurnerNovak/status/1803788927305728036?t=5578) Identifying startup opportunities incumbents won’t crush [1:35:00](https://x.com/TurnerNovak/status/1803788927305728036?t=5700) Second order effects of AI [1:36:46](https://x.com/TurnerNovak/status/1803788927305728036?t=5806) Using “Intuitive TAM” to size new markets [1:38:04](https://x.com/TurnerNovak/status/1803788927305728036?t=5884) Investing before there’s a market map [1:38:57](https://x.com/TurnerNovak/status/1803788927305728036?t=5937) Balancing family, fitness, and career [← Explore more](/news/) --- Source page: /news/ed-shares-28-years-of-lessons-as-an-enterprise-inception-investor-on-the-peel-podcast/