Jason sits down with the "Godfather of Saas," Jason Lemkin, to discuss everything from the SaaS (software as a service) industry to angel investing criteria, from Lemkin's current venture Saastr, to what the field has in store. We learn about the history of SaaS, why we owe a huge debt to Salesforce, and why so few enterprise customers “try before they buy.” The two Jasons further discuss Microsoft’s foray into SaaS, why “lockin” is a myth, the successes of -- and differences -- between Slack and HipChat, Lemkin’s SaaS investments (including Talkdesk, Algolia), why founders don’t make great VCs, Lemkin’s criteria for an investment (hint: the founder has to be better than him) and Lemkin’s advice on lifetime value to budding SaaS startups. Finally, the Jasons posit what would happen if Google or Microsoft came out with a free Slack competitor (protip: do not get arrogant about your engineers), the hurdles in monetizing a free product, why an acquisition might cost nothing for a big tech company, the mistake many companies made in 2008 and 2009, why choosing the celebrity investor isn’t always the best idea, the sheer volume of startups today -- and much more.
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0:00 - 3:44 Introduction/Welcome Jason Lemkin
3:45 - 6:03 What is SaaS?
6:04 - 7:24 Adobe and the Business Model of SaaS
7:25 - 8:50 Salesforce Started It All
8:51 - 10:44 Try Before They Buy
13:43 - 15:30 Microsoft and SaaS
15:31 - 18:45 Piracy, Marketing, Adobe, Materiality Threshold
18:46 - 21:17 Why is Slack so Special?
21:18 - 23:40 Zapier, LockIn
23:41 - 26:45 Slack vs. HipChat
28:36 - 30:37 Saastr
30:38 - 32:16 Conferences as a Pipeline
32:17 - 35:49 What to look for in angel investing
35:50 - 37:09 Founders aren’t the best VCs
37:10 - 41:50 Investment Criteria
41:51 - 43:51 Algolia
43:52 - 45:15 Zenefits
45:16 - 46:52 Box, Spending on Sales and Marketing
46:53 - 49:10 Lifetime Value Advice
49:11 - 52:07 Free Slack Competitor?
52:08 - 54:59 Sustaining the Projects at Big Companies
55:00 - 58:21 Entering a Space and Acquiring
58:22 - 1:02:24 MNA, SVP Deals
1:02:25 - 1:04:50 What does 2016 look like for unicorns?
1:04:51 - 1:07:11 Screwing up in ‘08 & ‘09
1:07:12 - 1:08:26 What It All Means for Startups
1:08:27 - 1:11:30 Choosing an Investor
1:11:31 - 1:14:50 Sheer Volume of Startups
1:14:51 - 1:17:38 ZenLearning, Working to Be Fundable
1:17:39 - 1:20:00 What’s Next for Lemkin?
1:20:01 - 1:25:25 Being an Angel Investor
1:25:26 - 1:36:36 Jason’s angel investing plans