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Podcast Episode

How This Bootstrapped Help Desk Software has Lasted over 10 Years Against VC Backed Competitors

The Grow and Convert Marketing Show··17 July 2026·59 min

About this episode

In our latest episode, we interview founder Ian Landsman about how he started the help desk software Helpspot back in the early 2000s and how he's lasted 15+ years against funded big name players like Zendesk, HelpScout, and more.We get into the details about what he did in the early days to launch his company, why he never really had a focus on marketing until recently, and we share some of the rankings that we've been able to generate for their business in an extremely competitive category.Sections: 0:00 Intro 1:13 The founding story of Helpspot 5:26 Funny story about software development 7:49 Laravel 8:48 How Helpspot was funded 9:35 Pre-SaaS 11:56 How Helpspot launched 12:56 Early SEO 15:39 Enter the competitors- Zendesk, etc. 18:27 Team size 20:29 Why Helpspot never invested in marketing 25:26 Difference between VC funded and bootstrapped help desk software 29:15 Did you ever think about selling your business? 31:43 Marketing and positioning 35:23 Why invest in SEO 40:37 Results from G&C 47:10 Attribution of leads to SEO/Content 53:52 Helpspot 2023 and beyond