Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Startups For the Rest of Us

In episode 734, Rob Walling interviews Ian Landsman, founder of HelpSpot, about his 20-year bootstrapper journey. They discuss Ian's transition from on-prem software to SaaS, the challenges and benefits of each, and the early days of building the business. They wrap up by discussing the potential impact of AI on the customer service industry.

Topics we cover:

• 1:11 – Ian, the OG bootstrapper
• 2:22 – Benefits of on-prem software in 2024
• 5:46 – Slow, steady, profitable growth through the years
• 9:20 – Embracing a risky start
• 14:11 – Getting early awareness
• 18:52 – Transitioning to SaaS
• 26:37 – Laravel raises $57M
• 28:59 – AI impact on customer service

Links from the Show:

• The SaaS Playbook
• TinySeed
• Ian Landsman (@ianlandsman) | X
• HelpSpot (@helpspot) | X
• HelpSpot
• Podscan
• Accel invests $57M into Laravel Products & Open-Source Framework
• Mostly Technical

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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