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

Startups For the Rest of Us

Rob Walling

Management, Entrepreneurship, Business, Marketing

4.8 • 792 Ratings

🗓️ 8 October 2024

⏱️ 35 minutes

🔗️ Recording | iTunes | RSS

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Summary

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! Subscribe & Review: iTunes | Spotify

Transcript

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0:00.0	Welcome to this episode of Startups of the Rest of Us. I'm Rob Walling, and this week I talk with
0:04.6	Ian Lansman, the founder of HelpSpot. Ian has been bootstrapping for almost 20 years,
0:10.6	and he started with on-prem software, and then after about 10 years, launched a SaaS version.
0:16.5	Ian and I have known each other almost that same 20 years from back in the days of Joel on Software's Business of Software forums.
0:24.6	And over the years, Ian has started a few of his own podcasts, as well as spoken at MicroConf.
0:29.5	I believe, if I were to guess, it was probably around 2014 or 15.
0:33.5	So it's a great conversation because Ian and I have history.
0:37.0	I think we were able to pull out some really interesting bits about why he's bootstrapped for 20 years,
0:41.5	why he hasn't sold and moved on to his next act, how he thinks AI is going to impact the customer service and support space.
0:51.5	And if you stick around to the end, you'll get to hear the company name
0:55.4	that is most often confused with HelpSpot,
0:58.8	and it wasn't the one that I thought.
1:00.8	So with that, let's dive into our conversation.
1:10.2	Ian Lansman, welcome to this show.
1:12.4	Thanks for having me on.
1:13.9	It's great to be here.
1:14.8	Cannot believe you have not been on this show.
1:17.9	You're like OG bootstrapper.
1:19.9	Somebody on Twitter, right, reached out and said, I should come on here.
1:22.0	And I was like, man, I think I've been on there.
1:23.6	And then, like, I surged.
1:25.0	And I was like, man, I haven't been on there.
	...

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