Ian Landsman
Founder of HelpSpot, a bootstrapped help desk software company he has run since 2005 with no outside funding.
“On my order of things that are going to put me out of business, Finn and similar, number one, we get hacked and just something we can't handle and fix. Number two, people vibe coding their own shit, like way, way down below those top two.”
Mostly Technical · Bootstrapped & Indie SaaS · November 2026
Context
Closing out a long segment on a wave of security incidents, Ian ranks the risks to his own SaaS business. It cuts against the 'AI is eating SaaS' story the hosts argued about earlier in the episode.
Transcript
And it's going to get worse.
Railway, North Flank, Trigger.dev, Ubuntu, Chrome. And that's in like the past three days. That's over the weekend. Yeah.
And like, we're only getting worse. Like, I'm way more worried. Again, on my order of things that are going to put me out of business, Finn and similar, number one, we get hacked and just something we can't handle and fix. Number two, people vibe coding their own shit, like way, way down below those top two. Like, because, yeah, the security stuff is crazy. Like, it's scary out there. Like, it is so
scary out there. Yeah.
I feel bad. Every time I
see a CVE, I like put it in the Laravel channel and I'm like, oh, this looks bad. Good luck, guys. Yeah. But like, I just can't, like, we have a whole team responsible for that. And I, I think it's, I do think it's like bad for the open web that I'm, I am such a smart boy and I'm like, I can't, I…
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