Menu
Sign In Search Podcasts Charts People & Topics Add Podcast API Blog Pricing

Ian Landsman

๐Ÿ‘ค Speaker
190 total appearances

Appearances Over Time

Podcast Appearances

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

And so generally, most companies are going to pay that support. And they did. And so that worked out good long term. But yeah, absolutely. It wasn't like, oh, man, this is monthly. Four grand a month was definitely not that. Yeah.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

And so generally, most companies are going to pay that support. And they did. And so that worked out good long term. But yeah, absolutely. It wasn't like, oh, man, this is monthly. Four grand a month was definitely not that. Yeah.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Oh, geez. I think it was... It was either, I think it was like 150 a license.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Oh, geez. I think it was... It was either, I think it was like 150 a license.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, something like that. That's pretty good. Sounds right.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, something like that. That's pretty good. Sounds right.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, I was happy. I was like, whoa. And then we mined that mailing list. And so the second month was like $1,000 or something crazy. And it was a little nerve-wracking there. And then it went up after that and just like kept going up.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, I was happy. I was like, whoa. And then we mined that mailing list. And so the second month was like $1,000 or something crazy. And it was a little nerve-wracking there. And then it went up after that and just like kept going up.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Keeps you in business.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Keeps you in business.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, well, I think that's true. Like with the invoicing software, it's like, it's a little more like, hey, we use it, it works. Yeah, well, maybe with some of us, sometime we'll pay him his renewal, but we don't really care that much. It's operational, right? It's like, if you can get to that next layer of like, no, we have like $2 million in payroll using this software.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, well, I think that's true. Like with the invoicing software, it's like, it's a little more like, hey, we use it, it works. Yeah, well, maybe with some of us, sometime we'll pay him his renewal, but we don't really care that much. It's operational, right? It's like, if you can get to that next layer of like, no, we have like $2 million in payroll using this software.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

And like, now we're taking this big risk. If we're down for a day, it's like, a big problem and we're losing money, right? More directly. And so I think when you're thinking about the kind of business to get into, there are advantages to that kind of thing where it's a product that people use very heavily, very competitive nowadays too.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

And like, now we're taking this big risk. If we're down for a day, it's like, a big problem and we're losing money, right? More directly. And so I think when you're thinking about the kind of business to get into, there are advantages to that kind of thing where it's a product that people use very heavily, very competitive nowadays too.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

I think it was like really a couple of different things. Definitely when I launched, I knew about SaaS and made the decision to not make it SaaS because I didn't know anything about running servers. There was no money to hire somebody else to run servers. And so I just feel like that wouldn't have ultimately worked out very well.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

I think it was like really a couple of different things. Definitely when I launched, I knew about SaaS and made the decision to not make it SaaS because I didn't know anything about running servers. There was no money to hire somebody else to run servers. And so I just feel like that wouldn't have ultimately worked out very well.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

So it was on premise and then was kind of going along and it was busy and it was fine. And the big... obviously when I took one notice in terms of direct competition was you had like Zendesk, which I think was maybe like 2008 ish something in there. And it's like, oh, okay. Like this is really becoming a thing now.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

So it was on premise and then was kind of going along and it was busy and it was fine. And the big... obviously when I took one notice in terms of direct competition was you had like Zendesk, which I think was maybe like 2008 ish something in there. And it's like, oh, okay. Like this is really becoming a thing now.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

So I should probably start thinking about more, but we did even before Zendesk earlier on have a partnership with a hosting company and they ran the hosted version of help spot for people. And so it was a separate relationship with them. It's like,

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

So I should probably start thinking about more, but we did even before Zendesk earlier on have a partnership with a hosting company and they ran the hosted version of help spot for people. And so it was a separate relationship with them. It's like,