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Rob Walling

πŸ‘€ Speaker
4164 total appearances

Appearances Over Time

Podcast Appearances

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

And longtime listener Chaz Yoon hired a senior developer from Lemon.io and said his hire, quote, definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations. Chaz said he'd definitely use Lemon.io again when he's looking for a senior level engineer.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

To learn more and get a 15% discount on your first four weeks of working with a developer, head to Lemon.io slash startups. That's Lemon.io slash startups. So I want to switch it up a little bit and ask you about the, I'd say the unorthodox way that you came about being a co-founder of this company. So your co-founder, John, built it and got a first big customer in 2020.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

And then you came in, it was either 2023 or 2024, last year, and you bought into the business, right? And he's now a minority owner now. Tiny Seed obviously owns our percentage, but tell us a little bit about how that went down and like what, who came up with the idea? Cause it's, again, it's unorthodox. And I like to tell stories on this show to give people an idea of, oh, that's possible.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

I didn't know you could do that. Right. And that when I heard your story, I was like, huh, yeah, it's an interesting, interesting way. So walk us through what happened.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

So did you and John know each other before this? No, we did not. Okay, how did you find each other?

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

Ah, very nice. I didn't know that Quietlight would do majority but not full acquisitions.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

As we move towards wrapping up, I have a question for you that I'd like to ask of a lot of guests that come on the show. And it's in your experience running, growing, building this business, what has been the hardest thing about it? And you can either say overall, like, ooh, it's been X, Y, Z challenge. Or if there's a moment where you were like, this is so f***ed. I'm not having fun at all.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

You can also just go to a moment.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

The uncertainty. Yeah. And it's not just the money. It's your opportunity cost, man. Like you could get a job working for a company in the Bay Area and make lots of money. And yet you are basically, you know, I'm guessing taking a below market salary as most of us do and just trying to figure it out. And that is a real it's a gamble.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

You know, kind of the traditional, like maybe Silicon Valley or YC founder is like a 23-year-old founder doing it at a garage, you know, or having a this and that. And there's a reason for that stereotype. Most of the microconf, tiny seed, startups for the rest of this ecosystem tends to skew a little older, let's say 30s and 40s, some folks in their 50s.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

But the further you get on and the more, you know, you're making 350 grand a year as an engineer, senior engineer for Facebook or something. It becomes really hard to leave that for the uncertainty of a startup. And I think it is, I mean, it's just one of the big concerns that folks have.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

Yeah. Yeah, being alone in the uncertainty is even harder. And being alone and having a spouse and or a family in the uncertainty. And it's like, well, I'm going to spend all these nights and weekends for, you know, at least you're able to do a full time, hopefully mostly during the day. But the bootstrap, you know, I bootstrapped five companies and then raised money for tiny seed.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

But four of them I did effectively nights and weekends. And it was not fun because I had young kids and I was like telling Sherry, my wife, like, so, you know, all this time I'm putting into this thing, you know, by the time I was on the second one, the first one had made enough money that it was like, OK, I'm going to do this again. And I kind of know what I'm doing now and now, Fred.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

But the first one was a real tough sell when our friends were like, let's go to happy hour. And I'm like, I would love to. But or I'd go and I'd leave early because I was like, dude, I got to get home and write some code on this thing. These are the trade-offs, the unseen trade-offs of entrepreneurship, but specifically bootstrapping of any kind is just a lot of grinding hours.

Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem

Andy Kim, thanks so much for joining me on the show. If folks want to keep up with you on ex-Twitter, you are at trottohq. And of course, if folks want to check out Trotto, it's trot.to. Thanks again. Thanks. Thanks again to Andy for coming on the show. And thank you for listening this week and every week. This is Rob Walling signing off from episode 739.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

Welcome back to Startups for the Rest of Us. As always, I'm your host, Rob Walling. In this episode, I'm going to be answering later stage questions. I received a ton of good questions on ex-Twitter a month or so ago when I did a call for them. And I had gotten a little weary of answering the same questions about idea validation and early stage stuff.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

Welcome back to Startups for the Rest of Us. As always, I'm your host, Rob Walling. In this episode, I'm going to be answering later stage questions. I received a ton of good questions on ex-Twitter a month or so ago when I did a call for them. And I had gotten a little weary of answering the same questions about idea validation and early stage stuff.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

So these are all folks doing six or seven figures in ARR that have questions ranging from regrets for things you didn't delegate, how to decide to DIY versus hiring a growth agency, deciding whether a customer type is worth selling to or targeting, and more. Before we dive into the episode... My new course, the SaaS Launchpad, has been live for a few weeks. It has been receiving rave reviews.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

So these are all folks doing six or seven figures in ARR that have questions ranging from regrets for things you didn't delegate, how to decide to DIY versus hiring a growth agency, deciding whether a customer type is worth selling to or targeting, and more. Before we dive into the episode... My new course, the SaaS Launchpad, has been live for a few weeks. It has been receiving rave reviews.

Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

SaaSLaunchpad.co if you want to check it out. It's for the earliest stage SaaS founders. So if you're looking for an idea, if you want to vet an idea to validate it, if you want to build a launch list, if you want to build an MVP, launch your product. This is the course for you. It is the best course I've ever put together. And it's really the first course I've built in about 14 years.