Episode 839 | The Journey Growing Help Scout to $35M ARR

**Rob Walling** (0:00)
Welcome back to another episode of Startups For the Rest of Us. I am your host, Rob Walling, and in this episode, I have the pleasure of interviewing Nick Francis, the co-founder of Help Scout. Help Scout has long been one of my favorite support tools. We used it back in the day at Drip. And when Nick and I recently met in person for the first time, I jumped at the chance to get him on the podcast. Nick is a bootstrapper at heart, but he and his co-founders did raise money with Help Scout, and they have grown it over 15 years to 35 million in ARR. It's a really interesting story with a lot of ups, downs and gutsy decisions. I think you're going to enjoy the conversation.
Before we dive in, a quick reminder that MicroConf Europe is happening in Reykjavik, Iceland from September 21st through the 23rd of 2026
We have an incredible lineup of speakers, some great excursions planned, and obviously we're all looking forward to getting in the same room with about 175 to 200 other like-minded founders. Ticket prices go up on July 2nd, so they're the cheapest they will ever be. And if you're thinking about bringing your team or your mastermind group, we're running a group discount right now. If you buy three or more tickets, you get 10% off. Maybe your co-founder or your CMO always wonders why you're so revved up after coming back from MicroConf. This is your chance to show them. Plus, getting everyone in the same room is much, much more valuable than another Zoom call. And you'll be in Iceland, so that doesn't hurt either. Come up and say hi to me if you wind up making it. You can head to microconfeurope.com to see the speaker line up, get all the details, and to grab your tickets before the price goes up. This event will sell out, so if you're thinking about going, go ahead and head to microconfeurope.com. And now, let's dive into my conversation with Nick.
Nick Francis, welcome to the show.

**Nick Francis** (1:57)
So happy to be here, Rob.

**Rob Walling** (1:58)
It's great to have you, man. We ran into each other at MicroConf, of all places, in Portland a couple months ago. And you came up and I was like, Nick Francis, this name is familiar. And you're like, I'm the co-founder of Help Scout. I was like, what? Like, you guys are awesome. Like, I love Help Scout. A bunch of tiny seed companies still use Help Scout. Bunch of people at MicroConf, I mean, Drip back in the day used Help Scout. It was really cool to have you.

**Nick Francis** (2:22)
I was so honored. It was great to show up at MicroConf and have such name recognition. Every time I talked to somebody, it was like, oh, Help Scout, it was really, really nice.

**Rob Walling** (2:32)
Yeah, that's cool. So we were chatting there and I realized I wanted to get you involved, assuming you wanted to, in this whole ecosystem we have. So you've since become a tiny seed mentor, maybe teasing something we haven't announced yet, but let's just say, loyal listeners, I may or may not have invited Nick to speak at a future MicroConf, and tell the story of Help Scout. And I wanted to have you on the show, to really live through the story, to go back through the painful memories and the beautiful ones as well, of the past, what, 15 years, I guess, of Help Scout.

**Nick Francis** (3:04)
Yeah, 15 years, but I'm such a big fan of what you are doing, the community that you've built. MicroConf has been a force of nature for so long. It was really great to be there with people, it's with kindred spirits, people with shared values.
I think that's a really special event.

**Rob Walling** (3:23)
Thank you. Appreciate that. It's definitely your people, right? I think of you as a founder who has that opinionated taste that I admire, you know, like Ben Chestnut of MailChamp, the Basecamp guys, these other founders who really, even Postmark.

**Nick Francis** (3:41)
Natalie and Chris. Yeah, they're legends.

**Rob Walling** (3:43)
Yeah, yeah. Wild bit, right? And it's this opinionated take on, I don't just want to build a company, but I want to do it in a certain way that I believe in. And for you, that was, I think of you mostly as a bootstrapper. I think of like Jason Cohen, to be honest, mostly as a bootstrapper, even though he's raised a kajillion dollar, he just has that mentality. He thinks like a capital efficient and you're one of the same, even though, as we're going to get to in your story, you raised $28 million in funding. So I just want to, I just want to start that off. Like as people are listening, it's like you are that bootstrap founder who has now gone down this path and I kind of want to hear about your thought process along the way. I think to kick us off, I have a nice little timeline here that producer Ron put together for me.