On the podcast, we talk with Ron about the magic of consumer subscriptions, experimenting with freemium strategies, and how private equity isn’t always as bad as you’ve been led to believe.

Our guest today is Ron Schneidermann, CEO at AllTrails, the ultimate guide for outdoor adventures. AllTrails was early to the consumer subscription space, launching a $3/month premium tier way back in 2012. Ron joined as CMO and COO in 2015, and then took over as CEO in 2019, helping to grow AllTrails to over 1 million subscribers and tens of millions of active users worldwide.

In this episode, you’ll learn:

How to refine and optimize your freemium strategy
Two things you need to keep an eye on as a founder
The pros & cons of outside funding vs. organic growth
How Ron fast-tracked AllTrails’ profitability

Links & Resources

Ron Schneidermann’s Links

Ron Schneidermann’s LinkedIn page
AllTrails Celebrates 1 Million Paid Subscribers! (January press release)
AllTrails’ website
AllTrails is hiring
Follow AllTrails on Twitter

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Episode Transcript

00:00:00 David:

Our guest today is Ron Schneidermann, CEO at AllTrails, the ultimate guide for outdoor adventures, AllTrails was early to the consumer subscription space, launching a $3 per month premium tier, way back in 2012. Ron joined as CMO and COO in 2015, and then took over as CEO in 2019, helping to grow AllTrails to over 1 million subscribers and tens of millions of active users world.

On the podcast, we talk with Ron about the magic of consumer subscriptions, experimenting with freemium strategies, and how private equity isn’t always as bad as you’ve been led to believe.

Hey, Ron! Welcome to the podcast.

00:00:59 Ron:

Thanks for having me.

00:01:00 David:

Yeah. Really looking forward to the chat today. I wanted to kick it off, and most people know what AllTrails is, and it’s a fantastic brand. It kind of tells you what it is right there on the tin. What’s your pitch? We’re in 2021, post pandemic.

Give us the short version of what AllTrails is. What does it mean?

00:01:21 Ron:

Yeah. So AllTrails is a free app and website that helps you find trails all over the globe, so you can spend more time enjoying the outdoors, and spending time in nature.

00:01:34 David:

That’s awesome.

00:01:35 Jacob:

That’s a very nice mission. That’s way more beautiful than helping developers make more money. Both are important, but I can smell that. It smells, “piney” and I like it.

00:01:46 David:

Yeah, it smells like the Colorado forest. I haven’t been hiking forever, and doing all the research to chat with you today was like, oh man, I need to go hiking more.

00:01:55 Ron:

I heard there’s a great app for that.

00:01:57 David:

I heard that.

So, I did want to also ask about your journey to AllTrails. You got there fairly early, and then grew in, and you’re now CEO. Tell me, off the bat, what led you to AllTrails way back in 2015 when it was just six people?

00:02:20 Ron:

Yeah. To answer that I’m going to go a little bit further back in time. My first job right after college was at Accenture, at a global management consulting firm. It was great. A good jumping off point, and I learned a ton. I didn’t know anything going into that job. You know, you get the rubber stamp and it opens doors.

By the end of my third year there, I kind of had a realization. Epifany is a little too strong a word, but I just kind kinda realized I can’t take a job just for money again. The amount of time and energy that I was putting into it, and the lack of work-life balance, it really made me rethink who I want to be. Who does working Ron want to be?

So, I was able to parlay that Accenture job into a biz dev role over at Hotwire, an online travel company. That was really where it opened my eyes. Like, I am so much happier, and I am honestly so much better when I’m working at something that I’m just personally passionate about.

That guiding principle has really held through throughout my career trajectory. From Hotwire, I want to do my own startup in the ski space. I love to ski. So, I did that for nine years. It was a ton of fun. Then I was over at Yelp, doing growth for a bit. I love finding non-chain restaurants, and supporting mom and pop businesses, and stuff. I live in Yelp, so that was great.

Then, when the opportunity for AllTrails presented itself, it was just kind of a no-brainer. Of course I’m going to take this.

I’ll say this to you, one little addendum, one of the things I learned along the way, too. I am not a zero to one guy. That is not when I am at my best. It just causes me stress and anxiety, and just, figuring out how to keep the lights on for another day.

So, again, knowing kind of that sense of self knowing. Like, alright, I’m best at B to C. I’m at my best when I’m using products I personally want to use and like talking about. I like hypergrowth, and I think that’s probably my sweet spot.

So, it starts to all align when AllTrials showed up.

00:04:34 David:

Yeah. And then how did that go from? You joined the company as COO, right? And then, what was the progression inside the company to eventually taking over as CEO?

00:04:45 Ron:

Yeah. So if you want to demo and COO, I dunno why I really wanted to have both, like, I didn’t want to just be CMO in a vacuum, but not have any ownership or agency over kind of team composition and strategy and stuff. So I thought that it was really. Really important. And when you’re a six person company, it’s pretty easy to grab titles.

It’s not like how to take it from anyone.

00:05:08 Jacob:

I was going to ask, like, I mean, it’s, it’s not like you see this a lot where it’s like a six person company and they had like five C-levels and you’re like, okay. Yeah, sure. Like, like my title, for example. But like, I’m kind of curious, like, you know, you like your background, you founded a company, like you were like a real CX whatever.

Right? Like it’s not like it was fake. So how did, how did that, how did you go as like an executive, like choo...

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