CEO @ AllTrails: Ron Schneidermann – Leading a Small Team to Enormous Growth

Ron Schneidermann is the CEO of Alltrails, where he spent the past six years helping grow the company, which is now one of the top five health and fitness apps in the Apple App Store and Google Play Store. Before joining Alltrails, Ron led growth teams at Yelp and co-founded Liftopia, the global leader of ski lift ticket bookings.

Ron shares that the two most important things for any company are momentum and culture. If you lose either of them, they are impossible to rebuild. Have belief in your business model and look at the advantages in context. When you cannot control certain aspects of the funnel, let full-funnel growth (across all stages) be the central driver of your business.

If your app is “content-centered,” your data sets hold the power to convert and retain users. First, focus on improving the quality of data you can provide to your audience. Don’t get attached to results because any growth experiment can fail. Instead, focus on learning from successful and failed experiments. Find and monitor feedback loops based on what your users respond to. The key to growth is to keep adapting as your audience adapts because they are the chief driver of your business growth.

Re-engagement via push notification may put you at risk of annoying your customers. People may forget that they have the app installed, so it’s always better to focus on outside-the-app strategies such as SEO, personalized content, and reminders via emails to drive re-engagement through deep links into the app.

Try not to depend on one platform because it can make a huge dent in your growth charts if the platform changes. Try to own your channels of growth as much as possible.

Daily and sometimes even weekly metrics may be distracting. Monthly metrics provide a more accurate view of your audience’s changing consumption habits and are a healthier way to monitor growth.

Ron shares that to maintain culture momentum during growth, your company’s senior leadership has to be the culture vanguard and train the rest of the leadership across the org. This becomes easier if people in your organization have a personal connection to your mission and stay longer.

Ron’s final advice: be honest with yourself when making important decisions because you will be proud of the practical decisions you make and reactionary paths you avoid after you retire. Having a personal set of core values helps identify opportunities and enjoy the process of executing them.

Mada: Hi, everyone. We are thrilled to have our next guest today. Ron Schneidermann, who is currently the CEO of Alltrails, where he spent the past six years helping grow the company, which is now one of the top five health and fitness apps in the app store and Google play. Before joining Alltrails, Ron led the growth teams at Yelp and co-founded Tapia at the global leader of ticket bookings.
Welcome to the show Iran. I’m so excited to have you.
Ron: Thanks for having
Mada: me. I am a, an avid user of Alltrails. I didn’t use to be, I’m probably like a year old as a new user, and it’s been really helpful for me throughout the pandemic. I started taking hiking very seriously. I have a dog it’s really hard to like, figure out anywhere else.
Trails are dog-friendly and side depends on marginal trails. So I’d love to hear the background. How did you guys start? How’s how has the best, how has your growth been? How has the past year been for [00:01:00] you and your team?
Ron: Yeah, so Alltrails has been around since 2010. And just to be clear, I didn’t start it.
I took over from the original founder in 2015, so he had. You kind of launched it and grown it as a side project for awhile and right around when it started getting traction, this is back in the SEO days. So we built a really impressive SEO engine. And in late 2014, early 2015, he launched the mobile apps.
And right when it started to take off, he got an opportunity to go be an exec at another high flying food delivery company. And he wanted to hand it over. And so I knew him from my days and with Topia, outdoor tech is pretty small. We all kind of. And I was so excited to jump back into something small, but not, not to do it from scratch.
You know, that was one of the things I realized that I’m not a zero to one guy. That’s not my happy place at all. And so the opportunity to come in, something that had a little bit of traction and some clear product channel fit, some inklings of product market fit. I jumped at it and, [00:02:00] uh, you know, we were a six person company, uh, when I took it over super small superscript it was, and it was a cleanup job for sure.
You know, Triage a different area of the funnel. Every quarter, you know, one quarter we are going to tackle signup rates and one quarter we’re going to tackle pro conversion. One, one quarter we’ll tackle churn, but we kind of, we stayed lean, we got it out. And then late 2017, we hit profitability. And that was a big point of pride.
We did it without raising any, any money and we saved. Yeah. Right. It’s such a, it’s an anomaly in our space. Totally. Yeah. And we’ve just been kind of growing it from there. You know, it’s been a ton of fun.
Mada: I think the last year you guys probably saw a lot of growth. I definitely joined and actually like first use it for free.
Then I became a paid subscriber. How have you seen, you know, what, well, how was COVID for you in general? I’m imagining good, but I’d love to hear from you.
Ron: Yeah, it was crazy. I, and I’m sure every single one of your guests, [00:03:00] if asked the same thing as said, as had the same response, it was crazy. We came into 2020 with I think 28 heads.
We’re still small and, you know, really focused on just like steady organic growth. Mid-March the whole kind of machine ground to a halt, right? When the world health organization declared the global pandemic, you know, no one was out hiking and mountain biking and backpacking, right. Everyone was scared.
That your dog could give you COVID right. Or the air could be COVID. Um, I remember, you know, like I’m sure like a lot of people like bringing, you know, a ton of hand sanitizer out there when you’re just opening those trail gates. Cause like, am I going to get COVID from this? It was crazy. And then the lockdowns happened and we kind of placed a bet.
We placed a bet. We said, you know, there’s some short-term headwinds right now. This is not a new normal, I have three kids and a dog T right. So, so my family and I were also thinking like, what is this summer going to be like, we had a cancer. All of our family vacations. We started canceling the summer camp or the summer camps [00:04:00] got canceled on us.
Right. Then we were looking out at the summer. It’s like, there’s going to be nothing to do, but hike this. I’m like, that’s the only way we’re all going to stay sane and not tear each other apart. I have the kids bouncing off the wall. There’s going to be nothing to do. That’s going to be the only like outlet.
And if we’re feeling this way, you know, I’m sure millions, hundreds of millions of people around the globe are feeling the same way. And so we said, you know what? Even if the business has kind of slowed dramatically it’s short-term and we’re gonna, we’re gonna swim through the whitewater here. We’re going to start hiring.
We were able to suddenly in a very short amount of time to get access to talent that I don’t think we would have had ever had access to just a couple months prior. Right? All these a list, tech companies, all around us, we’re shedding folks trying to reduce costs. And we say, you know, we’re going to, we’re going to go get them.
And so we started beefing up the team. We started, uh, increasing the cadence of outbound communications and email frequency. We started ramping up paid [00:05:00] spend. And then right in may, um, when the lockdown started easing up and we kind of resettled on this, like new normal, our business shot out like a cannon.
And, uh, it was, it was triple digit growth. I think it was, you know, again, it was just a ton of people like you who maybe, you know, whether or not you ever spent any time outside as a kid or not. I think a lot of people. We’re recognizing the value that time outside could play during such a stressful, crazy, chaotic time.
Right. And it’s not just like a physical health thing. It was like the, the mental health aspects, the emotional health aspects, just giving people a sense of normalcy or a sense of calm even for a little bit. I think that was a huge driver of it. And, and it’s maintained, you know, like for us, COVID was an acceleration of a trend that we’d been seeing for years, which is this collective reawakened.
So the awesomeness is spending time outside and it’s, again, it’s like this, this global phenomenon that’s happening. And we’re just trying to, we’re just trying to kind of [00:06:00] capture that and say as, as far in front of it, as we possibly can, I love that.
Mada: How do you think about growth today? No, you’re you’re over 1 million subscribers, 25 million registered users.
So surveying impressive numbers. What is growth for you? Is it user acquisition? Is it like engaging and keeping users? How do you think about like the different stages of growth and what do you focus on most
Ron: now, even though I’m currently CEO at all, Charles, I still consider myself a growth guy. Yeah. So that’s, that’s in my, that’s in my blood.
I, I, so I, I think of growth holistically, right? Full funnel. It’s not just top of the funnel, you know, top of the funnel sometimes is outside of your control even. Right. And that’s been, uh, we can talk about that later this year has been crazy as a red hot economy and worlds kind of opening up kind of not, you know, the challenge is to get users attention.
Like that’s a really interesting challenge right now, but you know what we can control. That’s what I like to focus on. Right. So it’s going to be stuff like sign up rates, pro conversion [00:07:00] rates, churn rates, rates of UGC contribution. That’s a big part. We have a flywheel. Business. And so really thinking through what drives a flywheel new user activation, you know, there’s a ton of different ways that we, that we look through this, that we look at our funnel and, and again, like what drives growth.
We’ve been spending a lot of time lately talking about viral loops and how we can better leverage the strength of our community to go out and accelerate our rate of growth. And what’s been really fun for us is, you know, we’re building a global brand and a global platform. What were talking about during COVID and this need to get outside this need for the holistic health benefits of, of time outside.
That’s not just, you know, for north America, we’re seeing the same, same things popping up in the UK and France and Germany and Spain and South Africa and Israel and Latin America. So we’ve been focusing a lot of time and energy internally on scaling up growth. Right. And that’s, that’s been a really interesting thing.
How do you kind [00:08:00] of solve for the cold start problem when you don’t have UGC in certain markets? Right? So, yeah, this is a it’s very much top of mind. We’ve been, uh, you know, like you said, we w we recently crossed 25 million registered users and a million pro subscribers that was back in January. We announced that.
And internally, you know, we, we see a clear line of sight to a hundred million registered users, 10 million pro subscribers. But honestly, we’re talking about. What does this platform look like with a billion people on it? Wow. How can we get there in the next 10 years? And what does that need to look like?
So it’s all driven by growth.
Mada: I love the ambition. It’s, it’s very inspiring. How do you think about, do you have some examples, for example, of the growth loops, for example, that you’re talking about either that you’ve tested and worked well or that you think of testing? Yeah.
Ron: Yeah, we have there’s there’s quite a few.
There’s quite a few. So for us, the heartbeat of all chills is our trail. Right. Everything starts with trail content. We can’t go into a new market if we don’t have some kind of critical, massive of [00:09:00] trail content, trail density there. And it’s an inexact science, it’s hard knowing like what, there’s no preset denominator and say, okay, there are, you know, this many hundred thousand trails in France.
And so we need to cross this threshold together. There’s kind of, you sort of put some rough calculations together based off of like land mass and population. So a lot of, a lot of the loops start with that. We kind of have our own first party data and there’s third-party data and there’s a ton of AI and ML and human ops that we’ve built on top of it.
Again, this is the heartbeat of Alltrails. And then that’s just the starting point though, you know, and, and, and we it’s centralized. It is, you know, we, we have boots on the ground across the world, but for the most part, it’s centralized through our core system. So then, then the question is like, how can we.
Fine, tune it as quickly as possible. What are the different feedback loops that we can create? Whether explicit or implicit? Also there’s both like passive and active feedback loops that we’ve been able to create where our users help curate our content and the [00:10:00] instance where we do get it wrong. You know, maybe we say something as dog friendly, but it’s not dog friendly or, I mean, even at a bigger level trailers.
Trails are fluid. You know, they’re not like roads, right? Like they’re, they’re constantly in flux, whether it’s fires, whether it’s floods, whether it’s maintenance, whether it’s development, it’s never static. Even like year to year, it’s not static. And so really thinking through, again, the different feedback loops that we need in order to get those as accurate as humanly possible.
And then. What we do with that trail content. So again, if it’s like, if we’re a storefront, if we’re a marketplace, that’s kind of like the supply, our trail content is the stuff on the shelf. And then what we do is we try and flood it with UGC. And I think that’s what makes all chills really unique is that combination of curated content coupled with, you know, really relevant recent UGC so that you can get that real time feedback on like, you know, this is flooded out or it’s muddy bugs right now.
And that’s [00:11:00] again, like really built on this continual process of growth and optimization and, and, and feedback roof with our users. How do we extract maximum UGC And how does that differ by country? There’s different motivations in different countries. Whether people want to do a, to help the community, whether people want to do it.
You know what I mean? Like really trying to tap into the motivations kind of at a cultural level as well has been really fascinating. So opening up again. More feedback loops more ways of listening to our users out there and really trying to understand like the nuance and the dynamics of a market, and then how to kind of fine tune strategy based off of that.
I love
Mada: it. How about like engaging and bringing people back into the app? How do you think about that? Is it just, you know, when people are thinking about neutrals or are there any like notifications on things that you’re playing with to remind people to go on hikes, to come back.
Ron: We still tread lightly when it comes to push notifications, we all know that there’s more we can do, but we’d kind of rather err on the side of not being annoying [00:12:00] than overly aggressive, but we are starting to really dive into personalization and curation.
And so we do, for example, now like a curated monthly email of trails, we think that you’ll like, so if we know, for example, Mada loves dog friendly trails that are between three and six miles. We can surface all of the trails near you that you haven’t done or have done, but maybe not for awhile. So we’re trying to, we’re investing a lot of energy on that.
I think that’s super exciting. One, I’d say kind of strategic advantage we have is because we’ve been around so long. Cause we’re old is our legacy SEO strength and we’re able to leverage. SEO as a re-engagement technique, you know? Cause that’s cool. Yeah. Right. So like the app is by far the best form factor for all trails, without a doubt location services and everything else, it’s just it’s the best.
But we all know. I mean, how many apps does anyone really use or keep top of mind at any given time? Like the phone can be kind of a black box sometimes. And so. [00:13:00] We are able to parlay our SEO strength into as, as a re-engagement channel and deep link you back into the app just from, directly from the server or use branch journey is to get people back into the app.
So that’s actually been a really great driver of re-engagement for us. I think sometimes people maybe forget they have the app and we’re able to get them right back in. It’s like, oh, oh yeah. Oh yeah, that’s right. This is pretty cool. Wow.
Mada: And when you think about like the things that are top of mind in terms of metrics and things that like matter a lot to you, what are the top metrics that you look at every day or
Ron: every week?
I’ve definitely come to appreciate. I don’t like looking at daily metrics. They’re too, they’re too noisy and I’m not sure that I have a longer view. So I tend to look at things I there’s a weekly health check, but I like looking at things monthly. We have a very seasonal business in a normal non COVID world.
It looks like a bell curve. What summer, the summer months being peak utilization, we follow the sunlight. It [00:14:00] kind of makes sense. Last year, last year it was basically like, you know, we saw the upslope in April may, and then it kind of like just kept going up into the right. It never came back down. Even through the winter utilization was on par with.
And we’ve seen that trend continue into this year. And so that’s been a little bit strange. So we tend to, because of the seasonality or at least the habits around how we’ve historically looked at this business, we tend to look at things year over year by month. Right. That’s kind of like the core view that we have because even on a weekly basis, there’s noise, there’s micro seasonality, you know, compare a weekends mid week or how, you know, the, the date lined up.
Was it on the weekend last year versus this year? So from a monthly view though, it kind of all washes out and that tends to be sort of the, the best health check for us. Now, the crazy part is when we’re lapping the, you know, the, the craziest comps we’ve ever seen in our company’s history, which is again, the growth rates in 2020, and then how do you sort of normalize [00:15:00] or account for that and, you know, get that sort of like holistic health view beyond just, you know, You ever year by month framework where we’re doing like two year Katter stuff now, which I didn’t go to business school.
So this is all new to me, but you know, it’s just different ways to kind of like, just, is it working? Are we moving in the right direction? And then same with some of the new countries too. It is a different set of metrics then we’ll look at from a mature market framework. So yeah, it’s kind of always kind of changing this up.
You’re getting this out as we, as we go.
Mada: I think that’s, that’s really interesting. And I, it’s just interesting to think of like, you know, the seasonality, but like COVID has changed everything. I’m curious to see if like this year we stay the same. If people will like actually build the habits and now we’ll go on more.
Will they go back to life before? I think it’s, you’ll have such interesting data into human behavior.
Ron: Like last year, for example. So, so pre COVID again, it was like a U curve, right? So over the course of year, it’s a bell curve. If we look at it a weekly basis, it’s a U curve with [00:16:00] Sunday and Saturday being peaks.
Then, then Tuesday, Wednesday, Thursday, attending to be troughs. Once COVID hit and people were trading in their commutes for work from home. The shape of the curve changed completely. It remained flat. People were trading their commutes for hikes, and it was so cool to see. Cause we could also see a time of day and you’d see it during the commute hours.
You’d see it in the morning before work or in the evening before sunset after work right this year, we are starting to see the world come back online. People are starting to, you know, coming back into work. And so we’re seeing that weekly distribution curve shift a little bit overall consumption is actually higher than it was last year, which is great.
And this is what, this is something I’m very, very grateful for it. We don’t need to be a daily app, you know, and I mean, we don’t even need to be a weekly out there. Very few people who are able to actually hike every single week, myself included I’ve three kids and life is getting hectic again. So as the [00:17:00] world opens back up and kind of comes back online from our perspective, it’s all good.
Even as people start traveling again, people shift from, from local exploration to international or, or at least, you know, across the country exploration as people go back to the gym. As people start community again, again, we’re seeing like at a micro level consumption pattern change, but at that monthly view and beyond all of the core metrics we look at conversion rate is higher than it’s ever been.
Churn rate is lower than this. You know, like these are all still moving in the right direction. I think. People are able to integrate this reconnection with nature and that their daily habits, you know, again, it doesn’t need to be daily. It doesn’t even have to be weekly, but when you do go on that trip to Hawaii, maybe instead of kicking it at the beach every single day, you’ll try and get a hike or two.
And with your family, you know, there’s these little subtle shifts that, that are starting to take root. And I think that once you’re kind of awakened to them, once it’s kind of like become part of your life and you realize I feel better when I spend time [00:18:00] outside, you just figure out how to layered in it.
Right. And so, yeah, it’s been, um, it’s been really cool to see. It’s been really cool.
Mada: I love it. One question that I always ask is, you know, tell me about some of your favorite campaigns and then maybe some things that you tried that really failed. Sure. The stories are usually people can learn a lot from stories from other pupils.
Maybe a story of success and one of fender.
Ron: Sure. I like the stuff that doesn’t scale. I think that’s always fun. So, you know, we were talking, you have a dog, you, you appreciate that. We have dog friendly tags on all of our trails. It’s
Mada: so hard that Google is wrong. A lot. You guys are not, it’s really good.
Ron: This data set didn’t exist until we, we did it. And so I think it was either 2016 or 2017. We decided, you know, it would be really cool. If we could get every trail in north America to start to have a tag, whether [00:19:00] it’s dog friendly and even differentiate whether dog on leash, your dog off leash or, or no dogs allowed.
And so I did this, I want, we have one of our, I think, seven employees at the time. Her name is Christina. I was like, Christina. Do you got anyone who can help me with this? And she’s like, yeah. My senior prom date is working in a bike shop in Montana and he’s got time on his hands. So like, I’ll give him a call.
So me and this guy, Eddie was like, all right, we’re going to divide and conquer export a list of the, I don’t know, 35,000, 40,000 trails we had on the platform at the time. And we went through them one by one, one by one. Oh my God. Yeah. So if it was tied to a park, I try and go to the parks website.
Oftentimes I’d have to call the park cup and be like, Hey, are dogs allowed in your park or not? And it was like the most, it was insane. It was the craziest thing, you know, and it took us a couple months and I, you know, I’m doing this on top of like every other, you know, day to day tasks that I had at the company.
[00:20:00] But we made it work. We made it work. And, um, you know, and then by the end of it, we had this really, really cool datasets that are, you know, we didn’t, we didn’t get a hundred percent of it right, right out of the gate. But again, those feedback links that we built up, our users got on board. They were really excited about it.
They were helping us out. We have ways that they can contribute content too. And so they were jumping. It was great. It was really cool. That was one of my favorite things that we’ve done. Just standing up a completely new proprietary data set in the back.
Mada: I will tell you that that’s the thing that got me on old trails.
I think I was looking at like things on Google. I started realized they were wrong and that I think I remembered and what friends, just Alltrails. And I realized that they had the dog tag and I was like, now I’m solid. Like, that’s the only thing I use. So I’m sure it does other people like me, but it’s so cool to hear the story of that, how that came to be.
Ron: This is why I love working here because I love spending time outside and I have a dog and I know how hard it is, where to go. And I know what a bummer it is when you drive to a trail head and then [00:21:00] you see the devil dog sign. Oh my God. It’ll ruin your day. Especially if you drive far. Right. And so it was one of those things, like as a user, I just wanted for myself.
And I figured, you know, if I want it, I’m sure other people probably find this thing pretty cool too. And that’s, that’s been one of the most fun parts of working here too. It’s just, you know, going out with your friends. Or hearing hearing from random people, like there is no shortage of unsolicited feedback that people will find me on LinkedIn, just to tell me product ideas or whatever.
And it’s great though. It’s fun. Cause it’s not, it’s not rocket science, what we’re doing, you know, we’re just trying to help people spend more time outside. That’s it, there’s a lot of different ways to do that in a lot of different use cases out there.
Mada: How about the failed campaign
Ron: there? Yeah, there’s been a ton.
There’s been a ton, you know, one of my,
like the running jokes with in growth, you know, How frequently we can get our hypothesis. Like we’ll always place bets on which variant we think will win. And like, somehow we’re wrong, like 80% of the time. Right? Like we never get it. Right. [00:22:00] And that’s why you test and that’s, what’s great about testing, but it’s always shocking to see how wrong our hypothesis.
At least my CS tend to be. So we’ve had a ton of failures there, you know, I don’t know, back in like 2017 or 2018, I thought it be Really a great driver pro conversion. If we did a 30 day money back guarantee and was like, boom, big badge, it didn’t do anything. And actually like pulled down conversion rate.
Why? I don’t know why. I don’t know why, but it was not. Did not drive conversion rate. There’s been no shortage of things like that. Cool.
Mada: How about mobile? You talked a lot about like how important the app is, but you guys get a lot of like traffic from SEO. And how do you think about like converting people to the app and getting them to download the app?
Since it’s pretty enhanced?
Ron: Yeah. Yeah. So, like I said earlier, the native apps are by far the best form factor for AllTrails And that, that is where we see the strongest mid to low funnel engagement and conversion. And [00:23:00] so we know that we need to drive as many people into the apps as possible. So in like 2017 2018 our product channel fit has historically been SEO.
That’s what got us like when I stepped in the door, that’s what got me there We have this amazing SEO engine. And, and, and we knew that we, I didn’t want to build a platform on something we can’t control. There’s always that fear there. Right. And you see all the companies, I tried building businesses on like the Facebook newsfeed and then Facebook changes their algorithm.
It’s like, okay, now we’re out of business. So there’s always been a double-edged sword component with SEO. And so we’re trying to. You know, we want to own the touch points as much as we can. And so doing stuff like taking our SEO expertise and really diving, you know, applying that into ASL, that’s been an ongoing focus, like very excited about some of the gains that we’ve had there and expanding that globally.
So turning ASO into a global growth strategy, you know, and, and paid acquisition is [00:24:00] another one it’s still. Less than 10% of our overall growth, but it’s just a way we can kind of diversify and move the needle a little bit. So, you know, getting that a little bit more fine, tune PR and word of mouth has also been great.
You know, we want, we want to build a brand. We want to be associated. When you think about going outside, we want that association to be AllTrails And so from like a brand competition perspective, it’s not necessarily. You know, some of the other competitors in our category, in the app store, I don’t really spend any time kind of thinking through that.
It’s more, you know, I tend to focus inward, but it is, you know, I want us to, I would prefer, you know, people think about AllTrails When you think about going outside, you think about AllTrails or not REI or the north face, that’s the level of competition you want, but you know, we’re still fortunate in that we do.
A tremendous amount of traffic. I mean, a hundred million people came to our website in the last 12 months.
Mada: You guys use our banners right. To convert some of those users into the app. Is that, that does that work well? How do you think about that?
[00:25:00] Ron: Absolutely. No. And so that’s the thing, like how do you know, I think that’s a strategic advantage of ours and that we’re able to parlay that SEO strength, even the direct traffic too.
So it’s not just SEO, but people coming to the website and then, you know, using branch journeys, You know, the, the little, the installed banners, whatever to, to bridge the gap and get folks directly into the app. And then also with our onboarding campaigns, you know, throwing a, a branch link on every CTA so we can detect your device.
And if you’re opening, if you’re opening the email on your iPhone, we’re going to get you into the app store. If you’re opening it on your Android phone, we’re going to get you in a Google play. It’s a core, core part and B because of this SEO strength and then the ability to bridge. From web into the app stores, we’re able to generate millions and millions and millions of incremental app installed.
So we don’t have to pay for, which is a huge strategic advantage, which then feeds into the ASL algorithms. Right. And so that helps us get, you know, we we’ve hit number one in health and fitness, multiple times in multiple countries. [00:26:00] And so much of that is driven by this kind of web web strength, web dominance.
Again, none of it would really happen without those bridges from web into the app. Cool.
Mada: Awesome. That makes me very happy. I bet. Yeah.
Ron: See you guys high five.
Mada: So you’ve seen a lot of growth and it’s very interesting. I was. I’m curious, how do you think about the growth of your company and culture? I think my, I lead marketing branch, but I’m also very involved in like scaling our culture.
And I think I found this very challenging, especially when you grow really fast. Uh, and we’ve gone through periods where we’re like, you know, double in a year, it’s been really challenging to grow culture. How have you thought about that?
Ron: This is my favorite topic. I am so glad I love it, but we can just nerd out for the rest of the time on this stuff.
I think this is great. I think that the two most important things for any, any startup, any company is momentum and culture And if you lose either of them, they are [00:27:00] impossible to rebuild. Right? So momentum begets momentum like everyone in AllTrails hears me say this all the time. We need a manufacturer of momentum.
We need to fuel it. We need to fan it and we need to keep doing more faster. Right. That’s how we win. Same on the cultural side though. Like I made a mistake in, you know, in, in the past where I’ve lost sight. of it I’ve led it. I took my eye off the ball and you make a bad hire, And you know, that whole chain under that hire that isn’t tainted.
And then that feeds into this downward spiral. Right. And so after making that mistake, once it was kinda like, I will never do this again. I will never let this happened again,
Mada: but it’s really hard hiring is I like you can. It’s not like a perfect science. It’s not.
Ron: So, you know, it’s like hire fast and fire fast.
That’s I think that’s one of the single most important things as leaders we can do is recognize. If someone is not additive to the overall cultural experience or is in that negative or whatever, like we need to figure out one can we course correct? That’s always the best case scenario. Can we fix it?
Can we have [00:28:00] an intervention? Can we kind of get them aligned on our core values or not? And if it’s clear or not, and this is what’s been crazy and this is the stuff that keeps me up at night because we are growing fast. Right? Like I said earlier, we, we went into 2020 with 28 people. We doubled the company by the end of 2020, we had 56.
people We came in at 2021 with 56 people and now we are at like a hundred. So we’re doubling again. And as we look at 2022 yeah, that’s intense. It’s intense. Right. And I still do almost all of the hiring. I want to still be. I think that’s one of the single best uses of my time is again, be that culture Vanguard and train the rest of our leadership across the org, whether they are truly in a position of leadership or sort of like a culture carrier To kind of embody that as well. And really, and it’s tough cause there’s, there’s pressure, you know, it’s
Mada: like not scalable at a hundred people.
Ron: I know, but you know, I’m going to keep doing it for as long as I can at least like for the higher level ones, anyone that’s going to be a manager. Right. And [00:29:00] so good talent.
It with bad culture is a bad hire. And as we are trying, you know, competing for engineering talent is obviously incredibly competitive, incredibly hard. And the number of like super. Talented engineers that we’ve had to turn away. It’s so tough. You feel this pressure, like maybe I should just compromise.
Maybe I should just, just this one’s just, but you realize you can’t do that. That’s how culture erodes, underfoot. And so really holding a, a firm line on that. The good news is the good news is, you know, we are a mission-driven company. And so we’re able to really play that, you know, to our advantage. I think, I think.
Yeah, everyone who works here is motivated by this charge of getting people outside. You know, this notion like people in communities are happier and healthier when they spend more time outside, it’s like really simple. And everyone kind of has that personal connection and that personal epiphany realization.
And so we’re able to kind of use that as an early screening [00:30:00] part to recognize that, you know, the people that want to be here for the mission versus the kind of, this might sound a little bit harsh, but kind of the mercenaries that are looking for a paycheck, you know, they’re looking for a payday, right.
And they can be, again, some of the most talented people in Silicon valley, but if you’re just coming to Altos for a paycheck, Why aren’t you here? You’re not here for the right reason. And because we’re so rigorous and we over index on the hiring process, it’s a grind getting through it. There’s a lot there’s homework where know you’re meeting with many, many, many, many people cross-functionally across the whole company, but if you get through it, what’s great is people don’t leave.
And that’s one of the things that. Proud of is that connective tissue. And that becomes a strength, right? Like that kind of peripheral. Like it’s like when you play a sport with the same group of people for an extended period of time, you kind of know where they’re going to go. You know, like you start picking up on each other’s tendencies and it’s the same thing in an office environment, a little more dorky than that, but, you know, you tend to like, you know, how to play [00:31:00] like as a team.
Right. And I think that that continuity is super important to that. So we’d rather take it slow. On the hiring process and really kind of grind it out, but then have everyone stick around for the long
Mada: haul. I, I think that’s really cool or really interesting. It’s hard, but I think you’re right. It is one of the most important things you can do.
How did you like tell us a bit about your career growth? How did you get to where you are today? You know, you, you paint this decision to become CEO of a company that was six people at a time. Now it’s a hundred. But how did you even get there? Like what’s your career path and seeing made you made that decision six
Ron: years ago.
I, okay. We’ll go back. We’ll
Mada: go back. Okay. Let’s go back. Let’s go back.
Ron: Yeah. So I went to UCLA in the late nineties and I was watching web one dot O from afar. And I was like, I cannot wait to get out there. Like. My buddies, older brothers and sisters went there like we’re in shorts to work and [00:32:00] they’re all sleeping on couches, eating pizza.
And it doesn’t matter how old you are. Like everyone had a voice. I was like, I love this. I love this. And then I graduated and I missed it. Cause like why one auto had just imploded and was like, oh man, I got to go get a regular job. So I did what, you know, anyone who’s lost does I went into consulting. I went to
Mada: Accenture.
I also, that was my first job too. So I understand.
Ron: I know. I know. And so, you know, you get sold on how glamorous is going to be. You’re going to fly around the country. You’re going to meet with all of these exact, it was, it was such a grind. And by the end of it, I made a promise to myself that I would never.
Ever take a job for money. Again, that just life is too short. Like you can’t take any of it for granted. I was miserable. I was, I was a shell of myself, you know, like the lights were dimming kind of stuff. I’d look around at people above me. I was like, I don’t. And not no offense if any, over listening, no offense, but I didn’t.
see A model that [00:33:00] I really wanted to pursue. There is no kind of mentors. There’s no, there’s no one that I was like, I want that. So I didn’t have a path in front of me. So I said, I gotta redo this. And I’m thankfully this happened early in my career. I know plenty of people that are doing this much later in their career.
So I was able to parlay that into a job at Hotwire, an old travel tech company based in San Francisco. I wanted to move back home to San Francisco. And that was great. That really opened my eyes. Like it wasn’t a startup, it was like 160 people. And it had been bought by Expedia at that point, but it still had that kind of tech vibe to it.
And I loved it. And then I was very siloed and I was just like, I want to do more. I need to do more, but I had no business doing more because I didn’t know anything. So I thought I would go to business school. That was my big idea. I’m going to go to business school. And so I took the GMs. And I was like, all right.
Okay. You know, like wasn’t like blowing open doors, but it wasn’t shutting doors. Like, okay. I [00:34:00] think I got a chance to do something cool here. And I started looking at the essays and then I was like, every single school had multiple essays and they were all different and it was just like, oh man, I went to UCLA, I’m a kid of the UC system.
If you grew up in California and it’s like, You check boxes and you write one essay and that’s it like, could not have been easier. And so that was kind of, my expectation would be school, which was not at all. So I started procrastinating immediately and the procrastination actually led to Liftopia and I felt like, all right, you know, if nothing else I’ll have a cool, a cool experience to write about my B-School essay next year.
And then that became the year after and the year after the next, you know, like nine years later. But the big driver behind that was, I wanted to go to business school to learn more stuff, to get out of my silo and really get like big picture. I think I really, I wanted to see that the table, I wanted to see that the table, I didn’t really know how to get it, but you know, what’s better than going to business school to figure it out.
It’s just going out on your own and starting your own thing. Cause like there’s no one else at your table anyways. And if you don’t [00:35:00] figure out how to do it, Lifecycle marketing or paid acquisition or accounting or no, one’s going to do it. And so you just dive in head first and you figure all this shit out at the same time.
And that was like, okay, all right. You know, like that, that was really the step function for me. And I, you know, this was in 2005 when, when I started, you know, different time, it was pre pre web two Datto and, you know, whatever, but I always felt like. If, if this crashes and burns, I can always go back to Hotwire.
Maybe get a better job there because I got a little bit more experienced or better story to tell I can go to B-School. I can find there was always that kind of like, I felt like I had this internal safety net. And so that’s what really opened my eyes. Like, you know what, like, this is what’s for me, this is what’s for me.
And then after Liftopia ran its course, you know, it took six months off, a very intentional six months off to figure out, am I a serial entrepreneur or not? And it couldn’t tell if it was like an internal pressure or an external pressure. And I went and I kicked the tires on a bunch of, in hindsight, really [00:36:00] bad ideas.
And it was the question like, am I willing to put my family through this again? Cause that’s the thing with starting a company, you know this, like, it’s not just about you. It’s a lot, you never turn off. You never turn off. You’re never fully present. You know, I, it would be like Friday night or Sunday morning, I’m hanging out with my family and half of me is gone.
Right. And it was just very real, like, do I want to do that again? Do I want to put them through that? And I said, no. And I wanted, so what ended up happening was he yelling? Was the rebound playing Yelp was like the, the Creek eco-friendly too, after a bad divorce or something. I don’t know. But it’s like, this is the polar opposite.
You don’t need to worry about. I don’t need to worry about, uh, payroll. I don’t need to have like the weight of the world on my shoulders for awhile. And it was cool. It was great. Learned a lot. And I, I love y’all, you know, big supporter of them, but after six, eight months there. It was so there’s just a lot of bureaucracy it’s slow.
I like moving fast. And so [00:37:00] that was what kind of, I was like, all right, I’m ready for something new. And the opportunity for all trials presented itself, I jumped at it. You took
Mada: it. It was a risk at the time and it really, you really made it happen. I think it’s quite impressive.
Ron: Thanks. I saw, you know, we, we went quick.
So we went to, we went to Tahoe that weekend. I was like mulling over the job. And, uh, we’re in, we’re in Truckee and we had at the time two kids, two little kids. Now we have three and we’re, I was trying to use the app to find like some cool family, you know, kid friendly, hikes. And there was like one trail where the trail napkin was in the middle of Donner lake.
And there was another trail where the trail map pin was at the top of mountain rose. And it was just like, oh, no, like what, what is happening? This, this thing is terrible. I’m going to make a huge mistake. And then I was like furiously Googling, trying to find kid-friendly trails. And I just, I couldn’t find it.
I couldn’t find it anywhere. And it was kind of like this [00:38:00] frustration and this, like, it just turned to like, okay, if I can turn this around, if we can make this be the thing where anyone can pick it up and find whatever type of trail you need, that would be bad-ass. That would be really, really cool
Mada: opportunity.
That’s cool.
Ron: Yeah. So that’s what got me here. Okay.
Mada: So before we go into like the fun questions at the end, I have one question. You’ve made some really good decisions. And also you made them hop it, right? It’s not like you joined ultra Islam and there was success, but you saw the opportunity and then you work hard to make it happen.
When you think about, you know, people at their end, their careers, I think this is definitely the time when other people feel, you know, people call this time the great migration or something. I think a lot of people, I think a lot about like, is this the time to make a change? How should they think about their career?
What advice do you have for others who are looking to grow and maybe get to where you are today? One day?
Ron: Yeah. That’s a big [00:39:00] deal. It is.
Mada: It is advice. Would you give to a younger version of yourself? Maybe
Ron: that’s a better way. I think really being honest with yourself, I don’t know. This is probably going to sound.
Pretty basic, but I always, you know, I was projected out like when I’m an old man, when I’m retired and looking back, like, am I going to be proud of my career? Am I going to be, did I proactively make decisions or do they kind of reactively happen to me? Right. And it’s like, how much agency do I actually have over?
This trajectory here. And I always wanted to be in control of it. And, you know, like, even if I make mistakes, even if I get punched in the nose along the way, like it was a choice, it was due to choices I made as opposed to kind of the way world happening to me. And that was, that’s always been a big driver.
That’s always been a big driver is, uh, we’re here for such a short amount of time. The fact that we’re even here so random, we’re here for such a short amount of time. How do I feel like I’m making the most of it and what’s important. And so [00:40:00] kind of having these almost like personal core values, you know, and then really holding up opportunities, present themselves all the time.
Right. And it’s like, you have to be prepared to recognize when they, when they do present themselves and having that framework of like personal core values has really been. Indispensable for me and is what’s gotten me here. And so even when you know, something like all trails, which like, just to be honest, was like, it was a mess in 2015, like this thing was a mess and I knew it was a grind, but I also knew how much joy and happiness and fulfillment it could get, even in failure.
The fact. Trying to tackle that problem. And again, like the, cause the mission behind it is so pure. It’s so clean. I think you’re right. I mean, we’ve seen it with hiring we’ve we’ve straight up, had, you know, applicants from you name the tech company. And they’re just like, I don’t want to use my powers for evil.
I don’t want to use my powers on something. I don’t want my kids to use anymore. You know? And I think that there’s a very real recognition [00:41:00] going on across tech right now, which is like, am I helping, am I pushing the world forward? Or. Am I, you know, or, or are we going kind of sideways here? And I think a lot of people are starting to opt out from some of the big tech companies and looking for things that are more aligned with their personal values and missions and goals.
And I think that that’s great because now, especially with remote work, like it’s easier than ever to kind of break free and it, you know, sometimes you it’s a leap of faith sometimes. Um, and that can be a scary thing, right. This is kind of like the golden era of being able to go and kind of like find yourself and apply yourself.
Yeah, you use your powers for something that you feel is for the greater good. Cool,
Mada: awesome. Well, it’s great to like to hear that. And we usually end the episode with three fun questions and get the audience to know you better. First question is we had to delete all the apps and you could only keep one on your phone.
Why would you keep Spotify?
Ron: Okay, cool. Why music house? We don’t watch a [00:42:00] lot of the, yeah, we always have tunes on though. Yeah.
Mada: Well, this podcast will also be on Spotify.
Ron: My kids listen to it.
Mada: Okay. If you could build an app to talk to an animal, what would it
Ron: be? My dog. Cause she’s so weird. We have the weirdest dog, so I don’t get her.
I really don’t get her. She’s a mini golden doodle, this beautiful dog, you know, half she’s like 30 pounds. Like really nice, but she’s just so. Weird. And I think it’s the poodle side of her. So none of us are, we don’t get her. So I think it would be that I just need it. Like, what’s going through your brain.
Why don’t you do this stuff that you do, Sally, that kind of stuff. So
Mada: now I’m really curious, the quiet,
Ron: I don’t know. She’s like, there are times of day preset times a day in which you’ll spend time with like different people in the family. And outside of that, like she will not break her habits. So like right now she’s in the office with my wife.
She sits like at. The foot of her desk, not like near her, [00:43:00] she’s not getting pet, but she sits at the foot of her desk. All during the Workday. And then at night she will only sit on me on the couch. Like if we’re watching something, like she will not see it with my wife. She won’t even let her and all this weird stuff.
Right. My kids are like, I don’t get it. Why doesn’t she play with us?
Mada: Yeah. She sat in her, happens all. It’s
Ron: very sad, but she’s only like six. She’s not even like an old lady. So anyways, my dog. Yeah. I’d love to better understand what’s going through her head.
Mada: What’s one. Unlike the app with find on your phone.
Ron: Honestly, I don’t have that many apps. You don’t, I don’t know. It’s not that unlikely run it. We have three kids running a house. My wife works full time. Like it’s hard. So there’s any list. Is this app that’s like kind of been indispensable in my office, you know, the, the bottom four apps they have, she actually keeps this like list keeping app and like her bottom floor.
I know. So that’s like, it’s an, a, uh, a place of prominence on my phone too. And again, like no one who knows me thinks I’m that organized. [00:44:00] There we are.
Mada: Cool. Well, this was awesome. I feel, I learned a lot, both about you about all trails, your growth. Thank you for sharing so much with us. And it’s been really cool having you with us today.
Ron: And thanks for having me. It was a lot of fun.