This podcast dives deep into the tactical moves that drive business success, as well as the mental and physical resilience required to sustain it.
Hosted by Adam Callinan, a seasoned entrepreneur with multiple exits, an avid outdoorsman, and an family man with crystal-clear priorities, each episode unpacks real-world challenges, actionable insights, and the mental and physical disciplines that fuel long-term personal and professional growth.
Whether you’re scaling a startup or refining your mindset, disrupting your default is how business and life strike a balance.
Adam Callinan (00:25)
Our conversation today is about what happens when you finally achieve one of the biggest goals in your career. You win app of the year, you build a category defining company, and you realize that you're no longer fulfilled by that role.
We talk about the courage it takes to leave the company you love, why founders need periods of stillness and reflection, how entrepreneurship is less about reaching the destination and much more about learning how to stay in the arena. We also get into product channel fit, community as a moat, the risks of platform dependency, and why some of the most important decisions in business happen when you slow down for long enough to hear yourself think. Our guest is Ron Schneiderman from All Trails and Ace Lee. I'm Adam Callinan.
This is growth mavericks.
Adam Callinan (01:09)
How did you end up at what point did you end up at all trails and how did you get there?
Ron Schneidermann (01:15)
⁓ I let me I I gotta go back. ⁓ so pre-Alltrails, ⁓ I had a startup in the ski space called Lyptopia, and I did that for about nine years. And outdoor tech is really small. We all know each other. And after Lyptopia, I took some time off, I took six months off, did a little sabbatical, which was wonderful. ⁓ can't recommend that enough. And then I did a
a rebound fling at Yelp. I was just like, I want to not have the weight of payroll on my shoulders for a little bit. And so punch the clock there, running growth for about a year, which was great. And when I was there though, the founder of All Trails hit me up. And his buddy started one of the big food delivery companies. So he wanted to go do that for a bit and hand me hand someone the keys. I couldn't say no. And so it was a six person company doing half a mil in ARR at the time.
Adam Callinan (01:50)
Yeah.
Ron Schneidermann (02:12)
Like by no means like the ultros of today, like our success was not a foregone conclusion, but I love the space, I love the mission, I saw the opportunity and I just leapt at it.
Adam Callinan (02:24)
Half a million in AR so what year would this have been, roughly? Twenty fifteen.
Ron Schneidermann (02:28)
Twenty fifteen. Twenty fifteen.
Yeah.
Adam Callinan (02:32)
Okay. So you get in there, what's the first thing that you do?
Ron Schneidermann (02:38)
Literally the first thing that I do is do 180 on the brand. And so like a lot of there it was a crowded space back then. There was actually like quite a few people in the space and they were all catering to the core. They're all catering that same like lone wolf archetype, deep in the backcountry, you know, like yard, the depth of our tools. And I found that so uninteresting. Especially after nine years in the ski industry, it was the same kind of thing, right? Like
Kenry and the core has its advantages and you can learn a lot and have really good conversations, but they all have very unique product requirements. And in the outdoor space, the core is also living out of their vans, doing the dirt bag life, and they don't really want to pay you all that much for all this custom development, right? And so it can be tricky, it can be a bit of a trap. And so I said, you know, instead of continuing down this path to try and win this like super niche ⁓ segment, is like, what if we invert it? What if
you know, I I I grew up outside and I can take for granted spending time outside. I I can go out there without hesitation, you know, and I realize like that's a privilege. All right, you know, it's like 'cause I have confidence, I have knowledge and whatever, right? It's like, well, what if we use this technology to give people confidence and to reduce the barriers to entry and see if we can unlock all of the benefits that someone like me and guessing someone like you can can take for granted. ⁓
And give it to the masses, like how much goodness can come from that. And so it was this 180 degree pivot. It's like we're for the everyday person, we're for the the newbie. And you know how that manifests is like imagery, copy, product development. You know, we really had to like simplify it and and make it feel inclusive for everyone, regardless of age or gender, or race, or socioeconomic status, or any of it. So that was the day one. That was day one.
Adam Callinan (04:34)
Did you know that going into it? Do you have a pretty good idea?
Ron Schneidermann (04:38)
I I I had a pretty good idea and I didn't realize until I really got in under the hood and started like really looking deeply into the product and the roadmap and things like that that like we're just not on the right path. You know, that this is gonna be a slog and it's you know gonna be a lot of heavy lifting for not a lot of growth. Whereas like right here is this like un beautiful, like deserving, underserved segment that we can immediately
go pivot into it just like topical cosmetic changes to start again, just like don't use lingo people don't know. You know, change the images so it's not just like the same like twenty year old fit white dude in the backcountry. You know, like it's not a heavy lift to do that kind of stuff. ⁓ and it really started to unlock.
Adam Callinan (05:26)
How long did it take once you you got in there and did that and made the changes? What was the timeline like before you started to see positive response?
Ron Schneidermann (05:37)
There so
It was probably it was it was it was relatively quick, but I I I kinda chunk out that that chapter of of Alter. It was kind of like a two-year window from I I joined in like August sum late summer twenty five. And our the you gotta the the handshake agreement with the founder was to to grow it and sell it. He was that was like, hey, I think this thing's pretty good, like with just a little bit of work, famous last word, just a little bit of work, we can unlock this and sell it.
Adam Callinan (06:08)
Yeah, of course.
Ron Schneidermann (06:10)
And I got in there and you know noticed a a few things again. Like one, there's this huge opportunity in front of us if if we can earn the right to unlock it. Two, the product just isn't good enough. You know, and I'm I'm a big outdoors guy. I love backpacking, mountain biking, day hiking with my kids, all that stuff. It was like product's not good enough. And so being a product guy, ⁓ I really, really wanted to make it better. ⁓ and and then it was like, well, gosh, you know, if we're gonna sell it.
Let's get to profitability also. Like, I don't wanna, you know, easiest time in human history to go raise venture capital. And it's like, yeah, counterproposal, let's do this the hard way. And so it was like this two year slog. It was a slog. And we were tiny. We it was six of us to start. And so, you know, when you only have six people, ⁓ you don't have a lot of like capacity and throughput. And so you really have to just like force stack rank. And so basically, like quarter by quarter, okay, this quarter we're gonna focus on signup rate. We're gonna see if we can increase, increase sign up rate.
Adam Callinan (06:47)
Yeah.
Ron Schneidermann (07:09)
This quarter we're focus on bounce rate because SEO is our biggest product channel fit. Like, let's see if we can get more people to stick around. All right, this quarter we'll focus on conversion rate. And you just try and like, there's a million fires around you. A million. And you gotta get really comfortable in that discomfort, knowing like I have to live with this part of my house on fire for the next 18 months. And so it's like, what am I most comfortable having on fire and what like must get fixed? And it's just like this.
Sequence of triage, of just like hard triage. ⁓ and eventually it starts clicking into place. So by 2017, we hit profitability. And then 2018, everything just took off because all the fundamentals were in place. You know, like we would really like it, it's not like it was the company that it is today by then. ⁓ but again, it's like the fundamentals were in place, and we could really start building that foundation to truly scale it.
Adam Callinan (08:08)
Having the pieces in place to be able to take advantage of that opportunity for inflection is the part that I think a lot of people miss or don't think about.
Ron Schneidermann (08:19)
Totally agree. I totally agree with you. Yeah. I I feel like product market fit is very important, right? Like you gotta have a a market that's willing to pay for what it is that you're you're building. And I think you know, having good product market fit can get you zero to one, you know, ⁓ no problem. But scaling it is a whole different beast. It's a whole different and that's really about product channel fit. And it's like how
Who is going to unlock this for me? How am I going to get this in front of the masses and do it in a way where I can make more money than, you know, what it costs me to do this thing? And and that was really the story of all trails was our product channel fit was so clearly SEO. ⁓ and you know, for all your listeners today, like unfortunately, it's a much different era today. ⁓ that era's gone. That era's gone. And I don't think GEO is replacing it like in the near term. but back then, ⁓
It was so clear that like we had this tremendous opportunity with, you know, there's the head term like trails near me, stuff like that, but just this huge long tail of of queries around trails and parks and things like that, best best dog-friendly trails in San Diego, whatever, right? Like, so we really, really invested in ⁓ programmatic SEO. We spent a lot of time investing in programmatic SEO and just trying to like get more incremental gains from that core channel and then
That was our foundation, right? So that was those those two years was really leaning into that. And additionally, though, like through the brand elevation and the simplification, the reduction of friction in the UI UX, try and unlock things like with the word of mouth coefficient. That does still exist today. And it's a really squishy thing. ⁓ but we knew, like, all right, you know, like so long as our customers are happy and we're we're meeting their need, we're they're gonna talk about us on the trail. They're gonna talk about us. And so it was a bit of a leap of faith too.
And then you start getting into the paid stuff and all that, like just trying to bend the curve a little bit. But for the first few I I didn't spend a dime ⁓ on on paid marketing for my first three years there. There was no point. We weren't ready for it.
Adam Callinan (10:27)
Yeah, and in the first series, that's like two thousand fifteen into eighteen. The paid media models changed dramatically over that course of time. And two thousand fourteen, fifteen was like the heyday of of Facebook, where you almost couldn't spend it fast enough. and obviously that is a well completely different world today. But through twenty eighteen, I mean, you still had opportunity there in the paid media.
Ron Schneidermann (10:47)
Yeah.
I was like when Apple
Search Ads just launched in 2018. So I was like, okay, you know, I'll start with ⁓ I got pissed off seeing competitors bidding on all trails. So it's like, all right, I'll start with doing like a defensive shield. And that was the gateway drug head, just like, well, you know, I can start going into all these different other areas. And I and that one's easy, you know, because you're really just talking about like bid management. Like you don't, you know, something like Meta, there's a lot of breakage points. You have like your your
Adam Callinan (11:09)
Yeah.
Ron Schneidermann (11:24)
count set up and you have your your bid management segmentation, then you have the creative, and then you have the landing page. And there's just like if one piece breaks, the whole thing breaks and it's really hard to figure out like, is it bad channel or just a shitty implementation on my side?
Adam Callinan (11:33)
Well yeah.
And then
and then sometimes an algorithm in the back end just says, You're off. Like just we'll just center it off. You violated a thing. Can't tell you what. Can't tell you how to fix it. You're just violated. I know. It happened to us a number of times. It always seemed to happen right around the holidays, which is like the critical time we had to hit a grand slam right at the holidays. So we'd have to run two separate ad accounts and always have one on standby in case the first one exploded for an unknown, uncontrollable reason.
Ron Schneidermann (11:47)
That happens. And it's so yeah. Hair on fire.
Yeah.
I I talked a lot about that at All Trails. ⁓ and at ACLE, I talked about it now too, which is ⁓ you know, like you gotta lean into your product channel fit and at the same time recognize that like these are big tech platforms that don't care about you and more likely than not are gonna try and come into your space regardless. You can get kneecapped at any point, right? At any point. And so the the the urgency around diversification and like really owning that ⁓ customer touch point.
It's just it's so critical because again, like whether it's you know, building a business on meta, building a business on SEO, on SEM, on TikTok, whatever, like an algorithm change, or they decide like they like your space a little too much, you get cut out like that. And there's no warning, there's no recourse, you know. And so again, just like not getting caught flat footed more. It just happens one time. One time. Okay, cool. Now I know, right? And then you just go and and get that like durability and resilience as quickly as you can.
Adam Callinan (13:03)
It seems like today, you you know, operating in an entirely different world from a from a customer acquisition and paid media standpoint that you almost can't build it in a single channel like you used to be able to. I mean, this is something we got in trouble with at Bottlekeeper because the meta stuff before it was called Meta, Facebook worked so well and we could not spend money fast enough. ⁓ the result of which is we got completely dependent on it until those things started happening and we had to diversify and get into other channels. But
know, that was a reactive response, not a proactive response. Today you can't build a model directly just on paid media anymore. So it's there's almost like an based on the fact that they work less efficiently is a forcing function to have much more diversification early on. Do you agree with that?
Ron Schneidermann (13:48)
I completely agree. I mean, this is like a very personal relevant statement. My my new startup, ACLY, I've been here just about a year. ⁓ and I I took it over last August. and last year, so ACLY was launched in 2024. Last year was 300% you're on your growth. Like it was gangbusters, right? It was all basically built on meta. It was all basically built on meta, and this year.
You know, I s I'm still kind new in the sea, I'm still learning my way around this thing, but it was like very clear that this is not a durable, scalable foundation for us to go become the company that I know we can become. And you know, again, like one meta change, you that that October what Andromeda when you know it's like, hey, just we're gonna black box it, you gotta trust us. Like, cause back in the day you could be a smart marketer and find alpha somewhere.
Adam Callinan (14:38)
Yep. Yeah, yeah.
Ron Schneidermann (14:48)
and and kind of win, like exploit a channel, right? Like you could be more clever. And then at least like the bulk of your competition, you know? Nowadays, like between both Meta and and Google are like they're they black boxed it. And you can't it's very hard. I'm sure there's some listeners out there like, you idiot, I already did you know, like I'm sure. ⁓ but for us
Adam Callinan (15:07)
No, I don't I mean there there
are ways to do it, but which which we can talk about online or offline, but they require access to things that small companies don't have access to.
Ron Schneidermann (15:17)
It's hard. Exactly. And it's really, really hard. So it's like, you know what? I it it's funny. I I'm a growth guy. and I kind of spiked growth this year. It's like, nope, we we we need to rebuild this foundation for something more diversified and again, more durable, more ownable, more scalable. Because if we're just gonna build this off the back of Meta, we're never gonna be we're never gonna be free and we're never gonna become the company that I think we'd be we can be.
And so it's been this like, you know, cool, eyes wide open. Right. And this is, I don't know, tricks of the trade, I guess being like seasoned and having gone through like so many ups and downs. Just like I I I can get comfortable in that discomfort pretty quickly. ⁓ and just like, all right, you know, like six months, we're gonna be heads down. It's it's intentionally not gonna grow. We're we're gonna build and invest in what we need to do, and then we'll go let it rip on the other side. And so I I totally feel that challenge. I'm sure a lot of your your
⁓ your listeners are are going through the same thing.
Adam Callinan (16:16)
Yeah. I mean, our my my now business Pentain, all of our clients are going through that exact same thing. They're all consumer brands, you know, from effectively startup, most of them are doing at least a million in revenue, up to about 20 million in revenue. And it's they get trapped in the meta Google ecosystem. And I mean, we've had to create a whole entire separate product function through partnerships to be able to give them the access to those things that big huge companies have access to so they can diversify off of Meta and Google. Cause it's like this tiny little sandbox. There's a whole world of sandbox.
But you only have access to this tiny little one and you can't get o you know, you can't get over the wall. It's it's
Ron Schneidermann (16:49)
Yeah.
Yeah.
Adam Callinan (16:52)
So if we look back before I I do want to talk ⁓ about ACLE and get into that, but like if we look back at all trails, you get in and in 2015, it's two and a half million in revenue. How did once you you got past the brand rebuild, ⁓ you know, which surely wasn't just like it starts on this day and is done on this day, I bet it just sort of kind of went on for forever. And it's like one of those things that you just tweak and tweak and tweak. How did the how long did it take for the revenue to really respond?
I mean in two thousand it you know, can you give us like a a picture of what the revenue change was over the course of the next five years?
Ron Schneidermann (17:27)
Yeah, I mean
So 2015 we were doing about half a mil in revenue. by 2018 we're at we we were north of 10 mil in ARR. ⁓
You know, it it's the that's the nice thing about a subscription business is ⁓ you know, when you have good ri retention metrics, it just it's like an it just compounds, you know. And like I had never done a subscription business before. I done marketplaces like a sucker. Marketplaces are so much harder. They're so much harder, right? You're constantly the supply side and the demand side, and everything is just like a one-time transaction. And golly, that's a much tougher business. ⁓ a subscription and like a a good consumer subscription business with like
Adam Callinan (17:53)
Yeah, yeah.
Ron Schneidermann (18:14)
strong retention rates is just it changes everything, especially those first few years where again we weren't spending a dime on marketing. It was all a hundred percent organic. ⁓ and so that was really our superpower, you know, and then we had a good moat. We had a very good moat and that was a UGC. And I think about durability a lot. ⁓ I think about like ⁓ you know before I came to ACLE right I wanted to do something AI native was like whoa, okay, well everything's different today.
That's like the biggest truism ever. ⁓ but it's like product isn't the mode anymore because anyone can go vibe code and knockoff of of what you at least the front end, the the UI piece, you know, like pr in a day, right? And so it's like, okay, product isn't the mode anymore. It's like, well, what is it? I think brand equity, I think community, I think, you know, UGC, things like that, like those are those are real. Those are real modes. And so in all trails,
Adam Callinan (18:45)
Totally. Yeah.
Ron Schneidermann (19:13)
We during those, you know, those quarterly spikes, things like that, like we were constantly like, how do we increase the rate of UGC submissions? Cause it just felt like that was going to be this vicious this ⁓ not a ⁓ what's the opposite of a vicious cycle? The good virtuous cycle. That's gonna be a virtuous cycle where the more ratings we have, the more reviews we have, the more photos we have, the more one, the more it helps our SEO, and two, the more it pulls people into our ecosystem, gets them to stick around also.
Adam Callinan (19:27)
Yeah.
Ron Schneidermann (19:42)
So we really invested a lot of time in community engagement so that it was very important. I have this hypothesis. I like you and I we've been around the block for a while. And so we've seen a lot of these different community-enabled platforms come and go, right? Like like Foursquare was such a thing until it just wasn't, you know? And I I I love Yelp, but like Yelp is not the same company it was 10 years ago. And you know, triple.
Adam Callinan (20:02)
Mm-hmm. So it wasn't, yeah.
Ron Schneidermann (20:12)
It was like the rule travel and you know it's noisy. ⁓ so these these community platforms, they come and go. And that was what kept me up at night more than anything at All Trails, which is like, what is it that causes your community to leave? Because once they leave, it's I think it's impossible to get them back. You know, like if you're a community-driven platform, once your community leaves, I don't know how you like plug the leak. And and that would really, it would literally would keep me up at night.
And what I ultimately like kind of settled on is that it's a symbiotic relationship. It's a symbiotic relationship between the company and the community. And the comp the community needs to believe and needs to see that the company is investing in improving the experience as quickly as humanly possible, right? That it's not static, that they're not taking their community members for granted.
That it's just like a one-way take model. Like it's gotta be like we're both investing in this and like, hey, community, I see you, I'm grateful for you. We're gonna build these things. You want dark mode, we're gonna build dark mode for you, right? Like you want this, we we got you, right? And I think through that, like it creates this like very positive, ⁓ I don't know, like it's a it's a partnership. It's a partnership. So so we spent a lot of time on that. And again, I think that's why it led to this like again, like ownable, scalable, defensible mode.
On the UGC side, which is like, man, you know, the bigger we get, the stronger we get, the faster we move, the harder it is for anyone else to kind of come into our space and try and catch up. Because you're always gonna be playing catch up. And so long as we don't lose sight of the community and it's always like the community first, I think that's gonna be like our defensibility. And it it worked. It's a little different today, you know, but for all trails and for that model, and that one.
Adam Callinan (22:04)
When did you leave All Trails?
Ron Schneidermann (22:07)
I left start of 25, January 25. Pretty recently. Yeah, yeah, yeah. And so that was, you know, nine and a half years. ⁓ I feel like I think everything has its course. Everything has its kind of its natural curve to it. And it was funny, man. I I mean just in the spirit of transparency, right? Hopefully.
Adam Callinan (22:09)
Also pretty recently. About a year ago. Okay.
Ron Schneidermann (22:34)
Like this resonates with with your audience and stuff. I'm gonna real talk. ⁓ you know, I star 2024 was a hard year for me. It was a hard year for me. There was just a lot of stuff going on and we won app of the year 2023. That was like this goal I had set for so long. And when Calm won it, ⁓ I was like, I want that. I'm gonna get that, right? And that was a huge fucking deal. Like two million apps in the app store.
You know, ChatGPT, like we beat them, we beat Duolingo, like that was a big fucking deal. And I was like, wow, man, like I did it. We did it. That was awesome. And I go into 2024 and it's like, I don't feel great. Like, what's going on? What's the matter with me? And it was one of those things, like the first half of the year, I was like, I just need to be more grateful. I just need to work harder. I just need to push this down and bottle it up.
You know, I was like, man, there's 10,000 people that would kill for my job. I'm the luckiest guy in the world. I love, I love this company, I love this brand, I love this team, I love this product, I love our mission, I love the space. I use it weekly, you know, like on pa everything, just get all the boxes are checked, but like something was off. Something was off. And I kind of realized, I don't know, I want backpacking over the summer. I do it every year, it helps clear my head. I cannot recommend enough. Hey, audience, like.
Get off of your screens and just go in nature and and unplug for a few days and and slow down to speed up. Like it'll it's amazing what it'll do to give you clarity, especially if you're grappling with with something, ⁓ even subconsciously, right? It was just kind of this nagging in the back of my head. And I came back from backpacking and was like, There's nothing wrong with me. There's nothing wrong with me. Like this is a natural thing and it's okay. And it's okay. And it's like I'll I can love.
This company, I can love this team and I can love this product and this mission and everything. And also recognize, you know, I'm not getting the personal satisfaction from this phase of the company's trajectory that I was a few years ago. And that's, you know, CEO, founder, it's a funny role because the more you grow, kind of the more you have to let go of all the things that you love, you know, all the things that help get you to where you are. And when you get past a certain size.
One, you're just you're alone on an island, which is just hard. ⁓ and two, like, you know, I'm not CEO cat it it it has too big of a shadow to go into the weeds and like brainstorm with your team and you know, push pixels and like push designs and marketing strategies and all that stuff. Like you hire world class amazing people, you gotta get out of the way. Right? Like you can't go in because you cast too big of a shadow. It's too much weight on on the thumb.
of you know of the scales, right? Like when you say something like, well shit, the CEO said that, so now we gotta do it. And I'd be like, no, no, no, no. I'm just one person. Like, but it it doesn't matter how many times you say that. It's just, it's too weighty. And I get it. I get it. and so you kind of end up like, you know, you at least for me, like just working on things that didn't bring me the most joy. And so I it was kind of like, okay, you know, I think company's in a great spot. I have an amazing executive team. I've got a good relationship with my board.
Gonna I'm gonna transition myself out. And it was a weird thing. And I got I got a lot of people like, what the fuck are you doing? You know, but I also after my first startup, I kind of I kind of like I don't give a fuck anymore what anyone thinks about me who's not in my inner circle. You know, like you go up if you're if you're lucky enough to be on like a a startup that's going up and
Adam Callinan (26:02)
Uh-huh.
Ron Schneidermann (26:21)
gets a little bit of gravity around it. Like you get hangar ons, which is cool, you know, like people come into your orbit. Not all of them have great intentions. And it's like, you know, someone who's not gonna be for me on the other side of this, like what the fuck do I care what they have to say about me right now? You know? And so like I think I I'm I'm grateful. Like it was through again like decades of experience at this point, but I was able to kind of like push aside, like, what are you doing, dude? What are you doing? You know, and just like, yeah, I don't care. I don't care. Care about what my wife thinks.
I care about my kids think. I have like this like very small inner circle of people that I seek counsel from. I was like, yep, this is what's best for me right now. And so I'm gonna do it. And it was wonderful because I was able to leave with so much gratitude and appreciation and love in my heart. You know, like sometimes you hang on too long and things get bitter, things get acrimonious. You know, I was like, I don't, I don't want any of that. Like I'm I'm so
Happy and proud of what we're able to do. And I didn't want any negative, like, like ⁓ seeds of negativity like taking root and tainting this beautiful thing that I was fortunate enough to be a part of. You know what I mean? That was like very, very important to me. And so that was what was great. So I was able to kind of transition out in January. I took a sabbatical, it took seven months, which was rad. ⁓ and then kind of come up and be like, well, it gives me joy. What do I want to do?
Adam Callinan (29:08)
man, so much in there. We have we have a lot of similarities. ⁓ I had a very, very similar experience at Bottle Keeper where we had been doing it for eight and a half years, and the things that I was spending most of my time doing, I didn't like doing anymore. It was patent infringement things and legal stuff and not being creative and solving the kind of problems that I didn't like solving. And and that led to our
Ron Schneidermann (29:10)
Yeah.
Adam Callinan (29:36)
being open to acquisition and that that happened. And then I also took a very forced, I wouldn't call it sabbatical, but I took time to do nothing for a while and and let things evolve. Did that seven month sabbatical, was that preordained? Did like sit down and say I'm taking seven months or did it just happen to be seven months until the next thing?
Ron Schneidermann (29:54)
No,
no. I I I broke it up into two chapters. I broke it into two chapters. And the first chapter was like, you know, I wanna do nothing for a little bit. Like I wanna just straight up like do nothing. And I wanna shed this ultra skin and just get back into being Ron Schneider. Not ultrails, Ron, not you know, just like just me. I wanted to break some habits, like I don't know about you dude, but like I I was picking up my phone like every like 45 seconds, like, ⁓ what who you know, slash who's
I was and I was doing it for like the first week after it's like no one's trying to reach me. What am I doing? You know, so I needed to like break up with my phone. I deleted Slack, I hit my inbox, like that was wonderful. And I just wanted to like, I don't know, I had this mentor years, years, years ago. After I left my first startup, he's like, Ron, you're like this air hockey puck. You're like bouncing around the table. You need to come to a stop and then figure out what's next. It's like, damn, that's wise. ⁓
So that that was kind of the goal. And it wasn't like three months. It's just like, I'm just gonna do it till I'm bored. I'm just gonna do nothing until I'm bored. And I got three kids, so it's not like I you know, do you go down to Patagonia and like just lose yourself for like a month? I was like, I I would have loved to, but no, I was driving to lacrosse five days a week, and that was great, you know. I was cooking dinners, I was reading during the day. I day hiked, I I definitely like saw all of the Bay Area greatest hits on all trails that I finally got the chance to experience. That was a ton of fun. ⁓
And it was, I thought it would actually go longer. ⁓ but it was we were on spring break in ⁓ my daughter's gonna be a senior in college or in the high school, well, senior in high school. but we were doing all the college stuff. And so we're we're in New Orleans checking out Tulane and Austin checking out UT. And I kept waking up at like three in the morning. It was like, what's going on? What's going on? I do that, I do that. Like my subconscious is like, hey, wake up. ⁓ and I it hit me, it's like, ⁓
I'm bored, like I'm I'm done. I'm done with this selfish part of my journey. And I miss that part of my brain. And I miss you know, talking to cool people, doing interesting things, you know. It's like, all right. So then I was like, okay, this this chapter is done, and now I need to go forth and figure it out. And the way I kind of thought about it, I think you'll appreciate this actually, Adam. I I was like, I got a compass but no map. You know, like my compass is is my core values.
It's what I know I'm good at again, consumer scaling, not zero to one. It's gotta be mission driven. ⁓ I knew my strengths, I knew my weaknesses. That was like my compass. And then the map was like, I gotta go fill this in. I just need to start talking to people. So I I put this LinkedIn post out there and I was like, hey, anyone wanna talk? You know, like I I had I don't know if you had you dealt with this at your start too. I would get like
20, 30 inbounds a week on LinkedIn when I was CEO of All Trails, being like, hey, I'd love to pick your brain. And I had to say no all the time. And it gave me a lot of heartburn. Like it really like, it messed with me because I was like, my God, like this is such a beautiful thing. People are coming to me for advice and like counsel. And I'm saying no. I I I really struggled it. My my VP of people, Doreen, was like the best ever. Like, she was basically my therapist, but she was like, yeah, no, time preservation, you can't do this.
But here I was flushed with times was like, anyone who wants to talk, let's talk. And I had, no joke, over 200 Zooms like that. Like scal I was doing like 20 to 30 hours a week of Zooms. I'm actually a pretty introverted person, ⁓ but I found it very restorative. Just again, like just I never knew what I was walking to. Sometimes it's like a private equity fund looking for Intel, sometimes a VC, startups trying to recruit me, whatever, or just like a kid.
In college trying to figure out what they want to do, or like a struggling entrepreneur being like, I don't know if I should let go or not. And it was just like, I don't know, man, every day it was just like, wow, like that was a really enriching day. But over the course of that, the map started to kind of fill in and seeds were planted. And I'm a big believer in the universe presenting itself and that's what happened with Ace Lee.
Adam Callinan (34:09)
Yeah, more
incredible parallels in there. Exactly. Like I had a wise sage, I was a performance coach who was a seventy-five-year-old gangster who just said, Look, you have to sit still and do nothing for a while. And it's gonna hurt and you're gonna hate it, but you have to do it. And he like brute forced me to do it. So I got into woodworking, like just doing random stuff and woke up one day five months later and realized that my brain was melting. Like I I went to him, I was like, Dr. Jeff, my I literally, my hardest decision today was what to have for breakfast, and I'm losing my
Ron Schneidermann (34:33)
Yeah.
Adam Callinan (34:38)
He said, Okay, it's time. He called it soft offense, exactly what you did. Just like, just go start push, go and push gently. And I went to companies that we had invested in and just said, Can I look under the hood? Can I help? And they said, Yeah. And that like kicked off this whole next chapter.
Ron Schneidermann (34:40)
Exactly.
Yeah.
It's such a gift. If you, if anyone who's listening, if you ever get the opportunity to take us about like, I feel like the second you get into the worst thing, like we're we get stuck in this current. You can't, if you're lucky enough, you just get like a sequence of like you get recruited in and this opportunity presents, and you just go, go, go, go, go. And the opportunity just get out of the current and just stand on the bank a little bit and just like catch your breath, reconnect with who you are, what gives you joy, what gives you energy.
And then go back in and have like some agency and some control. Like it's a gift. It's a single I've done it twice and it's like two of my favorite things ever in my career, what were both of those opportunities.
Adam Callinan (35:36)
You mentioned in earlier on the value that you have had from getting out into nature, going out on backpacking. Is that a thing, you know, that you mentioned doing it at least once a year, doing like a multi day thing? Do you do that alone or do you do that with a friend, a spouse, a kid?
Ron Schneidermann (35:55)
I've done both. I done so ⁓ I do my my annual backpacking trip is with a couple college buddies and high school friends. We have the same crew, we go every year. That's awesome. We're gonna do the ⁓ Teton Crest Trail this year. Very excited about that. so I do that, but then I love solo camping, solo backpacking. So ⁓ maybe three weeks after I left All Trails, I actually did a ⁓ four-day solo little walkabout in Death Valley by myself. And it was
It was perfect. It was exactly what I needed. My first sabbatical ⁓ after Lyptopia, after my first startup, I went and did the Napoli Coast Trail by myself for a week and I just posted up out there. And again, like, I don't know, man, like you just you put your phone away and you just breathe and just sit and you know think or not think, write. It's it's it's the the time and the slowness is a gift.
And again, it's through the slowness that like then you can go and speed back up. But I think it's really important to like take yourself out every now and then. That's like so I there's this thing. Well Ultrails was kind of known for my one of my favorite things about Ultra's the first Friday of every month, we actually closed the office for trail day. And so we just we shut it down. And it's like, hey, just go hiking or skiing or mountain biking or whatever, go rafting. Just like, but but get away from your computer.
We had a b a big distributed remote team, like meet up with other folks in your area and just just go outside. And then, you know, we had a Slack group when people came back and wanted to share, you know, if they were dog fooding the latest QA build or a competitor's product, or like, my God, you know, be so cool. Some of the best ideas came from it. But the the the the biggest thing about it was just giving people that time to just like step away, think, not think, whatever, and then come back invigorated. And it was like, I think it was like the secret sauce of of
of our culture and ⁓ what drove so much of of the growth and made all trails what it is today.
Adam Callinan (38:00)
That's an amazing forcing function. Maybe there's something, you know, you talk about like taking a sabbatical, which in inherently typically means it's a much longer period of time. So it's hard to do this in the context in which I'm about to explain this. But removing yourself from your environment is a critical piece of that. Now, doing that for four or five months, maybe that's not realistic. I also have young kids, so that's not gonna happen. But but I do a couple of times a year go out and
And disappear into the woods. It's usually hunting related archery or whatever with a buddy on horseback. And we just go out in the middle of, you know, in some cra literally like the crazies is the mountain range. We did this in in this last fall, and just disappear on horseback up into the mountains for five days. And it's the detachment from your space that is one of the things that is really valuable. It's I think it's really hard, even if you try to put your phone in in the drawer to ex to get the value.
From turning it off, you know, if you're in your own space and there's just something crazy weird about nature and the universe and being out in the woods.
Ron Schneidermann (39:08)
And it just makes you feel human. I mean, sitting in front of a screen all day is not what we're wired to do. Like psychologically, we're not built for that. And so just getting back in again, I you know, what you do is not accessible to everyone. Like, that's badass. Super badass. But not accessible to everyone. So it doesn't even have, it doesn't have to be like crazy. It doesn't have to be backpacked. It doesn't have to be any of that. But it's just like, get out, get outside, get into nature, even if it's just like a little.
Adam Callinan (39:23)
Of course. Of course.
Ron Schneidermann (39:36)
Nearby park, like just go for long walks without headphones in. I think I tell that to people all the time, like just slow walk with no headphones in, you know? And just like it's amazing how you're gonna come back. And again, you you it might not feel like you're at it might just feel like white noise or like silence, but you're gonna come back and like things are gonna be unlocked that you've been battling with or stuck on, things like that. And so I'm I'm with you. Like you you have to get away from the computer, you have to get outside.
You gotta get some sunlight on your skin. You gotta see some trees, hear some birds. Just good for the soul. And it's what we're that's how we're wired. Like that's what we're built for.
Adam Callinan (40:13)
Do you a hundred percent agree with that, to be clear? And and I fully deeply appreciate that my access to Montana is not typical and and that whatever that ba and I don't I'm not riding a horse, you know, every day up into the woods. Like that's a couple times a year thing that I am fortunate to be able to do. Just getting away from whatever your baseline is. Just get out, get your blood moving, get into the sun. Do you have a forcing function for that? Like, do you, you know, set an alarm every
Ron Schneidermann (40:16)
Yeah,
Adam Callinan (40:39)
Hour and a half that says go outside or is it is it just a thing that's sort of inherent to you now?
Ron Schneidermann (40:43)
I wish. I got two dogs. That's nice. They, you know, I mean again, it's like a walk in my neighborhood twice a day, you know? But it's it's better than nothing. It's better than nothing. We're all kind of works in progress. You know, there's lots of stuff. Like I should do push ups every day and I don't. I should meditate every day and I don't. I should stretch every day and I don't. I should practice gratitude every day and I don't. You know, like there's all these things like I should be doing and I don't consistently, but I try, you know, I try.
Adam Callinan (40:46)
Okay.
There's an interesting thing in there that I I learned from my experience with Dr. Jeff over the year that he and I were were together. And that is I look at I in the exact same like I should meditate for twenty minutes a day. I should write two pages in a journal every single day. I should dot dot. And I end up getting in this routine where I don't do them because I'm mentally attached to the duration or I'm mentally attached to the amount, which is the wrong framing. Like, isn't two minutes is better than nothing? Like literally anything.
is better than nothing, which has really been helpful for me to to kind of reframe how I look at that activity and those things that can be really helpful, even if they're in tiny little bursts.
Ron Schneidermann (41:52)
I think that's great call out. And you know, I'm gonna take that and I'm gonna connect it to entrepreneurism, which is I think underneath all that is this notion of just like taking it easy on yourself. And I think as entrepreneurs, as founders, as execs, like we're really, really hard on ourselves. Like if you're gonna succeed, it means like you've got an internal motor, right? Like, and chances are, I I mean, just speaking for myself, like I am harder.
On myself than anyone else will ever be ever, right? Like, and I think a lot of us are are wired that way. And I think it's this notion of like, I'm not perfect. And and and you know, I'll chase progress over perfection, I'll chase like little incremental improvements, like it's all good. It's all good. And I think that part of this journey that we're on as entrepreneurs ⁓ is kind of like.
Learning to kind of figure out those little things in order to make this sustainable. Cause otherwise it's just too fucking hard. You know? Like this is a hard, this is a hard arena that we compete in. You know, I I've I I think about it a lot in terms of like, you know, what? Professional sports, probably like Hollywood, politics at like a national level. Like those are, you know, very cutthroat. But entrepreneurism, you're talking about like the smartest people.
on the planet coming and you know trying to like get a startup off the ground. Like the the bar couldn't be higher, the level of competition, intellectual competition couldn't be higher. You got, you know, these kids that are nine, nine, sixing, even though they don't know what the fuck they're doing, but like they're putting in the hours, you know, and so like it's really hard to stay in the arena. And I I try and I I figured this out a while ago is like startups gonna come and go. Some of them you're gonna make money on, some of them you're not gonna at all.
But it's really about this journey. And it is like a through line. It is this continual through line journey about the things that you learn, the people you meet, like, you know, through the mistakes, through the hardships, you know, that makes you like stronger and smarter and more resilient. And that's part of the growth. So like even the bad things are like these amazing like growth opportunities. Like that's all it's the journey. It's the journey. There's no real finish line. When you sell your company or you hit a certain ARR multiple, like that's not a finish line. Like, all right, now the goalposts have just moved, you know? Like,
Adam Callinan (44:10)
Exactly.
Yeah. It's just the end of the chapter. It literally is just the end of the chapter. That's it.
Ron Schneidermann (44:11)
There's no finish.
Yeah.
And then it's on to the next thing. And so I think being able to have that longer view and view it's like this is gonna this is my career. Like again, things are gonna come and go. ⁓ but I wanna stay in the arena and I wanna stay competitive and I wanna be able to compete, which means like I gotta figure out how to pace myself, you know, and that's hard, and it's these little things like, yeah, I'm not perfect and I'm not gonna beat myself over mistakes, I'm not gonna worry about 20 minutes of meditation, but you know.
Two minutes is better than the zero minutes that I did yesterday. So like, all right, right. And I think it's just like these little tricks that you figure out how to be a little easier on yourself. Because again, if you can't be easy on like no one else is, right? And so it's gotta start with yourself.
Adam Callinan (45:02)
you looked at a I'm gonna do a really awkward transition here because I do want to talk about ACLE. When you I mean honestly Ron, like I could spend 10 more podcasts talking about nothing other than the last 20 minutes of what we just talked about because it is such a hugely critical, profound part of my life and the journey that I have gone through as an entrepreneur and having had, you know, I'm using air quotes for those of you not on video, like success and been miserable.
Ron Schneidermann (45:17)
that's yeah.
Adam Callinan (45:31)
And had to learn through that and change and and I'm a dramatically better human and dad and husband and operator as a result of those changes. So I think they're important to talk about and share. but I do want to talk. So maybe yeah, maybe we need to have like a part two that's that's nothing but like talking about the tactical realities of entrepreneurship. But I do want to get into Daisy because I do think
Ron Schneidermann (45:44)
Okay.
Adam Callinan (45:53)
I do think it is an a really interesting concept. And I'm I'm particularly interested in your position on the state and how ACLE looks at preparing people for higher education in this I feel like we're kind of in this odd, interesting transitionary period in and around the validity of higher education. And and I yeah, kinda interested in take on that. So why don't we start by just explaining what what ACLY does and we can go from there.
Ron Schneidermann (46:11)
Yeah.
Yeah, yeah, yeah. So Ace Leap Today is ⁓ AI-enabled test prep for the SCT and ACT. Right? And so it's like it's it's pretty straightforward. ⁓ it's it's like creating the like personalized and adaptive plans, kind of like at a fraction of the cost of a tutor. And and so this is a world that I'm living through right now. You know, I got three kids, my oldest is about to turn 17, she's gonna be a senior next year. And
This was one of those things where ⁓ we started kind of test prep for sophomore year. And it was the same books that you and I had when we were kids, you know, like just gathering dust in the corner of a room and these she's such a smart kid, but it's like, what do I care about this test? You know, it's like, no, dude, you don't get it, like this matters. And then we got a tutor and group tutoring, she hated it. We got a private tutor, she hated it. I was like, at my wit's end, like I don't know what to do. ⁓
Because if you don't take this as seriously, like doesn't matter how smart you are, like you're not gonna get in the schools that you want to go to. And so I was advising an ed tech company in the UK at the time. They're like, dude, you should check out this startup by called Ace Lee. It's 20 minutes a day. and so I was like, I got nothing else to lose. Showed my wife, she's like, We got nothing else to lose. And it raised her score 160 points. 160 points, man. It went from a 1390 to a 1550. And it was just like, this was before I started working.
Right. And so this was like I said earlier, like, I believe in the universe, like presenting opportunity. You just gotta see it. When I was out planting seeds, I talked to a little in this one VC, I love four-runner ventures. I think they're one of best venture venture capital shops in the business. And I was talking to the managing director there, telling her, like, I want consumer and AI native and ⁓ mission-driven. She's like, one, good luck with that. And two, like, you know, we'll see. ⁓ and then a few weeks later, she's like, You're not gonna believe this, but I actually think I have.
The thing for It's like, what you got? She's like, well, it's an ed tech. I like, ⁓ I don't know shit about ed tech, but okay. And then she started explaining, yeah, it's this AI test prep for SCT and ACT called AC. It's like, stop, stop right there. You're not gonna believe this. We we love this, we've been using it, you know, and it's just like, all right, universe, I see what you're doing. I got you. And so I think about it a lot. The you know, like, you're right, the the state of higher education is changing, and it's gonna be fascinating to see.
I think the contraction of it, because I think not everyone needs to go, and especially, you know, whatever. Yeah, I can't pretend I have a crystal ball, but I do think that like there is a rise and then a need for blue-collar jobs and apprenticeships and things, and it's great that they're being destigmatized, right? Like it's a wonderful thing. So more and more people should just go and explore that. That's great. Not everyone needs like a four-year liberal arts education. Not everyone does. ⁓
But there's always gonna be a need, and I think it's one of the best things that our country does is our higher education system. And so, you know, it's really fascinating, right? Considering twenty twenty, a lot of these schools were like just threw up there and it's like, we can't, you know, just stop with it. Don't worry about the test. Like, we'll figure it out, we'll get you in. And within a couple of years, it's like, nope, we're we've made a terrible mistake. We have no calibration, right? There's this whole thing from the UCs that just came out a couple of weeks ago, like, you know, kids are in calculus and they need to do remedial math, and like we are
Setting these kids up to fail, and it's actually like incredibly inequitable. And I do believe that. I don't think there's anything inequitable about the tests themselves, but I think there is inequitable access to test prep. And it's because again, tutors have historically been out of reach. And so what I what struck me when I was sitting in some of these tutor sessions, like, you know, AI can realistically do like 80% of this. And again, like at a fraction of the cost, which means like we can you can make it just more accessible to the masses and like all trails, like
Everyone deserves a right to the holistic health benefits that come from time outside. It's like tear down the barriers. Same here, like any kid who wants to put in the time and like get mastery of the test and like unlock the opportunities of higher education through that, like give them the chance. Give them the chance, right? So the the mission piece was like it deeply resonated with me. And again, like being able to like really bring it out to the masses. So it was one of those things, man, like we were talking about earlier about like the parts that give you joy, right? Like when you look over the life cycle of your business.
It w when I was kind of thinking about what what's next, I was like, I love it when it's small. I love like I love it when you're just in a room with your people and you're just all whiteboarding and like no one gives a fuck about titles. It's just like, it's just like smart people like aligned and passionate and curious and like that to me is as good as it gets. Like being in a room with your people whiteboarding is as good as it gets, you know? And I was like, that's all I wanna do. I wanna feel that energy. I wanna feel that like, yeah, we're all in this together. There's no like weird hierarchies, there's no
None of the noise that comes from being later stage or, you know, private equity backed or or you big VC or any of that. I just like, I just want to be building with cool people ⁓ that I like and respect, that hopefully like and respect me back, you know? And so it was funny, like I I same kind of thing. Like when I left, all she was like, dude, read same thing as like, why are you going to a bigger company? You could go to these big c you I was like, don't I don't wanna go to the big company. Like I I wanna go small. I wanna be in the trenches with my people.
Building and figuring out how to scale this thing. Like that's what gives me the most joy.
Adam Callinan (51:38)
Yeah, that again, same very that resonates a lot, I can't imagine. Having left that early grind, which is the best part. It's just the best part.
Ron Schneidermann (51:47)
It's the best part.
I know. I know. And that's the thing when you're in it for the journey, right? Like when you're not in it for anything other than like the experience itself, right? Like and and you really have that honest question. What gives me joy? What what part of what stage, what phase, what gives me the most joy? And then just go, go, go seek that, go get it.
Adam Callinan (52:10)
So how's Ace Lee do you been there only a couple of months or I mean less than a year? Okay. Okay. Of course.
Ron Schneidermann (52:15)
Almost a year. Almost a year. Yeah the end of the summer. Yeah, it's it's awesome. I mean, it's hard, right? It's wild.
AI so I was like I said, I was specifically looking for AI native, which meant like not just like the product itself, but like how you build it, you know, how you scale the or how you think about scaling a team. I mean, I'll I'll say this: with with 10 people, we're shipping at a higher velocity than I think anything I ever saw at Ultra.
And that's not ultras was flying. That's not a knock on ultras, but it's just again like tooling, process, even the the composition of people who are gonna succeed. It's like it's much less about ⁓ pedigree and and what you've done, more it's like a mindset, which is like curious, creative, humble, because you recognize like everything you know is out the window, right? Like I am constantly humbled, like.
Man, it doesn't matter what I did at all travels, cause like that's not gonna win here. That's just not it's just a different ball game altogether. And so I I it's just been a ton of fun learning a ton. ⁓ I've been very fortunate to be to like pull in some people much smarter than me, ⁓ who I get to learn from. I've been spending a lot of time on on hiring and and team composition and just like really bringing in bar raisers who are also like full stack doers, you know. That takes time.
but that's been like probably the biggest area of focus this first year. Just getting the right people in the right seats and then getting out of their way, letting them let it rip.
Adam Callinan (53:50)
I mean it it seems like a perfect place for AI to live. The collection of information and yeah, that's yeah.
Ron Schneidermann (53:55)
We've done well, right? When done well. Dude, because
this is the other thing I saw with my daughters like, man, there's apps where it's like you take a snapshot of your homework and it like spits out the answer. And I like, I hate this. I hate everything about this. Fuck you who built this and anyone else who invested, like, fuck you. Like this is not making the world a better place. And there's too much of that. And you know, it's like, I'm sure you've seen this, right? Like dudes working in ⁓ or you know, people working in ⁓ like social media that's that won't let their kids use it. It's like, how do you square that circle then?
Adam Callinan (54:06)
Yeah. Yeah.
Ron Schneidermann (54:26)
How do you live like that, right? Like working on things that you won't let your own kids use, but you're willing to unleash it. I've I've never been able to reconcile that ever, ever, ever. And so again, thinking through like AI and ed tech in particular is like there's two sides. There's two sides. You're either on the side of good or you're on the side of evil. It's like it's a binary thing, you know, and there's way too much on the bad side. And so again, we want to throw my time and energy at least, you know, trying to make it a little bit better. Again, something through the lens of like, again, I think it's net beneficial to society.
Adam Callinan (54:33)
I don't yeah.
Ron Schneidermann (54:55)
off what I think we can do and so, you know, I'm gonna give it my best.
Adam Callinan (55:00)
Yeah, I look forward to to watching that play out. We are we are certainly in agreement on the the world of of AI and its place. ⁓ my kids are are younger than your kids, so we're you know, at have a seven and a five year old
Trying to I mean, I'm a science guy. So like everything is about process and and be you know, applying creativity to problem solving, which AI tries to do and fails at miserably aw an awful lot of the time. And unless you know the answer to the question, you don't know that it's failing. ⁓ and trying to instill that into ⁓ spending a lot of times working on the installation process into into little ones. But it's an interesting world.
Amazing. Well we'll make sure we have show notes on on ACLE and everything. Where else do you want people to find you and find the company?
Ron Schneidermann (55:52)
sorry, it just froze. It just froze. I miss if you could rewind
Adam Callinan (55:54)
No, it's
totally fine. When yeah, when we're I'll add this in here since I'll edit this stuff out. When we're done dying up, we have to wait for it to upload if you haven't done a riverside podcast. But now the the question, where do you want people to find you and find Ace? We'll make sure all the links and everything are in the show notes.
Ron Schneidermann (56:02)
Okay, cool, cool, cool.
⁓ Ace Lee, Ace Lee dot com. Check us out. ⁓ I'm not on social media. I like my privacy. I'm on LinkedIn. You can find me on LinkedIn. ⁓ that's about it. Find me on the trail.
Adam Callinan (56:23)
Okay.
I am the exact same. I I had no social media apps on my phone for the longest time. And I made like the tactical error of adding them back in a couple of maybe six months ago to solve some specific thing. And it was immediate. I mean, within two weeks, I was like, I can't handle it. I can't do it. It's just the worst. For for me, at least, and obviously for you as well. So cheers to that. Okay. Awesome. Thank you, Ron. Thanks for all the honesty, the deep stories.
Ron Schneidermann (56:43)
Yeah.
Adam Callinan (56:53)
Again, I could spend a huge amount of time just talking ⁓ talking about all the strategy around that. So thanks for bringing it.
Ron Schneidermann (57:00)
My pleasure. Let's run it back. This was fun. This was real fun. Enjoyed it. Yeah, my pleasure.
Adam Callinan (57:02)
Yeah. Indeed. Thanks, Ron.