AYF/GF 128 | Snowmobiling Trip


The most important business lessons are found during the most unexpected time. For Merrill Chandler, he found an inspiring message in one exciting yet chilling snowmobiling trip. He shares how getting stranded in a snowy ravine within the mountainous areas of West Yellowstone taught him to avoid overconfidence and overestimating his skills. He also talks about how this singular experience pushed him into crisis management mode that tested his survival, making him realize the importance of evaluating risks over rewards.

Watch the episode here:


Listen to the podcast here:

Snowmobiling, Search & Rescue, And Business

This episode is a lot of fun. It’s another example of me learning lessons the hard way. I’m going to discuss the risk versus reward, and another situation where I cameout of it by the skin of my teeth. I learned insane and mad life lessons about how terrain versus maps, over-estimating your skillset and more importantly, the danger of perceived experience which in my case was arrogance.


In this instance, I’m going to be sharing an insane story. It could have been a life-threatening story had we not taken care of some precautions, but I was trying to dig myself out of the hole I put myself in. Let’s get started. I’m embarrassed but I will never sell you out. I’ll tell you the truth, the whole truth and nothing but the truth. We’ll sort through the shambles of my life and come home with how do we learn from my experience and how do we avoid our own landmines. I love snowmobiling. I’m up with family and friends and we are having a blast all day. It’s in West Yellowstone but not the city. There are a bunch of great mountains to the West of West Yellowstone City. We’d spent all day up in the hills sledding at about 3:00 PM or 4:00 PM and it’s getting dark. It’s wintertime in the Wyoming, Yellowstone area. It’s about 4:00 PM and we’re headed home back to West Yellowstone to get in the hot tub, have a great meal and regale the tales of the day. That was not what happened.

Dionne is one of the key men that blew up Lexington. It seems like the last couple of episodes have been about my old school friends. We talked about the cofounders of Lexington and our adventures down in Chiapas in Southern Mexico. Another one of the key men or founders who are responsible for blowing up Lexington back in the day is Dionne, a dear friend and an amazing man. Nothing but great things. You know how sometimes you have a great relationship where one of you is the gas and the other is the break. Between the two of you, there’s usually some version of choosing deliberately where do you want to go and what you want to do. There’s an element of closure or at least some checks and balances. Not with Dionne and myself. I’m the gas and he’s the nitrous. He was always, “Hell yes.”

We’re on our way back and we spent 3 or 4 days sledding, and there are thousands of acres of beautiful mountains to go explore and trail the meander. The three previous days, every time we were on our way home, we saw this little exit. It was the road and then later on, the train tracks that go into town. There’s a 5-mile town, which is a long way on sleds. If you go down, we’re about 5 miles out of town on groove trails and forest service roads. It’s cool all the way into town. Dionne and I have been looking at each other and we know where that ends up. The train tracks go into town. We want to try the train tracks.

AYF/GF 128 | Snowmobiling Trip

Snowmobiling Trip: The reason why there are coaches is for you to talk to somebody who has turned around, did not shoot the gap, and how to win as a result.


It was the last day and we’re like, “We’re going to head here. We’ll meet you in town.” We believe that it was going to be a shortcut. It would be shorter because the trails meander all the way around another hilltop. Before you get into town, there’s a hilltop or a mountain. As the dusk was settling, you can see the glow of the lights of town. That glow of the lights was right above these train tracks. It had been snowing for 20 to 30 minutes when we decided, “Let’s head down and follow the train tracks.”

Initially, there was a service road next to the train tracks but pretty soon, we had to pop up onto the train tracks. There are 2 feet of snow on top of these and there were no recent sled marks. We were on top of a foot of snow or maybe a little more. We were grooming our own trail. We’re experienced sledders. We’ve been doing this for years at this point. It was an adventure for us. We were like, “Let’s blaze home. We’ve never done it. Let’s head down here.” We’re probably a mile into this trail and it’s a piece of cake. This is the first warning sign. If something is a piece of cake and you’ve never done it before, that means that something might be coming at you later on to make you think twice.

We’re cruising along and it’s beautiful. I can’t even call it a canyon. It’s more like a gorge and sometimes as small as a ravine. We are cruising 30 to 40 miles an hour fast. That’s fast on a sled. We’re cruising and nothing is in our way. We’re having the time of our lives. We’re staying on this trail and think of train tracks anywhere in a mountain setting. The mountain was on the left-hand side. It planed out for about 10, 15 feet where the train tracks were. It then went over to the other side of the ravine and up. We’re in this little ravine cruising. We started noticing that the ravine started to create a dip on the right-hand side and it became steeper and steeper.

We’re now on a cliff riding along the “railroad track trail.” The further we went, the steeper the ravine. We’re like, “It’s not worrisome because it’s flat, we’re on fresh powder and cruising along the tracks.” There were probably 60 to 100 feet down the right-hand side of the trail, whereas when we started out, it was just train tracks in the middle of a ravine. It started creating this huge ravine down below us to the right. We’re cruising along and we stopped. We walked to each other because it’s only like 10 feet wide. We stopped and we’re like, “What do you think? Do we turn around?” “No, we’re good. This seems good.”

It’s flat terrain on the train tracks. The train tracks are likely not to have a landslide or something, so no harm, no foul. We’re back on our sleds and we slowed down a little bit, but we just headed out. We’re a mile in. These distances are far on a sled in powder. We keep going and then up to the far right. It was snowing. The visibility was 200 yards and then we saw that the train tracks crossed a culvert. A culvert is where there’s a creek down at the bottom. It was a metal culvert. It’s a corrugated metal pipe that the tracks went over before it continued. Now the trail was on the right, not on the left of this ravine that was now down to our right.

If something is a piece of cake and you've never done it before, something might be coming at you a little later on to make you think twice. Share on X

We could see it a little way up. We’re like, “It looks like we’re going to cross.” I’m sitting here going, “If this train crosses this culvert, then there’s going to be nothing to the right of us or the left of us.” It’s getting fill in the willies. This is all adventure because it was a straight path and 10 feet. That’s plenty of room on a sled. We’re like, “We can do it.” We keep going down and then about 25 to 50 yards before the track started across the ravine, there was the earthen barricade where the culvert let the stream flow under it. We ran into an avalanche. The avalanche sounds super huge. It was a snow slide about 10 feet wide, no sweat.

The snow was a straight angle across the train tracks into the ravine and then disappeared where the ravine was. The ravines were 50, 60 feet, maybe more in-depth, but there was no straight path through that snow slide. Three opportunities presented themselves. The first was to go dig out the 10 feet, make it flat trough and through. The second was to turn home, go back a full mile and change, then go the 5 miles home. It’s snowing, we’re cold, and we were anticipating this being a shortcut. Psychologically, we’re like, “We want to get home as quickly as we can. We don’t want anybody worrying about us.”

The third option was to shoot the gap. Shooting the gap has never been a problem. It’s super easy. It simply means that you hit the slide and head up the slide a little bit and then you go down the other side of the slide. Remember, the slides are only 3 or 4 feet high. It’s not a big deal. I don’t want to make it sound more ominous than it is, but you shoot the gap, you go high and come down. There are 10 feet on the other side, plenty of landing space, and we would be able to continue on our way. As the gas and nitrous pair that we were, we do this all the time. We shoot gaps more in open space.

It’s like you go high on a hillside, turn around and come back down. We have plenty of experience. Ten feet is no distance whatsoever. The problem was that there was a 50, 60-plus ravine on the other side should we miss. We stopped and looked at what the up angle would be as we crossed. We also looked down over the ravine. There were no trees, no rocks, nothing. It was just snow down to the bottom of the ravine. We’re thinking, the worst case is if we go down, then we shoot back up this ravine with plenty of run-ups to get the momentum we need to get back up on the trail. We’re like, “This is cool. This will be fun.”

We decided to shoot the gap. I’m in front. I have the opportunity to shoot the gap first. We’re equally good sledders. I’m sitting there. I probably have 10 feet in front of the snow slide. It doesn’t take much to get going. I’m thinking I’ll shoot up 6 to 7 feet high on the slide and then come down on the other side, then there will be tracks for Dionne to be able to lay in and it’ll even be better. No harm, no foul, we’re just going for it. I’m like, “See you in a second.” I put on my helmet. I’m turning the engine. I just peel out and shoot it perfectly. I shoot up the slide, except the slide was loose.It was just powder. The slide itself was loose snow. If you would’ve seen it on TV like the funniest home videos or any of these craziest human errors, the videos you see on YouTube or otherwise, I hit up at the top.

AYF/GF 128 | Snowmobiling Trip

Snowmobiling Trip: Whatever your jam is, make sure you have the presence of mind to know the consequences in everything.


As I’m accelerating through, I slide down the slide. One of my skis catches the edge of the 10-foot clearing. I missed and head down the ravine. I didn’t flip it. I didn’t do anything but I’m all the way down the ravine. The second mistake is Dionne was like, “I’m going to get on the other side and then I’ll throw you a rope. We can get you up on the other side and we can continue down.” None of you sees the error of our ways, but thinking that it might be a little more packed since I already went up, Dionne shot the gap. He ended up exactly where I was.

I didn’t try getting out of the ravine before he did it. We’re thinking, “This is easy, no harm, no foul.” It’s continuing to snow. It was a huge snowstorm. It snowed all night long. We’re in the ravine and there’s a creek down but it’s iced-over where we’re at. We pulled out and we shot up that 50, 60 footers and we get so close within feet off the top. We weren’t going forward. We wanted to go backwards and take a long way home. We were coming within 5, 6, 7 feet of the top but we could never get up that last bit. We were mad and scared all at the same time because we kept revving the engine. We go up and down.

We thought the more we did it, the more we would create some stick for our tracks to get ahold of. The further we got up the hill, instead of cresting and going over the top onto the railroad tracks, our skis were sliding down the hill and we could not get up. We’re sitting there looking at each other going, “What the hell.” We spent half an hour trying to get back up the erstwhile trail. It was not happening. This is no bueno. It is snowing like mad. We are stuck at the bottom of this hill. Our whole party knows where we went, but they don’t know how long it takes for us to get home. They know that we’re adventures and we’ve been night sledding dozens of times.

Crisis Management Mode

We picked up radios every trip thereafter, but we didn’t have radios at that time to notify where we are and what we’re doing. There was no notification. There’s an easy assumption that “They’re fine. They’re just sledding.” We didn’t know how long we were going to be in this predicament. I went into crisis management mode. This became an adventure even though it was stupid circumstances and poor choices. I went into survival skill mode. There’s a term for conifer trees, pine trees, etc. They call it a horrible term. I don’t know a better way to call it.

I was raised that when the native Americans would go out in the snow, they would be able to pull off all the pine trees. They would lose their needles and the branches would start falling downward. No snow could penetrate it. It didn’t hold snow and water would run right up. They were always dry and you could create a fire. I started harvesting all these twigs and branches that would snap just like that because they were dead. In the middle of the snow, they weren’t wet to be able to make a fire. Here’s the fun thing I’m going to tell you that I’m proud of. We didn’t have any survival gear. All foolish decisions all on their own, but no time for that. We didn’t have a lighter or anything. We’re sitting there. We know how to gather wood and the stream that was going through the culvert that we were supposed to cross and continue on our journey, there was a culvert where we could get out of the rain.

Many people want a thrilling adventure but don't really consider the upside and downside. Share on X

The snow was about 5 feet tall so the water could go under this railroad bridge. The creativity juices were flowing. What we did was we took one of these branches and dipped it into the gas tank and then use the toolkit for the sled, loosen the spark plug, and then hit the ignition so that the sparks would ignite. We lit the twig. I’m very proud of that. The twig lit the gasoline. We took that burning branch over to the culvert where we set up a fire and began to hunker down for we had no idea how long in the night. The final preparation that we did to try and think ahead was since our group knew where we were but didn’t know how far along this path. When they decided to tell somebody about us missing, we want them to be able to see us.

It was snowing badly. We decided to park one of the sled that had half a tank or more of gas. We put one of the sleds, turned it on, and had the lights pointing right up so that they were lighting up the snow falling and the trees above the railroad line. The visibility when it was good was only 100 yards. They’re going to have to get pretty close to us in order to help. We had one sled face up illuminating the trees above the railroad tracks. We kept the other one. We would be able to light the fire more if we needed to with the gasoline and the spark plug. There we sat.

Dionne and I have been on all kinds of adventures together, but this one was one of those like a dead pool, “How long do you think this is going to be before they start looking for us or before they find us?” There’s the idea of, “They’ve been gone too long,” then “Have they been gone too long? We need to talk to somebody,” and then there’s finding somebody, explaining the situation and giving them a decent idea where we are, then the time it takes to leave town to come and find us. “They’re probably okay. Nothing like this had ever happened before.” We hadn’t ever been stranded or anything in sledding. It took approximately six hours. We got stranded at 6:00 PM. We got down there and everything. From 6:00 PM until about midnight, we were in this culvert. We had a fire and had to sit low because the smoke was coming up to the culvert, and then it was going out or going along that. It wasn’t comfortable. It was miserable. We were cold, but we had a fire. We got to talk and shoot the shit and do our bro bonding.

Rescue Team

At about midnight or 11:45 PM, we heard the sounds of other sleds and they were coming the exact way we did. Here’s what’s embarrassing. First of all, the search and rescue team, two of the sled just come over the side down into the ravine, grab our sleds, and ride them out. We are experienced sledders and we spent half an hour trying to get it. They brought their sleds down and then got on our sleds and circled back to the creek to get a little running distance right up on top. It’s the first time for both Dionne and my sled. It’s embarrassing and miserable. We’re cold, hungry and worried. At this time, we feel better but for six hours, we have no clue. Are we going to walk out tomorrow morning because we had a fire? We didn’t want to walk out at night. During the day, chances of survival are much better, especially on a 3 to 5-mile hike in the daylight. It’s way better than in the snow at night. We decided to hunker down until somebody found us or daylight came. We’d have to leave our sleds and hike out.

Search and rescue would still have to bail us out or the rental crew. The bottom line is they snap those sleds right out of the ravine. We climbed up the hill manually. There were search and rescue and two in our party came to make sure we were okay. We’re humiliated, wet, tired and smoky. We head back with the way we came. Another mile or 1.5 miles to the main road and then 5 miles. At midnight, 5 miles is a long ugly ride when you’re cold, wet and hungry. I’m just embarrassed.

Arrogant And Comfortable

AYF/GF 128 | Snowmobiling Trip

Snowmobiling Trip: If a guide could show you adventurous ways to get that thrill, it won’t cost you a fortune.


Why do I share this? You guys already know where I’m going with this because this is stupid. First of all, where in your life did you say, “This is easy,” and get arrogant or comfortable in doing deals, making loans or in private lending? How many loans have you done? “I can’t fail. This is awesome. I’m not having any problems because whoever trained me gave me the tools.” All of a sudden, we get arrogant and sloppy. We think we are invincible. We are not the Marvel Universe superheroes. We are not invincible. Where is your arrogance ended you up 60 feet down a hole with no way out and you had to get support to climb out?

Another thing. Were there other things that I could have done when I was going to shoot the gap? Were there other things I could have done to establish whether or not this was a safe move? Yes, but my arrogance and my supposed skill had a huge blind spot for how skillful I was, which later turned out that I have no skill whatsoever. The search and rescue guy drives our sleds out of the ravine the first time. I got no skills comparatively speaking for self-survival, then I’m making a decision to shoot the gap. Did I go up and see how strong or how solid the snow was? No, I didn’t look to see what the ski fall as well. Was it just snow or was it pebbles and rocks? The rocks let go above and were part of the slide. I didn’t even check.

That’s what was part of the problem. It wasn’t just snow. It was a rock slide and dirt slide underneath the snow. This cost me over $1,000 to get us bailed out. The families that we were traveling with are like, “We’re not paying this, you idiot.” Did I do any of the math? What happens if this is the worst-case scenario to see what is that 10 feet? My arrogance goes through and through. My arrogance was, “I got this. I’ve done this a dozen times.” I hadn’t done it a dozen times. I’ve shot a dozen gaps on the side of a mountain where I wasn’t going to fall off into outer darkness by the time I finished.

Risk Versus Reward

It’s the risk versus reward. I was overestimating my skillset. I thought I was the bomb on a sled. Do I have survival skills? Yes. I’m Mr. Eagle Scout here. I can camp three days in the snow with the lighter and certain provisions. I’ve done it before as an adventure, but I went and planned in those examples. Here, I was clawing through because if I couldn’t have created fire, hadn’t been able to do the math and didn’t have that kind of experience, we would be sitting in a culvert freezing our asses off with no fire and no light, nothing. We weren’t prepared. We didn’t have flashlights in our gear because usually we head home in daylight. We didn’t have anything. There was a tool kit in every sled so that we could ratchet off the spark plugs and create a spark for the twigs that we had put in the gasoline tank or dipped in the gasoline tank.

Here’s the other thing. Did we have a guide? Did we have somebody who had traveled that? “I’ve done it fifteen times. Let’s go do the railroad tracks home. We had a map of the area. We knew where it was headed.” We had no idea what the trail would look like and how to counteract the contingencies that we ran into of deep snowing, deep ravines, rocks splash snow slides, and arrogantly tooled along. The terrain we encountered was not on the map. Guys, what have you done in your personal life, especially for our purposes here in our business life? How do we cavalierly go running into the burning house without a plan? While you’re reading this, how many mistakes can you recount that we can list on our mind saying, “I didn’t pay attention to this. I didn’t plan for this. I thought the map was the terrain. I had no clue how to handle this.” We lose money, our lives or our loved ones’ lives and put them at risk.

Believing too much in yourself leads to an overestimation of your skills. Share on X

My take-home message here is easy. I thought I was better at something than I was. Since I wasn’t talking to anybody about what was in my blind spot, I was counting on my arrogance. My decisions were based on my arrogance and the overestimation of my skills. I’m the guy who’s always talking about leveling up. I’m the guy who’s always saying, “Don’t get down on yourself, plan well and take intentional risks with a proven model.” I don’t teach, share or encourage to willy-nilly anything. Part of it is because I’ve learned through horrible experiences like this that I cannot afford that the downside is so much worse than the upside.

Think of it in this context. What was my upside if it would’ve worked out? I would have shot the gap and come along there. Let’s pretend that the bridge wasn’t out, there weren’t more rock slides, or it was peachy into town. My only upside was we found a new trail. We took some risks and it paid off. That was the only upside. We live our lives through adventure. Many of us live our lives that we want adventure and those thrilling moments, but what’s the upside? In this case, the downside was $1,000, misery, and the opportunity to share an embarrassing story. This could sound like I could share this story over cocktails. When I get honest with myself, this was stupid. It’s straight stupidity.

In everything that we’re doing, how do we overestimate our skillset? How many of us have done well so often that we play fast and loose to our own detriment or a significant loss? How many of us think that just because you’ve gone to real estate school, you have a private lending guru, you’re doing business lines or you got a business, you think the map is the terrain? They gave you a map. The reason why there’s a coach there is so that you can talk to them about somebody who has turned around, not shot the gap, and how to win as a result. In fundability™ and optimization of your borrower profiles and all those things, we can talk about having a guide that supports you.

The bottom line is don’t do these if you don’t know the terrain, not the map. Everybody thinks they got the funding map out there. It’s full of landmines as we’ve learned from previous episodes and as we’ve learned from my Bootcamp and in my book, The New F* Word. We think the map is the terrain and it is not. I encourage you to make sure that whatever you’re doing, if it’s with me or out there in the world, improving yourself as buy and holder, fix and flipper, private lender, hard money guru, whatever your jam is, make sure that you have a presence of mind.

Think of the logic. There’s a railroad track going into town. Here’s a railroad track. This railroad track must go into town. Even that could be an error in judgment. I’m certainly not saying don’t have adventures. I’m saying make your rewards worth the risks that you take. Make sure you have a guide. That would have been such a fun trip if a guide would have been able to show us more adventurous ways to get that thrill that doesn’t cost us a fortune and humiliate us in front of our families. We’ve never lived it down ever. It’s still a thing. That’s the message in this episode. Is it worth it? If it is, then make sure you have a plan to navigate the terrain of your life. Not just say, “I got a map.” This is Merrill Chandler, your host of the Get Fundable Universe and it’s my job to make getting you funded easier.

Important Links:

Love the show? Subscribe, rate, review, and share! http://getfundablepodcast.com/