A Tale of Two Ruck Flops

A Deep Dive in Failure and my Entrepreneurial Journey

In the military, ruck flops are a bad thing. A ruck sack — or Bergen, as the British call it — is an oversized, often heavy pack used in maneuvers to carry personal gear around between fights. It’s a mobile home for your shoulders, and no matter how exhausted you feel, you’re expected to account for and respect your equipment while stealthily traversing dense swamps, forests, and mountainous terrain.

That being said, falling on your ruck (ruck flopping) is a quick way to piss people off, and it won’t matter if it’s accidental. You can hurt yourself, lose something valuable, or worse — alert the enemy of your presence with the loud thud of a careless fall. A mistake like this can literally “kill the entire platoon.” In this life, it’s best to avoid ruck flops, and making mistakes in general.

Ruck flops are essential for entrepreneurs, however. Stay with me here. Both intentional and accidental ‘mishaps’ can lead to exciting new discoveries and insight that might otherwise take years to identify, if ever. As a veteran entrepreneur and founder of Ruck Runners, LLC, I keep a running log of some of my dumbest ideas and ‘mistakes’ that turned into valuable insight for newfound momentum. Here are some of our most recent ruck flops — both intentional, and accidental — that are helping us keep the dream alive.

Ruck Flop #1. Don’t stock inventory nobody wants.

Background. Okay, I’ll admit it. Bro bags and fanny packs were not a big hit with my custom short shorts customers. “But they’re so awesome…” said everyone that did not actually buy one. “You need to offer these yesterday… they’re hilarious” said customers via Facebook and email. “I will definitely buy it.” In hindsight, maybe it wasn’t the best idea to stock the warehouse (guest bedroom closet) with boxes and boxes of two different sizes and four different colors of fanny packs prior to the big launch. But you know what? It was still fun as hell, we learned from it, and we adjusted.

Initial Hypothesis. Customers will actually buy additional products they recommend that I should I sell (or that I suggest). Fanny packs are huge right now. Check out my market research… WSJ

Testing. I customized and sold a couple fanny packs. Some even added it onto an existing order (insert golf clap).

Insight. Okay, confession time. The folks that purchased a custom fanny pack were mostly friends or family that felt pity for me and probably didn’t have the heart to tell me they thought the idea sucked because human beings will avoid conflict at all costs. Am I upset? Absolutely not.

On the contrary, this experience reinforced that my customers are my customers because they purchase ‘tricked out’ Ranger Panties — not fanny packs. How does the saying go, “if you try to be everything to everyone, you’ll end up being nobody to no one.” I’ve been preaching this for years. Now I’ve got egg on my face. But it’s okay.

Additionally, I’m learning how much people love to give advice. Hell, I’m guilty of this every day. The trick is knowing who to take it from and when. Opening yourself up to vulnerability by trying something new will always be a critical component of entrepreneurship. There are plenty of critics in life. “Be brave enough to suck at something new.”

Action. Okay, well it turns out these fanny packs are relatively inexpensive but effective marketing amplifiers for bulk order purchasers and brand ambassador types. I can’t tell you how many more online engagements, customer photos, and social media shares I received from folks that scored a free bro bag or fanny pack with their order. Slap our logo on there with a business card inside and we’ve got more orders coming in through a pretty clever referral pipeline without spending a dime advertising online. Does it make sense? Not really. Did it work? Yep. Plus, it’s always fun to deliver an extra smile!

Reflection. Sometimes it’s okay to try things without an ROI calculator and an Excel spreadsheet. You never know how things can turn out building a brand with a niche market product and a cult-like following. I had a boss that once told me how he felt about spreadsheets. Too often he said they “reflect an illusion of certainty.” Funny how his voice enters my mind at times like this. Also, ironic, considering I’m a consultant that builds spreadsheets and presentations for a living.

Shout Out. I have to share how much I agree with my (way more creative) friend and colleague, Mike Nemeth at Emblem Athletic, that it’s okay to pursue creative projects — even if they lose money — as long as it’s not too much. “It’s such a rewarding thing to deliver a smile.” Thanks Mike. You’re an inspiration to many.

When losing money is a good thing, with Mike Nemeth

Ruck Flop #2. Stop offering the wrong solutions to the wrong problems.

Keep it Simple. Sometimes we lose sight of what it really means to listen to the customer. It can be tempting to focus too much on our own beliefs, the tactical employment of fancy surveys, the advice of third party “experts,” or my favorite (insert sarcastic remark) — relying too much on the latest technology gizmo, gadget, or automated doo-dad to do it for you. “Sweet dashboard bro, now you can really lead your people.”

Background. At Ruck Runners, we got our start when we discovered a simple problem that others appeared to share. We couldn’t find any really cool, fully custom, personalized Ranger Panties (Silkies) that reflected what we cared about. While there are tons of great alternatives online, we chose to focus on customizing the original, iconic Ranger Panties with a full menu of accessory applications. We want our customers to reveal more by wearing less — to share their stories in comfort and in style. We started customizing our own for fun, and shared photos of our swag online to see if our idea was a “me thing” or a “we thing.” We customized kid shorts with rainbow and unicorn patches, corporate athletic shorts with safety slogan patches, and adventurous hiker shorts with National Parks patches. Right from the start, we also identified a niche market we thought we’d be better positioned to serve — military families and veterans.

Initial hypothesis. Military families and veterans stockpile extra unit patches, badges, tabs, and memorabilia over the years that end up unused, laying around, collecting dust in unpacked moving boxes and desk drawers around the house.

While shadow boxes are classy (and expensive), what good are great memories and stories if they sit static behind another glass box at home with no one to share with or see them? I remember sitting quietly in my own home office alone one day, staring at several 1st Infantry Division patches in a drawer. I didn’t know what to do with them, but I couldn’t throw them away. I felt like I wasn’t just holding a patch in my hand, but an item that represented thousands of people, great stories and fond memories from the first unit I served with in combat nearly 14 years ago. The “Big Red One.”

Testing. Within the first month or two, we decided to focus on sewing unit patches and tabs on an already iconic product — Ranger Panties — for military, veteran, and law enforcement customers. More requests started pouring in through social media inboxes, website and email accounts. “Can you add a sapper tab to my shorts?” Friends of friends I’d never met before started asking for my Venmo account info promising to send cash if we could “just find their regimental affiliation patch” for an order. Wow, pretty cool right?

Yeah, but kind of expensive and time consuming with all the logistics. I found myself constantly searching for, purchasing, and shipping product inventory while also locating, purchasing, and shipping requested accessory items to my house. Then we’d sew each customer’s requested accessories onto their requested sizes and colors of shorts before shipping the complete package back to them (this seems completely crazy after spelling it out this way for the first time). Giant-sized $20 patch requests started destroying my margins. After a few weeks of this chaos, the voice in my head finally whispered, “this must be why nobody else does this.” My perspective again had to shift. Okay, how do we prevent this from becoming an expensive hobby? I felt stupid. I’d finally found something awesome that people wanted, but couldn’t form a business around it… yet.

Insight. This brings up a key point. Starting a new business is completely different than improving an existing business. Sometimes you have to see if something can be done at all before you worry about improvements. If it doesn’t work, change something quickly, or get rid of it and move on. Don’t stay wedded to an initial concept or idea. A Minimum Viable Product (MVP) mindset is gold. Welcome to entrepreneurship!

Action. Another “aha” moment. Let’s outsource the work, or at least some of it. Allow customers to purchase their own patches and memorabilia online and have them shipped to my UPS business address (thanks Amazon). I’d still keep a few patches and tabs in stock for our most popular requests, but now I’m only responsible for supplying the shorts. Cost of Goods just went down some more.

Sweet, only here’s the catch. This was my solution to my own problem, not the customer’s. Guess how many folks mailed me a patch in the next month? I’ll give you a hint, not enough. They still insisted that I find items for them, completely ignoring my website explanation of “the rules.” Rather than playing the victim here, I realized I was seriously starting to confuse people, including myself.

“I am not the market,” the voice in my head said again. My initial hypothesis might not be wrong, but it was definitely incomplete. I left out the part where I assumed all my customers would actually provide their accessories to me, either by personally mailing them, or by purchasing and shipping them to me online. Once again, I felt stupid, but continued to drive on.

It’s a humbling experience to receive direct feedback in the form of silence from your customers. But you can’t let it hold you back. What did this temporary setback lead us to discover next? Before you read on, scroll up and re-read the first paragraph of Ruck Flop #2 again, “Keep it Simple.”

Reflection. Not too long ago, we started offering custom stretch vinyl decals to supplement our existing patch application sales in a small, much more controlled manner behind the scenes. “This might be cool,” we thought initially, “if we could figure out how to do it, and then do it well.” We wondered what kind of customer might gravitate towards this additional application alternative. Not much time transpired when we began thinking that maybe we were focusing on the wrong solution to the wrong problem with respect to our original sew-on, patch and tab accessory application initiative.

At this point, we had almost 100 sales logged. Not long before, I remember how incredible it felt securing our first customer. All I wanted to do initially was to see if just one person would actually buy and appreciate something I had to offer, without returning it. Translating an idea into willingness to pay is a glorious experience for any entrepreneur. Tell me you don’t remember your first customer and I’ll call you a liar.

More Insight. As we looked over previous purchase orders, a clear picture began revealing itself. More decal orders piling up. Like, a lot more. Additionally, we could see categories and sub-categories of the types of requests for online decal orders. In fact, our customers started to show us problems our products were solving that we didn’t even know existed. For instance, vintage unit patches, crests, and logos that have either disappeared completely or relocated accounted for a noticeably high volume of decal orders. That’s strange, we thought. Another “Aha moment.” Military and veteran customers were wanting to reconnect with the units and memories of loved ones.

This made sense. Military service is becoming more and more generational in time. I served as an Infantry Officer in the Army (OIF), my parents both served in the Air Force (Cold War/Desert Storm), two of my uncles served in the Army (Korea), and my grandfather served in the Marines (WWII/Korea). Most people don’t realize this, but 91 divisions were formed by the U.S. Army alone in WWII, compared to only 10 active divisions today. If a division contained at least 15,000 troops, that means that over 1.4 million WWII Army veterans shared stories and memories with their children and grandchildren.

Many of our military and veteran customers fear the loss of these memories as America’s Greatest Generation slowly fades away. We’re helping loved ones connected through service to keep these memories and stories alive by wearing and sharing them openly with the world in a fun, upbeat kind of way. While customizing short shorts might seem a bit crazy, our mission to Reveal More is dead serious.

More Action. Pivot the business to cater to a narrower customer base while providing targeted offerings that alleviate more severe pain points.

Reflection. We remain in a constant state of transition in business. While this might seem obvious, I found myself stuck in an earlier phase we were no longer in. I kept pontificating about what my potential, theoretical, future customers might want. By observing the behaviors of my actual customers, I began to discover new insights, problems to solve, and solutions to test. I have no idea where we might end up, but am hooked on this process of discovery that so appropriately defines the entrepreneurial journey.

Shout Out. A mentor of mine, Benjamin Campbell, once shared why he loved business so much. “It’s the only place in the world where new value can be created out of nothing.” It defies our laws of physics. This can be a beautiful thing.