Fires and Questions: Recent Mistakes and my Takeaways

I read an interesting view on mistakes versus failures in Ross McCammon’s, Works Well with Others. He suggests that failure is a purely negative outcome while mistakes offer opportunities for growth. 

About six months ago I made some mistakes, and four months ago, I paid for them… big.
I won’t go into details, but instead leave it at, December and January were far from stress-free. 

As things cooled off I was able to reflect on what happened. Where had I gone wrong? And once the chaos ensued, how could I have handled it better?

After weeks of mulling, I boiled my missteps down to two major takeaways: ask questions and know when to power through.

Ask Questions
I’ve never been good at asking clarifying questions. My default is to work things out myself. There are times when 'going it alone' can be constructive. Yet those instances are preceded by context and an understanding of the framework within which you’re working.

Without that context, you’re operating off of a set of assumptions that may or may not be correct. Even when launching a startup, it's imperative to understand the basics: the industry you're entering, the problem you're solving, who your customers are. Asking stakeholders clarifying questions can inform a rudimentary framework, within which you can construct a business.

The framework can change over time, but you'll always have a context for your work.

In an established company, there’s likely a framework already in place. If you're hired to improve a facet of that business, you first need to build an understanding of the institutional framework.

Why are we currently doing it this way?
What is most valued by our customers? By senior management?
What major issues have you seen in the past?
What is the long-term goal of this initiative?
The list goes on and on.

These types of questions are precise and probing, meant to shed light on the framework at play. The more you know, the more you can improve your facet of the business. 

I made mistakes that put my co-workers and I on a crash-course with the Christmas season. If I had asked probing questions early and often, it's likely we would have escaped the holidays with fewer bruises. 

So… Never shy away from asking questions to understand the context of your work. Both you and your business will benefit. 

Know When to Power Through
There are times for reflection and there are times for action, and It’s rare that those two times coincide with one another. Recognizing times of action is easy. Resisting inopportune moments of reflection proves more difficult. 

It's human nature to seek an explanation for how we’ve ended up where we are. If something positive happens, we want to know how to promote more positive outcomes. If we experience a negative outcome, we want to understand how to avoid the same pitfalls in the future. 

When the mistakes of the prior months came to bear, I wanted to know what caused the chaos. Everything had looked so promising, so how did reality become far removed from the holiday game-plan? 

I poured over potential missteps, searching for the culprit of my work-life pain. The reasoning was, if I could pinpoint the underlying cause of the fire we were fighting, I could stem its spread and the holiday season could be saved. 

It's an attractive theory, but in practice, that approach is doomed to failure. 

To continue with the fire metaphor, the time to search for the ignition source is not when the house is on fire. There will be plenty of time to find the source of the blaze once it's put out. 

Inopportune reflection is, at best, a waste of precious time. At worst, it can be cripplingly counterproductive. 

So… If there’s a fire, put it out. Reflection and longer-term improvements can come after you’ve powered through. 

The Wrap-up
These takeaways are not groundbreaking. They could even be categorized as common sense. Yet it took stumbling headlong over both to ingrain them in my consciousness for good. 

My mistakes have made me better at what I do. So I implore you, make mistakes early and often, give questions the same treatment, and always have your extinguisher at the ready. 

A Modern Discovery of the Great American West: Part I

One Hell of a Day in Yellowstone

We woke up before dawn to snow piled high on the rainfly of the two-person tent we were to call home for the next three weeks. It was our fourth day of the 4,000-plus mile journey that would eventually take Keira and I across the American West to seven National Parks and ten states that included Colorado, Wyoming, Montana, Idaho, Washington, Oregon, California, Nevada, Arizona and Utah. Unknown to us at the time, the experiences that lay ahead were numerous and life changing, but at that moment, taking down our tent in the frigid cold, we were over it.

Our first three days in the northwestern reaches of Wyoming went as follows:

DAY 1
·  Arrive in Grand Teton National Park
·  Setup camp at Jenny Lake
·  Meet George the Elk (George = awesome campsite companion with zero respect for personal space)
·  Hike around lake, eat dinner, sleep
·  Weather: Rain

DAY 2
·  Drive north to Yellowstone National Park
·  See near-roadside sights on way to Grand Canyon of the Yellowstone
·  Hike south rim of canyon
·  Setup camp, curse at RVs with generators, sleep
·  Weather: Rain

DAY 3
·  Do touristy “must-sees” in Yellowstone: mud volcano, fishing bridge, old faithful, Mammoth     Springs, etc.
·  Hike
·  Setup camp outside of Mammoth Springs
·  Become terrified of protective mother elk, eat, sleep
·  Weather: Rain

As we took down our nylon home in the snow, we could do nothing but hope the day we had planned would offer some consolation for our current luck with Yellowstone's weather. Our plan was to drive out to Lamar Valley – the Serengeti of the West – to see bison, elk, moose, wolves and, we hoped, a damn bear (there is a rant here that I won’t go into). After oo-ing and ah-ing over Yellowstone’s mega-fauna, Keira and I were going to return to Mammoth Springs and go on another hike to a spectacular overlook where we would hold hands whilst reminiscing about all of the incredible things we had seen thus far. That was the plan.

After taking a wrong turn and having a near miss with a watermelon-sized boulder tumbling off of the mountain above the snow-covered road, it became evident our last day in Yellowstone was destined to be an adventure, whether we wanted it to be or not.

Keira and I spotted everything from elk to coyotes on our journey through the famed Lamar Valley, but still both bears and wolves eluded us. Feeling a bit disillusioned with animal spotting, we decided to go on a hike. It was snowing, but our yearning for physical activity convinced us to go on a quick, three-mile jaunt up to a pleasant meadow overlooking Lamar Valley. 

After dodging horse shit and speaking loudly about our future plans for a half an hour – apparently bears don’t like human conversation – we arrived at the snowy meadow. Unsatisfied, and aware of the existence of a second meadow a mile up the trail, we pressed onward until a large bison standing firmly in the middle of the trail abruptly halted our progress.

It’s important to note that bison are not uncommon in Yellowstone; in fact, if you have a working set of eyes its damn near impossible to visit and not see one. Having been desensitized to their presence, a bison standing 100 feet from us on a narrow trail with a flooded meadow on our right and a steep hill to our left did not immediately set off any sense of panic. It should have.

I have never seen an animal eliminate “flight” from the fight or flight response so quickly. Suddenly 100 feet seemed too close for comfort. Keira and I began to back up slowly as the bison began to walk forward slowly. We began to back up quicker, the bison picked up its pace, steadily closing the 100-foot gap. As this jockeying continued for a few more seconds, it was revealed to us that this bison was not alone but was just one of a herd of bison; a herd with newborn calves, calves they are very, very protective of. We break into a power walk, agro-bison decides to trot, and now we turn around, face downhill towards the car, and run.  

Our escape was successful, I assume because our puniness was made obvious to the bison and thus not worth his, or the herd’s, time. After dodging horse shit again and speaking loudly, out of nervousness instead of bear encounter prevention this time, we made it back to our orange chariot having survived our first truly sketchy encounter with Yellowstone mega-fauna.

We continued down the road to the eastern end of Lamar Valley and pulled off at an area called Pebble Creek. Keira and I tag-teamed cleaning out trash that had built up in the car, re-organized things and relieved our patient bladders. Ready to get back to Mammoth, go on another hike and setup camp for our last night in Yellowstone, we fired up the car and started driving. We got ten feet.

SCREEEEECH-WANGTANGTANG-SCREEEETCH, “Shit!”

It sounded as though the drive shaft sheared and was grinding against other important metal objects necessary for the operation of my car. My heart sank. All of our plans, the sights we would see, the experiences we would make, the hope of ever seeing those places and experiencing those things vanished with one wretched noise.

SCREEEEECH-WANGTANGTANG-SCREEEETCH, “Son-of-a!”

A man named Bill – the only other living soul around – pulled up in his ‘Merican made, diesel-power-plant-on-wheels and asked if we needed any help, adding at the end of his inquiry, “sounds like ‘ya ‘gotta pebble in ‘yer brake.” Taking note of that bizarre bit of op-info I asked where the nearest ranger station was. With simple directions received, Keira and I made our way three miles back towards Mammoth to a satellite ranger station in silence, aside from the ear-piercing screech of my car slowly dying – we presumed.

Ten minutes, and countless terrified creatures and their respective pissed-off human observers later, we arrived at the ranger station only to find out it is no longer a ranger station, but rather the springtime home of one very pregnant woman.

SCREEEEECH-WANGTANGTANG-SCREEEETCH, “Sounds like a pebble in your brake, I had that same problem once,” she says after bearing witness to the noise my car continued to make.

“So how do I fix it?” I ask.

“Well, you could risk driving on it and hope the pebble dislodges itself. Of course if it doesn’t fall out soon enough the friction caused by the pebble could heat up your brake and split it,” She continues, “Your other option is to take the tire off and see what’s back there.”

“I can’t do that,” I explain, “my tire lock was stolen.”

I stared at her, and she at I, silence fell over the three of us. “I’ll call a tow truck,” she said, conclusively.

Keira and I sat in the car, heat on high, audiobook blaring through the crippled car’s speaker system. Two hours later, the tow truck arrived from Cooke City, fifty miles away.    

“Sounds lika pebble in yer brake,” he said with half-confidence. “You try takin’ the tire off?”

“Don’t have the tire lock,” I say.

“Hmmm… well let’s lift up the front on the back-uh-my-truck here,” he suggests, lowering the hydraulic lift gate of his weathered truck.

Being the last resort before having to get towed fifty miles away in the snow, I agreed, drove my front tires onto the gate, helped him secure the car and lift the front end up. Crawling underneath I finally got a view of the problem area. Behind every brake pad there is a piece of low-gauge metal that protects the brake pads from dirt and grime. What I saw when I crawled underneath my car was that piece of metal warped and misshapen. I explained what I saw to the tow truck operator in a half question.

“Oh!” he exclaimed, reaching into his toolbox and pulling out a standard screwdriver. He kneeled, eye-level with the outside of my tire, and began poking on the small flange of metal barely visible from his vantage point, and worked the warped piece of metal back into its original shape. After only a few seconds of doing this, a pebble half the size of a pinky nail falls out, landing with a clink on the inside of my wheel.

“Fixed!” he proclaims.

He lowered the car back to the ground, I got in, put it in reverse, and sure enough, silence. $327 and a face-in-palm moment later, Cooke City Towing’s finest rumbled off in his battered tow truck, leaving Keira and I to stare at the innocuous looking pebble I held in my hand.

With a mixture of embarrassment, anger, and relief, we put the car (now dubbed Murphy) in drive and quietly rolled back onto the main road, due west.  Sick of snow, large animals and most of all, pebbles, we set a course for Portland, Oregon with the promise of good beer and a bed only fifteen hours away.

Next in Part II… Portland, Highway 1 and the Yosemite death march. 

Call Me the Fly on the Wall

A lot can be learned when you shut up and observe impressive people do their ‘thing.’ I know this because I did just that last week when I had the pleasure of sitting in on Techstars Boulder’s highly confidential screening committee

Every year, hundreds of entrepreneurs apply to be a part of the coveted Techstars Boulder program. From those hundreds of applicants, only 45 make it to the second round called screening committee. Its screening committee’s job to listen to each of those 45 entrepreneurs pitch their businesses and ultimately choose 10-12 to participate in the Techstars Boulder accelerator program.

If you’ve seen the show Shark Tank, it’s kind of like that, but more badass.

So there I was, sitting quietly in the corner, making sure all of the product demo videos and conference calls went off without a hitch.  In between trying my best not to screw up my job in front of respected movers and shakers in the Boulder community, I was able to observe a process that only a handful of people have ever seen in full.

I sat, I listened and I learned. The process for each team was the same:

1)   Arrive at Techstars Boulder 20 minutes before your scheduled time to pitch.
2) As your time draws nearer, you are brought from the reception area to a conference room and ultimately to a set of couches.
3)  1 minute before your scheduled pitch time, you are escorted next to the room full of screening committee members – Boulder Venture Capitalists and Techstars staff – sitting in a semi-circle watching your demo video.
4)  S**t bricks.
5)  Walk into the room, say a quick hello and start your 4-minute pitch, followed by 5 minutes of questions from the committee.
6)  Done. You are whisked out a back door into a hallway, have your picture taken with a life-size cutout of Chewbacca and then you’re shown to the elevators to take you downstairs and out onto Walnut Street.

After hearing 45 pitches and the subsequent comments from the screening committee, I began seeing patterns in what did and did not resonate with the committee members

The Good

1)    Having a difficult concept.

This may sound counter-intuitive to some, but having a hard idea means that there are relatively few who are going to try to do the same thing, which equals less competition. You can think of “having a difficult concept” as feast or famine. If you can’t execute on the concept, you’re done and out of business; but if you stick it, you could corner a market.

2)    Scrappiness.

Time and time again I heard, “I like their team, they’re scrappy.” Scrappiness is that ‘do whatever it takes’ mentality some entrepreneurs possess, when they would rather beg for forgiveness than ask for permission. Teams that are scrappy shatter expectations; Techstars likes those people, I like those people, be one of those people.

3)    Coachability.

As any investor will tell you, its all about team, team and team. Companies change, they pivot into different markets and alter their product offerings, but amongst all of that change one thing remains constant, the team. You could be sitting on a goldmine of a concept, but unless you have the team to execute on that concept… forget about it. For Techstars, coachability plays a huge role in gauging whether or not a founding team is up for the task of launching a company. Remember, nobody wants to work with people who refuse to listen; it’s ultimately the difference between confidence and cockiness.

The Bad

1)   Not crunching your market numbers.

Know your market numbers! That means figuring out your total addressable market, or the number of customers who could feasibly use your product or service. Ultimately you use those numbers to extrapolate how much revenue that means for your company if you capture X% of that addressable market. Not knowing those market numbers and what that means for your revenue is bad in and of itself, but it’s also indicative of something much worse, incompetence. Avoid looking incompetent at all costs.

2)   Lack of a large market or need.

Sticking with market issues, lacking a large market or need is probably one of the single most prevalent issues with startup concepts. For entrepreneurs, their startup concepts generally grow out of a problem that they have personally experienced. That’s all well and good, but Techstars is in the business of accelerating high-growth startups with huge market potential, not lifting small lifestyle businesses off the ground to chug along at $500K per year. So before walking into screening committee, ask yourself these two questions: A) do I have a large addressable market? And B) is there a compelling need in that market for my product?

3)   Failing to communicate your concept clearly.

If at the end of your pitch, “so… what do you do?” is the first question from the committee, you messed up. Before even starting work on your full pitch deck, it is vitally important to nail down your value proposition. A quality value proposition is a one-sentence description of what you do. For my company QuintEssentials, our value prop is, “we are an online, subscription service that delivers personal care items to college students.” Quick, dirty, and most importantly, clear! If you can’t even explain what your own company does, trust me, no one can.

Sitting in on Techstars Boulder screening committee was one of the single most informative experiences I’ve ever had. I feel honored to have played a role, albeit small, in that process. There is no single word of advice that can ensure the success of a startup. That said, being a fly on the wall and listening to highly respected VCs and Techstars staff weigh in on 45 different startup has informed me of hot-button do’s and don’ts to consider on the path to startup glory. 

Talk, Damn You: 3 Keys to Getting a Foot in the Door

Dear young recent grad/career seeker,

Guess what, no one knows you exist. Isn’t hyperbole great? But in all seriousness, you probably aren’t as well known as you think you are, especially not in professional circles.
Okay, so you have a solid group of friends and few of your professors know your name, but at the end of the day those people aren’t likely to employ you after graduation.
My advice? Talk, damn you; talk!

Warmest regards,
Reality

I would have a handful of students walk into my office at the Deming Center each week asking about jobs with local companies – how to find them, where to apply, etcetera – and having no clue how to approach the situation. My answer to their burning questions was always the same, “get out into the community.” As you can imagine, there was a lot of, “is that it?” and “is that all you got for me?”

“Yes, that is all I ‘got’ for you!”

In reality I could have told them to check LinkedIn for job posts or visit sites like Monster.com, but no other suggestions would have been as helpful in the long-term as “get out in the community.”

Boulder, and other cities like it, has an incredible startup ecosystem with a wide variety of opportunities at companies of all sizes. So in the midst of this ongoing startup boom there are plenty of jobs to be had, and in my experience getting out there and immersing yourself in the community is the best way to get a foot in the door with a company, and ultimately a job.

Here are the three bare-bones steps I have discovered work best for doing just that:

1)   Go to Events
I was always telling business students at the Deming Center that if they wanted to, they could attend a local business event for breakfast, lunch and dinner every day of the week. 1 Million Cups for some morning networking, iLaunch in the afternoon for some quality programming and House of Genius in the evening to polish up on your pitch feedback. That is an entirely plausible day here in Boulder, and I can bet days like those are doable in most major cities across the country.

There is no substitution for good ‘ole fashioned showing face. The more entrepreneurship and business events you go to, the better. I have personally gotten more business cards from simply showing up to local events and asking this one question: “so what brings you here.” The end goal isn’t to pitch yourself, it’s simply to mingle and get a follow-up conversation with someone.

2)   Find Common Ground
So you are attending an event and introduced yourself to someone… now what? If you take anything away from this post, it should be this: People love to talk about themselves and their personal interests. So use that! Get others to talk about what interests them. When they mention something that you have a similar interest or curiosity in, engage them about it. In sharing similar interests with someone, you establish common ground that makes you stick out in that person’s mind.

In the past year I can recall only a few instances when I genuinely had nothing in common with the person I was talking to. The common ground can be as simple as a favorite restaurant you both enjoy. The important part is, in creating that common ground you establish a personal rapport with those you encounter.

3)   Be Genuine  
Unfortunately, the word “networking” comes with a negative connotation. Networking is often seen as nothing more than disingenuous socializing; the kind of thing that sleazy people do to get ahead in their own careers. This negative connotation makes it all the more important to be genuine.

Most successful entrepreneurs can sniff out BS from a mile away, and as soon as they feel that you’re speaking with them purely for the sake of personal gain, you’ll be shut down so fast it will make your head spin. Engaging in an insincere conversation is worse than not engaging in conversation at all.

The first step to getting a job in the entrepreneurship space is to get a foot in the door. All too often, college students and recent grads overthink how to do that. Its honestly as simple as going to events, establishing common ground with those you meet and being as genuine as possible throughout the entire process.

Listen to others, ask engaging questions, be passionate about your pursuits, and eventually an opportunity will come your way. 

Beautiful Ambiguity

I will preface this post by saying I am by no means a success story… yet. I say “yet,” because I strive to be someone who is known for getting shit done (credit to Spark Boulder). My goal is to one day be a man who has built his career on the foundation of a “give first” mentality (credit to Techstars), and who’s giving actually makes a significant difference in the lives of others.

That ambiguous goal is at the core of everything I do, and it’s led me from starting my own company a year ago to now working at the best startup accelerator in the world.

Don’t get me wrong; I believe a certain level of focus in goal setting is necessary to reaching one’s version of success. That being said I also believe that everyone should have a high-level, ambiguous goal they chip away at each and every day.

I have by no means “made it.” Far from it in fact, but in allowing my actions to be guided by my ambiguous goal of giving first and getting shit done, I hope to help others reach their success and in turn reach my own.

Working towards my high-level goal has put me in an amazing position to go after my aspirations and become what I want to be. I view Techstars as the heart of entrepreneurship in Boulder. Simply to be in Suite 202 sends endorphins coursing through my veins.

I have a golden opportunity to make something great out of my current position, and a lot of people to thank for putting me here; but at the end of the day my actions are my own, and everything I do is informed by my beautifully ambiguous goal… give first and get shit done.

What’s yours?

Don't be That Guy

“It’s the thought that counts,” say people, always.

You would think there has to be a point where that simply isn’t true.

I went on the hunt for coffee at Techstars recently and found a freshly made pot, compliments of Cali Harris. There was maybe a half-cup left in the pot once my mug was filled with that life-giving bean juice. As I passed Cali’s desk I mentioned there was only a little bit of coffee left, but the look I received from both her and others made me stop in my tracks and re-evaluate my decision to leave a few drops.

“Should I just kill the pot?” I asked with hesitation.

“Yes, don’t be that guy,” was the resounding response.

The whole thing got me thinking, and eventually I came to a conclusion. An action is comprised of two things: a thought and the execution of it. At a certain point, “It’s the thought that counts” doesn’t make up for poor execution.

Like many phrases, – “hey, I tried,” and “well I was drunk,” just to name a few – “it’s the thought that counts” is often used as a crutch that allows people to remove themselves from being held accountable for their actions.

“Well yeah, I may have gotten you a pair of mismatched earrings and a half-finished coloring book from Goodwill for our anniversary, sweetheart, but it’s the thought that counts… right?” Wrong!

‘That guy’ uses phrases like, “it’s the thought that counts” religiously. ‘That guy’ half-asses selflessness to cover up selfish acts. ‘That guy’ thwarts responsibility. Nobody likes ‘that guy.’

Strive for better, because honestly, everyone would rather you just drink the rest of the coffee than to be ‘that guy.’

Big Fish and a Nod to Failure

I love the movie Big Fish. I’ve watched it at many different points in my life and received a new underlying message each time. I recently sat down and enjoyed it again and came to an interesting conclusion: we often find meaning in unlikely places. Let me explain.

The world around us is comprised of dichotomies: good and evil, right and wrong, success and failure. In general, society teaches us that one is fundamentally better than the other. Good is better than evil, and success is greater than failure, period.

Screw that. I would argue we often find the most meaning in our pursuits when we embrace the ‘socially prescribed’ lesser of the two. So in launching a company, I urge you to come embrace the dark side.

At its very core, Big Fish plays with the simple dichotomy between fact and fiction. The patriarch in the movie is a great storyteller because he embraces the fictional and the embellished.  Much in the same way, we as entrepreneurs must embrace failure in order to become successes. There’s one problem, fear.

Fear is crippling. Our fear of failure snuffs out our courage to innovate and to take risks, but it doesn’t have to. The only reason we are afraid to fail is because of this pervasive belief that failure is unacceptable when success is an option. Be gone with that droll I say! It’s okay to fail. In fact, I would encourage it.

Perhaps I’m leaning towards the extreme, but it illustrates a point. Entrepreneurs need to liberate themselves from that fear in order to succeed, and the only way to do that is by demystifying failure. Share your stories of failure. I love hearing of my mentors’ shortcomings, and I love sharing my own. In sharing those stories we create an environment where its okay to fail, and in doing so, also make it okay to take risks and dare to succeed.

After watching Big Fish, the moviegoer is supposed to come to the conclusion that sometimes fiction is a powerful supporter of fact. After reading this I hope you come to a similar conclusion, that sometimes failure is a powerful supporter of success.

I would rather build my success on a foundation of failures than live atop the precarious tower of triumph, but hey, maybe I’m one of the crazy ones.  

The Story of a Closet Optimist

“Everything is going to be fine,” I explain.  

“What the hell makes you think that?” She retorts, frustrated at my seemingly lackadaisical response to the issue at hand.

“I don’t know, because why wouldn’t it be fine?”

I realized recently that I am inordinately well equipped to deal with big, cumbersome issues. After coming to that self-actualization, my natural curiosity was to figure out why. A couple of days and perhaps a few beers later, it dawned on me; I have a surprisingly positive worldview.

I say “surprisingly” because for years I was convinced I was a pessimist. I was critical of mistakes my peers made, I considered the potential consequences of my actions and I had lofty but realistic goals; all things that were perceived by my classmates and friends as a negative worldview, and at times, a buzz-kill. Then life happened.

Kids who aspired to be doctors, and lawyers (insert stereotypical ideal of success here) went off to college, made mistakes, missed opportunities, lowered the bar and took another shot at it from the shameful comfort of their parents’ basement, fueled by a newfound bitterness towards life. So how did I manage to avoid these major setbacks? These unfortunate pitfalls that belittle even the seemingly strong?

I didn’t... In fact, I failed to avoid damn near every one of them.  

There was a fundamental difference between how my basement-dwelling peers and I viewed the world that helped me move past the same adversity that belittled them. I knew that everything was going to be fine, and I still do.

Some may guffaw, but I truly believe that if I work hard, remain open to new opportunities and keep a humble attitude, everything will be just fine. Yes I may stumble, and at times even fall flat on my face (I wish this was only figurative), but when you’re certain that everything will be fine, why not get back up?

“The world isn’t burning, and the sky isn’t falling. Trust me, we’ll be just fine.”