Friday, March 28, 2014

PACKBACK: From Chi to Sharks, It's the Weird Ones that Matter

From Chi to Sharks, It's the Weird Ones that Matter

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My good friend Kasey Gandham and I showed up on TV screens nationwide this past Friday. By the time the clock struck 9:00CT, over 8 million people had watched us shake hands on a quarter million dollar investment with Mark Cuban. 250+ of those were watching (and cheering) with us inside a place called 1871, the same place I had been sneaking into a year ago just trying to be in the same environment as real entrepreneurs. Family, friends, investors, supporters, and, naturally, a ton of college students joined our team in watching ABC's "Shark Tank". A minute afterwards, Kasey and I took the stage for a conversation with one of our newest mentors, Rishi Shah, to tell some stories about the past two years' adventure. 17 hours later I'm standing in the Chicago Bulls' locker room talking to Derrick Rose, Carlos Boozer, and a host of trainers and organization members who didn't know my name last week (I've been a Bulls "ball boy" for seven years). All conversations revolved around this crazy, yet captivating idea that a few friends and I had in college, which we called Packback. 
So, now that I have your attention (particularly high school and college students). Here's the one thing that I've learned above all: don't ever, ever, be normal. In the end, it's the weird ones that really matter.
     When I first went to college, I wanted to be an entrepreneur. I knew it. But there were so many people that were so much smarter than me who knew that it wasn't a smart path to take, and thus convinced me otherwise. Eventually, I read the Warren Buffett biography, "Snowball", and thought that his job seemed like a fun game. I decided that I would become a financial analyst. In doing so, I read and took notes on all of Ben Graham's riveting "Intelligent Investor" and 'Security Analysis" books, took a class in which a group of students manage a $450 million portfolio for the university, and did everything else I could to learn about the stock market before finally understanding one concrete truth: I was going to be bored as hell in this career. Come senior year (Fall '11), Kasey and I started hanging out with a couple of friends and discussing off-the-wall ideas over a case of beer...
The purpose of this post is to paint a brief picture of the type of people that surround us at Packback, and why the public perception of what "professionally accomplished" looks like is way off. At the end, I'll tell you about how I like to write rap songs, and precisely why it's crucial to my entrepreneurial career that I tell you that. But first, I'm going to tell a bit about four particular individuals who have had an influence on me in the past year. 
Garbage Man Millionaire 
We spent the past summer scrapping our way to Packback's seed round of funding, meeting by meeting with potential angel investors. Along the way, the journey led me to a lake about 40 minutes west of Milwaukee, to meet with an old man by the name of Joe Tate. As a youth, Joe was a sure shot high school football star, and went on to play at Indiana University. Upon graduating college, he didn't know what he wanted to do, and the average job opportunities staring at him simply weren't appealing. He had an uncle with a truck, and a friend with a garbage pickup contract. It was a pretty "crappy" job to say the least, but nevertheless he decided to spend his days hanging off the back of a garbage truck and man-handling trash (the trick, Joe explained, was to extract the garbage even when the negligent residents had chained their pissed off Rottweiler to the can). At night, he learned how business works by walking into sole-proprietor bars and making deals with bartenders to take their trash. His friends thought it was weird he didn't have a regular job. Fast forward twenty or so years and that business went public before selling outright for a cool $1 billion. Joe held onto about 8%. Do the math. The lake we were eating lunch on seemed to be some kind of fairy tale village surrounded by monstrous mansions. He looked at me, after telling his incredibly gritty story, and said "Mike, who the hell wants to live a normal life?" 
Trader Turned Angel (reader discretion advised) 
     With just our energy, and a (very) tentative verbal agreement with one publisher, we were in a bit of a "chicken and egg" dilemma for Packback in the winter of 2013. We didn't have the technology we needed to host digital textbooks, nor did we have any money to build the technology. We were close to a solution with tech-dev accelerator, Dashfire, but the at-cost development expenses were going to run about $10,000. We needed a little bit of cash, or this crazy adventure was going to come to a crashing halt. 
So, in natural form, we cold-called a guy we had met a few months prior, when he was judging the ISU business plan competition and we were invited to give a Packback update. He had long black hair, tied into a pony tail, with grey streaks running up the sides. He spoke with a peculiar focus, staring you straight in the eye with a fiery intensity while discharging a furry of seemingly off-the-wall thoughts. This guy wasn't weird, he was f***ing weird. His name was Alan Matthew. He had made his fortune as a long-time commodities trader, thriving in the pit of the Chicago Board of Trade. Having retired from the pit, his new hobby is that of establishing himself as one of the most active, and daring, angel investors in the Chicago tech startup company. Oh and when he isn't doing business? He skips along between 80+ countries, and spends a particular amount of time on the Amazon River as an accepted member of a tribe of Shaman healers. You know, just the typical stuff they teach you in school. 
After a few more phone calls/emails, Kasey and I ended up sitting in Alan's high-rise Chicago apartment (Kasey was barefoot) on a cold Saturday afternoon in January. After an hour-long heated discussion, Alan slapped down a check for $15,000 on his coffee table and told us: "There. Now go figure this fucking thing out". We went back to work. 
68 year-old Sleepless Rebel 
    As our network grew, we finally scored a meeting with a man considered to be a thing of legend in Chicago. After founding a dozen highly successful startup companies, the 68-year-old Howard Tullman was still sleeping less than a handful of hours a night and working relentlessly on his latest project. He's a trusted and depended-upon professional colleague of nearly every Chicago business tycoon, the mayor, and even former President Clinton, just to name a few. Nevertheless, Howard is as weird as it gets.

In navigating towards our first meeting with him, we had to first walk through a maze of (his personal collection of) eccentric art, before sitting in a crammed office, with walls lined with colorful skate board decks amongst other decorations and a massive TV screen connected to his hyperactive computer. Howard was still in his role as CEO/founder of Tribeca Flashpoint Academy. What was amazing to me, was that with all of the professional and prestigious contacts one could ask for, he was spending his time rocking a T-shirt and a silver mullet, surrounded by students in a media arts academy. Howard himself went to Northwestern and studied law, yet TFA is a school that fosters and encourages the inner creativity of often rebellious students that in many cases were feeling (or truly being) rejected by the standard colleges, never mind the "elite" ones. Howard champions the crazies, the misfits, and the rebels.
It was was one of the most exciting days of the summer when, on July 15th 2013, he wrote a check out to Packback. 
Eccentric Billionaire 
And of course, the footage of how we roped in our latest investor was projected to the masses on Friday night. Not much needs to be said about Mark Cuban. There's nothing orthodox about him at all. In preparing for our "Shark Tank" pitch, I especially enjoyed one line in particular from his book. It was an explanation to why he's participated in such weird activities as "Dancing with the Stars", and taking an obvious risk of embarrassment. Mark said, "When I'm 90, will I smile when I think back, or will I frown and regret not having done it?  ...Success is about making your life a special version of unique that fits who you are. Not what other people want you to be."
...It was with those influences in mind that I sat in an intimate dinner last Thursday, the night before "Shark Tank" aired. The special guest was a seasoned venture capitalist, and current partner at Pritzker VC, by the name of Matt McCall. Matt generously spent the evening sharing tidbits of wisdom in an open discussion with young entrepreneurs. The nugget that struck me the most was a statement he made, and repeatedly emphasized, about "showing vulnerability". Matt's take was that until making yourself totally vulnerable you can never reach your full potential, and can't possibly build truly genuine relationships. Hmm, well that's weird, I thought, and yet began pondering what I could possibly do to make myself entirely vulnerable. The answer was quite clear. 
I developed a habit in high school, wherein I would dump all of my thoughts into a red notebook and create a page-long rap. Not poetry, rap. You know, that three-letter word which sends shivers up your parents' spines. It was a phenomenal exercise, which forced me to think through my present situation a hundred times with each line to find a set of words that fit the evolving puzzle of rhyming statements. When I was done, I always felt better, and would proceed to lock the red notebook away until the next session. Over time, I started getting the hang of it, expanding to multi-syllable rhyme matches, intra-rhymes, and forming stories with it all. At the tail end of college, I decided to try my hand and put a few internal projects into production. I spent about 30 or so hours in a shabby studio, hidden underneath a rotting bridge in Normal, IL, working with a little-known hip-hop producer on this clandestine operation. After all of that, I never revealed the project. It would have opened up an extreme level of vulnerability, and I wasn't ready for that. Plus, I wanted to be a businessman, and vulnerability kills professionalism. Right? 
There's always a limitation. There's always a social constriction or some bullshit reason not to do something. When you're 90 years old laying on your death bed it's all going to seem so minuscule -I think I agree with Mark on that. So count me in with the weirdos. I wouldn't have it any other way. In some apparently precursor tribute to this very revelation, I wrote the following in the winter of 2012. I had just finished reading Walter Isaacson's Steve Jobs biography. I turned the last page, put down the book, and picked up my red notebook…

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