The Myth of the Underdog

So I’m going to talk about Underdogs in the digital industry.

Lets imagine there is a team that is diligent, hardworking, and a bit intense. This team drills to be disciplined to push through their failures and rise to successes. And failures abound for all aspiring teams. The flush of initial success can embroil a team into petty quarrels as nascent egos flare. Or stability in growth or lifestyle can create complacency, and allow teams to stagnate.

Imagine this team sees these pitfalls, and through sheer grit and discipline, pushes through to the other side. The side of glorious victory.

Imagine this team is the villain in the story.

The “underdog” are any one of those other fools who didn’t have the wisdom or the discipline to hold it together and push through, but by sheer luck or last-minute drama, they catch a lucky-break and beat out the “villain” who did. This is my take on just about every underdog story I see. I don’t care if it’s Bad News Bears or Hoosiers: whenever we’re presented with the “villain” of the plot, we’re presented with a well-oiled, confident team that is ready to compete. End of discussion.

I’m going to tell you something, something that no one really likes to say aloud:  in real life we’d all prefer the villain to “win.” Let me put it this way: do you want an “underdog” to be your heart surgeon performing that risky operation, or would you rather have the guy that has a winning track record? C’mon, when it’s your life on the line you want the guy with the track record. You don’t want an underdog making your car. You don’t want them building your databases, or launching your digital product. You want a tried and true winner. That’s the bottom-line. The only, only, only time you take the risk on the underdog is if there’s a sense of trust and confidence there that is lacking in the other competition. Or you’re strapped for cash.

My Top #5 Rules for Managers

Here’s the short list

#1 – Your health is your responsibility.

You can’t manage if you’re constantly sick, unhealthy, or rundown. Period.  It’s very easy to eat poorly, work long hours, sleep less, and develop nasty habits. Personally, I’ve gained 35 pounds since I became a manager and I’m taking actions to deal with it. I am keenly aware that if I’m rundown, I stop being an effective leader.

#2 – Get Funny.

As a manager, it is your job to have a relationship with the people you’re managing. A few gifted devils can walk into a room and instantly connect with half the world. The rest of us are stuck as wallflowers. As a manager, you can’t lead without having a good relationship with your team. The problem is that you and your team come from very diverse backgrounds, and most likely have nothing in common other than you all decided it’d be great to work in the same proximity to each other daily.

But don’t worry, I’ve found a hidden buddhist koan to help people connect:

“Jokes – especially bad, corny jokes – are the common denominator to all people and cultures.”

Once you become a manager, go out to your local bookstore, dig through the $.99 bin, and buy the corniest joke book you can find. The cornier, the better. How do you know if it’s a good joke book? Here’s a hint – if your 5-year-old nephew likes the jokes from that book, it’s a winner. Memorize as many of those jokes as you can, then slather your team with them like mustard on a hotdog. I guarantee this is the bedrock to forming a bond, and from there forming a working relationship.

(Oddly enough, pickles are also a common denominator to all people and cultures.)

#3 – Your boss’s solution is horrible.

If am I your boss, and you come to me with a problem, I promise you that my solution will be horrible, unfair, probably vague or complicated, but most importantly, ineffective to solving the problem. Odds are you are closer to the problem, so you are closer to the solution.   Now, that’s not to say that your boss is useless – on the contrary! Your boss is an excellent sounding board for shaping ideas, he/she is a sympathetic ear, and he/she can walk you through the ramifications on strategies that you might not see. Your boss is your advisor and trusted confidant, but you are the manager and your job is to at least present some solutions to problems as they arise (hence, why you’re a manager!) If you’re looking for your boss to magically and neatly solve your problems, you’re setting yourself up for failure and disappointment.

#4 – The job is hard enough.

“The manager’s function is not to make people work, but make it possible for people to work.” – quote from Peopleware. ‘ The job is hard enough, you don’t need to drive your employees mad by overloading them on status reports and random acts of micromanagement.  ’Nuff said.

#5 – The work is the work.

If you are at work, you are working. You are the first one into the office, last one to leave, and if your team is in another physical location your skype/hangout/cell/email/pager/carrier pigeon is open to receiving communications. “Offsite meetings” does not mean “I get a half-day!” “Traveling long-distance” does not mean “vacation.” “Drinks with clients” does not mean “we’re getting bent on the corporate card.” “Work-From-Home “does not mean “I’m doing chores and checking my email every hour or so.”

Bonus rule – If it’s unclear who’s at fault, then it’s definitely your fault. You can’t have responsibility without accountability!

These rules work. I know, because I’ve broken each rule during in my career and I’ve suffered the consequences. Feel free to add on to your own personal rules as you go, but this should get you started.

PS – if you’re not a manager, do #2 anyway. The world needs more corny jokes spoken out loud. Pickles are a bonus.

PPS  - This guy came up with 101 rules! What…the…heck?!


I’m confused about mentors

So it seems that every tech entrepreneur has a mentor, is looking for a mentor, is a mentor, or all the above. It’s freshman year dating season all over again.

I might be crazy, but I’m not doing any of those things. I have good friends, trusted colleagues, confidants, but there is no sage person in the background offering up advice when the tough choices come rolling in.

Frankly, I wouldn’t know where to start looking for a mentor if I wanted to, and I wouldn’t know who to mentor (or what to mentor on) if asked.

But maybe it’s not really necessary. The business of DOM & TOM is pretty straightforward – you offer hours of services in exchange for money. In many respects, it is the same business as an accounting firm, or a law firm, or any other service-based business. It’s not exactly kungfu…

There’s desire to be mentored and to mentor others in the tech culture.  I don’t know where else to attribute it to other than Silicon Valley, which sets the standard for all other tech cultures in the US. Part of that mystique is the mentor-student relationship that seemed to promulgate heavily in the late 90s and early 2000s.

In any case, I’ll reserve judgement on the topic of mentorship for another day. It’s been 5 years toil on this business, and I haven’t had the support of that sage person in the back room for guidance, but that doesn’t mean he/she isn’t worthwhile.

Trust is Earned

Trust is not a gift. It is earned in deeds done, and wars won. – Anonymous

Trust between two professionals is a hard-won accomplishment. There isn’t a sin I haven’t committed when it comes to trust. When the company grew, I found myself doing annoying and downright rude habits with my colleagues. I micro-managed, I second-guess people’s motives , I undermine work being done by checking in randomly, then asking questions that I knew couldn’t be answered on the spot.  Sometimes I realized what I was doing, and stopped. But I’m sure I didn’t recognize my bad habits all the times (hence, why they’re bad habits) and that gives me cause for pause.

As my brother Dom says, “perception is reality.” I find that as my stress increases, my trust that “stuff getting down”-ness in the company decreases. It can turn into a negative spiral that leads to hurt feelings and lower morale. The best we can do is fight the insecurities and remember the good character and intentions of those upon who you rely.  Hemingway said it well – “‘The best way to find out if you can trust somebody is to trust them.”

That said, once we take the first step in trusting, it’s nice to verify. Thanks Ronald…




Professional development is embedded in our culture

We doubled in size last year. So 2x the people; 2x the costs; 2x the gross revenue; 2x the complexity of problems.

In order to maintain the growth, we recognize that  professional development is now part of our culture.

One thing we did poorly last year was not structure professional development for people who want to move up the company. People who stayed with us for a few years were starting to ask  ”How do I advance here?” or “What’s the next step for me to move up the ever-lengthening corporate ladder ?” We were so busy hiring and *GSD’ing that we neglected that people want a career path. Such an obvious mistake, looking back.

  • At the end of last year/early this year we gathered goals from all the employees and are creating career paths for our people.
  • We’re creating Hackathons for our teams to collaborate with each other, especially people they normally wouldn’t work with.
  • We’re creating a D&T library and forming groups to read through management books, leadership books, and other company-fostering books.

It’s hopefully the bedrock of the next phase in D&T culture – one where we all now collaborate to become a better, more-professional, organization. It’s a step away from the old days, where we’d go out as a team to the local pub after a hard day’s work. Now we’re trying to improve each other materially.

If anyone has ideas on new initiatives we should include @ D&T feel free to contact me via the comments, or in my email

*GSD’ing means “getting stuff done”

one smug nerd at a time....

one smug nerd at a time….

New York stunts your life

I’m a child compared to my friends.

I am 31 years old, never owned a car and never owned a home, and don’t have children. I live in the cheapest apartment I’ve ever lived in my life, with my wife and cat. Logistically-speaking, my life is exactly the same as it was when I was 21 years old.  My wife is in the same boat  - her job is the same type she’s had since her 20s, and her friends are the same ones since she first moved to NYC (with a few exceptions).

My friends, on the other hand, have families, own cars and homes, and are experiencing the headaches and joys of all those things. I get that “owning stuff” does not make you a better person, or that having more kids around doesn’t provide deeper wisdom – people who are jerks still are jerks, just with more kids. That said, I think there’s a fundamental change when you alter your environment.

But frankly, it’s very hard to alter one’s environment in New York City. Rents are high, and get higher every year. Even if your job allowed you to get more money, what exactly does that get you? A slightly bigger apartment maybe, and the ability to eat out a bit more.

Or visit your other friends who seem to be progressing rather quickly into their lives while you’re still relating to college students with their first jobs.


5 Things I’m Thankful For in 2013

There’s plenty to be grateful, but I’ll just hit the top 10

#5 – Married to someone who works out.

I seriously would be an horrible shape were it not for Julie. My wife works out 4-5x a week, and is an inspiration to keep in good health and shape. If it weren’t for her, I’d be more “Bear” than “Otter” (evidently lingo in the metro-sexual communities…)

#4 – Traveling more than ever

It’s a personal goal to see new place every year. This year: Turkey! What a great country!

#3 – Family and friends near and far.

I swear, I’ve seen more family, both in NYC, Chicago and afar, this year than ever before.

#2 – Continuing to write, starting to podcast

Fun things I’ve written this year: ghost stories, blog posts, twitter feeds, listener feedback. It’s a start. My goal is to write/publish a series of short stories. I’ve never done sound recording, and I’m eager to experiment with it. Episodes to come out in 2014!!!

#5 – Health

Rocky year, all in all, but I came through better than ever. At age 31 I bench more than before, lift more than ever, and have a positive POV to dramatically improve my cardio next year. It’s going to be…awesome.

We got some work to do…

Heard a great quote today.

Bill Withers  “I’m doing the best I can, to improve my lineage and my species. So I got some responsibilities…”

That’s a 75 year old blue legend, saying he still owes the world and himself more, after a lifetime of greatness. If you don’t know Bill Withers, please feel free to search the internet. Guaranteed you’ve heard his music in one form or another.

I hear from people in my industry that the Millennials are the worst generation we’re facing. They’re selfish. They’re rent-seeking. They have no loyalty. They want to promote their brand and don’t give a damn about the big-picture.

Personally, I don’t think there’s any difference between this generation or any other generation. The circumstances have shaped the outlook, and this generation is responding to those circumstances. If you’re living in an environment where we make corporations into “citizens”, there’s a global meltdown right when you join the workforce, internships have been turned into indentured servitude, you can’t help but wonder where the next kick is coming from.

Look, there used to be a social contract between COMPANY and EMPLOYEE. The contract was simple: Employee “hey, I will work at x Company, and be loyal, so long as you treat me fairly.” Company X “sure! We value long-term growth and won’t axe you in a short-term downturn or because we need to increase investors’ value.”

Sounds fair to me.

Today – everyone is mercenary. You can sign whatever contract you want, but the end of the day is that it’s all the power in the owner’s hands.

Jack Welsh one time had high-paid engineers at GE paint the buildings when there was no work to do, just to keep the team together. Imagine that – VPs and senior talent, with nothing to do, so he made them paint. He had vision to see that losing top-talent would be good short-term, but devastating long-term.

No such vision today, eh comrade?

I can’t tell Millennials that they’re wrong to being mercenary, or looking at the short-term. We – the company and its owners – have trained them to not count on anything. But I don’t want to have that in my piece of the world. I want to have my own, private revolution/revelation. I want to revolt against that mindset because I believe, I truly believe, that we all want that original contract, the one that used to be in place back in the day, that we’re all in this together and that we all deserve a promise to that end.

Like Bill Withers, we got a lot of work to do, and will be doing it into our old age.

The Heart and Soul of a Company

I recently came back from an all too infrequent trip to the West Coast.

Folks, if you’re in America, and you’re in Tech, and you live anywhere other than the West Coast, go to the West Coast more often. I don’t buy into a lot of the hype of Silicon Valley/Redwood/LA, but I do think there’s a lot of interesting things that are happening and it’s a different style of living.

Back to my point.

Visited a good friend and talked about his game company. They’re making tremendous progress, even if they can’t see it, but it’s frustrating because they’re in the midst of year #2 doldrums. The doldrums of year #2 for start-ups are clear – the weaker partners/employees lose heart and fade out, drama over “making it” vs “staying true to vision” crop up, and all the external anxiety with spouses and girlfriends come to a head.

I came into the middle of that unfolding in front of me, while visiting my friend. My friend is one of the founders and he’s in the trenches with all of this. It was a typhoon of optimism and anxiety. Unless you’ve been there, don’t pretend to get it. It’s like tasting spam for the first time.

We talked. I gave him some advice. He like the advice and is taking his spin on it. All is good.

But he said something that was a little odd. It was “hey, I wish you were CEO for us.”

I initially I gushed and said “sure! love to! we’d have a blast…” I’ve always wanted to work with my friends, particularly in a game company.

But the truth is that I’d be horrible for the job. The CEO is the heart and soul of the company. He/She embodies the mission statement of the business, and is intrinsic to the core values therein. I’m good at my company. If I was the CEO of anything else, that company culture would confirm to my vision, values, and goals. What a shift that would be! (PS, I’m not the CEO of D&T – that’s my bro Dom!)

The point that I am making is that when we seek out leaders, whether they are C-level or just managers, we need to be cogent to the fact that these people embody values and goals that need to speak to the overall vision of the company. Doing anything else creates friction, fractions, and distractions to the overall vision.


Vodka Drunkenski changed his beverage of choice, and after that move he is now called Soda Popinski. Good career advice works!


Know when you’re ready to manage…


I find this is a deep problem in the start-up community.  But before we talk about management of employees, let’s talk about the operations of a business. It’s my belief that that #1 operational goal of a company is to create stability and reliability in its processes and business model. Bills are paid on-time, payroll run on-time, clients pay on-time, work done on-time, etc. Keep the process running reliably, and your business will prosper.

People, conversely, are your #1 variables. They’re always throwing wrenches into the gears of this steady engine – getting sick, taking time off, being way better than you calculated. Their productivity is always growing and ebbing so that they never quite fit the models created.

So when you’re looking to manage people you’re really saying “I’m attempting to take on the hardest thing to do in the business – harder than the work itself.” Once you understand that, and accept it, you’re in the right mindset to manage.

There’s a lot to go into being a good manager, and managing personality types, but I won’t get into that here. I’m going to describe the core points that I think a manager needs.

1.) Have a plan for your people and yourself

You’re managing a team – it’s your job to know what you want from that team, communicate it, and then constantly challenge the team. Too few managers do this. People hire when they feel overwhelmed with work, and not until it’s too late that they realize that hiring actually CAUSES more work upfront, not less. Training, communicating, creating plans and progress milestones – all work! If you’re going to get the most out of people, have a plan before you hire and execute on that plan. And then always have a back-up plan.

2.) Periodical check-ins.

Odds are, you’ve hired smart people. But they’re not automatons – you need to check in personally and frequently to make sure things are on track. Most experts recommend 1x a week initially. I’m ambivalent on that – I think the situation dictates the needs. If you don’t like checking in with other people’s work, I don’t blame you.

3.) Guts

It’s easy to communicate bad news to yourself. It’s hard to convey that to someone else and hold them accountable. More often than not, green Managers will avoid conflict or correct the work themselves. I had both done to me personally by several managers in my previously life. Here’s a secret – most employees know when they’re messing up. They’re just lost on how to ask for help. Well, at least that’s how it was for me (and probably for you, right?)

4.) It’s not personal

When you go from employee to manager, you have to change your relationship with your team. It is difficult and I have a hard time doing it myself. I don’t like the idea of hierarchy – there’s a lot of efficiencies found in a flat organization – but every business has a boss, and every team has a manager. If you’re not willing to alter your work relationships (which can be deep and wonderful and the best ones in your life) in order to manage, please do not manage. You will ultimately hurt everyone around you.

If you feel like you can plan, communicate, and have the emotional fortitude on meting out bad news (and praise) along with keeping a professional barrier, you’re in the right mindset to manage. It’s a difficult transition and one that does not appeal to most people. Most people don’t want the hassle, and there’s unfortunately a lot of people who choose to manage because that’s the only way to get a raise/bonus or move up the corporate ladder. Yikes. For the few who want to provide leadership and guidance for a living, this is my bare-bones assessment of what is required.

Good Luck!