Red, Jackson, Gen Y & Loyalty

Posted to my email list yesterday.

I only post one out of every five email newsletters here, and I normally take them down after a while. If you want to get my newsletter and you can figure out to use LISTSRV software from 1994 visit By signing up for the newsletter you are agreeing to the Declaration of Calacanis.

———- Forwarded message ———-
From: Jason Calacanis
Date: Mon, Apr 26, 2010 at 5:21 PM
Subject: Red, Jackson, Gen Y & Loyalty

Note: We setup a new, hopefully more reliable, server for Jason’s
mailing list. If you have had any issue signing up or being removed
(we’ve heard a handful of each) hit reply or send request to

Note2: Going to try to get these out more regularly now that the baby
is sleeping through the night some nights. 🙂


Tuesday night, around 10:30PM.

A dingy visitors locker room in the basement of the Staples Center
dressed with pipe and drape, hightop tables and a sad selection of
beverages. Kobe Bryant’s stunning wife sitting on a five-dollar
folding chair in the hallway wearing a wedding ring that is,
literally, covering half of her hand.

Twenty minutes after the Gen X Lakers held on for a win against the
energetic Gen-Y Oklahoma Thunder, the large-framed Jedi master–a six
foot Yoda–slowly shuffles into the room. Five or so VIPs who’ve
waited for the post-game press conference to end quickly turn silent
and direct their attention to the master.

A calming grin, “Hi, I’m Phil Jackson.”

With reverence, “Jason Calacanis–a real pleasure to meet you. Nice win.”

“Thanks. Those kids can block shots huh?”

“Oh yeah. One question, what was Bill Bradley like when you played
together on the Knicks?”

Fifteen minutes later, the question is answered at a level of detail
no one expected, and few probably comprehended. The master operates on
many levels–concurrently and unspoken.

The Knicks won their only two titles in 1970 and 1973, and when they
did, it was with a team of solid players, including Dave DeBusschere,
Willis Reed, Walt Frazier, Dick Barnett, Phil Jackson and Bill
Bradley. Bill Bradley famously went on to become a senator, but I’ve
had the privilege of eating dinner or lunch with him once or twice a
year for the past four years. (He works with Allen & Company, which
has an investment in my company).

Bill and Phil both played for the legendary Red Holzman, the coach of
those championship teams and a mentor to Jackson.  Red was from
Brookly,n and he was known for getting the best out of his players by
developing one-on-one relationships and treating each person as an
individual. He was blunt and he was fiery. He was infamous for,
allegedly, punching a fan squarely in face who came at him.

Red let players make their own decisions on the court, but demanded
they play right and as a team. Red created the concept of “hit the
open man.” Basically, get the ball to the person who was open–doesn’t
matter who.

He was fiercely loyal to his people and hated by opponents–by design.

Compare that to the self-centered “I need to get mine” NBA of today,
where superstars try to take three players on at once just so they can
fill out their stat line and perhaps get a highlight feature on
SportsCenter. Oh yeah, doesn’t hurt to pump your stat line when
everyone’s playing for their next contract. I suspect that the reason
Phil Jackson is always a year away from retirement is somehow related
to this trend.

You get old, the world changes and–at least here in the US–character

We live in a decaying empire and if you want to know what’s killing
us, it’s not the Chinese, bankers or politicians–it’s the trophy
generation. Not all of Gen Y, you can never paint with that wide of a
brush, but the majority of them seem to lack killer instinct but have
excel at entitlement.

Can our lot surprise us when the default has shifted from sacrifice
and drive to entitlement?

You’ve Got Mail!
An email with the subject line every CEO loathes: Resignation.


Another promising Gen Y-er leaves after one year and a couple of days,
shockingly right on time to vest their first cliff of stock options
(25%). Via email? At nearly midnight? To go to a 15-year-old
competitor that we’re trying to crush?

No “hey boss…” discussion? No “I know it’s unprofessional to leave
after 12 months, but I feel this is an important career move. Can I
explain my thinking?”

CEOs and founders understand that folks leave, but that discussion is
customary. A late-night resignation email isn’t appropriate. The most
frustrating part is not losing a great person–which happens–but
rather watching someone with promise set their career back five years
in order to have their salary jump ahead by three years.

Trading massive advancement to pop your salary, is a career move I
could never understand. Back in the day when I was employable I would
never have made that trade off–instead I cultivated my network.
Nothing puts me on tilt like talented young people trading long-term
rewards and career development for short-term greed and negative

“Congratulations on being employee 4,235 at a dying company” was the
most I could muster as an e-mail response while parked at a light,
getting on the 10 freeway. Oh yeah, today was your last day. And since
you’re going to a competitor, please don’t show up at the office.

Right after I hit send I had that familiar moment: “did I really just
say that?”

It’s not easy being me. I’ve got a version of tourette’s where instead
of yelling obscenities at inappropriate times, I say something
brutally honest without regard to my reputation or the other person’s
feelings. There’s no reason to make the kid feel bad on the way out
when I could have just said “Good luck, we will miss you greatly!”

What’s the benefit of telling people how you really feel when the
result of doing so only results in unpleasantness?

C’est la vie. No one is perfect. We all have flaws and the best we can
hope for is that our virtues outweigh them right?

Oh, it turns out my response is now on your blog, Hacker News and TechCrunch.


I wonder if there is any lemonade to be made out of these lemons?
Let’s try shall we?

Background on my Gen Y Rant
My belief is that one third of Gen Y kicks ass. I meet these folks at
TechCrunch50, Open Angel Forum and on This Week in Startups all the
time. I love them. They inspire me and give me hope.

However, the majority of Gen Y seem to operating under the bizarre
rallying cry of: More money! Less responsibility! Shorter hours! No
stress! More freedom! It’s all about me!

It’s so obvious to me why our country is spiraling like a regional jet
piloted by a $9 an hour, 20 year-old pilot with under 1,000 hours of
flight time.

Red and Phil wouldn’t tolerate it and neither do I. If you put
yourself above the team, you’re out. If you think your “get” is more
important than the team’s, you’re out.

If you leave after a year, you don’t get a ticker-tape parade and you
don’t get celebrated. It’s not always about you and your karaoke going
away party–after 90 days! (really? 90 days and you host your own
going away party? lame.)

… but moving on.

How to resign
Since we’re on the subject of how to do something uncomfortable like
resigning, here is my road map.

1. If things are going well at the company, and you’re learning and
developing, you should stay three years–at least. There is no reason
to jump ship if you’re learning and enjoying your time at a company.

2. If you’re not learning, enjoying yourself or developing, you
probably shouldn’t stay in a company. On that, I think we all agree.

3. Ask your boss if you can take 10 minutes of her time to speak in
private. If your boss is busy, ask their admin if you can get on the
schedule and say that it is urgent.

4. Tell your boss everything truthfully. Tell them why you’re leaving,
where you’re going and what you’ve loved about working at the company.
If they ask, tell them what you think could be improved.

5. If you would rather stay at your company, but need to make more
money, be straight with your boss and let them know you would like
them to match, or come closer to a competing offer.

6. Don’t post correspondence of any private discussions with your boss
on the Web. That’s not good for anyone–even though it’s highly
entertaining for many. 🙂

Here is a basic script for a situation where you absolutely want to leave a job:

“Boss, this is hard for me to say, so I’m going to just come out and
say it: I’m resigning today. Don’t worry, I will give you as much time
as you need to transition–within reason. It’s not personal, but I
really want to take on this challenge at company TKTK. I understand if
you don’t want me here in the office as a distraction to the rest of
the team. Please let me know how I can help us all have a really
smooth transition.”

Here is a basic script for the situation where you would rather stay,
but need for some things to change in order to do so:

“Thanks for taking the time to talk to me today, Boss. I wanted to let
you know that I’m considering leaving the company and have received a
compelling offer at company TKTK. However, I would much rather stay
here if a couple of small things could change. Would you like to hear
what those things are?”

If you say that script to almost any boss–including a fiery one like
myself–they have no choice but to be reasonable. They may be upset at
losing you, but they can’t really be upset at you. Every year, I have
five people come to me with one of these two scripts. In every case,
the person leaves on good terms or we figure out a way to make it
work. Generally speaking, 3/5 leave and 2/5 stay.

The Value of Loyalty
What you gain by dedicating yourself to a company, leader or project
for three or four years is much greater than what you give up, more
often than not. Again, if the company is not a fit, or you’re not
learning and growing, than no one would expect you to stay. We’re
talking about the value of staying at a good company with good people.

Loyalty is “trust + time,” and as you get older you value loyalty more.

Since this is the case, it’s good to start your career by being loyal
to the more senior folks around you. This makes them want to help you;
not just now, but for the rest of your life. Older people, especially
successful ones, are suckers for helping young people. It’s a trait
based in equal parts narcissism (i.e. “I see myself in him” and “I
discovered her”) and sentimentality (“we’ve been together and seen a
lot, huh, Tyler?”).

As a young person, you should work the loyalty angle. Keep in touch
with your former bosses and take them to lunch or dinner whenever you
can. This gratitude exercise will do more for you than it will them.
Trust me, I know, because I take my first boss out to dinner three or
four times a year, whenever I’m in New York City.

One of the best advantages our society and economy has is our
free-flowing talent marketplace and the fact that companies can reboot
or pivot at any time (within some basic constraints). We don’t want to
lose that, but we don’t want to reward and build a culture of job
hopping–it’s dysfunctional and short term.

Mark Suster did a really good blog post about why he doesn’t hire job
hoppers if you want another perspective on the same issue:

My Loyalty Pledge
I’ve never outlined how important loyalty is to me explicitly, but
since I’m involved with so many companies and projects today, perhaps
it would be beneficial to outline exactly what I’m willing to do–and
have done–for my peeps. “My peeps/people” being defined as partners,
investors, bosses and employees.

I realize it is absurd to outline in detail what loyalty will earn
from me, but I never thought the average expected employment period
would drop from four years to one! Then again, people gave my
generation a hard time about “only” working at a company for four
years! I know, it’s hard some people to believe but I remember many
people in the 90s questioning two, three and four year stints, saying
“why did you only stay three years?”

There is tremendous upside in being loyal and I’m going to outline it
for folks. If you are thinking about working with my it’s a FANTASTIC
deal provided you’re hard working, loyal and resilent. If you’re not
hard working please, for the love of God, do not apply for a job with
me. I have an insane work ethic that is modeled after watching my
mother work three jobs to put three boys through private Catholic high

Every work day of my life I’ve tried to work half as hard as she did
and on some I actually did so.

If you put in at least three solid years for me here is what I’m
willing to do for you:

1. Have a meal or cup of coffee with you at any time to discuss your
career or help you brainstorm you next company.
2. Introduce you to anyone I know with a sterling endorsement (if you
lasted three years working for me, then by default you are awesome).
3. Help you find a job at any company in my Rolodex.
4. Mentor you when you start your own company.
5. Introduce you to venture capitalist or angel investors.
6. Help you prepare yourself for being at TechCrunch50, Open Angel
Forum or any other event I run.
7. Be an advisor or possibly on your board of directors if you wanted
me to (provided it’s a fit).

This is just a high-level snapshot. I’m sure there are dozens and
dozens of things that people have done for me and that I’ve done for
them that don’t fall into these bullet points.

If you want examples of this, I can show you many.

1. Brian Alvey worked for me at my first company, Silicon Alley
Reporter. He was my full partner at my second company, Weblogs
Inc.–which I BEGGED him to do with me. When he was looking to start
his own firm, CrowdFusion, I did everything I could to support him,
including introducing him to at least 20+ investors.

2. Peter Rojas and Ryan Block worked with me at Weblogs Inc., building
Engadget. I told them that the second they figured out what their
startup would be, I would a) invest and b) tell everyone I knew that
they should invest. I also offered to be on their board of directors
if they wanted. I’m happy to report that I’ve participated in both
rounds of funding for their company and that I’m on their board. Any
chance I get, I tweet, retweet and promote their amazing product. I’ve
set up meetings with companies outside the US to try and get them
partnerships, and told sponsors that they HAVE TO support GDGT because
it’s such an amazing product.

3. Shawn Gold worked with me  at Weblogs Inc. and was a huge piece of
our success. When he was building out CoCoDot, I did everything I
could to support him, including acting as a reference for due
diligence from his impressive investor list.

4. The companies from the three years of TechCrunch50 are all on my
support list. I will tweet any new product update or future company
they are involved with. I will help them find financing and I’ve even
invested in one of them recently.

5. Brian, Peter, Ryan and Shawn from the first three examples above
have all been on my show, This Week in Startups.

6. Mark Jeffrey was the CTO of Mahalo for three years and I’m happy to
say Kevin Pollak and I made him a full partner and CEO of my latest
company, This Week In Studios ( I wasn’t upset
when he told me he was looking for a new challenge after three loyal
years at Mahalo. In fact, I thought “gee, what gig can we get you next
to make you even more successful?”

7. Jason Krute has been my loyal assistant and operations manager for
over three years. He’s carried my bags, gotten me mochas and crawled
under desks to rerun cables all night long at TechCrunch50 in order to
keep the Jason show on track. I’m happy to announce that he’s just
become the GM of my other new organization: Open Angel Forum
(www.openangelforum). He’s running it!

8. Whenever anyone attacked Mike Arrington over the past three years,
they heard from me. Any criticism of Arrington in my presence or on
the Interwebs was met with a quick and decisive response from me. I
didn’t need to know the facts; I was automatically on Mike’s side.

I’m old, I’m sentimental and I value–maybe even overvalue–loyalty.
Take advantage of it! That’s the smart thing for young folks to do!
Invest in crushing it for your boss today, and have them in your camp
for life!

There is NOTHING I wouldn’t do for the people who have helped me get
where I am today and who are helping me build my current crop of
projects. The reason to work hard is to build great things and share
that success with your friends and family! You can’t do this by job

For the current crop of team members at my companies, you can know
that my pledge to you is one of undying support, provided you put in
your time and effort. Three years is a small price to pay for having
me in your corner the rest of your life.

Bottom line: If you’re a flake I won’t even remember your name, but if
you’re loyal I will sing it in praise from on high.

It may not be your philosophy, but it’s mine and it’s worked really well for me.

Red Holzman was intense and he had as many detractors at times as he
did supporters at times. However, his undying love and loyalty for his
people–and the time he took to help develop them–is what defined

You could easily write a book filled with criticisms of Red, but you
would fill a library of books commenting on his virtues.

Good luck peeps.

best, Jason

Questions (answer any, all or none):
1. Who are the flawed leaders you admire most and why?
2. What are the pros and cons to the world view I’ve outlined?
3. Compare and contrast the leadership styles of the Phil Jackson and
Red Holzman. Do you have a preference? Why?
4. What would you like me to write about next?
5. How would you define loyalty?
6. Did you get this? I moved to a new email system and I’m not sure if
anyone is getting this.
7. Is the Gen Y issue real or all in my head?

To subscribe/unsubscribe visit: or email

sent from sunny Santa Monica with love

Jason McCabe Calacanis
902 Colorado Avenue
Santa Monica, CA 90401

3 thoughts on “Red, Jackson, Gen Y & Loyalty

  1. Great post jason,

    I didn’t get this in my email (so I guess that answers question 6) so I am going to reply on here. I don’t mind if others see my answers.

    1. All leaders are flawed as all humans are flawed and its simply about accepting that fact and only taking the best from their personality. In life I seek to find as many mentors and leaders as possible. I see the their personality and attempt to aggregate the most positive and influential parts of their personality. Learn from their mistakes and faults while emulating their strenghts and convictions.

    2. The con is that it simply seems very harsh, but the pro is that you show through it as an example of the ‘light at the end of the tunnel’

    3. —

    4. I would find anything related to your start very interesting. I know the basic story, but some real stories of specific instances would be a great read. If thats too personal, talking about specific ways to get into the tech/startup industry and general startup tips are always a great way to go.

    5. I would define loyalty as respect, trust, and assurance gained over time. Its premature and naive to say someone is loyal after just meeting them. You can trust them to start, but after months and years of them being faithful to that trust, you know they are loyal. I put respect in there because I feel there is no loyalty if there is not mutual respect in the relationship. No matter if it is your boss, your employee, your coworker, or your friend.

    6. I’ve been signed up for the jasonnation email list for a month or two and i’ve got nothing unfortunatelly. Tried unsubscribing and subscribing again today, so lets hope it works out.

    7. I am 21 years old and I can say first hand you are not making this up. It permeates everyone in my society. I am lucky enough to have friends who are not among that group, but not all my friends are in the 20%. I would like to consider myself the group that is “about to kick ass” I havn’t kicked any yet, but soon. I am a samurai in training, if I can steal an analogy.
    So many people of my generation feel so lost overall, they have zero motivation to do anything, its all about what feels good. What will get them by. I wish I knew the answer, but I don’t. Perhaps something will shake them out of their complacency as they get older, but more than likely it wont.

  2. Jason,
    Nice post on Resigning. As an executive recruitment consultant, I would disagree with number 5.
    I would not solicit another offer first. If your only issue with your current employer is compensation, I would have the compensation discussion first and see if your employer recognizes your contributions and rewards/compensates your fairly before looking elsewhere. Some employers may question your loyalty, if you come to them with another offer or try to “gangster strong arm them( a Jason term )”. Some employers would even match that compensation to buy them time to find your replacement. Also, there is loyalty loss and a burned bridge with the potential new employer and recruiters by getting to a formal offer and not accepting. In short, I would have that talk before looking elsewhere.

  3. @mark I disagree on a few points. Other offers are essential in determining the market value, ow it us really hard to guess what is fair. And I disagree that bridges are burned when you reject an offer, unless you do it in a very disrespectful way. On the contrary, a very strong bridge is built because now that company knows that you are good and that they want you, and will most likely check with you periodically to see if the situation has changed.

    As far as the question of entitlement and loyalty goes, I would not jump to conclusions that the source of it is in the young generations. The world is much faster now and the message that you send by firing people as soon as the recession starts is that they need to leave on their own when the times are good. Because noone is loyal to them when they need it. So I would not take any of this personally, its just the cost of running business. If you want people to stay longer you need to anchor them with more equity, if indeed they are worth. If not, then why are you sorry they left?

Leave a Reply