Costolo’s Awesome Commencement Speech

“We must be willing to let go of the life that we’ve planned so as to embrace the life that is awaiting us.”
— Joseph Campbell

I am a commencement speech junkie. Dick Costolo’s most recent one is in the top 5…funny, inspirational and spot on about life. I first met Dick 16 years ago just after he had launched his first company. We came close to investing in his second, Spyonit, just as it was being acquired and ended up seeding his third, FeedBurner (acquired by Google) before he headed to Twitter. When he and his 3 co-founders spun out of Accenture, they were indifferentiable from any other young group of entrepreneurs. It is amazing how life/Universe/God/whatever you call it has a way of helping those who take intelligent risks and make courageous choices to “follow their bliss”. Life is linear when you look back and completely non-linear/opaque when you gaze forward. As Dick says, “There is no script. Live your life.”  Take the time to watch this video and then think about ways in which you can make more courageous choices in your life & make “unreasonable requests” (a favorite phrase of Dick’s and Jack Dorsey’s) of your life and of the world around you.  Break out of having lives of quiet despiration and embrace the future that awaits you.  While it may seem riskier now, in the long run, it is much riskier not to…

Some great quotes pulled from the video by the ever brilliant, Bill Gross (don’t know when you sleep!)

  • “You need to make more courageous choices. Take courageous risks.”
  • “You can’t plan a script. BE in THIS moment.”
  • “When I was your age, we didn’t have the Internet in our pants. We didn’t even have the Internet NOT in our pants!”
  • “When I was your age, we didn’t have teeth. There were no question marks, we just had words!”
  • “Not only can you not plan the impact you are going to have, you often won’t recognize it even while you are having it.”
  • “The impact is what others frame for you and the world, AFTER it happens. The present is ONLY what you are experiencing and focused on right now.”
  • “You cannot draw ANY of of yours looking forward, so you have to figure out what you love to do, what you have conviction about, and go do that.”
  • “When you are doing what you love to do, you become resilient.”
    “If you do what you think is expected of you, or what you are supposed to do, you will look to external sources for what to do next. You will be standing there frozen on the ‘stage’ of your life.”
  • “Believe that if you make courageous choices, and bet on yourself, then you will have an impact.”
  • “Don’t always worry about what your next line is supposed to be. There is no script. Live your life. Be in this moment.”

Curiosity, Obsession & Dogged Endurance

“I know quite certainly that I myself have no special talent. Curiosity, obsession and dogged endurance, combined with self-criticism, have brought me to my ideas” — Albert Einstein

As I look back over my life, the most successful or content people I know were not the most brilliant but the most determined and disciplined. Excellence came not from revolutionary thought but from dogged execution and focus. Having a passion for the topic cause was also baked into this. Because of their focus, they iterate more quickly and come up the learning curve faster. Lack of focus (on the right thing!) versus an array (all parts of the value chain vs two, 5 channels vs getting a couple profitable) is the #1 cause of failure. So what?

Well, it means that anyone has the potential for success in endeavors small or large. I look at my kids’ classmates and the some do well because they are brilliant. However, most do well because they start their work early, engage their teachers, ask when they don’t know (comfortable with their vulnerability) and have an interest in learning. And they are focused.

The same is true in entrepreneurship. Some are brilliant but most are passionately focused. Many times in fundraising or in ramping sales, I’ve concluded it just wasn’t going to happen but someone forgot to tell the entrepreneur. They would iterate, test, get rejected, regroup, reach out to even more people (again no feeling embarrassed or vulnerable to approach), iterate until they figured it out. Sometimes the three month process would stretch to nine. But forward they go with focused determination.

This is why I have a passion for what I do. I love watching this entrepreneurial dance. I’m amazed by all of your determination and unflappable spirit. My purpose is simple…to help you realize this full potential, to provide shelter from the storm and to help prevent self-inflicted wounds.

The good and bad news is, as Einstein pointed out, that this is pretty straight forward. Execution, focus and discipline is the thorn…

Now go out and change the world for the better 🙂

Success vs Struggle: The Art of Compartmentalizing

Ryan Blair posted an interesting piece The Five Steps of Compartimentalization in Forbes last year.  I did an exercise I try every couple of weeks where I lay out all of the commitments I had made ranging from board meeting follow-ups (intros, offsites, etc) to family matters (coaching, attending, traveling) to new deals (diligence, meetings, etc) to everyday stuff (sports, working out, yoga) to email & a host of other things. When I was done, I had about 35 commitments and felt that sudden moment of dread we all get when we see 10 lbs of crap and a 2 lbs bag to stuff it in.

There are a whole host of things to help with this that I'll blog on in coming posts such as daily routines, sharpening the saw, etc. One of the key ones is Compartimentalization…breaking things down in distinct blocks, focusing on each block solely at a set time and rotating to the next one. Further, prioritize the blocks and define 3 key "must do" for each day and do them early in the day. Some are short term and others long term. More to come. Anyways, here is an excerpt from the post…like the imagery.

"Here’s a visual for compartmentalization; pretend as if everything you’re dealing with in your life is a room where you have to walk in and solve an equation on a white board. You have a countdown clock with less than an hour to get the problem solved, or take a single step in the right direction, and then shut the door and go into another room equally as important. You spend your entire life going from compartment to compartment."

Build those rooms…

Byron Wien’s 14 Lessons after 80 Years

Some of you might know Byron as the Vice Chair of Blackstone Advisory or as the Chief Investment Strategy Officer at Morgan Stanley for over 20 years. Each year he publishes two of the most read pieces on Wall Street "10 Surprises for the Coming Year" and "Lunch with the Smartest Investor in Europe". I recently saw this, loved this and thought I would share his 14 lessons:


  • Concentrate on finding a big idea that will make an impact on the people  you want to influence.
  • Network intensely.
  • When you meet someone new, treat that person as a friend.
  • Read all the time.
  • Get enough sleep.
  • Evolve.
  • Travel extensively.
  • When meeting someone new, try to find out what formative experience  occurred in their lives before they were seventeen.
  • On philanthropy my approach is to try to relieve pain rather than spread  joy.
  • Younger people are naturally insecure and tend to overplay their  accomplishments.
  • Take the time to pat those who work for you on the back when they do  good work.
  • When someone extends a kindness to you write them a hand-written note,  not an e-mail.
  • At the beginning of every year think of ways you can do your job better      than you have ever done it before.
  • Never retire.


What Entrepreneurs Don’t Tell You about the Fight

A little perspective from up North. Our Canadian portfolio CEO, Guy Gal, forwarded over a great piece from StartupNorth titled The Things an Entrepreneur Will Never Tell You. It is definitely worth a quick read as entrepreneurs often feel they are unique in what they are going through in terms of high's & lows, feeling alone, handling the spectre of failure, letting others down, etc. Generically, entrepreneurship is a gallant fight to change the world (or your sector) but it is critical not only stop putting the entire burden on your shoulders but also to "lean into" or embrace the various specific elements of this burden.

For example, fear of failure is a universal one for everyone (entrepreneur or not). What will people think? Who am I disappointing? What will this mean for my future/career? What is the financial impact? The reality is, the sun will shine tomorrow regardless. Unless failure means someone "shooting you in the head" (Dave McClure quote), you'll have another bite at the apple. You likely won't starve on the streets; you'll find another job or start-up; your family (and investors if you handle things with diginity & fairness) will love you.

So, regarding facing fear of failure, I think the core of the Samarai code said it best. A little deep thought here.

"If by setting one's heart right every morning and evening, one is able to live as though his body were already dead, he gains freedom in the Way. His whole life will be without blame, and he will succeed in his calling." — Hagakure

What this means is that the Samarai gets comfortable with death (he is already there and all is upside) and enters battle fully committed and without fear. In the case of an entrepreneur, he/she must realize that failure is survivable, not terminal. Picture what life would be like if it did not work…you'll realize life goes on. Then, go out with full commitment (and paranoia:) and change the world.

A good quote from the blog post above is about how entrepreneurs will often feel isolated or alone as they fight through their cause. Find outlets to talk about what you are going through. Again, it will allow you to be fully committed and able.

You learn quickly that you can’t take your problems home because one day you are up and one day you are down, or you might be both on the same day. It doesn’t feel fair to put that on your partner, and if you did they would eventually get tired of it after years of constant ups and downs.

You toughen up and you bottle it up. You are afraid to really talk about things because you can’t afford to open the bottle– it might knock off your focus and set your company back. That’s a no-no.

The best investors in the world know that entrepreneurs have this loneliness and they take time to give you a safe space to vent. Almost nobody else can give you this safe space and it takes a lot of work on both sides to develop a level of trust that allows it."

Take a look at the post and see what parts resonate with your own behavior and live to die another day!

Some MoreTeddy for the Weekend

A little something for you all laboring to improve the world through your entrepreneurial efforts (from my friend, Brian Johnson at Have a great weekend:)

“Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to take rank with those poor spirits who neither enjoy much nor suffer much, because they live in the gray twilight that knows not victory nor defeat.”
— Teddy Roosevelt

Inverse Paranoia

Love this concept which my friend, Brian Johnson, posted recently.  Great entrepreneurs have a sense of "inevitability" in the belief in their idea and mission. Jim Clark refers to it as "willing a company into existence". 

“My earliest mentor, W. Clement Stone, was once described as an inverse paranoid. Instead of believing the world was plotting to do him harm, he chose to believe the world was plotting to do him good. Instead of seeing every difficult or challenging event as a negative, he saw it for what it could be — something that was meant to enrich him, empower him, or advance his causes.
What an incredibly positive belief! Imagine how much easier it would be to succeed in life if you were constantly expecting the world to support you and bring you opportunity.
Successful people do just that.” ~ Jack Canfield from The Success Principles

Entrepreneurs’ Manifesto: Shame In the Arena

Great TED talk by Brene Brown on Shame and its role in innovation and society.

YouTube Link to Brown Shame Talk:

Terrific Roosevelt quote from it for all you entrepreneurs in the arena…I'll call it the Entrepreneur's Manifesto:

"It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat. "

Mission That Doesn’t Suck

Great piece from Aaron Levie, the founder and CEO of titled Be On A Mission That Doesn't Suck. In essence, he talks about the important of the purpose/reason of what you are doing. Without a sense of purpose beyond making money, flipping your company or being involved with a hip company, you will eventually come to dread your role/job. 

"As I thought about it more, I realized it was the mission we were on that compelled me to keep at it…As best as I can tell, this is the most important factor – in addition to the people that you work with every day – that separates going into the office and dreading your job or having the time of your life."

Great companies come from great missions and sense of purpose.

The best missions, it would seem, are those keep you cranking day after day. They’re ambitious, improbable, and fundamentally thrilling. Some of the loftiest are missions that can never quite be fulfilled. Google’s famously is “to organize the world's information and make it universally accessible and useful.” Starbucks wants to “inspire and nurture the human spirit – one person, one cup and one neighborhood at a time.” Whole Foods believes that“companies, like individuals, must assume their share of responsibility as tenants of Planet Earth.” — Be on a Mission that Doesn't Suck (Levie)

What is your firm's mission (not something like being the best at selling xyz but something aspirational like the above)? If you don't have one/know it, time to get crackin'…

Meaning, Balance & Productivity

An awesome quote about perspective for entrepreneurs out in the battle field from Jung (thanks to Carter Cast for sending over).

Mike Cassidy of Google, Microsoft, Xfire, Direct Hit fame ($1B), spoke at the DFJ CEO summit. When asked how hard does he burn his teams, he said home by 6:30 for balance (works email at night). Jason Fried wrote his team does more with their new 4 day week. Points out the law of diminishing returns, albeit more on the extreme.

“I have frequently seen people become neurotic when they content themselves with inadequate or wrong answers to the questions of life. They seek position, marriage, reputation, outward success, money, and remain unhappy and neurotic even when they have attained what they were seeking. Such people are usually confined within too narrow a spiritial horizon. Their life has not sufficient content, sufficient meaning. If they are enabled to develop into more spacious personalities, the neurosis generally disappears.”