Greg Gottesman's Blog

My Holiday Gift to You: The Funniest VC Video Ever

We may not know each other, but that doesn’t mean I can’t give you a meaningful holiday gift. I recently got an email from a high-ranking official in Nigeria offering to reward me with a huge amount of money if I just sent a few dollars to help someone wrongly accused get out of jail. I then got a similar email from a Ugandan prince. People are so giving this time of year.

So from my family to yours and without further ado, here’s Gary the Snoman!

http://FunnyOrDie.com/m/7ki

My favorite line (although there are a lot to

… Continue reading →

Posted on December 12, 2012 by greggottesman · 1 Comment

Do Diligence on Us

“Think of him as chewing gum. By the end of the game, I want you to know what flavor he is.” – Coach Norman Dale (Gene Hackman), Hoosiers

Entrepreneurs don’t do enough diligence on their investors.

As venture investors, we do a lot of diligence on you. We call references, both on and off your reference sheet. In our partnership discussion, we talk about your strengths and weaknesses, your character, your ability to grow the business, your idiosyncrasies, whether you will want to sell too early, your willingness to take feedback, and everything else under the sun. We are making a bet on you just

… Continue reading →

Posted on December 9, 2012 by greggottesman · 12 Comments

If You Want to Lead People, Stop Whining

George Marshall was a truly great American leader. Credited by Winston Churchill as the “organizer of victory” for his leadership of the U.S. Army during World War II, he also was awarded the Nobel Peace Prize for spearheading the Marshall Plan as Secretary of State. Marshall also owns my favorite quote about leadership.

“Gentlemen, enlisted men may be entitled to morale problems, but officers are not. I expect all officers in this department to take care of their own morale. No one is taking care of my morale.”

This quote has been interpreted historically

… Continue reading →

Posted on November 8, 2012 by GG · 2 Comments

The Best VC Pitch Ever

In the past 15 years at Madrona, I have heard in excess of 7,500 pitches. Some of them were great, some not so good, but not one compares to the pitch below.

In honor of TechStars Demo Day tomorrow in Seattle, I present to you . . . the Ice Cream Glove.

Posted on October 31, 2012 by GG · 2 Comments

Time Kills All Deals

On a long enough timeline, the survival rate for everyone drops to zero. –Narrator, Fight Club

No matter how compelling your product or service is, no matter how great the terms you are proposing, no matter how appealing you are as a promoter or sales person, given enough time, your deal will fall apart.

It won’t be your fault. In the last two quarters, I have heard the following from CEOs at various software startups.

“Our deal champion left the company.” “The budget shrank, so we’re off the table now.” “The buyer missed its numbers. Everything’s on hold.” “That company fell off the list because it … Continue reading →

Posted on October 23, 2012 by GG · 9 Comments

Most Underrated Movie Speech Ever

The four-minute speech below by Al Pacino’s character, head football coach Tony D’Amato, in Any Given Sunday is one of the more inspirational movie clips ever. I particularly like the part about teamwork. Below is the text from my favorite section.

Now, I can’t make you do it. You gotta look at the guy next to you. Look into his eyes. Now, I think you are going to see a guy who will go that inch with you. You are going to see a guy who will sacrifice himself for this team because he knows, when it comes down to it, you are gonna do the

… Continue reading →

Posted on October 19, 2012 by GG · 2 Comments

Raise More by Asking for Less

“I want to ask you a question… straight out, flat out… and I want you to give me an honest answer. What do you think the chances of a guy like you and a girl like me… ending up together?” “Well, that’s pretty difficult to say.” “Hit me with it! I’ve come a long way to see you, Mary. The least you can do is level with me. What are my chances?” “Not good.” “You mean, not good like one out of a hundred?” “I’d say more like one out of a million.” “So you’re telling me there’s a chance.” - Lloyd and Mary

… Continue reading →

Posted on October 16, 2012 by GG · Leave a comment

The Poem That Most Inspires Me

For college graduation, my parents sent me the following poem by Rudyard Kipling. I loved it then and have gone back to it often for inspiration. I think most entrepreneurs will relate to the poem.

If you can keep your head when all about you Are losing theirs and blaming it on you; If you can trust yourself when all men doubt you, But make allowance for their doubting too: If you can wait and not be tired by waiting, Or being lied about, don’t deal in lies, Or being hated don’t give way

… Continue reading →

Posted on October 11, 2012 by GG · 8 Comments

Someone Like You: An Ode to My BlackBerry

Never mind, I’ll find someone like you. I wish nothing but the best for you too. Don’t forget me, I beg, I remember, you said, “Sometimes it lasts in love, but sometimes it hurts instead. Sometimes it lasts in love, but sometimes it hurts instead.” –Adele, “Someone Like You”

I broke it off with the “other woman” last week. After well more than a decade, our love affair couldn’t withstand newer and better models. Yes, I’m talking about my BlackBerry.

I must admit I miss her at times. I miss that keyboard that I had grown so accustomed to

… Continue reading →

Posted on October 8, 2012 by GG · 1 Comment

Are You Best in the World at Something?

You would be shocked at how few entrepreneurs—even the best ones—have a clear understanding of how to answer this question (or have even thought about it).

Most great startups are best in the world at something, even if that something isn’t big at first. Think about recent success stories: Instagram, Facebook, Zynga, and so on. Each one was clearly best in the world at something very specific.

In my hometown of Seattle, multiple startups can claim they are best in the world at something. If you want to buy a home and plan to utilize the best online

… Continue reading →

Posted on October 8, 2012 by GG · 10 Comments