Last week David Cowan of Bessemer Venture Partners joined the Startup Grind Meetup for an hour-long chat with a packed house. More than 20 of David’s startup investments have gone on to IPO. His historical portfolio includes: Flycast, Hotjobs, and Playdom.

David told some amazing stories like the founding of Verisign (which he co-founded), the founding of Smule, and other insights into the Venture Capital and startup world that offer a rare glimpse inside theinner workings of a top Venture Capitalist. You should also follow David’s blog and Twitter feed.

Video highlights:

3 mins – David’s journey to Venture Capital
8 mins – The founding of Verisign
15 mins – The hiring of a great CEO
19 mins – How startups have evolved in the past 20 yrs
26 mins – Founding of Smule
35 mins – How to pitch a top tier firm
37 mins – The defining characteristic of a great entrepreneur
43 mins – As a first time entrepreneur, what would you do…

To the VC, Incubator, Angel, Blog Writer, Conference, and Cynic nearest you,

I just want to let you know that I’m really sorry that I’m not Mark Zuckerberg like you had dreamed. I know when we talked you had high hopes that I would be, and if you had just asked me at the beginning of the conversation, I could have told you.

I’m really sorry that I didn’t drop out of college. My brother did though – I could introduce you to him.  I didn’t get very good grades either because I was constantly trying to start a business – sorry about that. I didn’t go to an Ivy League school either – really sorry. Dang it. Sorry.

I’m sorry that I didn’t get the perfect product on my first try. I know how much you’d like me to just get a grand slam on the first pitch but that’s not really me. So sorry. I mean we’ve built 5-products in the past 18 months and created a business that currently supports seven people with no VC funding. I know that doesn’t really mean anything and I’m really really sorry for even thinking about it.

I know it would be great if I were curly haired and Jewish but I’m bald and Mormon. I’m sorry about that stuff. The hair is really out of my control, I know you’d like me to let it grow and rock a bandana but that’s not me. The Mormon thing is tough too – sorry (well not really). I think the House of Isreal is awesome though. Go Jews! That came out all wrong…sorry Jewish Angels, Bloggers and cynics.

I’m really sorry I’m not single and don’t stay up all night drinking beer and doing drugs. I have a wife and a baby that I’m told reminds people of Hugo Chavez as a child.  I often stay up all night working (like tonight) but I never quite hit Ballmer Peak (Mormon thing again, sigh). I feel horrible. I have as stable a life as you possibly could while running a startup, and I’m not a horrible guy to hang out with. I should have told you that at the beginning. Totally un-investable.

Actually I’m really sorry I don’t code very often. OK pretty much not at all. I know I know, I’ve seen the pitchforks and torches before – you want me out of the Valley.  Plus I’m sorry that I partner with guys that do and are awesome at it. Too bad I don’t have any real skills that a startup could ever, ever, ever, ever possibly use. Just overhead, I know. No non-technical founders are ever, ever, ever, ever, ever successful.

Sorry I didn’t boast that my company would make you a $100MM or tell you how amazing I am. I like people in Silicon Valley that are more humble and let their success speak for themselves.  Sorry I didn’t beat my drums until your eardrum burst. I should have known better. The next time we meet I’ll do a Haka for you and bring a spear to stab someone. Should have known that would show my dedication to the business.

Sorry that I didn’t start my company when I was 19 and now I’m 28! When I was 18 I was on an island in the middle of the Pacific ocean for 2-years learning Maori, and trying to help people improve their lives (I wasn’t kidding about the Haka). I know that the lessons I learned getting doors slammed in my face have zero application for my startup. Sorry. Sorry for going to work for EAfor 4-years. What a waste. I knew that HotOrNot was gonna be huge – I should have jumped on board. Fail.

Sorry that my co-founders and business partners don’t generally hate me. Probably a bad sign that I still share an office with the guy that started Vaporware Labs with me even though it’s been over a year since we split. We should have yelled and screamed and sued each other. It is an action item for me to make progress on that for the next time I see you – which will probably be never.

I’m sorry that doing a startup got so cool all of a sudden. When I quit my job in 2009 in the middle of the modern depression, I was just trying to do what I thought was right. 10 different business pivots later here we are. Just horrible I know.


So if you couldn’t tell, I just wanted to say how sorry I am that I’m not Mark Zuckerberg. And if I could be – I wouldn’t. This is not to say what he’s done isn’t anything short of amazing – because it is. This is not to say I don’t hope the best for the guy and that he gets double rainbows every single day because, I do.

This is just an FYI that we’ll be over here plugging along, trying to build something awesome and successful. In the meantime, good luck finding that guy because if that’s what you want, you’ve come to the wrong place. So sorry. Just really really sorry.


One thing I’ve noticed talking to people about Commonred over the past 6 months is how the messaging has shifted. As customers use the product, as we meet with domain experts, as you think and think and think more about the product, the vision and what you’re trying to accomplish becomes easier to describe.

I saw an interesting example of this on Friday. @Arrington retweeted a link to a guy who is trying to get some attention for his startup called QuickVanz. I must say I absolutely respect this guy’s husstle and attempts to get the ear of tech’s elite as he messages basically everyone of influence in tech trying to find people that might be interested in the idea he’s working on.

Along the way you see his idea evolve. This is how it must be or he’s not doing it right. Even the name has evolved. The idea at times looks to have completely shifted, and then comes back.

It’s a quick read. I’ll list them in chronological order until you get to Arrington’s tweet at the bottom. Watch the dates of the posts.

I take a lot of random meetings. I meet with entrepreneurs, founders, and new friends that come to our meetup. Some of these produce great partnerships, most do not. Some have immense direct benefit to me and my business, but most do not. Considering I built a site to get out of meetings this practice probably seems like a contradiction but it’s not and I will explain.

I take almost any meeting for a couple of reasons in order of importance:

1. I know what’s like to have no one care about your startup and ideas. If I can just be helpful enough to encourage someone not to give up and keep pushing for another month, then it’s worth an hour to me. That energy motivates me to be better.

2. The ability to sit for an hour and brainstorm a completely different concept or idea, learn about someone’s business, and inject my background is very rewarding and beneficial.

3. If you get access to enough pieces to the puzzle you eventually start to see patterns the right ones to use for your business.

Let me give you two examples just from Friday.

*I met with a guy and we brainstormed and drew out the new layout for his website on my whiteboard. He then said he wanted to make an introduction video for the homepage but had a small budget. One month ago I met with a guy whose company makes quality cartoon intro videos on the cheap through crowd sourcing. They’re a perfect match for each other. Everyone wins (especially me – I feel good).

*I had lunch with a guy who said he wanted to give me a million dollar idea for FREE. After listening I wasn’t sure his idea is worth a million bucks, but a small piece of his idea works perfectly to solve a problem we’re having on a current project. I told him thanks for the business idea, but I would use a small piece of it for something else.

This kind of thing happens ALL THE TIME. When we’re getting exposed to lots of people we see different perspectives, encounter foreign problems or solutions, and are able to apply those to our own business needs.

This video called WHERE GOOD IDEAS COME FROM is something I’ve watched a dozen times. There’s no better way to explain how this concept works, and how it can lead you to world class ideas.

There are a lot of things people can say about that aren’t nice that are also probably true. I’m cheap, I’m inpatient, I’m bald, the list goes on for days. One thing I hope no one ever says about me is that I’m dismissive or unapproachable. I’ve met so many people like that in Silicon Valley it’s sad. I won’t go into great detail, but the guys that are humble and totally helpful are few and far between. I will tell you about three of the five most humble guys I’ve met/spoken/emailed with including Naval Ravikant (AngelList), Jeff Smith (Smule), and Sassan Golafshan (Form Fitness Founder in Palo Alto).

I’ve had limited interaction with Naval, but the little time I have spent emailing him I’ve been hugely impressed. First off I don’t expect someone of his caliber to even return my email or Tweet (this is the norm apparently), but when they do with thought and meaning, it really means a lot – because it’s rare. My brief experience with Naval was that I could have been running a $100MM or $1MM company and I would have received the same email. He didn’t treat me differently based on who I am, or the lack of who I am.

Jeff Smith, CEO at Smule is another guy that exemplifies this. He sits with you and thinks hard about what you’re saying, asks tough questions, but looks for great answers. Jeff has been an instrumental supporter to our startup since the very early days of Vaporware Labs. Once I asked Jeff what I could do to repay him for all that he’s helped me with; his response was “Nothing. That’s not the point. I don’t want anything.” I would literally do anything to help him.

I had lunch with Sassan Golafshan a few weeks ago. Sassan is the founder of Form Fitness off University in Palo Alto. He came from humble begins as his family was forced to flee Iran in the early 1980’s due to the uprising. He’s part of an unorganized group I like to call Silicon Valley’s “Iranian Mafia” (I will blog about them soon). For no reason except love of entrepreneurship, he has opened up his Rolodex to me, offering introductions and invitations to some of the smartest entrepreneurs in the valley. Funny thing is that this open and happy spirit is present and obvious where you go to his gym or talk to his employees. Just read some of their online reviews.

And this brings me to my reason for the post. I got an email today from a guy whose startup has had modest success to date. Last year I wrote a glowing article about how cool I thought their company was and how people should watch it. I recently met a mutual friend who offered to make an introduction to the founder. Below is the exchange between us. I have removed he and his company’s name.

If this email had come from Kevin Rose then I could understand it. Remember that 99% of SV big timers respond this way. But when you’re not it’s much harder to understand. Plus if you’re a genuinely cool person you don’t respond this way regardless (ie – Naval, Jeff, or Sassan).

There are lots of other lessons to learn here like poor community management, terrible company PR (if I published the names), sales/Business Development (I was going to intro him to a potential Fortune 500 client), and bad Karma overall.

But ultimately this just reaffirms in my mind the need to never become like this no matter how big or small (more likely) I become, and writing a blog post about it keeps me honest.

A couple of months ago I posted a question on Quora called, “What’s the best way to get a meeting with Never Eat Alone author Keith Ferrazzi?” For those that don’t know him, he’s one of the leading relationship experts in the world. His book Never Eat Alone was a big inspiration for our project Commonred.

That’s when the Quora underlords (perhaps a bit strong) joined the conversation. How/why they found this question I’ll never know. Rest assured it’s way down at the bottom of the moderation list.

The question stands: where is the line for a company to maintain the integrity of their product’s purpose, and just chill out? Not sure but Quora crossed it on this one. My personal philosophy is to always air on the side of being chill because in the grand scheme of life, how important really is your startup?

See the response and conversation below. A small ‘big ups’ to Chelsea Henry for responding in the first place. She’s merely a pawn in the great game of startup chess. Don’t worry Chelsea, I’m not even a piece on the board so at least you’re that much.

I had a great weekend visiting with family and friends in Utah. Twice per year we attend General Conference – two days worth of LDS meetings where we listen to spiritual leaders talk about how we should be better husbands, fathers, and brothers and sisters to the people in the world around us. Very inspiring.

My family and I also usually spend some time with my parents. My parents have always been very involved in my life. My mom helped me get my eagle scout, and get my first business in high school off the ground (painting hop scotch on driveways. yep). My dad attended many a teacher-parent meeting that weren’t during the scheduled times (I was that kind of student).

But when I quit my job in mid-2009, the future and the economy looked bleak. I remember a conversation with my dad where he seriously questioned if quitting my job with no incoming revenue stream awaiting me was a good idea. These were sound criticisms. I didn’t have a great plan. The idea I planned to work on fell apart in 3-months.

But after about 6-months, (and a couple of closed deals) when it was clear we wouldn’t starve, his advice changed to “You’re doing it. You can do it.” It’s now been about 18 months since I quit and while talking with him this weekend, I mentioned a doomsday scenario where if worst comes to worst I could go get a job again. He then responded with the most direct and true thing anyone has said to me in a long time: “You can never go back.”

The Background

He then proceeded to tell me a story of when he was working for a major advertising agency in Florida. He asked for a part-time leave of absence which allowed him to pursue a real estate development project he was hoping to land and would eventually quit his job to pursue. Unfortunately the deal fell through and he had to return to work full-time at the agency after about 6-months.

The problem he said was that he had tasted how good the outside and self-employed world felt like, and returning to the agency only left a huge whole in his professional stomach. My dad eventually started his own agency which boasted many successful accounts including Jack Nicklaus’ golf courses in the Southern United States.

Standing in the driveway this past weekend, he explained that I could never work at a big company in the same capacity as before because I would never be satisfied. As a result and regardless of the obstacles, I would just have to “make it work and figure it out.”

As entrepreneurs it’s natural to want to hedge. But hedging is a sign of an inexperienced talent. If you don’t burn your boats, you run the risk of always leaving that door open. I’ve received advice about not hedging many times by well-known CEOs. But this is the first time it’s really sunk in.

Not that I ever planned to go back, but the small chance of it happening went to zero chance within about 10 seconds.

There’s been a lot of talk about the decline of the value of Google search over the past few weeks. What baffles me is how iTunes search has been able to fly under the radar for so long without someone punching it in the face. It is so bad. I mean seriously, it’s awful. Even worse is that it has been as long as I can remember. What’s so bad you ask? How much time do you have?

*Design – The iTunes search design is nails on chalkboard bad. Seriously. Listing out every possible category and making me scroll for miles to eventually figure out that it didn’t find what I was looking for. It’s extremely inefficient wasting precious time and effort on my part. For the record I’ve never searched for an album title in my entire life, but I’ve probably seen thousands in my search results.

*Speed – Word association game…Road Runner is to FAST what iTunes is to SLOW. I feel like iTunes is about to explode into shrapnel every time I search. What’s taking so long? Maybe the MSFT paperclip takes my query, gets on the 101 freeway, drives to Cupertino, stops at the Apple cafeteria for a quick bite, then gets engineering to fulfill the request, and returns it back to me in Mountain View. It’s plausible.

*Results – This is my the biggest gripe by far. If the results were good, I could probably get over the other problems. Heaven forbid you don’t know the song name exactly the way it’s spelled. Good luck if the savy app developer couldn’t get ‘Runs’ for his hot new app and decided to go with ‘Runzz’. Spelling bee kids lose to iTunes every time.

*User Experience – Here’s my flow for searching iTunes:

1. Open iTunes.

2. Go directly to Google.

3. Search song title, artist, app name, or podcast.

4. Go back to iTunes.

5. Click on the iTunes Store button.

6. Enter word in the search bar.

7. Get bad results.

8. Return to Google and try to find a different spelling, name, or secret key to unlock iTunes search.

9. Go to a quiet corner of my office and cry.

For the love of all that’s good Apple, please fix iTunes search or at least tell people it’s powered by AltaVista. It’s cool if it is. I’d just like to know.

I was cleaning out a drawer recently and I came across the business card for Living Social CEO Tim O’Shaughnessy. In early 2009 we setup a meeting with the hottest Facebook app developer called Living Social. I remember going to their website and reading about the Washington DC based company with a founding team from Revolution Health (?). But now they were hottest Facebook app developer on the planet.

In terms of app developers, at the time theirs had a major hockey stick. Quizzes had just started hitting the user feeds and these guys had the lion share of the popular ones. The numbers he was throwing out were mind blowing.

As Tim walked into the meeting, he had a beat up suit, a wrinkled white shirt, and he looked like he’d been traveling for a week. Nothing he said overly impressed or shook the room. He reminded me of a lot of guys I went to college with in Provo. He was just a nice, normal, mellow guy who founded a company and worked hard with his friends to grow it.

We tried to work with them but it didn’t pan out. As quickly as Living Social had exploded onto the sync, the quizzes were gone like Jean Valjean in the middle of the night. Facebook cutoff their feed access and that was pretty much the end. I don’t know full transition story, but obviously the company pivoted from apps and took a huge roll of the dice to go with the group deals market and they exploded again.

The amazing thing about Tim and Living Social is to think how high they were at the top of the Facebook app world, to then have it all crash down, but then rebuild it all again. Amazing. Maybe he’s a brilliant guy who had an off day with us, but I don’t think so. He’s a normal who has put it all on the line several times, and with the big ups and downs he’s been able to pull out a huge win for the company. He’s a grinder for sure. From on top of the app world, to the floor falling out, he kept pushing and found a way to successfully refocus the company and rebuild (read: pivot).

For all the slack ‘pivoting’ is taking right now, there are some tangible examples of incredible companies that were pivoted into brand new business models from what they set out to create. Something to keep in mind if you’re looking at a new direction from where you originally started. It’s not all bad, just maybe find a different word to use if you’re telling someone about it.

When @Jason Calacanis posted this on Twitter this morning I had to share it. It’s about as amazing as YouTube gets. I wish I’d had some role in making it.

To Freezecrowd: You just blipped on my radar. Put me down for some angel funding when you need it.



Get every new post delivered to your Inbox.

Build a website with
%d bloggers like this: