Random thoughts from the corner of University and Waverley

I’m in between my company demos and a CEO dinner Sequoia Capital is hosting tonight having some french fries and a huge diet coke at a place called “Taxis.”

Some random thoughts/updates:

  1. Is the folks in Silicon Valley are so loaded why does the food down here suck so much?
  2. I’m really proud of the work we’re doing with the TechCrunch40 event. I realized today while doing an interview with “The Deal” that the big difference between the TechCrunch40 event and the DEMO conference is not just that DEMO charges $18,500 to present for six minutes and that we are free (with a $50,000 grand prize).

    The most important issue is that we draw the *pre-funded* startups as well as the funded ones. A pre-funded/angel funded startup, by definition can’t afford DEMO. However, we selected companies on merit, not how deep their pocketbooks were.

  3. The fact that we have pre-funding companies at the event–and that we did the 100 company demo pit–has caused a TON of VCs and angel investors to buy tickets to the event. If you think about it this makes sense. At DEMO the VCs already know about the companies because they have already raised their first round (and are spending a chunk of it on DEMO!). So, why go see the folks who you’ve had in your office already. The VCs are flocking to TechCrunch40 because they know they might find the next Garrett Camp, Kevin Rose, or Joshua Schachter. Those guys wouldn’t have paid for DEMO, but they would have gotten into TechCrunch40.
  4. Turning off comments on my blog was the best decision I’ve made in the past six months.
  5. I’m sending at least one hour a day reading and responding to blog posts about Mahalo. I see this as an essential part of my “job” as CEO of the company. Of course, some folks have commented to me that I shouldn’t waste any time commenting on blogs and just focus on the product. I don’t buy that at all. The hour a day I spend talking to bloggers has paid off in a bunch of ways: a) I make relationships with folks who care enough about our product to write something, b) I learn about the product, and c) I learn about the human nature.
  6. Related to point five above, I’m amazed at how pessimistic the average person is. I’ve come to realize in my career is that the difference between people who gets things done and those who do not is this pessimism. I’ve always been attracted to the folks who say “what if we could…” or “what if you.” When I hear people talk like that I get engaged. When I hear “that’s been done already….” and “that will never work…” I want to walk away from the conversation. I guess that means I’m delusional on some level, and I’m realizing that the best products and companies out there are typically lead by delusional people who hire people who are very obsessive about details–but who are also dreamers.
  7. Talking to the 40 companies presenting, hearing them pitch WHY something is going to work has been totally inspiring and confirming to me. I love these people. I love people who try. I love people who dream. In another life I could have been a VC because listening to people talk about their dream and helping them make it happen is just frackin’ cool. To the angel investors and VCs out there I salute you. It’s got to be a hard gig at times (amazing at others), but you are very special folks to helping people make their dreams happen.
  8. I try to make time for entrepreneurs who have questions for me, but I’m not able to get back to all of them. I feel bad when I can’t, but I try. So, if you’re emailed me or IMed me and I didn’t get back to you I’m sorry. Realize I get 20-50 folks emailing me a day for advice and some days I’m trying to get advice myself! I don’t use the phone, so the best bet is to ping me on IM with a very specific question…. I answer all the time (jasoncalacanis on AIM or Skype).
  9. My mouth pain is gone. I’m off the pain killers.
  10. I feel so bad for the folks who died in 9/11 and I wonder sometimes if I’m ever going to get over it. I was watching some 9/11 coverage on Tuesday night about firefighters and I cried. I come from a family of firefighters (my grandfather and my brother) and cops (my uncle, my cousin, and my brother before he became a firefighter). Six years later I’m still crushed by it. I wonder selfishly if I’ll still be crushed by it 10 or 20 years from now. I think fairly confident I suffered PTSD after 9/11 and never really took the time to deal with it.
  11. I feel really great about losing 25-30 pounds over the past year. My energy level is higher, I feel stronger, and I don’t feel like its impossible to lose the weight like I used to. In another life I think I could write about it…. it’s a mindset thing. 100% lifestyle and mindset from what I’ve experienced, and from what I’ve learned from fellow Fatbloggers.com (TM).
  12. I’m thinking I’m only going to blog about things I’m happy about for a month or two. I’m getting tired of the negativity of the blogosphere. I know negative energy can create positive change and all that, but I have to say that “the conversation” has shifted to the point at which “if it bleeds it’s a blog.” I understand why it happens… you don’t blog, you see something that pisses you off and your blog is the first place you turn. Everyone starts doing it and, like the 11 o’clock news, you start to think that the only thing happening in the world is murder. I find folks are, on a percentage basis, less negative in their real-world interactions.
  13. I’m really enjoying my “job” and the work we’re doing at Mahalo. We’ve got an amazing team and we’re figuring out so much stuff every day. We’re making progress so quickly…. I feel that same “this is gonna work” energy I had at Weblogs, Inc. and at Silicon Alley Reporter (a feeling I didn’t have at AOL truth be told).
  14. I put the word “job” in quotes because it just doesn’t feel like one. Sure, we’re doing hard work, but it feels more like a mission…. and that’s what Weblogs, Inc. and SAR were. Gosh I’ve got a great life… I’m so lucky.

Peace out everyone…. I’m off to the CEO dinner. Have to say hooking up with Sequoia has been great. First rate team that takes the time to host dinners to help CEOs solve their problems by sharing and learning together. So frackin’ cool.

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