A Walk Down Memory Lane: My Third Ever Podcast… with Michael Arrington

Photo courtesy Robert Scoble
Photo courtesy Robert Scoble

One of the lessons I learned early on in life was the power of networking. When I worked at Fidelity Investments between 1997 – 2006, this was relatively easy to do because there were a lot of people on both the brand, agency and startup side that wanted to work with one of the largest and most innovative companies in the world. When I left Fidelity to become the CMO of a startup called SharedInsights (eventually, this became Mzinga), I realized pretty quickly that I needed to change my tactics as nobody knew who SharedInsights was. Thanks to my friend, Francois Gossieaux, I learned that one of the easiest ways to create a connection with someone you wanted to know was to ask them if they would do an interview with you.

My first official podcast interview was with Shel Israel at the Office 2.0 Conference in San Francisco in September of 2007. Next up was (now) good friend, Mukund Mohan. Both were relatively easy as they were friendly, approachable and I had spent some time with them in person. My third interview which was in November of 2007 with none other than TechCrunch CEO and Founder, Michael Arrington. To be honest, I was way out of my league on this one but I was lucky enough to meet Mike at a TechCrunch event we were sponsoring in Boston and never being one to lack for balls, I walked right up to him, introduced myself and asked if I could interview him.

In retrospect, the interview ended up being pretty decent in spite of me being nervous as shit. The funniest part of the interview was that Arrington could sense this and gave me a little up front pep talk and encouraged me to relax.

The reason I started thinking about this interview was because the other day, Chris Brogan, wrote a Facebook post about good podcast etiquette (and the best way to conduct one with him). The conversation reminded me of my early days of podcasting and after digging around a bit, I was able to locate the transcript and audio file (this is still property of Mzinga even though they have taken it down so I am linking to their site and giving full attribution rights to them).

Three take aways from this:

  • Interesting history lesson as Arrington and I talk about Twitter, GoogleDocs and the importance of blogging.
  • Since that interview, I have yet to be as nervous as I was on that call. And that includes a recent interview with Al Roker of the Today Show.
  • While I love doing the Live from Stubbs video show with Kyle Flaherty and Greg Matthews, Kyle and I have been talking with our former co-host of the Quick’n’Dirty podcast, Jennifer Leggio about getting the band back together. Stay tuned on this one.

Below is a slightly cleaned up transcript of my interview with Michael Arrington and here is a link to the original podcast. His comment about the podcast when he first posted it on CrunchNotes was pretty funny as well.

Aaron Strout: 

So, some quick questions. We’ll dive right in here. You have an interesting background. I was checking you out on TechCrunch today. You started off as a corporate attorney working in Silicon Valley. You now run a business called Edgeio. You consult on the side. And then you run TechCrunch as a hobby, at least according to what you put up there.

So, how did you go from lawyer to serial entrepreneur and über blogger?

Michael Arrington:    

Über blogger. What’s that mean?

Aaron Strout: 

That’s my new term. Well, you know, one of those guys that sits above the rest of us.

Michael Arrington:    

Hmm. Well, we should talk about that separately but I –

Aaron Strout: 

I mean that as a positive thing.

Michael Arrington:    

No, no. I know you do but I’m not sure I agree, even though you meant it as a compliment. Or it clearly is a compliment. I just have certain thoughts on the community and how we all work together and we’re all very reliant on each other.

But I was a lawyer. I came out of law school in Silicon Valley and right when Internet was going commercial. And I didn’t go to a tech firm. I went to a law firm called O’Melveny & Myers. It’s in San Francisco, and for a year, Netscape was – their software was out. I think they’d gone public and everybody was going crazy over the Internet. I was helping Ford sell a subsidiary that leased airplanes to other companies, so it was incredibly boring. I spent a year in a room with no windows reviewing aircraft leases, and a lot of my classmates were having a lot of fun doing tech work.

So, I looked to change law firms and after my first year, I moved to a firm called Wilson Sonsini in Palo Alto, which is the first tech firm, the largest tech firm. Had taken Apple public and taken Netscape public and it was just sort of the place to be if you were a lawyer and wanted to do tech work.

I also got pretty lucky. I went into a group that did a lot of IPO work, a lot of venture capital work and I got on the Netscape team itself, so all the Netscape acquisitions after ’96 – there were probably two a year – I worked on directly. So, it was a lot of fun.

We also – our group also had a relationship with Steve Jobs and represented both Pixar and NeXT Software, and so we did a Pixar deal. Those were always fun. But when NeXT was sold to Apple and Steve returned to Apple, I worked on that deal, kept it working with Steve Jobs a little bit. Met him twice during the course of that deal. One time I met him I was so nervous I spilt a cup of coffee that I held in my hand all over myself. It was kind of funny.

Aaron Strout: 

A real joy.

Michael Arrington:    

Yeah. And then he once left me a voice mail – back then e-mail obviously was around but we still did a lot of business by voice mail. And he left me a voice mail once asking me to do some things, and I saved that voice mail. There was a way in the system you could – every two weeks it prompted you to delete it but you could keep saving it. I saved it for the entire time I was at Wilson Sonsini and listened to it every once in a while. So, it was kind of cool.

But eventually too many of my clients were getting way too rich, and I also felt like not only were they making all the money while we did a lot of the work, but I also felt like we were kind of outsiders, so – these big deals would get done, but it was sort of after the hands were shaken that they would come to us and say, “OK, pay for this and close it.” And it felt like, well, “Sure.” We played an important part of the deal, but we weren’t out there hunting. We were just sort of butchering the animal once it was caught.

So I decided to leave and joined the hottest startup that I represented at the time, which was called RealNames. It raised over $100 million. I joined as head of biz dev and head of sales, and things kind of went from there. Since then, I’ve been an entrepreneur.

I worked there for about a year. The company filed to go public. I had largely vested in my stock, so I left and started my own company, which was boring. It was in the payment space, but we sold it really quickly. We sold it. In about 13 months from founding it, we sold it to First Data Corporation and it is now part of Western Union’s back end. So, that technology at least lives on, although the brand Achex doesn’t.

And then I took some years and consulted and messed around in Europe. Lived in Copenhagen and London. Lived in [inaudible] for a year. Just did nothing but surf and watch movies, work out. That was a good year.

And then finally, I sort of got sucked back into the tech scene, because my long-time mentor Keith Teare wanted to start a new company which is called Edgeio. And he sucked me back in as a co-founder and the original CEO, and I was a little bit behind the times on what was going on on the net. And so, I started reading blogs for the first time. Before that I’d only ever read Dave Winer’s blog, Scripting News.

But I started reading a lot of blogs, trying to get an understanding of what the new startups were doing. And I realized there was no one place to read about startups and there were no dedicated blogs for startups, so I was reading hundreds of blogs trying to get a feel for what was coming. So that’s when in the middle of 2005, I decided to just start my own startup-dedicated blog.

Aaron Strout: 

So, I heard an anecdote to that. I think it was around Robert Scoble that at one point you were asked, Did you know who Robert Scoble was? And you didn’t know, and then it turned out that you read his blog and found him very interesting, and since then he’s been someone that you read fairly regularly. Is that a fair statement?

Michael Arrington:    

I don’t think I’ve ever been asked, “Do you know who Robert Scoble is?” and I’ve said no.

Aaron Strout: 

It may be blogosphere myth then.

Michael Arrington:    

It might be. But he was one of the first big blogs to link to TechCrunch, so I think he wrote something like, “Hey, I haven’t noticed TechCrunch before. There’s some good blogging going on over there.” This is in like maybe two months or a month after we launched. And so it was like a big day. I had a TechCrunch T-shirt made up and sent it to him. I was pretty excited. It’s the first time any real traffic went to the site.

So, I’ve been a big friend and supporter of his for quite a while, and then in 2006, he got me invited to MIX 06, Microsoft’s annual developer conference, and as a surprise organized a lunch between me and Bill Gates. And so I got to meet Bill Gates and shook his hand. There are a couple of pictures taken that are floating around in the web and again, that was all him. So, I owe him a lot. I’ve always been good friends with him.

Aaron Strout: 

Well, he’s a good person to know. But I guess to that end, you started off the conversation this way: About the über bloggers. I’d love to get your thoughts on that, and I guess my thinking is – and I think you took it as such that there are a group of what are called the “A-tier bloggers,” or the influencers in the space, and then there are a lot of other folks that are writing great content but are not as well recognized. But I do certainly agree with you that it is a community, and one of the things I’m learning on Twitter, which I’ve been on for a few months now, is how much collaboration goes on and how much you really can learn from anyone, whether they’re new or whether they’ve been doing it for a while. So maybe you could give me a little more thought on your reaction to the term über blogger.

Michael Arrington:    

Well, so first of all, popular bloggers sometimes become popular very, very quickly. Say Steve Jobs’s guys, for example, that I consider more of a stunt than anything. Silicon Valley Insider, a blog based in New York, hasn’t been around that long and yet there’s sort of a must-read now just because they break a lot of news.

AllThingsD with Kara Swisher has come on the scene and yeah, she’s been around forever, but AllThingsD has become a real high-quality site. And these are sort of the blogs in my universe. I’m sure there are countless examples of other topical blogs that I don’t even know about that have done the same.

And so, one, is it doesn’t necessarily take years and years to build a blog up, and I certainly think that even somebody that’s not blogging now could be what you would call and A-lister in a year from now if they chose their topic wisely, cared about what they wrote, about and were diligent about it. But it also means that because new blogs can rise very, very quickly, it means that blogs that are in some kind of entrenched position – and I think we’re one of them now – constantly have to be worried about competition and being creative and trying new things and keeping the content fresh.

The funny thing is that I’ve seen blogs that got fairly big start to worry about competition, and their reaction was to hunker down, close themselves off, never link to anyone, particularly the one that they felt was competitive to them. And if anything, it hurt them. It made them shrink. It made people feel they were less relevant.

So, I think the only way to stay big and grow is to constantly embrace the community and to constantly read what they have to write, think about it, write about it if it makes sense with your own thoughts as well. But make sure that when they write something really, really good, that you call it out and you link to them. And you say, “Wow, that was really good.” Just like Robert Scoble did for me.

And you never know. If those guys continue to write good stuff, other people are going to call it out. And someday they might be bigger than you, and you’ll be glad that you linked to them. And so that’s the important thing.

And I think that we’ve been pretty good about doing that. One thing we’re doing this January is an award ceremony for new startups that I reached out to what most people would call our biggest competitors, such as ReadWriteWeb which is Richard MacManus’ team; Matt Marshall of Venture Beat; and others and said, “Hey, let’s all get together, share the economics, share the upside and downside and put on an award ceremony for startups. It’s really just about the startups. Not about us making money or getting attention.”

And everyone agreed. It was fairly easy to get everyone to agree to it, and we’re doing it. And we’re going to have a really cool event in January with all these blogs working together. Now, I can’t imagine ever seeing Business Week, Newsweek, The Wall Street Journal, The New York Times getting together to do something similar. It just wouldn’t happen.

And so that’s why I think I sort of chafe at the term über blogger, A-lister, because we are part of a community. We are nodes within a community and what really matters is the community and how big it is and the quality of content coming out of it.

Aaron Strout: 

Yeah, no. I totally agree, and that is a good point. And I think it’s particularly interesting you drawing the line between the old-world and new-world media, which is happening a lot, I think, in businesses in general, in how communities are being formed and companies that get it and companies that don’t.

A couple of examples, I think, like Wal-Mart, who gets bashed regularly. Even though they’re not that – well, I guess they are an old business, but they’ve come on the scene and become popular in the last 10 years, and they can’t seem to do anything right in the social media space, even though they try. And then you have someone like Target, who is doing things not all that differently, although they certainly haven’t been accused of sort of fake blogs or things like that, or I guess what’s – “astroturfing” is the term.

But I guess to that end, you get to talk to a lot of people and you get to read and sort of pay attention to a lot of the different trends that are going on. Who do you – what do you see as a couple of the sort of hottest – and not just hottest, because I think not things that are hot for hot’s sake, but hottest technologies or providers or apps that are out there that a business really could apply right now that –

Whether it’s Twitter, whether it’s OpenSocial, whether it’s I-don’t-know-what-the-other-thing-is, but what are you paying attention to right now that the listeners could really benefit from in terms of something that they should be thinking about for their business?

Michael Arrington:    

Well, it really depends on what specifically the goals of the company are. If it’s office efficiency, I don’t have a whole lot to say. I mean, I think instant messaging and IM’ing and all those things are pretty important for companies to embrace to keep their office efficient and tapped into what’s going on.

And there’s lots of new technologies that come out all the time. Although for a company to sort of test them all, I think, would be crazy, I think they should wait six, eight months, a year and see what sticks and then adopt stuff in that space.

An example is Google Docs. I mean, does it make sense for a small company to stop purchasing Office for their employees and use Google Docs instead? Well, I think it is. I mean we certainly do that here. We use Google Docs constantly now because of the collaboration benefits, but we don’t get very deep in either the Excel or the Word functionality, so it works for us. It may not work for other companies that have, you know, maybe need deeper functionality or more data security than we do.

But I think what you’re asking is, “How do companies engage with the social net and in ways that help them from a marketing perspective in gaining users and user trust?” And to that end, I think Twitter is an excellent way of – if you can get even a small following of dedicated users to follow you on Twitter, I think that’s great. I think what’s even better is if you make sure that whoever’s running that for you internally is also going to your users’ Twitter accounts and reading what they have to say and commenting on it appropriately.

If you don’t have a blog – and it’s amazing how many even web startups don’t have blogs – you’re absolutely crazy at this point. I’d say a good 30, 40 percent of startups we see do not have a blog. You need a blog. You need a main domain name. And you need to link to people who have written about you, whether it’s positive or negative. And talk about what they’ve written, and that will give an incentive for more people to write about you.

And again, not just the positive stuff. Any time somebody talks, unless somebody is circuitously trashing you. You don’t want to link to it, but if they bring up some good points, I think linking to them and discussing those points and how you deal with them shows a level of maturity that people will respect and you’ll get far more links that way, which is really what you’re after.

So Twitter, blogging, I think, are important. Doing video demos of your products, particularly if it’s not just super intuitive, is a really good idea. And just putting those up on YouTube is great, and then other people can embed those in their blogs and things like that.

Beyond that, I don’t know if you need to embrace every new startup that comes out. Again, I think you can wait and see what sticks. A year ago, I wouldn’t have said it was important for companies to be out there Twittering, but certainly today I think it is.

Aaron Strout: 

So, if I’m recapping correctly, it’s not necessarily always the sexy, hottest thing. I mean Twitter obviously is a little bit of a darling right now in the new media world, but you talked about things like Google Docs, which really mimics functionality that’s been around for, I don’t know, 10, 15, 20 years. Blogs certainly have been around for five or six years now, and video has been around for a while, so it’s really the practical things that keep coming up that are great for information sharing – basically collaborating, getting work done – are some of the applications that you see as being most beneficial?

Michael Arrington:    

Hmm. If you think about a few years ago and most communication with people was done via the press release, which was drafted by the CEO or some senior exec and then filtered by the PR people, who, felt their job basically consisted of protecting the company by not giving away too much information or de-humanizing text, and then brought back to the CEO for another run-through. And I’ve been in companies where these things go through five, six, seven, 10 redrafts. And then you finally release this press release, which absolutely no one cares about, no one picks up. And the only place it’s found is on your own website, if you post it. And then, of course, if you run it through a wire service, it will appear on like Google Business or Yahoo Business. And then I remember people going, “Hey, look: It’s on Yahoo.” And that’s just dead.

I like startups that never issue press releases. Once you’re public, different rules apply, but when you’re private, who cares if you screw up occasionally? Who cares if you accidentally say something you shouldn’t have said?

The point is, it’s a human voice and it’s a raw voice and it’s unedited by 10 people filtering it. And I think that’s a lot more important. So if you don’t blog, you need to get one. And if you think that you have a reason why you don’t need one, you’re wrong. You need to get one.

Aaron Strout: 

Well, I love hearing that from you, because we are big believers in that. We build communities for some of our clients and certainly one of the manifestations of our communities is that WeAreSmarter project. And so, we’re big advocates of having a voice and particularly a human voice, and I put myself out there regularly. And I do a personal blog and a work blog, and it’s the concept of “naked conversations.” And I think people appreciate that, and there’s a lot of value to it. And it’s a scary thing, because as you mentioned earlier, the old world versus new world in the media space.

And I think a lot of people are still grappling with that idea of, “How do I do this, and how can I do this, and what if my competitors read what I’m thinking about?” And it’s like, well, they already know what you’re thinking about. So, you’re just making a hero out of yourself for your customers, and at least letting them know what you’re thinking about and letting them collaborate with you, I think.

Michael Arrington:    

I agree. What did you think of the party we had last – two weeks ago now?

Aaron Strout: 

It was great. Yeah. So for those listening in, that’s part of how I bumped into Michael and grabbed his hand and introduced myself. We were at the TechCrunch meetup, so I thought it was a great way to introduce ourselves into the marketplace. There was a lot of energy there.

I liked the fact that IDG had some expletives for Silicon Valley, whether it was right or wrong, but it showed some enthusiasm and some East Coast pride. And I know – I watched a video that PerkettPR did that talked about really kind of creating an energy on the East Coast that we need out here, and so the party was great. A lot of smart people there, and fun to see some of the other products that the people are launching. I didn’t get as much time to walk around and do that as I liked, but we really enjoyed ourselves.

Michael Arrington:    

Good. Our hope is to do it again next year. So, you going to make your way out here in the next year?

Aaron Strout: 

I’m sold on the idea of coming to those, because I think they’re great networking events and great ways to see other products and get a pulse on the market. So, absolutely. And I’ll definitely be there for next year’s event. We’ll be happy to promote it, too.

Michael Arrington:    

All right, Aaron. Well thanks very much for having me on.

Aaron Strout: 

Mike, I really appreciate it and thanks again for your time.

45 Things I’ve Learned in My 45 Years on Earth

The other night, I was flying back from the west coast and found myself on a flight without wifi and in a rare situation where I was fairly caught up on e-mail/work. Instead of sleeping or reading my latest issue of Rolling Stone, I got thinking about how lucky I was 45 years into my life and all of the things that I had learned along the way. I was skeptical at first that I could come up with 45 lessons (to match my age) but low and behold once I started writing they managed to flow.


Many of you that know me have already seen this on Facebook (apparently it struck a nerve as I received over 200 likes and north of 85 comments as of the writing of this post). But given the ephemeral nature of Facebook and the fact that I would like to be able to hold onto these little “Stroutisms” as someone called them, I am pasting them over here on my now-seldom-used blog for safe keeping.

I amy also add to these over time in the comments. Feel free to do the same if you are so inclined:

Sitting on a plane with no wifi and thinking about some of the things I’ve learned over the course of my 45 years on this planet. Here are 45 things in no particular order:

  1. Raising children is the hardest job you will ever have.
  2. Raising children is the most rewarding job you will ever have.
  3. Being in love is an amazing feeling.
  4. Being in love with the same woman for 20 years is an even more amazing feeling.
  5. One of the keys to keeping a marriage alive is good communication.
  6. Another key to keeping a marriage alive is being willing to meet your spouse halfway. On everything.
  7. Dusk is my favorite time of the day.
  8. The ocean is one of the most remarkable things on this planet. If you live near it, never take it for granted.
  9. Everything in moderation… including moderation.
  10. I was incredibly lucky to grow up with two wonderful parents and four equally wonderful grandparents.
  11. No matter how many times I fly on a plane, I am amazed that something that big/heavy can fly.
  12. Nothing quite as good as tomatoes fresh out of the garden.
  13. Anything that is good in life is worth working for.
  14. If you don’t love your job, quit. Seriously.
  15. I have been lucky to always work at places where I have enjoyed and respected my colleagues.
  16. A good night sleep is underrated.
  17. Never stop learning.
  18. Never stop listening to new music. Ask your friends, kids, neighbors and colleagues for recommendations.
  19. I am still pissed that Jimi Hendrix, Kurt Cobain and Layne Staley died too early.
  20. Few things beat sitting on the patio/porch/deck in the morning with a cup of coffee.
  21. Okay, sitting on the patio/porch/deck in the early evening with a cool drink might beat a cup of coffee in the morning.
  22. There is something magical about a bonfire or a fire in the fireplace for that matter.
  23. Bacon should be its own food group. True story, I didn’t eat bacon for 20 years. I am now making up for lost time.
  24. It’s important to provide guidelines and discipline and firm boundaries for your children.
  25. It’s equally important to transgress guidelines and boundaries with your kids once in a while.
  26. If you have something to do, get it done first. Procrastinating just makes the time in between the present and what you have to do miserable.
  27. Writing a book is hard.
  28. Writing a blog consistently is hard.
  29. Running 3-4 times a week is hard.
  30. Writing a book is one of the most amazing things you will ever do.
  31. Writing a blog consistently is cathartic.
  32. Running 3-4 times a week feels good. And is good for you.
  33. Don’t ever take yourself too seriously.
  34. Compliment at least one person every day.
  35. Seeing a baseball game at Fenway Park at least once in a lifetime should be everyone’s bucket list.
  36. Having a soul mate makes life immeasurably easier.
  37. Tell your children you love them at least once a day – even when you are mad at them. Same with your significant other.
  38. There is a reason God gave us two ears and one mouth. I am still working on listening more and talking less.
  39. Given a choice, I will choose plain cheese pizza over those with toppings.
  40. There are few things tastier than vanilla ice cream topped with hot fudge.
  41. People are inherently good.
  42. There are no such things as absolutes in politics but rather shades of gray.
  43. Be comfortable in your own skin.
  44. The older I get, the less I realize I know.
  45. I love being 45.


Austin Breakfast Places FTW

The other day, our family decided we wanted to break out of our normal habits of eating breakfast at Magnolia and Torchy’s so I asked my Austin friends where they suggested we should try next. The original thread on Facebook is here.

In the spirit of sharing, I have created a blog post with each of the restaurants suggested, a link to the Yelp review (and menu where available). I’ve also included any notes provided by the recommender like “great brunch place” or  “good for “Bloody Marys.” If you have others you want to add in the comments, go for it. If you leave the link to the Yelp review and menu, I will go back and include them in the original list. Here goes: