E049: with Sky Dayton



about this episode

Jason’s guest this week was Sky Dayton, Founder of Earthlink, co-founder of eCompanies, Founder and Chairman of Boingo

00:00:20  Next weeks show will be the big 50th show celebration in San Francisco held at a secret location, with a secret guest.  If you’d like to sign up for tickets (limited seating) please fill out this form (April 30th, doors open at 6pm, show starts at 7pm, PST)

00:02:00  Intro Sky Dayton, Founder of Earthlink, eCompanies, Boingo

00:03:30  Ask Jason – Craig Tataryn congrats on being a father

00:04:30  Craig writes for FunctionalFather and has written about sleep deprivation

00:05:00  How formal show market research be when considering a startup?

00:05:30  For jason’s past ideas on 10-20% of friends understood is idea, 50% didn’t understand at all, he tends to look early adopter trends

00:06:00  Focus on what inspired you to the idea, what problem are you solving

00:07:00  He uses 0% market research but looks at what ways to position it and how to price

00:08:00  Fast fail

00:08:30  Web based companies should only take about $100-200K to get started and see if the idea will work

00:09:00  OAF, must have a product to apply

00:10:00  The market is your market research

00:10:30  Craig’s idea is an iPhone app for men/husbands to help them decide what to buy for their wife or girlfriend

00:11:30  Think like the consumer

00:12:00  You may want to leverage your wife’s social network to help the idea succeed

00:14:00  Think big act decisively

00:15:00  Think of an app as an extension of a website

00:15:50  Niche is the new mainstream

Provides fully hosted / managed Microsoft Exchange and Google Apps e-mail

00:18:30  catering a box of Cheezits

00:19:20  Shark Tank – Corey StanfordBlazetrak – the first online resource that puts you directly in touch with top professionals in the areas of music, fashion/design, screen/stage, sports, business and many more and get a video response

00:23:00  Jason, pitch was very clear understands pain point 7.5-8

00:23:30  Will have to be careful, this may sound like a scam

00:24:00  Tyler, 8/8 like the music vertical

00:25:00  People do pay consultants

00:25:30  You submit to specific people

00:26:00  For advice ok but for anything artistic in nature isn’t that against the nature process

00:26:50  Celebrity or expert solicited for videos

00:27:30  Idea is being done by folks trying to sell head-shots

00:29:00  You get a video response

00:29:15  Does the pitching person have rights to the video response? both parties have to agree for public use

00:30:15  OAF gives feedback they feel it is their obligation

00:30:40  Integrating charity may work, it is more powerful for celebrities

00:32:30  @BlazeTrak

00:33:00  Corey’s first time watching, partner is a fan

Soon launching WebSpy Soho – Easily monitor Home & Small Network bandwidth usage, Internet connection speed and much more – Test Alpha version
00:33:30  Jason at times would love to do a 3 hour radio show with Tyler and Lon

00:35:00  Interview Segment

00:35:45  Sky has been an entrepreneur since 10 years old, window washing business

00:36:45  Jason at a young age was fascinated about acquiring money

00:37:30  Cafe Mocha (you have to look at the pics in that link), second business, idea was to meet girls, irony is he never met any he was too worried about running the business

00:38:30  They went some tough times, they did flyers to drum up business

00:39:00  It paid off and they got extremely busy and were featured on MTV, Melrose Place

00:39:50  Overnight success over 10 years

00:42:00  Earthlink idea conception, he remembers driving home at midnight, listening to New Order, on the 101

00:42:50  Incredible struggle to get success

00:43:30  Valentines Day 95′ database completely crashed

00:44:30  IN 94′ “internet” did not exist in directories

00:44:45  Fill an unmet need and do it well

00:45:00  Focused on customer service

00:45:15  Brought in a professional CEO

00:45:45  Disney Internet Group

00:47:45  Icebox Cartoon Network

00:48:45  Back then no advertising model

00:49:00  It was a try here (internet) and then bring to TV

00:50:00  JAMDAT sold to EA

00:51:00  Boingo $9.95 a month domestic

00:51:00  Actually costs money to have WiFi removed from your motherboard

00:52:30  Multiple sign-ins is an incredibly fractured model, Boingo solves that and has 130,000 hotspots

00:53:30  They have a lot of partnerships and focus on big airports

00:54:10  Won rights for WiFi in all UK airports

00:56:30  Average data use on mobile device Blackberry 30MB on iPhone 1GB

00:58:10  Rule of thumb if you are outdoors 3G and 4G service if you are indoors WiFi

00:59:00  iPad a game changer

01:00:35  Users will continue to need more bandwidth

01:00:50  WiFi a core function of the internet

01:01:25  Agreements must be very complicated

01:02:10  Helio, a great learning experience

01:03:15  Needed to reach scale and never met that point

01:04:00  In mobile distribution is king

01:04:20  Apple has stores and distribution

01:04:50  Tesla must have a showroom

01:05:20  Great thing about web based businesses is the customers go directly to you

01:05:50  How do you deal with failure?  Sky stayed with it to the end, did sell to Virgin and feels he got to fist base

01:07:40  entrepreneurs don’t have reverse or neutral they only have forward

01:08:20  Will you start a company?  He has ideas, when the time is right he’ll jump in

01:08:55  Amazing time to be an entrepreneur

01:09:20  Competition is fierce for any idea

01:11:40  News with Lon, he broke his foot by slipping off a curb while talking on his iPhone

01:14:00  Facebook Open Graph

01:15:30  Very powerful for SEO

01:16:00  Should be replaced by an open source global system, Apple and Facebook don’t play nice with data

01:17:05  Insights From Tyler – “Feels like shaking hands with Steve Wozniak”

01:17:40  Jason’s story about meeting WOZ, thay had lunch and WOZ was eating a big sandwich and making a mess, licked his fingers and later gave Jason the double hand handshake, Jason has concerns about germs

01:20:10  Jason had to do the double wash

01:22:00  The feature will be a powerful and instant endorsement

01:22:30  Will you lose privacy?

01:23:50  This is a dangerous precedent and their will be lawsuits

01:24:40  Zuckerberg’s position is wrong with regard to privacy

01:25:00  It s innovative and will provide value and it forces privacy issues

01:26:10  Business Insider Transcripts

01:27:20  Success brings attention, you will eventually step on someones toes

01:30:20  Blippy Credit Card Issue

01:31:40  How big of a PR problem is this?  Phil did a good job handling the issue, very serious PR issue but as an actual threat not so much

01:33:30  When you slip up it’s your job to educate

01:34:20  He was transparent

01:34:30  Job Hopping

01:35:25  Is it fair to dismiss an employee based on his resume?  Did not ask Mark to write the post, Jason asks for 3 years when you are hired and he will be very loyal to you

01:37:00  Loyalty is important in life

01:37:30  Jason probably wouldn’t interview based on a job hopping resume

01:37:50  If you only work for one year you look like a flake

01:39:30  Gen Y trophy, Excellence in showing up

01:40:25  Sky would ask why, it may not be hopping and compares it to failing fast if the person wasn’t right for the job

01:42:40  What kind of loyalty should employers show employees?  They should help develop the persona and provide a job

01:44:05  Two of Jason’s former bosses are his best friends

01:44:30  Gratitude Exercise

01:46:30  Background, one of Jason’s employees left for a larger company, he liked the person

01:48:45  Treat employees how you would want to be treated

01:49:30  Foursquare Sale?

01:50:00  Would you sell for over $100M?  very personal decision, no one answer, depends on circumstances

Provides fully managed virtual private server hosting with great customer service and amazing pricing. Receive 25% off for life using the code: twist

01:55:30  Sign-up for tickets for 50th show

01:57:00  End

Ustream is the leader in live video with more than 75 million monthly viewers. The platform empowers any individual, public figure or brand to stream to a global audience of unlimited size. Ustream offers free broadcasting and viewing platforms for theWeb and mobile devices. Follow on Twitter or fan at Facebook.

If I missed anything please include it in the comments and I’ll integrate it into the post.

Click here to vote for this interview on Hacker News

Please rate the show in the comments

more episodes