E191: Jake Winebaum of Brighter.com on This Week in Startups

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With the rising cost of healthcare, it’s easy to assume that something like dental services are out of your reach. For the 50% of Americans without coverage, Jake Winebaum of Brighter.com has some good news for you: dental care doesn’t have to be prohibitively expensive. Join Jake as he talks about the new wave of health startups and why that’s good news for us all.

0:00-1:00 Welcome everyone to This Week in Startups!
1:00-3:30 Today we have Brighter.com CEO and founder Jake Winebaum.
3:30-5:00 Thank you to GoToMeeting for sponsoring the show.
5:00-5:45 Welcome, Jake.
5:45-6:30 Jake, you’ve had a long history of starting up. What was your first?
6:30-7:30 Why did you start that, of all businesses?
7:30-9:00 And you started a magazine after that?
9:00-9:45 When you sold your magazine to Disney, was that life-changing?
9:45-11:45 What was Eisner like?
11:45-14:30 Is the Go.com portal still in existence?
14:30-16:30 Tell us about your new startup, Brighter.com.
16:30-19:15 Are prices the same across the country?
19:15-20:15 So your business is just trying to get one million people to sign up for this?
20:15-21:45 How is this different from ZocDoc?
21:45-23:45 Do some dentists love you and some hate you?
23:45-26:30 So what happens if I’ve been going to a dentist and then I find them on your list and want to pay that price?
26:30-28:45 Question from the Chill chat: How did Jake validate this opportunity and research the market? What was his due diligence process?
28:45-30:00 Is there an iteration where you hire 1000 dentists and have Brighter.com store fronts?
30:00-32:00 Thank you to Hiscox for sponsoring the show. They just opened a new contest–tell your startup story on their Facebook page (facebook.com/hiscoxsmallbiz) for the chance to win $10k for your business!
32:00-33:15 We’re introducing a new segment called Chart of the Week! This week, we’re looking at a chart from AllThingsD that shows time spent online per month on Facebook, Google, Yahoo, Microsoft and AOL sites.
33:15-35:30 What do you think, Jake? Should Google be worried about this?
35:30-36:45 You’re qualified to be the CEO of Yahoo. Have you ever been offered that job?
36:45-38:45 What’s the secret to your success and strong track record?
38:45-42:30 Who were some of the writers and producers you were working with at Disney to develop their online content?
42:30-43:45 So did you invest when these companies were already at a high valuation?
43:45-44:30 What is it about a guy like Sky Dayton that makes him so special?
44:30-45:30 Question from the chat: Are there any plans to expand overseas?
45:30-46:15 What did you pay for Brighter.com?
46:15-47:45 Question from the chat: What other spaces does Jake think are in need of disruption?
47:45-50:30 How do you deal with negative reviews of dentists?
50:30-55:30 We’re introducing a new segment: guess the fake startup. Kirin, who do we have to choose from today?
55:30-56:00 Jake: Do you dress your dogs up, Jason?
56:00-57:00 The big reveal: HauteDog.com is fake!
57:00-01:00:00 Jake, you don’t need to work anymore, so what keeps you going?
01:00:00-01:01:30 How do you stay competitive with 23 year olds working 90 hours a week who are web natives?
01:01:30-01:03:00 What’s the hardest, most brutal lesson you’ve learned in business?
01:03:00-01:03:45 How much do you think the average entrepreneur is afraid of failure?
01:03:45-01:04:30 If you’re a brilliant developer email jake@brighter.com.
01:04:30-01:05:00 Next up is This Week in Web Design with host Jose Caballer, so stick around!
01:05:00-01:05:30 Thank you to Hiscox and GoToMeeting and thank you Jake!

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Jason: @jason
Tyler: @steepdecline
Brighter: @brighter
Kirin: @kirinkalia

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