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



about this episode


Click here to stream the audio version of this episode.
Click here to stream the video version of this episode.

Join our new mailing list and be the first to learn about upcoming guests!

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!

Support This Week in Startups and independent media by joining the TWiST Producer Program at TwistList.co!

Multilingual? Translate this episode of TWiST into another language and email the transcript to translate@thisweekin.com

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

Keep up with the latest from our sister company LAUNCH:

Special thanks to the members of the TWiST Backchannel Program!

Executive Producers


Associate Producers

  • Brad Pineau
  • Kat Ganesan
  • Nicholas Christian
  • Mau Frontier
  • Kyle Braatz
  • Serena Ehrlich
  • Nathan Hangen
  • Lauri Hahne
  • JD
  • Trudy Baidoo
  • Ian Gerstel
  • Julian Hearn
  • Alex Lotoczko
  • James Kennedy
  • Benoit Curdy
  • Asher Nevins
  • Mike Kaltschnee
  • Paul Higgins
  • William Doom
  • David Lee
  • Jake Kerber
  • Sarp Coskun
  • Giuseppe Taibi
  • Tyrone Rubin
  • Keno Vigil
  • Paul Peters
  • Jamal Waring
  • Nick Ostroff
  • Alex Binkley
  • Tom Altman
  • John MP Knox
  • Zon Petilla
  • Bryan McCormick
  • Marcos Trinidad
  • Allen Cordrey
  • Daniel Mich
  • Joshua Rosen
  • Grant Carlile


  • Ryan Hoover
  • Michael Cranston
  • Josiah Thomas
  • João Fernandes
  • Petrus Theron
  • Michael Wild
  • Adrian Grant
  • Dale Emmons
  • Kieran McGrady
  • Tim de Jardine
  • Alejandro Vasquez
  • C. Dain Miller
  • Joshua Opatz
  • Milan Babuskov
  • Chris Rowe
  • Nelson Melo
  • James Dawson
  • Toddy Mladenov
  • Daniel Torres
  • Chris Macke
  • Piotr Zuralski
  • Armand Konan
  • Brian Vogel
  • Paul D
  • Jennifer Sun
  • David Kolb
  • George Gecewicz
  • Sue Marrone
  • Eugene Granovksy
  • Matt Caporella
  • Will Blackton
  • Ryan Dodds
  • Brett Arp
  • Jason Cresswell
  • Edwin Orange
  • Daniel Bradley
  • Shawn Daniel
  • Priidu Kull
  • Marc Kohlbrugge
  • Patrick Desroches
  • Alex Lam
  • Dario Dulic
  • Paul Secor
  • Ryan Urabe
  • Madhu R.
  • Paul Ardeleanu
  • Ian Thomas


  • Carmen Harvey


  • Juston Brommel
  • Michael Gnanakone
  • Gary Stetler
  • Chris Weitzel
  • Kyle Taylor
  • Michael Puhala
  • Joshua Randal
  • Alexander Hektor
  • Christopher Klingler
  • Rob Morgan
  • Nehemiah Wyant
  • Will Mason
  • Bobby Rivera
  • Severan Johnson
  • Abhishek Pillai
  • Kevin Donovan
  • Shiv Rajendran
  • James Parkin
  • Brice C.
  • Dan Ruswick
  • Climate Amante De La Vida
  • William Porter
  • Streaky Gee
  • Andrew Johnson
  • Michael Belanger
  • Andrew Girvan
  • Brian Ruhe


more episodes