In this week’s meeting, Alex Knight returns to share his penchant for dissecting cartoons and how he has to constantly defend comic books and video games against the notion that the medium is just for children's entertainment.In addition, we

64: The Guilty Whiner

Jun 14th, 2015 47m 31s

In this week’s meeting, Nate Boateng confronts his guilt over whining about inconsequential things and how he gets unreasonably annoyed at software bugs, poor user interface design, slow app updated for new iOS versions, and generally having hi

63: The Angry Dad Gamer

Jun 7th, 2015 48m 1s

In this week’s meeting, Victor Agreda Jr. returns to tackle step four by confronting his anger management issues towards poor video game design and how he manages to stream video games nearly every day from his living room.In addition, we dis

62: The Poor Scheduler

May 31st, 2015 41m 19s

In this week’s meeting, John Moltz confronts his recurring issues with scheduling things on his calendar, his problem with the social conventions of confirming plans, and differentiating between to-dos, reminders and events.In addition, we di

61: The Savvy YouTuber

May 24th, 2015 39m 33s

In this week’s meeting, Amy Schmittauer of Savvy Sexy Social confronts step six by sharing how she maintains her personal brand on YouTube, overly embraces the commenters on her videos, and her addiction to jump cuts.In addition, we discuss Y

60: The eBay Buff

May 17th, 2015 57m 39s

In this week’s meeting, Andy Mangold of 5by5's On The Grid tackles step ten by sharing how he does almost all of his shopping on eBay, the advanced search techniques utilized, how he prefers used items over new, and that eBay is much underrated

59: The Smartphone Swinger

May 10th, 2015 44m 31s

In this week’s meeting, Todd Wright shares how he manages to use three different smartphones regularly, going back and forth between ecosystems, dealing with his anger management issues towards mobile operating systems, and his frustration in c

58: The High Fidelity Hoarder

May 3rd, 2015 45m 17s

In this week’s meeting, Kirk McElhearn completes step four by objectively reconciling his management of a 75,000+ track music library, his endless frustration with iTunes Match, and admitting that at his age, he has a natural predilection towar

57: The Soothsayer

Apr 26th, 2015 1h

In this week’s meeting, Abdel Ibrahim of The Tech Block shares his obsessive fascination with the smartwatch as a product category, why he enjoys looking at new products based on where they may take us in the future, and how he's frustrated tha

56: The Paradise Project Manager

Apr 19th, 2015 46m 59s

In this week’s meeting, Jerome Koehler confronts step five by sharing how he learned to not get passive aggressive over technical support questions, dealing with luddite bureaucrats as a project manager, and how he takes the scenery, climate an

55: The Cheapskate Dater

Apr 12th, 2015 55m 28s

In this week’s meeting, Curtis Silver shares his experience with online dating as a recently single man with social anxiety, why he won't pay a dime for any of the online dating sites or apps, how he filters profiles to find potential matches,

54: The Subscribaholic

Apr 5th, 2015 52m 58s

In this week’s meeting, Ryan Sullivan of WP Site Care confesses his dependency on Amazon, that he makes nearly all of his household and grocery purchases online, and how he's concerned that his mailman and neighbors are secretly judging him by

53: The Stream Fiend

Mar 29th, 2015 48m 58s

In this week’s meeting, Joe Caiati of Diagnostics & Usage confesses his addiction to the new mobile live-streaming apps Meerkat & Periscope, how it feeds his desperate grasp for attention, why he can't stop himself from signing up to every new

52: The Perpetual Contrarian

Mar 22nd, 2015 52m 23s

In this week’s meeting, Brian S. Hall tackles step six by sharing how he gets pegged a "hater" on Twitter for criticizing tech writers, his condemnation of business models that lead to poor journalism, and that he worries his constant contraria

51: The Overprivileged Parent

Mar 15th, 2015 55m 7s

In this week’s meeting, John Sextro of 5by5's iOhYes works through step five by admitting he spoils his four children with the latest and greatest gadgets & devices, the perils of raising kids in this hyper-connected technological age, and the

50: The Parody Account Creator

Mar 8th, 2015 45m 36s

In this week’s meeting, Kyle Seth Gray shares his addiction to creating parody accounts on Twitter, how he get bored with them very quickly even though he's on Twitter nearly all the time, how he's "too cool" for old news and the many ways he's

49: The Mac Convert

Mar 1st, 2015 54m 52s

In this week’s meeting, Vic Hudson shares his experience making the transition from PC to Mac, how he's battle-hardened from having to fix and maintain his Windows machine all the time, coming to terms with non-user upgradeable computers, and h

48: The Free Access Educator

Feb 22nd, 2015 52m 22s

In this week’s meeting, Bradley Chambers of Out Of School works through step eleven by describing the day-to-day struggles he has as the I.T. director of an educational institution, why he leans more towards allowing students free access to inf

47: The Battered Apple Writer

Feb 15th, 2015 52m 23s

In this week’s meeting, Jim Dalrymple of The Loop and 5by5's Amplified attempts to tackle step eight by confronting the trauma of covering Apple when the company was beleaguered in the 90's, how it fuels his ongoing vengeance towards Blackberry

46: The Launch Addict

Feb 8th, 2015 57m 54s

In this week’s meeting, Justin Jackson of Build & Launch works through step five by confessing to his obsession with starting new side projects, that he rarely informs his wife about these new endeavors, how he feels old for the startup world,

45: The Privileged Consumer

Feb 1st, 2015 1h 26m

In this week’s meeting, Dan Benjamin of 5by5 works through step five by sharing his high expectations in being able to watch content whenever & wherever he wants, how he has the luxury to pay to remove annoyances with media consumption, why it

44: The Podcast Jackal

Jan 25th, 2015 41m 40s

In this week’s meeting, Mike Beasterfeld of Better Know A Jackal shares his narcissistic motivations in listening to live podcasts, handling the asynchronous relationship he has with podcast hosts, and how he's afraid of evangelizing technology

43: The Workflow Whisperer

Jan 18th, 2015 1h 3m

In this week’s meeting, Alex Guyot admits to his constant fiddling with iOS automation and URL schemes, his obsession with "every tap counts" type of peak efficiency, why it's painful for him to watch friends use their phones, and how he strugg

42: The Functional Designer

Jan 11th, 2015 1h 9m

In this week’s meeting, Joe Darnell shares his obsession with manipulating images in Photoshop, how he tends to live like his life is the subject of an art magazine, why his motivation in "making the world a better place" is an outright narciss

41: The Homescreen King

Jan 4th, 2015 1h 3m

In this week’s meeting, Ronnie Lutes works through step two by sharing his obsession of meticulously arranging his iPhone homescreen apps, how his eyes bleed when seeing homescreens that aren't color coordinated and how he overthinks the decisi