TYL #1: Building Killer Cultures with Passion and Struggle with Derek Flanzraich

Written by on 19 Feb 2016

Today I have the pleasure of sharing our very first peer interview on Transform Your Life with Tracy Timm!


In this episode, I interview peer entrepreneur and dear friend Derek Flanzraich.


Derek is the CEO and Founder of Greatist.com, a next-generation media company working to build the first truly-trusted, consumer-facing health brand for Millenials. Greatist is currently the fastest-growing media site in the digital health space, with nearly 10 million unique visitors per month.


Derek is a Harvard grad (boo…hiss), a Google-rejector, a serial “starter of things,” and a believer in the incentive of killer culture.


In our conversation, Derek and I discuss how to find your passion, how to stay true to who you are, what gets him through the really tough days in the start up world, how to know if you’re ready to start something new, and my personal favorite, why he would never wish starting on business on his worst enemy. Derek is hilarious and has really incredible insight into the power of authenticity through our struggles.


Here's a play-by-play, in case you only have a little time and want to hit your favorite parts first:

0:30 Welcome message

1:15 Derek’s backstory

2:00 What does Greatist do?

2:30 Some surprises that are coming your way

3:30 Derek’s explanation of kick-ass company

4:55 Derek’s decision-making process post-college

6:00 How to deal with the pressure to do what everyone else is doing

7:10 Making Google want you even more by accident

8:45 Working for a “high flying” start-up

10:15 How to know what’s right for you, rather than right for everyone else

11:55 The best unsolicited question ever during an interview

13:00 The road most traveled and how that’s made all the difference

13:30 How to know yourself and stay true to that

14:10 Figuring out what you want to do with your life

15:00 Building a legacy of your own by being yourself

15:30 How to get out of the “box-checking” life-style

16:30 Why Derek doesn’t wish starting a company on his worst enemy

17:30 This is the story they don’t tell you about the start-up world

19:30 Building a billion dollar business instead of a million dollar business

19:45 Derek’s personal passion and struggle and how they happen to be the same thing

21:00 Derek’s current obsession and how that fuels his business

22:10 How to learn the most you can from the negative influences in your life

22:30 A CEO who leads from the bottom with authentic service

23:20 The second most important thing it takes to make a successful business and positive culture

25:40 The non-traditional way to learn to be a leader

26:50 Learning from your mistakes

27:00 How to know if you’re ready and able to start something new

28:30 Derek’s advice for someone who’s scared to take the next leap

29:00 The only reason that Greatist is still around today

29:40 Derek’s favorite time management hacks and dealing with the lure of being “busy”

31:10 Time-blocking to spark creativity and optimize your schedule

32:20 Why sleep is one of the most important parts of being productive

32:40 What’s new and exciting at Greatist

33:40 Going beyond media at a media company

34:20 Derek’s #1 piece of advice for you

35:00 How to be authentic to who you are

35:50 How to get in touch with Derek

37:10 How to connect with us to get even more from this podcast


I've also compiled a list of references that Derek and I mention during the podcast here (links included!):





CBS Buys Clicker for >$100mm


Founder of Clicker


Greatist’s benefits and offers


Howard Schultz, Chairman and CEO of Starbucks


Bob Iger, Chairman and CEO of Disney


Richard Branson, Founder of Virgin Group


Jerry Colonna, CEO “Yoda”


Thanks so much for being here, guys!

I'd love to hear from you: What is the most insightful thing you heard during Derek's interview today?

Share your answer in the comments below!

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  1. Michael   On   21 Feb 2016 at 2:32 pm

    38 minutes well spent! Loved your views on killer culture, employee policies, authentic leadership, and getting rest! Thank you!

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