Keeping Up With The Kutchers

Jenna Kutcher 

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June 6, 2018


Ready for a Keeping Up With the Kutchers special episode on the Goal Digger Podcast? Tune in as Jenna and Drew answer your questions and nothing is off limits! You'll love getting to know this couple better and get an inside view to their marriage, businesses and life!


Ask Jenna Anything… with a major twist! I present to you “Ask Jenna (and Drew!) Kutcher Anything!”

Yup, that’ right. My husband, Drew Kutcher, and I are about to dig into your questions revolving everything from marriage to personal all the way to business.  I fielded your questions from both the Goal Digger Insiders FB group and the Goal Digger Instagram (if you’re not hanging out there, you’re totally missing out!)

We are fully covering ALL the nitty gritty details of your questions… If you’re wondering how we balance business and play, what our first kiss was really like, what our relationship story is, or what it’s REALLY like to marry a #girlboss, then this episode is for you!


  • Jessica Naomi Seale I want to hear Drew’s account of the time you said y’all should kiss once just to see what it would be like. 🙂
  • Joelle Bradfield Drew: Was it ever hard to support Jenna in her full-time business ownership pursuit while you were working corporate/9-5? If so, how did you find ways to work through it together?
  • Kelsey Hanson Aight, this ones personal. What’s the most embarrassing thing you’ve done in front of him? 🙈😂 and vice versa!
  • Leah Strickman This is awesome, you guys are both so sweet! I actually have a question that I’ll frame a little differently for each of you 🙂 For Drew, has it been a challenge to learn from Jenna professionally as you grow your business? And for Jenna, how is working with Drew different from working with your usual audience? (I ask because it sounds like you’ve definitely given a helping hand with social media, email lists, and some other business-related stuff, and I’d love to know how that’s worked for both of you!)
  • Janita Court Who hogs the bed!? 😆
  • Mellissa Alexandra I know there’s a level of adjustment that comes with working together under the same roof, and while it’s great being with your person so much, everyone needs some personal time and space! What are some activities that you and Drew like to do separately? 🙂
  • Lindsay McCoy This is kind of for both of you. How do you feel about the wife being the “breadwinner” (hate that term!!)?  I am starting to make more money than my guy. Thankfully I have a dude who thinks it is GREAT and Drew seems similar, but I have observed this being struggle in many relationships with our society so skewed to the “man working, woman home” thing- even still in 2018.
  • Victoria Rayburn How did you care for your marriage while Jenna was building her business?
  • Denise Viscardi Ferreira What’s the one most important thing you’d each share to new entrepreneurs that you wish you knew when you first launched your own brand?
  • Kathryn Frazer Super excited for this! I’d love to know how owning a condo in Hawaii and renting out via Airbnb is going. Any big lessons you’ve learned? Anything that surprised you about running a vacation rental/ wishes you knew beforehand?  We love Maui too and are hoping to make this happen in the next couple years and would love an insiders point of view!
  • Kari Claussen Where did you get your dogs? And what are their personalities like?
  • Amy Kratzer Tell us more about your missional hearts and what sets your souls on fire. If you had all the money in the world, what more would you fund, support and/or get behind? Maybe what’s one thing that only you and Drew know, like a dream in your heart you haven’t shared? You’re always getting behind our dreams, I want to get behind yours.
  • Morgan McCollow Is drew ever uncomfortable when you share your personal life with your followers? Do you decide with him what you’re going to share beforehand?
  • Hannah Beth Have you thought about moving to Hawaii full time??🙈
  • Kristi Monte I’m moving in with my boyfriend of over 2 years on June 1st! I’m so excited but also scared to live with a boy 😂 He’s super clean like Drew and a great cook, and I know we get along great and balance each other out…. But what are some things you guys learned about each other or your relationship after you moved in together? Any words of advice for us?


Wow, wow, wow! This fella! These questions! This episode was totally unscripted, uninhibited, and truly showed what life is like in our marriage, work, and friendship. As always, the questions that come out of our FB group and Instagram make my day! Cheers to YOU, my Goal Diggers! Thanks for keeping life oh so fun!

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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