Closet Clean-Out of Jessica Kupferman: CEO of She Podcasts | EP 56

Closet Clean-out Conundrums with Jessica Kupferman, CEO of She Podcasts

This week, our Stylist Extraordinaire Holly Katz has been doing the LORD’S WORK, People! She is with her BFF, Jessica Kupferman, CEO of She Podcasts, cleaning out her closet, swearing up a storm and getting Jessica styled for a big-ass upcoming event: She Podcast LIVE in October – the largest in-person gathering of women podcasters, audio content creators and story tellers.

Hold on to your underwear – because this episode is OUT OF CONTROL! Holly and Jess reminisce about being besties since their days at summer camp (Jew Camp, as Jessica likes to call it). She is a dear friend and a past guest and friend of our Podcast, and Holly has been threatening to go to her house and clean out her closet FOR YEARS.

And, damn, if Holly did not do just that for 72 hours. She is here today to report that 23 bags full of shit are now gone. In her defense, Jess’s husband and mother-in-law jumped on the clean-out train, so they added to those piles. But Holly is so proud of them – they were all drinking the Kool-Aid – and there wasn’t even any crying!

Jessica asks a shit-ton of great questions about how to avoid the dreaded Crimes of Fashion, and Holly shares some of her deepest, darkest secrets on how proper styling, fit and selection can make a world of difference in your confidence – AND – she tells us how to make style decisions easy – and perfect – just for you, every day.

  • Should Jessica keep her Chicken Purse? It was a hard decision, because it was next to a pile of scarves, next to a huge, pink bin full of purses, which Holly threw out, because they were little sequin, tchotchke, furry, weirdly handled cigar box purses.
  • How about the hospital plastic take-home bag full of unmatched socks (that have been sitting in Jess’s closest for FIVE YEARS)?
  • Perhaps her T-shirt collection should be divided into SLEEPING SHIRTS and GOING OUTSIDE SHIRTS? Because she wears them for both.
  • How many body types are there? Three? Six? A Million? And which one do we want?
  • What is a bra fitting? Who needs one (Jess knows her own damn boobs, thank you)? Why do we need them? When and where do we get them? WTF?
  • And then, in the middle of this shit show, Holly finds a legit fab designer for Jessica who – GET THIS – went to their Jew Summer Camp! OMFG. We. Can. Not.
  • At one point, Jessica’s husband gets involved, because he has OCD and cleaning up shit turns him on. So, he started getting hot under the unders, and … bleep, bleep, censored, censored.
  • Jessica has a load of wigs in her closet to deal with. She had a Mohawk once that she needed to fix. Try to keep up, it’s ridiculous.
  • And finally: Accessories! Neck fans purchased on Facebook because you menopausal are not accessories. Stylish glasses that fit your face and classic costume jewelry mixed with your fine pieces is your jam!


Holly literally clears out the crap, opens up Jessica’s space for positive energy and leaves her with all the confidence in the world before she stands on stage and welcomes the podcast world to She Podcast LIVE in Scottsdale, AZ in Oct. She is gonna rock it!

So, what’s in YOUR closet? Are you ready for a fresh start?

Listen here for this week’s episode:



She Podcasts:


She Podcasts LIVE event:


“I woke up this morning, I brushed my teeth, I went into my closet. And I picked out a comfortable, stylish outfit in under 30 second – and in fact – I had several to choose from. The miracle of that is that none of those outfits are pajamas. ” – Jessica Kupferman


“And I’ll say it again, not every day is going to be a home run. But why not set yourself up for success? Jessica has this big event coming up, which I have dressed her for. She’s got plenty of things to wear, and she has realized that she has over-shopped. Not a big deal. We know that now. So we got rid of the worst, and we’re keeping the best of the best.”

– Holly Katz

Listen now!

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