The Nasty Icon of Retail, Sophia Amoruso (#112)

The Tim Ferriss Show with Sophia Amoruso

“I like to make promises that I’m not sure I can keep, and then figure out how to keep them.” – Sophia Amoruso

Sophia Amoruso (@Sophia_Amoruso) is the Founder and Executive Chairman of Nasty Gal, a global online destination for both new and vintage clothing, shoes, and accessories.

Founded in 2006, Nasty Gal was named “Fastest Growing Retailer” in 2012 by Inc. Magazine, thanks to its 11,200% three-year growth rate.

Sophia has been called “fashion’s new phenom” by Forbes magazine, and she has become one of the most prominent and iconic figures in retail. She recently founded the #GIRLBOSS Foundation, which awards financial grants to women in the worlds of design, fashion, and music. Sophia’s first book, #GIRLBOSS, is a New York Times bestseller published in fifteen countries.

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

#112: The Nasty Icon of Retail, Sophia Amoruso

Want to hear another podcast from the founder of a rapidly growing business? — Listen to my conversations with Tracy DiNunzio of TradesyIn our three-part series, we explore many key questions, including: How has she created such high-velocity growth? How did she recruit the investors (e.g. Richard Branson) she did? What’s been her experience as a female founder? What are her biggest mistakes made and lessons learned? Check it out.

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QUESTION(S) OF THE DAY: What rapidly growing companies interest you the most and why?  Please let me know in the comments.

Scroll below for links and show notes…


Selected Links from the Episode

Instagram | Twitter | Podcast | #GIRLBOSS

Show Notes

  • How do you answer the question, “What do you do?” [5:21]
  • The poopy pants story [9:06]
  • How Sophia Amoruso started her business [13:51]
  • Why Sophia is so good at selling on eBay [18:36]
  • On learning to write persuasive copy [21:26]
  • The inspiration for Sophia’s next book [23:21]
  • Most gifted books and favorite writers [24:31]
  • How to manage the stress of a quickly growing company [28:21]
  • The origins of Nasty Gal [30:41]
  • On the transition from eBay to [33:56]
  • Advice for those seeking to grow a business similar to Nasty Gal [39:51]
  • Helpful books for those seeking to lead fast-growing companies [42:41]
  • The biggest challenges while growing Nasty Gal [45:01]
  • The mentors and/or resources that helped Sophia learn leadership [54:21]
  • Sophia’s biggest struggles [1:01:56]
  • Tips for interacting with the media [1:06:21]
  • What is Sophia Amoruso’s go-to drink at a bar? [1:15:56]
  • When you think of the word successful, who is the first person that comes to mind and why? [1:18:31]
  • Rapid fire questions: favorite movies, surprising world-class abilities, and common misconceptions [1:21:01]
  • If you could put a billboard anywhere and write anything on it, where would it be and what would it say? [1:24:26]
  • The process behind stepping down as CEO [1:26:51]
  • What purchase of $100 or less has most positively affected your life [1:29:36]
  • Daily rituals [1:31:26]
  • Advice for your thirty-year-old self [1:40:46]
  • What are you most looking forward to in the next 12 months [1:42:01]
  • Asks or requests of the audience [1:43:51]

People Mentioned


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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63 Replies to “The Nasty Icon of Retail, Sophia Amoruso (#112)”

  1. Tim,

    This one really had me laughing at my desk today. Multiple layers of inadvertent humor. From stories about “fouling out” to Tim being accused of asking about Sophia’s “well-developed” glutes…pure gold. At least 2 of my co-workers stopped by and asked me what I was giggling about. Good stuff!


  2. Uber is super interesting because of the disruption they have had and the unprecedented growth they have seen around the world. Would love to hear from someone there.

  3. I really enjoyed the billboard answer. As a woman I, too, have gotten the “smile” command/suggestion for years. Sophia put a spin on it I hadn’t thought of, that a woman not smiling is perceived to be judging people. Being judgmental is flaw of mine and a male friend has told me that he(and other men) feels intimidated and not attracted to a woman who is always judging them.

  4. Always appreciate when you invite kick-ass women onto the show, as there are so many and your guests are primarily men.

  5. PLEASE don’t poop on your normally fabulous podcast! Would you start a podcast interviewing Tony Robbins asking him to relate a story of how he pooped in his pants? Don’t recall you asking a male guest such an embarrassing question but I may be wrong. We have NO interest in hearing about your guest’s poop or your puppy’s poop. Too much information. Do you REALLY think your audience wants to hear this?

    1. You don’t speak for the audience Kay. You speak for yourself. So your ‘We’ is your ‘I’ and your ‘I’ does not speak for ‘Me’.

    2. It didn’t bother me that she sounded “disengaged”. What I heard was someone who is feeling a little down.

      I don’t expect every interviewee to be a Jerry Sienfield. So she’s raised millions, or whatever… that doesn’t mean she’s an entertainer.

      I find it strange people complain about this podcast, using the word “disappointed”, as if every single one has to be perfectly suited to taste.

      This shit is FREE. If I don’t like a podcast, I stop it and move on. I actually got a lot from this one:

      1. You don’t have talk and act like “star” to be one.

      2. Even the most “successful” business owners cry on their pillow at night.

      3. Keeping your business small is a lifestyle decision, and can be a very good thing.

      4. And ANYTHING consumed by the public is considered a product, and a “customer” mentality sets in, even if it’s a free podcast. This is both good and bad.

  6. It would have been interesting to hear her discuss how taking on huge investments changed the tempo and focus of Nasty Gal and how it may be related to the subsequent fall in sales volume. Former employees mentioned the average cost of a item increased to $100 even though the original focus was affordable clothing.

    PS: Your homepage’s top section has a horizontal scroll on my laptop screen. “overflow-y:hidden” should probably fix it.

    1. Hi Sapph, I agree that would have been a cool question to ask. I feel like she indirectly spoke on this when she said keeping your business small could be a definition of success, because that’s the life you want to have.

      She also mentioned not feeling like she had a lot of choice or control in decisions that were made. “You have to do what’s right for the company”, she said.

      She also kind of laughed in that slightly nervous, nonchalant way, when saying that she did follow that guys’s advice to stay CEO.

      I’m reading into it, but I got the feeling she was saying that having such a big company is not all it’s cracked up to be.

  7. First off, I love the podcast. Always great guests and good info!

    Secondly, I apologize, this comment is a general question about the podcast not specific to this one.

    I am searching for a particular podcast episode and cannot, for the life of me, find it.

    Background: I was driving home a few months ago listening to an episode of the podcast and I believe Tim was interviewing someone he didn’t know well and I though he had a medical background. I really thought it was Sam Harris but when I went back a re-listened to the podcast I didn’t find what I was looking for. When I was driving I was drifting in and out of the episode and drifted in when the interviewee started talking about making real progress in his area of work and how it is hard to make real progress if they people on your team only have one main area of knowledge that they concentrate on. Because if there suggestions, in their area of expertise, are not agreed with they tend to get defensive and halt progress, so they constantly need to be validated that they are smart before they can move on.

    I am I going nuts? Does anyone remember this in one of the podcasts? I know this was just a small part of the podcast episode and it might have only been a 1 minute conversation between them but it’s really driving me crazy that I cannot find it. I appreciate any help.


  8. Hey Tim

    Just finished listen to John “Jocko” Willink interview and that made me think regarding morning routines , Just a suggestion have you thought about compiling from all your interviews peoples morning routines maybe page or even book on the best ones ?

    1. Hey Jonathan,

      Do you know the book “Daily Rituals: How Artists Work”? It was the #2 book in Tim’s Book Club.

      [Moderator: personal business content/link removed]


  9. Tim, as a huge fan of your podcast and a (former) fan of Sophia Amoruso (I really enjoyed her book and the entrepreneurial ideas in it), I was very disappointed on this episode. She did not sound engaged or all-there, and I think you were not on your best game either, although I noticed how you tried to rescue her on several occasions. Your interview with Tracy DiNunzio was so much more interesting and engaging. Your podcast rocks, but lately you are not going as deep as you were before into the areas of your guests’ expertise. That’s where the money is! It would have been a lot more interesting to hear from Amoruso about fashion, aesthetics, fast growth companies, how taking venture money changed her company, about building a loyal following of customers, etc….(That’s why interviews with Tracy DiNunzio’s, Robert Rodriguez, Pavel and Adam Gazzaley were so much richer).

    You still have the best podcast in the market. Keep up the good work, man.

    1. I have to agree here. It felt as though she did understand why you were asking her questions about her morning routine or who she thought was successful and was annoyed by the questions — “Sigh, I don’t know?” Guests are invited on the Podcast because they are a boss at something, and people care to know their opinion/reasoning on those topics, regardless of the specific answer.

      I do however, have to disagree with the poop comment, that sh!t was hilarious… 🙂

      1. That reminds me, that she actually forgot what she had answered so Tim had to read off of his copy of her answers. Let’s not leave out Tim -asking a 31 year old what she would tell her 30 year old self? Nice recovery though, Tim 🙂

        Anyway, after a fast start that reminded me of a crazy story about a bottle of milk someone left out, a frantic dash into a store in San Francisco, a “WHERE IS YOUR BATHROOM”, and a leap over a mop and bucket, perhaps comparatively the rest of the interview seemed to struggle. Lesson learned – save the best stuff for last?

        Or maybe it was partially her low-key personality – she doesn’t have an MBA “but I raised 70MM so I guess I figured it out huh?”, so perhaps Tim’s stock questions were a little boring to her?

        I’m sure Tim’s forehead was sweating a little when he launched into his workout questions about glutes and Greece – whoa, how to step into a minefield – but he seemed to recover and she didn’t hang up then and there. Tim practicing his “negative” learnings from Neil Strauss? Or Sophia making a show of haughtiness to play to the audience? I see Tim’s point in asking these (he’s a data guy) but maybe with guests like Sophia you have to go off the map a little? Although how far? With Jocko, there are certain questions you just can’t ask, so there is this delicate balance.

        This is why hosts like Conan and Fallon get the millions – they can dance the dance, rescue a slow interview, extract brilliance from a guest, etc. Some of Seinfeld’s “Comedians in Cars..” are magic. To make a small segway, Seinfeld seems to follow the same model as Tim – he’s interviewing someone that he truly respects, that he is interested in, and he would be happy to chat with regardless of the camera and audience.

        Part of the fun of Tim’s podcasts is that these are folks I never would have thought of listening to, and they turn out to be fascinating, and Tim elicits great stories from them. Rick Rubin comes to mind, Arnold, Pavel, Stanley, Jocko, Richard Betts, . The Sitting in a 150 deg sauna – that is awesome just by itself. The riveting, mind-altering interview with Mark and Dan.

        Well Sophia and Tim, thank you as always for an entertaining and thought-provoking interview. I never heard of Nasty Girl/Gal as, like Tim, shopping is not my thing, but I will check it out and am interested in reading the book.

      2. I also agree here. I think she may have been eating at one point and seemed totally disengaged or stoned! I actually though… ‘I think she’s smoking weed.’

        (I feel) It’s a pretty big deal to be on the #1 business show on iTunes and I felt like Sophie was answering questions as if being interviewed by a rookie. Tim did try to take her with him, but at times it was hard to listen to. Also agree on the difference between Tracy DiNunzio’s and this one (and many of the other amazing episodes.)

      3. One more point: she sounded like she was working like crazy and completely exhausted. That’s the double-edged sword – she got where she is by working like crazy, and doing things like raising 70MM, and she built her business. I think it was the Pavel interview, or another one, where Tim asked the “what would you tell your 30 year old self”, and I believe it was something about easing off the accelerator. You can do the 20 hour workdays, we’ve all been there, maybe a month, or three months (with varying degrees of success), but once you get there (wherever that is), it’s time to realize you can’t do everything. And that was one thing that jumped out at me, that Tim brought out in the interview – that she is trying to do everything. Yes, we all wish to be so successful, so that the demands pile up at the door, the phone never stops ringing, etc etc. But for sanity, well, Tim is _the_ perfect person to talk to. 4HWW – it’s all there.

    2. I think you guys just weren’t really communicating well towards the end. She mentions some fairly standard seeming things about the media (which you are to her, or so it seemed) that you unfortunately play into with the whole butt tangent – your demographic appeal being largely men… right? Things really shut down after that, which is unfortunate, since she has a unique perspective.

    3. have to agree. this podcast was almost painful to listen to at times. seems like it was hard for her to chew gum and talk at the same time, so to speak. it didnt seem like she was paying attention, had poorly thought out answers for many of the questions, and seemed disinterested in the whole interview. this is what i got out of the podcast: if this half-wit can do it, anyone can. certainly not up to the caliber of the typical person interviewed on this show.

    4. Definitely agree with the above. In fact I had to stop before the end of the episode after hearing the answer about the $50 purchase …. a burger?? really?? The show is great though!

  10. Great Podcast Tim. You mentioned that you met Gabe Newell of Valve. For someone who is interested in organizational structures like the one that Valve uses, would you recommend reaching out to Gabe or another at the organization? Curious who the driver of that system is. It’s based on Holocracy, see for more info.

  11. Hi Tim,

    Great interview, very spontaneous in my view. You mentioned about memory pills, any chance to elaborate on that?


  12. Sophia was a great guest although I was struck by one thing. For someone so successful and a relative powerhouse of fashion she seems so unsure of herself. Its easy to feel as if successful people have it all together but they’re just trying to figure it out as they go like everyone else.

    Thanks Tim – another great show!

  13. Great podcast I really like her and what she has accomplished after hearing this podcast. I am a designer with a small label and have looked up to her and Betsy Johnson on what they have created. I found in interesting that her first love is music. I come from the punk rock and techno music world and also use the fun of music and put it into fashion. Fashion needs to be fun and that is what she has brought to the world and part of her success. There are a lot of haters in the fashion world and I think she gets a bad rap.

  14. The companies rep in the fashion world is that it a badly managed mess. Maybe Tim you know some one that can help her out and turn it around.

  15. This was the least enjoyable TFE yet for me. You were both distracted and unfocused. Between the dog stealing your attention, her constant device sounds (conversation vampires) and your need to coach her along. Each episode has fueled some vector of my interests, and this one reminded me to love the one I’m with. Thank you for sharing your work and play!

  16. I have listened to between 85 – 90 of your podcasts over the last 4 months and I have recommended them to numerous friends. This is the first one that I didn’t feel like the guest cared about being on the podcast. It seemed like you were really struggling to create any type of flow. I am sure there are a lot of people who will like the episode but for me it was a miss despite Sophia’s interesting background.

  17. Hi Tim,

    I read a twitter comment of someone praising your podcast for the great questions you ask, so I came to listen and extract some accumulated knowledge from you…God it was a great decision.

    I got a podcast myself (we get to be #3 on méxico and #4 on Argentina in management and marketing) and I’m always looking for good questions. I get a ton of them in this one and a half hours.

    I will listen more often to you so I can learn more. Every time I get in contact with your content (mostly the 4hww or 4hb) I get a ton of value.

    Take this as another of your daily fans confessions.

    Cheers from Salta, Argentina.

    PD: I borrowed your mourning routine too…and your diet.

    PD2: Really loved your post about suicide. Priceless.

  18. The Tim Ferriss podcast is the best thing that happened to me in a decade. If you want to grow and work on yourself, achieve what you can, TF show and all the episodes starting from part1 and on is a greeeeat place to start.

    I agree with a lot of people here that Sophia didnt speak a lot, if any, about her core strenghts and what made her an admirable entrepreneur. Tim used his best to get the most out of her, and continues to make a great podcast.

    I dare you to try and get one person on the podcast Tim, Fethullah Gullen 🙂 would be great if the expert of deconstructing excellence, TF, would show the podcast world the existence of such individuals.

    Sorry guys, typing on a mobile phone while sitting at inlaws 🙂 mistakes and nonsense all over the text 🙂

  19. Yeah, I don’t think she was very engaged either. She just didn’t seem to be a good fit as a guest for this podcast. She suggested alcohol for depression??? Maybe she thought that was cute, but not very good advice for anyone looking to be inspired.

  20. What a tough person to interview!

    Sophia is disarmingly honest and funny, and clearly had you off-balance and sweating a few times. Hearing you squirm was definitely part of the fun for me in this interview (sorry!).

    It goes to show that no matter how good you are at anything, there are always opportunities to grow…

  21. Great work Tim, you showed a lot of tactical skill in keeping this on the rails.

    It was clear she wasn’t taking the interview seriously and that was disappointing.

    If you are too busy then cancel and reschedule, don’t come on and give those answers like your checking email and eating at the same time.

  22. Sophia strikes me as successful in business in spite of herself. I got the feeling she doesn’t like herself very much. Granted, maybe she had the misfortune of being recorded during a particularly bad week.

    I love the podcast and almost always find some value in it. Thanks for doing it Tim.

  23. I loved this podcast. You mentioned a $4 bottle of white wine that you picked up at TJs that was great, do you remember the name? I’m dying to know!

    Thanks for always producing such a great show!

  24. Love your work Tim – you give great voice. Think I’ve listened to about 30 different episodes and this one was great from a content perspective but was kinda painful to listen – the first ever I had to turn seems like she was having a bad day or her publicist put her up to it…you did a great job despite! Keep it up!

  25. Tim, I’ve been listening to your pod for a couple months now and I love it. She was (another) awesome guest. Bluntly: In this one you seemed unprepared and off your game; it felt like you mailed this in.

  26. Hey Tim

    Love your books, shows and blogs!!!

    I am in Australia and wanted to try the Athletic Greens offer you have. Is it only available for USA and Canada residents?

    Cheers, Mal

  27. Can you state again what Tim mentioned what he used to record/edit podcast? recording software/microphone/editing software?


  28. Tim did the best he could with this episode. She started strong with a funny story and a great quote on commitment. Then she just crashed and burned. It was awkward to listen to this one. Parts of the interview were uncomfortable and I was amazed by the shallow answers coming from a person who built an impressive business. She was at a loss for words or what a word meant (objective/subjective). Awkward answers to questions about depression and a blank billboard everywhere. One has to wonder was she managed out as CEO by board or is keenly self-aware of her strengths and weaknesses.

    1. I have to agree that this wasn’t among your best podcasts. To give Sophia the benefit of the doubt, I think she tried to use dry humor which didn’t necessarily work… but I think she also came off as distracted (whose phone was going off?). It’s a shame as she is a very interesting person with likely more to say than she did here.

      Good work as always, Tim! It’s the tough ones that improve you.

  29. What a multidimensional woman! Laughs at herself but is serious, not trying to be sophisticated at all but is so clever… Please enlist me in your ‘no more smile more’ campaign! And million bonus pints for watching Sergo Parajanov and loving Georgian art! Tim do check it out, you’ll thank Sophia for the experience!

  30. Hi Tim!

    I love how far Sophia has come and give her a lot of credit for that, and actually was a fan before listening, but this was really dissoppointing. Being antagonistic in general, but particularly in the field of fashion, is not progressive, especially from someone so young and such an accelerated entrepreneur.

    Listening to this was not inspiring or motivational for female entrepreneurs.

    I like that she’s humble, but she’s loaded and seriously a snob. Everyone else is obviously buying it, but I’m not. I’m not trying to be biased, but it sounds like she should read some Tim Ferris.

  31. This was weak interview. Tim, thought you did a great job trying to pull what you could out of her – she didn’t seem engaged. I couldn’t decide whether to keep listening or not.. but I did, hoping I’d come away with some nuggets. The biggest takeaway was to really get tight about my own language. People, we gotta stop using, “like” “I don’t know” “I mean” and “um.”

  32. Just catching up on 4HWW posts and was super excited to see this interview with Sophia Amoruso. I’m a big fan; she’s successful, funny and laid back. However, I am constantly hoping for an informative & inspirational story, and have still yet to come across it. Having read her book Girlboss and watched different interviews, I hear the inspirational story (at home eBay’er to retail queen) but don’t seem to hear any details (apart from the obvious; use eye-catching thumbnail pics etc).

    I sit in hope that she gives us more of an insight to the business’ rapid growth soon.

    In the meantime, I’d highly recommend Marc Ecko’s book ‘Unlabel’. A super inspiring and an interesting story which provides details into the do’s and don’ts! We can learn a lot from other peoples success/mistakes.

  33. Hi, I hope Tim/forum members could answer this for me. I am working for an online clothing shop and was wondering if anyone has any experience contacting brands in an attempt to get a retail agreement to sell their clothing online. I have never done this and am not sure of the correct way to go about it. How is initial contact usually made? and how to these kinds of deals work? If any one has any advice that would be great!



  34. Hi there Tim, I just checked the Athletic Greens discount link, and it says ‘page not found’. It was still working yesterday, and I was about to go purchase these today. Did something go wrong with their page? Or did I just miss out on the deal by a few hours? Thanks.

  35. I read the comments on this episode before listening and thought ouch, some harsh criticism about the guests attitude. On reflection though after listening to it, I appreciate this episode for the fact it exposed Sophia as quite human.

    The guests on Tims podcast are so accomplished with inspiring intellect but I often wonder about the chinks in the armour. We all have them. For me, this episode from Sophia was a good example of someone who started very young, (is still young) and has worked her way through her success yet acknowledges this is hard shit.

    I found that pretty refreshing and was able to identify with a lot of what she said. Overall I thought the episode was casual, conversational and ‘human’ which is a nice balance to the many that appear ‘superhuman’.

  36. Tim,

    You were super-diplomatic in this interview, taking the blame if Sophia didn’t understand a question and pretending not to know how to pronounce Rainer Maria Rilke (you’re fluent in German!), and it was great to discover the story of someone who went from working in Subway to being worth $250 million. That’s so much more inspiring than someone who stepped out of a Harvard MBA and did the same thing! Don’t be put off by the critical comments below and please keep taking risks!


  37. This episode was a little harder to get through, only because Sophia did come across very scatterbrained at times. But when I looked at the interview through my “creative” filter, it was easier to understand where she was coming from. She is not an expert in running a business and she made that clear when she chose not to be CEO of her company. She is a “creative” and she is quirky and honest. Plus, she is beautiful, which is something our society values. We all have a right to use what we have to get ahead. More power to her! I hope she is able to realize all her goals and inspire other women to be a #GIRLBOSS.