How to pivot after failure: This is Girlboss Sophia Amoruso 2.0

This article was originally published August 16, 2018.

Thrifter turned mogul, Sophia Amoruso, has had to rethink her career after being hugely successful — then having her company go bankrupt. After first bringing vintage finds to the fashion masses through Nasty Gal (a shopping site once valued at $280 million), Amoruso deftly shifted into heading a media company titled after her wildly successful,inspirational tome, Girlboss. Her company now includes Girlboss Radio, a podcast where she interviews women from all walks of life on business, success, drive and more, as well as Girlboss Foundation, which helps to mentor up-and-coming women in business. Girlboss Rally is also back for it's forth installation, this time spanning two days in November in New York City, featuring talks, networking events, headshot photo booths and more, all with the aim to help women find their voice and a community.

Girlboss was a bold move from someone who sustained a major hit, both personally and professionally. But you wouldn't expect any less from Amoruso, who was in town to promote the Shoppers Drug Mart upcoming fall #BeBold campaign. With her apparent cool comeback, version two success story, and her style, we couldn't wait to speak with her about the highs and lows of rebuilding her career, and the major lessons she has to share.

How do you define success, now?

Success, for me, is about being able to build a business again, and have a personal life at the same time. In my 20s, I had the trappings and the look of a personal life, but nothing very meaningful actually happening. I mean, I bought a house and I got married to the wrong person… and I was like "look, I am at a luxury resort, drinking alcohol." And I think the alcohol actually hid a lot of the things that were really happening, and it looked like I was winning. And I was on some definition of success, but today it's about having meaning in my life and my career. And staying close to my family. I need to go visit my mom! And learning more, like how to be an active participant in my journey, rather than letting — and there's something to be said for serendipity — the opportunity lead me, rather than leading it. Now I want to be a lot more deliberate in my career and how I build a business today.

What was the hardest part when starting phase 2.0 of your career?

That everyone was watching! 'What's she doing? Can she do it again?' Just the outside voices, mostly. I am lucky to have a platform. Starting a business, like I did when I was 22, where no one knew who I was, beating down doors, getting so many nos. I still get so many nos; raising venture capital has been super challenging. But that hardest part was the outside voices, which I can tune out to a certain extent. Reading comments online can be a really bad idea. That, and regaining my confidence. I am less naïve, I know how hard everything is. I had a lot of early success and I think naivety can really work in your favour, and I have a lot less of it today.

What advice would you give to your younger self, when things were going a bit south?

Get closer to your business. Stay close to the financials, hold people accountable, don't just assume they're gonna, because they're C-level executives, they're going to keep themselves on track. Physics tells us that something observed behaves differently than something not observed. And humans are the same way.

What has been your key to success, through Nasty Gal and now onto Girlboss?

I think persistence. From everything that I've done and learned and also read about entrepreneurship, from the experts who have had incubators, who have nurtured hundreds to thousands of businesses, they say persistence is the number one trait of a great entrepreneur. Because it allows you to move through setbacks quickly. And instead of hearing no, finding way to turn nos into yeses. Or engineering or reverse-engineering what you want. Doing more with less. No one is going to do it for you. No mentor is going to drop out of the sky and get you there.

What advice do you have for people moving into the second phase of their career?

When you're young try everything you can. And don't be afraid to step back. I moved an hour outside of San Francisco to a suburb, into a pool-house with no kitchen, to start Nasty Gal. I was 22, I had no friends nearby. It was all I did. I obsessed and I put in the hours. Nothing great comes without hard work, especially in the early days of your career — to build a platform for yourself, to build a business and learn as much as you can in a short time. Also, when you're unhappy, knowing when to pivot.

Balance. What does it actually look like for you now?

I think about balance less than I do about integration. So integrating your personal life and your business life, because you can practice self care at work or when you take a lunch. Be more mindful of how you chew your food — I am trying to chew my food more! Someone told me to make it liquid before I swallow it. I think I eat faster than most people around me. We live in an always-on, digitally connected world. So being able to find ways to integrate the two, without letting work take over.

Are you ever able to do a digital detox?

Um, no. On weekends I'll turn my phone off sometimes. I try not to email my team on weekends. Sometimes if I am catching up, I'll email people on a Sunday, and they don't really realize that I am not expecting them to respond right away, so some people do. I use a Gmail plugin called Boomerang. It's great, you can push a button that says to deliver it at 9 a.m. on a Monday, so that you write the email on Sunday and they get it on Monday morning, so you're not bombarding people.

What was the best financial decision that you ever made?

Probably dumping my money into a house so that I can't spend it. I think tying up a certain amount of your liquidity in something that is a long-term investment, especially one that you get to use! And it's your own. You have to make the repairs and it's a lot more work, but it's something that I am proud of.

And the worst?

Reinvesting in Nasty Gal, during difficult times. Putting a lot of my own money back into the company to try to make it work, when I already had so much exposure and risk in my "net worth". I should have protected what I did have more. It seemed like a very noble thing to do, but I ended up losing it. Let's hope I can earn it again, cause I am going to need it.

For more from Sophia, including the three things she does when she wakes up, check out our rapid fire round with her below!

Life with Sophia Amoruso — A tell-all in 13 questions:

What is your favourite bold makeup look?

I love a red lip. I think you can be bold while being subtle at the same time. I am a fan of the monochromatic look, because you can use a cheek product on your eye. It feels very modern. I use RMS which is a clean beauty brand. The products are such multi-taskers, and I spend a lot less time on beauty than I used to. But a bold red with a clean eye.

First 3 things you do when you wake each weekday morning.

Look at my phone. Make coffee. Get on the treadmill.

What's do you tell yourself when you need motivation?

Stop it, because you're going to ruin everything — you're going to manifest what you don't want.

One book you'd recommend to everyone?

The Hard Thing About Hard Things by Ben Horowitz, who's one of the founders of Andreessen Horowitz, one of the biggest venture capital firms in the world.

Favourite thing to do with your down time?

Nothing. Just nothing on my calendar, no plans.

You have an entire weekend to binge watch stuff - what's it gonna be?

Goliath on Amazon.

Who is your favourite fashion designer?

Cult Gaia

Your celebrity crush!

No. I mean Vincent Cassel.

Your "airbag in case of impact"? The person you turn to when things go south!

I'd say my girlfriend Monika, who lives in New York.

Secret internet obsession!

Googling every kind of ailment that I could possibly have and freaking out.

What makes you nervous?

Interviews, sometimes. But actually public speaking.

When do you feel the most bold?

Honestly, I feel really confident and bold when I feel like I look good. It sounds kind of superficial, but I have more confidence when I've spent time on myself and taken time in the ritual. Beauty is a form of selfcare. Even if it's subtle, those small changes can bring so much confidence in your day.

The best compliment you've ever received:

'You look kinda like Anne Hathaway,' from some guy at a bar. There are probably better ones! I just think that's a funny one.