Why I Raised Venture Capital Again

It’s been a year and three weeks since Donald Trump was elected. It’s also been a year and three weeks since my first company, Nasty Gal, filed for Chapter 11 protection. That's a nicer way of saying “bankruptcy." But what a year and three weeks it’s been.

Today marks the announcement of the close of Girlboss’ $3.1 million round of seed funding, led by one of the best investors in the valley and (thank the lord) a woman—Nicole Quinn of top-tier Silicon Valley venture firm, Lightspeed Venture Partners. Joining her, alongside our existing investors Slow, BAM, Human Ventures, and others, are Gary Vaynerchuk and Troy Carter, two entrepreneurs I admire and respect so much.

I couldn’t be more thrilled and honored to have their support in what we’re building, and am equally thrilled and honored to have been given this second chance by our community of incredible women, many of whom have followed my own ups and downs, choosing to continue rallying together for Girlboss. And me, surprisingly, despite it all.

But, holy shit, is starting a business hard. That’s not to say this year hasn’t been awesome. It was my first year in as long as I can remember with zero public relations crises (save for the mediocre reviews of the GirlbossNetflix series). There were two incredible conferences, and a small but mighty team of incredibly smart, talented women I get to work with, and learn from, every day.

However, after years of layoffs, lawsuits and financial woes, I’ve never been told "no" more in my life than I have by investors this year. I heard everything from “media is dead” and “your pitch sucked," to “how is this going to be a billion-dollar company?" and “how will you 100x my investment?"

Some asked about what happened at Nasty Gal. It’s too long and depressing a story for any coffee meeting, investor pitch, and certainly this article (there will be another book!), but a lot happened.

We raised $40 million in 2012 at a $330 million valuation, which put an unreasonable price on our head, scaring away future investors. I was a young and naive founder. Hype-machine Fab.com collapsed. The unspoken mandate was to become the Amazon of fashion, or a niche brand, and we chose neither—getting lost somewhere in the purgatory of being an overpriced ecommerce business that failed to evolve and had hired far too many people.

100 people in the year after our Series A, to be precise. And to top if off, in late 2016, "Hail Mary" after "Hail Mary" vanished from our view, leaving us with an impossible choice.

I’m thrilled to have been rejected so many times this year. My pitch did suck! When I raised money for Nasty Gal, my investors wanted in so bad, they wrote the pitch deck for me. Sure, it was cute and unheard of that I was a community college dropout that built something with no credit cards, no investors, and zero debt and turned it into $30 million in revenue profitably—but without the diligent thinking that I’ve learned since, I now see that it was a recipe for disaster.

This year, the "no's" made the "yeses" all the sweeter. I could feel the improvements I’d made based on that difficult feedback in my strategy, my pitch, my thinking, my presence and level of confidence in the room, and it made a profound difference.

I found my conviction, and I found the right investor in Nicole Quinn and Lightspeed. By the beginning of November, our round was oversubscribed, a word investors use for people fighting to get into your company. Boy, is learning a blast.

The future for Girlboss looks bright, but I still have much to prove. There’s something to be said for having a chip on your shoulder; for not getting it right the first time and having the breadth of experience to finally exploit your hard-earned wisdom. I no longer inherit the mistakes I made over the years at Nasty Gal, too ingrained to unwind once they were set into motion.

However, a serial entrepreneur told me once that you “make the same mistakes over and over again,” even though you’ve learned from them. I’m hoping to sidestep as many of those as possible, and start Girlboss with 100x more intention than I did Nasty Gal. Maybe, just maybe, that’s how you become a billion-dollar company.

Girlboss is a feeling. It’s not me, it’s not you, but it’s the collective power of women coalescing to conspire, inspire, and trade resources. This chapter is about your stories—the stories you are still writing—and the crazy journeys I hope, inspired by our content and the community we’re galvanizing—you’ll say "yes" to, no matter how many "nos" you’re given. I hope you choose to live your life by asking yourself “will this sound good in my memoirs?” and leaping off those ledge with the confidence that in the end, everything will work out, and your memoir one will be one hell of a story.

We surveyed the women who attended November’s Girlboss Rally in NYC, and asked how many owned a business or wanted to own a business. The answer? 100 percent. I know from meeting thousands you on book tours that number isn’t a small sampling of this generation, but representative an entire generation.

Whether you’re side hustling, front hustling, or finding your entrepreneurial hustle inside a larger company, we’ve got you. But we won’t stop there. Women having money and finding ourselves increasingly in positions of power is just the beginning.

What we’re after is making that conversation moot, as soon as possible, so we’re able to think about our physical and mental health, wellness, friendships, relationships, and our impact on the world at large. Owning your power, your path, and your story can be just the beginning, if you’ll join me on this wild ride. I hope you will.