The Middle Finger Project is my scandalous website, targeted at women who want to strike out on their own and do something meaningful, creative, and entrepreneurial with their careers. It started off as a lifestyle blog 10 years ago and evolved as I realized that I was talking a lot about having purpose, but I wasn’t offering a solution. I drew from my background in marketing and sales and I began to teach people how to sell themselves, their ideas, or cause.
Initially I didn’t have any intentions of using this as a business platform—I was trying to strike it out on my own as a freelance writer at the time. I had two separate lives: one was sharing ideas and thoughts on the blog, and the other was looking for clients in Philadelphia and hating every minute of it. There were a lot of, like, pharma companies and medical device companies—they needed writers, but it was horribly boring.
I found myself sleeping in my car in a Kmart parking lot. That was kind of my rock bottom moment.
I hadn’t really made a meaningful leap yet and then my living circumstances changed and I didn’t have anywhere to go. I didn’t have enough money for a deposit on an apartment, or any family nearby. So, I started staying with this guy I was seeing. He was mysterious, very good looking, charming, but turns out in the end, he was absolutely someone I should not have been associating myself with.
So I found myself sleeping in my car in a Kmart parking lot. That was kind of my rock bottom moment. I hadn’t made the connection yet that I could write for people on the internet. That night in the Kmart parking lot I got really desperate and started thinking about what people do when they’re in a desperate situation. You might sell a bond, or a family heirloom, or your car. My car was a mess so I couldn’t even sell that.
I heard an ad on the radio to pre-order this new Rihanna CD and it clicked with me that they were selling something that didn’t exist yet. I started thinking about pre-orders for something like a book. It made sense. I had never written a book before but I was a writer. I realized I could sell my ideas and that’s what books are—a collection of ideas packaged up into a product. That night I decided I didn’t have any other choice. So I made a quick sales pitch, I put it out to my blog subscriber list of 2,500 people. I woke up to my first $2,000 in online sales.
I quickly realized I didn’t have to go looking for clients in the traditional way. That first year I made my first $103,000 on the internet from a laptop, kind of bouncing between my car and wherever I could find a space to live. Sometimes when you are in dire straits you just don’t even have room for fear. It’s almost like adrenaline takes over.
I remember all of a sudden owing 30 grand here and 50 grand there. It was insane. I saw all this money coming in, but I never really understood the big picture.
I remember getting scared when I started to grow. When you’re not prepared for that growth you have no idea how to leverage it. I didn’t have anyone working for me, so it was really overwhelming. I was making money but none of it was going towards taxes—I hadn’t considered any of those things. I remember all of a sudden owing 30 grand here and 50 grand there. It was insane. I saw all this money coming in, but I never really understood the big picture in a way that was smart and strategic. Like everything else it was unplanned, unorganized. If I could do that again I would just put a little bit of money aside every week and get a bookkeeper early on.
I am really, really bad at planning. You would never know I have anxiety on the outward surface, but there are little tells. Like I’ve invented drama just so I would have an excuse to give myself a break. At least 30 million times I found myself almost to the point of tears because I was feeling really incapable. My suckiness was showing pretty bad. At that point you have just two options: close the business and move on, or hire someone to help you. And that’s exactly what I did.
On the flipside, my superpower is getting inside other people’s heads. I’ve used that skill really well when it comes to creating content—when you understand what someone else is thinking, and speak directly to those thoughts you make people feel seen. They immediately feel excited by the prospect of entering the conversation with you.
I am the poster child for doing things off the cuff before I’m ready, but I think that is one of the reasons I’ve had success. While everyone else is getting ready, I’m getting better. I can’t stress how important that is, especially when you’re an entrepreneur. And things are going to change daily anyway, so why don’t you just get in there and start now?
Disclosure: Ash Ambirge is a Bench customer.
Illustration by John Larigakis.
More stories in this series
- Payal Kadakia, Founder of ClassPass
- Brian Scudamore, CEO of 1-800-GOT-JUNK?
- Chip Wilson, Founder of lululemon
- Charles Chang, Cofounder of Vega
- David Cohen, Cofounder of Techstars
