8 Startup Lessons You Could Learn From Gotham Gal

It’s easy to think that the wife of a well-known and successful VC (Fred Wilson) would have had an easy and storied life of wealth and privilege. I had previously had the opportunity to spend time with Joanne Wilson, Fred’s wife, and knew otherwise.

That’s why I was so interested in having “The Gotham Gal” come on This Week in VC (video link on YouTube, download iTunes, episode 15) and dispel those myths. In fact, as she tells it, in their early career when Fred was young in VC, Joanne was earning 3x more money. Well into their 30′s “they were living paycheck-to-paycheck” as Joanne had taken time off of work to raise three children.

After college Joanne worked for four years in retail apparel at Macy’s where she initially managed sales reps on the floor and then worked as a buyer of clothing. After four years of retail she went to “the other side of the business” working for a clothing brand where she sold apparel to department stores and other companies. This is where she first developed sales skills.

She doubled her salary by going into sales. Then after a year she got into the business side and learned how to manufacture, what the margins of the business were, etc.  She left there to join a man running a clothing brand. She came in and took over the business. In 18 months from $1.5m to $12m in sales. She did this because she had great rapport with buyers. She knew their business needs because she had been on both sides of the business.

Below is a nice summary of our interview with some great quotes from Joanne. I think this video should serve as an inspiration to any young aspiring female entrepreneur (and male!) and is worth watching when you have a few moments.

But for everybody else, where are 6 things you could learn from Joanne Wilson:

Sales: until about minute 20

1. Get out of your comfort zone – don’t just work on the things you know how to do or like doing “People tend to gravitate toward areas that they know. Totally get outside your comfort zone. Put yourself in a position to learn things you don’t know” We talked about this in the context of management (in retail her motto was, “get away from the cosmetics department. You already know that”), in sales and more broadly as an entrepreneur.

2. To be effective at sales you need to really understand the business of the person who will buy your product. “[I was effective at sales because] I understood their business. Most people who worked in the business didn’t know how to make a profit & loss. I provided information for my customers to make their lives easier.” Really understanding the business of your customer matters. It’s the key to growing a successful business and is a theme the Steve Blank plays up a lot. I agree whole heartedly. The other money quote she gave that I loved was, “”Totally get out of your office.” Sounds kind of obvious. Not enough entrepreneurs dedicate enough of their day to this.

3. In sales you also need to establish rapport, ask insightful questions & then shut your mouth! “A lot of sales is innate. A really good sales person can get people excited and get people to tell you information they won’t tell other people. Build rapport in whatever way you can. Who knows, it could be fishing or whatever.  Say very little. The less you say, the more the person on the other side gives you back. As a sales person, just ask the right questions and you’ll get the answers you need.”

4. Be a mensch – the world is small than you think and bad karma will catch up to you “We’re in a very small community. Life is too short to be a dick.” There’s no reason to be nasty to your competitors or mud sling. There’s no need to bad-mouth other people. It’s surprising how small the tech community is and the older you get the more you realise how much people from earlier in your life have a way of coming back into it. Be a mensch.

On being a woman, becoming a mum and forming a sense of identity [20-45 ]

5. For women – “Don’t get off the train completely when you have children. You need to keep your skills. You need to keep your database in terms of connections and the people you know. You need to keep your relationships up.”

“When I stopped working it was quite a shock to our system. Even if you continue working, you’re still responsible for [your kids well being]. I didn’t think about who was going to put food in the refrigerator.”

“The Internet saved my life. I needed something to find my own identity.” She went to work running sales for Jason Calacanis at Silicon Alley Reporter (mid 90′s). The Internet really re-connected Joanne with her former working self.

Invested in “Catchafire,” which is a business that helps people (mostly women) connect with pro bono opportunities where they can put their skills to use. Take a little break but keep your skills fresh.

“There are so many places you can go on the Net where you can find your community. I would tell women to find them.”

6. The current generation of college students want to be entrepreneurs more than rock stars – “This next generation is going to be very interesting. After seeing “The Social Network” there is an increased attitude amongst this generation (of women) that … why not go into startups? They all want to be entrepreneurs – they don’t want to be rock stars.”

7. To run an effective business it’s really important to hire women in your company & as advisors – “Men tend to pump up their chests more (than women). I think it’s really important (to hire women). Women take a look at things differently. They understand things differently. Make sure they’re on your board, your board of advisors, whatever. Make sure 50% of the people you hire are women. The women are out there.

Certainly if you look at eCommerce & social media – women are the ones using these products. What better to have on your team than someone who understands this at a fundamental level.”

8. Women need to start becoming entrepreneurs at a younger age – “Don’t go to work for big companies, don’t get an MBA, go to work for a startup and start on this path. Start early. In the next generation everybody (including women (are going to write code).”

“The majority of businesses that I’ve been investing in lately are ‘women businesses.’

You can watch it all on YouTube or download from iTunes for free.