Joanne Wilson on women CEO’s, careers, and angel investing

Rohan: Today’s ‘Real Leader’ interview is a very very special one. Regulars here need no introduction to Joanne Wilson. I’ve mentioned her and her cool blog more times than I can count. I started becoming a regular reader on her blog thanks to an interview she’d done with Mark Suster ages ago. And it’s thanks to her blog that I became a religious regular on Fred’s blog and that’s been an incredible learning experience as well.

So, in short, I was greatly looking forward to connecting with her and I was really hoping that she would say ‘Yes’ to an interview request for this ‘Real Leaders’ feature and she did. I am so glad! And I could barely conceal my excitement during the call. We had a fantastic 25 minutes where I fired a volley of questions and her answers were full of insight, energy and optimism.

Excitement aside. It’s time to move to the interview.

About Joanne

12Joanne Wilson a.k.a The Gotham Gal has had many careers – buyer at Macy’s, spearheaded sales at start-ups, dabbled in many business like e-zines and even housing, chaired not-for-profits etc. She is currently an angel investor in NYC.

But, first and foremost, Joanne’s most important job is being a Mom to 3 terrific kids. Her best friend is her husband, Fred – another role model investor and blogger, who I hope to interview soon as well. She has a range of interests including food, travel, art and theater. Do click here for more on Joanne.

Interview transcript


Rohan: How would you describe your story/path?

Joanne: I’ve had many many careers. I actually think the next generation will have many many careers. No one will stick with one company for thirty years. Leaving the first company was, of course, the hardest thing. But, once you leave and realize you can get a new job somewhere else, it’s kind of empowering. And you say to yourself – if this doesn’t work out, I can go somewhere else!

I’ve been in a variety of verticals because it just ended up happening that way. I’ve been in retail, in wholesale, in the beginnings of the internet, in sales, in helping grow companies and really came back with all of the knowledge I had and the career I’ve had including raising a family and building homes to investing in companies and help entrepreneurs navigate the world as they grow their companies.

And I like it because I like helping people succeed in their dreams and it’s fun to have a bunch of things all going on at the same time and being involved in a little bit of every one of them, which I really enjoy.

And I learn every day, which is great!


Rohan: What were your motivations to move across so many verticals?

Joanne: At the beginning, it was just sparked by interest. I got a job out of college in Macy’s training program as I wanted a job in retail. And then the company changed and went private and they weren’t exactly handing out stock options, it didn’t make sense for me to be there. It was basically stock at the top and ‘we’re going to make you work twice as hard’ below. At that point, Fred had just started becoming a venture capitalist and I knew enough to know that continuing was not smart.

And, so, I jumped ship. That was more evolution (of thinking). All of the decisions I made in the post was definitely family oriented.


Rohan: What is it that drives you/ inspires you/ gives you energy when you wake up in the morning?

Joanne: I think I’m really inspired by the entrepreneurs I get to meet every day. It’s Malcolm Gladwell’s 10,000 hour rule in practice.

Tomorrow is a perfect example. I have a meeting at 10, 11, 1, 2, 3, 4 and 5. I’m going to see 7 businesses tomorrow. If you see enough of this stuff, then you can see the whole landscape and see what’s happening, where the economy is going, what kind of business people are getting into, who’s good, who’s not good, what makes sense and what doesn’t. At least from my perspective. It doesn’t mean that I’m right but from an intelligence point of view, it’s gratifying.

You know, I’m not sitting around making cookies all day, though I do that many times too. It’s intellectually stimulating.


Rohan: What relationship do you have with all these entrepreneurs? Is it as an angel investor or is it different at times?

Joanne: There’s many of them that I’m friendly with where if they wanted to pick my brain or have a coffee with me, I’d be happy to do it. But, the majority of them that I end up with ask questions like -’Can you be my mentor? Would you get involved? I would love to see you once a month.’ For the majority of those, I decide whether to invest or not. And I invest at the very very beginning – not the seed round, but the angel round. And then I spend a lot of time with these people.

I’m not the one that says – ‘okay, we need to talk, we haven’t talked in a week’. But I’m always available. If I had an entrepreneur that called me every single day or shot me an email every day with questions, I would call them, I would get back to them, I would help them. If I don’t have the answer, I would find out the answer, if they need to know something that I don’t know, then I’ll find someone in my rolodex who can help.

So, generally, I end up becoming involved in these companies.


Rohan: What has been the most defining moment of your life? Or a couple of defining moments?

Joanne: Well, I think having kids is pretty defining! And, each time I was able to get into a new business. People say, ‘oh my god I have been home and haven’t worked for 10 years. I don’t know what to do’ , particularly women. But, I’ve seen these women go to meet ups and before they know it, they’re in the industry. They know what’s going on, they know the people. They’ve either started companies or work in the company.
That’s pretty empowering.

Having my childern is the most defning momement. I’ve known my husband since I was 19 yrs old. So,that was more of an evolution that started met him in college and continued in to life.

There was a point when we were forced to live in the suburbs due to financial difficulty and that was definitely not the place for me.
Things changed and we were able to move back to the city and that was a major defining moment for us.

(I didn’t ask questions here but, in retrospect, I realized I’d read about this earlier in Mark’s blog. For more context, please do check this interview out)


Rohan: Having read your blog, I know that woman entrepreneurship is a topic close to your heart. Could you tell us more?

Joanne: I think its very important for women to be entrepreneurs for a variety of reasons. First of all, we always hear that there aren’t enough women in corporate offices at the top level, not enough women CEOs, not enough women in technology, not enough on boards of directors etc.

Let’s say I find 100 women entrepreneurs, now we have a 100 women CEOs. So you can change that.

Second is that women have childern. They are the only ones who can! There is more of a partnership in the last couple of generations be it picking up groceries or changing diapers but at the end of the day
women speak in terms of we, men speak in terms of I. Women have this innate nurturing quality. If you can be a woman entrepreneur at any level, its empowering for your children, particularly for your daughters to see that you can figure out how to balance your life.

And if you run the company, you run the show! If you need to go home, go to a basketball game, take a 2 week vacation or be home with your kids, no one is telling you “You cant do that because you dont have 2 weeks vacation”.

I’d like to see all women be entrepreneurs, be it from doing a startup that becomes a multibillion dollar company to a 20 million dollar company or a bakery down the street. I think its better for the economy, for the families and for the community.


Rohan: The US is going through a tough time. (And, of course, Europe looks to be in deep deep trouble!) In many ways, the world still looks to the US when it comes to entrepreneurship. Do you think , these frequent ups and downs in the economy have changed what entrepreneurship means?

Joanne: I think the youngest entrepreneurs, ones younger than 30 are looking at their parents and saying “My Dad worked for that company for 30 years and then they laid him off”. I think many people in the new generation are saying it isn’t all about financial success. Of course, you have to put a roof over your head and food on your table, but its also about happiness. And about what am I am passionate about, what I want to do and how I an going to create my own life. And then you read about all these startups, you see the “Social Network” movie and you say. “Hey you know what,I can do that”.

But I think the caveat here is that when people are funding all of these companies, they are not really hand holding them. Many of these companies need to stand back and say ,”I’ve been acknowledged and given money to start something up, I can make a 3 million dollar company.” or “This business is exploding. This could be a 50 million dollar company”

There are all these different levels, and that is something that is going to get flushed out. Everyone who has a business right now thinks they have and want a multi billion dollar business. Maybe that will change a bit. If you are an entrepreneur and you love what you’re doing and can pay for your lifestyle, get up every morning and feel passionate about it what else could you ask for?


Rohan: How do you manage yourself and your energy? Any tips and tricks that you may have for us would be great.

Joanne: I don’t have an assistant. I do everything myself from the meetings with entrepreneurs to the evening outings to dinner parties to my children to managing my house, I’m in the middle of 2 major construction projects right now.

This works because I’m extremely organized and I keep lists. I get things done as soon as they come to my desk. One example is with my calendar. One of the reasons my calendar works is because if I email you today and say, ‘lets meet how about Nov 9 at 2 pm’, it goes into my calendar right then.

So, even if it takes 3 days for you to get back to me, you are already on the calendar. And that’s settled.

If I have 2 days in a week that I spend on personal time or real estate projects, they are blocked out on my calendar. I try to work only 1 night between Mon and Thu, although that doesn’t always happen.

And well, at times, it doesn’t all work as per plan. I had a conference call on Thursday afternoon at 5 pm while I was making dinner. Sometimes, that’s what you have to do!


Rohan: What would your message be to all readers – especially give they would like to be leaders – if not leaders of companies and communities, definitely leaders of their own families.

Joanne: I’ve always said this even when people worked for me when I was 22 , follow your heart. If you get up every morning for 2 weeks at a job and you think “This is the worst”, move!

You have to be happy and healthy. Life is too short. There is no reason to be in bad relationships, in bad jobs. It’s up to you.

If more people grabbed opportunities and  rocked their boat on a daily basis, it would be a much better world.

Firstly, credit to a close friend of mine and RealAcader, Snigdha, for helping with most of the transcription while taking some time off her holiday in Singapore (Id Mubarak to everyone!). Thanks Snigdha!

Overall, this 25 minute phone call was fantastic. I was full of energy and possibilities right after and we have Joanne to thank for that.

A couple of things stood out – the calendar suggestion as an immediate next step that I went about implementing for a bunch of calls that were being scheduled.

But, the line that inspired me most was the  ’Let’s say I find 100 women entrepreneurs, now we have a 100 women CEOs. So you can change that.’

I’ve blogged a lot about the butterfly effect i.e. the massive potential effect of our positive actions on the world, of working within our circle of influence and making a difference in this world one day at a time. But, that line summed it all up. Every day we get better. And every day we change the world, one way or the other.

Thanks Joanne.

Real Leaders Team