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Joanne Wilson: The Magic of Dreaming Big

About this talk

The typical mythology of an entrepreneur often involves romantic origin stories of young, single people, burning the candle at both ends. And that was Joanne Wilson’s plan too, until “life got in the way.” However, part of the benefits of starting your own business means building the lifestyle you want to lead. In this talk, investor and entrepreneur Joanne Wilson shares how she launched her own business while life happened. 

Joanne Wilson, Angel Investor & Blogger

Joanne Wilson has had several careers starting out as a buyer at Macys to running a company in the rag trade eventually leading to spearheading sales for a start-up magazine/e-zine/events company called Silicon Alley Reporter. On to the non-profit world where she chaired MOUSE (Making Opportunities in Upgrading Schools in Education) an organization focused on technology in inner-city schools. She has sat on a number of profit and non-profit boards and has been involved with a variety of real estate transactions from beginning to end.

Joanne has been blogging since 1994 under the name Gotham Gal. She is involved with the start-up community as an angel investor and adviser. She has been a champion of women in tech by starting and co-chairing the Women’s Entrepreneurial Festival with the ITP division of NYU. Many of the companies she is working with are owned or started by women.


Full Transcript

So I would like to ask the question how many of you in the audience think of yourselves as an entrepreneur? All right. Now how many of you think of yourselves as an artist?

So today I’m going to talk to you about how do you build a business through the lens of a lifestyle that you want to live. So when I graduated from college, which was many, many years ago, I took my first job at Macy’s training program. And I was under the impression because no one told me otherwise that when I started at Macy’s that within three to four years I would be the president. I would run the company. It would be a multimillion dollar company. And that would be what I’d be doing. I told my husband, no need to worry. I’ll take care of us. I’m going to rule the world. And I got to Macy’s and moved very quickly up the ladder. And I got to of the supreme job you want before you move on to the next which is to be a buyer. And I was then ready for the next which , of course, is my presidency. And a gentleman that I worked for said to me, well, I’m really sorry. Women do not move as quickly as men in this company. And I thought, really? And at that time Macy’s had actually gone for being a publicly traded company to being a privately traded company. And I knew just enough to be dangerous that if I wasn’t going to get stock in that private company, I was out of there. And so I left and I went into wholesale. And I ran a company in the wholesale world. And then life got in the way. And I had these children. And nobody actually told me that when I had children I’d have to be responsible for them, I’d have feed them, I’d have to clothe them, I’d have to make sure they were safe. And so then I began to think, well, I don’t want– I want to be present in my children’s life but I also want to use my brain. So how do I harness those competitive desires that I’ve had since I came out of the womb and then still be able to raise a family? It took me a while to figure that one out. And it was when the internet arrived that it all came together. And I was able to basically run a company and raise a family at the same time as I sat in my basement with my headphones on and I could still go upstairs and bake cookies. My husband was working at the time. I had taken some time off before I went back to the internet business in the mid ’90s. And he was working in a venture capital firm. And in one week’s time as he was really one of the pioneers that was investing in the internet in New York, two venture capital firms approached him and said, why don’t you can be a partner for us? And he didn’t know what to do. Should I go with this firm? Should I go with this firm? And a really good friend of ours came up that weekend and asked the question that I have asked many entrepreneurs that you’ve probably asked yourself which is what do I want? How do I see my life in five years? That’s like the pragmatic question. What do you see your life in the next five years? And when he asked him that question, it all came together. Well I want to start my own– I want to own my own company. I want to run my own company. And so it allowed him to take that path which was how do I get to the end game which is I’m going to run my own company. And so he began his own firm. And so you should ask all of yourselves, what is your end game and how do you get there. Do you ask yourself that pragmatic question, which we always ask yourself, which is where do we see yourself in five years and so what’s that path? Or what’s the dream? Dream is defined as a cherished aspiration, ambition, or idea. So right now I talk about this time that we’re living in as startup nation. It’s a very, very interesting time to start a business. And all across the country we’re seeing businesses that are starting that are small businesses that become large businesses. And it’s making a huge impact on our economy. Yet at the same time there’s a creative boom happening. And there is the desire for people to explore their creative side and with that make their own lifestyle. There are more options now to provide creative people the chance to launch their own business, provide supplemental income for themselves. So you can be an artist and an entrepreneur and create a lifestyle business around your talents, your dreams because there are so many platforms so you can do that on. You can do it on Kickstarter, CircleUp, Behance, See.Me, Indiegogo. There are classes around many of the cities. There are communities to be had where you can meet other people that are trying to figure out their creative side and what they want to do with it for a business. You can be a photographer. You could be a filmmaker. You could make pickles. You can make ice cream. You can make a t-shirt company. You can make a hat company. And as an artist, to see yourself as an entrepreneur essentially takes on a completely different meaning. The definition of an entrepreneur is a person who organizes and operates a business or businesses taking on greater than normal financial risks in order to do so. In my humble opinion, I actually do not believe that entrepreneurship can be taught. But it can be encouraged. Recently I read a piece, I don’t know if any of you saw it, a young woman who was working in a large company decided to take that creative leap. And she wrote this piece. And she used two words to describe what she went through which is should I or must I. Should I be an entrepreneur? Or must I be an entrepreneur? Should I be an artist? Or must I be an artist? And I really do believe that the most successful artists and entrepreneurs believe it is something that they must do. That there is this fire in their belly that they have this desire to chart their own course. Now you can actually embrace the must and you can get up every day and be your creative self because technology has helped us choose the life that we want to live. So the question you need to ask yourself is am I going to ask myself that practical question, which we did, where do we want to be in five years, or the question is what’s the dream. So how do you build a sustainable business around yourself. I believe that career is no longer a word. That we no longer have careers. That the next generation of kids graduating from college So what you’re going to do at 20 is certainly not what you’re going to do at 60. But all those dots will connect and you will learn from each experience as you go through your life. Work has blended into zero personal separation. It is a mixture of how you want to live your life. And work and your brain and your family and everything else you do is mixed into one. So about maybe about a year and a half ago I met this woman who has this life coach company. And she said to me, what’s your dream? And I was like dream? I don’t dream. I don’t need a dream. You know, I can’t. I mean, I’ve got a great life. Like I’ve, you know– I’m very pragmatic. I couldn’t do the things I wanted to do maybe 20 years ago which was open up a restaurant or start a food company. Like I’m too old for that. I’m not going to do that. I know how many hours goes into that thing. No dreaming for me. And that concept of dream kept floating around in my head for the last year and a half. What would happen if I dreamt big? Would it be like that entrepreneur taking that leap of faith into the unknown? And what was holding me back? Was I missing something? I figured out how to balance my brain and my life a long time ago. And then I kept thinking, well if I could dream and what would happen if my wildest dreams were to come true? So I do ask entrepreneurs that same question that was asked to my husband years ago which is where do you see yourself in five years because I do think it helps you plot out the course of your life. And then about a couple months ago I got the dream. And a young entrepreneur that I invested in who has a really interesting product which has a social mission she has had a very rocky road. And I think a lot of people when they become entrepreneurs they don’t say to themselves, wow, now that I have this product and this company and it’s taking off, I have to go raise money. I have to create a culture. I have to hire people that are smarter than me. I have to create a work org chart. I have to think out of the weeds. I have to never sleep. And I don’t think she really thought about those things. And all of a sudden this business took off. And instead of really thinking about who she was going to hire, she hired a bunch of people to plug in holes to keep everything going without asking for any advice. And eventually the boat started to sink. I’ve never counted her out because she’s insanely scrappy. And she sort of has rebooted and figured out now what she is doing with her business. And she came to see me about a couple months ago. And she told me what was going on. And we talked about where was her business going. And she always had this insane connection with the consumers. She really want to sell this product directly to consumers. But the reality is that if she sold that product to businesses and created a business to business it could be a really big business. And she had a hard time wrapping her head around which one, which one. And I said to her, it’s your dream. You’re the entrepreneur. I would never tell an entrepreneur, this is what you have to do. What’s your dream? Do you see yourself just selling this product and talking to consumers? Or do you see yourself growing this huge business? You need to figure it out. And then about a month and a half after that, I’m involved with a group of people we do this founders breakfast which is super cool because as investors we sort of know all the founders but the founders don’t know each other. And so we get together. And we have this breakfast roundtable and founders can talk about sort of that echo chamber in their own head and what they’re going through. And so they can connect with other people. And this particular event took place at the stock exchange. I’ve never been down to the stock exchange before and it is a total Americana experience. And so we went down there after breakfast. And of course I had this vision like trading places. There’d be paper being thrown everywhere. It’d be crazy. And it’s actually very calm. It’s all computerized. And one of the women I invited to come who was an entrepreneur I’m invested in, she turned to me and she said, you see that bell? That’s my dream. I’m going to ring that bell. And I thought, oh my God. I get it. I get what meant in terms of dreaming big. And so as creative people, you all have a gift. I wish I had that gift. I always wished, I wish I could paint or I could sing. And those talents allow you the opportunity to dream about how you want to get up every day and what do you want to do because of those talents. The ability to dream about your creative desires and match them with the life dream is the road to getting up every day and being able to live the life that you want to live. So I would say don’t be afraid to dream. It does not mean you should quit your day job. It doesn’t mean that there will be major fears. It certainly doesn’t mean that it will be financially scary. It doesn’t mean there won’t be internal struggles. It doesn’t mean there will be a huge divide from what really happens and actually having that dream be met. But dreaming sets yourself in motion to go down the path because you chose that road.

So choose the road that works for you so that you get up every day and you can make your passion your livelihood. That is empowering. So I leave you with the advice which is dream big, dream small, but dream. Thank you. [MUSIC PLAYING]

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