128 From Paycheck to Passive Income: Reinvention, Networking and Investing with Entrepreneur and Tech Influencer J Kelly Hoey

J Kelly Hoey is a former attorney turned early stage investor, technology influencer and author of a great new book, Build Your Dream Network. Her storied career is one of transformation, and can only be explained by her unique ability to tap into networks and make valuable connections. Learn how to leverage your expertise, your networks and your finances to build a lucrative passive income.

Melinda Wittstock:         Kelly, welcome to Wings.

J Kelly Hoey: Thank you for having me. This is awesome.

Melinda Wittstock:         I’m so looking forward to this interview, because a lot of people are afraid to embrace change in their lives. And, you are the queen of change. I mean, you have transformed in so many ways and profitable ways. So, tell me, how did you first make that transition from being a lawyer into being an author and an investor?

J Kelly Hoey: I’m laughing because as a lawyer, a Virgo, and a Canadian, things we don’t embrace, like big, dramatic change. And yeah, my life is now a whole lot of change a lot of the time. I think you set yourself up for it in terms of being able to navigate and weather change, and to be able to kind of … I don’t want to say, “Dive in.” I think more like surfing, kind of the surfer legs to have to be able to successfully, as I said, weather it. But for me, it’s always three things I think about, which is, what do you know one for? What’s your knowledge base? What’s your expertise?

Whether you’re an investor or you’re an entrepreneur, having that domain knowledge, and not just being the wrap-yourself-in-social-media. Any of us in this digital age can say, “We’re an expert.” But really, having the knowledge base and investing in your knowledge base, investing in your expertise. Then I think the second thing, with respect to change, is you got to have a network and a diverse one, because that’s how we are able to tap into opportunities. Or if one door closes, we know we’ve got another one that can open up for us.

And then the third piece is, you know, the financial one or the financial equivalent. The … as I always say … build your expertise, build your network and then build your bank account. No one is going to fuel your dreams. That’s something that you need to fuel yourself and put that investment in. So, are you banking on yourself? Are you creating your yes-me fund? And are you creating a yes-me fund in the sense that, will other people want to help you? So, you may not be able to code your website, but you may be able to babysit the kids of somebody who can. Like, where can you barter or exchange, and that I think plays off the network piece.

When I think about my own crazy career kind of changes and things that I decided to do, when I had set my eyes and my heart on that future thing I wanted to do, it was those other pieces that really enabled that transition to happen.

Melinda Wittstock:         That’s beautiful. I love where you say, “The yes-me fund,” because all too often I think woman are so busy investing in other people. They forget to invest in themselves. What does your yes-me fund look like?

J Kelly Hoey: If we just look at it in a financial sense, we can always look at the, “Okay. You got to save for your retirement.” You know, that kind of stuff. “Do you have your 401(k),” and et cetera, et cetera. But there was too many people … This is from when I was in law firm management. It was too many lawyers who I knew who felt that they were shackled to a job because of the paycheck. They couldn’t go and pursue what they wanted to or what they loved because they had built up a lifestyle, or they just became so wedded to what they were taking in every month, rather than saying, “This is what I need to live, and everything else I can bank, and then that gives me freedom.”

You know what I mean? I remember people saying to me, “Oh I’d love to do that job, but it doesn’t pay enough.” Well what happens if you actually had saved and had that cushion so you could take a pay cut? What happens if you could speak up at the office without fear of being fired, because you knew you had the rent for the next three or four months in the bank? So, there’s an element of a yes-me fund that I think is purely, like dollars in the bank. Then the other piece of it, I think of it in the sense of someone saying, “Gee, I’d love to start my own company, but I can’t afford a web designer.”

Well you know what? Maybe you have a web designer in your network who says, “Well I really need someone to babysit my kids for a few weekends. Why don’t I exchange you that?” Or you think of the person who may say, “Oh you want to start your own company? Well, come and work out of my office.” It’s like, “Where have you been there for somebody else that they will help you create that barter or exchange yes-me fund.”

Melinda Wittstock:         This is so interesting because it really comes down to mindset on this podcast. At the end of the day, it always comes down. It’s like what’s in your head and how you perceive these things. So if you automatically think you can’t, you’ll be right. If you think you can, you’ll be right. It’s that old Henry Ford quote, right?

J Kelly Hoey: Right, right. That’s exactly it. I think some of the stuff on money, I really did get from my ex who was able to walk away and maintain the values and the way things he thought should be run. It rubbed against people that guess the wrong way when it was working on Wall Street. But to be able to walk away and say, “Hey, I didn’t make managing director, but my lifestyle didn’t change.” Not a bad thing at all. And so, some of this, I think, for people who have the privilege of being in very high paying jobs, it’s like, “Bank it.” Banking it is like … That gives you so many more choices and freedom than ratcheting up a lifestyle every time you get a bonus, or you know, “I’m not taking your pay.”

And the ability to walk away, like when I got to that point, the ability to walk away was huge. That was huge. That’s like the transformative.

Melinda Wittstock:         That’s power in a lot of ways, because if you’re really stuck in a scarcity mode and in desperation, and you really, really need something, I don’t know. I believe whenever I’ve fallen into that trap in my life, for what it’s worth, you just don’t make decisions. They’re not necessarily the right decisions. They’re not really in alignment with why you’re here on the planet, right?

J Kelly Hoey: Yeah, yeah.

Melinda Wittstock:         I mean, they’re very short term. They’re made in fear. I think every in every single decision that I’ve ever made that was based in fear came back to haunt me. You live long enough, like you start to get that. And so, I think it’s so smart what you’re saying about, like create the circumstances, where you can be in abundance and really stand a chance of really getting in alignment with what actually makes your heart sing, right?

J Kelly Hoey: Right.

Melinda Wittstock:         You get them to walk away, all of that stuff. That’s awesome. So, the me fund. When you think of a me fund, and tying that to the first part of your equation here about expertise, do women invest enough or maybe even on … Actually, I don’t even know if I want to ask the question this way. I was going to say, “Do we invest enough in our learning, in our credentials, in our networks and all of that?” And then I thought, “Well maybe, sometimes, we get over-credentialed.”

J Kelly Hoey: Over-credentialed. There might be that element of over-credentialed. But yeah, you know what? Maybe it’s over-credentialed in the sense that, we don’t put our credentials into practice. In the sense that, you know, you could learn endlessly about cyber security or Bitcoin and maybe never ever completely grasp the entirety of the subject matter. But when at what point are you taking what knowledge you have and sharing it with the world? Like, sharing your point of view, putting it out there that you care about, know about, think about, have a point of view on this subject. I think more of that with women versus we educate ourselves too much, or we think we need one more course. When are we owning the space that we know this?

Melinda Wittstock:         Yeah. The interesting thing about the credentialing or just the, “Oh I need one more thing.” It’s sort of a perfectionism. It’s a procrastination in a way, whereas a lot of dudes in the entrepreneurial space will just roll up their sleeves and declare themselves to know what they’re doing. I think women are less, less likely to do that.

J Kelly Hoey: Yeah, yeah. It’s like you see a job and then it has 10 specifications. Hey, we want these 10 requirements, and women, you know, if we don’t meet nine out of the 10, we won’t apply. I think that applies, and I think that has some parallel to what we’re talking about, like when do you have enough experience? When do you have enough knowledge to put up your hand and voice your opinion? And, I think that’s where when I think about the expertise. I encourage people to be lifelong learners. I think the curiosity, judgment, analytical thinking, reasoning, you know, that’s not going to get chased away by AI.

If it is, then it’s like HAL in 2001, in Space Odyssey, and we should really all be freaking worried.

Melinda Wittstock:         Right, exactly. Someone still has to make the artificial intelligence. In a way, it could be … It’s a wonderful question here, because it could be immensely freeing for us, to really live the lives that we’re meant to do because the artificial intelligence can take away all the drudge work.

J Kelly Hoey: Right.

Melinda Wittstock:         That could be an awesome outcome, yeah, or it could be HAL.

J Kelly Hoey: But then you’ve got expertise, like put it out there. At some point, I think, when people aren’t sharing their knowledge, they have to look in the mirror and say, “Okay, what’s the real question? The real issue here is not that I’m not the expert. I’m not sharing it. Why am I not doing that?”

Melinda Wittstock:         It’s fear of failure, or it’s fear of success.

J Kelly Hoey: Yeah. I had that question asked to me once. It was really … It was hilarious because … You know what? I’ll find the video and personally send it to you, because I think I know where it is. The interviewer said, “What are you most afraid of?” I looked at her, and I said, “Success.” And then we both look at each other, and it was like, “Oh my God. Where did that come from?”

Melinda Wittstock:         Right. So, where does that come from? I think I’ve had that off and on where you get really close to succeeding, and then, suddenly, you’re there and you’re like, “Oh well, no.” Maybe something some limiting belief tells you, “Oh maybe you don’t quite deserve it, or you don’t quite belong in that room, or you shouldn’t … ” Right?

J Kelly Hoey: Yeah.

Melinda Wittstock:         It’s some strange inner thing, and often I think we’re not even conscious of it. We don’t even know that we’re, in effect, sabotaging ourselves. So, why are we afraid of success? What’s that about?

J Kelly Hoey: Oh my God. That’s probably not enough hours in the day and alcohol for me to analyze.

Melinda Wittstock:         That’s a run for that one.

J Kelly Hoey: Oh my Lord. There’s something Freudian or weird or whatever else. And then, a lot of the times, when I’ve been doing some mentoring work with entrepreneurs, from other countries, depending on the part of the world you come from, there’s very much a … you know, the tall poppy syndrome, like one of the flowers gets bigger than anybody else and everybody else like goes over and cuts it down. So there could be gender issues. There could be cultural. There could be socioeconomic, all sorts of stuff that that tie in on that. Other than probably heterosexual males over six feet tall … I mean, probably everyone suffers from it at some point and that it’s … I don’t know.

I guess what I’m … on this podcast, and you and I having this conversation, my attitude is to the women listening, get over it ladies.

Melinda Wittstock:         Yeah. Oh my God. I agree. It’s interesting though that there’s still some research that suggests that, say, a man who’s very successful, is really admired by other men and women for being successful. Everybody looks up at like Elon Musk or like Richard Branson or … I’m thinking of entrepreneurial examples. In women’s case, I think it is changing, but other women are more like, “Who does she think she is?” Right?

J Kelly Hoey: Right.

Melinda Wittstock:         And man … and then, like I don’t know about you, but I remember my mom telling me way, way back, like just completely of another generation. “Oh Melinda, be careful because men don’t like strong women.” And now, into your mind and you think, “Oh well, to be successful as an entrepreneur, I’ve got to be strong.”

J Kelly Hoey: Well no, you have to be successful but not too successful. It’s like, “Oh for the love of God.”

Melinda Wittstock:         Right.

J Kelly Hoey: Well one of the things people will say to me is like, “Kelly, when are you going to stop working?” I’m like, “Never. This is my golf. This is my hobby. Don’t ask me what my hobby is. This is my hobby. I love what I do, and I love the opportunity to change and do different things. I can’t imagine a day where I’m not sort of going to the office,” and then I think about it. So, my answer to the question now when someone says to me, “When are you going to start working?” I say, “The same age as Warren Buffett or Charlie Munger, whoever stops working at the older age. That’s when I’m going to stop,” because no one questions.

In fact, Warren Buffett and Charlie Munger go to the office every day. Now, change the gender. Would we be saying the same thing? We would be like, “That old bat, is she going to stop …?”

Melinda Wittstock:         Yeah, but here’s the thing. The reason why you’re going to … It’s not work for you. The reason it’s not for you, and you can tell just in your voice and just the energy that you give off. You love what you do because it’s like your vocation. You’re in alignment with it. It’s your passion and your purpose and mission. You know, all of those things.

J Kelly Hoey: And now, it’s a mission also, so that when I think of Charlie Munger’s well into his 90s, I’m like, when I’m well into my 90s and I’m still excited about what I’m doing, I want people to see a professional who is excited about what she’s doing and not going, “Oh that crazy, old bat. Get off the podcast and go away.”

Melinda Wittstock:         Yeah, but you know what? It’s really engage … I think it’s so uplifting when you see somebody who’s really just in alignment and enjoy, in fact, in what they’re doing. If there’s an electricity about it, it attracts like. It attracts more people like you, right? So in your life, have you noticed, as you made this transition, were there more people that came into your life that were more positive or more in alignment with you? Did they just start appearing and other people falling off?

J Kelly Hoey: Yeah. I would say that absolutely is the case. I mean, it’s probably part of the reason why I wrote the book, and why I am enthusiastic to go anywhere and everywhere and talk about it, is I finally feel, now, at age 52, soon to be 53, that I’m having the career my graduating-from-law-school self wanted. The frustrations that I felt in those earlier ages, like why wouldn’t things happen fast enough? I’m realizing, you know what? Things happen when they should. Some of us may have success in our 20s, and some of us may have success in our 30s, and you know what? Some of us may have our success later in life.

The more that you’re paying attention to what is, like as you said, what’s your passion? What is it that you are enthusiastic about? What are the skillsets you need to learn? What is the network that you want to have around you as you look ahead of where you want to take your career? Rather than keeping up with the Jones’ paranoia with everyone else around you, you will move forward, I believe, in your career and get to where you’re supposed to be. And yeah, it’s kind of … I’m like laughing. Forbes wrote a piece, and they listed some up-and-comers, and I was 48 at the time. I just thought it was like really kind of funny. Me and a couple of 20 year olds.

Melinda Wittstock:         But I think you’re really on to something, because I’m also in my early 50s, and there’s a certain point where you just don’t give a crap anymore, right?

J Kelly Hoey: Right.

Melinda Wittstock:         It’s a wonderful time because you still have like tremendous energy. I think women get very … Yeah. It’s like just a different attitude change where all the different pieces start to fit, all the puzzle pieces fit, and I just feel great. I feel just so much more empowered and just in alignment with myself and all of that. I see that around me as well. I see women in entrepreneurship, in particular, crushing it in their 50s.

J Kelly Hoey: But I think if I’d had the perspective that I have now, I think I would have enjoyed a lot more of my career at the earlier part, as opposed to feeling at times frustrated with it.

Melinda Wittstock:         Were you in a rush in the early part?

J Kelly Hoey: You know what? I think it was more of, why weren’t things happening? I was doing all the right things.

Melinda Wittstock:         Thank God I had that.

J Kelly Hoey: And why wasn’t it happening as opposed to saying, “No. Maybe this is the lesson for this part of my career.” This is what I’m supposed to learn and take away from this part of my career. Okay, now, like paying attention now, you’re supposed to go off and do something else. So I’ve had that benefit of hindsight without my career being completely over to go, “Oh that’s what the lesson was.” Instead, I can see it. It’s not so removed. I could share those lessons with other people, but at the same time, I can apply them myself.

Melinda Wittstock:         Yes, yes. Oh my goodness. This is so true. I mean, it is funny when you go … because like a reinvention, I love this whole aspect of change. You and I have a lot in common, okay? So we’re both from Toronto. I mean, because I know you practice law there, right? You were born in Toronto?

J Kelly Hoey: No, no. I was born in Victoria, British Columbia.

Melinda Wittstock:         Oh-

J Kelly Hoey: Woohoo. The pretty part of the country.

Melinda Wittstock:         … we’re both Canadian [crosstalk 00:19:47]. Okay. Victoria is a beautiful place, like near to Vancouver. I love it. It’s gorgeous. I am from Toronto.

J Kelly Hoey: I love Toronto. I love Toronto.

Melinda Wittstock:         It is a great city. It’s gotten much more interesting. It’s just phenomenal. I was there just only a couple of weeks ago, and oh God. It’s a beautiful place. But I’ve been all these different things in my … I think my first entrepreneurial experience was age five when I went door to door, like knocking on doors, demanding people prepay for this show. I was putting on … My black lab was my enforcer, and I made all this money. I made like $100. That’s just a phenomenal thing. I’ve gone through … I’ve been a journalist. I’ve been a television anchor. I’ve had all kinds of different sorts of businesses. I’ve done all kinds of things in my life.

One of the things that I’ve always found exciting actually is change, that it’s like, in fact, the only thing you can take for granted. So, you may as well embrace it, and that’s just like an attitude. I love that, because that way, I live a life and I’m like never bored. I’m always surprised. It’s like it’s a whole life of exercise and avoiding boredom. And so, but a lot of people … I’m always surprised that a lot of people are mortified by change.

J Kelly Hoey: I’m laughing because … I mean, Victoria, British Columbia. Yes, beautiful. I say, “The pretty part of the country,” because I met someone … Why am I [inaudible 00:21:20]? I met Malcolm Gladwell. It was Malcolm Gladwell, and he said, “Oh you’re from Victoria. You’re from the pretty part of the country.” And so, his words, and I just like … It just still cracked me up. Then people say to me, “Oh my God. Victoria is so beautiful. How could you leave?” I’m like, “Newlyweds and nearly-deads.” It’s like, Victoria changing is like glaciers moving. It’s resistant to change. So, it’s really interesting that both of us have … being Canadians and being female, we could say, “Okay, there’s reasons to be maybe sort of cautious of change.”

And then you would layer on my being a lawyer. But Victoria was not necessarily an environment why I’d say, growing up, you embraced change, because the city, the community doesn’t like change.

Melinda Wittstock:         Right. Well Toronto was a bit like that then. I think it’s different now, but I immediately took off. I mean, I went to London, England. I was there for years.

J Kelly Hoey: Rebel. Rebel, you-

Melinda Wittstock:         Yeah. And then, New York. So, it had to be some other place where I could continue to reinvent. And of course, entrepreneurship is constant reinvention, and in a way, it’s … Oh goodness. I keep making this joke all the time on the podcast. So, forgive me. Everyone listening here right now has heard me say this so many times before. But if you want a good therapist, become an entrepreneur, because you will be surely tested. There’s so many things that you can’t control that are beyond your control. All you can really control is yourself and how you show up in those moments.

J Kelly Hoey: Right, and change is the only constant. You’re absolutely right. I think there was an element with, I want to say, those of us who had jobs and went to an office. We were in some ways, in some industries, you were shielded from change. The fact of the matter is with technology, now, all of us need to be entrepreneurial in how we think about our lives, because our only constant right now is change, and our only constant is our attitude and our preparation for taking on that change.

Melinda Wittstock:         Well this brings me to your book, because I think your success in navigating all this change is really in the title of your book, Build Your Dream Network, and something you said in your very first answer at the top of the podcast, which is that when you have a network, especially if you have a number of different networks that overlap in some Venn diagram-y kind of way, you’re going to be spotting all sorts of opportunity, right?

J Kelly Hoey: Mm-hmm (affirmative), or different networks are going to spot opportunity in you or see opportunities for you. I mean, a prime example of that for me was when Janet Hanson offered me the role of president of her global business networking group, 85 Broads. I wasn’t looking for a job.

Melinda Wittstock:         That’s a great name by the way. I love that name, 85 Broads.

J Kelly Hoey: Yeah, so, it started out as an informal alumni group out of Goldman Sachs. It was tongue-in-cheek on their old headquarters address, which was 85 Broad Street. I was very involved in that network, because, at the time, I was building an alumni network for a global law firm, and I was given no resources. I had no staff and no budget. Talk about when your entrepreneur career hits … it sort of goes into overdrive when you’re already employed and you’re given a huge task and told, “Make it happen,” and you’re like, “Yeah, but how am I going to do that?” So I was looking for examples of ways I could build community that didn’t rely on the usual enticements, because I didn’t have them.

I was also thinking, “Oh if I have no resources now, even if they give me resources to continue this program, at some point, there will be no resources again. How can I make something sustainable that does not require a big budget or cash? How can I make something that is living and breathing and has momentum, without any resources?” And that’s when I got involved with 85 Broad, because that it was a voluntary community that started off in that same kind of way. Janet started it because she’s like, “We should do something for all these women who have left Goldman Sachs,” and Goldman wasn’t doing anything.

The enthusiasm of the membership drove that from being 100 or 200 people at a party to when she ultimately sold the network, to being like 35,000 members globally. And so, in my study of that, I dove fully and engaged in this network, and that was both to get a job done. It was a realization for me of like, “Okay. This is really … ” You know, you sort of hear about in theory what’s powerful. But your talents, being exposed to new people, who see something more in you than you saw in yourself five minutes earlier. And as I share in the book, it was like an hour-long phone call with Janet.

She called me at the office, and she wanted to know who I was, because I was asking interesting questions, as a member of 85 Broads. At the end of an hour-long phone call, she offered me a role that had previously never existed.

Melinda Wittstock:         Oh, that’s wonderful. You see, it’s so interesting. I want to do my meditation in the morning now. I finally arrived at this thing, where rather than being willful about it, I just say, “Hey well, I help you to see and spot not only inspiration, like help me to be inspired today, but help me to spot opportunity,” or just be in a situation when it’s there because it’s all around you all the time. It’s just like, the question is, you don’t necessarily spot it, or you … Actually, I think this is a mistake a lot of women make.

We’re so task oriented to get things done. Making a list, get it all done, be super competent, kind of achieve, achieve, achieve, that when we look up from the proverbial desk, there’s no network there because we haven’t cultivated it.

J Kelly Hoey: Right, right.

Melinda Wittstock:         There are so many opportunities that way.

J Kelly Hoey: Or we don’t pay attention to … I think, like, another example that is in my book is Tina Roth Eisenberg. She founded CreativeMornings, and she founded Tattly, the temporary tattoos to do her to-do list. Within those businesses, part of why she started them was her community saw her ability to do it, and because of how she interacted with people, they were enthusiastic on jumping on board. So there’s an element of listening to your community and maybe they see a talent in you that you never imagined. If my network, my community hadn’t been so enthusiastic about the writing I was doing, I would’ve never contemplated writing a book.

So, like, listen and pay attention, and then, also listen and pay attention to your interactions, because they may see that you would be an extraordinary CEO, or they may see that you’d be an extraordinary author. But if you’ve been a jerk to them, they’re going to be, “Yeah, good luck. That’d be great. You’d be super at it.” Who’s going to stand there cheering for you? And the example on that I always think of is Kathryn Finney who is digitalundivided and the BIG Accelerator out of Atlanta, Georgia. Kathryn had a very successful crowdfunding campaign. But that was on the back of 15 years or more of being someone who gave to and built community.

When she reached out to her community to say, “Hey, here’s what I’m doing. I’m crowdfunding. This is the project I’m doing it for.” She said, “It was almost like a sigh of relief from all of them,” because they were like, “Oh thank you. We could finally do something for you.”

Melinda Wittstock:         Oh right. So this is to pay-it-forward thing, where this is so true of entrepreneurs. You really want to make money? Well go create value for somebody else, like solve somebody else’s problem.

J Kelly Hoey: Right, right. And if you’re thinking, “Is someone listening on this podcast?” When you’re thinking about, “Oh my God. Who’s my network? Who’s going to help me?” So many people are sort of there. They’re looking, like, the two steps ahead, and I’m like, “You know what? You got to look at the 30 feet behind you, and who are you bringing on this journey? And who are the people who care about you most?” If you’re really good as an entrepreneur and thinking, “All right. What are the other relationships I need?” You’re thinking about them long before you need them, otherwise you’re getting into this transactional treadmill that does not turn out well for anybody.

Melinda Wittstock:         Yeah, I think that’s so true. And so, when people think of networking, often they think of that horrible thing where you put on your little, sticky name tag, and you end up in some place, and it’s all small talk, and you got your glass of wine. It’s oh my God. It’s like, “Ugh.” It’s hard for a lot of people, especially anyone who’s introverted or just hate small talk, who wants to go a little bit deeper, whatever. So how do you deal with that kind of networking as opposed to more meaningful networking? What can networking actually be for people?

J Kelly Hoey: Yeah, so, I’m going to attack this in two ways. One, the networking you described, I’d rather poke my eyes out with a sharp stick. And hey, I wrote the book on the subject, and I hate that kind of networking. So when I think about networking, I take a big step back and say, “Let’s redefine this. If networking is building relationships, if networking is human interaction, then it’s everything we do 24/7,” and that’s where sort of the plus side and the downside of the digital world. Right now, you and I are networking because we’re having this conversation.

But we’re also networking because somebody is looking us up online, and we have a digital footprint, and you have a complete history of these podcasts that someone can start to get to know you and make an impression and think about who you are and what the value is. So, there is that, “Oh you’re networking all the time,” and how are you paying attention to the little actions every day? which I think are far more impactful than working in the room and having your name tag in the right place, and by chance, running into the dream investor who writes the check, between cocktails at a party. That never happen, but let’s … We’ll throw that out there just for fun.

I always think, you know, when you understand also too, where are the relationships you need to make? You may have to find yourself in those social or sort of horror story of networking. My attitude is, like, you navigate those awkward, small talk conversations by understanding why you made the decision to invest your time that way. If you know why you need to be in a room, you can figure out what to do and how to navigate it. I’m not saying it’s going to be fun. I’m not going to say you’re going to enjoy it. But if you’re like, “I need to go to that meetup, because everybody who does my area of expertise goes to that meetup,” and that’s where you get your name made, that’s what you have to go do.

There’s kind of no getting around it. I’m laughing because of your comment on introverts, because that was the second thing. I’m writing little notes here as you’re asking questions. So, my book is case-study driven, as you know, and I had ideas on the case studies, and wrote to people who had had outcomes. I mentioned Kathryn Finney. So, crowdfunding, getting on a corporate board, getting funded, working at the corporate ladder, building a business, like, I saw people with outcomes and I asked them to unpack it, because I had seen what they had done and known them and thought, “Okay. These are really good case studies, because it shows how this is replicable.”

This isn’t like winning a lottery and having a dream life. This is more like … I don’t know … doing sit-ups and having a washboard stomach. It might suck. There’s work involved. But if you do this, you, too, can have much more likelihood of an outcome like this other person. What I didn’t ask everyone I interviewed was their personality type. It wasn’t, Melinda, until I got their answers back that I had a startling discovery. The majority, as in the vast majority of people I interviewed for my book, are introverts.

Melinda Wittstock:         Ah yes. I am an introvert profoundly. Because I’m so outgoing, people assume that I must be an extrovert. But actually, no, I have to recover.

J Kelly Hoey: What I learned in writing the book is I’m an ambivert.

Melinda Wittstock:         Oh nice.

J Kelly Hoey: There’s a third category and I think more of us fall into that. Ambiverts get their energy from other people. But the reason why I think introverts in this day and age make the best networkers is that we are so bombarded with information and opportunity, and you think FOMO and you think everybody telling us what we should do. And that along with 24/7 and mobile and technology and all the rest of it, I think people who are more deliberate, intentional and purposeful, in terms of how they’re choosing to spend their time, how they’re choosing to share information, how they’re choosing to ask other people to do the same things make better networkers, and that I think are introverts.

Melinda Wittstock:         That is so interesting. I love that idea of, like deliberate, because you get to the point where if it’s not a hell yeah, it’s a no, right?

J Kelly Hoey: Right, right, or you know you want to say no, but you’ve analyzed it. You go, “I know I need to go and do this.”

Melinda Wittstock:         Well sometimes, actually, that’s been interesting, because sometimes I have thought, “Oh gosh. I really don’t want to go,” but something’s pushed me to go, and I’ve learned over time to really trust my gut feeling about these things. And then something magical has happened, like I’ve met the right person who, you know, as I’m-

J Kelly Hoey: Right.

Melinda Wittstock:         … to that beating, it was a whole new strategic partnership or some whole new revenue line or a different way that I could go in building an IP for the company or whatever I was working on at the time. So, some of those things are really magical. Honestly, when this podcast airs, I will be on my way to something called Camp Maverick, which totally reinvents how networking is done. So think about this. It’s like summer camp for entrepreneurs, like really, pretty high level entrepreneurs and all doing crazy stuff, like dressing up in wacky costumes and just doing events like playing bubble soccer or whatever it is, like Color Wars or whatever we do, right?

J Kelly Hoey: Yeah.

Melinda Wittstock:         But with seminars, with learning, with all these kinds of things, but it’s amazing because you make such deep connections with people when you’re doing something that gets you outside of yourself. This is a group of people … I mean, it’s probably almost everyone there is pretty highly introverted, is friendly enough. It transforms networking and the relationships from these sorts of masterminds and these sorts of things that are very purpose-built, have been revolutionary for me, but it’s just a matter of finding your tribe, who are the right people for you.

J Kelly Hoey: Right, and understanding why that group of people is the right … You need to connect with them because of what it is that, you know, your goal, your pursuit, your ambition. That’s what I always sort of say to people with networking. Start with the direction you’re headed. Now, who are the people that you need to connect with to make that happen? Now, tell me where they’re hanging out. I find with most networking, people go to the third pieces, the activity. This camp sounds amazing, but if you gave me the list and I’m like, “Well none of that applies to what I’m doing at this time.”

But maybe five years from now or maybe at some other point in time or maybe not at all, rather than people would say, “Oh my God. This camp Melinda’s going to, that sounds amazing. I want to go,” without assessing, is it the group of people that you need to be with? because you’re also having to give up time and give up something else. I think we bring our whole selves. We are authentic when we can be focused and present, and we’re only there if we know we’re making the right choices.

Melinda Wittstock:         It’s true. So I’m a total mastermind junkie in that sense that I have these kind of overlapping groups, because one of the things that I find in terms of innovation is really interesting things happen at the joins, at the little overlaps, where you combine like different expertise and whatnot. And so … Or just getting out of your comfort zone, or just doing something you wouldn’t otherwise do. That’s been really transformational for me. But I want to turn the corner a little bit in terms of your investing career, because I love what you’re doing. One of my big missions is to invest in other women.

The whole reason I do this podcast, by the way, is to affirm and acclaim the entrepreneurial journeys of women, but to create this ecosystem where women show up for each other, mentor each other, help each other, throw business to each other, and invest in each other. We started doing that early on, and we were seeing a lot of change, but we still are only getting 3% of the venture capital money. And so, what’s got to happen to change that? And what are some of the things that you’re seeing now as an investor, in terms of an investor investing in early-stage companies and women-founded companies?

J Kelly Hoey: I’m going to borrow from a friend of mine. The best form of investment is a paying customer.

Melinda Wittstock:         Oh yes.

J Kelly Hoey: So the first element on this, because women listening, saying, “Oh at some point, I want to invest.” You have the chance to invest every day, like what products you decide to buy, which service providers you choose to use, what people you decide to refer other people to. I’ll give a example. Someone said to me they were looking for a leadership speaker, and I’m like, “Alison Levine. Here, you want a leadership speaker? There’s your leadership speaker.” Every woman should have the Rolodex. If you believe in and want to see women succeed, then I would say make sure you have at your fingertips the people that you will refer others to, and I really hope they’re women.

There’s a great champion of women, and I’m like, “But yeah, every time I see who she does business with and co-writes books with, it’s like a dude.” I’m like, “You know, I see what’s coming out of your mouth, but what I’m seeing on paper, they don’t align,” and that really pisses me off to be honest.

Melinda Wittstock:         Right, and more and more. True. People are really looking for authenticity.

J Kelly Hoey: Right. We can do this. So people are thinking, “Someday, I’ll invest.” You make an investment choice every day. Whose books do you buy? What clothes do you wear? What products are you buying? Who’s your lawyer? Who’s your accountant? Who’s your bookkeeper? If you can choose between two equally great providers and one’s a woman, give your work to the woman. I mean, there we go. That’s kind of the first piece on the investment that I think about. The piece on venture … I’m sort of like, “Take a deep breath.”

Melinda Wittstock:         Fair enough.

J Kelly Hoey: So few companies get venture capital. We obsess over it rather than saying, “What are the other ways that we can get people’s businesses to be successful?” I do believe in the mix of what goes to venture. The fact that 3% go to women and even less to minorities, it’s pattern matching and it’s all wrong, and that needs to change, and I think that will change. There’s a couple of things that give me hope. One is, I think the pipeline for women in VC is changing. There are more women who are thinking about entering it and more women who are stepping up to pursue that particular profession, which is not an easy one.

I mean, you decide you’re going to become a partner in a venture firm. You’ve just signed on for the next 12 or 15 years of your life. This is not like, “Oh I’ll do it for a couple years and something else.” I mean, if you’re going to actually have the returns and be successful, you’ve now got to do something for the next 12 or 15 years. I probably just scared everybody with that kind of notion. But that’s the way funds work. But the piece on it … I think the other piece that needs to happen is, if you’re a woman who has got wealth, and most wealth in this country is now getting aging into the hands of women, then you need to say, “How am I investing in.”

If you don’t have the stomach to be a angel investor and directly investing yourself, then step up and be a limited partner and invest money that way, and find funds which are investing in diversity, and exercise your financial clout that way and make the VC firms change their perspective.

Melinda Wittstock:         I love that. That’s wonderful because it’s the limited partners that control the VCs. They’re getting their money from pension funds and from insurance companies.

J Kelly Hoey: Bingo.

Melinda Wittstock:         Right.

J Kelly Hoey: Bingo.

Melinda Wittstock:         So change those folks and what they do or … I love this … become a limited partner.

J Kelly Hoey: Right.

Melinda Wittstock:         [crosstalk 00:44:13] whatever, right?

J Kelly Hoey: Wait, because you think about VC firms. So even if it was a bunch of old white dudes who have the crazy attitude and stamina to be in venture, there’s more of an alignment between a VC firm and an entrepreneur than we think, because at some point, VCs need to go out and raise money. They’re not recycling their own profits. They’re paying those back out. They’re putting some in their pocket, because they haven’t been making any money until they have an exit. So they need to go knocking at doors for other people to give them money. The people whose doors they’re knocking on, a lot of them look like you and me.

We, as limited partners, so whether we are the pension fund, whether we’re the institutional investor, whether we are the individual who’s an LP, we need to be able to look and say, “That’s nice. I’m glad you have those returns. What returns could you have if you had an investment just in 22-year-old dudes who went through Stanford or Harvard, or 22-year old dudes who dropped out from Stanford or Harvard?

Melinda Wittstock:         Right. Exactly. No, this is so true. What I found quite astonishing though. Say, if you think of in New York, there are women of tremendous wealth there that have no issue writing a check. A big nice seven or even eight figure check in some cases, write to a charity. But try to get them to write like a $25,000 check to a female founder. I mean, even if that business is an evolved enterprise or a conscious capital or some social mission business that is solving the same issue, say, that the charity might be, and it’s really difficult.

I’d like to think that that’s changing. But is that really just an education issue that women get a little bit nervous about investing in something that that they don’t really know that world, and they think, “Oh well, but I do feel comfortable writing a check to charity”?

J Kelly Hoey: Yeah, well, you almost want to laugh when women say they’re not good with money, and I’m like, “Yo, a sale in Bergdorf’s and a discount, we can calculate that on a pair of shoes like no one’s business. We’re fine with money.”

Melinda Wittstock:         Right.

J Kelly Hoey: I just think it’s … What I found when people have been able to bring skeptical communities into the check-writing position is it is showing them that it is partly education. Partly it is building that network, and over time, showing them what can be done, but also saying, “It is about a return, but it’s also the bigger picture of what it means in terms of the products, the services. We can be in the driver’s seat of what it is that we see.” And funny that I say driver’s seat, because I always joke and laugh and say, “If women designed cars, there would be a place to put a goddamn purse,” right? There’d be a special place to put a goddamn purse, as opposed to under the seat or over here or wherever, if you think about it, right?

Melinda Wittstock:         Oh my God. Yeah, right.

J Kelly Hoey: So, you say, “We don’t have to play victims. We’re the ones with the money. What are we doing with it? And are we spending our power and the opportunity in the wrong way?” I was sort of thinking out some of the things going on right now. I say to people, “Why are you fueling the bottom line of companies that don’t represent your values? If your value is you want to see women founders succeed, then do something about it. Go and invest in their company, or go and buy their products, or … I don’t care what it is. Do something. The hand-wringing, I’m over it. We have a solution. Here’s what we need to do” I am so over … I want to say, like, the pom-poms. The women who are like, “Go girl. That’s great.” I don’t need someone cheering on the side.

Melinda Wittstock:         Yeah, you don’t need that. You need cash, right? I mean, really. It’s true.

J Kelly Hoey: I need them to be a customer. I need them to invest. I need them to roll up their sleeves and dial for dollars. I need them to do something. But the, “Oh yeah, go, go, but I can’t help.” No. We can all do something. If you’re choosing not to do that, then you know what? Just zip it and sit on the sidelines. I don’t need that anymore.

Melinda Wittstock:         I love this. This is wonderful, Kelly. No, but it’s true. There’s talk and there’s action, and actually buying from other women is going to be the most meaningful change, especially with this massive generational flow of money to women, like 35-plus. It’s a huge amount of money and it’s meaningful and it’s powerful.

J Kelly Hoey: It’s the largest transfer … The largest transfer wealth in human history is happening right now, and that is happening within the United States, and it is happening with women 50 and over. 70% of the private wealth in this country is going to be in the hands of women. We’re earning it. We’re inheriting it. We live longer. There’s the benefit of being the batty, old lady. You live longer, right?

Melinda Wittstock:         Right, and we’re in our 50s and 60s. That is true.

J Kelly Hoey: Right, right. So we’re earning it, we’re inheriting, and there’s the involuntary wealth transfers. Let’s just all admit it. Those things happen as well, right? Whatever the case is. Someone challenged me on this once. I said, “I don’t care if we’re drug dealers. Let’s just focus on the fact that we have the cash,” but my question is, what are we doing with it? Let’s not focus on whether or not the 70% is right, whether or not women are earning the money. Guess what? We have the money. Now, what are we doing with it? I’m like, anyone listening to this, I don’t care if you’re making minimum wage. If you’re still in college, you’re making financial decisions day in, day out.

And so, I say to you, are you making financial decisions that are in your long-term best interest in terms of, are you frequenting the companies that see you as a leader and want to promote you? If not, why are you buying their stuff? Are they the ones who represent your values? Are they the ones that are keeping the environment clean or whatever else you care about? I mean, I’m trying not let too much of my politics hang out, but whatever your value system is. If … I want to say … there’s a lot of people upset online with Waffle House. Well, why the hell are you still going there?

Melinda Wittstock:         Right. You see, but this is going to be true not just in terms of money, but as you suggested too in terms of politics and in terms of a lot of things, there’s a lot of problems that we can go solve that we’re uniquely capable of doing. And really, it’s just mustering that confidence and connections and capital. I mean, those three things are truly coming together, and it’s so exciting. Oh my goodness.

J Kelly Hoey: It’s awesome. If we start thinking that way, you realize that you really are powerful. But I would say to women listening to this, like take a look at who your financial advisor is. You may say you believe in stuff and went with investing in women, who’s your financial adviser?

Melinda Wittstock:         Mine’s a woman.

J Kelly Hoey: Mine’s a woman too. But also, too, all of a sudden, you might be getting advice that is reinforcing a stereotype that you can’t control your own money. “No, my financial advisor … ” Hold on a minute here. Is that person looking at the world from your perspective? And you’ve hit the nail on the head too, and the part of what got me to the table as an angel investor was the notion of, “Oh well instead of doing this to buy a table and have a rubber-chicken lunch at a gala, I will take that amount of money, and I will take this angel investor bootcamp and invest the equivalent amount as part of a group, and this is through the pipeline angels, their program.”

So they hit it exactly that way. It’s like, okay, I would write this check anyway. So instead, let me try doing it as part of a cohort and investing in a female-founded, for-profit social venture. And so, once you realize that you could do this and you were educated, and they weren’t asking you to do something that in terms of spending money you wouldn’t otherwise spend. It was like, “Oh well I can do this.” I remember a turning point for me was early on, and we were listening to a panel of experienced angel investors, and this one guy who’s been quite successful said … after explaining how hard it was and all the analysis and all that stuff.

And then he said, “But at the end of the day, I just trust my gut.” I remember sitting there thinking, “I’ve got a gut? I can trust it? Okay.”

Melinda Wittstock:         Right, exactly. This is so, so true. Well, Kelly, this has been the most amazing interview. I’ve really, really enjoyed this. I’m just going to share. We did have some technical issues, trying to get it together.

J Kelly Hoey: We’re women. We’re determined to make this happen.

Melinda Wittstock:         We persevered and here we are. What a beautiful interview. Thank you so much for putting on your wings and flying.

J Kelly Hoey: Oh my God. Thank you for providing the opportunity. I can’t tell you how much fun I’ve had. This has been truly a highlight, this podcast.


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Listen to learn the secrets, strategies, practical tips and epiphanies of women entrepreneurs who’ve “been there, built that” so you too can manifest the confidence, capital and connections to soar to success!
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Review on iTunes and win the chance for a VIP Day with Melinda