77 This Valentine’s Day, Learn How to Apply Business Skills to Your Love Life

Online dating is a confusing business, so this Valentine’s Day entrepreneur Jen Hecht shares how to apply business, marketing and branding skills to your “dating strategy”. Host of the Dating Advisory Board Show, Jen shares practical tips on personal branding and now to navigate the business of romance.

Melinda Wittstock:      Welcome to Wings, Jen.

Jen Hecht:                    Oh thank you so much, thank you for having me.

Melinda Wittstock:      It’s great to have you on, and I am fascinated by this connection between personal branding in romance and in business. Tell me a little bit more about the connection.

Jen Hecht:                    Right, well I kind of came from a personal thing when I ended up finding myself back in the dating world after many years, and I had this background in business, and I thought, it can’t be that difficult, the difference between dating and business. I mean, you’re having to find out your core value as a client, as a company, and now you are your brand as an individual in the dating world. So I came up with this idea, thinking, okay, I have to be able to know my target market. What are my core values? Just like a business boardroom runs efficiently, you need a personal advisory board.

Melinda Wittstock:      That is so interesting. So what are the challenges that most women are having in dating? And I want to separate out into two different groups, ’cause it must be very different for women in their twenties, than women, say, who’re coming out of divorces, and kind of reinventing themselves and all of that. So what are some of the things that you find where women need to get a little bit better on the personal branding side?

Jen Hecht:                    Well, I think we could tackle the younger generation right now. I think mostly in the young Millenials, but I have heard it from people in their forties that are now back after a divorce, is that there are so many dating apps that it is so accessible. Whereas in the past you had to go and meet someone in a bar, or a restaurant, or through work, and that’s how you met people. But now you have access to so many, so it’s hard for people to make a choice, right? Just like in business, if you have twenty different products, it’s harder to determine just which one you want to stick with. And I hate to phrase it like that, but it seems to be there’s … I don’t know if the traditional marriage is doomed for the younger generation, ’cause there seems to be … The data that I’m seeing is that they’re less to commit right away, if at all, or they just want a partnership. It’s very interesting to see how the marriage is going to change moving forward as technology keeps us driven in this world.

Melinda Wittstock:      I mean, I think of apps like Tinder and Hello Cupid and all of these, right? And yeah, you’re right, there’s so much choice. So it’s almost like you’re qualifying your potential partner-

Jen Hecht:                    Your prospect, right.

Melinda Wittstock:      … Yeah, like you’re qualifying your customers in a sales funnel.

Jen Hecht:                    Exactly. But think about it, those are hyper-specific in their target market, right? So Tinder is not like an OkCupid or a Farmers Only, right, they’re very specific and niche, what their product is selling. So Tinder is not normally for very serious relationships. Now do serious relationships happen from that? Yes, I have heard of them, I still like the case studies though. But I have heard of it happening.

But OkCupid is known as more of a relationship site etc., but Farmers Only … I love this scenario, these people are brilliant, we’re talking about branding perspective. Because Farmers Only, you already know exactly what they’re doing. They’re a farmers-only site, so people that live a farming lifestyle or want to be a farmer, they already know, when I sign up for this site, chances are, they’re going to be a farmer or a farming lifestyle. So you already know what you want, you know what your core values are.

And a lot of the times when you go back and say, “Well, what are you looking for?” It’s going to be very different in your twenties versus in your forties or fifties or so on, because you’re in a different style of your life, right? You may have kids; you may not want kids. So being hyper-specific and knowing what you really want will … Just like in business, mapping it out like you would map it out in the business boardroom, map it out in your personal advisory boards as well.

Melinda Wittstock:      So this can seem a little bit intimidating I think, if you’ve been out of the dating world for a long time, and say you are a woman in business. It’s not like you don’t have a lot of demands on your time, you know, if you’re running a business, or you’re a solopreneur, or you’re an executive, or you have side-hustles and gigs and all of that, right? We’re all so busy as it is. So just the dating game to me sounds like a full-time job in and of itself.

Jen Hecht:                    Right, I mean it does … It can get aggressive, because-

Melinda Wittstock:      Yeah, so how do you juggle all of that?

Jen Hecht:                    Yeah, I think you just … A thing that I’ve heard, you know, I believe … Just like you shouldn’t sell twenty different products, right, to be really hyper-focused and really good at one product? I think you should focus on one or two apps, and really go in when you have time. And I also say, being ready for it. Don’t say, “Oh I want to be dating, and I’m just going to go on a dating site.” And then you start swiping, but then you never follow through. You never actually meet up on those dates. Whether you’re convincing yourself, “Oh, I’m not ready,” or “I’m just so busy.” It’s some sort of an excuse, right? And I would start off by just starting with one site, or two sites, or even … Especially for the executives who are busy, they have a lot going on, and they’re creating their hustles and their empires, is hire a matchmaker to do it for you.

Melinda Wittstock:      Right. That’s interesting, because so often on this podcast, on Wings, we talk about doubling-down on your strengths and hiring your weaknesses. So if you’re a busy executive woman, why not delegate this out, right?

Jen Hecht:                    Absolutely, and here’s another thing that I say, especially to our friends, because we do have such big networks, but it’s also a very small circle. Especially in the district, the DMV, I mean, everybody knows everybody.

But the thing is in business; we tend to ask for referrals more than we would do in our personal life. I know I don’t ask my friends, “Hey Rita, do you know anyone?” Or, “Melinda, do you know anyone that’s single that may be a good fit for me?” But they may not know at that particular time, but if they’re at a networking event, or they’re at a business meeting, or they know some distant cousin, who knows, I’m just saying … But now it’s in your head, “Oh yeah, that would be a good fit for Jen.” But it may not be in that moment. But just putting that thought out there, just like you do in business, right?

Melinda Wittstock:      So on your show, I know you interview a lot of female business executives and entrepreneurs, and they have backgrounds all across sales and marketing, and matchmaking marketing, public relations, branding, technology, networking, all of these different fields. Are there any patterns that emerge in terms of how women show up, in terms of their personal brand? Where are women doing well, and where can women do better?

Jen Hecht:                    I think being number one is, across the board, I think this is across … Who you surround yourself matters on where you’re going to be in this life, or want to be in this life. And I think, when I look back at a lot of my women entrepreneur guests, they all come from a very authentic self, right? They’re walking in the boardroom one way and they’re walking out the exact same way when they walked in, right? So being true to who you are, just like in dating, don’t be a representative when you’re going in to … Don’t say, “I want to have kids,” and then you really don’t. ‘Cause it’s going to come out!

I did hear that story the other day, this one girl said one of her friends, or sister, I don’t remember who it was, but the premise is that they said, “Well maybe he’ll change his mind about not wanting kids.”

Melinda Wittstock:      No.

Jen Hecht:                    No, he’s not going to change that, that’s a pretty big deal. So don’t think you’re going to change a person’s thoughts, and even, why would you want that? So I would say know your strength, I always say stay in your lane. So I know what my core non-negotiables are when I’m looking for someone. They were not the same when I was twenty, but they are now I’m forty.

Melinda Wittstock:      That reminds me of something. I mean, one of the chapters in the book that I’m writing is called The Fixer-Upper, and most relationships that fall apart, fall apart because one or both thinks they can change the other. And at the root of settling for someone who’s not really the person for you, I think, is a belief deep down that you can’t actually get, or you don’t deserve, what you actually want. And so sometimes people go and they settle for the fixer-upper, and what I’ve connected is, that sometimes happens in business too. We go for fixer-upper clients or fixer-upper investors, and at the root of it is that we’re not valuing ourselves, and so therefore we’re not really showing up as our authentic selves. So what do you tell women about how to actually even be in touch with their authentic selves? ‘Cause I think sometimes we’re living other peoples’ lives, not even our own.

Jen Hecht:                    No, I think you’re 100% true, and I think we do, at least for women … I know I struggle with self worth. If you have in the past, if someone who said negative things, or you can’t do this, you can’t do that, and then trying to get out of that mind-set. So advice I would give to them would be, just make sure that you go back in kind of in an athletic state of mind, and visualize, okay this is where I             want to go, and this is where I want to be, and do that. That’s what I do, I may have a little bit of background in that as well from tennis, I use an athlete’s perspective.

Melinda Wittstock:      I like that, develop that a little bit more, the athlete’s perspective, because again, there’s so much research that shows that women who are really successful entrepreneurs and executives have a competitive sports background, and of course, you are a tennis champion. So tell us a little bit about your background in tennis, and how that’s impacted your business life.

Jen Hecht:                    I would say from a very early age my dad [inaudible 00:10:04] I was going to be in some sort of sports, he’s like, “She’s just so competitive and she wants to win,” and I always said, “Well is that genetic? Or do you think that was taught?” And then he’s like, “I think it’s little bit of both.” And so my dad was a single father, raised me, and really put me into tennis, more as from being part of this divorce, a tough divorce, and really channeled that energy, like channeling the negative energy that was going into a positive. So like I said, it still comes back to self-worth. If you are hearing negative things, or hearing a bully, or somebody, just because they’re unhappy with themselves, try to channel that into the greater good, or use that as a stepping stone to really push yourself to the next level.

So with tennis, I had coaches. And you have to have a coach in every aspect of your life. Look at the most successful entrepreneurs and CEOs, they all have coaches in different facets of their life, and for someone to say, “Oh I’m fine, I don’t need any help,” I’m like, oh, you are the number one person who should make an appointment.

Melinda Wittstock:      We all need all the help we can get. You know, if you want to live big-

Jen Hecht:                    Yep.

Melinda Wittstock:      … Yeah, you know, why not have those networks and mentors and coaches, and all the support-

Jen Hecht:                    Absolutely. I talk about the last mile … So this chapter of the book Born To Be Me that’s out available on Amazon, you can go grab a copy, but we talk about these authentic stories of these women, and there’s eighteen other women. But my chapter is called The Last Mile. It’s the story about when I was 17 years old, 16-17, and I was training really hard for a tennis tournament where lot of college scholarships were going to be, and I needed to perform and get a scholarship in order to play, and play to go to college in general. I mean, that was it; It was like, make it or break it, kind of situation.

And I had an eight-hour tennis camp in the middle of August, summer in Michigan, so the humidity was brutal. We’re driving home, my dad picks me up, we’re about a mile out, and he says, “Get out.” And I said, “What?” He said, “Get out.” I said, “You’re nuts, I’m not going anywhere.” And he said, “No, you’re going to get out,” I said, “What do you want me to do?” And he said, “You’re going to run the last mile home.” I said, “You have officially lost your mind. I’m not doing that, I am not going out there.” There were pheasants, I gave every excuse, there were pheasants out there, there are wild animals; I can’t do it, I’m tired and exhausted. And he’s like, “Get out. Run.”

It was funny; he’s a comedian. He wasn’t a mean dad; he was really great. But it was a metaphor for my life. He made me run the last mile home. I had it in me, he knew I had it in me, but I didn’t believe in myself.

Melinda Wittstock:      Ah.

Jen Hecht:                    Right? And so he got home, and he said, “See, I told you, you could do it.” And I said, “Oh, you are right, Ricky.” But the whole thing is that it’s a metaphor for my life. So in every aspect of my life, I say to myself, did I run that last mile? When it comes to relationships, and I talk about in the book, love and loss and everything in between, it basically encompasses the whole chapter. But did I run the last mile? Did I speak my truth? Will I live in regret from that? And in business, is this what I’m really supposed to be doing? And I need to pivot when I know something in my core is not right, and visualize where I want to be. And that comes from tennis…that comes from being an athlete.

Why do you think a lot of … What is that, nation-wide, I believe it was? They are the ones who hire all the college athletes as sales-people. It’s brilliant. It’s like the number one … I don’t know why more companies don’t target athletes. Because they’re competitive, they want to win, and they have a good work ethic, and they’re coachable.

Melinda Wittstock:      Right, coachable and also there are such interesting techniques used in sports. For instance, visualization…

Jen Hecht:                    Yeah.

Melinda Wittstock:      I was a competitive figure skater-

Jen Hecht:                    Oh wow.

Melinda Wittstock:      … When I was a kid. And I remember learning this at about age ten, because I went to sleep one night … I was struggling with a jump called the Double Axel, and I really wanted to be able to learn this jump and do this, and I was falling, over and over and over again, I was getting a little demoralized. But that night, I visualized it, I dreamt it, and I felt myself do it. And I swear, I went on the ice the next day, and it was the first thing I did the easiest thing, and landed it, and mastered it, and it was because I could see myself doing it. So it’s kind of like self-belief.

So I’ve taken that lesson all the way through my life, that if I could see it, and really feel it, then it became real and I could do it. So-

Jen Hecht:                    I’ve got great advice on that too, just because for tennis, and we bring it back to athleticism too, is the way that we had different mental coaches, forehand, backhand, wherever you were needing help, right? So they would say, “Visualize the shot before it happens. Visualize, you’re getting up to serve, alright what’re you going to do? Down the line middle,” … So you’re literally mapping it out, ’cause you’re seeing it play out, so then you’re automatically doing it. And the same, in your business … I literally went to Home Depot, got the whiteboard/chalkboard paint, and painted one wall so it could be my whiteboard, right?

So if you write down what you want to do, where you want to be, you don’t even … You can put it on mirror and write on your mirror what your intention is for the day, or where you see yourself. But putting it out there, and then, like you said, visualizing, but then reading it makes it into a reality. I do believe in… you put it out into the universe, it does come.

Melinda Wittstock:      Interesting, I believe that’s true. It’s a struggle though often for us to know ourselves, whether in dating or in business, and say for instance you’re building a business, and you’re building a team. And you have to interact with so many people. Perhaps you have a board of directors and investors, you have vendors, you have team members, and in the dating world you have all these different potential partners you’re evaluating.

Jen Hecht:                    Right? Yeah.

Melinda Wittstock:      And in that context, it’s sometimes hard to know ourselves, and as women, we tend to want to people-please, and so-

Jen Hecht:                    Absolutely.

Melinda Wittstock:      … We can sometimes lose ourselves. So where is that boundary, or how can women practically figure that out? Is it something as simple as … I mean, my tactic is, every time I hear myself saying I should do something, I know that that’s not really me.

Jen Hecht:                    Yeah, should be doing-

Melinda Wittstock:      That’s an old learning belief, that’s somebody else’s life, right?

Jen Hecht:                    Right.

Melinda Wittstock:      So that’s my little tactic. But are there any others that can help people really step into their authentic power, if you will?

Jen Hecht:                    Right. I mean, I think in your true … You know when you’re in the right place. If you’re working for a job, and you’re like, I cannot imagine literally opening that door and going into that client’s site, or into that office, that’s clearly not where you’re supposed to be. So you need to kinda go back and figure out, okay, where are my core strengths, what makes me happy, what makes me passionate about it? Right? And then you just move from there. Okay, this is what I want to do. Now how to get there, then that’s a whole different story, but I’m just saying if you know your purpose and drive in your life, you may or may not find someone who can help you map it out, you should vision map it.

Melinda Wittstock:      So Jen, what made you create this business around dating and the show? What was the motivation?

[tweet_box design=”default” float=”none”]You have to know what you want to do, and just like a horse puts blinders on. Don’t look at your friends, don’t look at the Jones’s, don’t look at what they should’ve done or whatever. You just have to put on your blinders and say, “Okay, this is what I’m doing. #WingsPodcast #WomeninBusiness @JenHecht1[/tweet_box]

Jen Hecht:                    The main motivation for me creating the Dating Advisory Board was because I was looking for an environment, a group, to help empower each other, and I couldn’t really find it. Right? Like, what do you do after a divorce? Like you said, we’re taking business strategies from different industries, and we talk about it on the show, and how that can be in business as well as in dating. And we just want to be a community to empower women to approach their lives with passion and clarity. So that’s my main focus with it. Because I couldn’t find anything, there wasn’t anything out there saying, okay, here is some advice from a dating … In one site, one cohesive place to find it. Here’s business and dating advice all rolled up into one.

So you don’t have to be single to gain knowledge from the sites, from the shows as well, and from the dating you can also learn business. It’s a win-win.

Melinda Wittstock:      Even people in relationships, I think it’s a constant struggle to keep up the level of intimacy over time, especially when we’re pulled in so many different directions, you know?

Jen Hecht:                    Absolutely.

Melinda Wittstock:      I think of entre-pioneering women with businesses, with kids, with partners, trying to keep up with their friends, I mean there’s so many demands on our time. So how to keep that intimacy in our relationships? Because to have a good relationship is also really helpful in business as well. Women who are really successful tend to have really good relationships, marriages, or just relationships with their partners.

Jen Hecht:                    I may kinda go back to answer the one question about how you do it. I think there are so many distractions, and I think that places this question too … You just have to know what you want to do, and just like a horse puts blinders on, they don’t look at their friends, they don’t look at the Jones’s, they don’t look at what they should’ve done or whatever. You just have to put on your blinders and say, “Okay, this is what I’m doing, I’m going full force, if I stumble, I fall, I’m still going to get back up, and I’m still going to finish the race.”

Melinda Wittstock:      That’s really important advice. So going back in time, I like to ask women who come on the show, who their ‘Super-Sheroes’ were when they were growing up. You’ve spoken about your dad, who is obviously very, very big influence in your life. Did you have female role models as well?

Jen Hecht:                    Yeah, Wonder Woman.

Melinda Wittstock:      Wonder Woman, I know, Wonder Woman. Did you see the movie?

Jen Hecht:                    You know, I have not yet. Linda Carter actually, she lives close to me apparently, I guess she lives in Maryland as well. I’ve never met her, but that’s a goal, right? But you know, I used to walk around all the time with tin foil on, for my bracelets, right? And imagine being Wonder Woman, and saving the world, and I always kind of kept that as well. So today, I have a Wonder Woman bracelet that I wear, actually one that is a Wonder Woman bracelet, and then the other one looks like it, but it’s gold, and people say, “There’s your reflector,” and I say, “Yeah, I wear it all the time.”

Melinda Wittstock:      Seeing that movie, I went to see it with my daughter, and she’s fourteen, and what was wonderful about it is that the authentic feminine power was a graceful, empathetic power. It was a power of attraction, and intuition, as well as a physical power. Interesting, you know, when we think about being authentic, or being great leaders, or inspiring people as we have to do as entrepreneurs in our businesses, attracting the right man or woman, the right partner. Having that balance between the archetypal masculine energy and the archetypal feminine energy is a really interesting kind of place to be. How do you view that? I mean, when women are really being strong, we can sometimes being strong with being like a dude.

Jen Hecht:                    Right, well, and that’s the thing you battle with, and I bring it up a lot on my show, is that … And you hear from different guys’ perspectives, if you have two alphas, I mean, it’s hard. There’s always compromise in a relationship, so when you’re … I had one guest say on my show, “Leave your cape at the door when you come home, and just be human.” It’s not about winning; it’s about compromising and showing up where they’re at! And then I always kind of go back, well, can two alphas work? Can two type A’s work? And they said yes, it can work, but you have to have an agreement. You have to know when … It’s not, who won this argument? Nobody wins. You’re still having to work together. So being able to communicate is really key. And you talk about intimacy, and how to bring about that closeness, and it is communication. How are you communicating with each other?

Melinda Wittstock:      Yes, you could have, I suppose, two type A personalities, as long as there’s a real respect. I think it’s difficult for women to out-man a man. And I’m not saying that, not to be strong, ’cause I think women are incredibly strong, and in fact sometimes I think we’re stronger and more resilient than a lot of men. It just exhibits differently.

Jen Hecht:                    Right, and how the brain works, and they call us crazy ’cause our brain can work simultaneously, whereas the men brain can only work one hemisphere at a time. So I always thought that was interesting, from the science perspective.

Melinda Wittstock:      Yeah, there’s a great comedian, and I can’t remember his name now, but it was so funny. You know, he talks about how men have these different boxes, and they can only really be thinking about one thing at a time. They’ll be in their work ‘box’, or their relationship ‘box’, or their kind of run-the-errands ‘box’, but none of them link together. Or-

Jen Hecht:                    Right? And women, we have to make sure we have all of them all at the same time-

Melinda Wittstock:      They’re all at the same time.

Jen Hecht:                    … All at the same time, and that’s why they … Someone else was telling me this, that most businesses are strategically putting women as project managers, which I thought was interesting, because they can multi-task so well, and they’re used to be doing 50,000,000 things. And I don’t know who, maybe it was Reese Witherspoon, I saw something that came on that she was giving a speech a couple years ago, and she’s an example … In a crisis situation, does a child go up to the girl or the guy? And they’re like, it goes up to the girl, because she knows how to handle crisis situation, right?

Melinda Wittstock:      Well, we connect-

Jen Hecht:                    So that was interesting.

Melinda Wittstock:      Yeah, we connect the dots, I think, in an interesting way.

Jen Hecht:                    Exactly.

Melinda Wittstock:      Some people call it web thinking, or systems thinking. That ability to see how all these different parts meet, and what’s interesting to me in my entrepreneurial career and all the different Accelerator programs as a tech entrepreneur that I’ve gone through. I’m thinking specifically of Springboard Enterprises, which is actually one of the show’s sponsors. And it was fascinating to look at all these different female business models, because they tended to connect the dots in a very non-linear way. And when these women went to go get funding, a lot of the male VC’s didn’t really necessarily understand their model, because it was a matter of understanding the female brain, which works differently.

Jen Hecht:                    Right.

Melinda Wittstock:      And it was fascinating. It wasn’t just like, oh wow, you’re a woman, and I don’t want to fund a woman, it was just that they couldn’t necessarily understand the model. And it became increasingly obvious that women had to translate that, or have empathy for how the guy was thinking of it. So you can change the game, but on some level, you have to play by the rules as well. Where is the balance there?

Jen Hecht:                    Right.

Melinda Wittstock:      You know? And it was interesting to see the difference. So, we like to make sure that we ask all the guests for their top three kind of wings of advice. So, with your kinda Super-shero wings on, what would be the top three pieces of advice you would give women, in business, and in their romantic lives?

Jen Hecht:                    I think I always go back to the last mile, right, ’cause that’s a metaphor for my life. Just when you think you’re done, you’re not, and you just never give up. And I always say, your future self is counting on you, so don’t let them down. Just got to keep pushing until you get what you’re looking for. At least close to it, then you can make a decision, but I’m just saying, don’t give up, just say, “I’m tired, I can’t do it.”

And that goes for dating as well, ’cause you hear it a lot, “I’m done, I had a bad day, I’m giving up on dating.” No, that’s a deeper-seated issue that we need to discuss, why you’re just giving up on dating completely. But just don’t give up, you never know what’s around the bend, right? You keep running, but you don’t really can never normally see it, but just know that it’s there.

And I always say stay in your lane, right? Make sure you don’t get diverted off a path, like you said, where you’re getting pulled in twenty different directions, people are saying, you got to do this, you got to do that, or you got to do that. No, know what you’re good at, stay in your lane, and just keep your blinders on and keep it moving.

And then I would say the third thing is, being coachable in your personal and professional lives. I think that is so key, you have got to be coachable. Just because, you’re going to get better, just like all athletes, all entrepreneurs, they are successful because they have coaches.

Melinda Wittstock:      Yes, I could not agree with you more about that. The coach-ability is absolutely critical. So do you have any special offer for our listeners today, and how can they find you?

Jen Hecht:                    Great, yes. Special offers would be Born To Be Me is out on amazon.com. I love this book, because there’s so many inspiring women who wrote their truth stories, so please, I would love … There’s a special discount, if you write a review they’ll give you a gift card. It’s amazing, so that’s really great.

Melinda Wittstock:      How can people find you, where can they find your show, and all of that? ‘Cause it’d be awesome to listen to!

Jen Hecht:                    Yeah, sure. So you can go on thedatingadvisoryboard.com. Under my tab Brain Trust I have all of our shows that are listed and give you a description of each, and you can find us there.

Melinda Wittstock:      Okay, that’s wonderful Jen, thanks for putting your wings on today and flying with me.

Jen Hecht:                    Okay, thanks so much Melinda, I really appreciate it.


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