Dr. V Boykin on Breaking Barriers & Leading Without Apology | Women of HubSpot

Welcome to the Women of HubSpot podcast, the show that celebrates the voices shaping marketing technology and the ever evolving HubSpot ecosystem. Hosted by George B. Thomas from Sidekick Strategies, each episode brings you the stories, strategies, and superpowers of the women driving this industry forward. It's their time. It's their mic. This is Women of HubSpot.

All right, it's your boy, George B. Thomas. And we're back with another episode of Women of HubSpot. And hey, if this is the first one you're watching or listening to, I'll give you a quick rundown. It was the Super Bowl. The Philadelphia Eagles were in the Super Bowl. No, I'm not necessarily a Philly fan, but I have some friends who are Philly fans, so, hey, there you go. The moral of the story is the quarterback had an all women's team. My daughter started to conversate about that. I saw their face light up and I was like, man, why don't we do this in our space? When I say our space, I mean the HubSpot space that I've been part of since 2012. I went to LinkedIn 0 strategy just being a dad of women who were impressed by this thing. And I did this post, hey, let's shine a light on the women of HubSpot who either work at HubSpot or work with HubSpot or use HubSpot. And all sudden, the post went nuts. To which I said, there's conversations here. My daughter said, yes, there's conversations here. And we started this podcast. And believe it, I tell you that these conversations have been absolutely amazing. And it would continue to go today because I'm not here alone. I am here with Dr. V. Dr. V, how the heck are you doing today?

I'm doing fantastic. And I love the concept of this podcast. I love how you are listening to your family and watching their reactions and from that place created change. So good for you. Great to be here.

You know, it's good to have you here. I'm super excited. I know I've interviewed you before. I know I was impressed and loved your brain and your mind and the way that you communicate. And so here's the thing. We would have these interviews, we'd have these conversations, and I gotta be honest with you, your name kept popping up, the women of HubSpot kept talking about you. And I'm like, we gotta get Dr. V on the show. So before we get into the questions of Dr. V, maybe explain to folks who you are, what you do, and kind of where you do it of.

Course I love that my name came up because so many women of HubSpot's names come up when I am talking. So I appreciate that we're sharing that energy. What do I do? Who am I? I'm a former single mom, felon, stripper, now two time author, keynote speaker and doctor, and I tell the truth about what happens personally and professionally and how to best navigate the situations that come up. I am currently the Vice President of Disruptive Innovation at Lyft Enablement, which is a HubSpot Elite partner.

I love it so much. That intro. By the way, ladies and gentlemen, listeners, viewers, you should just know we're about to go on a ride. So Dr. V, if we could go back in time, what would she be most surprised about where you are right now?

Oh gosh. Well, that's a great question, so thank you for it. I think young Dr. V would have been a single mom desperately fighting to make sure her kids had what she, what they needed. And she was also very confused about what they needed. So you would see decisions that were incongruent with the desired outcome, but would make total sense and she would explain them to you like they were fact. And I think that she would be most surprised at how poorly her choices shaped her life and how incredibly brilliant she remained as she made those poor choices. Like, there is a brilliance to the human spirit and human condition when you make it out of the muck. Especially when you've like literally seen the muck, identified the muck and then jumped in for a swim knowing you were going to suffocate. There's a brilliance, a madness and a brilliance in that. So I think she would be really surprised at the choices that she made based on what truly did matter most to her, but how those choices ultimately got her in a space that allows her to do what matters most to her.

I love this idea of the choices we make and also the fact that you like see the muck dove into the muck, but you know, getting, getting out of the muck as well. It's so interesting. So this journey of like mother trying to do the best she can, going through the process, making choices, trying to live life, it, it kind of creates this journey. And I'm super curious, on your journey that you've been on, like what are some of your biggest inspirations or mentors that you've had along the way?

In a very self serving way, I've never been motivated by dreams. I've always been very motivated by nightmares. Like what I couldn't possibly allow to happen. So a lot of the choices that I make have been just to avoid the nightmare with this undercurrent of something my grandmother told me before she passed, which was like, hon, never do something that you wouldn't do on, on the, on the corner of Murray Avenue. And she did not mean like the stripping prostitution part.

Right.

You know, she really meant as you would stand in front of your community, make those choices. And I didn't always do that. And I remember after she said that, like, gosh, that really needs to be this guiding principle, like, what would I do if I was in Pittsburgh standing on Murray Avenue? A lot more of those things align now than they did back then. But my grandmother was a huge, huge influence on me, and she remains so today, even in her absence.

So a, we started by talking about choices. Now with your answer of like grandma being the inspiration or mentor. It's like this idea of visibility and decision making based on if you even put yourself in kind of that visibility matrix. Very interesting. Okay, so I go into these questions, Dr. V. That I call the kind of valley questions. We do rise to the mountaintop for some funner more maybe inspiring, but. But I think there's lessons to be learned in what you call the muck, the Meyer, if you will. And so let's go ahead and get into some of those questions. Have there ever been Dr. V. Hurdles, biases that you've had to overcome in your career? And if so, how did you actually navigate them?

Well, there's been a lot, and there remains to be a lot. It's been over 20 years since I was off paper as a felon, you know, totally had done my time, yet I still lose out jobs, I still can't rent apartments in certain areas. There's industries I'll never be able to work in again. There's people that don't want to know me, don't want to talk to me, don't want to be associated with me, or on the other hand, want to offer me some sort of forgiveness that I never requested and frankly don't need. So there's that bias. There's the other bias that I'm a black woman, and that's tinged with some complexities, right? Because I have an appearance that is very Caucasian forward, especially if I just got my hair done. And a lot of times that means I'm in rooms hearing things that they might not say if they recognized I was in the room. And that whole dichotomy of when do you speak up and when do you not you know, spoiler alert. If you're early in your career and you can't afford to speak up, don't you know us aunties and uncles will take care of it when you can. Please do. I think there's also a lot of stigma attached to the fact that I just say, yes, I was a stripper and did it sober and didn't have an issue with that. So what kind of person must I be? Well, the kind of person I am. So there's that. And a lot of the reason that I'm so forward facing and so vocal about what I've been through is I know I'm not the only one. I know that I'm not. But I might be the only one you come in contact with that feels comfortable saying it and owning it and really leaning into that. And the interesting thing is how that translates also into the workplace because when you are hiding and hoping, nobody hits Google on your name. There's, there's a hesitancy and a lack of boldness in your movements. And that's why one of the reasons, for me, it's so important to really synthesize who I am, both personal, personally and professionally.

So good. I love this idea of this confidence in who you are, this boldness in how you need to show up based on the ownership of kind of the choices and visibility of the historical you, but also this idea of being able to navigate it in a way of like it, the, the history doesn't affect the like infinity of what is to come in your life. This is so good. Okay, so we'll keep going. In these kind of valley questions, have, have you kind of faced moments where you felt underestimated, maybe even overlooked or just kind of out of place in the industry? And, and if so, if one of those moments comes to mind, like, how did you handle it?

I think I'm always underestimated. You know, I'm a woman. I'm 5 foot 4 and like 110 pounds. I don't think people know what's coming their way. When I come their way, I've definitely sat in positions and roles where I've been passed over for promotion. Year one, year two, year three. When you see other people that don't have the same qualifications or skills getting those promotions or haven't made the same quantifiable or qualitative impact. That is the experience of, for me, a black woman in the business space. There's a ton of obstacles to even acquiring a job as a felon. Even though I didn't Have a life sentence. I still, you know, again, have that experience of a life sentence. There's a ton of things you overcome as a single parent, including convincing your kids you're camping inside the house because the lights are turned off or counting your changes. You're going to the grocery store and they think it's a math exercise, and you're trying to figure out how much you can actually spend down to the penny. You know, being in line and realizing that your food stamp card didn't reload and you have to put everything back, and you're just like, oh, gosh, this couldn't be more embarrassing. Or that WIC voucher. And suddenly, like, all the people you've ever met in your life are right behind you in line as you're trying to use your WIC falter or your food stamps. Like, all of these things inform who you become and how do I handle it? There are times I remain silent and hid, and there are other times I stood up and fight, you know, and fought and. And won, and then still winning. The reconciliation of that is you do what you can afford to do in the moment you're in, and you do it the best way you can with the information you have in the moment you're in. And whatever you can't do is not designed for you. Somebody else will pick that up.

What you can't do isn't designed for you. First of all, that might be a rewind point in the episode. Just get that notepad out. Jot some of those things. I love your authentic transparency in this question. And it's interesting, too, because before we get started, kind of in the green room, you asked if I had had a chance to see your book yet. Why don't you put the book up on screen so people can see that? Because this, for me, is like a moment where you're like, I'm just gonna be me, and I'm gonna put out into the world what I can put out. And it totally aligns with the answer that you just kind of gave is like, it's time for me to say something. Here's the way that I'm gonna deliver this to the world. I'm going to go off of our normal questions. Can you just give me a synopsis? And the viewers and listeners kind of like a short synopsis of the book. The what, the why, kind of the how. Around that.

Yeah. Thank you. My second book is unapologetically disruptive. Hard Lessons, Simple Truths. And it's really centered around four basic lessons that apply personally and professionally. And this book. Oh, this was hard to write. The first one was kind of fun. It was like, ha ha, what'd you say about me? Um, this one is like, haha, what'd you say about me and how did it impact my life and how could it help other people avoid missteps? It is a wild ride. It is a hundred percent true. Which is not a brag and not an apology. It's just facts and it talks a lot. One of the quotes I really like from it. Are you allowed to like quotes you did yourself? But anyway, okay, so here it is. Never allow anyone to determine your significance, especially in environments where wounded people sometimes mistake control for leadership. So it's that kind of book. It talks about what happened in high school, it talks about what happened in college, it talks about what has happened in my, my corporate experiences. And it talks about some things that I've gotten wrong and other people have gotten wrong. So it's, It's a wild read. Buckle up. It's a very quick read as well.

Love it. So good. Okay, so let's go ahead, kind of dovetail that or book end it. No pun intended. Dr. V. Have you ever experienced significant. By the way, I know the answer to this, but I still have to ask the question. Have you ever experienced a significant failure or setback in life? And based on the one you pick, what in the world did you learn from it?

Before I went to prison, I had a really great boss and he was a VP of Procurement, I believe was his official title. And I was learning so much from him. And he went on vacation and the office environment really shifted. And when he came back, I said, I'm so glad you're back, because while you were gone, I applied for all of these different roles because I just didn't think I could take it here. I'm not exactly sure what his response, I thought his response would be, but it wasn't like, oh, I'm so glad I'm back. Also, it was like, oh, you're disloyal and let me go contact hr. And that is literally what happened. And it was bad. It was really bad. And I had also interviewed someone because I was going to be getting an assistant. And I said to this person out loud, I want you to be my assistant because there's times I need to run and drop off my dry cleaning and I need someone here to cover. Like, I couldn't have been more immature, more ill prepared, more unprofessional, more, more, more, more. And what I learned is Number one, sometimes you're wrong. Number two, your words have consequences, which is okay. You just have to be prepared to pay the piper. And number three, if you don't start at the beginning of a story, people won't be able to follow. Like, for example, I didn't say I've learned. Enjoyed learning so much from you. I realized what would happen if you weren't present. I know how much more additional learning I have to do. I started examining opportunities that would allow me to continue to grow while you were out of office. That is a totally different conversation than I'm about to skip out. You like that. But those lessons are still things I struggle with. I still start in the middle of stories. It's just how my brain kind of works. Doesn't make it right. Just makes it a skill area to work on.

Yeah, I love this idea, first of all, of knowing how your brain works, because then you can try to reverse engineer, like, hey, this is how my brain works. Let me go ahead and add this additional context into the story that I'm about to tell. And there's just so many good pieces. Okay, so let's kind of crest up the mountain here a little bit because I'm super curious for you, Dr. V. What does empowerment mean? And. And how do you kind of pass that on to others in your field?

Oh, in like 10 seconds or less? Yeah, no problem, George. That sounds great. Empowerment for me is choice, full stop. It's the choice to be as traditional in your relationships, personal and professional, as you want to be. It's the choice to be as non traditional. It's the choice to say the things that you want to say and be able to withstand what comes back at you when you push that out. So empowerment is not about who's opening the door. It's about the fact that you are very solidly and firmly planted in the fact that you can open that door to the fact that. To. To the full fact and feeling that if somebody else wants to, you're still planted just as firmly when you see the door opened for you. That'd be a good way to sum it up for me.

I love that. So now that we have this kind of shared understanding of what you consider empowerment, Dr. V, I'm super curious if you could share a moment in your career where you felt especially empowered or proud of something that you achieved.

You know, I've had the privilege of doing a lot of really cool things that come with numbers attached to them and dollar signs attached to them. What I'm most proud of is every person that came to me for advice that allowed me to learn from them. As we were talking through challenges, those very small moments, names that'll never be said, activities that'll never be on a performance review, the fact that those people trusted me, respected me enough to ask my opinion, and felt safe enough to show up as their authentic selves to work through things, there is, there is no honestly, greater ego boost. And there's also no deeper connection to being human than being able to show up in those moments and have the privilege of supporting someone when they need it most. That, that's why I write the books. That's why I answer every LinkedIn message. That's why that's not my dharma.

That's, that's my fuel, your purpose, if you will. I love this. Ladies and gentlemen, I would, I would beg you to write down the idea of trust, respect, and safe. Because those three words, if you're going to have any type of like, inspiration or mentor ability, those are definitely words that you should be focused on or impacting. That's so, so good. Okay, Dr. V. If you could change, by the way, this one doesn't have to be 10 seconds or less. None of these have to be 10 seconds or less. But if you could have a magic wand moment, if you could change one thing about how women are supported in this industry or just in the world in general, what would that thing that you would change be?

You know, it's interesting. The human species is the only species that actively pretends that the female, female of the sex is weaker. That's very unique to us. And I would very much, if I had a magic wand, want to give safety to those that identify as male that are participating in the narrative of it of women being less than. And I think in order for that to happen, the underlying wish is for safety. You know, I, I, I wonder what it would be like to walk past a van in a parking lot and not question, maybe I should walk a car over. You know, I would love for women not to be underestimated. If I boil it down to one sentence, I think I would really like it if idea of the hysterical woman was diminished and the idea of the hysterical men was increased, you know, so that there would be parity, so that there would be balance. I think that this whole concept of capability being determined by sexual is the most ridiculous and the most easy to change challenge we face as a species. It just doesn't, it biologically doesn't make sense to think of women as weak or less capable when we endure the most painful experience of childbirth, it doesn't make sense for, you know, just because men can lift heavier things, it doesn't mean that's all, that's all they're good for. And just because women physically may not be able on average to lift as heavy things, doesn't mean we should never have the opportunity to lift them. I, I don't understand this need to demonize or add this fragility to one sex over the other. And it's baffling to me, and I. I don't have a reconciliation for it that makes sense.

It's interesting because when you said the words like lift these things, my brain did a very interesting thing. And that's part of what I love about these conversations. Just sharing kind of sometimes where my brain those. When you said the word lift these things, I literally in my brain went physical, mental, spiritual. Because it's not just about, like, I don't want people to think of, like a gym scenario with what Dr. V said, like emotionally lifting the thing that needs to be lifted in the moment when you're in the middle of a boardroom or spiritually needing to lift that thing because somebody came to you with a question that is like, so rooted in who they believe they are because of where they came from. Like, these things have nothing to do with the sex of male or female. So Good. Okay, so Dr. V, this is literally called the women of HubSpot. So I have to ask at least one HubSpot related question. And so I'm super curious if there's any particular tools or strategies or trends in HubSpot that might excite you right now.

I mean, the AI integrations are pretty wild and wicked, and I love to see them, but that's such a broad. HubSpot does so many things, and it is just an incredible tool, especially as you're a young business starting out, just to be able to organize all your information. I think the, the thing that is most enticing about HubSpot is and will always be it's just easy to use. It is just an intuitive, easy to use product. And if you get expertise from someone like you or someone like lift enablement to really set it up and craft it so you're not cobbling it. It's just an amazing tool that almost gives you like this entire staff of people with the click of a button. And I think that that is a phenomenal thing. And I think when Dharmesh and Brian started with this idea and made this, it was truly the most purely unadulterated tool you could give to a business to maximize your impact with limited resources. And I think the ethos of that is just incredible.

Yeah, I love this, like entire team of humans with a click of a button and maximizing your impact. That has been a kind of storyline through this journey of HubSpot since, you know, 2010, 2011, 2012 especially is kind of when it started to take off and inbound and things like that have happened. So I love that. Dr. V, you write books, you were mentioned by multiple women in other episodes that we've had of this. You're out there on LinkedIn and in spaces and you're presenting yourself. So I'm super curious on your thoughts of, like, how important is networking with other females or just even networking in general? And are there any certain strategies that you use to kind of try to build these connections along the way?

That's a great question. I think connection is important and that is what networking is. A lot of people get very nervous when you start talking about networking. I think it's connection. One thing that's really interesting about me and think that the pandemic probably exacerbated this. I'm really quirky and in large groups, especially if I'm not on the stage, I'm like, I don't know what to do. Do I say hi? Do I say not hi, like hi, you know, And I do all of these things to make it easier for me. I wear bright colors. I. And I've done that for a long time. I try to lead with a smile. But I think that everyone deserves a space where they can tell their truth. And networking should be a part of that, that community building. And look, not everybody's going to tell their whole truth the way I tell it. And I'm not saying that that's the right way. It's the right way for me. But even showing up and saying what you do and what you're good at and introducing yourself like that is telling the truth. And I think that networking and community is so critical. And I think especially for underrepresented groups, in this case women, it is important because when you, you know, if you sit back and you imagine yourself in a room full of anyone other than what you are and you are the only one, you get a glimpse into what it's really like to be in one of these marginalized categories. And just seeing someone that looks similar to you, that changes things. And I think that networking is a part of that because you will see someone that looks like You. But when you learn about that person and you learn how that person is like you, that just adds more scaffolding, more solid ground, more of a solid state to climb from. So that's why I think it's important, and that's why I forced myself to do it. Even though I'm probably the most awkward person you're going to encounter in real life.

Too funny. I love this idea that you boiled it down. You kind of jetted away from networking and boiled it down to connection. I love that it's about the truth, like, your truth and how much you're willing to share of that. But this idea of, like, seeing that their others are like me and I don't feel like the only quirky one or whatever type you are on the planet, there's more like me. Okay, then that makes me feel like I can navigate in this world that I'm in. And I love how your questions. There are threads that you could grab and go super deep on these kind of topics, but yet you're able to just give this overarching answer that for my brain and hopefully the viewers and listeners, you're like, man, I want to listen to this. And then, like, dig even deeper, which, by the way, again, maybe get the book or books, and then you can dive deeper into Dr. V's brain as far as that goes. Okay, I'm super curious, and I always love how people kind of step back and think about this one. You've been on a heck of a journey. You're out there being authentic. You're telling the truth. You're trying to, you know, build the best life that you can have for the people around you. What so far has been the most rewarding aspect of your career, this is.

Not shameless self promotion. The books, you know, look, here's the deal. I don't know what anyone else's high school experience was like, but mine was treacherous. It was treacherous. And college was treacherous also. And, boy, have I had some relationships that I wouldn't sign up, even my enemies, for, like, real talk. And these books, that one and that one are kind of like the comeuppance, you know, that what you would have said, or I should have said, or wait, I would tell him or her or them, whatever it is. Like, these books are, are for me the ultimate equalizer. Like, they're justice. It's like the scales were hella unbalanced and now they are put right. That's what writing is for me, because I'm just telling the truth. And to have the Privilege of telling the truth and it being factual for me, unapologetically, just saying it, saying everything but your name and you know, what you did. I mean, like, that is so rewarding. It is so gratifying. And it just. It's like pounds just shed off. Weight just goes away. And it feels like justice. That's what my writing feels like. And the fact that me sharing what I have been through, especially. Especially the parts. Not even the parts, but especially the parts I'm not proud of, and that it might prevent just one person from making 1% of the same choice that ends so badly. My entire journey has from about 40 on, it's been just about evening up the scales. Like, you got single mother, food stamps, stripper, felon. What can we put on the other side? And these books just feel like they're starting to even that list out.

And I just had a mental moment, if I'm being completely honest with folks, because I too have this. This line I've drawn in, drawn in the sand of like Dirty George versus Good George. Trying to repay the penance of, like, what I did as a younger man and kind of what I bring to the world as an older man. But also you. You gave me a mental moment where you talked about the scales were hella unbalanced. And my writing of the books is justice because I have a book in me that I know I want to write, I know I'm supposed to write. But I've always kind of gone from the I'm a writer perspective versus, like, what you just said, which, by the way, are kind of two totally different things or paths that would start the way or the direction in which you would actually write that book. So, okay, all right, I'm going to have to rewind. That's my rewind spot. I'm going to have to go back and just re. Listen to that again.

I am not an author. I'm not a writer. Yeah, I'm a felon. I'm a stripper. I'm a single mom. I happen to be able to tell the truth. So people that are thinking that every story is so important, and I truly believe we're here just to literally have experiences. That's the only thing that makes sense. Good, bad, or indifferent. Like, that is the through line of everyone here is we are having experiences. I'm just sharing those. So I, I encourage you to just show up one day and just even voice the text. Don't even write it, but tell your truth, because it could help someone and you deserve to be heard.

Dr. V, let's. Let's put you in mentor mode, which, by the way, you wear very well, but let's put you in mentor mode for a second. And what advice would you give to other women who might want to choose this type of career path as. As they kind of move forward?

Career path or my career? Truth telling, which career? First of all, don't follow me. You don't need to follow me. There's no value in following me. There is a value in walking your own path and maybe picking up the lessons that other people have shared. So you don't need to be me. The world does not need another me, but it desperately needs you. Do that which you can afford and nothing more. And I mean that. A lot of times people will come to me and say, I should do this or I should. No, you should get that job so you can hire more people like me. You should remain silent on this. You do not have the social capital to fight this battle. This is not your battle or this is your battle. Here's the most strategic way to go about it. There is no honor in losing a job you can't afford to lose. There is no honor in passing on an opportunity because maybe you're a white male and you want a woman to have it. Please, whitemail. It's okay if you get that job. Just hire some women after you get it. You know, there has to be a balance between what you sacrifice and what you gain. Please don't pay more than you can afford for shoes, for handbags, for food, for restaurants, for your career.

Okay, so we're going to land the plane. I've got three questions left for you. These are what I like to call kind of the mountaintop questions. Number one, you've been on, again, one heck of a journey. You've done some amazing things. You're literally sitting there with a dope background. Two great books. So you got here. Now, Dr. V. What are your long term goals?

Number one, I'm very suspicious. Like, I still have my goals under here where nobody can see them. Like my wish list. I was like that even when I was a seller at Groupon. They'd be like, how many contracts are you going to close? And I was a pretty quick closer. Not necessarily big deals, but very fast. And I'd be like, I don't know, I can't tell you. And they'd be like, well, you average four a week. I can't tell you. But I would always have a number in my mind. I would love for everyone to hear Someone say that they represent a category that they are most ashamed of. Personally, I would love for everyone for the worst thing they did to see someone successful say, yeah, I made that mistake too. And I'm still here. And I'm not apologizing and I'm not asking for forgiveness. Except if you've entered an individual party, right? If I can be a part of that, I think that would be phenomenal. Because when somebody reaches out to you and says, you know, I have a felony. Also, I've been hiding at work, you know, my mom was a stripper also, and I'm. I'm finally not embarrassed to say that to someone else. Like, I think that anything that I can do to lift the shame of someone's chosen experience, and you chose it in some shape or form. Right? Like, we don't really happen stance into much. There are some things, but that is my long term goal. So if that means that everyone reads one page of my book or sees one of my LinkedIn videos or sees one post, whatever that is, that's. That would feel like success for me.

So good. Which by the way, I'm gonna circle back around to that success statement here in a minute because literally that was about your long term goals. Question number two. And by the way, we learned a lot about you immediately as soon as we started the interview or this conversation. But what is, what is one surprising or little known fact about you that people might not expect?

I'm really boring. I'm really boring. When work ends today, I will put on like, sweats. I try to make sure they're clean sweats just for the benefit of my husband and my cats. Like, so I'm not disgusting. I bet the cats wouldn't care as much. And I'm gonna do puzzles on my iPad all day long. Puzzles. Like, I do puzzles all day long. I will sit in bed for hours doing puzzles. I am really not that exciting. Even though the book is like, she did what? Yeah, I'm pretty boring.

It's funny because people do get this perception of like, well, what the life must be like of somebody who is this person. And I love that you're like. It might surprise you that I like sweats and puzzles. Like, that's, that's it right there. So good. Okay, last question. As we land the plane, finish this sentence for me. Success to me means blank.

Helping others, telling the truth, representing showing up when you are the only one, and being unapologetic for the choices that you've made, except when they impact other people negatively in which case, you owe an apology.