Ep # 99 | Build Something From Nothing


HitchSwitch was born of an entrepreneurial spirit and the desire to make life easier. HitchSwitch founder Jake Wolff was in his first year at Fordham Law School, where he toyed with the idea of starting a business and hoped to experience his "Eureka!" moment. As most good ideas come from real life, when Jake got married in 2010 his wife wished for easy, step-by-step instructions to simplify the name change process, and HitchSwitch was born! Jake believes no one should ever wait in long lines at multiple government offices, only to find out they completed an outdated name change form. He sought to create a website where one could quickly and easily change their name after the 'big day,' while eliminating all the hassles associated with locating and completing the necessary forms, and the piles upon piles of paperwork. Since the founding of HitchSwitch, the team has had the pleasure of guiding hundreds of thousands of newlyweds through the name change process. 



Shantel: Hi Jake, welcome to the show.

Jake: Hi, thank you so much for, for having me. It's great to be here.

Shantel: Of course. We're really excited to have you. I selfishly just got married, and I got a gift card from a colleague for your company, so I'm eager to hear a little bit more about it and how to use it and what you're all about. But I know our listeners are really eager to hear more about your company as well. Let's just kick things off with sharing a little bit more about Hitch Switch, and then I also just sounded like, I think I stuttered on that one. May need some more coffee. Let's talk more about your company and tell us what it's all about.

Jake: Oh, absolutely. Well first off, congratulations. And we look forward to assisting you whenever you're ready. So-

Shantel: Thank you.


Jake: That'll be great. Well, I guess sort of the genesis of Hitch Switch started when I was just graduating from law school. I was an attorney at one point in my life. I was working as ... We're based out of New York City and I was working for co-ops city, which is a housing complex in the Bronx doing landlord tenant stuff, which really was not fun at all. And, yeah. Oh it's ... the stories there probably beat the stories here. No, that's what when I literally came home from work, I was married for about six months and my wife said she wanted to change her name but had really no idea where to start. I smiled and looked at her and said, "You're a genius." We started looking into this. Saw there wasn't really any other services out there that assisted newlyweds in this project, or in this sort of task I should say. And did a little more research, sort of used the legal background to compile the forms and research, and data, and gave my notice maybe about a month or two later and said to myself, if I'm going to do this, I can't have a fallback plan. And I opened up Hitch Switch 2012. In May of 2012, so about seven years ago, and I've been lucky, I haven't had to have a real job since and we've had the good fortune of helping over 500,000 newlyweds at this point navigate the complexities of changing their name.

Shantel: Wow. A couple of questions coming to mind, but first, it sounds like you knew a great idea prior to even understanding where the industry stood as far as competitors. Like your wife said, "I want to take my name." And you're like, "Wait a minute, light bulb." Was that actually the flow, or did you guys do a little bit of research on how to do it and then you recognized, well there's no easy solution?

Jake: No, it's really the former. I figured she wasn't, and my wife's name is Lauren, that Lauren wasn't in sort of a bubble by herself in this situation. She's a master's level educated person. So you'd figure, she could figure something like this out, and I just saw how, literally it was within that like half hour parish was like, "I'm not going to change my name. This is driving me nuts." And that's really where the idea came up, and we took it from there. We didn't do, or I didn't do much research to see if there is anything like this out there because the last thing I ever thought I would be doing was probably something in this sort of wedding related realm. I just knew that she wasn't the only one out there. Again, speaking to some friends and just starting doing the research side of things, I saw that there really was a gap in the market and that's where it came from.

Shantel: Wow. So you quit. I mean, I imagine attorney, stable high salary job in New York, a month after this idea. I mean, did you already have revenue coming in the door from-

Jake: Nope.

Shantel: You were just a newlywed? Okay, so you just were like, I'm going for it. I have to be all in or I can't…

Jake: Exactly. I figured that if, just as you were saying, when you're lucky enough, especially this day and age, to have a stable job, if I weren't going to go all in on this, I knew I could always, go back at some point in my life and practice law again. But I knew that if this is what I wanted to do, it had to be like, all right, all in or, or all out and it would crash and burn. But I was lucky that it's really all about luck. Lucky that people love us helping them. They have a need for the service and yeah, it's really where it's at. But ...

Shantel: Well, I mean it sounds like you have an amazingly supportive new wife. I mean, when you, the seven years ago you're like, "Hey wife," or, "Lauren, I'm going to quit my job and start this company." Did you, and this is going to be a little bit personal, but did you give yourself X number of months to try to figure it out? And then you would go look for another job? Did you have savings built out? Did you need you have a lot of ... I mean did you have a lot of expenses up front and starting this? I guess I'm thinking logistically.


Jake: I guess I'll start off. The good thing about what sort of a business like this is unlike sort of like a brick and mortar business, there was really no overhead. The initial investment was $5,000 that we invested in this. I built the initial website off of WordPress. I knew nothing about any type of coding. I was literally looking at blogs on Google and just Coding 101, essentially, to sort of build out this basic website where even though it looked okay at the start, everything behind the scenes was sort of a manual process. The order would come through. Unfortunately, I have the world's worst handwriting. And so those first couple of orders that came in I wrote by hand and it was, compared to where we are now, it was an absolute mess. Truthfully. I laugh at the first client and say, "What the heck are you doing here?" But in terms of the supportive wife, that, listen, like without, she was just incredibly supportive. She knew that I always wanted to do something on my own. Nothing really ever sparked the interest like this idea did, and we had some savings. Not a lot. I didn't really give myself a timeframe because as, it sounds crazy to say now, but especially now that I have two kids, we didn't have any kids at the time. We were living in a one bedroom apartment, so there's wasn't really much overhead either. I didn't really think about the long-term vision of it because I just said to myself, "This is going to work." And sometimes blindly, sometimes I guess maybe a little bit of Hubris, whatever it might be. I just sort of started going and sort of running with it. But yeah, without, listen, without Lauren, she was literally the only one at the beginning who believed in this. My parents are always incredibly supportive, but they're "old school" and I'm using that in quotes, in the way they think about things and they were like, "What? You're going to change names? What are you doing?" And I laugh now. Seven years later, my dad says to his friends like, "Oh, look at Jake's business." And I just chuckled to myself, but she was the one who said, "Just go for it. You know, you can always go back and do something else if you have to." And then sort of at that point when I left my job to pursue this, like I said, I didn't have kids. Would I do at now? Probably not. Because when you have children and other expenses and life is there, it's scarier to take that leap. But at that time I was like 28, 29 years old, and I just like, all right, let's do it. That was a great question because when you make me think about it, I'm thinking now as almost 37 like, "Ooh, what was I doing?" But at the time, none of those thoughts crossed my mind.

Shantel: Yeah, no, I'm glad you said that. I had a recent conversation on another podcast and it was just all about risk and kind of my appetite for risk and thoughts around, do you think that as you get older that goes down a little bit? And I started the company, Gosh, I guess I was like 23, 22. Quit a corporate job. I mean same kind of scenario and now thinking about that of like, we're buying our first home and about to have a first mortgage and want to have kids and it does sound a little bit more scary to just like go out on a limb and take a chance. But it doesn't maybe scare me as much as it may someone else because I know what is possible. But was Lauren involved early on? Does she have a role in the company now?

Jake: Right now she doesn't have any sort of an official role in the company. She's always been behind the scenes. She's ... just has incredible ideas with certain things. I always, if there's something that bothers me, she's still always my first call if there's something that I want to do, and just sort of bounce it off her, but nothing official. Just sort of unofficially, I would say.

Shantel: Now, you did say you always wanted to have your own company and she knew that and kind of poured into that. Did you grow up in a family of entrepreneurs? When did that idea start to trickle for you?


Jake: Really as early as I can remember. My grandfather came over here from Europe. From Germany before World War II, and he was an entrepreneur. He started off in the premium business, which I don't even think exists anymore, where if you opened a bank account and put $100 into your savings account, that bank would give you, a gift of a set of dishes. I don't know, whatever those little incentives were. And so he started selling to the various banks, built up a business that way. And he was always very entrepreneurial. And that's something that I always sort of saw growing up. It's something that I wanted to do, even though I really, when you're young, you don't really understand it, but it was always just having, and wanting to do your own thing and taking the risks in a positive way in that regard. And it was watching him really was an inspiration for me to do this. And then, like I said, my father is more traditional, but I guess in his way he's an entrepreneur as well. He has his own company and Hedge Fund. I don't even understand what they do, really. It's something in finance. He's a numbers guy and while it's a traditional business, he started with my uncle 30 years ago, whatever, whenever it was. And I guess that's, thinking about it now, obviously entrepreneurial as well, so I've sort of always around that. A funny story: when I was when I was little, I used to go around on the golf course and pick up golf balls and then try to sell the golf balls on the street in front of my house for like a dollar or two. I remember every time. This sort of thing just always enticed me. I always knew that I wanted to do something like that. And I always would say, "It doesn't matter what the business necessarily is. I just know I want to do something in this role. Build something from nothing." The thought, and what gets me excited a lot about this is that when you think about it, or when I think about it, and I go back to when, before we had an office, when I was sitting in the bedroom. Our first offices in my parents' house, so sitting there by myself staring at the screen, crossing my fingers that orders would come in. To look now and to see that something has been built over the last almost seven years. That's really what I've liked the most about it, and the fact that we've had, knock on wood, success happy clients. Of course, that's really what makes it fun every day. And being able to do this and getting up and doing what I love. It really doesn't feel like work. I know that sounds very cliche, but it's the truth.

Shantel: Well, I love that you shared that. I think it's always fascinating to hear what inspires people to have their own business. And I certainly relate to growing up in an entrepreneurial family and it's always fun because I tell you all the great things. That you could be your own boss and make your own hours and being in control of your own destiny. But they oftentimes don't talk about, the times you have to fire your first person or you have to figure out something with a challenging client. And so I'm interested to hear from you, what's kind of been something really challenging or surprising that maybe you weren't prepared for or you've learned a ton from?

Jake: Yeah, no, you really hit on the nail on the head right there, that the ... The head on the nail, excuse me. I'm just thinking about it. What would I want to say? I never thought I would. Right now we have seven employees. The good thing again about what we do is, it's not brick and mortar. We don't have inventory. It's all done online. We ship packages out by everything now, like I was discussing earlier with my hand, everything is automated. The shipping is linked in our backend that we've built out and I have real developers that work on this now. I'm not piecing things together.

Shantel: You're not coding anymore?

Jake: No. No, no, no. It's like a child's art project. That's what I'd always compare it to. It's like just piecing together random sorts of things and it may or may not work. But when I started this, I never thought just because, and I'm sure you probably felt the same way, that you just think about making the business in some ways a success, and you're just motivated to try to grow it however you can. I never thought I would have to manage people, or you said have to, unfortunately these are the way things go, fire people, or if an employee had ... An employee, I remember, a couple of years ago had an accident and we had to put her on disability, and there are all the rules and laws and it's all those sorts of things that sometimes could take away from the, as I was explaining before, the fun part of things. I definitely was not prepared or able to manage people when I first started this. I remember our first employee. She's now gone on and actually opened up, a while ago I remember, a business of her own. I haven't kept in touch with her really, but the way I managed her, to now the way I'm able to manage people today and that my staff, the core staff of like four or five been with me now for three, four years and the way they're able to start managing some people is definitely took, especially for me, that's something you never think about. You think about the business side of things, at least I did, the business side. Oh, how am I going to make this work? What are we going to do? But of course in any business you see things. And if you're a one man or one woman show, most of the time it's not really successful because you don't know how to delegate. You can't give your employees who are there for a reason, who are typically great employees, and able to do the job very efficiently, if you can't delegate it and teach them and show them, you're just going to take too much on because the business inevitably grows. But as I was saying, managing, it's just something that I definitely, I wish I had a video camera almost in my office so they could've seen the way I interacted with the one employee at that time, and sort of the way I think I've gotten better now. But it's definitely a great point. You don't think about those external factors that go into building a business as well. It's not just about the sales or the awareness of the clients. It's if you build something hopefully that is successful, that you have people involved. And with people, everyone has different reactions and managing is definitely a skill that I've definitely gotten better at. But that's one thing every day, I just want to keep improving because it's definitely an integral part of what we do, because if your people, if your staff, your employees aren't motivated, it shines through to the clients, to partners to whatever it might be.

Shantel: I definitely agree with you there. I think and we hear it a lot on the podcast. The people piece is certainly in those challenging and I'm always learning and growing and it's like throw any other problem at me, like a process or a system problem or client problem and it does not phase me, but a people problem or like a challenge that we have to deal like interpersonally. Oh it just, it is tough, especially as we've gotten bigger and like we have a team of 20 and it's like everyone has different personalities in different ways that they like to be coached. And it's a fun challenge for sure. But it's definitely one that sometimes keeps me up at night.


Jake: Oh, listen. Absolutely. And I'll share a story if you don't mind. I would, something challenging, I guess sort of a real example that your listeners might be able to, if they're thinking about starting their own business or started, that you think about. In this day and age, everybody is, I guess a buzzword for a lot of people is equity. Oh, you're working at a startup or you should get equity. Everyone thinks that. You hear the stories of like the secretary of Google when they had their IPO getting $10 million. So while younger people today sometimes think that, oh, that's what you need, that's what you need. And I remember that I had an employee who's no longer with us and talk about staying up at night and this employee was fantastic. I mean, did everything excellently. But at the end of the day was just in a support role that supported the clients. They didn't bring in business, but they were amazing. And I remember one day, a couple of years ago before Christmas party, I sat down, or she wanted to sit down with me and we had a conversation and she said she wanted equity. You always think that you hear these things, but when you actually hear in a person, you're like, "Okay. What does equity mean to you?" I always say. "What do you think? What do you want?" Because a lot of times people don't even understand. They just hear this sort of buzzword. And she was like, "I want 30 to 40% of the business." And I almost started laughing, because it's like in my mind, the reason why I guess laughing and then almost crying, but in a way, because as soon as she said that to me, and she, again, amazing employee, I realized very quickly I had a big problem on my hands. Why? Because either, unfortunately, despite everything she showed excellent reviews, just top notch performer that, by asking for that amount, unfortunately she was living in Mars, and I was on Earth, because that's just not something that people ask for. And if that's something she really wanted, I realized I'd have an employee on my hands that would never be happy no matter what because she would always feel that she was underpaid and undervalued. And that was definitely something that kept me up. Lots of conversations about that. And again, in this day and age you always have to, I always say, and as I wasn't that good at at the beginning, but as you get a little bit bigger, on that note, always keep notes, even if it's only in an internal memo about what happened, because in this day and age, while you have a conversation like that, you never know what the other party might say if they said, or to say something crazy about me or about Hitch Switch, or who knows what would happen? So I always obviously marked that down. But when I had that conversation, I was shocked, and I was like, "Whoa, this isn't good." So, actually what ended up happening was that she ... we had a couple conversations over a month or two period. And during that time when I was still deciding and speaking to my board and figuring out what we wanted to do because I do want to reward our employees with compensation and anything else. It's just when you have someone whose reality is so far out in right field, it's difficult situation to deal with, so eventually she ended up moving on very amicably. But that was something that for a couple months was just like, it's not fun to deal with those real-world scenarios. And at that point we were two, three people in the office. And if I'm worrying about that for a little part of the day, it's like business isn't being handled. So it's all ... it's those curve balls, I guess, that when they're throwing at you and you don't expect it. And because people see, everyone always sees, as they say, the real success stories. Google, Facebook, whatever it might be. But for every one of those, there's 500, 1000, I don't even know. I'm just throwing numbers out there of businesses that don't succeed or if they do not to that level. And it's just, dealing with those situations is something that, like I said, I wasn't equipped to do. I've gotten better at it and I'm always learning to continue. But that was something that was definitely shock value when it happens.

Shantel: Oh, I bet. We kind of looked back on some of our conversations, or just challenges like that, and it's hard in the moment, or like really kind of stretches some of those muscles that in trying to like research. Well, what do I do in this situation? What's the legal HR approach? 'Cause I don't come from an HR background and it's like thank goodness they happen cause they always make us stronger and better equipped to handle that in the future or communicate things differently. Yeah, that, it's tough. I have a couple of more questions just to wrap things up. I love what you said. That you love what you do and you wake up every day super pumped for it and I think that's awesome. And I imagine your role in the seven years has changed quite a bit. You were working from your parents' house, and I have a team in an office and also I think it's interesting that you didn't get into the wedding business because you said you loved weddings. Like it really was just an idea. So how do you continue to infuse passion and purpose into your day to day as one: Your role has shifted, but also you're in an industry that, I'm not saying you don't love it, but you didn't go into it because that's all you dream about.


Jake: No, of course. And I always laugh because my wife always will joke around with people when they ask or what I do. She'd be like, he showed up at our wedding. He really didn't do any anything else. And so to be in this situation. She once heard me, I don't even remember, talking about like Calla lilies to somebody when I was on the phone with them. I don't even know how that type of flowers and came into my head. Who knows? Sorry, just getting a sip of water. For me what keeps me, the passion. It's not necessarily the wedding industry. Like I said, it could be anything. And I don't think, no matter what I did, whether it's something in law, in business, in what I'm doing now, it's just the excitement of pitching your product or your service or whatever you're doing to people who haven't heard of you before. Our biggest thing here at Hitch Switch, and this is what always keeps me motivated, is that unlike traditional companies, we don't really have other competitors. I always say to our team and to anyone who asks that my competition is getting the newlyweds, the majority are brides, but some grooms as well, aware of our service, how hard it is to sort of do it on your own and to show them the value of what we do. And that always keeps me motivated because every year there's a whole 'nother group of about two million couples who get married. The majority who still haven't heard about you. That's always there. And then sort of on the other side of things, and this is probably, could be too personal to even share, but I will. I'll tell you regardless when you start a business, and I don't know if you've ever felt the same way. I always feel I'm only as good as my, as my last day. So every morning I really, and it's not as bad as it used to be, but I wake up and I'm like, what happens if we don't get any orders today? Thank God that doesn't happen. But it's always in like the back of my mind, and the fact that even though it's been a substantial amount of time, almost seven years, it doesn't feel that way. And so every morning I truly wake up and being like, all right, it's time to go attack, see what we can do better. Look at how we present information on the site. How we check people out through the flow of the site, look at all sorts of analytics, look at how people interact with certain clicks here and there. It's all that always keeps it going. And we use a lot of, whether it's Google Analytics, whether it's other programs, so something like Mouseflow, we use a lot too, to track the heat maps of how people interact with our site. It's just all of that keeps it going. And that's what makes me so passionate. Just that again, it's building something from nothing and also the fear that, what happens if tomorrow at it goes away? So it's always sort of staying on my toes, I think, that that keeps me inspired.

Shantel: I love that. I also feel like if any listeners recently got married and ever tried to navigate any sort of government website, they will easily feel that pain of trying to do it themselves and come to you right away because it's horrible. So we're certainly excited that you guys exist. How can people get in touch with you? Learn more and change their name?

Jake: Oh, awesome. They could go to HitchSwitch.com. H, I, T, C, H, S, W, I, T, C, H dot com. Check out the site, see our three different services that we offer. If you ever have any questions, our email is customerservice@hitchswitch.com and our phone number, I'm old school too and that one, I still try to use the phone as much as we can even though a lot of it, it's obviously, goes through email and live chat, but our phone number is eight, four, four, new name. (844) 639-6263. So anybody could reach out at anytime with any questions. It doesn't matter. We've seen pretty much, I would say every sort of iteration of a name change that one can go through. So even if they're not a client or don't want to use our service reach out. That's why we're here. At the end of the day, it's exciting because we reach people at a certain exciting point, like a change in their lives and at our core as a service business, we like to give back however we can to clients and non-clients alike, because as you said, it's just a pain to sort of do it on your own.

Shantel: Well, thank you so much for sharing that. We'll definitely be sure to hyperlink in the show notes. Thanks for being on the show. We loved having you on.

Jake: Thank you, Shantel. Thank you so much.