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Steve Dean once put a sign up in a NYC park offering “free dating advice.” Learn how this ADHD super connector became a dating coach who helps people find love. And get his surprising advice on how to find your own unique career path. 

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Episode transcript

Eleni: From the Understood Podcast Network, this is "How'd You Get THAT Job?!," a podcast that explores the unique and often unexpected career paths of people with learning and thinking differences. My name is Eleni Matheou, and I'm a user researcher here at Understood. That means I spend a lot of time thinking about how we find jobs we love that reflect how we learn and who we are. I'll be your host.

Steve Dean is the founder of Dateworking, which offers dating industry consultations, relationship coaching workshops, and experimental events in New York City. He also has ADHD.

So, Steve, you're a dating coach and a consultant. What does that mean?

Steve: OK, so I guess it starts with helping people navigate the 3,000-plus dating apps that are out there and all of the different possible relationship permutations that they may find themselves in.

And so, I work with individuals in order to get them either on the right app or just going to or hosting the right events to bring the people they're looking to meet into their lives. I help them craft profiles and make good photo lineups that capture and distill their personality into this weird two-dimensional space.

We call it, like, the internet of dating things. There's apps, there's services, there's matchmakers — it's across the board. There's so many apps. I have 250 of them that I've made profiles on. I have 150 on my phone.

Eleni: Whoa, 150 apps on your phone!

Steve: It's overwhelming. And for a lot of people, they download two and they're already exhausted.

So, I help people, first and foremost, with their entire dating lives. And then when it comes to me getting frustrated with all the apps that I'm using and being frustrated by and seeing my clients get frustrated with, I then turn around to the industry and I say, "Make better apps." And so, I used to work in mobile strategy, so I can advise founders and CEOs on how to build a better and more compelling mobile experience for the daters, who I'm also serving.

Eleni: Awesome. So, 150 apps on your phone. How do you keep track of all of that? 

Steve: Honestly, I wish I had a good answer for that. I do bucket them into over a dozen different folders. For me, I have standout apps that don't have to be in a folder.

They're the ones I'll access most regularly. And I find them to be most compelling. And they're usually the ones I'll refer to my clients. But then there's other apps, like some for creativity. So, if you're not necessarily looking for your one and only but you are looking to entertain yourself a bit, there are apps where you can draw a picture as a first message rather than having to use any words. You can just send, like, an artistic rendering of something.

Eleni: That's pretty cool.

Steve: Um, then there's apps that are tied more to the instant gratification of, like, video. And so, you can jump right into either a video or an audio chat room and begin engaging with people. Or, you can just use video profiles as the lead.

So, it's almost like the Tik-Tok-ification of dating, where you can just scroll through different people's video profiles. And there's just so many possible options for how to engage nowadays with other people in a romantic or even friendly setting. And I honestly wouldn't know quite how to begin because there's so many possible options.

Eleni: I think there's, like, an interesting connection between how people think and learn differently, and those sort of styles. Is that something that you think about?

Steve: In terms of the dating apps, I don't think that any dating apps are particularly good for people with ADHD, because they're already designed to be hyperstimulating and to keep your attention and to give you almost, like, that tunnel vision, where you can just get stuck swiping forever.

So, one of the things that I check in with every one of my clients is how they prefer to engage with tech. Because some people absolutely hate it. They hate typing. They hate having to record anything. They hate uploading things. And for those people, it's frequently the case that I'll say, "Let's start with the offline component, let's start with finding events in your area. Let's start with understanding how your friends refer you to people to possibly date or be romantic with." When it comes to the apps themselves — when people have already established, like, maybe they hate hosting events, they're too nervous to attend events, and they're too busy, so they just want to be very passive about it and let the apps do most of the filtering and searching — the question then becomes, like, how do you best see yourself getting distilled into that two-dimensional space? So, are you better with video? Are you more dexterous with taking good photos? Are you a writer and you really enjoy writing? And so, for you, maybe there's a profile with no caps to the number of words you can use to describe yourself.

Ultimately, my job here is to ensure that someone has the best possible experience and that they meet the people they're looking to meet. And so, part of that experience is knowing, like, how do you interface best with one of the apps that's out there, or maybe a couple? And since there are so many options, it actually makes my job a little bit easier because I typically can custom tailor, like, someone's experience to an app that really works for them.

Eleni: Yeah. I love that. So, how did it all start? What first inspired you to get involved in the dating industry?

Steve: In 2010, I was trying to date on my campus. And I got so overwhelmed by the process of making eyes with people on campus. Like, identifying people I would be interested in and then having to go through that process of understanding: Are they single? How do I find that out? Do I have to approach them and inconvenience them? And I don't really want to be in the position of just, like, asking people that all the time, because it feels like an awkward way to even start a conversation. So I went online to OkCupid, and I really enjoyed the process of answering questions about myself and learning more about my preferences through that.

But I ended up going on one date, my first-ever online date with a 99 percent match. And then we got into a five-and-a-half year relationship from that. And so that was my first big "aha" moment, because I realized that dating apps could take literally millions of people from all around you, who you otherwise wouldn't see or know anything about their lives, and say instead, "Here's all the people who are most likely compatible. Here's all the ones who are available right now to respond to a message. Here's all the ones who you're interested in." And it distills a million people down to the one person on the screen. And you went from not knowing anyone around you to having the perfect person right in front of you.

But then after college, I moved back to my hometown, which is a one-square-mile town. I go on OkCupid, and there might be three total users in my town. I go on Match; maybe two more users. And 50 apps later, I'm still struggling to find are there any people around me on these apps? But originally, I really went heavy into the dating industry because I was basically in this confined space trying to date and having to go to each different app there was in order to find out if anyone was even on here. And then by the time I moved to New York, there were suddenly hundreds of people on each of these apps, if not hundreds of thousands of people on each of these apps. And it just became much more obvious to me how powerful these tools were.

Eleni: Yeah. There are so many entrepreneurial stories that start with trying to solve a problem for yourself and then seeing if that applies to others as well.

Steve: But the reason I got into doing paid dating coaching is that a friend after talking to me for about five hours about her ex, she was, like, "Steve, I pay my therapist over $100 an hour to listen to me talk about my ex, and I just talked to you for five hours. Like, you need to capture this. Like, either I wasted five hours of your time or I need to pay you for this time, because there's no reason you should have been the one listening to me for five hours."

Eleni: What a good friend.

Steve: The fun part is that it's also been an iterative process. My first profile wasn't that great. And I've now made over a thousand updates to at least my OkCupid, but then, you know, for the other 250 profiles, each of those, I update on a —

Eleni: So much work.

Steve: It is a lot of work, and that's partially why I am better able to serve people, though. It's because I've done the work of being annoyed at every step of the way for every app in order to know, at the very least, is this worth using? Is this one that will help people?

Eleni: Well, I'd love to hear more about what a typical day looks like for you, and also, like, how ADHD shows up for you at work and in your day-to-day life.

Steve: Oh, man, I feel like you didn't even have to ask the second one because the first is going to reveal it very quickly.

So, I have, on a typical day, like, I've learned to do a much better job throughout the pandemic with establishing boundaries on my time. And as I transitioned primarily into coaching, I now have only three days a week that I formally do my coaching, and that's like Tuesday, Wednesday, Thursday.

So, I've actually managed to save my Mondays and Fridays for other work and other projects. And without that, coaching could easily just take over my week. And so the way my days are structured is that I let my clients book on my calendar for a finite range of times during Tuesday to Thursday. And so that's really all I focus on those days. Nothing else can really enter the calendar other than client calls. 

I let my Mondays and Fridays be the days when I work on all the other projects that are in the queue. And that's where the ADHD comes in, because there's a lot of projects that I've started and then potentially not finished. I'll make a little bit of headway and then get distracted.

For instance, I have a second season of my podcast for which I've recorded all the episodes and edited about half or three-quarters of the episodes. But that's been like a year of work that has been started and stopped because, in addition to the podcast, I also have been working on several simultaneous blog posts — 160 simultaneous blog posts.

Eleni: Whoa!

Steve: So, it's easy to get distracted from one by working on the other. And it all feels productive, but it's also hard to motivate myself to even choose which one, because it's not like I necessarily feel that any one of them is the most important. I feel like they're all important because they're all responses to real client needs and questions that friends and clients have come up with that I haven't answered to. And I want to give that answer out to the world because it solved the problem. And it's just a matter of now sharing it. But deciding which one to share, which one to finalize, getting to the point of finalization, that's the real challenge. And that's where the ADHD tends to kick in.

Eleni: You brought up a couple true ADHD things there, in terms of, like, starting and not finishing projects, prioritization, motivation. For listeners that might not necessarily be aware of why that might be an ADHD thing, do you want to give your own description or how it feels for you to, like, be experiencing those types of symptoms?

Steve: It's honestly hard to describe. Sometimes I'll literally schedule my day by the hour. As soon as I've started something, if I'm really in the zone with it, then I won't want to stop and then jump into something else.

And so, if I schedule two hours for a blog post, it may be the case that the first hour is me just trying to do some extra research for it. And then suddenly the two hours are already up, and I've yet to type a word. And then maybe I'll have, in the last five minutes, thought to myself, "OK, I can really — I need to get at least a paragraph in."

And then the five minutes becomes 25 minutes, and now I've already eaten into the next time slot. And then I'm in a moment of "I'm going to cancel this next thing, because I don't have time for it anymore, but maybe I can start early on the thing after it." But then I'm in the point of decision fatigue, because I have to now decide whether to stop doing the thing that I was already productive in or start doing the thing that I had scheduled, and in that moment of decision fatigue, I start to get a little bit of anxiety and I lose the motivation to work on either one, because now my core decision is deciding which one. And then I will typically in that moment do some of the dangerous low-hanging fruit of checking. So, by then, I'll probably have received upwards of 20, 30 emails. I may have gotten another 15 to 20 texts. I used to get, on average, 400-plus notifications across the 500 apps on my phone. And that's just on my phone. That's not even my immediate environment. Like, I'm presently cat sitting, and so there's two cats that will happily just come in, want some pets, and jump on my keyboard.

You know, there's a lot of possible distractions that go beyond just what's on my phone, what's on my computer, what's in my immediate environment. I know I've been a super connector for 10 years now. So, there's just thousands of people who may be in my city at any given time reaching out to say, "Hey, let's go get coffee. Let's hang out." There's just so many possible avenues that my attention can travel on. Some of which are considered productive, some of which are distracting but also sometimes produce the exact fodder that then goes into my work. Like, following up on a message thread and going on a creative date can then become fodder for the next article about dates you can do in New York.

And so, it's really hard to know, was this productive? Was this distracting? I'm just constantly in that cycle. I'm glad that I've gotten that out of being a 24/7 problem. Now that I've created the coaching world, where, like, that's three days of my week in which I don't think about the other projects. But what that means is I can only think about the other projects on two days a week. And so, because I've established these healthier boundaries, it's actually been devastating to my productivity because there's not enough hours anymore.

Eleni: I was actually going to ask you more about this time boundary idea. And you said that it's improved a lot, so I'm interested to hear what it looks like before and then what changed.


Steve: There were many moments when I decided this is not sustainable. I think the worst one was when I was sleeping about two to four hours a night, working 20-hour days, navigating to a different apartment every day to live because I didn't have a stable space, going on dates still, amidst all of that.

Those were the moments when I realized, like, something had to change here. And so, little by little, I would try to make changes — sometimes involving slightly more stable housing, sometimes involving trying to sleep more. Always a hard one, especially when I didn't have boundaries with the work I was doing, because if it was the choice between going to bed at 10 p.m. or spending an extra four hours finishing a blog post, previous me would 100 percent of the time finish the blog post. And I'd ship the blog post, and I'd feel good.

Now I've had to come to grips with this idea that some things just won't ship and that's OK. Or they won't ship this week or this year, and that's still OK. It previously was not a thing I'd consider. I think I got used to, from an early age, this idea that the higher the stress of the environment, the more productive I was. I associated high stress and high frustration and, like, physical — like, physiological pain — with "good for work."

And I think that's, like, the all-nighter culture, the hackathon culture of "stay up for two days in order to get the thing shipped" in college. I don't know that I wrote a single paper without pulling an all-nighter. So, like, midnight is usually when people would start going to sleep. And that would mean no more distractions, and so I'd start my work at midnight, and I'd finish it by whenever the paper was due. It was my best way at the time for coping with being distracted by all the things all the time. Just, like, trying to escalate the intensity of the deadline and isolate myself from others so I could get into a zone of focus.

And so now, like, that carried over into my professional life in a way that was sometimes great.

Eleni: I've actually heard this idea of staying up all night from quite a few different people that I've talked to. And often they've talked about procrastinating until the last minute or only really feeling motivated to start right at the end or super close to the deadline.

Steve: And it's hard to find proper sources of motivation, because I found out early on that money is not a motivator for me. If you say I'll give you $100 to do this thing, I'm not going to do the thing. That's not what makes me wake up and say, "This is the priority for today." I'm still trying to learn —

Eleni: I was actually going to ask, what is the motivator?

Steve: Honestly, the — I think I don't like disappointing people.

And so, when I have a calendar event with another person tied to it, such that if I didn't show up, then they'd be disappointed. That would be like my, one of my highest motivators. That's why I liked the coaching work. It's because the core thing that I have to do, my core responsibility, is to show up. I have to be present on the call with the person who's on the other end.

Eleni: Someone's relying on you.

Steve: Yeah. And that for me is really motivating. And as soon as I see that they're confirmed for the calendar invite, I know that I'm going to make it. Whereas, if I make a calendar invite to myself and say, "We're going to work on a blog post from 2 to 4 on Monday," that — I am terrible at respecting my own personal invites.

I might do a lot of other things, which is the weird form of, like, productive procrastination that I've learned over the years. Where I could put two things on my calendar that I'm supposed to be doing. And then I do 20 things that are not that but that were somehow also seemingly useful.

The alternative, and I don't know if you have a word that you might use for this, but like when you put 50 things on a one-day list, none, like, you expect to maybe get done five. I don't know if that's just overbooking or being overeager, overaggressive. Is it trying to add too many things in order to then create urgency because there's so many, I have to start doing some now. I don't know if there's a word for that, but that's a separate problem.

Eleni: And then it comes to the problem of feeling overwhelmed and not being able to prioritize necessarily.

Steve: Yeah. I mean, it may be that I want that feeling because that's what helped me feel like I can get more done. But, yeah, I think over the past couple of months, I haven't gotten a little bit better. Uh, I'll put a few checkbox items for each day of the week and then eventually just get to them.

Eleni: So, you said that you are a super connector. I want to hear a little bit more about that and what that means to you, and how you apply that to the work that you do.

Steve: I look at a super connector as someone who can refer almost, like, a community to another community. So instead of being, like, the head of one community, you just network with a bunch of other connectors. What that means, at least for me, is if someone says, "I need dating help," I'll usually check in and say, like, "Do you also need job help? Do you need help finding friends? Because those friends you find could then help you find dates. And so the super connecting comes in just by having this multidimensional approach where you think not just about one domain of, like, friendship or dating or jobs, but all collectively. And then you think of who are the people who can best be the routers to get this one person's needs met?

These relationships can come from anywhere. In the case of dating, someone who turns you down may be doing it for a very good reason. Maybe they recognize that they're not the right fit for you, given what you both want, but they could then turn around and say, "You should date my friend." If we have good relationships all around us, it makes it really easy for all the people we get to know to, over the span of many years, continue being meaningful and relevant in our lives, by tagging us, by inviting us to things, by even just, like, sharing thoughtful words if we put out a request anywhere. And so, for me, I just, I love that these relationships we build get to continue being fruitful throughout our lives.

Eleni: So, you mentioned unconventional living and cat sitting and moving around a lot. So, I would love to hear a little bit more about that lifestyle and how you do it and why you do it.

Steve: Sure. So, the first, I guess the reason for why is just lack of money. If there, if you don't have the ability to afford rent and you don't have the ability to afford even a hotel room, then the question is what's the next step if you don't want to sleep on the street. And so, for me, learning quickly how to find people who needed cat, dog, or apartment sitting was really useful, because if someone needed a month of dog sitting, that meant I could go a month without paying rent somewhere. It wasn't even like I had an option of paying rent somewhere because, sometimes, I lived for several years on less than $7,000 a year.

And so, I would post on Facebook saying things like, "Who needs a cat sitter, dog sitter, apartment sitter?" And then I'd also asked almost any person I met to just keep me in mind for anytime they hear someone say, "I need a cat sitter, a dog sitter, an apartment sitter; I'm going away."

I want people to associate those words with me so that they can then reach out to me and say, "Oh, good, call Steve." And sure enough, that started happening pretty regularly because I wasn't charging people. And if you want a, like, a dog boarding in New York for a week, I think it goes to like $400 or more a week.

And if I can do that for a month, I just saved someone $1,600 or more. And for me, I can get a place to live for a month and —

Eleni: Pretty good exchange.

Steve: Yeah. The challenge is that some people need it for, like, three days. And then the next person is, like, a two-hour commute away, and they need it for one day. And so, a lot of my time was spent just doing this arbitrage situation of trying to find out who needs what and when, and how do I get there in time?

And I didn't have an apartment. So, I carried all the things that I own just in a backpack. And that was a seven-year span where I had over 20 different keys to apartments around the city, because some people needed things at different times, and with some friends, just, they moved to a new place. And the first thing they do is call me up, hand me a key, and say, "You'll use this later."

And, yeah, I felt like the architecture in the matrix where you have 100 keys. And that's always been, my philosophy is I don't want to impose upon people. I just want to be useful. And let the fact that I've oriented my life toward meeting thousands of people and getting to know their needs.

Eleni: You just made me think, Steve, I'm going away in a few weeks. I might have to call you. Do you think your ADHD helps you be a super connector?

Steve: Honestly, I think it's one of the core reasons why I'm able to do it. And part of that is that anytime I'm procrastinating, my form of procrastination is to scroll through Facebook and find out what people need, because people typically post there with things like, "I'm going away; I need this thing," or "I'm considering hiring a matchmaker; I'm looking for this."

There's so many different categories of relationship need that people will willingly and publicly post about. And it's a really easy way to be distracted, but it's also a superpower when I can just — I've done this where I've set aside an entire day to only be on Facebook, answering people's needs.

And in the span of a day, I can connect 100 people to the thing they need next and in so doing essentially cultivate 100 new relationships and be the point of contact for 100 people. But yeah, I think the ADHD component there is that I allow every new ping to be a distraction that sends me into another rabbit hole of connecting people. Because it's not like there are games, like, I don't put games on my phone because it's too dangerous, that distraction. I let my form of preferred distraction be helping people. And so, every new text, every single message, they are distracting. And my brain automatically goes to them as though they're the maximum urgency, but also the by-product of that is this kind of super connector lifestyle where I can be relied upon by a lot of people to do a lot of different things, and it's formed part of my identity.

Eleni: Yeah. I think it's so cool that you can be there for so many people. So, for anyone listening that's interested in becoming a coach and they have thinking or learning differences, what advice would you give them about where to start?

Steve: So, I think the most important thing to remember is that people are willing to spend money on things that save them the time or effort of having to do those things themselves. And so, I learned this from doing coaching for individuals who, let's say they make $500 an hour, but for them to have to spend an hour swiping on Tinder, they've essentially lost $500.

If they spend two hours on Tinder or, as the average user is seven hours, that can be over $2,000 of lost value if they didn't get a date from it. And so, when a matchmaker approaches that person and says, "Hey, I'll do all this work for you for $1,000." Then the person's going to say, "Oh, of course I'll pay you $1,000 dollars to do this."

When you save people time or save them money, they're willing to compensate you for a percentage of that time and money saved. And so, in coaching, I can essentially tell people, "You might go out and try to start dating; you could be spending 20 hours a week or more going on dates, messaging people, swiping on these apps." And that's a lot of wasted time. And what's also the opportunity cost of you going a year or two years, or in some cases for some of the people I work with, 10 years of just struggling through which app to use, making a profile, not getting matches, constantly swiping, and feeling worse and worse about themselves? What would that have been worth to you? 

Let's say you can save someone a lot of time. So, in the case of — this is literally for any coaching thing whatsoever — if someone's struggling with something for weeks, months, or years on end, you can put a dollar value on that. And if you can help them through that struggle, then you can capture that value.

The main thing is to pick the thing that you want to be teaching or that you know more than anyone else about. Keep challenging yourself to learn more about that, and keep challenging yourself to help people solve their problems. And so, I helped hundreds of people with free dating advice. Literally, even putting a sign in Washington Square Park, like "free dating advice," and I'll put out a little blanket and people can just come and receive advice.

And I get to learn, like, who needs what? And so people will say, "I need help with this thing; I need help with this thing." And I can start learning, here's the common things people need help with, and did my suggestions work? That's an important piece too. Like, you have to know that you're actually solving the problem.

And after you've gotten to the point where you can reliably solve a problem, then you can either sell your time solving the problem. And so, for someone starting out, it's — I don't want to say that you should just go into dating coaching, because that's not necessary going to be someone's strength from the get-go.

But if there is something that you've helped people with dozens of times, then you're probably on the right track toward being able to monetize that.

Eleni: Thanks so much, Steve.

Steve: Thank you. This has been wonderful.

Eleni: This has been "How'd You Get THAT Job?!," a part of the Understood Podcast Network. You can listen and subscribe to "How'd You Get THAT Job?!" on Apple, Spotify, or wherever you get your podcasts. And if you like what you heard today, tell someone about it. "How'd You Get THAT Job?!" is for you. So we want to make sure you're getting what you need. Go to to share your thoughts and to find resources from every episode. That's the letter U, as in Understood, dot O R G, slash that job.

Do you have a learning difference and a job you're passionate about? Email us a If you'd like to tell us how you got THAT job, we'd love to hear from you. As a nonprofit and social impact organization, Understood relies on the help of listeners like you to create podcasts like this one, to reach and support more people in more places. We have an ambitious mission to shape the world for difference, and we welcome you to join us in achieving our goals. Learn more at "How'd You Get THAT Job?!" is produced by Andrew Lee and Justin D. Wright, who also wrote our theme song. Laura Key is our editorial director at Understood. Scott Cocchiere is our creative director. Seth Melnick and Briana Berry are our production directors. Thanks again for listening.


  • Eleni Matheou

    leads user research for Understood. She helps Understood to center its work on the lived experiences and voices of people who learn and think differently.

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