How To Connect With People You Don't Know

Episode 13

As a founder, making connections is one of the most important parts of starting and growing your business. It’s the way you find customers, partners, and employees. Over time, those connections will grow into friends, mentors, and trusted advisors. In this episode, we wanted to talk about, how do you connect with people you don’t know, and get them to start a conversation with you around your business?

Thanks for listening to this episode of The Stretch Goals Podcast! We'd love to hear your thoughts on this episode and answer any questions.

Find us on Twitter @The_Scott_Davis or @RobDickersonJr


Robert: In this episode, Scott and I will be talking about how to connect with people you don’t know. This is the Stretch Goals Podcast, where each week we’ll share insights and lessons learned based on our experiences as entrepreneurs. We’ll challenge you to create ambitious goals as you start and grow your business. I’m your host, Robert Dickerson.

Scott: And I’m Scott Davis.

Robert: As a founder, making connections is one of the most important parts of starting and growing your business. It’s the way you find customers, partners, and employees. Over time, those connections will grow into friends, mentors, and trusted advisors. In this episode, I wanted to talk about, “How do you connect with people you don’t know, and get them to start a conversation with you around your business?”

Scott, this is an area that I’ve been working on a lot lately, growing Mapout. It’s just really connecting with people that I don’t know in different industries, both to find customers and also employees. I thought it would be really good as we start the new year to talk about this, and talk about some outreach methods that we’ve used to get in touch with people, how we find these people, and how we connect with them.

Scott: Sure.

Robert: Let’s talk a little bit about how, first, you find people to connect with. I’ve been using LinkedIn a lot to find people, and also Twitter. People that have posted articles and things like that. How have you gone about connecting with people for MobX or some of your other businesses?

Scott: Well, I’m not a big LinkedIn guy. I mean, there was a time when I was, but I just don’t see … I’ve gotten connections through LinkedIn and picked up projects and things like that, and it has its benefits, but for me it’s less beneficial to my style. I like to consume information, and I find Twitter to be more engaging for me personally. I have no problem commenting on someone’s article, saying, “Hey, man. This is cool. How did you do it?” I tend to get a better response on Twitter than I do on LinkedIn. LinkedIn, in my perspective, is more, “Hey, I’m connected with these people. Want to have lunch sometime?” Whereas Twitter is more conversational for me.

I’ve definitely made some good connections on Twitter over the years, but when all else fails, look around you. There’s people everywhere to talk to. You know, airports, coffee shops, whatever. I meet a lot of interesting people. I met someone last week in my accountant’s office, we were just talking. The funny thing is, when this guy came in and sat down, he was like, “Hey, how are you? Happy holidays.” I’m like, “Oh, gosh.” I’m like, “Man, don’t talk to me, dude.” I’m like, “I’m on my phone. Leave me alone.” But no, it ended up turning into me picking up a new customer, so he probably knows who he is now. He’s listening to the podcast.

Every medium out there is made for connecting with people. I don’t really use Facebook for business purposes, but use every method that you have out there. I mean, what are you doing?

Robert: Well, a lot of times I use LinkedIn to find people’s interests and just kind of gauge what they’re working on, so I have something to start a conversation around. Then I’ll go to their Twitter profile and look at, you know, “What articles have they posted?” Kind of what they’re interested in. Because I find if you approach people with questions about what they’re working on, try to establish that relationship first instead of just going right into trying to sell them, right? I mean, to me, that’s never worked very well. Then I try to start a conversation, or grab lunch, or grab coffee. That’s the way that I’ve found to meet a lot of people, and just have conversations about things that they’re working on, things that I’m working on. See if there’s some synergy there that we can work together.

A lot of people I’ve found are open to having those conversations. You just have to approach them in the right way.

Scott: Yeah, and it’s not one of those things that … You may not get an immediate, you know, business opportunity or whatever from it, but the seed is planted, and eventually they’re going to come back, “Who’s that guy I had lunch with that one time?” They’re going to remember. Then that opportunity opens up for you. That’s happened to me many, many times. One thing that’s a little bit different than what you and I just talked about, which is where we’re going out and, like, seeking people and trying to get to know them, there’s an app called Charlie App., and basically if you’ve got a calendar meeting with somebody, it goes out and looks them up on social media, LinkedIn, Twitter, Facebook, whatever, finds their posts on Medium, blah blah blah blah blah, and it gives you a summary before your meeting of who they are, what they’re interested in, what their last five Tweets were, all that good stuff.

You kind of have this quick Cliff notes version of who the person is, so if you’re somebody like me who doesn’t have time to remember anything, you can just quickly reference who they are and what they’re doing and what’s important to them, and sometimes it’s not accurate. For example, Rob, you are obviously a white male, and sometimes it tells me that you are a black gentleman in North Dakota, and that’s fine. I know that’s not you. But for the most part, it’s picking up, you know, who the people are, what’s important to them. If you’re not comfortable, you go, “Rob, I see here that you’re interested in Java development.” You know, you get the idea. It’s a cool app.

Robert: That’s pretty cool. I think one area you talked about, too, was these are relationships you’re building with people, so it’s a long-term game. It’s not a short-term game where you’re going to get something out of it immediately. I mean, you’re trying to build a relationship with someone that’s mutually beneficial for both of you. I think you have to look at it from that perspective, too, is that, “What do you bring to the table for them? How can you help them with some of the things that they’re working on?” Whether it’s through promotion or whatnot, or bringing more business for them. When you kind of connect that way and think about it that way, I think you have a better chance of success.

Scott: Well, and you know, most people know when you’re just trying to talk with them to make a sale, so don’t do that. Make relationships, sure. Probably seven out of 10 times I go out to have lunch with somebody, it doesn’t turn into anything, but those three do, and at least 50% of the time, I at least keep those people in my circle of friends. On a coin flip, the person I’m talking to, I’m going to talk to again at some point. That’s really, it’s about building your network. Those people then become someone you can send an email to, “Hey, will you help me beta test this?” Or, “Hey, would you give me a like on Product Hunt?” All those things. It all works out. Just meet people. Don’t be afraid to meet people.

Robert: I think it’s also good to follow up with people as well, and keep those relationships going. It’s really up to you to continue to do that, because everyone’s so busy doing their own thing that it’s important that you continually follow up with people, and keep having coffee, or keep sharing information with those people, because it takes time, like you said, to develop that relationship. You need to keep following up.

The other thing I wanted to talk about, too, is that a lot of times you might send an email, you might Tweet at the person, and they ignore you. I think you need to not take that personally and continue to reach out to people, because I know with me, I get so many emails in the day and there’s things that I want to respond to, but you know, I mark them to come back, and then I never come back. You can’t take things personally. People are just busy. You need to keep reaching out, and I think normally if there’s a relationship there and the person is interested, they’ll respond eventually.

Scott: Change your approach, too. Don’t send the same email every time, you know? That’s fake and, you know, people see right through that. You know, usually what I’ll do, I like to get to know people on a personal level, like I like to, “Hey, man. You want to go play golf?” “Do you like to go to the baseball game?” Things like that. I like to learn what makes them tick, because I’m interested in that. Then, I use it as an icebreaker to bring back open conversations. I’ll say, “Hey, man. Did you see the game last night? Yeah, cool. Blah blah blah blah blah. By the way, you want to get lunch next week?” Or something like that. If you give them a reason to engage in the conversation, they’re going to open that email and reply, especially if it’s just a quick, “Yeah, I saw the game. That’s awesome, man.” Those types of things. It just opens the conversation back up, and it’s the same thing when you’re in person. If you’re at a social event downtown for social networking and you see somebody just you don’t want to put in an awkward position, be like, “Hey, man. Nice suit.” Whatever. All of those cheesy little things, they work. It’s all about connecting.

I read this … Well, I didn’t read the book, if I’m being honest. There’s a book called How to Make People Like You in 90 Seconds or Less. Obviously everyone likes me, so I didn’t really need to read the book. I use this app called Blinkist, which summarizes books for you, basically like Cliff Notes, but a little bit more detailed. I scanned through the book using Blinkist, and there’s a lot of things in here, and good tips, but one of them is, like, when you meet somebody for the first time, it says, “Look directly into their eyes and establish trust. Once you’ve made eye contact, be sure you’re the first one to smile.” That’s an example of making a good first impression. People remember that about you. “Rob is happy. Scott is crabby and grouchy. Who am I going to go to? I’m going to talk to Rob.”

Lots of little things, you know. There’s lots of books out there on how to connect with people, but some of us are better, you know, maybe more charismatic than others, so it’s a little bit easier, but just don’t be afraid to talk to people.

Robert: Yeah. I think you have to get over your fear. I mean, I’m an introvert. It’s harder for me to go … Especially at large events, to go up to people and just start making conversation. I think you just have to get over that and just reach out to people. The more you do it, the better you’ll get at it. Just treat it like you would a friend. You know, you go talking to a friend. Don’t treat it like a … If you’re looking for customers, don’t treat it like a sales call.

Another point I wanted to make, too, is don’t make assumptions about people that you meet. I know I was at a conference a couple of months ago, and I always like to talk to the speakers at the conference, and so I was trying to go talk to this one speaker, and I ended up meeting one of his colleagues and started talking to him. Now we have a very good relationship because we both work in kind of the same field. The speaker wasn’t a person that really was a good fit for my business, but this other person that I met was, so I think it’s important that you don’t make assumptions about people, and that you just try to connect with everyone, because you never know if they’ll know someone else that they can refer you to. I mean, things like that happen to me all the time, where they’ll say, “Oh, you’re doing that? Well, you should talk to this person over here.” They can help you make those connections.

Scott: Yeah. I mean, being connected is extremely powerful. Let’s take a step back for a sec. There’s science that suggests that connecting with other people makes you live longer, makes you happier. There’s a root inside of us from an evolutionary perspective that makes us want to connect with people. There’s that, but what we care about is obviously, you know, opening up doors and having new conversations and potential new customers. You only get that if you go out and talk to people, and like you said, you’re targeting maybe to talk to one person, but tangentially you end up connecting with somebody else. Maybe five other people, but the point is, having connections is powerful. Not from a, “Rule the world, take it over” kind of thing, but just you’re downtown and you see somebody you know, and it turns into an opportunity, whether that’s to have beer, or dinner, or a new project. It’s all very beneficial.

Robert: I think looking outside of your network is one area that I’m working on right now, is that, you know, I have a lot of people in my network that have a strong technical background, just because of the projects I’ve worked on, the companies I’ve worked on. Really, a lot of times those people always bring, I guess, similar viewpoints. I’ve been networking a lot with people in sales, people in marketing, and it’s been so interesting to me to see the different viewpoints they take on starting a business, on the things that they value.

It was funny, I was at a sales conference, and they were saying, “Oh, the salespeople are the most important people in the company.” If I go to a technical conference, they’ll be saying, “The technical people are the most important people in the company.” That part really cracks me up, but it’s just a different mindset. A different way people think about growing their business, and so you kind of bring all those different viewpoints into your own and figure out how you can best grow your business, how you can start your business out.

Scott: It goes back to one of our previous podcasts about growing your team. You know, you want to have people that are different than you. If everybody’s like you, you don’t learn anything. You know, you want to be able to connect with people that have different experience, different information to share, different connections, and every connection you make, you’re opening up the door exponentially to connect with somebody else.

Robert: Yeah, and you’re trying to find, especially when you’re talking about employees, you’re trying to find people that are really good at specific things that maybe complement your skillsets, or do things better at certain skills that you don’t have. When you’re reaching out to people, maybe not only customers but also people you want to hire or get involved in your business, it’s important to kind of look outside your network and look at things that people have worked on, and what their experiences can bring to help you grow your business.

Scott: Right. You said you’re an introvert, and I am too, to an extent. I just talk a lot. I remember, Rob, when we were in high school, my first day sophomore year was my first day at our high school. I didn’t know anybody, but I found one guy, Daniel Dixon, who was in one of my classes, and I said, “Hey, I don’t know you but you were in my last class. Can I sit down at the lunch table with you?” I didn’t want to do that, but I didn’t know where else I was going to sit. I took a risk, and that lunch table ended up being the lunch table that you sat at, and half of my other friends I still talk to today sat at. If I hadn’t done that, who knows which table I would have been at? Probably, like

Robert: Probably sitting by yourself.

Scott: Probably. Yeah. That’s very high up in probability. Either that or the cheerleader table. My point is, I didn’t have a choice. I’m not somebody who goes up and talks to somebody I don’t know, but in this case, I was kind of like, “Well, this guy is relatively harmless looking. He looks like he doesn’t have any friends.” Sorry, Daniel. “Let me go and talk to him,” and whatever. Dan is now much larger than both of us. He’s like six foot six and a state trooper, so I say that, he was much smaller in high school. My point is, you know, just you’ve got to be comfortable getting out of your own comfort zone. You just have to take those risks sometimes.

Robert: Yeah, man, especially at conferences and things like that, I think it’s good to step out of your comfort zone and just reach out to people. That’s how you’re going to make those connections. Don’t be afraid to send those emails and connect people through social media. They might not respond, but keep trying, and if they don’t then just move on to the next person, because at least you tried, you reached out, and eventually maybe that connection might come around. You might meet them in a different way, and they’ll remember that you emailed them or that you reached out to them.

Scott: It’s not all about business. I mean, yesterday I went to the eye doctor for the first time in my entire life, and you just strike up conversations with people, and hopefully I made that guy’s day better, or vice versa. Just getting to know people is fun. I enjoy it. Trust me, I don’t want to talk to people. I’d be in a black room with no lights on for months at a time and be totally happy, but you know, it’s nice to connect with people.

Robert: I think the feeling of rejection really, for me at least, that’s one thing that’s harder for me, and scary, is that feeling of rejection, that people aren’t going to accept what you’re working on, or they think what you’re doing is dumb or stupid or whatever. You just got to get over that, I think. That’s one area that I’m working on, is just pushing through that and not worrying about it.

Scott: Well you’re married and have kids, so clearly you’ve pushed through that at least once before in your life.

Robert: Exactly. Well, I convinced her, right?

Scott: That’s right, yeah. Well, I mean, I met my wife … The first time I met her was at a trade show in baseball, and I actually didn’t like her. I thought she was not a particularly nice person. She felt the same about me, but then three months later, we met again at another conference, and I was like, “That girl looks familiar to me.” I’m just like, “Oh, it was the girl who was across the aisle from me at the last conference.” I said, “Oh, yeah.” I looked over and she was sitting at a table with older men, people that she worked with, and I felt bad for her. I legitimately wasn’t hitting on her. I went up and say, “Hey, here’s my card. A bunch of us are going out tonight if you’d like to come out and enjoy life.” It worked out well for me, and that’s something I don’t do very often, but it worked out.

Robert: That’s pretty funny. Yeah. My wife, I went up to at a party and just struck up a conversation.

Scott: “Hey, baby.”

Robert: No, it didn’t go like that.

Scott: It was much smoother.

Robert: Let’s talk a little bit about employees, as you’re trying to grow your business. How have you been finding employees and making those connections?

Scott: I like to go with people that I know, you know, or I can relate to on a personal level. Somebody I see something in, like personally. If you’re a jerk, I don’t let you on my team. Like a guy I just hired on the first of the year is a guy I worked with at a previous company who I see potential in, and he wasn’t being utilized in a way that I thought was good. I kind of spoke to him, and it seemed like it resonated with him. He knew that he wasn’t really being challenged either, so I see it as an opportunity to give him that, you know, potential. Hopefully he sees that in himself, and at the same time hopefully he helps me grow my business. Employees are hard. Don’t hire people because they could be your friend, though. That’s dangerous territory.

Robert: Yeah, that’s important to establish that, those boundaries. I mean, you want to have that connection with them, but yeah, I think that’s important, is that you don’t just judge employees on whether they’d be your friend or not. A lot of times, actually, I don’t hire intentionally friends into my business, because I want to keep those relationships separate. I’ve found that there’s so much going on in a business, and it’s not necessarily all the time a friendly relationship. It’s that business relationship.

Scott: It’s business.

Robert: If you try to cross those, it’s hard to separate those boundaries when, you know, if you work together and then now you’re grabbing a beer together, you’ve got to separate that, right? It’s hard.

Scott: Some people can’t. Like, they feel like they still have to bring work to the table while you’re having that beer. You know, you’re like, “Dude. Shut up. I’m here to, like, disconnect. Drop it.” Like that time that I was at lunch and wouldn’t stop talking about programming.

Robert: Yeah. Sometimes you just need downtime, and I really don’t like to lose friends over business, so that’s one reason that I try to separate that.

Scott: Yeah. That’s probably a podcast episode, right there.

Robert: What about people that are what I would call internet famous? These people that really have strong social followings, they might blog a lot, they might talk a lot. How do you connect to those people when they’re probably getting inundated with requests for friends or people who are reaching out to them? Say you want to talk to them at a conference or whatever. Have you been able to connect with those kind of people, and what have you found works well?

Scott: I have, actually. There was a guy called the Batting Stance Guy. He got famous years ago for doing those, like, two minute videos where he’d impersonate every Major League batter with a wiffle ball bat. He had their stances down. He was internet famous five, six years ago, before having 100 million views was common. I met him, I talked to him. They have big egos. The problem is that they connect with so many people that none of their relationships that they make on a regular basis are meaningful, so you can’t expect that. I read an article recently called “Confessions of an Instagram Influencer” on Bloomberg. He basically talked about how anybody can become one of his influencers, you know? You just have to have a modest budget to put towards it, a couple hundred dollars a month and you can gain traction and followers through automated services and things like that. A lot of these people, they may have millions of followers, but I’m willing to bet that less than a thousand of them are people that they really know and connect with. If you want to connect with them, you have to be willing to accept that you’re a small fish in a really large pond. That doesn’t mean that you can’t make connections with those people. You just have to talk to them about what’s important to them, not what’s important to you.

What I’ve found, you know, my sister, she works in the music industry. She knows a lot of great, famous musicians. When I talk to them, I talk to them just like I’m talking to you. It’s not, “Hey, man. Let me get your autograph. Oh, I love your song.” It’s, “Hey, man. What’s going on?” You know, you just talk to them like a human. When you do that, they connect with you. If you’re connecting with them in the same way that everybody else is, you’re just a flash in the pan. They’re not going to remember you. Make yourself original. Be authentic and genuine, and strike up a conversation about something that’s important to them, not just you, and you’ve got a better shot at making that a meaningful connection going forward.

Robert: I think it’s hard with people that have a large following, because you might only get a small amount of time with them, and then it’s gone, right? Maybe don’t expect a whole lot out of that relationship, at least to start. I mean, it has to be, with anyone, you have to consistently engage with people over time to build that relationship, and so one meeting is not going to get you some new business or get this person to do something for you.

Scott: It’s very rare.

Robert: You have to think about, “How do I cultivate this relationship?” One of the things you mentioned, how do you approach them with things that are important to them? You really need to think about that, because if you do that, if you provide value to them, then they’re more likely to reciprocate that back to you, whether you need a shout out or whatever.

Scott: Sure. Sorry. One thing that I’ve read in the past from successful social media personalities, people who built themselves, not with automated tools, is they say, “Engage with people.” Like posts, retweet them, respond to them. Ask questions. All of those things, they make an impact, because it shows that you’re interested in what’s going on. That makes it an authentic relationship, versus just this crafted thing for social media.

Robert: Yeah. A lot of times, that can get you recognized by that person as well, if you like their posts, if you start retweeting things, if you start sharing what they’ve written, that can be a good warm introduction to then reaching out to them, because they’ll kind of like see that you’ve been promoting their posts over time, so then they’re more willing to kind of engage with you that way.

Scott: Yeah. We’re in a day and time where people are using automated services to thank you for retweeting something, but you can turn that around by liking it and replying directly to it, and then it like pops up on their radar. Like, “Oh, hey, this guy actually is not a bot.” Make yourself different than everybody else. Do something different. Make yourself stand out.

Robert: That’s the hardest thing for me with Twitter, is there’s just so much … People are just posting the same things, and Edgar, and there’s so many bots re-following people. It’s crazy. It’s like, “Are there any humans on this platform?”

Scott: Yeah. That’s a very legitimate statement. There are people in there. Like I said, I pick up a lot of business on Twitter, and make a lot of new friends. I got an invite to Product Hunt through someone on Twitter years ago, and I share things. I get a beta invite to a new app, I’ll be like, “Hey, who wants this?” People are out there who are real, who listen, and they want it. Those are valuable relationships to me.

Robert: Let’s wrap up this episode. I think we talked about a bunch of different ways that you can connect with people you don’t know, and really it’s about, as with anything in life, it’s about creating that relationship with people, and how do you mutually benefit each other, and how can you bring value to the person you’re trying to connect with and get them to listen to you? Don’t make it a sales email or something like that, you know, try to build that relationship around things that you’re both interested in. Whether that’s for customers, employees, I think it’s good to reach out to people and really start building those connections, because it will help you grow your business, and it will turn into friends, and mentors, and advisors and stuff over time.

Scott: Yeah. Don’t be afraid to connect with people. If you’re worried about what people think about you, just forget about it for once and give it a try. You’ll find out that nine times out of 10, you’re going to make new connections. Practice with us. Comment on our podcast episodes, retweet us, respond to us on Twitter. We’re real people, too. We want to connect with you. We said that, so drop us a line. Let us know. Practice with us. We’ll give you some feedback. Share it with your friends, and give us a like on iTunes as well.

Robert: Until next week, peace.

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Each week we'll share insights and lessons learned to help you create ambitious goals for your business.

Robert Dickerson


Robert Dickerson is the Founder and CEO of Mapout a mobile learning platform that uses video courses to educate customers and train employees. He helps companies develop and launch their products.

Scott Davis


Scott Davis is the Founder and CEO of MobX, a mobile development software agency. He has 20 years of experience developing software for Government, Finance, Sports and the Telecommunications industry.