Dan Waldschmidt

by Dan Waldschmidt

July 28, 2018


VP of sales for Vision-e and owner of OTB, Jonathan Hairgrove, is Dan and Broc’s guest today on the podcast. While it’s nice to help take care of someone else’s problem with your software, it’s also okay to charge for doing so.

Sometimes our struggle is not staying motivated or being the best in our field, sometimes the struggle is to have a balance between our “side hustle”, our day job, and our family. Set realistic goals.

Jonathan also presents the idea of choosing one bill a month even though it may be small and determining to pay it with money from the business you are starting. 

Don’t miss the exclusive, one-time-only webinar on “How to Be Insanely Productive Without Working an Insane Number of Hours” on August 2nd @ 11 AM ET.


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Dan: [00:00:00] Hey guys, it’s Dan and Broc. Hey Broc. 

Broc: [00:00:04] Hey, to be with you. I’m doing great. 

[00:00:07] It’s Dan Waldschmidt and of course Broc Edwards. This is Bring Your Own Awesome. I’m two for two so far, Broc. 

Broc: [00:00:14] Good job! You get the name right. 

Dan: [00:00:17] For a while, I kept saying bring your awesome and then Brock each time go, “Dude, it’s actually Bring Your Own Awesome”, we’ve done that well. Today with us, we’ve got to add another awesome person to share with you. His name is Jonathan Hairgrove. He’s in the empire. He’s doing some incredible stuff. In fact, he joined us in Hollywood for the most recent awesome palooza which is great because he lives like five miles down the road from me or like maybe 10 or 20. It’s close, but we all flew like 7,000 miles and all of this is only the slightest bit of an exaggeration to all meet up in Hollywood. Jonathan, tell me about that. Why the heck did you go all the way to Hollywood for Awesomepalloza? 

[00:01:03] It’s kind of funny actually, you were doing the book giveaway and I actually don’t have a copy of this. So I signed up for the Book Giveaway online and then some of them popped up as radical reboot and I was like, “Oh, that looks valuable”, so I bought the course started going through it and then I really want that, that led to us talking a lot more. You invited me out and I was like, ” You know what, there’s nothing like flying across the country to meet someone who you live in the same city with. So it seems it seem viable”. 

Dan: [00:01:32] That’s awesome. Look, I’m cheating a little bit because we are in the same city. Why don’t you tell Broc and the rest of our community, actually, you met Broc in Awesomepalooza as well but why don’t you tell the rest of our community a little about who you are, what you’re doing and we’ll start there. 

Jonathan: [00:01:56] I live in Greer, actually, it’s the same city. Greer, South Carolina down here and I’m V.P. of sales for Visiony which is a software company as well as Gabie which is a new company, I get into that later. I also have a side hustle with a buddy called OTB. We actually call OTB zone and we never truly named it, could stand for Outside The Box, Over The Bridge, any OTB phrase you really want. We were a little lazy when it came to that. So that’s the fun site hussle. We’re focused on solving problems through solutions and we focus on software on that, it’s more top to bottom and then my day to day sales. 

Broc: [00:02:37] Let me jump in there, Jonathan. What kind of problems you focus on solving? 

Jonathan: [00:02:45] On the side hustle or all of the above? 

Broc: [00:02:47] Let’s get start with the side hustle. 

Jonathan: [00:02:49] It kind of started out where we started it together because people were coming to us because we were kind of people who don’t have the nephew or the grandson to help them do whatever that they need and then we dug into the problem instead of just like, “Hey, we helped me set up my social media or a web site”. Not our favorite but of course we know how to do it in 18 minutes. So we did it and then we found a couple other areas but we also focused on scratching our own itch. A good example is, my buddy’s a big disc golfer and so he wanted to create a solution to make it a lot easier to run the different events that they have going on all the time where there’s pay outs of rewards and in all this different algorithm that goes into it. That’s kind of one project we’re working on that we could then obviously share with others but it’s a pet project right now. 

Broc: [00:03:39] What’s your big goal with the side hustle? Where would you like to see it at the end of the year? 

[00:03:44] Great question, in the last, probably, since Awesomepalooza. This was a little bit of a jolt, at Awesomepalooza it became more aware that we were limited in our bandwidth. We could take on amazing projects but were limited because it’s a side hustle right now. So being really careful and then looking at out of Awesomepalooza came looking at subscription model. Instead of just building software and saying, “Here we go. It’s amazing, will maintain it for X peanuts a month”. Looking At a building a solution or a subscription type service of giving the additional value. I’m actually working on something around my day today which has to do with sass and software sales and in trying to build kind of a course for people who maybe went to college, should have gone to college or didn’t go to college and are just kind of in dead end jobs and are searching. Is there something better that a connection make a living at? I’m kind of tossed around an idea to build a course around that. To answer your long question with a long answer. End of year for OTB, I Would say, I really want to finish up two of our pet projects that we’re working on and I would really like to start or launch one large project that will impact the largest audience possible. That might be it. Go ahead, Dan. 

Dan: [00:05:11] I know somebody who’s got a large audience. 

Jonathan: [00:05:12] They might have an updated question a little bit. Potentially, work with — Dan and I have to have kind of very prelim talks since Awesomepalooza. Obviously, a lot of things that have come out was because I was there not only the things that I learned but the people I was able to make connections and just start a conversation where it leads could be anywhere or could be nowhere, right? But at least I’m having a conversation I wasn’t having before. 

Dan: [00:05:43] Yes, that’s awesome and you know what, it was amazing about that. I’m looking at the sheet of paper, Jonathan, that Brock and Kat had us go through, small steps to big results worksheet. It’s been on my desk and I’ve got one thing in career, one thing in finance, one thing in health and I can’t, I can’t. It’s really hard to explain to somebody who wasn’t an Awesomepalooza, that little workshop, “Oh, my gosh”, that little time was amazing. Talk to me in my commonsense terms about this side hustle because you just it just sprang out. I know you, you’re a hard charger. We’ve talked on the phone before just about sales and business growth. You’re busting your butt. You’re working a lot hours doing a lot of stuff, building relationships traveling for your, I call it day job. All of a sudden you’re doing two or three or five things on the side hustle, bouncing that got to seem like a challenge, almost an impossibility. 

Jonathan: [00:06:50] It does, yes. All of those thoughts rushing to my head every single day like, “What the hell are you doing?”, thank you for pointing that out. It made me by design, I have to figure out what we call sprints. So on our own pet projects and then when a project comes along that has, Hey, this means more for us. Let’s put the pet project to the side.” We don’t have hard deadlines for our pet projects, for better or for worse, right? I think for better when something comes along where it’s an opportunity we say, “Okay, we’re going to set this to the side and put our focus on this project.” It’s also tough because there are so many — and you mentioned this Dan, maybe the other day is like. You can talk to anybody and want to help them find value. Think that you can help them move forward whatever the case is, right? That’s the same with us when we have a conversation. Good example, we go to this little Italian place angrier that we love and we’ve been going there for six months. My buddy and I every day for lunch, nearly everyday and we’re like, “Be really cool if we could show the menu online to our friends. Do you have a Web site?”, he’s like, “No, I had a bad experience”, and we’re like, “I do. Can we just help you out maybe for some trade. We don’t want money. Just give us some free food”, and so we did that, right? like old guy, awesome food. We just want to help them out, more so for us so that we can place the order a little easier whatever the case is. We have these conversations and it comes out, in the end I have to figure, oftentimes, I cannot forget myself in there, is like, “How can I help? How Can I help?”, and I got advice from a mentor, he’s like, “It’s okay to be greedy for yourself once for a while”, and even though I’m working on that time it feels like I’m greedy for money or whatever the case may be but in reality I’m just so focused on it if I solve somebody else’s problem that it will, I will ultimately take care of myself without asking for money that never happens, right? I fall into those valleys where you have to prioritize as everybody always says but in reality like my pet project it’s really important to us because we know that there is an audience for it but at the same time when someone comes along as like, “Hey, we’re happy to pay you money to help us with this and you can solve it”, doing your great work then you’ve got to put that to the side and say, “Okay, let’s move forward here”. 

Broc: [00:09:17] When you look around people, a lot of people now want to side hustle or want to even try and figure out how to change their career, go in a different direction but sometimes we can’t just kick it off the launching pad. They think about it, they talk about it. They do a ton of research. Just from your observation, what gets in people’s way in? How could they get out of their own way? 

Jonathan: [00:09:40] It’s a great question. My dad, probably got me into side hustles way back when I was really little, like we kind of knew I was destined to be in sales. He was always looking for something else and we’ve gone through everything, like we’ve gone to looking at franchises, the MLM, the direct sales. We’ve gone through so much and you reach a point where you’re I’m like, “I’m either burning bridges or not building relationships I want”, and then you move on to something else or you try to do something, you don’t learn it, you don’t have the bandwidth to learn everything you need to know to take on this new business you’ve never heard anything about. fly probably falls by the wayside. I’ve Been trying to solve this and answer this for myself. I stayed where I knew best, right? I’m in software, I stayed in that lane. A lot of people don’t do that, right? So they’re engineers by day and then they’ll go an amazing cover band by night or something very different. For me, I stayed in software because I have a broad swath of experience there. Software made sense but it also gave me the opportunity to really expand on what I wanted to do. I sell software but I don’t get to be the implementer of it and solve from the ground up. It’s kind of, “Hey, we’ve found this problem, we solved it, go sell it.” I wanted them to do the entire encompass of that but the advice side is tricky because — that’s why I sit down with people, “Hey, I’m working on this, trying to solve this problem”, or “I want to do this. I Want more money or whatever the case is”. You really got to sit down with someone and have that conversation. You can’t just say, “I’m going to do this and it’s going to be successful. You need to sit down and dig deep like you’ve got to get very frank and honest with yourself if you want to be successful. 

Dan, Broc: [00:11:41] Yes. So. 

Dan: [00:11:41] Sorry brock, go ahead. 

Broc: [00:11:44] You kind of building on that, being an entrepreneur or having a side hustle, there’s a lot of glitz and shininess put on that these days but what kind of the living the dream downside as you’re doing it because you’ve got kids, you’ve got dogs, you’ve got a life, you’ve got two jobs on top of it. What’s the greedy downside or what makes you wake up and go, “Oh man, I got this again”? 

Jonathan: [00:12:12] For me, I’ve rarely lived a life where I wake up and I’m like, “Oh man, I got to go to this job”, and if I ever felt that way, I was confident enough in myself to go find something where, if I wake up every day like it, I’m super lucky. I wake up every day and I come to VP sales job and it’s a small company so I do impact things. I kind of build my own team and have a lot of sway here and I have that strive to always better myself. I’m good at that and working to get better and etc. I wake up with that desire. The struggle on the side hustle side is when I go home, I’ve got my wife and the boys were trying to adopt and all the shit that goes with that and then family comes into town, my family that lives here. So there’s all this other stuff. My wife is like, “Can you be around a little more?” It’s a juggle of, “Okay, once the boys and she goes to bed”, then take two, three hours before you go to bed and work on that or the weekends. The glitz and glamour for me is not there. It’s not like I had pressed a button and magically making all this money. I’m working hard to just build a very small residual income for myself and it’s not easy. People would probably say I’m an idiot to keep doing this but it’s something I’m good at and I love. 

Dan: [00:13:45] I hear you say in nice way, “I’m trying to get the side hustle off the ground but not really making a lot of money a little bit right now. Look, I’ve got three kids, two dogs, two bunnies, one cat right, a wife who’s out running and having Crepes with her friends right now”, and you’re bouncing those out. I mean, talk to me about the home situation. Does your wife like, “Hey, go pursue your dream”, or is it like, “Look dude,we got to work on this. This is causing relationship issues, this is causing challenges. I think a lot of people in the group tell me I want to do this but my wife has a problem with me working this much. ” Is that a problem for you? 

Jonathan: [00:14:33] Yes, it used to be. I did a startup when I moved to Greenville about five, six years ago and it literally was 24/7. That was probably the biggest strain on a relationship. The fact of how it ended, she’s like, “I kind of told you”, and so I should have listened to her because it ended poorly like how most startups do as far as exit itself. I should’ve listened to her but at the same time she was supportive. We just had to work through some of the top layer stuff. It wasn’t like, “Hey, it’s me or”, she would never do that. She understands why I do what I do. Before when it was just me, before her and I got together, when it just me, it was like, “I want money”, because that’s the only thing I really had, was did to chase that. Then when her and I came together I was like, “All right I want money”, because I want to do X Y Z take her here, do this, so I still have a little bit more. When we got the boys now it’s like, “Oh jeez, okay, I want this, I want them to –“, they’re coming out of a rough foster care situation of rough situation with the family and so we’re trying to adopt them and so I want to create and experience for them where they experience life to the fullest and in order to do that I have to work my ass off in both my day job and my side hustle. She’s always been supportive and yes there’s been strains and I’m not going to sugarcoat it at all and she’d be the first one to tell you but she’s been extremely supportive and now she reminds me, “Hey, dumb shit stop doing this”, it’s, “Hey, don’t forget”, she knows how my brain works, thankfully. After almost seven years of marriage she knows how my brain works and says, “Hey, I put it on your calendar. I put on your work calendar so now you have to be here for this thing.”. 

Dan: [00:16:23] It’s a smart move. 

Jonathan: [00:16:25] She gets me. 

Broc: [00:16:26] We’ve been talking a lot about this and that there is the greedy reality and then there’s the big dream. What is like the one thing you would recommend people to just do if they wanted a side hustle? What’s the one thing they can do to get started? 

Jonathan: [00:16:43] For me, it was set realistic goals. I’ve never been thought of it as a short dreamer or somebody that doesn’t have huge lofty goals but at the same time, when I don’t obtain those then I get pissed off and all this. So I came into the realization of, “All right, I set realistic goals. If I want to get to point A to get to point B to get to this amazing place that I see for myself”. 

Dan: [00:17:16] What is realistic? Coz I think it’s different for each of us. 

Jonathan: [00:17:19] Absolutely, it literally might be taking one bill and saying, “I want to pay that bill through side hustle money”. Legitimately, I’ve done this before for myself, when I want a side hustle it might not be starting up a full on business. It might be, go in garage selling, getting products and resell which I’ve done 99% of my life. I’ve gone found something or I see something, like my uncle’s basement, I was like, “Hey, are you suing that? I could probably get some money for that because if you want to sell will split 50/50”, and I say, “I’ll give you 20 bucks for yours”, “Okay” and I went sold it for like sixty-five bucks. So that can be something that’s a side hustle too. Side hustle doesn’t have to be on, starting an LLC and I’ve got to go get an office space, that’s not side hustle. Side Hustle is wherever you want to provide whatever you need or whatever you you want down the path for yourself, like find one bill, can be frikken Netflix and say, “I’m going to pay Netflix every damn month with side hustle money. I’m not going to touch what I bring in from my day job”, and then pay another bill. 

Broc: [00:18:26] That’s awesome. 

Dan: [00:18:26] That is incredible advice. You know what’s funny, Brock? I don’t think I’ve ever heard that advice on launching site also, have you? 

Broc: [00:18:33] No, not a bit but it makes total sense. I mean that breaks down to the real simple reality, like make nine bucks a month to cover Netflix. 

Dan: [00:18:42] Exactly. That’s incredible. For all of you listening, that might be the best advice I’ve ever heard for how long on side hustle. Take one bill, make a Netflix, Nine bucks, ten bucks, 11 bucks, whatever you’re paying at just every month that’s going to be your thing. Jonathan, how can the Empire help you with your side hustle taking it to that next level? 

Jonathan: [00:19:07] I’m bad at this aspect. Price should be better. 

Dan: [00:19:12] What’s one thing your’re looking for? Are you looking for people to hire you? Are you ooking for people to join with you, to help you develop direct code, relationships, referrals, prospects? 

Jonathan: [00:19:21] I think, the biggest thing that I would want, and I haven’t tested this so maybe they’re open to it already, is this new thing that I’m working on for a subscription type model to help those people because I went to college and dropped out this is where it’s coming from. I had to find my way but I have a different mentality than probably 90% of Americans or people in the world for that matter. What I want to do is help give them a leg up. I’ve had incredible experience myself. I want to take that experience and digest it into like a course where they can go get that experience and then use that as a leverage to get a job or whatever. 

Broc: [00:20:06] How can the Empire help you to fix that? 

Jonathan: [00:20:08] I think, if I were to put together something and say, “Hey, give, like a Google survey kind of thing. Give me your feedback”, and if they can give me the honest feedback both from their perspective but also like I said my target audience is 17 years old to 29 years old or give me in front of those kind of people and say, “Here’s how we can help”, on the software side, we’re kind of our bandwidth is limited on the projects but I fricken love, I get a high off of this, having conversations around helping people solve even if it’s not us solving it. I might say like the other day I told someone, “Hey, I’ve got a quote for $50,000 for this project”, and I was, “Dude, can you give me six months. Please don’t spend that money. I would charge you max $7,000 and I would get you an MVP faster than anybody else.” Sometimes, just that conversation can be helpful in two ways. 

Dan: [00:21:02] That’s incredible. That’s incredible. Thank you Jonathan. For all of you listening, I think you could agree that we could talk to Jonathan all day. Unfortunately, like all great podcasts we have to leave you hanging so that you’ll come back for the next one. Jonathan is in the community, he’s active. You can find he’s talking, he’s sharing, he’s adding notes, he’s part of Awesomepalooza. So go find him and talk with him as you can tell. If you’re in need of ideas or a tad bit of energy, right, Broc? A tad bit of energy. This is the — I’m sure you’re not a runner, Jonathan. You’ve got all this –. 

Jonathan: [00:21:42] I’ve got the running high without the runner –. 

Dan: [00:21:43] Maybe you bring it to the group. I don’t know. So for all of you listening to this, come back to another episode, as you know we’re doing some incredible stuff inside the Empire. We talk about Bringing Your Own Awesome. You heard how they do that today. Go take a pill, say, “I’m going to pay this with side hustle money.” Side hustle money could be going to a garage sale, grabbing a sign that’s $2 in a rusty, ticket home. Shining it up, cleaning it up, taking it eBay and selling it for $65 or $70. So there’s no excuse not to have a site also and it’s as easy as what Jonathan just shared. I imagine you have more to share with us about that Jonathan. 

Jonathan: [00:22:20] Yes, few more. 

Dan: [00:22:22] Fantastic. Thank you for joining us today. 

Jonathan: [00:22:25] Absolutely, thank you for having me. 

Theme music (“Runaway”) by Shadow of Whales: https://www.facebook.com/shadowofwhales

About the author

Dan Waldschmidt

Dan Waldschmidt doesn’t just talk about leveling up. He’s obsessed with it. He's set records as an ultra-runner and been the personal strategist for the leading business leaders of our time. He wrote a book, called EDGY Conversations that accidentally became a worldwide bestseller and continues to share his insights from the stage as a keynote speaker and on the blogs and podcasts you will find here. Most days, you'll find Dan heads-down, working on breakthrough strategies for his clients at EDGY Inc, a highly-focused, invite-only, business strategy execution company based out of Silicon Valley.