S6E20 - Chris Cicconi - Freelance Hustle: Navigating all the Ups and Downs
14 Apr 2025 · 39 min
Chris Cicconi talks about running a freelance consulting business, building a personal brand, and keeping multiple income streams going. He walks through the real challenges of client management and how to keep the work steady when you're on your own.
Chapters
All right, here we go.
Now I feel comfortable.
I need it.
Oh.
We're going to start the episode off today with some laughter, some brevity. What's up, everybody? My name is Scott Lease. I'm here with my friend and partner and co founder in the Surf and Sales Summit, Richard Harris. Thanks for tuning in to another episode of the Surf and sales podcast. What's going on, Richard? How you doing?
I'm good, man. I've talked to you more this week than I have in a long time. So I, I actually need to talk to you offline about some stuff too, about particularly going to Colorado, so. Yeah, but we'll do that. But I'm good, I'm good. You feeling better? I know you're, you're getting over your cold and your flu and your, These.
Things take a long time for me. You know, normal people lick a cold in three or four days and it's a couple week affair for me, as you know.
Yeah, yeah. Welcome to old age.
That's not making it any easier.
That's for sure.
That's for sure. We are going to be joined today by my friend Chris Ciccone, who is out in Montreal, Quebec, Canada. And this guy is a freelance extraordinaire. I don't even know really how to begin to explain all of his different job titles and all the different things that he does, but he's got sales experience, business development experience, creative experience, all this kind of stuff. Welcome to the show, Chris. We are glad to have you, man.
Right on. Thank you so much, Scott. Thanks, Richard. You know, Scott, the irony of that coming from you, that you can't explain the list, other folks, right. That it's a little bit humorous because I was looking at both your linkedins and I'm just scrolling for days and days, but, but I'm super excited to be here. So thank you so much for having me.
I, I tell Scott this all the time is like, I don't know what you actually do, Scott. So it, you know, he, he knows I say this to him as it's partially serious and partially true or partially joking. But, you know, at this point, I.
Think, Scott, I think you just steal, say it to steal business from me now. That's what I think. I don't know. Nobody knows what Scott does. You should probably just work with me. Yeah, yeah.
Right.
Well, tell everybody a little bit about your background, Chris, so they have some context and maybe a little bit about what you're working on at present.
Yeah, right on. So I, it's funny, I, I Always say I started my career as the prototypical accidental salesperson. Like, I studied kinesiology and I have a bachelor's degree in athletic therapy because I thought I would be running onto the field with these sports teams and doing all that glorious stuff. And then I realized Canada has like five professional sports teams and that was never going to happen. So stumbled my way into sales because I figured I can run my mouth and that's good enough to get a sales job. And just sort of made a habit of, of starting new things in sales. So I got an opportunity to start a brand new division at an established company, started, made a move into SaaS and was the first sales hire at an organization. Did a little beady stuff in between there as well, kind of building out new BD functions. I was like, you know what, this is really fun. I like the building, I like starting something new. But I keep changing jobs every year. So maybe instead of doing that I just do this freelance and fractionally instead.
Yeah.
And that's something I jumped into. It's been almost exactly a year and it's gone so well that I've been so busy that I haven't even had time to like name my company or anything. So if anybody out there has a really great name for a fractional sales and consulting company, please let me know because otherwise we're going with Chris Ciccone.
I. I actually think this is a, an interesting topic because one of the things that has always rubbed me the wrong way with people who go out on their own or they start any business is they end up focusing on things that don't really matter. Like, people will spend weeks trying to figure out their color pattern on their, you know, logo and their website and stuff like that, and they'll run through a hundred different names of their company. And I have a friend who's going out on their own right now in the marketing world and she's spending all this time on all this stuff and I'm just like, what are you doing? Why don't you just do the actual work and this other stuff will sort itself out and so you are sort of subscribing to that same ethos. Can, can you talk about is that.
Did I ever.
Conscious decision in your mind or where does that come from?
Scott, would you like to see my original marketing plan that had my color scheme and.
No, I don't. This is actually the, this is exactly the difference between Richard and I, because he'll worry about all those things and I didn't. I'm more like you. So how, how do you like decide that's what I'm just going to focus on this stuff.
Yeah. And first of all I heard marketing plan and I immediately became, began getting twitchy. So anything marketing related can we'll just leave that on the back burner. But yeah, it wasn't.
I'm the worst person to talk about some of this stuff or I feel like it sometimes because so much of it is not intentional. So I even starting my own thing, I, I had a really bad experience at the beginning of last year with a, a founder who decided not to pay me for an extended period of time, which was kind of the straw that broke the camel's back. So to say where I'm like, you know what if I'm not going to get paid I might as well just do it myself and not pay myself. Right. So that's what kind of set up this. Hey, I'm going to do my own thing. Got a few clients through referrals. You know, my network was, was really great to me. I started partnering with the folks at Unicorn as well as their head of sales development. So like I just kind of had business coming my way and so I started working on that. And even at that point, like I said, I didn't know the name. I didn't even know what my offering really was. Like, hey, I do sales stuff. I like early stage stuff, I like building stuff. I can help. And so a lot of what you're talking about, Scott, kind of makes sense. Whereas like, okay, I, I, I like doing this, I'm good at this. All of a sudden, hey, I, this is a marketable skill that I have. I can go start talking to people about that. And so much of it was just networking community related. I would start partnering with different vendors as well because you know, hey, when I get involved, early stage, I really like this, this and this tech stack. And all of a sudden they're going, well, you're going to implement some of our stuff. I know some people that could use your help and you could help us get in there. So started making partnerships like that. And honestly the leads kind of came rolling in for a period of time. So I just never took the time to figure out like what my colors are, what my name, the company name is. I bought the domain that is my name just so I could have an email address that was not@gmail.com, but my website, if you go there doesn't exist. It was actually funny. I, I just, I had a meeting with the prospect last week it's like, yeah, I'm trying to research you and I went to ChrisJacconi.com like your email says, and there's nothing there. Yeah, that's. That is accurate. There is nothing there.
It's all just come around. Right. And, and you know, things happen organically when you can kind of align what you want to do with what you enjoy doing with things that people want. And it's just sort of.
I'm fairly certain that I had done consulting for three years before I got a website.
That sounds about right.
Yeah.
And you still have a Gmail account?
I. Well, yeah, I have because I have so many different email addresses that I just said the hell with it. I'm just going to use Gmail for everything.
Yeah.
Which is, you know, a lot of people say that's the wrong move and that's going to hurt you or it doesn't look professional or whatever. I'm like, whatever, man. It's an email address. Like, I don't. Who cares?
It's not like@aol.com or something. Right. So, yeah, not that bad.
Yeah, yeah, that bad. Like that would be bad. I still laugh at people with that.
So that was the irony of me trying to name my company. Then it's like, well, do I name my company then? Do I need to buy another domain then do I need another email address? Like, fuck it, I'm just going to go with this. It works.
And these are the decisions that you actually don't need to spend that much time on because there's a million and one decisions that you're supposed to be making every single day. As somebody running their own business is hard. So how can I remove certain decisions from my plate? That was my thought process with it all. But you know, that's not, that's not for everybody. So I'm just. It's interesting to hear you echo some of my sentiment.
I, I always think back to actually one of my first sales leaders or actually my first sales leader and I, I always give Denia a big shout out because he kind of gave me that opportunity when I had no real experience and his thing in the sales world because it's very similar to, you know, know having your own kind of company is there are so many distractions and so many things that take you away from like revenue generating activities. So in sales as an ae, are you doing and spending your time doing revenue generating activities? And I find myself as like a founder and on the consulting side thinking the same thing where. Yeah. Is naming my company really Going to be a founder, a revenue generating activity is picking my color palette, is coming up with my marketing plan and all that. Like is, is it or is it not? And I think at a certain point it probably will be to be able to help in the scaling and things like that. But right now I'd rather be working with clients and getting new clients than, you know, filling out a word document.
Yeah, the branding part is interesting because if you name the company something, then all of a sudden you're working on Chris as a brand plus company name as a brand. Whereas for me, as I was trying to simplify decisions, I'm like, I already have a name that is somewhat of a brand. I'm just going to stick with that so people don't have to learn this new thing, you know?
Yeah, that's what I did. So although I just, I think I, I chose the wrong name. Like I, when I did it, you know, it was.
13 years ago and so I was trying to make myself bigger. So I chose the Harris Consulting Group, which is the worst email ever. But I did it specifically because I wanted to sound like a group, like I was a bigger entity. But I think, because I don't think the fractional approach was talked about in that way. Right. You know, as it has picked up that steam in the last two years. So I went down that path of that's why I chose that name. And even to this day people are like, well, is it you who does the trading? And I'm like, all right, so it certainly working for me in that regard and to the point of sticking with the name. So I, I agree with that. I don't think you need to over complicate it with, you know, sales simplified.com, you know, kind of a thing.
But I think that's so interesting because I agree that there was like a changeover in the last few years where not that long ago you did want to seem, hey, I'm, I'm bigger, I'm more official, I'm fancier. And that gives me more credibility, validation.
Yeah, yeah.
And I think that in the last couple of years, to Scott's point, there's been this big push as a brand, as an individual, I carry a lot of weight. So why would I hide that behind something else when I can just do my own thing and I can launch my own thing, I can call it, you know, Chris Chacone Inc. And that's good enough because people recognize the name as a brand. So I definitely think that flip has happened not that long ago that's really driven more of that individual piece. And to your point as well, Richard, then you don't have people asking you like, but, but are you the one doing the work? Like, is it you? Is it team?
I don't mind because of the name I chose. I don't mind them asking that. That totally. That I think has helped me, you know, like, I've had some very large enterprise clients and I think that that's what's helped, you know, even draw them in or my SEO approach. Scott.
You know, so he, he and I battle this SEO game all the time. So, so, so I have a question for you because this is the other challenge that I see with, with, with folks coming into their own space is, you know, the first year goes really, really well because it's a lot of networking inbound from the people they know, research. And then somewhere around that 12 to 18 month mark, it gets harder for them. Right. Because it's the kind of exhausted that list. Right. How are. Have you started to run into that yet? Are you. No, I'm making these other moves behind the scenes to help prevent that or is it like. No, I haven't, haven't run into it. And I don't, you know, based on my pipeline, I don't see that happening for the next two years, which by then all of a sudden now you have a name in the space. Right. Kind of a thing. A bigger name. Totally.
And I think that I am living some of that right now. And some of that is somewhat intentional as well, because to your point, year one, super. Well, year one went great. And I think I left year one realizing a couple things because in year one as well, like, hey, I'm. I've got my business. I just, you know, incorporated myself. I got my bank accounts. I want to, I want to fill those up. So, hey, you need me to do this? Yeah. You need me to wash toilets? Cool. You need me to do whatever it is. Like, I'm just taking that business on. And I'm probably not fully grasping what my worth is in the way of charging people. So I think in the first year, I took on too many clients for too little money. And I don't want to say burnt myself out because I, I want to respect that term as something that exists. But I think I overworked myself for too little money. And I think coming into year two, in the beginning of this year, something really important to me was, hey, can I focus on the things I enjoy doing I am good at and provide value and clients that I can charge a reasonable amount where it's worthwhile for me to work with them. So I'm definitely working with less clients right now. I'm definitely making a little bit less money right now. But I am happier with the amount of effort I am putting in and the return on investment I'm getting out of it.
Yeah, that's a good way to look at it.
Yeah.
Except now you got to get, you should be working with fewer clients but making more money. Right.
That's the next, that's the next level.
Right.
Well, you gotta add them back on and maybe.
I think that's the challenge. I think that's, I wonder if that's the challenge for people who move into that market. Scott, I don't know what you've seen from people that we know who've done this where they, they all of a sudden go, oh, I should charge more. And they do. But then they have fewer clients and they start to get into a little bit of a drought and that's when they're like, I need to go get a job now. Like, is that, is that what you. I, I've never thought about it or from that respect. But I don't know. Scott, have you, have you seen it? That's happening.
I've probably had that conversation three times in the last two weeks with people who've been running their own thing, and they've very quickly gone from.
Posting on LinkedIn about how they run a seven figure agency to now they're going back and working for somebody full time.
Yeah. So what do you think is the challenge? What, what advice do you give to Chris? Right. What advice? You know, having done this yourself, I've seen how you do it. I know how you did it. And now talking to others like, what's that advice for that? Getting over that hump of year one to year two?
You know, I think some people try. It's interesting because it's very similar to what SAS companies do. They try to hire their way into success or hire the way out of trouble, and they try to scale too fast. I, I know some of these people that I'm thinking about, I had conversations with in the last few days. They're running things on their own and then they hire people and all of a sudden they have an agency and a team of 10 and a bloated overhead and they're like, hey, we're doing $2 million a year.
And I'm like, well, hold on, not really.
You're doing $2 million a year, but you're spending 1.8 of it. And so you made 200 grand last year. Like, these are not the same thing. So I would be. My advice is always be really careful about how you grow. Be very mindful of your margin. That's one of, if not the most important things.
Learn more and more to lock in on your exact ideal customer profile and not take clients will be a bad fit or you won't be able to have some success.
For.
Don't try to execute too many different things in business. 5, 6, 7, and 8. When the first one is not really rocking and rolling yet. You know, the. These are. This is not, like, groundbreaking advice by any stretch of the imagination. It's just sort of like a reminder of sort of sound core principles that sometimes I think people get away from.
And. And I think you nailed it there when you compared it to, like, the founders in the SaaS space and. And other B2B spaces as well. Because I've seen very similar things with a lot of the founders that I do work with who are coming to me after year one and going, yeah, I hit a bit of a lull. But, like, you know, hey, I really know who my ICP is because I've got X amount of clients in year one. I was like, dude, your ICP is all of your friends who decided to help you out by buying this conversation. Right? Like, that is not your icp. And I think the biggest challenge I run into is getting in front of those founders and trying to have them understand that. Yeah, just because a bunch of people, you know, bought your stuff doesn't mean that is your proper target. That is your proper icp. Like, there's a lot of stepping back and figuring this out the right way you have to do. But I think to your point, Scott, a few of them just grab onto that and go like, hey, these 10 people bought for me. These are my perfect clients. I'm going to go scale this now. And they're just trying to get too far ahead. So it's. It's definitely a problem, I think, for a lot of different organizations. And the beauty of it, of running my own thing is, yeah, I don't. I don't need to be at $2 million after two years. So I can take a step back and scale it properly and go like, hey, I understand where I made my mistakes and I can slow down a bit and still be in okay shape. Where I think, to your point, Scott, when you're bloating your team and trying to scale something, that's not going to work You've got, you know, people's livelihoods in your hands. Like that's, that's a whole other level of burden.
You put a tremendous amount of pressure on yourself at that point in time.
And it's funny, and Scott knows this about me. I've watched so many people do this and hire people and I've contemplated hiring people and I've got, I've got like two people that you know are part time, you know, not my employees. But I never wanted to have employees for this reason. I never wanted to worry about health care and other than my own. I never wanted to have to deal with benefits and providing all that stuff and all that time and struggling to make sure that the money was coming in. Right. Like I, I built a lot. I have purposely stayed as a lifestyle business, right. And there's some things I could have done differently to, to grow it. But I have a question for you, right? So.
What are the tactics you use? Like you, you, you, you're. You're clearly an aggressive sales growth, you know, building the model kind of stuff, right? Like you found that that's your niche in general because that's what you like to do again, for fractional, right? Moving into your own business. What are the things you do presently to try and generate new business? Is it just LinkedIn? Is it SEO? Is it. Are you tick tocking like Scott with video? Like what are you, what are the things? Are you cold calling? Are you just sticking with old school? Like what, what are you doing?
It's funny because every time I try and figure out tick tock I get like 18 views on a video and I'm like, screw this, I'm done with it. So I keep coming back and forth to that and one day maybe I'll, I'll figure it out.
For me, Scott figured it out.
I'm gonna have to bug Scott more about this then because I am not there.
Yeah, I think the main one for me has been LinkedIn. Just because that's kind of where I've, I've been living and building my brand just for, just for shits essentially. And then it turned into, oh wait, this is something I can actually really use to generate business. This is cool. So that, that's been my main go to from there. I've always been a big proponent of partnerships. That's something I've always tried to drive whenever I've been at an organization, right. Like I'm all about low hanging fruit and I think fractionally when I move into an organization and work with them it's the same principle, right. Where can I get the quick wins to show some value immediately and build off of that? And I think I build my own business the same way where just starting with, you know, LinkedIn networking, who I know, and that turned into great. Who can I work with and have that kind of reciprocal quid pro quo type of thing. And I have found that with a few vendors that I work with as well, and then, then starting to work through communities and getting out there, I've, I neglected the physical in person communities and we're getting more and more of those since the pandemic kind of messed them all up. But having more of that here in Montreal, so trying to get out in front of people and meet with people is kind of where I've, I've been so far. And you know, I, I look at it and based on how much I charge and the number of clients I need, like if I can get four or five clients, I'm, I'm good. So I don't need to go high volume or I don't need to go the traditional route necessarily just yet. And that might change. But like where I'm at with the volume I'm looking for, just getting in front of the right people and having conversations has worked for me so far.
Yeah. The trick is staying in that right spot. So you keep having the right number of those conversations and I think what you find is that quote unquote, right spot is a moving target, is, is not to go too far at the deep end into surfing analogy, but like one of the hardest things about surfing is when you're out there is being in the right spot. And the best surfers oftentimes, what they understand is the wave dynamics and where the right takeoff spot is. And the people who struggle surfing are too far out or too in or too far to the left or too far to the right. And you don't just sit there, you're constantly paddling and moving, trying to stay in that right spot all the time. And that's the exhaustive part. Yes, right. And it's, it's a, it's a, you know, an on point analogy with what you're talking about. It's something that I think everybody struggles with. I struggle with it. You know, it's why I start experimenting with different things because I feel like the ground underneath me is moving and I'm like, oh, shoot, I'm not in the right spot. I need to shift and pivot. That's the, that's the frenetic Part about it.
Well, I think.
Go ahead, Chris. Go ahead.
I was gonna say, I think. I think you nailed it there because that's also the. That's also one of the big learnings I had in year one where I was like, oh, I'm really busy working on. Working with, you know, my clients, and that's great. And then one falls off and you go, okay. But I haven't been doing this other thing over here because I'm one person and I'm busy and everything starts to shift. And then if you shift too much in one direction as well, you kind of topple over.
Right.
Because if I spend too much time trying to get new business, then my clients start suffering. So it's. How do I find that. That piece of. That balance between the two, where I can be spending the time doing the business development versus spending time working with clients so that everybody stays happy, my portfolio stays full. And, like, that absolutely is a moving target that shifts regularly. And you have to find ways to weave that into your day to day to make it a habit so that you're constantly doing the right things as opposed to trying to flip. Flip back and forth and. And, you know, try and pivot too much, because I find that is very distracting as well.
Yeah, I had that shiny penny problem. Right. Scott's very good at this disciplined approach. He really, really, like, it's one of the things I truly admire about him and.
And wish I was better at, but I think it's. It's the athlete in him. It's that mindset where, like, all right, well, I gotta go hit a thousand backhands today. Yeah. Like, that's just the way it's going to be. So. But, Scott, I do want to come back to you. You know, it is called the surf and sales podcast, and it's okay to bring up a surfing analogy.
Yeah. We are allowed to bring.
I was like, why is he apologizing for bringing up a. It might be the first surf analogy we've had in six months anyway.
Talking.
To the guy whose water's frozen half of the year. So, like, you're gonna.
That's why I'm apologizing, because he doesn't live anywhere near, you know, moving water. It's all.
We. We. We have a solution for that, too. Call the surf, get him across the.
Pond, get him across.
Come on over, come to Europe, talk about that.
Well, cool. So. So I have a question for you. When did you decide to do. You sort of mentioned that. Okay, I realize this. I'm changing my job every year. What was the epiphany moment? Right? And there are two approaches. There are the approaches of, screw this, I'm going to go do this on my own, which was kind of my thing, sort of fall into it. Then there's Scott's approach where he kind of built it up alongside his regular job until he was comfortable that his income would be fine if he quit the real job. Right. Which is sort of that measured, disciplined approach. Were you building this on the side and did that kind of thing? Or was it like, you know what, Screw this. And regardless, when did you, what was the moment that made you go all in? What was the moment you're like this? I, I gotta do it this way.
It's funny hearing more about Scott's approach. I really idolize that and wish I was more like that. I feel like I fall more into your bucket with this one though, Richard.
Circumstances sometimes force it. So that, that was a little bit of my situation.
That was, that was very similar to my situation as well. And it was, it was interesting because I started like, even in my first role and I was, I was at aerotech for almost 10 years. I built a new division in Canada, hiring people, developing people. Seeing that number grow was really, really cool. And then I decided, hey, that was in the staffing industry. I want to, you know, take a crack at SaaS and started, you know, new organization there and started building stuff up. And it was, it was that motion of like, okay, cool, this is, this is figured out. Not that we're on cruise control, but like the team's team knows what they need to do. I just need to make sure that I'm staying on top of them. We're working through training and development stuff and that's cool, but like, I, I want a big mix up again. And that's when I would start going like, okay, a year here. Everything is settled. People are good. Cool, let me go do this again. People are settled, Everything's set. Cool, let me go do this again. And it was the last time around that I jumped in with a founder who came on board. I was ecstatic. The product was great. First couple weeks, I'm getting on the phone with clients and like, they're telling me how great their the product is. Getting on the phone with prospects and they're buying. I'm like, this is wonderful. And then my paycheck doesn't come. I was like, oh, that's kind of a cake in the nuts. Okay, dude, what's going on? Oh, yeah, you know, a couple Clients haven't paid us, and I gotta move some stuff around and, like, don't worry, you'll get it, like, in. I'll double you up the next paycheck. I'm so sorry about this. Whatever. All right, cool happens. Same thing, though, like, moving deals across the line. I was like, well, we're. We're making money somewhere because, like, I'm signing deals, so what's going on here? And same thing that next time around, money doesn't come in. At a certain point, I'm like, all right, dude. Like, I'm. I'm done. I'm not going to keep working until I get paid. And because I was the only salesperson, I'm building this out for him. I got that money pretty quick. But at that point, I'm like, well, like, we're done here, right? I'm not taking that risk again. And if I'm going to go through all of that and all of that bs, like, I'm just going to do it for myself. And that was kind of that circumstance that made me go like, if I can survive not getting paid and I can close my own deals and figure all this out, like, I'm just going to start doing that myself now. So that was kind of the trigger that made me go, like, I'm going to figure this out. And while I wish I had a little bit more of that business built up on the side a bit here and there, that would have been nice. But I did have. Actually, I did have one client essentially on the side, so that was a little bit of income, doing a couple paid posts here and there on LinkedIn. So that was a little bit of income. I met up with the. The dudes at Unicorn, who are our fractional agency, essentially. So they had a couple clients they needed a hand with, so I was able to jump in with them and do a little bit there. And that was starting to just get me a baseline of, like, hey, I could pay my mortgage and while I go out and do more. So I. I think that's something else that's really important to me is, you know, economies shift and times change is like, I feel really good about having more than one source of revenue. And that. That's really important to me because things pivot and things change all the time. And owning your own destiny is much, yeah, easier than being in. In one company that could very easily kick you out tomorrow. But it still doesn't feel great when it's like, yeah, I do this one thing, and that's where I make My money.
Yeah. Well, we're huge proponents of that. We talk about it all the time, so that's good to hear. And I think it's a mistake that some people make when they go into business for themselves. All of a sudden, they're like, I've got to be all in on this consulting thing. And they shut down all these other additional streams of income. For some reason, it's like, no, you don't want to do that. You have to have additional streams of income. Even if your own business is the main thing, you know, you don't totally. You don't just go to one stream because of that. What happens if something turns and that business that you're in, you know, isn't. Isn't as successful or isn't viable anymore? It's tough. It's tough. We appreciate you spending time with us, man. At the end of every show, we like to say, how can we be helpful to you? Do you have any questions for us? Stuff like that. So here we are. How can we best serve you?
Right on. So it's funny, I alluded before about scrolling through both of your LinkedIn pages and seeing just the cacophony of companies you've worked with advised for all that kind of stuff.
So big word, Big word.
It just came to me.
Got to get the thesaurus out. Make sure I use cornucopia. Yeah, cornucopia. There you go.
So I'm. I'm curious how a lot of those came to be. Like, Richard, you asked me the question before around, like, the business development piece. Like, is this. Are these things that happened organically? Are these very specific organizations? You're like, no, you. I want to work with you, and I think you're in a spot. I can help you. Or was it them coming to you after a certain point and saying, like, Scott, we know Scott. We want Scott to help us out with this. Like, where did some of that come from? And any advice around, you know, getting in front of the right people and that type of thing?
So it came from the fact that I had this marketing plan with a color palette and the right SEO approach.
Doing wrong this whole time. You want to send me a template for that, Richard?
Yes, I. I can send you my. My orange. My burnt orange and blue colors. Pantone color for scheme.
Great.
No, I got super lucky, right? I had somebody call and ask me for some help. I was in between jobs and interviewing and getting to, like, that fifth interview, but never getting the job. Someone called and asked me for help. I threw out this Ridiculous number. And they said, sure. And I was flying down to Austin.
And for a month and on my first flight back, I sat down next to a guy on the airplane. Turned out to be Nick Mater from gainsight. This is 13 years ago. Gangsite had 12 employees and all of a sudden I had two clients paying me each of the. I was working for each of them for 30 days and they were each paying me three months salary. So I had two clients and in 60 days I was making six months salary. I was like, what the. So I picked up the phone, I called John Barrows, who's a friend of mine, and he's like, dude, it doesn't happen this way. Go for it. And he also said like, I know you well enough to know you can do this. Go do this and talk to my wife. I built a validation website because I felt like I needed it and because I had customers, right? And it was very different. That that was my approach. I wasn't going out to my network, so to speak, and I was doing a little bit of cold calling, but then one client, but got the nextgot the next, they got the next. I started doing LinkedIn super early. I got super lucky in connecting with Sales Loft early, early in their days just to connect with them and went to their event. And I was like, gee, if I could go to this event and get a $5,000 deal, it'll pay for the event, right? Well, sat down at lunch next to somebody and sure enough, I got a $5,000 deal out of it and then met Max Altschuler at that event, who created Sales Hacker and was commenting on LinkedIn all the time. And then he came to me two months later and said, hey, I need help with these people who come in looking for sales training. And then I said, sure. And then he said, hey, do you want to start running our webinar? So, like, it all sort of fell in my lap in a very serendipitous way. And so my name got out there in a very different way, I think, than a lot of other people before LinkedIn became as saturated, right? When sales hacker get 400 people to register for a webinar and 200 would show up, and I'm posting, you know, four of them a month, and all of a sudden I'm getting business from all that. Like, so it happened very differently and organically for me through inbound, right?
So that, that was my approach to it and I just sort of winged it and figured it out. And I kept telling Scott for years, like, what the are you doing? Like, look at how much money you can be making and not have to be a slave to the grind. And the man in the machine.
And he's, as you can tell, he's much more reserved. He takes time to think it through and disciplines himself to do it in a different way.
But that, that's kind of how it all happened for me. So it was not.
The strategy fell upon me as much as I found the strategy. I don't even know if I found the strategy. It. It found me.
Well, it's funny you're saying, you know, Scott, you don't have to be a slave to the grind. You just have to sit next to some guy on a plane and like, next thing you know, right, you've got your own clothing business.
You gotta be in the right spot. That's. That's hard to do.
And by the way, I was using a Yahoo email address at that stage too, for those first two clients. I was like, oh, my God, I gotta get a business name. Like, it's Yahoo Looks. I didn't. I wasn't even cool enough to have a Gmail email address.
Hey, those were invite only for a little bit, right? Be somebody special to get one of those.
The, the, the thing that I.
Wanted when I first got into this is I did not believe or want.
To have to execute like, a big outbound strategy in order to be a consultant. And so whenever I talk to somebody who's doing consulting or coaching or whatever, and they have this big outbound play, I just think to myself, man, that's exhausting. Horrible, horrible and exhausting, et cetera, et cetera, et cetera.
I don't want that, and I don't.
Know how I could actually do that while also doing the fulfillment aspect of working with all these clients. I don't know how you'd have time for it, truly. So, um, I didn't want to go out on my own until I had a solid inbound, referral kind of motion. I really can't think of any clients that I've gotten in consulting from outbound. Like, I don't. I've never had to outbound, really. You know, I've done some outbounding stuff for community things of mine, surf and sales things of mine, stuff like that. But I'm not out there, you know, sending hundreds of emails and sequence things and cold calling founder. Like, I just don't think that that's the way for me. I didn't want to do that even if I could be successful with it. It just sounds horrible. I didn't work 20 years in this business in order to have to do that. And I think if it came down to it, and that was the only way forward for me to do what I do now, I think I'd probably stop doing what I do now, to be honest with you, because I don't think I'd enjoy it at that point in time. I'd rather go be a CRO and, you know, teach and lead and, and help people grow in their career and see if I can't get a big, huge exit one day, you know, so whenever.
Set yourself up for that too, though. Yeah, Set yourself up for that exit.
Yeah, yeah. As people should. This is one of the gripes I have with people going doing their own thing, like, too early. You know, I. I hear from these people all the time and they're like, how do you go get new clients? Like, you know, I've got three or four clients right now. I'm doing the work for them. I don't have time to prospect. And I'm like, yeah, I told you. I told you. You didn't. Wouldn't have time, you know, to do that. That's not. It's not going to be sustainable. Like, you're in trouble in that respect. So this is why growing your network matters so much. Producing content matters so much. Doing good work. So those people refer you. Other people matter so much. This is why partnering and having good relationships amongst peers and compatriots of yours like Richard and I, you know, don't do the exact same thing. So we have the opportunity to pass prospects to each other and vice versa and things like that. All of that stuff, you know, really, really matters in this ecosystem. I think so, yeah. That's. That's how I've gone about it and thought about it.
It is interesting, though, if you think about it too, that the amount of effort that we put into networking, hosting.
New newsletters, community, that is outbound prospecting, but it's in a way that we can control it and it's in a way that we feel like it's meaningful and supportive. It's not cold. I mean, it's still cold, so to speak, but it is, if you think about it, it is the same as it's a different type of outbound prospecting to drive inbound. Right. But I agree with you. It's exhausting to throw shit into the ether and, you know, pray that it might work to get someone to respond to you as opposed to, let me post stuff and build that brand and that name, which, you know, it sounds like. Chris, you. You figured out, too, it's a lot more fun, right?
Like, it's a lot more fun than crafting an email that nobody ever reads. Like, at least if I send out a post that nobody reads, like, I know it sucks because I see the eight people have seen it and I just start over from scratch. But, yeah, that's a big part of it as well. And I think, Scott, you kind of alluded to it too, where it's like, yeah, if I'm. If I'm gonna sit here and just call a thousand people a day to try and find clients, like, I'll just. I'll go back and I'll do that and get paid for it.
Right? I'll go baddie if I have to do that, even if I was getting paid for it.
So you'd have to be getting paid a lot.
Yes, indeed.
Order of magnitude lot. Well, thanks so much for spending time with us, Chris. The best way for people to get a hold of you is probably reach out on. On LinkedIn, I suppose.
Yeah, LinkedIn's still the best place.
There's no website. Right. All right.
So, Chris, Coney.com. i. I should at the very least maybe have that redirect to my LinkedIn or something. Maybe that's something. I'll go try and figure.
There you go. There you go.
It's actually.
All right, everybody. We appreciate you spending some time with us today on the surf and sales podcast, and we will see you all next time. And check out surfandsales.com. there are a couple open tickets left. Go leave a review on the podcast, subscribe to our YouTube channel, all that good stuff, and we will see you next time.
See everybody. Good to see you, Chris.
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