Episode 61: Jeff Chastain
Entrepreneur Conundrum Podcast
Jeff Chastain helps transform businesses.
EC 01 | 4min
About The Guest
Most entrepreneurial business leaders are experts in their field that struggle when it comes to the complexities that are involved in scaling their business with less than half of those businesses surviving more than five years.
As a business transformation coach, Jeff works with business leaders and their leadership team with two goals in mind: first to help them gain clarity in their business and second, to help them gain more of what they want to get out of their business.
Jeff has been working with business leaders for more than 15 years and has led multiple businesses himself before transitioning into coaching.
Jeff spent a number of years in the technology field as a fractional CTO. And he experienced the challenges facing entrepreneurial CEOs firsthand as they grasp that technology solutions, trying to solve underlying business issues by leveraging his own experiences, as well as the tools and resources created by other incredible minds in the entrepreneurial space to which Jeff coaches his clients.
Virginia: [00:00:00] Welcome to entrepreneur conundrum with Virginia Purnell, where growing entrepreneurs share how they get visible online. Hi everyone. Today, I’m talking with Jeff Chastain about how he helps transform businesses. Most entrepreneurial business leaders are experts in their field that struggle when it comes to the complexities that are involved in scaling their business with less than half of those businesses surviving more than five years as a business transformation coach, Jeff works with business leaders.
[00:00:29] And their leadership team with two goals in mind first to help them gain clarity in their business. And second, to help them gain more of what they want to get out of their business. And second to help them get more out of what they want out of their business. Jeff has been working with business leaders for more than 15 years and has led multiple businesses himself before transitioning into coaching.
[00:00:49] Jeff spent a number of years in the technology field as a fractional CTO. And he experienced the challenges facing entrepreneurial CEOs firsthand as they grasp that technology solutions, trying to solve underlying business issues by leveraging his own experiences, as well as the tools and resources created by other incredible minds in the entrepreneurial space, Jeff coaches, his clients .
[00:01:12] Through a spaced learning process designed to help them see benefits immediately while establishing a longterm cadence for predictable and stable growth. Welcome Jeff.
[00:01:22] Jeff: [00:01:22] Thank you very much. It’s good to have me out here and nice talk with you.
[00:01:26] Virginia: [00:01:26] Yeah, I’m glad you’re here today. So could you tell us a little bit, like how did you start off on your entrepreneurial journey and went out on your own.
[00:01:34] Jeff: [00:01:34] Well, mine was not the growing up. I always hated the go out and sell candy bars or whatever, kind of a thing. I was never that kind of person there. So I actually growing up my family life was always corporate America, that everybody don’t get the big corporate job and stay there forever. Nice benefits, all that kind of stuff and retire.
[00:01:54] And I made it, Oh, probably six, seven years into that journey and just said, okay, corporate America is not, for me. It was just too much politics, too much sitting in office cubes and having a couch Evers, little thought or decision or how else is going to work and fit with everybody else. So I took my leave at that point and did what most people do when they left corporate America and went and found a consulting company.
[00:02:15] So spent really actually about the last 15 years in some variety of consulting and now transition to the coaching there. But that was just the shift from, like I said, big fortune 500 company all the way down to basically running it yourself. And it was a mind shift there for sure. Kind of a thing, like you said, you’re used to.
[00:02:32] The solid paycheck. You’re used to the, honestly, not having a lot of control over the direction. And now basically you’re to the point of, okay, everything’s on me and it’s been its own roller coaster up and down, but it’s been a lot of fun for the last 15 years, but that’s really kind of where my transition when it wasn’t ever the, like I said the early childhood entrepreneurial mindset, I hear a lot of times
[00:02:54]Virginia: [00:02:54] you kept your lunch for yourself.
[00:02:56] Hey. Yeah. So what do you like most about what you do.
[00:03:02] Jeff: [00:03:02] Oh really today. It’s more about helping people cause it’s, I kind of went through it and learned it the hard way I had actually a doing consulting work all that time. But back in, I’m trying to remember what it was now, 2007 now started up a, an it managed services provider with my brother-in-law at the time.
[00:03:19] And we were both had long technology backgrounds, knew everything about operating systems and desktops and servers and everything. So. Of course, we could go start our own business there or start our own it services firm and things went well for a couple of years and then three years into it, basically it crashed.
[00:03:37] And it was a case of looking at it at the time of, we didn’t really know why short of the fact that we didn’t have any money. We basically burned all the cash. And unfortunately, some more beyond that. But looking back at it, it’s actually kind of the, I find it almost kind of the stereotypical that we weren’t effectively technicians.
[00:03:54] At that point, we knew technology. We knew how to solve technology issues, but going into business on your own, all of a sudden you got to deal with sales and marketing. You got to deal with finance. You got to figure out how to generate leads and do all this other stuff that goes into a business. That most entrepreneurs don’t necessarily have that wide of a background kind of a thing there.
[00:04:13] So that kind of set me on a journey of pilgrimage over the next five or so years to figure out, okay, why didn’t this work? And my original intent had been to go start a new company, build something else. And the more I got into studying this, it just turned into, okay, this is the systems, the process stuff that I love doing anyways.
[00:04:32] And what I can do with this is actually go back and help. The previous me, I’m trying to go into that company, figure out, okay, this is how you lay the foundation. This is actually how you systematize a business to grow it beyond just your lane of expertise and be able to build that solid business. So to me, the why is just beyond give back and hopefully help those, the people coming along, right.
[00:04:51] They’re trying to start their own business and say, okay, let’s make this successful. Give you some of the keys here that you may not necessarily be aware of because you’re, like I said, an expert in. Technology expert and medical expert in marketing, wherever, not necessarily the rest of the business.
[00:05:06] Virginia: [00:05:06] Yeah, for sure.
[00:05:08] So who is your ideal client then?
[00:05:10] Jeff: [00:05:10] Oh, really? It’s still somebody, honestly, that’s that same kind of growth oriented entrepreneurial kind of mindset. That’s like, Hey, I want to go build my better widget building a better mouse trap, whatever kind of a thing there. And it’s just somebody that’s really outgoing, wanting to go learn and say, okay, this is, I want to go make a difference myself.
[00:05:28] I want somebody personally here. I want somebody to just fund, to go work with fund. That’s got big ideas, big challenges, big visions there, but it’s like, okay, how are we going to get there? Inquisitive at that point. So really a lot of those early stage, both entrepreneur business leaders, as well as even almost into the mid market where they’ve had success.
[00:05:48] And now it’s okay, Just that frustration really, that I know there’s more potential here. I know I can do more with this company and I just can’t get to that next level for whatever reason. And that’s the point where I typically get to working with and talking with entrepreneurs, just say, okay.
[00:06:02] Yeah, there is more options. There’s solutions out there that we can do to really, again, going back to building systems and systematizing that business to take it to that next level.
[00:06:11] Virginia: [00:06:11] That’s cool. How do you get in front of those people?
[00:06:15] Jeff: [00:06:15] From a marketing standpoint and a person that loves systems, I would love to find the marketing system out there that you just do a, B, C, and D.
[00:06:23] And there’s the new person, but I have, after 15 years of looking for it, I kind of found it. I don’t think it exists out there. Unfortunately, most of my marketing and really everything I do is sort of conversations. It’s just meeting people and talking with people. Obviously I’ve been doing podcasting kind of stuff.
[00:06:38] Talking with you here for a couple of years now. I actually just launched my own podcast the first of the year, but it’s still, it’s just honestly, just getting out and having conversations with people because I find one of the areas of the biggest challenge that people have at this point is they know that there’s something missing out of business.
[00:06:54] They’d like I said, they know that they can, what, there’s more to it and more potential here, but they don’t necessarily know how to put their finger on it. It’s not that I can say, Hey, I obviously need search engine marketing. I obviously need a new sales coach, something here that they can point to and say, okay, this is, I know what the issue is.
[00:07:10] Help me go find it. What I’m working with really working with them from a system standpoint, it’s not something that most people really think about to say, okay, I need to systematize my business. I need to make sure it’s operations to operate here without me potentially here, where I can go take a vacation with my family or things like that.
[00:07:27] That’s not necessarily something they. Think about right off. So it’s really a, it’s almost more of an educational, something that I have conversations and start picking up on key highlights there to say pain points to say, Hey, this is what we’re struggling with. Okay. Let’s have a conversation about that.
[00:07:41] There. This might be more to it than you’re realizing or thinking about at that point.
[00:07:46] Virginia: [00:07:46] So do you usually let’s call it network or meet people through. Events or do you like do outreach on like LinkedIn or Facebook or anything,
[00:07:56] Jeff: [00:07:56] most of
[00:07:57] mine, I’m actually much more of the introvert type personality. So you’ve you stick me into a big event room with a hundred something people and it’s like, no, thank you.
[00:08:05] That just zap all my energy or 15 minutes, kind of a bang. So. I’d much rather go find one person and talk to them in the corner for that entire event, kind of a thing. And then try to sit there and talk to all groups. But I will do, we do webinars. I’m actually got a workshop coming up here in person on the thing, but even still that’s 20, maybe 25 people kind of a thing for a CEO breakfast.
[00:08:24] So it’s still smaller events. And then, yeah, a lot of LinkedIn, a lot of just anywhere I can make connections between two people and say, Hey. You’re looking for a fractional CFO. Do you need some financial help? Let’s make those connections. And just talking with people, working with people is really where we’re at happens most of the time.
[00:08:41] Virginia: [00:08:41] Well, it’s nice to know that you can still get together.
[00:08:46] Jeff: [00:08:46] Well, we’re getting closer. Yeah. It’s been a long year now. It’s interesting. Cause I’m trying to invite people over this breakfast that we’re doing. And it’s like so many people that even in the last month or so where we are getting back together, we met.
[00:08:58] Virtually over a resume over stuff like that. It’s like, okay, now I can actually meet you in person. We can actually transform some of these virtual relationships into in-person kind of a thing. So it’s interesting year for sure.
[00:09:09] Virginia: [00:09:09] Yeah, it is nice to meet in person, but sometimes it’s nice to be the virtual.
[00:09:15] Jeff: [00:09:15] I’m really curious to see kind of, I think we’ve kind of hit, went into the spectrum and we’ll start to pull back a little bit, but I’m not sure how much we’re going to pull back because the reality is obviously podcasting and stuff like this meetings like this, it’s opened up a geographic limitations for sure.
[00:09:30] And it also, if nothing else, it cuts down on travel time. You’re going to be in here in the Dallas area. I can spend an hour on each side of a meeting, just driving to go have some coffee with somebody it’s like, okay, if I get at least do the initial meeting, kind of make sure that this is worthwhile pursuing over zoom right now.
[00:09:47] And then yeah, we’ll do a face to face later on. I think that’s, I think a lot of people are seeing the value in that right now. It’s not going to replace obviously the face-to-face, but I think there’s some definite value out of. The technology that we’ve had to use the last year,
[00:10:01] Virginia: [00:10:01] your first date is going to be virtual.
[00:10:10] So is there like a common mistake? That you’re seeing a lot of your clients making or is it just kind of not really having systems in place?
[00:10:18] Jeff: [00:10:18] The thing that you find with a lot of entrepreneurs is we’ve got in some respects, you’ve got to have the healthy ego that I can do this. I can, I know that enough to make a business work.
[00:10:28] Otherwise you probably wouldn’t have jumped into business on your own in the first place, but it’s, to me, the challenge is figuring out, okay. At what point do I transition from being. That technician being the person. I was actually just had a, my podcast the other day. It’s like how do we transition from being the lawyer to actually running the law firm and running the law office and making that transition is to me, one of the hardest things that I had to do personally, and I’ve seen other entrepreneurs do to say, okay, it’s time to get this business to be more than just you.
[00:10:57] And the sooner you can make that transition and start delegating start. Building out the systems to bring in more people, things like that. That’s to me, the biggest roadblock on we all grow and scale business at that point is getting it stepping basically to be able to step away from it for honestly your own health and your own benefit.
[00:11:15] So you can go take a vacation, you can take a break and not have the whole business shut down, but at the same time, so you can really grow that business and get beyond just your own personal limitations.
[00:11:26] Virginia: [00:11:26] Yeah. Get out of the way. Yeah. So what couple of big goals that you have over the next one or two years with your company?
[00:11:35] Jeff: [00:11:35] Honestly, I’m looking almost in some respects kind of scale my own company as well. The, one of the ones that I’m actually working with right now, and we’re still playing with it. So don’t hold me to this one kind of a thing. But a lot of the coaching that we’ve been doing is just one-to-one. Which works for larger scale companies that typically have five, six, seven people leadership team, 30, 40 kind of employees.
[00:11:57] They’ve got the resources and everything to do full coaching engagements, but I’ve always had a passion for that. Almost the boutique kind of style. Size firms that are still kind of bordering in their earlier stages, looking to get beyond that 10 person realm. So we’re looking at branching into solutions there that are still more cost-effective that they can afford, but at the same time still bring a lot of those, the coaching values and a lot of the tools, a lot of the potentially a up here kind of set up there.
[00:12:23] So we’re still trying to figure out exactly how that’s going to work, but really looking to try to put together. Something that can go help that boutique kind of area, as well as our traditional coaching model. So that’s a second offshoot, I’d say of the business practice there that we’re looking to scale into and looking to grow into ourselves here in the next year.
[00:12:39] Hopefully even less than that, but here pretty quick. Okay.
[00:12:42] Virginia: [00:12:42] So with your boutique businesses that you mentioned, would you do like group coaching with them?
[00:12:47] Jeff: [00:12:47] The we haven’t got the structure completely built out. We’re looking at as almost kind of a group coaching plus peer council model together towards you’ve got still a small enough group that we can do some interaction one-on-one, but at the same time, it’s small enough that we can, or it’s still a group model that we can spread out coach and coach everybody at the same time.
[00:13:06] And then it also gives you the peer council ability to where. Effectively still at that stage, you’ve got other CEOs, other business leaders there to bounce off ideas of hold you accountable. Things like that, where a larger company might have that leadership team. I’m not in a house to make those calls.
[00:13:21] And that question now with the pure counsel ability, it’s almost a board of advisors, kind of a thing where you’ve got those other people that are saying, Hey, I’ve been down this road, don’t go down that road. Or why are you doing things that way? Why didn’t you make your numbers that you promise last quarter kind of a thing to help hold you accountable?
[00:13:37] Cause it’s a lot of that accountability is what I typically bring to a larger company to say, okay, I’m on the outside. I can say we set our goals, our metrics last year to hit these numbers. Why didn’t you hit them? Why aren’t you, why aren’t you following your own systems, your own guidelines there. And when you’re still in that boutique phase of being the only leader or the only CEO, there’s not anybody there to really hold you accountable or.
[00:13:58] Bounce ideas off of, so that’s one area we’re trying to kind of combine that with the coaching together and then bring more of a group style of similar solution there to those similar companies that were cost affordable price point.
[00:14:11] Virginia: [00:14:11] Well, that’s fun. How would that change your business?
[00:14:15] Jeff: [00:14:15] Well, it’s what it actually allows me to do.
[00:14:18] Honestly, just from a personal standpoint is quit turning people away that I’ve, like I said, in so much, well, I’m working with the larger scale clients because honestly they can pay the bills. I ended up turning people away saying, okay, the model I’ve got right now is just not a good fit for you at. A five person or a 10 person business, kind of a thing there.
[00:14:38] And it’s a problem, honestly, with my whole industry kind of a thing that we’re aiming typically aimed at a larger business there. And I always feel bad turning people away because I was in that same boat years back before kind of the thing I know the situation they’re in. It’s like, okay there’s gotta be a better way to help.
[00:14:54] So to me that’s the biggest draw to it is just again, while a way to give back a way to help. For those people, that, those companies, that, again, I was in that situation before.
[00:15:04] Virginia: [00:15:04] Well, hopefully you can reach back out to those people when you have you’re ready for them.
[00:15:08]Jeff: [00:15:08] We’re kind of in the beta mode right now, feeling things out.
[00:15:11] But yeah that’s the direction we’re going and that’s kind of a new direction here for the year.
[00:15:16] Virginia: [00:15:16] So, do you think there’s any roadblocks that are stopping you from like getting there?
[00:15:23] Jeff: [00:15:23] Yeah, I’d say a lot of them are, a lot of them are opening up. These stays. Cause that was kind of the question we were playing with for a long time was like, okay, do we really want to do this from a virtual standpoint, a virtual model?
[00:15:34] And we may still do. Some of that, just because by doing zoom meetings and stuff like that, people are, they’re used to it more now and more conducive. And like I said, it does open up the geography limitations, but at the same time we were talking about it before. There’s just a difference in being in a room face-to-face with.
[00:15:52] Eight or 10 kind of peer colleagues and talking with them versus doing this over a zoom meeting and things like that. It’s just not the same environment. So that was kind of one of the hesitations. One of the roadblocks we were looking at say, okay, do we really want to do yet another zoom meeting that everybody’s tired and burned out on?
[00:16:07] Whereas at least now down here in the Texas area, we’re starting to open things up when we start to put things back together and get some things in person. So I think that’s probably starting to work itself out, at least on that roadblock.
[00:16:19] Virginia: [00:16:19] So that’s good switching things off a little bit on you. What is the best advice that you have ever received?
[00:16:28] Jeff: [00:16:28] Really it’s boy, it goes so many different directions with that one. To me, it’s the, honestly, it’s the thing I see most entrepreneurs struggling with is the ability to delegate that it’s there as small business owners, especially in, I still find myself doing this that there’s so many different areas than okay.
[00:16:46] I can do the sales. I can go on and do the LinkedIn marketing. I can sit here and do the post-production on my podcast. I can do the website. I can do all this stuff. It’s like, okay, is that really? What’s driving the bottom line of the business. And the sooner you can realize that and get focused on that to say, okay, Yes, I could technically manage the website.
[00:17:03] I could technically do the post-production work on the podcast, but there’s probably somebody else that can do it better, faster. And for that matter, even cheaper than I can. And that frees me up really to spend more time on the clients, spend more time working with the clients and bottom line generating more revenue there, but that’s always, that’s one thing I struggled with early on and I hear on a consistent theme through my podcast and through talking with people as it’s just that.
[00:17:27] That ability and that challenge, just to be able to hand something off to somebody and say, okay, yes, I know this is part of your business. Part of this is your baby that you built, but it’s okay to bring somebody up sign and let them help you with that. I’ll take that on. And it’s okay. It’s just a struggle for that entrepreneur that says, Hey, I can do things.
[00:17:44] I want to micro the management kind of stuff. And even once you do bring something on, you’re still sitting there watching over is like, no that’s where you got to get the systems, the process and stuff like that in place where you can hand that off and. Really let go of it at that point. But yeah, that was, to me, that’s one the biggest challenges I ever dealt with.
[00:17:59] And the biggest ones is recommendations would say, yeah, the sooner you can start handing things off and trusting other people to pick up pieces and bring pieces along with you kind of a thing. So you can focus on your expertise. That’s when your business is going to kind of change and we’re going to be, we’ll really be able to grow.
[00:18:15] Virginia: [00:18:15] Yeah. It’s almost like they have that fear that they like no one else could do it as good as me. And it’s like, wow.
[00:18:23] Jeff: [00:18:23] In cases, maybe it’s not quite as good as you, or maybe it’s not quite as, as well, but at the same time, if it’s not the core of your business either. Okay. That side may not necessarily be an issue.
[00:18:39] Virginia: [00:18:39] What’s the best advice you’ve ever given.
[00:18:42] Jeff: [00:18:42] Honestly, me and in talking with entrepreneurs that goes back the same way. It’s still making sure you’re delegating, but really it’s from a business standpoint, business scaling standpoint, it’s literally looking at systems that I, it goes back to the Michael Gerber’s E-Myth, but it’s really treating the point at which you can say, okay.
[00:18:59] I’m going to treat my business as a franchise, even if I’m not planning on franchising it out. The idea of what the franchise, if you look at McDonald’s or Chick-fil-A stuff down here, the idea is that everything is systematized everything’s repeatable. So it’s not necessarily about the people that you can.
[00:19:14] Scale up the people, you can bring things in. If you’ve got those processes systematized and running, and the sooner you can look at your business that way and start running your business that way from a system standpoint, that’s the point really what you can grow and scale because, okay, now you can hand that off.
[00:19:31] Or now we can replicate this process and say, instead of one person doing sales, now we’ve got two or three. The systems are the same. They’re all working from the same blueprint, the same playbook there to go execute on whatever their job role is. But you’ve got that ability to sit there and add two, three, four people kind of a thing onto it there easily without having to sit there and reinvent the wheel kind of a thing every time.
[00:19:54] So the sooner you start looking at it from a systems perspective from really that kind of franchise. Lens. That’s really the key where it starts going from the small boutique firm, actually to a scaling firm and a scaling entrepreneurial firm at that point.
[00:20:08] Virginia: [00:20:08] Yeah. So true. Is there anything that you would like to share with us that I haven’t asked you yet?
[00:20:17] Jeff: [00:20:17] Oh, honestly, it’s the biggest thing I find with, again, just talking with the small business owners, the entrepreneurs is that it’s okay. A lot of my analogies and stuff I talk with people on is that it’s the model of climbing a mountain that okay. We’re the scaling of a business, growing of a business here as a client.
[00:20:32] It’s not something that happens overnight, but the reality is somebody climbed the mountain before you there’s processes. There’s ideas out there. There’s concepts. You don’t have to go reinvent the wheel all the time. And the sooner you ask for help, the sooner you look for help. Whether it’s in the systems, whether it’s, Hey, just bringing in a, an outside bookkeeper, cause you don’t necessarily know the financial models, whether it’s, whatever it is, the sooner you start asking for help and bringing in help the smoother, their journey will be honestly at that point and you can move it faster, but it’s just to me, things, the business has changed so much here in the last, even 10, 15 years, then all of a sudden we’re seeing a lot more.
[00:21:11] Of the idea of fractional resources that you don’t have to be big enough to go hire a full-time CFO or a full-time VP of sales. You can go get fractional resources. Now that can be just part-time resource versus, or just part-time advisors, kind of a thing there and guide you along the way it gets you that step up.
[00:21:29] Without having to have the super big resources. So again, it’s just a matter of looking for and asking for help sooner rather than later is just one of the key points. I’ll always working with business leaders on to say, okay, it doesn’t have to be just you don’t have to figure this all out on your own.
[00:21:43] It’s in most cases, honestly, it’s been before. So don’t reinvent the wheel.
[00:21:48] Virginia: [00:21:48] I had this vision in my mind about like, stay on the path, right? Like you don’t have to bushwhack, you can stay on the path like that is.
[00:21:58] Jeff: [00:21:58] And that’s the thing that’s one of the things I put out as most of the paths, most of their defined for you.
[00:22:03] You don’t have to walk the exact same footprints of the person in front of you, but the reality is most of those business Hills have been climbed already. They’ve been solved and addressed right there. To me, it’s almost the challenge. These days is almost the other end of the spectrum, that there is so much information out there that it’s the challenge of.
[00:22:18] Okay. How do I take all this stuff? And put it together for my system, for my approach. And that’s really honestly where I come in at that point, working with clients. Cause it’s, you can go out and figure it out yourself, but it’s a lot of time spent trying to put all the puzzle pieces together to form your picture of your puzzle right there.
[00:22:35] Virginia: [00:22:35] Yeah, for sure. Well, that’s cool. Thanks Jeff, for being with us today, where can people find out more about you and what you do?
[00:22:45] Jeff: [00:22:45] Oh, easiest reference is just company website is ed mentise, a D M E N T U s.com. And then we’ve got like I said, the podcast is building to scale. So we’re talking with really entrepreneurial kind of business leaders there as well.
[00:22:58] Just hearing, sharing their stories is dope. What were the challenges? What were the. The Hills you ran into in your business, kind of a thing there to help learn and help share from a story perspective there. So check that one out as well, but yeah, it’s just adventist.com and building the scale.com.
[00:23:12] Virginia: [00:23:12] Great.
[00:23:12] thank you, Jeff. Have a great day and we’ll catch you soon.
[00:23:15] Jeff: [00:23:15] Thank you.
[00:23:16] Virginia: [00:23:16] Thank you so much for joining us today. Be sure to subscribe and leave some love through a review and I’ll catch you on the next episode.
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