Building a Powerful and Scalable Coaching Program with Jeffrey Shaw

Jeffrey Shaw, an accomplished speaker and small business consultant whose self-employment journey began at the tender age of 14. Drawing from his background in portrait photography, Jeffrey guides entrepreneurs in seeing their businesses from a unique perspective and crafting strategies that lead to enduring success. He is a sought-after TEDx speaker and the host of the popular podcast, The Self Employed Life. Jeffrey has also penned two revolutionary books, The Self Employed Life and Lingo, which are designed to help business owners decipher the secret language of their target audience and make their businesses irresistible.

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Here’s the transcript:


Welcome to another episode of The Widest Net Podcast. I am your host, Pamela Slim and I am joined today by my guest, Jeffrey Shaw. How many people can say they have never worked for anybody else? Selling eggs door to door at 14 years old became a lifetime of self employment as a speaker and small business consultant. Jeffrey Shaw helps self employed and small business owners gain control of their business in what seems like otherwise uncontrollable circumstances.


Drawing on his experience as a renowned portrait photographer, like my father, Jeffrey shows business owners how to see business through a different lens and strategies to compose these often chaotic pieces of life and business into sustainable success. His TedX Lincoln Square talk is featured on and he’s the host of the top rated podcast the Self Employed Life, which I have been a guest on. Thank you very much. He’s the author of The Self Employed Life, Business and Personal Development Strategies That Create Sustainable Success and lingo. Discover your ideal customer’s secret language and make your business irresistible.


Jeffrey, welcome to the show. Pamela, I’m so excited to be here with you. And I forget your father was a photographer. It’s so cool. And we have matching Mini Coopers, so we’re just meant to be.




I was going to lead, saying we love the self employed, the color turquoise, turquoise Mini Coopers photography. I feel like you truly are my sibling from another coast. There you go. Perfect. I’d like that.


And it goes to what I just think is interesting. I have many people like this in my life where very often we can have clients who are talking to each of us about working with the other given the work that we do. And I always feel 100% great to say if you choose to work with Jeffrey, you are making a fantastic choice and I love that. Just knowing that you serve your clients so well. So just thanks for showing up that way.


And I feel like we’re aligned. Yeah, aligned in values and so forth. It’s just nice to know that it’s more about pun intended, having a wider net of peers to make sure our folks are taken care of. Yeah, perfect. I agree 100%.


I feel the same way. I’m always satisfied when I know one of my clients is now working with you and what have you. Yeah, perfect. I love that. Well, one of the themes that my podcast audience really loves the most is productized services.


And I’d love to dig in and dissect the work that has led up to your self employed business institute, your offering that you have, especially for coaches and consultants that are listening who want to shift their business model and so maybe just bring us into the evolution of your coaching work and the way that that’s informed the development of this model. Yeah, actually, great question to bring me all the way back to kind of the beginning of speaking. So because I was first and foremost in the photo industry when I started speaking in 2008, 2009 or so. The photo industry, like a lot of times when you’re a speaker within your industry, they don’t pay or they pay very little to in industry speakers. So what I learned really quickly was that the money wasn’t to be made as a speaker, that it was going to be by speaking, I would build my coaching practice.


So I learned the importance of productized services and having back end services very early on. I also feel like I learned the art of how to do that in a clean way. I had many sponsors and such in the photo industry that wanted to sponsor or sponsor me behind in the background. But I always said your logo won’t be on my slides and there won’t be a banner at the beginning in the front of the room or the entrance into the room at that end. I would only be sponsored by people whose products I actually use.



Therefore I could work them into stories that I was going to tell. So I would just bring their products and services into my stories and therefore people would appreciate the value they bring. So now I realize how meaningful of an experience that was that I learned early on that you needed this backend that became incredibly valuable when I launched my books, because a lot of people don’t whether they set out as a speaker, as an author, they don’t have those back end services that they may need to round out their business model. So I was kind of gifted with the experience of knowing I had to figure that out early on. However, I will say that even to this day, it’s still a surprise to me sometimes as intentional as you can be.


So with my first book Lingo, first time author, I didn’t really think about the products that could come from that. I just put the book out in the world. And actually my intention was to get more speaking gigs from having a book out in the world, or as I often refer to as my book Lingo is kind of my calling card out of the photo industry. It was my first time putting a stake in the ground outside of the photo industry. It didn’t really lead to a lot of speaking gigs.


What it led to, surprisingly, were people reaching out to me saying, hey, I would love to work with you on the brand messaging on my website. So it created itself with the self employed life. I had an intention to create those services, but as it turned out, people didn’t want what I created. I was thinking I could create a three month program, one to one, that would walk people through the self employed ecosystem as I teach in the book. And while some people grabbed that, what I realized real quickly, people were asking for community self-employed people wanted to hang out with those self-employed people.


So that’s why I pivoted pretty quickly and decided to create the Self Employed Business Institute, also realizing there was a major lack, and I know that you know this, it actually came from a conversation with a mutual friend of ours, Leslie M. I was chatting with Leslie and just sharing, just sharing with her. That my experience that in my 15 years or so of coaching, while I had coached people in all different industries, they all had one thing in common, and that one thing was they were all really good at what they do, but they were in industries where nobody taught them how to make money at what they do. And I was sharing my frustration with that. I said, Somebody needs to fix this.


And she said, Why not you? And I said, you’re right. Why not me? And that literally was the impetus for creating the Self Employed Business Institute, which is taking all those services that I offer and turning it into a product and a program. I love that so much.


So tell us about the different components. What are they, and how did you experiment with the order? You don’t have, of course, to cover every topic that you cover, but I’m always interested behind the scenes of just how you decide what to include, how to structure it? What was that evolution? Well, the first thing I did, which is what I highly recommend to anyone, is, of course, I did a beta version first.


The hardest thing for me, and I think this for many of us is, or it is for me anyway, is I always say I’m the complete opposite of a procrastinator. I get everything done early. And it took me a long time to figure out, why am I such a non procrastinator? It’s because I live in a deep fear of not being prepared. It’s not particularly healthy to not be a non procrastinator, especially when it’s rooted in another anxiety issue.


Right. But really, I have such a fear of not being prepared. I’m always way over prepared. Just get things done ahead of time so you’re never late. I’ve been like that since I was a kid.


So the hardest thing for me is to create something that I’m going to create as I go. It’s just so against my personality, but that’s the advantage of collaborating and co-creating with the people you’re going to serve. So, of course, I did a beta version. I had prepared, I think, the first two classes only. I would not let myself go beyond the first two classes and then created in the moment based on what they needed and what they needed, and built the next one.


So it was doing it on the fly because the training calls per the structure. The training calls are every other week, so I wasn’t giving myself a lot of time to create an entire curriculum over five months. It was a five month curriculum. But without a doubt, that is absolutely the best way to create something that truly services people is to co-create with them. And that’s the whole point of doing a beta version.


So one thing I was very clear on, because it’s the way I like to coach, is that it was going to be both group and one to one. So that’s exactly what the structure of it is. We have two training calls per month and each student has a 30 minute one to one call with me every month. And then there are two open coaching calls per month. And for me, that’s a blend that, hey, I know it doesn’t work for everybody, but for me, I am most comfortable when I take advantage of the advantages of both.


Group coaching has an energy to it. It has the community. I love bringing in other people’s voices and thoughts. And I also know there are commonalities, no matter what the industry is, there are commonalities in business, particularly self employed business, that can be taught and every person needs to be respected for their individuality and their individual goals. That’s why I have a very strong one to one component as well, where I can really make sure we’re addressing people’s individual needs.


So that was a definite. When I first started, the open coaching calls were more sporadic. It was kind of a surprise, like almost an added value, like, hey, I’m going to be online, join me. But then I realized that what my people needed was more structure because they are business owners. So rather than just on the fly, let’s have an open coaching call.


I decided to make it structured on the first and third Wednesday of every month, right? So I made it structured for those open coaching calls so more people could take advantage of it. I’ll blend it with the one to one, blend it with the community that we have online. So those are the components of it. This is a very specific question, but for many people, the first time that they’re rolling out an offering, you know this as a marketer and a brander, there is this fine line when people are choosing to be investing.


Their resources in a program between realizing that they’re co-creating and seeing the value in that, but also not wanting to feel like they’re investing in something totally new that isn’t proven. And I’m curious what language that you used when you were recruiting your first cohort to go through it. I talk with clients all the time. Some call it a beta, some people call it a pilot. And that can be accurate.


But sometimes it also is not actually demonstrating the value that you are bringing as a very seasoned coach. So how did you navigate that between being open and it not being perfect, but helping people to recognize that they were going to get a high quality experience. Yeah. I have to say, to me, the easiest cohort to fill up was the first one. Right.


It was to me because I was so genuinely excited that the excitement just cut through everything else. Hey, I didn’t know where it was going to go. I didn’t know it. And yeah, it was discounted a little bit from what would become the full price, but it was still a healthy price. But there was more than anything, it was just my genuine excitement about what was going to be created.


And because of what I was creating, I really took the community angle. I really wanted people to feel like they are part of a movement, that they are part of the building of a community of self employed business owners so that they felt I just find people overall are so much kinder than we sometimes hear that they are. I find people are far more genuinely interested in helping people of like, mind and like, experience. So I just really leaned into A, how excited I was about it, and B that we were building something together and it was kind of a movement.


I didn’t sense any expression from anybody, any concern about it being anything less than perfect. In fact, I think today people like the rawness. I think we’re not looking for perfection. Right. And I try to remember that even today in my teaching, I always remind myself, and I say it often, I want to teach from an in the trenches perspective.


And in order to do that, Pamela and I think you may operate in a similar way. The term I use myself internally is I always feel like I have to drop in. There’s a truth deep within us. I have to remind myself, don’t just recite what you think or don’t just recite what you may have heard or that work. I try to remind myself all the time, like, drop in to what is the truth of how this can be done.


Even like business strategies to cut through the noise that we hear from so many different sources, but just kind of get to a truth, so that you can teach people in real tangible ways that are actually applicable. So I’m rarely looking for perfection, and I certainly wasn’t putting out a beta version. And I believe my people just fully accepted that and even embraced the possibility of it being raw and fresh and new and rougher on the edges, but just the way it should be. I appreciate that it does align with adult learning theory, which is that when people are leveraging their own experience, treated as partners, as opposed to just a passive learner, you actually do get the wisdom that they’re bringing to that experience, which is to me, one of my favorite parts of teaching a group. Each group has such amazing experience and I always learned so many new things, new insights, new applications.


But it is something I think your story is going to be helpful for people that can feel anxiety about. Like, how could I possibly put something out that is not perfect? I tend to work probably like you with a lot of people who are very high achieving and have great ideas, which is wonderful. But I call it sometimes when strengths attack, when their strengths can stop them from moving forward because you just need, as you demonstrated, to follow the path test and try things and then begin to get the method more solid as you’ve gone through different iterations. Now, what is the high level structure of the things that you have found that really are the critical kinds of content that you cover for folks?


So I look at it as an ecosystem. It’s one thing I grew tired of being self-employed is trying to put together all the pieces from all different directions, right? I mean, the seminars, the convention, the different directions we would go in to try to put together all the pieces of the business without fully appreciating how integrated it all is and how exhausting it is when you’re running all over the place.


What I’ve created is a curriculum that’s very well rounded, starting with we work with personal development mindsets, but again, all the things we hear about. But I do believe my approach is different. Again, always trying to cut to the core. We don’t, for example, in trying to get people to get really motivated to make the changes that they have identified they want, right? They’ve identified the change they want in their business, but in order to get them to really step into making that change.


Because I’m going to be their biggest advocate for the next five months of the curriculum, rather than a fluffed up class and conversation about motivation and dangling carrots and visions and goal settings. I put that aside and I’m like, okay, let’s get really clear on what you have grown to hate so much that you want to get away from it, because that’s going to be the real impetus for change. Are you tired of being overworked? Are you tired of not having enough time with your family? Are you really sick and tired of, is the money all going to match up this month?


Are you going to have enough? What are you so sick and tired of that you’re actually willing to put in the work with my support and with my guidance, but put in the work to make the difference? So I just tend to approach things that way rather than the fluffed up version. Same thing. We have a whole class on intentions, but I don’t let people get caught up in their own minds in the fluffy version of intentions.


I have a very specific format, from to. I want to go from this to that, I intend to go from this to that and actually we have provided a workbook. So it’s very cut and dry. So the curriculum is we start with really trying to get to the real root of the motivation and the changes they want to make. So that when we get into the actual business strategy, which covers about two for about two months, we’re focusing on my system of marketing, which I refer to as “hug marketing”, multi levels, multifaceted. And we go through it step by step and actually build out the assets people need, right?


So we’re building out the lead magnet. So we’re not just conceptualizing it, they’re not just learning what a lead magnet is, but actually creating an effective lead magnet, an effective meaning. It’s compelling. It’s of super high value to the people they want to serve. And it’s actually leading, which is amazing how often people forget that it’s actually leading to where you want people to go, right, to be served by you at a higher level.



So we work out that content marketing strategy, email marketing strategy. So we’re actually ticking the boxes of building out the assets. Brand messaging, website development. I think every student has needed to tweak, if not completely redo their website because they realize how broken it is and how ineffective what they have is. I want to correct that.


Business model, one of my favorite sections, and actually this actually ties into our previous conversation. Let me tell you a little story about this one. So, in the first cohort, when I taught Business model, I instinctively, as we often do as coaches, I instinctively had something I wanted to say about business model. And on the surface I presented it as being self employed business owners, which most of us are bootstrapping and funding our own businesses to start with.


We’re not going to banks. I was like, we don’t need a business model for a bank presentation. So I thought, what kind of business model do we need? And I started there was a perspective I was coming from, but I knew after that first class, for the first cohort, something was nagging at me. There was something I wasn’t getting across that I wanted it to be better, which is why we do the beta version.


Took me a while to unpack it. And what I realized, why I was stressing the importance I just sensed that the importance of my version of a business model. My sense was it wasn’t coming through. The importance of it wasn’t coming through. And I realized what it was is that as self employed business owners and purpose driven entrepreneurs, we literally need a business model that is turned upside down from the norm.


Because in normal business, business models are built, they’re income based. You’re making your decisions from an income perspective. Every self employed person I work with is impact based. They lead with the work they most want to do, the way they want to impact people’s lives. And when you are running a business that is impact based.


If making an impact is on the forefront of your mind, you’re likely putting time, money and energy into things long before the income catches up, right? So a traditional coach would come along and say you’re wasting your time because you’re not getting enough ROI. And what I prefer to do is set up a process where you’re leading with your impact and the systems are in place that the income will follow and you trust that it will and you know that it will because you’ve done the right things. But I think we have to this to me is for anybody that’s purpose driven, heart centered in their business, we have to lead with impact and have an impact based business model, trust and income will follow. It’s so true.


I find a very similar thing with my folks and I love looking at the way that you begin to address the underlying, the surface level. There are so many assumptions I find that come with program design in coaching where either it’s all mindset, so you just have to have the right mindset and everything else will happen to which anybody who’s done it for a while will just chuckle like it is more than that. And at the same time, mindset clarity of thinking is exceptionally important, especially in driving your focus, your actions, but also your feeling and your experience of going through it. Also, as you said, I love your perspective is always having been a self-employed person, not coming from corporate like I did, like probably many of your clients did, where there can be a very different understanding of actually what it takes to be in business. Years ago, when I wrote Escape from Cubicle Nation, one of the lines I would often quote when I was promoting the book is hating your job intensely is not a business plan.


And there’s this miraculous thinking kind of thing sometimes that people are coming from corporate, which has its own unique challenges, of course, but sometimes you don’t realize all of the support and structure that’s baked into being in a corporate role. Having other staff, having endless office supplies, just being able to take paid vacations without worrying how you’re going to bring in income. So I like how your unique point of view, both as a creative person, a highly valued creative person in your photography and your branding is coming together with cutting through the noise of just giving surface level advice for people because you know what it’s like when you have to be generating your own revenue. And I just feel like that is such an important piece of, as you were saying, what’s really underneath a surface. And I love that dropping into what actually is the experience that people are having.


And how can you acknowledge, for example, it is very stressful when you’re doing a lot of activity and you don’t necessarily see the dollars coming through. But how do you determine when you are on that right path to just keep going versus when maybe you need to shift direction? Yeah, and that is one of the biggest challenges. And I like to suggest that you give everything at least a try three times, right? So that you can really test it the first time.


You’re just branching out, but you kind of need information. But I do think even today that is one of the hardest things to know is when your stubbornness and persistence is paying off for you or when you need to cut your losses. But to your point about corporate, because I see this all the time and this is where I’d like to intervene. People leave corporate for all the reasons that they’re leaving corporate and then they become self employed and they actually recreate the same environment a lot of times and makes sense, right? It’s the place from which they know.


But that is exactly where I think a lot of times they get hung up. The compartmentalized way of thinking that existed in corporate and the fact that they were siloed out in their own little role, suddenly they were in a role as a business owner that is much broader than that, much more all encompassing, and that can really throw them. So there’s a little bit of a deprogramming part that needs to go on when people left corporate. But at the same time, I’m always encouraging people to not shut off what they know to make, to connect all those dots. I find a lot of people are driven to leave their corporate job to become self employed because in their current work and their current position, they feel they see a way of doing what they do better than their current place of employment.


Right. They see a way that they can do it better, they can be more helpful, more impactful. So don’t lose sight of that. If you have a different way of doing it, that’s when it becomes a problem. They leave and they just recreate the same thing and that’s when they don’t allow themselves to stand out enough.


But you need that information from your past in order to move forward as well. So it’s not a matter of shutting the door on your corporate experience, which I have seen people have a tendency to do, usually because I say people stay three years longer than they probably should have, right? It takes a long time to convince oneself to make such a big leap that sometimes by the time they actually do make the leap, they’re three years into pretty heavy frustration. So sometimes they can try to close the door a little too quickly. I agree.


In Body Of Work, I call it the Loathing scale. So if you imagine one is you jump out of bed to run into work and you love it. And then you feel physically ill when you even think about working. I always tell people, when you start to get to the six seven range of a Loathing scale, you need to very proactively begin to work it. Because if you get higher, either you get physically sick or you have a Jerry Maguire moment, right?


You make a big speech, say something you don’t want to, and can really damage your reputation. So I think that is really important. I want to talk for a second. Before we started recording, we were talking about marketing cycles. So we’ve talked about the design of the program, of having the experience you gain working one on one with people doing the beta to begin to really test and see what’s the right order in which to do things.


You begin to get a good clarity about the structure. That’s required adding some more specific structure to support folks, for example, with your drop in calls. What did you learn in the marketing cycles? This is another area that’s so hard for people to figure out. How did you start marketing the program and what is the current model that you’ve shifted to?


So I think the big learning lesson in this for me and probably for many others, is be careful what you ask for or be careful what you create, right? So when I, as someone who transitioned from photography into coaching, one of the biggest drivers for me over the last several years has been consistency. I mean, as a photographer, I had an extremely seasonal business. I did 70% of my annual income in three months at the end of the year. So it was a very seasonal business.


And hey, maybe I had the stomach for it in my thirties and forties, but it was, I would say I was a modern day farmer. I was harvesting cash because I’d make all my money at the end of the year. And I was a photographer on location in the northeast. So I did no photography, January through April, which is great. I took time off, I hung out with my kids.



But it was extremely seasonal and I just tired of it. I got to a point in my life where I kept saying I would just love to have a steady paycheck, I would love to have just a steady income. I got tired of the seasonality. It’s a lot to manage. So that’s one of the things I’ve loved about coaching.



It is by and large, we have little ups and downs, but it’s pretty consistent. But then I created this Self Employed Business Institute with the original intention of being two cohorts per year, March and September. So guess what? I ended up creating a seasonal business for myself again, which is exactly what I wanted to get away from. And it took me four or five cohorts to realize what I had created.



That I created this emphasis the importance of a big launch twice a year. And if. Either one of those launches didn’t go well, it could potentially be disastrous. And it was exactly the pressure I didn’t want. Add to that, there’s a huge marketing challenge in that because your marketing is another roller coaster.



It was ramping it up, it was slowing it down. Whether it was Facebook ads or LinkedIn outreach, all the different ways in which we were meeting people and just reconnecting with people and getting referrals, it was again this up and down cycle. So I realized that I just in my quest to have things more and it was, I should say, really, I have to say that probably the most important lesson in this was listening. Novel idea, right? The most common objection we would hear when reaching out to prospective students was timing.



It’s not the right time for me. I had just joined a program, I just hired a coach. Now, sometimes I think timing is an excuse and from their perspective, the timing is real. And I realized from a marketing perspective, I don’t know, I almost want to say you’re really thinking a lot of yourself. I’m speaking about myself.



You’re really thinking a lot of yourself if you think you’re going to get the timing right twice a year for enough people. And that was a big factor for me. I’m like if timing is the biggest obstacle for people, whether it’s real or implied on their part, that’s up to them because it’s their world, their decision. I decided to remove that objection by instead of doing two cohorts every year, we now launch a smaller cohort every other month. So this way nobody is ever more than a month away from the next opportunity.



We actually welcome students within the first month of a new cohort. We will allow people to join because I can bring them up to speed in the first month really easily, but not after that. So between allowing people to join in the first month and the next cohort being no more than two months away, there’s never more than a month that somebody has to wait. So this way I feel like I’ve increased the opportunity for the timing to be right, for people to help themselves throughout the year. And it’s evened out our market now.



We market all year long now. We market continuously every day. We’re taking those tiny steps towards bringing in students, meeting people, outreach. It’s just constant. And it not only has satisfied my own desires, I realize it’s just as I said, the biggest deal to me was it was addressing the reality of the world that people are ready at a different time.



And one thing I had learned over the years as a marketer, which is why I always tell my clients, keep marketing, keep marketing and keep in a gentle, kind way, keep reaching out to people. Because there are many times in my own life that meant nothing to you. A month ago means everything to you this month. And so I feel like with the continuity of the marketing that we’re doing now, hey, somebody can have a great quarter. Q1 could be great.



Q2 could come along and they suddenly could see the value in what we have to offer that they didn’t see the previous quarter. So this is really I’m really enjoying the process, and I feel like every day I get to have wonderful conversations with people. It’s not this big up and down. So that’s been a really significant change. Instead of the twice a year launches every other month and focusing on not caring about how big they are now, they can be cohorts of five to eight people, six people, and there’s a richness to that too.



I think people have come to really value the even smaller cohorts. I really love that it does even out for many people, which just does become hard to sustain physically and emotionally is the big roller coaster of launches. And as we’ve seen with either large scale economic issues or social issues. Whether it just feels like in these past number of years, there are such bigger, disruptive forces that can really impact, for example, when your book’s coming out or what’s happening. As you said, if you’re just putting all your eggs in one basket to launch a program, And I just love that reinforcement of a message that I know I’m internalizing in my own business and also working with my clients on that.



It does take much longer than you think for people to actually understand what you do. And that is where you do maintain that consistency. Whereas in the past we can have a sense sometimes that what if that whole pool just dries up? Isn’t everybody I know just going to know about my offering and nothing will happen? That will be the case if you don’t take any steps in order to expand your audience.



But as you’re saying, if you’re just really focusing on this message in a holistic way, then for people who have been in your circle, who weren’t ready yet, exactly as you said, they can join the next time. You’ve probably had situations like me where you just reintroduce or you check in with a friend who you’ve known forever, and they’re like, oh, what are you up to? And you say, oh, this is what I’m doing. And they’re like, oh my gosh, that’s what you’re doing right now? Can I work with you?



Or vice versa? I’ve done it. It’s the same hired people who I’ve known because I didn’t realize that they took a little bit of a shift. That was exactly what I needed in that moment. And I’m glad you brought in exactly.



I think sometimes as business owners, we forget we’re consumers, right? So I actually try to pay attention to my own mindsets, my own experiences in the world, and also my own buying patterns. And I realize that there have been many times that I’ve brushed something off as something I didn’t need. And all of a sudden I’m like, that’s exactly what I need. I never believe I’m the only one that thinks a certain way.



But I’m also glad you brought in the well being and the self care because that was definitely a big factor of it. And I think sometimes I forget to remind myself of that, that I was very aware of the emotional and physical toll that two big launches a year was taking. And that’s not how I choose to live. And I’ve always said every business decision I’ve ever made is first based on a lifestyle decision. And I wanted to put my well being.



And again, at this point in my life, I’m just looking for consistent, everyday well being, everyday success in business, and just everyday income. So it’s just all steady and consistent. Hey, maybe it’s boring, but I’d say at this time of life, I’ve ridden the roller coaster for decades. At this point in my life, people offer it sounds crazy, people offer to pay the program in full because it’s automatically broken up over six payments and people will say, Can I just pay in full? And I’m like, Darn, I really like it when it comes in every month.



I’m that focused on consistency and steady. It’s like, oh, please don’t pay me in full because I’d rather get the payment every month. That’s right. It’s so beautiful. Whereas in the past it would have been great.



How can I get as much as possible coming in? Exactly. Yeah, that’s wonderful. Well, this is part of thinking about well being in your own business. I was so happy connecting with your daughter to set up this podcast interview.



So now is your daughter working with you in your company? I know for a lot of listeners are curious about that. I know my 15 year old Angie and I have recently been talking about maybe some things she can do in business, what’s that experience been like to be working with your daughter. It is such a cool story. So she actually has been working for me, with me for a couple of years, virtually because she was living in Connecticut and I was living in Miami and have been for seven years I was living in Miami.



And so last couple of years we worked virtually, and last August I rented a house in Connecticut for the month to just spend a month up in Connecticut as well as have her come over to the house I was renting every day so we could work side by side. And we loved working side by side. And one of the greatest blessings in life is when you have a child that you can spend every day with. We hang out all weekend too. I can spend every day with her and I never get tired of being with her.



We’re just a really great blend of personalities. And I have to say, so the experience is terrific. And there’s another layer to it that is really important. I built my photography business. It was a hustle, it was a lot of work.



I did the best I could as a young father. I became a father at 28 years old. I had my kids all by my early 30s building a business. And I never felt at the time that I sacrificed time with my kids for my job. But you know what they do.



And there were times I don’t think I missed big, important events, but clearly I missed some parts of life that were insignificant to them, even if it was just an evening dinner. So I realized that the impact of building a successful business had a little more toll, more of a toll on my young family than I had thought until I got older. So that was a part of it. But I also realized that none of my kids would want anything to do with my photography business because they saw the amount of effort and work that went into it. So, thankfully, they all are very independent and doing their own thing, but none of them went into the corporate world, but they did see the amount of work that it takes to run a business.



So from a legacy perspective, I really wanted Claire to be a part of the building of this business so that she saw the building of it from the beginning, because I didn’t feel like any of my kids really saw the building of what I built that I think I’m really proud of as a photographer. I built something really significant and they never saw the inside. Whether leaving photographs all over the world is a legacy, but I never felt like I left a legacy that really meant something to me, which is that my kids saw what I built. So it’s really important for me to have Claire inside the business as we’re building out the Self Employed Business Institute. She’s the Dean of Students on that end.



She’s also my EA, so she’s really seeing the building of it from the inside and where the future goes. Who knows whether I will sell it, whether she’ll take it over, whether we’ll sell it together, I don’t know. But having her on the inside as we build this, this feels more to me like a legacy than any legacy I may have left as a photographer and all the portraits I created for other people. So I have to say, the experience on a day to day basis is wonderful. And it really fulfills something for me on a personal level that they didn’t have in my previous business.



It’s so encouraging and it’s so exciting. I was super close with my dad, so I love that I know he was so important to me and I would always love to spend time with him in his photography business, but also all his community activities. So I just know how important that is in a relationship of a daughter and father or son and father. And the other thing is just I know for a lot of people, much like you said, your clients are looking for impact in their work. It’s also looking to have more integration in their life.



It is a tip you probably give to folks that people may realize you can pay your children even if they’re quite younger in the business, and get some tax benefits from that. There’s some good tax advice for that. I always encourage you to make sure they’re doing some work so they don’t think they just get a paycheck for nothing. But it is really encouraging, and I love to see that model.



I see with Angie that she has a more self-employed sort of vibe to her. She actually loves to hang out with me. She loves to travel. I could see her being excited about that. She has more of a design background.



Our son Josh is going into the field of public health, but who knows, maybe down the road, she could be working directly with me in the business after college. So I love that modeling. It is incredibly satisfying. And I have to say, on a daily basis, it seems like on a daily basis, Claire will say, I had no idea how much went into this. And again, every time I grinned, because that’s exactly it.



It was easy to reap the rewards of the successful business I built as a photographer, but they had no idea what went into it. So what they saw was the father wasn’t around as much as they would like, where now what she’s getting to see is the thinking behind it. It’s brought it to my attention, too, about sometimes I’ve patted myself on the back and said, okay, I’m smarter than I thought, right, because I’m taking things. And through her eyes, I’m getting to see what she’s seeing is like, why did you think of that? How did you come up with that?



A lot more goes into this than she thought, so it’s incredibly satisfying, for sure. That’s so neat. Well, where can people find you and connect with you? So we’ve spoken a lot about the business institute, so is one place to start. My main website is, and one thing always leads to the other.



So no matter where you start, hopefully you will feel a part of the whole community that we are building on behalf of self employed people. Wonderful. Well, thank you, Jeffrey, for sharing your time with us today. For those of you who are listening, make sure to check out the Show Notes at We’ll include all the links that Jeffrey and I talked about today.



I want to thank our 31 Marketplace production team La’Vista Jones, Tanika Lothery, Jose Arboledo, and our award winning narrator Andia Winslow. Until next time. Be sure to subscribe to the show and enjoy building partnerships, organizations and communities that grow our ecosystem.

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