The Book of Balance · 2026-03-02 · 55 min
Key moments - from our scoring
Substance score
32 / 100
Five dimensions, 20 points each
Tony Caldwell's journey from 27 years in the U.S. Army - including nearly 11 years at the Pentagon working on organizational design - to founding the 2326 Group reveals critical lessons for military-to-entrepreneur transitions. After retiring in 2015 and working through several corporate roles, including as a contractor teaching organizational design and positions at two banks, Caldwell realized his last job would be his last in corporate. The acquisition he joined fell through, prompting him to launch his consulting practice. His initial concept - coaching first-time managers through their leadership transition - found limited market demand, so he pivoted. Now he works with entrepreneurs and mid-career professionals seeking C-suite advancement, while simultaneously building a public speaking and facilitation practice through organic requests from clients and community groups. Caldwell emphasizes that entrepreneurs need a strong *strategic* vision (impact-driven outcomes) rather than rigid operational plans, and must remain agile when market feedback contradicts their ideal client profile. He advocates heavily for building a "campfire tribe" - a peer network beyond transactional relationships, citing his experience at Flywheel coworking space in Concord, North Carolina. For solopreneurs especially, this network provides mentorship, accountability, and the perspective needed to balance passion with profitability using the Venn diagram framework: what you're good at, what you enjoy, and what people will pay for.
Tony Caldwell spent 27 years in the Army and found that military discipline, organizational design expertise, and execution-focused culture transfer well to corporate and entrepreneurial settings. Veterans are trained to execute clear objectives efficiently and independently, making them valuable assets; the key is hiring them and delegating clearly without micromanaging.
The market didn't respond to his initial idea of coaching new leaders transitioning to management roles. He discovered that while businesses recognized the problem, they rarely paid external consultants to solve it. This feedback led him to focus on coaching entrepreneurs and mid-level professionals seeking advancement, and eventually into public speaking through organic requests from clients.
He uses a Venn diagram of three circles: what you're good at, what you enjoy doing, and what people will pay you to do. Only the intersection of all three - not passion alone - represents a viable business. He emphasizes that passion doesn't equate to profit without market demand and the ability to deliver profitably.
Solopreneurs risk becoming isolated and losing perspective on life balance while grinding on business tasks. A peer network (his "campfire tribe" model) provides mentorship, shared experiences, accountability, and reminders to step back and prioritize what matters beyond just productivity - something he found through Flywheel coworking space in Concord, North Carolina.
Strategic vision is the desired outcome or impact (e.g., helping people increase their impact, or a personal trainer improving lives through fitness). Operational details are how you execute. Entrepreneurs who rigidly stick to one operational method miss opportunities the market is signaling; General Eisenhower's principle applies: planning is everything, but plans mean nothing if you can't adapt when reality unfolds.
Our reviewer’s read on each dimension, with quotes from the episode.
A handful of actionable points appear (start as a side gig first, 2-3 year runway, validate before quitting, referrals outperform ads) but they are buried under extended mutual affirmation and meandering storytelling. Most of the episode's runtime produces little new information for an experienced operator.
A lot of mistakes a business leader makes is they promote their best individual contributor into a leadership role. Skills that make you an outstanding individual contributor are not the same skills you need to get other people to do the work.
you're going to be in Q3 or Q4 of your third year before you have a profitable business
The episode leans almost entirely on recycled external anchors - Simon Sinek's Start With Why, Dave Ramsey, a Mark Cuban podcast quote, a Venn-diagram passion/skill/market framework that echoes ikigai/hedgehog concept - without adding a genuinely novel layer. The military metaphors ('enemy gets a vote') are mildly fresh in phrasing but not in substance.
In the army, we always used to joke, the enemy gets a vote. Well, the business world, your business environment, gets a vote.
What sits in the middle of those three circles, that's your business.
Tony Caldwell has genuine depth from 27 years of military service including ~11 years at the Pentagon, which gives him real practitioner credibility on leadership and org design. However, his consulting firm is less than two years old with no demonstrated business success at scale, and he explicitly acknowledges still finding product-market fit, limiting his authority as an entrepreneurship advisor.
I spent 27 years in the United States Army... stayed in the Pentagon for about almost 11 years doing a lot of different jobs.
I launched this business with the idea of I was going to support merging talent, the people that are first time leaders, first time managers. Because that is such a rough transition.
There are some named anchors - Jason Riccardi's specific net-negative first-two-years trajectory, the Flywheel co-working space, the 6-month salary savings benchmark - that give the episode modest evidential texture. However, there are no named client outcomes, no revenue data, and no external market evidence; the specificity is almost entirely autobiographical anecdote.
shout out to Jason Riccardi for telling me this. He's like, tony, my first year in business, I was net negative all M year... you're going to be in Q3 or Q4 of your third year before you have a profitable business
if you don't have six months salary, six months of what I make today. If you don't have six months of that in the bank, you really need to stop and think
The host rarely asks a tight follow-up; questions are frequently multi-part, self-answering, or pivot to the host's own story before the guest finishes. There is no moment of productive challenge or disagreement throughout the episode, and affirmations ('correct, correct, correct,' 'right, right') dominate the listener experience.
So welcome, welcome, welcome. Today I am, um, with Tony Caldwell from the 2326 group. So welcome to the Book of Balance podcast. I am so excited to have you here. So if you could please tell our audience who you are and how you came to do what you do today
And that's what I love about small business ownership. Because the pivots is what. That's what I asked you, like what cost the pivots?
Computed from the transcript - who did the talking, and the words that came up most.
Discover how to make a successful career transition from military service to entrepreneurship in this comprehensive guide featuring Tony Caldwell, a former US Army officer with 27 years of experience who built a thriving executive coaching and consulting business. Learn proven strategies for leveraging your military skills in the civilian business world and avoid common pitfalls that cause 50% of small businesses to fail. In this episode, you'll learn how to identify and monetize your transferable military skills, pivot your business model when market conditions change, and build a sustainable consulting practice from the ground up. Tony shares his real-world experience transitioning from the Pentagon to corporate America and eventually launching his own firm, providing actionable insights for veterans and career-changers alike. Key topics include how to create a strategic vision while remaining adaptable, the importance of storytelling in business development, and proven networking strategies for solopreneurs.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Hey, friends, it's Patricia Olegi from the Book of Balance podcast. And before we dive into today's episode, I want to remind you to grab your free copy of my CEO Money Map. It's a simple five minute ritual that helps you stay profitable and calm, even if you're not a numbers person. This guide walks you through how to check your cash flow, review your week, and make confident decisions all in just five minutes is the perfect reset for any business owner who wants to feel clear and in control. You can find the link to download your free CEO Money Map right in the show notes. Don't skip it. It might just become your favorite weekly ritual. And, uh, now let's get into the episode. Welcome to the Book of Balance podcast, where real stories meet real numbers. I'm, um, your host, Patricia Olegi, your bookkeeper and believer that business should serve your life and not consume it. Each week we sit down with entrepreneurs who've built their dreams from scratch and learn to balance their books, their boundaries, and their energy along the way. Ready to turn the page on financial stress and write your own story of clarity? Let's dive in. So welcome, welcome, welcome. Today I am, um, with Tony Caldwell from the 2326 group. So welcome to the Book of Balance podcast. I am so excited to have you here. So if you could please tell our audience who you are and how you came to do what you do today for other, uh, small businesses.
Speaker B: Oh, wow. Thanks, Patricia. First off, super happy to be here today. You're not connected recently and I got really excited about this opportunity. So who I am, look, it's a long story. By the time you get this much gray in your beard, who you are is a long story. Right. We'll try to keep it short and simple. Fairly much. Uh, for today, I am an executive advisor and storyteller. And what that means is I like to coach executives. I work with a lot of people. I always say that, uh, are becoming the C suite mid managers, people on their way up to be in the C suite that sometimes need a little gasoline poured on their, on the fire of their career. Public speaker, storyteller. Right. Work with a lot of entrepreneurs and solopreneurs. And I enjoy that space because I, I am one as well. Same as you. Right. Um, and that's always been fun for me. I spent 27 years in the United States Army.
Speaker A: Wow.
Speaker B: I started as an enlisted soldier. I went to Officers Candidate School. Didn't want to, but I was told to and then decided it was going to work out for me. Became an officer did a lot of work with combat units, artillery units, armor units out in the field. Early in my career, the halfway point, I got lucky enough to go to the Pentagon and most people go to the Pentagon for one tour, maybe two, and then they try to get back out into the field. I found that it was a good fit for me at that time and stayed in the Pentagon for about almost 11 years doing a lot of different jobs. And that's a whole two day long podcast, uh, the stuff we did then. But retired from the army in 2015, took a job like so many of us in D.C. do. We retire from the military and we take a job back with the military. I became a contractor at one of the school houses, teaching people to do organizational design the Army's way, which is what I did when I worked in the pentagon. Then in 2017 we had an opportunity to move to North Carolina. So my wife and I packed our son up and he's the last of our five kids. We packed him up and we came down here. He finished high school in North Carolina. We both started new careers basically from scratch. Uh, we didn't have a network of people. Spent a lot of time on indeed and other job boards and whatnot. Finding those jobs. Uh, oh, I had a lot of fun doing that. Took a job at one bank and was there for a while doing a variety of tasks and different assignments. Left to go to another bank. Spent a couple of years there. Went over to take a job with my last corporate job and I knew going in it was going to be my last. I knew I'd had enough. But this job sounded fun. Patricia they were about the halfway point of an acquisition and I came over to help with the uh, org design and development and effectiveness piece of the acquisition, how to put two strong groups together. That job sounded really exciting. I thought this would be a great final job for me. And was there a few months the acquisition, they came out and said, look, the acquisition has gone as far as it can. We're not going to finish it. And at that point I was like, the people I work with but don't really like the work they want me to do from now on. So let's build an exit strategy to get out of this and uh, let's find the next thing. And that's really what led me to forming my own consulting firm. I've worked a lot with a lot of people in different levels of leadership. Um, 27 years in the Army, I've seen and done a lot of. I found that that Experience translated well to corporate America. So a plug out there. Anybody that's tuned into your podcast. Patricia, if you've got the chance to hire a veteran, I would say hire them, tell them what you want done and then leave them alone and they're going to get it done for you. And you'll be really surprised. Those skills translate really well.
Speaker A: Yes. Yes.
Speaker B: So now I'm out on my own helping small business solo entrepreneurs and individuals that are trying to get to the C suite. The whole storyteller part is the part of my life where I do public speaking, lunch and learns those kind of things, sit in on other people's podcasts and occupy their time and be a guest for them. So it's been a lot of fun the last year is I think one of the things we want to talk about today is how people pivot in their entrepreneurship.
Speaker A: Yes.
Speaker B: And boy, I have taken over the last couple of years, I've taken a lot of left hand turns that I did not expect to take. So love that.
Speaker A: Based on, so based on, uh, once you decide to be a consultant, you took pivots because of the feedback you were getting or what were what constitute personal things in your life that helped that purge you to pivot in a different direction. What would you say that was the trigger point for those pivots?
Speaker B: Patricia? It's a really good question. As far as personal life, my wife and I are now empty nesters. So we've taken all the kids off the payroll, but we still act as advisors and senior board chair.
Speaker A: I love that. I love that.
Speaker B: And look, as anybody that's ever been on a board can tell you, they will tell the CEO what they think is needed and then they watch the CEO do something else. It's the same thing. But I will tell you that the thing that caused me to pivot in the business is in my mind I had a clear idea of, uh, what I wanted to do. What I found out early is that the market didn't want to pay me for the thing I wanted to do. I launched this business with the idea of I was going to support merging talent, the people that are first time leaders, first time managers. Because that is such a rough transition. And if I can take us down a rabbit hole for a second. Patricia, a lot of mistakes a business leader makes is they promote their best individual contributor into a leadership role. Skills that make you an outstanding individual contributor are not the same skills you need.
Speaker A: Correct.
Speaker B: To get other people to do the work.
Speaker A: Correct.
Speaker B: And that's a big gap. You talk to business leaders, they smile and nod their head the way you did. But there's not a huge market that people will pay someone else to come in and help that new leader. That's businesses try to do that internally and with varying degrees of success. And when it doesn't work, that new leader moves on to something else, they do it again and they keep making the same mistake and the business suffers.
Speaker A: Correct.
Speaker B: So that was the first pivot as I got more entrenched in working with people that their career just needs some gasoline put on it. That led me to a pivot of working with more entrepreneurs and my own business. Not working early has given me some lessons I can help entrepreneurs with. Right m and I can save them some pain. Maybe, um, sometimes we do, sometimes we don't. Another pivot my business has taken in the last few months. As I talk to people, they're like they started asking, could I come talk to people like you about some of the ideas I've shared with them, which has led me to do a couple of very low key casual lunch and learns. And that led me to doing to some facilitation work for other groups. It's been the conversation of Tony, I've learned a lot from you around how to give better feedback and how to do better performance reviews for my team and get more results. Could you come and talk to this. I'm just throwing names out here. Could you come and talk to this Kiwanis group or this Rotary group which has led me into the public speaking space.
Speaker A: Correct. I see.
Speaker B: Which two years ago I would have told you I don't want to do that.
Speaker A: Right. And that's what I love about small business ownership. Because the pivots is what. That's what I asked you, like what cost the pivots? Because the more I talk to business owners on their stories and I think if there's anything I like to share. I'm curious to know what your opinion on this since you advise small, uh, business owners as well. But what I'm picking up is that sometimes we have a lot of people who want to jump into business ownership and want to become entrepreneurs, but they're sometimes stuck on the idea of how to run that business and what they want to do far too long. And then once you jump in, like you said, you realize that what you the idea you had is not necessarily going to work the way you thought it was going to work. And for you, the transition was at the right time. But some people wait too long to make the transition and not until you go and start working. Do you realize what the pivots are? Because you didn't think about public speaking or becoming a storyteller until after the fact that you were in consulting. And that kind of came out of a result of the work. And you discover yourself in that arena. And I always think that is such an important piece that entrepreneurs need to keep with them, always be open to grow with the company and pivot as the company requires it or needs it.
Speaker B: For me, I think as a business owner entrepreneur, you need to have a strong vision of what you want your business to be. But I think too many times entrepreneurs get stuck, like you said, on this idea of, uh, I'm going to have a. The world's greatest fro and yogurt store and I've got this great recipe and if I just open my store, all these people will come and they. In the army, we always used to joke, the enemy gets a vote. Well, the business world, your business environment, gets a vote. And I don't care how good your frozen yogurt is, if you open up your shop in the wrong location, people just aren't going to come. If you offer two flavors and those aren't flavors that people want, they're not coming. Right. I do think an entrepreneur needs to have a strong vision of what they want to achieve, but I think that vision needs to be a strategic vision. If you look at my website, our motto is impact driven and values based.
Speaker A: Yes.
Speaker B: My goal, my strategic goal for a business is to have a business that helps people increase their impact, whatever that looks like. You, as a podcaster, how do you increase your impact? My client is a different type of business owner. They're a personal. And I'm trying really hard here to give examples without giving names, so I apologize.
Speaker A: That's right.
Speaker B: But I have a client that does personal training and his goal is to improve people's lives through personal training and get more fit. Well, that's a really good strategic goal. But if he were to get tied down in the details of, uh, I'm only going to do it this way because I've decided this is best. He's not going to get to the strategic goal. You, as a podcaster, you may say, I want my goal to have, uh, my podcast be in the top 25 of Spotify. That's a great strategic goal, Patricia. But how do we find a niche? How's the market telling you to. They want to get you there. Right. So I always talk to people about being agile, being flexible. You've Called it a pivot. I talk about being able to adapt to the situation. Everything depends on the situation. I can be really mad at one kid and turn around and be very supportive of another kid because of those two situations. What's going on? Right. I, I think to your point, the pivots have come for me. I'm going to be really honest here and say I probably pivoted a little bit late on a couple of things and that caused me to miss some opportunities because I was too stuck in. This is my ideal client. And as a small business owner yourself, you have an ideal client, right. That icp, the ideal client profile. This is who we market to. This sometimes our ideal client doesn't want us.
Speaker A: Right, That's a good point.
Speaker B: And we need to figure out who the real ideal client is. And for me, I think I personally, uh, I hung on too long. I had this conversation with a lady the other day that I listened better, sooner. I would probably be six months further down the road than I am today. I would have made more progress, but I got too entrenched, um, in my perfect idea.
Speaker A: Right. That's the issue when we're small business owners, that sometimes we get into this idea, the, like you said, the vision, your goal and, and sometimes it's hard to pull back to then look at the other angles and perspectives. Those. I think that's, that's one, if anything, I find that's one of the greatest things about business, owning your own business. It gives you an opportunity to learn something about yourself that when you work for another person, you just have to report to that person. But when it's your business, it forces you to do a lot of self reflection. And what you have mentioned that, ah, you are now a storyteller and I think this is why the podcasting world is so popular, is because we all love stories and we all learn through stories. And if you think about it, prior to a formal education, the way we got information down through generations was truly through storytelling because there was no written language for many decades. Right. And um, even today we continue to enjoy the story and um, the message behind it to continue to push forward progress and motivation. And this is the other end. But gossip is the other end of storytelling and we all love gossip. Exactly. So my, that's, that's to my point that the storytelling is ingrained in us as human beings as a way of learning and connecting with, with society in general.
Speaker B: Right.
Speaker A: So I think it's an incredible tool that we have to connect with other business owners as we Share stories that happen to us or to other cl. To make them a tangible, to make a story or a situation tangible and, uh, relatable for others to learn as we continue to grow and evolve as leaders and in our own businesses. So I think that storytelling is almost like. You cannot have mentorship without storytelling to a certain degree. That's my belief.
Speaker B: Well, Patricia, talking about something you said resonated with me when you talked about people used to learn by stories. Right. We have this kind of picture in our head of our ancestors, wherever, whatever your ancestor looks like in your head, sitting around the campfires.
Speaker A: Right.
Speaker B: And having these oral traditions passed down. Right. And that is where the real human connection is. Is a piece of advice that. And you just brought up mentorship. And a lot of people think of that in a very formal way, especially people that have spent a long time in corporate America. I spent 27 years in the Army. We always had mentors helping us. We always had that person we could just pick the phone up and call. When you're an, uh, entrepreneur, and even more so as a solopreneur, and this is not a pitch, hey, everybody needs to hire a coach, but everybody needs their entrepreneurial network that is beyond, hey, Patricia, this is what I do. Can you hire me? That's very transactional. We all need this network of people around us. And I use a co working space in Concord, North Carolina, shout out to Flywheel, because that's where I found a lot of, um, my network and mentors. And being a mentor doesn't, it doesn't mean they're older than you or they're in your same business or anything else. It just means they have experiences they can share and that they're willing to share. So I would encourage anybody listening to the podcast, find a group of people that you can share experiences with and sit at the campfire with and listen to. I have learned so much in the last 18 to 24 months, Patricia, of, um, talking to people that are fractional CFOs, fractional HR, all these entrepreneurs that I don't have a business, that it's like our business models don't fit each other. But to hear what they did in marketing or to share with them some of my leadership experience and just interact that campfire. I think especially as a solopreneur, we get so head down. Right, right. We so locked in and so focused. We're so on the keyboard. Uh, I need LinkedIn posts, I need social media posts, all this. But our, uh, the people around our campfire, we need to pull back and learn from them and talk to them and hear their stories, their oral traditions.
Speaker A: Right?
Speaker B: And they go, maybe it's not that important that I have something completely fresh on Instagram this week.
Speaker A: Right, Good point.
Speaker B: Uh, maybe it's. I talked to a lot of my clients. You only have so much time. And if you're an entrepreneur, you're a small business owner. It's something that my friends in corporate America go, oh, man, you work for yourself. You can give yourself pto, you can take off when you want. You know what, dude? I'm probably working more hours now than I've ever have in my life and love it more. But there are times that you've got to have somebody help you pull back and go, Tony, you've got 24 hours a day. You have to sleep sometime, you have to eat sometime. You have to be with your wife and your kids and your grandkids. How do you focus your energy? How do you stay focused on this is the important thing. And that's what that campfire tribe around you can help you with.
Speaker A: Uh, that's very true.
Speaker B: And sorry, I ramble.
Speaker A: That's okay. But that's good to have a strategic plan, but in the end, what good is it if you're not connected to the community or if it's not people are not resonating to it?
Speaker B: And look, your plans are going to Eisenhower. General Eisenhower became president, used to say, planning is everything, but plans mean nothing. Meaning you've got to always think about. You always have to know where you're going. You always have to have a way to get there. But your plan's not going to work.
Speaker A: Exactly. Doesn't mean it's, it's. They're not fault proof.
Speaker B: Right. And, um, we learn more from our mistakes than we ever have from us, our successes. You asked me how I got here. I can't tell you how I got here. I can tell you every mistake I've made since I was 10 years old.
Speaker A: Well, that's how you got here, right?
Speaker B: Right. Well, I guess, maybe, but you know what I'm saying.
Speaker A: If you think, if you think about it, we are a product of our previous mistakes. And based on whatever we did or points, it's all about how we as people interpret those situations, on how we decide to move forward after that. Because every pivotal point, which is usually based on something difficult or painful or tragic, we have two choices. We can either go on one route or the other. And we keep building our life on one direction or the other based on every Turbulent moment we may have in our lives that we don't think about, but we are. Uh, so we're here based on the. Whatever we have done or haven't done.
Speaker B: You.
Speaker A: Right. That led us to today. So. But I'm glad that you're sharing your story about how you knew that that was going to be your last job and you knew that the next thing was going to be something for yourself. Right. And so right now, what is something that you feel that since you started your consulting firm and you've gotten to know different people in different arenas where. What is your goal right now? Uh, as you continue to help small business owners, what is your. And I don't know if goal is the right word, but where do you see yourself being able to support small business owners? Do you want to do more public speaking? Do you want to. Do you think you're able to make the biggest impact through that aspect? Because that's the other thing. If we work one on one, you are making an impact on that person. But if we have the opportunity to do more public speaking or group speaking, then we might be able to have an impact of an. On a larger group.
Speaker B: I think that's really deep question.
Speaker A: Sorry, my brain works.
Speaker B: No, no, I'm with you. I always tell people I'm a fourth and fifth order thinker. Uh, if I'm buying lunch, I'm probably got two decisions based of my buying lunch today, based on that one. Right. And that's something the army taught me and going to the Pentagon and learning to move from making today's decisions based on what I need today to thinking about what I'm making a decision today that won't show up for three to five years. I'm making decisions about the future though, and that sounds too grandiose. I was making decisions about what the parts of the army would look like in three, five, seven years. Right. So be able to switch that mindset. I think for me, that way of thinking comes into my coaching practice and comes into my consulting work with small business owners to help them learn to lift their head up and look at the horizon.
Speaker A: Yes.
Speaker B: We all came into our business because it is a passion for us. Uh, passion doesn't equate to profit every time.
Speaker A: Yes, very true, very true.
Speaker B: Right. I talked to a lot of small business owners about there needs to be three circles, like a Venn diagram. What do I, what am I good at doing? What do I enjoy doing? And what will people pay me to do? And whatever sits. And whatever sits in the middle of Those three circles, that's your business. I enjoy woodworking. I'm good at woodworking. Nobody is going to pay me to build picture frames and headboards.
Speaker A: Right.
Speaker B: And a rate that I can pay my mortgage, I can sell a little of it. Right? And so that's the point with a business owner. I like to help them be able to lift their heads up and go, I know where there's a pain point. I know I can solve the pain. I know there are people that will pay me to solve the pain. How do I find them? What do I do to get there? How do I build a business around that? That is more than just my passion for solving that pain. And I think that's where a lot of entrepreneurs stumble. And look. Let's admit it, Patricia. Everybody listening to this podcast knows the vast majority of entrepreneurs fail the first time, second, third, fourth times. Right. I may well fail at this business. I look at how I. The goal of my business is to help people increase their impact in their lane. Is that being a better middle manager? Is that better C suite or just below the C suite in a corporation? That's what I want to help you do. If that's your goal, if your goal is to get your small business up and running, um, that's my goal. My goal is to improve my clients.
Speaker A: Right.
Speaker B: Their outcomes. This is not about Tony.
Speaker A: You said something that you said. It's like, we may all. And I think if there's anything that any small business owner can tell you, an entrepreneurial person, we have all done more than one business at one point. I owned a gym at one point. And yes, I lost money on that gym. It wasn't a whole lot in the big scheme of things, it's not a lot. A lot of money for me. But if you look at other businesses, it wasn't a lot, but it. It gave me a. I learned a lot. And actually it gave me the energy to even make a tough decision, which was to get a divorce and move forward. And one of the decisions was, this is not as profitable as I thought. I gotta kill this business and move on to the other business that I know is extremely profitable for me because now this can no longer be a hobby. I need to feed my family. But if anything, I think that's the spirit of an entrepreneurial person. They're going to try different opportunities until one works and the previous opportunities prepare you for the next opportunity.
Speaker B: Right. All of our choices have consequences.
Speaker A: Correct.
Speaker B: How we live with the consequences is huge. We would not be where we are. You And I joked a minute ago, I don't know how I got here. And you're like, well, of course you do. Well, no, I don't. Uh, in total transparency, some days I really don't know how I got here. But it's everything I did before got me here.
Speaker A: Right.
Speaker B: In one different decision. Any long, anywhere along the way and I wouldn't be exactly where I am. Right. I was very candid. Said I waited too long to pivot my business in terms of profit. I left a lot of money on the table. In terms of me being a better businessman, that experience was invaluable.
Speaker A: Correct.
Speaker B: Because now I have a better idea not only of who my ideal client is, but what they need, what I could deliver and the best way to deliver it. So when you ask us the best way to go because you ask the question, is one on one or groups better? In my opinion, you have more of an impact in a one on one environment. As a, as a. If I put on my pure coaching hat, I will tell you, for pure coaching, one on one delivers better results than coaching a small group or coaching a team.
Speaker A: And why would you say that? That's something that you see, but that's
Speaker B: built on the outcomes of individuals. Because if you and I are in a one on one coaching session, you can be much more open.
Speaker A: Correct. Very true.
Speaker B: Than when you're in a group of seven or eight people, whether you know them or not.
Speaker A: Let's pause for a quick moment. I've got some exciting news to share before we dive back into this episode. If you are ready to get more clarity around your business finances, I'd love to invite you to join my Clarity Compass method monthly bookkeeping membership. Inside you'll get the support tools and, um, guidance you need to stay organized by understand your numbers and make smart financial decisions while managing your own bookkeeping yourself. And if you're at the point where you're ready to fully delegate, we also offer white glove services. My team takes care of everything so you can focus on growing your business. To learn more, head over to www.claritycompassllc.com or find the link in today's episode notes and. All right, now let's get back to the show.
Speaker B: You're going to hold back. The public speaking is a good tool for me as a coach to expose more people to me and to the way I coach people because I don't have this canned approach to coaching. Patricia is going to be different than Susie. It's going to be different than Sally. I want to Treat all of you differently. We're going to take different approaches. My public speaking exposes people to the idea that, hey, Tony's pretty good at this. Tony's got this track record from the military and the civilian life of helping other people achieve their goals. Almost everyone that worked for the military, worked for me in the military, went on to have a better career than I did. One of the core values, you know, we call them army values. Right. Is selfless service. We always put other people and their success and the mission ahead of our personal needs. And that's what I bring as a coach, is like, I'm not here to tell you what to do, Patricia. I'm here to help you figure out the right way for you to do it.
Speaker A: Correct. Correct.
Speaker B: And we're all different. I will tell you that my greatest goal or, uh, my biggest joy from this was having a client that I was working with about situations, go through with the job, come back to me and go, tony, I'm good. The situation has solved itself. We were. I used what we were talking about. It's working for me. And I've gotten a boost at work. Uh, I want to cancel our contract for the last two sessions. I'm good now. I got. That brought me more joy.
Speaker A: Right?
Speaker B: Signing three new clients that week.
Speaker A: That's so. That is so true. That is very rewarding.
Speaker B: So that's a long way to tell you that. My impact is.
Speaker A: Starts with a larger group, but then hopefully you'll be able to meet people that can actually go in deeper with them.
Speaker B: Um, for me, my goal. You ask about my goal. My goal is to see you get better.
Speaker A: And so let's say I'm just. I'm now. Now I'm like, super curious. So now I'm like, so now the audience has listened to you, like, oh, this is cool. I want to get better too. Uh, if I. You and I were. We sat down, we agree, we're going to work together, we're going to collaborate. You're going to help me see the things that I'm struggling to see, and we're going to create this plan, what that will look like. And I know it will look different for every person based on their needs, on their situation, etc. Etc. But what would you say will like a system or a platform or a pattern that you try to follow. That way you can help people go from A to Z, and then they tell you, I don't need you anymore. Thank you. Let's cancel the contract.
Speaker B: First thing is me and the person I'M working with the prospective client.
Speaker A: Correct.
Speaker B: We have to be able to communicate well and we have to have. Be able to trust each other. I, uh, often tell people that working with me is going to a confessional, what you say to me. And that's the reason I was struggling earlier to give you examples without revealing who I'm talking to. Right, right. What you say with me stays with me. It doesn't go anywhere else. I don't publish a lot of success stories on LinkedIn because I don't want to reveal that. Tony, Patricia work together, and Patricia got this result. Right. So the first thing is we have to have a real. We have to be. You have to have a problem that I can help with. And if you can't. If I can't, I'm going to tell you that. Second thing is we have to be able to trust each other and work together. We have to communicate well. If we've got that, then when we enter into a contract and an agreement, you and I will decide up front we need to talk. Typically every other week for either six or eight sessions. That's kind of the base because it takes two, sometimes three to really dig in and surface what's underneath. I always talk about. My English teacher at high school said every good piece of literature is really two stories. It's the story that you read, and then underneath it's the story that the writer's telling you. And so it takes us a minute to get past what we're reading and into what you're saying. So typically six to eight sessions, about an hour or so every other week. It's a real. The format's fairly standard. We start with, hey, Patricia, you know, a little bit of how you've been doing, you know, the chit chat. Right. And then, Patricia, what do you want to work on today? And you'll come out with, Tony, I want to do this. I got this issue. I got that issue. You'll surface two or three things between the two of us, we'll decide which is most important. And I'll say something along the lines of, hey, Patricia, you said you really want to work on being able to meet deadlines, but you're having a problem meeting deadlines at the end of this session of what would you like to have towards that? This is very client driven.
Speaker A: Bye.
Speaker B: The client, the client drives. I just help navigate. I read old maps that we used to unfold. I help you. I help you see the map. You'll say, well, Tony, I'd really like to be able to Hit deadlines better. So how are we going to do that? And we will talk through obstacles for you hitting the deadlines, what you see is impacting you, what we can change for you. And by the end of that session, the beautiful thing about this, Patricia, is I'm not going to tell you anything.
Speaker A: Right? Right. You're going to. You're going to realize it yourself.
Speaker B: Right. You will be able to say, hey, Tony, I think I want to try this. I'm going to do some time blocking on my calendar. If my deadline's on Friday, I'm going to put on my calendar that my deadline's Thursday or Wednesday, so that I have more urgency around it. And we're going to come up with a little bit of a plan for that, and we're going to talk about how you're going to hold yourself accountable, and we're going to talk about how you're going to hold yourself accountable, how you're going to practice that for the next couple of weeks until the next meeting, and then when we get together again, we're going to have that discussion. How did that go? What worked? What didn't? Or you may come into the next one and go, hey, the deadlines are getting better. I've got this other thing.
Speaker A: So my question is, have you had people that come in with an idea what they want to work on, and once you start digging in, you realize there might be something else that is
Speaker B: actually impeding them from every single time. Patricia.
Speaker A: So that's, uh. That's, I think, the biggest piece. Giving ourselves permission and the time and the willingness to block that time with you, to quiet the mind, to then try to understand why we're at the situation. Because I think that's the biggest thing. We're always on the go, go, go, go, that we don't stop to think, why am I not meeting the deadlines? What's. And there might be four other things that have nothing to do with deadlines that could be blocking you, but you haven't stopped to really even take a deep breath, to really realize what is blocking you or whatever that might be.
Speaker B: And a good coach will help you do that. And having the dedicated time. And like you said, it goes back to what my English teacher said, right. There's the story that you're reading, and then the story that they're really telling you and that you just described it, Clients come in, they go, I have this problem with my co worker, blah, blah, blah. Or I'm, um, meeting, having a problem. Deadlines have problem with boss My career stall, whatever it is. And that's where he said, patricia, it normally takes two or three. Somewhere in that third session for sure, is where Patricia would say, tony, it's really not the deadlines, is it? And I'll go, well, tell me what you think it is. Patricia would say, it's not the deadlines. It's I'm not doing what I'm built to do.
Speaker A: Oh, you don't like what you're working? Exactly.
Speaker B: I'm just a deeper sense of purpose. I'm doing a job that I am just not built to do. I can do it. It's fine, not a big deal. But I'm not built for this. I'm built to do something else. I think our, uh, divine creator built all of us to do something, and
Speaker A: that's important and so empowering. I think all of us are just going through the day to day, and we don't really take the time to think about our purpose. And not until we set the time to sit and talk about it and process what we're actually doing can we really make bigger decisions that are going to continue to help us to grow. Right.
Speaker B: The whole thing, everything gets back to what's. Simon Sinek wrote a book called Start With. Start With. Why? Why do you do that? Why is this our business? And I won't deep dive into that book. Your listeners can pull it up and read it. It's a great book. It's been out about 10, 15, about 15 years now, I think. But a lot of us experience turbulence in our life when we're not doing the thing that we're built to do. And that doesn't mean that you have to have this huge burning passion to paint murals on the ceilings of buildings or whatever it is. Right. But a lot of our internal conflict is just when we're doing things that are not aligned with who we are. In the small business owner, entrepreneur space, you've probably gotten through that, and that's the reason you're out on your own doing your own business. I knew I wasn't going to stay in financial industries because that was not what I was built to do. I knew I was built to coach people and be their partner in their progress. I knew I needed to shift to that. I think where a lot of entrepreneurs make the mistake is they go, this is my passion. I'm just going to jump out and start. And it's very much field of dreams. If I build it, they will come.
Speaker A: Right, right, right.
Speaker B: That is not true. As you learned with the gym as I've learned with my business, just because you build it doesn't mean people show up. Right? Right.
Speaker A: There's also trends and that, uh, we need to learn in society what works and what's the hype and what isn't.
Speaker B: Right. And there's a lot of great restaurants that didn't stay in open for a year.
Speaker A: Right.
Speaker B: Great food, but it wasn't the right business model or whatever. Right. So I think as an entrepreneur, what I would tell everybody, I always tell people to start messy.
Speaker A: Yes. 100%.
Speaker B: You don't have to be perfect. If you're waiting to be perfect, you've probably. You're going to miss it.
Speaker A: Right.
Speaker B: I was too set on, uh, my business being one thing. I missed a lot of opportunity when people were telling me, you should do something else because I was stubborn. Now I have a great wife. She's an amazing woman. She helped me break that down. Love Laura to death. She's absolute best wife I could have had ever. And I had one before, so. I know. But too many of us don't listen to that feedback and too many of us don't see the environment. As an entrepreneur, you've got to be flexible to the feedback.
Speaker A: Yes, yes, yes.
Speaker B: And your cash register is your feedback. Right. But you have more feedback than that as well. All I would tell your entrepreneurs and small business owners, have a vision for what you want. Be passionate about getting there, but understand it's not a straight line.
Speaker A: Correct. 100%.
Speaker B: So start messy.
Speaker A: Uh, you need to start, just start,
Speaker B: start it as a side gig. I started coaching and consulting honestly for free on the side just to make sure I was good at it, to see if people wanted it.
Speaker A: Right.
Speaker B: That encouraged me. I got good feedback that encouraged me to go do it.
Speaker A: Right.
Speaker B: The other piece is to have your finances in order. Can we just be real candid here for a second, Patricia? A lot of people put too much, don't financially prepare to be an entrepreneur.
Speaker A: Very true, very true.
Speaker B: You are not going to step. If you're making six figures a year at, uh, you and I are in Charlotte. A lot of bank jobs. Right. You're making six figures a year at a big bank. Don't think you're going to start your basket weaving business and make six figures
Speaker A: this year for sure. I think you plan to have at least. Well, for my businesses that I've created, I have always given myself a plan of two to three years before I can get the number that I think I want to get. And because of what, and, and that's exactly what I was planning to do with. I decided to go into bookkeeping, so would have flexibility to work remotely. Um, then things happen that compress my timeline. So I left me at, well, it's going to take me two to three years. Even if I compress and all these other sources of income disappear, it's still going to take me two to three years. I'm like, I am in for the long haul. So structure things and plan around, but you need to be aware that you're not going to be at the number that usually that business can yield until two to three years into it.
Speaker B: When I first launched my coaching business, one of my mentors is a really respected coach. He's got tens of thousands of hours of coaching and shout out to Jason Riccardi for telling me this. He's like, tony, my first year in business, I was net negative all M year.
Speaker A: Yes.
Speaker B: My second year of business, I had a couple of months where almost paid the bills, but the whole year was net negative. He's like, you're going to be in Q3 or Q4 of your third year before you have a profitable business. And that was a real bucket of ice water in my face that made me step back and go, you know what? I'm not going to leave corporate America just yet. I need six more. I, uh, sat down and I need six more months to get my house in order before I leave.
Speaker A: Exactly.
Speaker B: And did I want to do that? No. But that was the first pivot. The first, the first pivot, Patricia, was, I'm not going in next week and quitting. I need six more months. I would tell anybody. And I heard Mark Cuban say this on a podcast a long time ago, if you're getting ready to start your own thing, if you don't have six months salary, six months of what I make today. If you don't have six months of that in the bank, you really need to stop and think.
Speaker A: Right.
Speaker B: I'm not going to tell anybody not to do it because, uh, your listeners are in all different phases of life. So I'm not. But do you have. I talked to a young man a couple of months ago that he's getting ready to retire from the military and he wants to go be a coach. And I was like, how much money do you have in the minute? How many months can you make it without a check? Marriage, got kids. He goes, we can get about two months. If we max the credit cards, we can get them maybe four. I'm like, dude, this isn't for you. And I told him what I just told you about and your listeners about two to three years. And he's like, Tony, I can't do that. I'm like, then you need to find a different job while you build this on the side.
Speaker A: Correct? It's not that you cannot do it. You just have to have a plan on how you're gonna support yourself while you get this off, uh, the ground. And, um, there might be some people that may not have the flexibility to stay, stay in their job because maybe their life has pushed them into me. So I think it's important for people to understand if you happen to find yourself in a situation in which life has put you in a opportunity that you. This is my chance to do my small business that I always wanted to do. I no longer have the job. So I either go back to the job, to another job, or I do this that I've been wanting to do all my life. I think you can do it, but you need to be very careful and be willing to, to go back to that spreadsheet and look like, do I really need that Netflix membership or do I really need that second car like, or, or can I look for ways on, reduce and minimize your budget so you can stretch your savings as far and as much as you can.
Speaker B: I like ramen. How much do I like ramen exactly? I really eat ramen all week and be okay with myself. Uh, not a healthy choice, but can I do it right? And look, I'm not saying you got to have 6 months salary before you move out. I'm just saying that's your mindset I've
Speaker A: got to figure out.
Speaker B: And I think too many entrepreneurs step into it thinking that they're going to have a great level of income, whatever that number is, it's different for everybody in 60 or 90 days. And some people do, some people are successful quickly. The majority of us are not. The majority of us. To your point, when you stepped out to do the bookkeeping, you knew it was two to three year path, right? And this is why.
Speaker A: And I, and I, and I sold everything, right? And I went and I moved to a property which I was able to pay outright, right? Be able to give myself the cushion of two years within a, um, budget that I could do while I grew the business, right?
Speaker B: And for me it.
Speaker A: But you have to make plans accordingly to give the, you have to give your business and yourself the chance to be successful. You don't want to go in and go halfway and then all of a sudden you're running out of steam, you run out of money and you quit halfway. And you'll never know if that business would have been successful or not.
Speaker B: Right. And Trisha, you talk about selling, selling things and downsizing and all that. We did the old Dave Ramsey thing.
Speaker A: Yes. I, I'm actually certified with Dave Ramsey.
Speaker B: Right. We had the book, we followed the
Speaker A: method, and actually it's right there.
Speaker B: There you go. I see only. The only solid, uh, the only debt we have is a house note. But we got to that. That's right. I said, hey, I need another six months. Right. Because I needed six more months. And I know Dave says, get the house paid off too, but we got to the point that my wife and I looked at each other go, we're comfortable now.
Speaker A: Exactly. There we go.
Speaker B: With Tony going out on his own with zero clients, no money coming in, knowing it's going to be a two to three year Runway.
Speaker A: Correct.
Speaker B: The debt is controlled, we have the savings. And look, I don't have two to three years of salary in the bank. Right. But the savings is enough.
Speaker A: Right.
Speaker B: We've got a path.
Speaker A: Right. Exactly.
Speaker B: And I think entrepreneurs, too many of us get so excited about our dream that we need that bucket of ice water.
Speaker A: Yes. Yes.
Speaker B: And I don't say the last few minutes sound like a bummer, and I apologize for your audience.
Speaker A: Uh, no, I think it's an important piece.
Speaker B: Your passion will pay you someday. Let me. The high school grade, high school graduation speech doesn't work in reality. But here's my other advice. Know what it's going to take to get you there. Have a plan for it and start doing something now.
Speaker A: Yes.
Speaker B: Start with your, with you, with bookkeeping. Bring in that first person that lets you do their books. Right. And do that for a couple of months as you work another job. Don't do anything illegal, uh, unethical, immoral.
Speaker A: Disclaimer.
Speaker B: Yeah, disclaimer. Don't sue Tony for that. But start something on your business. Tell people that you. Another great piece of advice is you farm the field closest to the barn.
Speaker A: Yes.
Speaker B: Tell everybody, hey, I'm Patricia. I'm going to start a bookkeeping business. I have one small client. I'd love to have another small client. No, I haven't quit my full time job. I'm just doing this for extra income. Tell everybody, everybody to understand what your goals are. Those people will bring money to you. Every client I've had. And sorry for you marketing people out there, none of my ads worked. None of that stuff worked for me. Every client I've Got in the last 24 months was a referral from somebody that knew what I was doing. That's where you start your business, your friends, your family will bring you people.
Speaker A: And I think that's very. I want to make sure that we get to the point which is share how people can reach to reach out to you. But I think we also have two different kinds of uh, pots here. I think for services 100 the referral and the knowing each other. It's extremely important for trust because people are going to be working for you. They need a service from you. Product based people who are actually trying to sell a product. I have learned that people have had to learn to rely on everybody but their family and friends to get off the ground. So I think um. But I've had a lot of people come through that have products that have said the opposite. But I do agree with you that in the field of providing services, especially financial coaching, anything personal which you really develop an intimate relationship with that client, you really people are going to trust and be able to feel more comfortable sharing more personal information with someone that is being referred to you versus someone that you just you uh, got an ad on.
Speaker B: I think, I think you're on to something there product is different than services. But even with product social proof, a term I learned last week where people say this product works in Google reviews, the Amazon reviews, 4 stars, 5 stars.
Speaker A: Very true, very true.
Speaker B: Still still have a lot of those are still referrals.
Speaker A: Good point.
Speaker B: And your family and friends can still say, hey, my brother Tony has this great widget. You should go buy his widget. Just because you have a product, your family and friends still need to be your hype man.
Speaker A: That's right.
Speaker B: But I do think you're right. I think products find their way into people through marketing in a different form than services do. I would never trust my books. This just me. I would never trust my books to somebody I saw online that says, hey, I do great book work, I do great bookkeeping. I would trust it more when somebody says Tony. I know Patricia, she's done really good for me.
Speaker A: Right.
Speaker B: So I think it takes a combination of both. And again folks, if you're listening, if you don't agree with us, that's awesome.
Speaker A: Please write it on the comments. Let us know. We can't wait to hear from you.
Speaker B: Yeah.
Speaker A: How can people get a hold of you?
Speaker B: People can get a hold to me simply there's a QR code over my shoulder.
Speaker A: Right.
Speaker B: You can scan that. That will take you to my webpage. Tony Caldwell on LinkedIn. Follow me there. I'm fairly consistent a couple of times a week there. Info@the2326group.com info@the2326group.Com and Patricia, put that down
Speaker A: in the comments yet, because we also have this on podcasts, which they will not have access to the QR code, but I will make sure that we actually put the website there for them. So, website, email, LinkedIn.
Speaker B: Right. Those are the best ways. Again, what you and I were just talking about in the coaching space. Social media is not great, right. So I don't do it, but. And that was another pivot. Tried it, didn't work. Understood it better. But folks, just look for me on LinkedIn. Tony Caldwell. I'm in Charlotte, North Carolina. There's only a couple of us on there. You can connect with me through there. Happy to trade messages there. Uh, emails and just follow the content.
Speaker A: Do you work remotely as well, or do you work only with people in Charlotte?
Speaker B: I. I will work with anybody that can do a Google Meet call.
Speaker A: Perfect.
Speaker B: Uh, the public speaking. I do that. I've done lunch and learn via Zoom. That's easy. The main thing is just connect with me and let's start a conversation and figure out if you have something I can help with and if I'm the guy that you trust enough to help you with it.
Speaker A: Excellent. Well, thank you, Tony. I, uh, really appreciate your time and telling your story. I appreciate. I could talk. I always say this at the end of every. So I could talk for hours. Because again, this is why I started the episode, because I can talk for hours. This is why I did the podcast. But thank you, Tony. We'll definitely make sure that all your information is in the notes of the show so people can find you on YouTube or in our podcast, which is on Apple, Amazon and Spotify, so people can find you. All of that. So excellent. Thank you so much, Tony. Uh, I hope you have a great rest of the day. This is a season. It will be aired in mid February. So have your ears peeled for that then. And, uh, for all my listeners, uh, stay clear, stay focused, and have a great rest of the day. Bye. Thank you for joining me for today's episode of the Book of Balance podcast. I hope you enjoyed our conversation and found, um, value in the insights we shared. Make sure you subscribe. Subscribe so you never miss a future episode. And as promised during the show, you'll also find a link in the description with today's guest information, website links, and all the mentions we talked about during the episode. And if you're a Do it Yourself entrepreneur, you can join the Clarity Compass method@claritycompass LLC.com it's a, um, monthly subscription where business owners like you dedicate just one hour each week to work in their books, get their questions answered, and stay consistent with their support of a community committed to financial clarity. Now, if you like to connect with me personally, head on to my website olegi.comm to schedule your complimentary 15 minute consultation. It's the perfect way to get your paper, personalized bookkeeping questions answered, and explore how the White Glove services can support your business. And on the last note, remember, we are not lawyers or financial advisors. Everything shared here reflects our professional opinions and is provided solely for educational purposes and entertainment purposes only. So thanks again for listening and until next time, keep your eyes Compass Sit on Clarity.
Other episodes covering the same guests and topics, from across The B2B Podcast Index.