The Psychology of Scaling: Inside Ian Leaman’s Playbook for Mid-Market Founders

August 06, 2025 00:32:15
The Psychology of Scaling: Inside Ian Leaman’s Playbook for Mid-Market Founders
The Victory Podcast with Travis Cody
The Psychology of Scaling: Inside Ian Leaman’s Playbook for Mid-Market Founders

Aug 06 2025 | 00:32:15

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Show Notes

In this episode, Rachel League interviews Ian Leaman, a seasoned business coach and fractional CFO, who shares insights on helping companies grow and successfully exit. They discuss the common challenges entrepreneurs face, the importance of understanding one's 'why', and the strategies that lead to successful business scaling. Ian emphasizes the significance of people in business, effective time management, and the integration of technology in consulting. He also shares his approach to onboarding clients and the personal satisfaction he derives from their success.

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Episode Transcript

[00:00:00] Speaker A: Foreign welcome to the Victory Show. [00:00:25] Speaker B: Hey victors. Welcome to this episode of the Victory Show. If this is the first time you're joining us, I'm Rachel League with Bestseller By Design. Our founder, Travis Cody is the bestselling author of 16 books and we've had the privilege of helping hundreds of business consultants, founders and entrepreneurs write and publish their own best selling books as well. Through that journey, we've discovered a fascinating pattern. Most businesses really struggle to break past the seven figure revenue mark. On this show, I sit down with some of the world's most successful CEOs, leaders and business owners to uncover the strategies they used to scale way past that mark so you can do the same. So get ready for some deep insights and actionable takeaways that you can implement in your life and business. Starting now. Today's guest is Ian Lehman, an accomplished board director, expert, fractional CFO and business coach whose career has been defined by helping over 100 companies unlock their full potential and achieve successful exits. A Chartered accountant and FINRA registered investment banker, Ian has held senior finance positions in the United States and internationally, earning US Permanent residency as a person of extraordinary ability recognized for sustained international acclaim. He's the co founder of Nexus Numerica where he is helping lead the transformation of the $262 billion US accounting market through strategic acquisitions, proprietary technology and operational innovation. Ian is also the Managing Director of Marula Capital, a mid market investment banking firm providing M and A advisory, fundraising and valuation services, and the founder of Duke and Lehman, a consulting practice advising companies on growth and exit strategies. Beyond his advisory work, Ian serves as a CFO and board member of multiple businesses, combining his skills as a steward, operator, strategist and catalyst to build and scale organizations. Ian, welcome to the show. [00:02:13] Speaker A: Thank you Rachel, Great to be with you. [00:02:15] Speaker B: You've dedicated your career to helping companies grow and exit successfully. What first sparked your passion for this business in the early days? [00:02:27] Speaker A: Well, I trained, as you mentioned, as a chartered accountant and conventionally that training involves being an audit clerk or doing technical tax work. I found myself very frustrated very early on in my career with those particular directions and managed to persuade the Senior partner of the restructuring and turnaround department at Deloitte to enable me to continue my training there. That put me at the sharp commercial end of the advisory services which accountants provide to businesses and got me into deal doing and the realization of capital from completed projects. So that's what really got me started. My journey continued through mid market M and A advisory, taking more than 100 businesses as you mentioned through the exit process and learning a whole lot on that trajectory about what makes businesses succeed and why they don't necessarily succeed in pursuing, pursuing that exit path. So I'm really stimulated working with mid market entrepreneurs who are ambitious to grow and then to exit their businesses. [00:03:37] Speaker B: It sounds like you get to work with a lot of really interesting people. Is it that part of the business? Is it more the technical side? I mean, what is it that really lights you up when you get to help someone scale an exit? [00:03:49] Speaker A: It's all about the people. The technical side is a given and I think if you're a great technician, you kind of reach a natural ceiling in your career in the world of exit advisory, what have you. For me, it's about the people. It always has been and always will be. I'm fascinated by people's journeys, by their experiences, by their aspirations, by their fears and the deep, deep psychology that, that play with entrepreneurs as they grow and then hopefully ultimately exit their businesses. It's fear and greed and a mixture of those two emotions in large part together with very, very specific circumstances. Sometimes there's, there's a sickness, either directly or in the family, which motivates an action. Sometimes there could be a breakup, a marital breakup which stimulates things. Other times there's a inherited a desire to do better than the previous generation or something like that. So there are very specific factors. But it's all, it's all about the people, Rachel. The technical stuff looks after itself, right? [00:04:50] Speaker B: Well, I suppose if you can do the technical well, then the secret sauce is in the people. Part of it really is. [00:04:56] Speaker A: It really is. [00:04:57] Speaker B: And this is such an interesting interview for us because not only have you built your own successful, highly scaled business, but you are also helping others scale and exit their businesses. And so in working with so many founders, what patterns have you noticed in the ones that ultimately did succeed in scaling and exiting their business? [00:05:16] Speaker A: Okay, so I'm going to focus now on in particular the coaching work I do, which is embraced by entrepreneurs who aspire to growth but are somewhat frustrated along that path. They typically have not empowered their senior people. They typically don't have clarity either in the short, medium or longer term as to what their goals are other than some vague aspiration. They want to build and realize value and typically don't have the toolbox and the techniques that can be really helpful in unlocking that. Typically these entrepreneurs would be people who have left perhaps a comfortable or paid job in the corporate world to live the entrepreneurial dream. But the reality, day to day for them is typically get in in the morning at 8 o', clock, start dealing with problems, continue in that mode for 12 hours, go home, rung out, dissatisfied, and then rinse and repeat again tomorrow. And unfortunately that cycle is one which is so prevalent amongst mid market entrepreneurs, particularly those with companies struggling to break through the kind of size level that you mentioned you're interested in. So what I do with them is the raw material firstly is an entrepreneur who really wants to achieve this growth, has the potential to do so, but is frustrated and is willing to be open to change. So that openness to change is one of the common factors there that you know, you asked to identify. They've got to be open minded, willing to change. Once we've got that, that's the raw material really. And I can work with that with these tools and techniques which take them on a journey partly of throwing a light on a big, big, big mission. Why? Why their organization exists not just to make money for them and their family, there's a bigger purpose than that. It's a purpose that transcends just making money, which is the result of the successful business. It's one which defines their role and how they can make a dent in their universe and the discovery of that, why that great big shining star up there is something that all that they and their senior team can rally around and can, that has longevity and really forms a great context for them and then work back from that to from the really macro there towards the micro delving right into the minutiae of the business. Challenging questions like are the right people doing the right jobs? How aligned are those people with your core values and how effective are they in doing their jobs? And you can make, as you can imagine from that description, you can make a grid and you can plot people on the grid. You can figure out who needs coaching up and who maybe is there already and where do you spend your time with the less effective ones or the more effective ones? Challenging questions like that. So those people that I've worked with who have been most successful along this entrepreneurial path have been ones with open minds, receptiveness to change, burning desire to grow and be successful and embrace the tools which can give them the clarity to help them really execute so much better than they do before. [00:08:24] Speaker B: When a potential client comes to you, are you, given that you have such volume, seeking out clients that already have that within them, are you helping to bring those attributes out or does that need to be a foundation from which you can then build to that? [00:08:39] Speaker A: Why, if we're Talking about the why. I think every organization, whether they're growth oriented or not, can, can spend some useful thinking time getting to their why, distilling various different alternatives. And the world's most successful businesses are ones which have developed that why and really, really stick to it and it can be there for the long term so that, that anyone can do. I think the businesses which I have most success with and become the most successful as measured by exit achievement are those which do go along this growth path because growth is something which acquirers ultimately covered and without that growth it's difficult to attract some entrepreneurs to be fair, have lifestyle businesses which they recognize them for what they are, they appreciate them for what they deliver to their family. And that's fine. Not everyone, not every business has to go on that growth path. But if you do, I coach some pretty good techniques which can demonstrably take your business on a path which grows 3x in 3 years. 5x in 5. [00:09:48] Speaker B: Incredible. And do you coach the openness mindset that allows you to get to that why or this if somebody comes to you pretty closed off in a way. What you're describing sounds to me like a just a business coach, but a life coach, maybe even a therapist of really breaking down pre existing ideas about how a business should be run and opening them up. Is that something that you do or is that something that they have to come ready to do the work? [00:10:16] Speaker A: No, I think there has to be a receptiveness and open mind to, to do that work. And I, you know, I encounter people from time to time who either take the view that what I'm, what I'm already doing is, is good. If they're growing and they're frustrated, they're not achieving, that's how they're doing it, that's their way. And so, and I don't try and persuade, to persuade them otherwise. I think I'm working with people who innately have that dissatisfaction and openness. That's the magic combination. [00:10:51] Speaker B: Was there a time that you had a client that you faced a bump in the road with? Whether that meant that eventually they became less open to change or you had trouble implementing some of the systems that you mentioned to actually get the execution going? When was a time that you really had to turn the key to unlock knock the next phase? [00:11:11] Speaker A: Yeah, those, those situations do come up from time to time. And you know, getting into a deep and trusted relationship with an entrepreneur is a challenging thing from both point of view, from the entrepreneur's point of view and my point of view and you know, you always start with great and aligned positive intentions. But the nature of life is that doesn't always work like that. They they some of the challenging issues we come up against, for example, would be one of the things I coach is to the, is to measure effectiveness and success in the journey by reference to objective measures. Typically those relate to sales growth, profitability and such like. And many entrepreneurs, particularly in America, are not open even with their most senior people about the financial results and effectiveness of their businesses. So they have to be willing to go along that journey and open the kimono somewhat to their senior people. And sometimes we just get stuck at that point. But they take a view, no, this is my business, I'm not going there with the team. And it's quite difficult to create objective measures without reference to those financial measures. Other times, you know, sometimes the very nub of success of entrepreneurs is their rigid has been their rigidity, inflexibility. They hit a formula that works and they won't flex from that. They're rigid. And that doesn't play too well when we're looking for flexibility and adoption of new techniques and tools. So that can be another cause of frustration. But most of the time there's great alignment and either the business simply goes along the growth path and increases its quality of earnings desirability to outside acquirers. The stays with the owner, which is absolutely fine. My view, if a business is exit ready, it's ready for every day. So that's where we aim, where we aim to get or we do pursue the path and we go through an exit. And you know, having taken more than 100 businesses through that process, I can really, really help them to prepare for the very, very challenging exercises as an exit is. It's unlike anything that most people will have experienced in the past in their businesses. You know, the strains of growing a business every day are just magnified with the strains of engaging with potential acquirers, going through the due diligence process, negotiating the commercial terms of the deal, etc. So you know, helping them along that path is something that I can do really, really well. And ultimately we end up in lockstep going, going together through this process and across the finish line. What happens after is afterwards is also very interesting. [00:13:55] Speaker B: Oh, do go on. [00:13:56] Speaker A: I will. Because you know, many entrepreneurs existence in the world is defined by their business. And if suddenly their ownership and leadership role within that business is taken away or transitioned even, you know, to a new owner with a continuing period of working for them, that sense of identity can be challenged. And can result in unhappiness, depression, distraction, all sorts of negative things that are really worth giving some thought about beforehand. So I do spend some time in that sort of pre exit counseling mode to ensure that the entrepreneur has an exit plan beyond having the bank account ready to receive the proceeds. [00:14:38] Speaker B: Right. Totally makes sense because so many entrepreneurs, their business becomes their life whether it's healthy or not. And I'm sure there is sort of an existential crisis that comes when such a huge part of their identity is no longer in their day to day. So how hands on, involved are you personally in this process? Tell me about what it looks like when you work with a business because I know that you have scaled this consulting business. So do you have other partners that help you as you think about what's a very time intensive operation? [00:15:11] Speaker A: Yeah, so somewhat constrained in scaling my business because of the need for very high touch, very personal, very involved relationship for myself with the client. So essentially 10 to 15 would be the maximum number of active clients I can really look after at one time. The frequency of touch points is generally monthly. A lot of what I'm doing in that time is monitoring progress against targets, helping with little course corrections along the way and then some really much more intensive quarterly and annually annual meetings to ensure on part on track for the year and looking back over the year and then forward for the next year. And planning scaling has certain constraints, certain things you can do in a consulting business to scale with virtual assistants and increasing the use of AI and, but nonetheless it's not a business that could have 500 clients one time. [00:16:14] Speaker B: Right. Have you started to consider incorporating some of those elements that you just mentioned to increase the scalability or are you really focused on just higher dollar value targets to keep it to that same 10 to 15? [00:16:28] Speaker A: Yeah, it's, it's. Each project is a, is a high dollar value. But in terms of ROI for the, the entrepreneur represents a massive multiple on their, on their annual spend. If you think about the 3x in 5 years. 5 years livex in Vive. [00:16:45] Speaker B: Yeah, right, right. And for your own personal consulting business, as you think about what the future of that looks like, are you incorporating AI, adding virtual assistants? How are you getting leverage for the next chapter of Summit os? [00:16:59] Speaker A: No, I, I'm, I'm all for creating efficiencies in my own business as I teach to others and yes, so incorporating AI in processes, back office Essential Pro, essentially processes. But there's no substituting the effectiveness of the one to one relationship with the, the owner, manager, entrepreneur and Their senior team in a room in an intensive eight hour session where so much gets achieved. [00:17:25] Speaker B: What are some of the things that you achieve in those eight hour sessions? [00:17:28] Speaker A: Well, it gives them the space to examine their business's place in the world, where it is now, what its challenges are, where it's headed. It gives them that, that space that they don't normally have in a regular day. People find that extremely valuable when they're reflecting back on what that particular eight hour day did. That's a very common, common reflection. What it also gives them time to do is without distraction to intensively concentrate on solving for a particular problem. Let's go back. Are the right people in the right seats to spend an hour and a half, all of the senior team examining the people who individually report to them and figuring out how aligned those people are with the, the corporate or the business's value system and how effective they are in doing their work and then figuring out which of those people are in the right place to be counseled and which not. So that's, that's really valuable time. The people make the business. Find the right people and you'll build the great business. So there's a lot of emphasis on that. And this gives them the time, the space, the tools and technique to enable them to do those really important things that in the heat and rush of the everyday cut and thrust don't get done. [00:18:47] Speaker B: Tell us a little bit about what that looks like both in sourcing and managing excellent top talent. [00:18:56] Speaker A: Here's a good example of one of the tools that I bring which assists senior managers to do that. Imagine you have three piles. One of big rocks, one of medium rocks, pebbles and one of sand. Most people will start the day metaphorically taking the sand into their day, which is the, the water cooler chat, the catch up on the sports stars, what happened on Netflix. They put that in the, in the jar. Then around 11 o' clock they realize they've got some really urgent stuff, that's the pebbles. And they get on with the urgent stuff and they fill with the urgent stuff. Comes four o' clock in the afternoon, there are some big rocks over there. Those are the things that actually move the business that they try and squeeze in but they can't teach them to flip that on its head. Start with the rock. Start with the things that really going to move the needle for your business. Spend the first two hours of the day on those. Then put the pebbles and they fill in around. Those are the important things they've got to get done every day. You Spend the next few hours on that. When you come to the end of the day, you can fill that sand. You can talk to people about Netflix sports calls, what's happening tomorrow. It all fits. And you move the business on. Those are the kind of lessons. [00:20:03] Speaker B: It's beautiful imagery and I love. You know, you can really see those different elements going into a jar and how the sand is the last thing that fills in all the cracks. How in practice do you take that beautiful analogy and teach people to change very ingrained habits? [00:20:20] Speaker A: What you do is you actually give those rocks names. They become specific projects. Some people actually start to put rocks on their desk. [00:20:29] Speaker B: I love it. [00:20:29] Speaker A: And move them from one side to the other, demonstrating they've actually done something in those first valuable couple of hours in the morning. You give them names, you create special project, you create project names with steps, timelines, deliverables and responsibilities. [00:20:46] Speaker B: Wow. I love the idea. I mean I'm a very visual person, so that appeals to me in a big way. But I think making something tangible when so much of our work in the professional sphere can feel very intangible or there's not the immediate outcome. Whereas growing up. Right, right. Exactly right. Growing up you're doing a puzzle and you put the last piece in or even in school you take a test and within a certain amount of time you know that you'll get the results. But so often we're waiting and so I love that it gives you a little piece of immediate gratification and also helps you with retrain your brain. [00:21:24] Speaker A: And it's all backed up and supported with a portal I use where those projects rocks will be there. [00:21:31] Speaker B: Love it. I love it. This portal, is that something you developed in house? [00:21:35] Speaker A: That's developed within the Summit OS system and it's available to all my clients. Yeah. [00:21:39] Speaker B: What made you want to create a digital system to complement the one on one consulting? [00:21:45] Speaker A: I think this mirrors the worlds in which our clients operate. They all have digital stacks, technology solutions. Business inevitably moves in that direction and it's proven ineffective. So really just doing, showing good practice that we're teaching to our businesses. [00:22:05] Speaker B: Right. I think you're such a good point that so many businesses are going digital in some way, even if it's maybe not the first thought that occurs with whatever the business type is. But as you're. You were thinking about making that investment. You know, software development is can be capital intensive. What kind of work did you do ahead of time or indications from the market? Did you have that said this is the right place to be able to invest. [00:22:32] Speaker A: It's, it's a well trodden path in the world of business coaching and consulting to have a digital portal of some, some sort. This is, this has been developed. There are third party providers now whose business model it is to provide these platforms and then tailor them for your particular coaching system. And so you know, it's, it's, it's very cost effective to leverage their investment into your particular application. And of course a lot of the dev work is offshored and so in terms of investment dollars, it's very, very effective. [00:23:07] Speaker B: What are the other big costs in your consulting business? Of course I know it is your time, but as if someone were trying to think about what would it take to scale profitably and effectively a consulting business. What are some of the cost factors they should take into consideration? [00:23:22] Speaker A: It's very efficient from a cost point of view. You have very little investment in equipment, people, outside resources. And so the, you know, the ideal business model is one way in which you minimize the committed, outgoing monthly cost and optimize against a good sized client portfolio. And the leverage is just fantastic For. [00:23:43] Speaker B: A business that's earlier on that maybe doesn't have that client base as they think about marketing spend, how do you do that effectively? [00:23:51] Speaker A: Okay, so the, the methodology of building a good consulting practice, good coaching practice is also quite, quite a well understood thing. It's a combination now of networking both directly with business owners and with other advisors and introducers to those whom one already knows to get a multiplier effect there. So that's the whole market, that's the whole networking protocol. And then there is a digitally based marketing methodology, for example through LinkedIn posts and boosts and other digital media like podcasts that we're talking on right now. Gaining visibility is important both in the broader sense and specifically with individual prospects. And working that thoroughly, consistently, driven by an intense interest in other people is really the key to success. [00:24:47] Speaker B: And in a market that is potentially highly competitive for others offering similar consulting services, whether it's for the M and A advisory or fractional cfo. How do you think about differentiating yourself and how much of that is leaning on your past experience versus what offerings you bring to them in the future? [00:25:10] Speaker A: Yeah, I think certain of those places are quite competitive and well populated markets. For example, the fractional CFO space has now gone that way 10, 15 years ago. Not so much. That's, that's really, really. Come on. I think, listen, we've each got our own life experiences. I think articulating those in a relevant manner is the best you can do to promote yourself to or promote your message to your prospective clients. I try and emphasize that my history of going through so many exits both prepares me to support my clients on the way up towards that point very well through all the learnings and failures of those who failed to achieve to get that, achieve that and get paired but also then positions me well to advise them on actually the execution of an exit through the president I have in the investment banking market Marula Capital and I'm putting that for example to good use right now in Nexus, a roll up of accounting firms accounting and tax preparation firms in America where a joint co founder and I he has done this already in the uk. He's also a UK based accountant. He's come over here and together we are building a pipeline of acquisition prospects, building a support base amongst investors and applying some of these principles that you and I have been talking about Stiri to bringing businesses together and getting them working better than they were. Standalones yes. [00:26:46] Speaker B: If you have a particular example, perhaps take us through an example of when you identified a potential client for Summit OS and what did the communication cadence look like? Did you do any sort of free premium type work for them to show them your work product and then how did you close the deal? [00:27:04] Speaker A: So I have to be a little bit discreet obviously in terms of identifying clients who like to remain private. So I'll be a little generic in my description. The onboarding process for this company which creates beautiful adverts for TV advertisers and linear and non linear adverts. The onboarding process here is starts with a warm introduction in this case through the CFO who was a colleague of mine to the CEO who was at a particular point facing retirement of one of the senior people challenges in the industry through AI impacting movie production and a ambitious but partly unskilled group of upcoming senior people. So good timing. Onboarding process is a 60 to 90 minute so called discovery call in which I will demonstrate just a little bit enough to get people interested of these tools and techniques in Summit OS and also run a pretty challenging session getting them to think about and reveal some of their their own challenges. The objective of that no cost, you call it freemium, that is a perfect freemium is to get to a decision point hell yes or hell no. So it's an efficient use of time and that then leads if it's a yes to the booking of a first eight hour base camp day one which is not charged in advance and only paid for if ultimately at the end of the day client is satisfied. So I take a big commercial risk on the basis. I'm confident that this business will love what they hear and experience and want to pay for it and move on to the second of the two basecamp days. Thirty days later, after 45 days, the business should be experiencing and they do what we call execution momentum. They will be noticing a real difference in the way things are happening day to day and a real acceleration in how they're feeling about growth. We then take that on through the monthly cycle of measuring success against those rocks and seeing how those rocks are building towards the annual objective. As we get towards that point at the end of the year, we're looking at the growth path further up the mountain towards the summit. And the whole analogy as you have got by now in this thing is mountaineering and scaling the heights of your company's summit. That summit may be the point of exit or it may be the point you get to and realize. Actually I got three or four adjacent markets which are even bigger than the ones I've already been addressing. Those are the next summits on the next range. [00:29:57] Speaker B: And I'm sure the fact that you not only do the initial 60 to 90 minute coaching session plus the full 8 hour day without seeing a dollar upfront, gives your potential clients an incredible amount of confidence that you are going to bring a lot of value because you have the belief in yourself that they are going to see the change in the value and be willing to sign that at the end of the day. [00:30:20] Speaker A: I think that's like any good commercial deal. Both parties have skin in the deal and both are very heavily incentivized to create success. And those are the dynamics of a good deal. [00:30:31] Speaker B: Ian, what does victory look like to. [00:30:33] Speaker A: You today from a personal point of view? Victory looks like the satisfaction I get when I'm working with my clients and they get it, they implement it, they achieve it and at the end of a, let's say a one year cycle, they have objective measures of their success along the path they've chosen for themselves. They've implemented the tools that I've effectively taught them, they've responded to the coaching that I've given them which can sometimes be a bit of, you know, you better get a move on on this because you're not achieving and you've only got six months left of the year and re up for the next year continuing the journey. I feel victory in their success. [00:31:13] Speaker B: I love that in being an accountability coach, even though it sometimes comes with a tough love that is how you see the results and that that's a win for you because you know that you are having a positive impact on them and of course, course they're seeing the tangible results in their business and. [00:31:29] Speaker A: Then they go on and refer to some friends, other business people they know because they've been successful. That feels great too. [00:31:36] Speaker B: Amazing. Yeah. A very natural flywheel. [00:31:38] Speaker A: Yeah. [00:31:39] Speaker B: In terms of reflecting on your career to date, if you could go back and tell your younger self one piece of advice, what would it be? [00:31:48] Speaker A: Self doubt does nothing and you know, just get on with it. It all comes around. [00:31:53] Speaker B: Just get on with it. Get those boulders moving. I'm ready to go find some rocks. [00:31:57] Speaker A: Move those big rocks. [00:31:59] Speaker B: I love it. [00:31:59] Speaker A: Fit in. [00:32:00] Speaker B: I love it that that image is going to stick with me. Ian, thank you so much for your time today. It was a fantastic conversation. [00:32:06] Speaker A: My pleasure. Good talking to you.

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