313: How to Break Ceilings in America with Ian Leaman

https://youtu.be/ivElg53993A Ian Leaman, Summit OS® Guide, former investment banker, senior finance executive, and investor, is driven by a mission to help entrepreneurs build, scale, and successfully exit their businesses by applying the hard-won lessons he’s learned from more than 100 exit journeys. We learn about Ian’s path from growing up around small family businesses in the UK, to training with Deloitte, advising entrepreneurs through hundreds of M&A processes, co-founding a SPAC, and ultimately relocating to the United States to embrace a more optimistic and opportunity-driven business culture. Ian explains his Can-Do Framework, a mindset blueprint inspired by the contrast between European “can’t-do” thinking and America’s bold, frontier-style optimism. He also breaks down how Summit OS® empowers owners to achieve “private equity–level growth without giving up private equity,” and why the 45-Day Execution Momentum plan creates faster change than a typical 100-day private equity program. Ian closes with a gripping case study illustrating how leadership blind spots and misaligned incentives can devastate exit outcomes. — 313: How to Break Ceilings in America with Ian Leaman Good day, listeners. Steve Preda here, the Founder of the Summit OS® Group and host of the Management Blueprint Podcast. And my guest today here is Ian Leaman, who is a Summit OS® Guide, a former investment banker with over 100 exits under his belt. He’s also a senior finance executive and an investor. So Ian, welcome to the show. Hi, Steve. It’s great to see you, and thank you for having me on.  Absolutely. And we go way back, and one of your international board positions I think I’m sharing with you, but I’m not going to go into that because it’s long in the past. What I like to explore is what you’re doing now, why you’re doing it, and some things about why you moved to the States. I mean, both of us moved to the States since we were on this particular board for different reasons. And I’d like to explore your framework, which is very intriguing. So let’s start with your ‘Why’. So what is your personal ‘Why’, and how are you manifesting it in your business life?  What I’m doing right now, Steve actually squares the circle. It brings us back together as working colleagues. You mentioned that we worked previously on an international board. Today we’re working together as Summit OS Guides. How did I get here, and how does this relate to my ‘Why’? Well, my business journey started really in my youth, where my parents had small businesses. And so the conversations over the evening dinner table were all about the trials and tribulations, the successes, failures, challenges, et cetera, of running a small business. So that got into my blood very early. That translated through a career in finance, where I qualified originally as an accountant with Deloitte in the UK, and then progressed into the transaction side of finance, helping entrepreneurs grow and exit their businesses. As you said, having come through more than a hundred successful exits, but many  more which didn’t cross that finish line.  I really became interested in the differences between those who succeeded and those who didn't, what they were doing in their businesses, which made them attractive prospects from an M&A point of view and made their processes successful ones. Share on X And eventually, I came to reunite with you when you’d started your Summit OS® Initiative and understand that we can bring our respective experience, whether it’s as a CEO of a previously exited business or as an advisor to many which have done that, we can bring that experience to there. And how that translates into my personal ‘Why’ is I get huge satisfaction out of being involved in and assisting the process of entrepreneurs building and exiting their business. And I find huge satisfaction in a successful outcome there. So my personal ‘Why’ is to work with entrepreneurs who are building their businesses to help them do so better, faster, more successfully, and, if relevant — which isn’t in all cases — take them across that exit finish line to a conclusion of that particular part of their business journey. Yeah. I totally relate to this, and I often felt guilty even when we sold the company, and I felt like we could have gotten more for it if the company was improved, and there were some low-hanging fruits that we could have helped fix in a short order. And then we can do it now, and that’s very fulfilling. That’s right. I mean, there are many war stories, if you like, from that phase of my working life that illustrate very well the point you just made. For example, on the positive side, I can recall a conversation with an entrepreneur. I met him for the first time at his place of work. It was a distributor of electronic components, so they bought in bulk, stocked, broke into small pieces, and sold and distributed at a good margin, electronic components. They had a big warehouse. He and I had an initial discussion and he was quite an impressive guy. I remember in his very austere functional office, and he said, would you like to look around? I said, yeah, of course. I’d love to. So we walked together from the upper level where his office was down a stairway into the warehouse. And just as we got to the foot of the stairway, we encountered one of the warehousemen. His name was Jim, and he said, the owner said, Hey, good morning Jim. How’s it going today? And Jim said, 81%. Why did Jim say 81%? I asked myself, I left it at that moment, but they were both very satisfied with Jim’s answer. When we returned from the visit to the office, I said, so what’s 81%? He said, well, that’s Jim’s metric. Jim has to measure a certain number of things he’s doing and relate them to that day, and he was well within his range of target, and that’s how this guy ran his business. All that translated into a very successful exit at a multiple one or two points above the regular for a distributor in that sector. Because he was growing fast, he was doing it really well, and he built a business which was somewhat independent of him.  That’s great. And just a quick reference to the LinkedIn post that you put up yesterday, where you mentioned that a lot of people who are trading time for money and working 55 or more hours is basically a leading indicator that they’re not going to build a self-managing business, they’re not going to scale, they’re going to burn out. So it’s great if someone has good KPIs to make sure that they know where they are and where they’re moving towards where they want to be. Okay, so let’s switch gears here. And you have a really intriguing story of how you made it to America and particularly to LA. So what was your calculus, and how did you end up there? I’d been working successfully as an M&A advisor — as you had, Steve — working with entrepreneurs on that journey. And a lot of that was about the growth of their companies, about building them somewhat before they actually made the exit, often through acquisition or financing. And one day I got a phone call from a friend who was a headhunter who joked with me when he got on the call: “Ian, don’t put the call down. I’m going to talk to you about a new role, which is not doing what you’re doing.” I guess his call landed at a particular moment when I was restless for a change, and he described a role as the third co-founder of a startup to be newly listed on the London Stock Exchange as blank check company, often known as a SPAC in the US. Long story short, I was a good fit for the team of two entrepreneurs who had built previous businesses, financed, acquired, IPO’d, and then sold. We got together and set out on a path of acquiring businesses in the US, even though the listing was in the UK, in the oil and gas services sector. That experience was amazing. It put me on the front line as a principal, doing many of the things I'd seen done secondhand and getting my hands into the weeds of operations much more than I had previously. And these were great learning experiences Share on X but what became most valuable over time was the experience I got working in the US and finally appreciating the fundamental contrast in business ethos between a European starting point — can’t do — and a US starting point — can do. And that framework, that basic business framework of can-do US against can’t-do Europe, really set me on the path that I then pursued. When that job came to an end and my wife and I were deciding what next, we decided to vote with our feet, relocate to the US — now 12 years ago — with three teenagers and a dog in tow, and rebuild our careers over here. That’s awesome. And that’s very similar to what we did in many ways. So tell me about this Can-Do framework. So how do you break it down? How do you make it more tangible? What differentiates an American entrepreneur or American businessperson — or just a general person — and European or UK in terms of their outlook on business or life? Okay, so it’s all about positivity. And that manifests itself with just really at the start of any conversation about anything within business, whether it’s a small change to an existing business or perhaps something at the opposite end of the scale, a big new opportunity that hasn’t previously presented itself. It’s all about the positivity. Americans will enthusiastically embrace change, generally — in my experience — without the cynicism overtaking them. Americans have just as much valid experience of what can go wrong as you build and change businesses as Europeans, but instead they choose to parlay that experience and those learnings into positive aspects of change rather than cynical aspects of resistance to change. So, for example, in America, if as a businessperson you hit some failures and those failures result in a failed business or a personal bankruptcy, those things are not regarded as necessarily negatives, which can impede your progress in the future. Quite the opposite — they can be seen as great learning experiences, which leave their battle scars in a positive way. Yeah, that is indeed amazing. I mean, you can even become president in America after failing several businesses, right? The sky’s the limit.  The sky’s the limit. That’s the point.  Yeah.  And there’s no one else’s negativity, which is going to constrain the optimistic American entrepreneur from striving to achieve their goals. All right. Okay, so there’s the positivity. I get it. So interpreting changes as looking at the positive aspect of it rather than the negative aspect. It’s more of a bold, fearless attitude rather than a conservative, resistant attitude. What else would you say characterizes this ethos? I’d say another facet of it would be the confidence to challenge the status quo. So much of European culture and business is based on history, and that history is a kind of anchor to the past, whereas America still has this frontier feeling — a sense that it’s a new country, a new world. And the status quo, such as it is, isn’t an anchor to the past. It’s actually something to be critically praised and challenged with confidence if relevant. I think that very much resonates with me personally. I recall when I was choosing my firm to join and to become an accountancy trainee, leading through a qualification to becoming a chartered accountant, and at the quality end of the range were the Big Eight in those days. I interviewed with three of the Big Eight, and interestingly, it was number eight of eight, which was the newcomer on the block, the one that resonated most with me. They were confident, they were challenging, and ambitious, and somewhat fearless in the face of challenging the establishments in the UK. Share on X And those things really resonated with me. I joined Touche Ross. Touche Ross became Deloitte. Deloitte became the number one in the world.  Yeah, that’s right.  Touche Ross was the number seven or eight, I remember, when I applied, because I went through actual same training as you did. And when I applied it was the Big Eight, and by the time I got accepted it was the Big Six — they merged — and now it’s the Big Four. So anyhow, that’s less interesting for listeners, but you’re talking about describing this underdog mentality or underdog attitude. I resonated with that as well, because when we started the investment banking business in Hungary, actually our number one competitor was Deloitte in Hungary. They were the big 500-pound gorilla, and we were the underdog. I hired some of the people who had been passed over by Deloitte, and they had a stone in their shoe about it. And we made it a kind of quest that we were going to show these snooty, self-important people that we were actually better because we’re scrappier, more innovative, and so on. That was a big driver for us — this underdog attitude. So would you say that this is something that also resonates with Americans?  I think very much so. I think that there isn’t that respect for the status quo, and the 500-pound gorilla on the block is not necessarily there to be feared, revered, or left alone. Quite the opposite. In American business, they’re the incumbent to be challenged. Challenger businesses grow to huge success in America. And actually, that links really nicely with the topic we’re here to discuss — Summit OS® — and how it provides a framework for entrepreneurs to build their businesses using many of the tools and techniques which the big successful businesses have adopted. And using that to their advantage, to creep up on them from behind and sometimes take market leadership.  Yeah, that’s a big objective, obviously, and we would be happy to talk about this, but then we would overrun our time for sure. But what is a specific concept that you enjoy about or which you are intrigued about with Summit OS® that resonates with you? One of the things that really resonated with me, Steve, having a background in investment banking as you have, is the notion that private equity doesn’t have a monopoly on expecting and delivering high growth from businesses. That principle, that objective, that achievement can be something which the entrepreneur, owner, manager can adopt just as validly. So one of the potentials of Summit OS® is private equity without private equity. You can set yourself the objective of, let’s say, 3x value in three years. Share on X You can set yourself the objective of creating a self-managing business that has a valuation way in excess of its peers because of the way you run it, because of the rate of growth you achieve, because of the differentiators it has from its competitors. And in so doing, you create something of high value, high desire, and a high level of marketability if you’re in the market to exit. That’s a really powerful and resonant aspect of  Summit OS® for me.  Yeah, I’ve often seen business owners who sold a large minority or a small majority stake to private equity. And then someone came in with an MBA but with a lot less experience, and they would start telling the business owner what they knew that they had to work on to begin with. Maybe they were not disciplined enough or not focused enough, but a coach — a good coach, a guide like you and I — could have helped them to do that without giving away a big piece of their business. Now granted, putting capital to use can be a very effective way of achieving high levels of growth. And the scale of capital that’s available from private equity may not be available to an independent owner-managed business. But having said that, I was with an entrepreneur last week, one of a group of partners who’d sold his business initially to PE, that PE had been refinanced to an even larger one. And he described his experience with those PEs as being managed by spreadsheet. It sounds like a bit of a cliché, Steve, but it’s real — that’s his actual experience. And another negative experience, from a negative point of view, that a lot of entrepreneurs have shared with me is this notion of inappropriate interference. The young MBAs just don’t get where appropriate boundaries are between them as investors and the leadership team in the businesses, and so the areas they interfere in are often not value-adding. I’ve experienced that myself, actually. I was engaged once by a private equity firm to be a consultant on a transition period. The business in question had been an orphaned subsidiary within a very large multinational corporation. When people talk about orphan subsidiaries, what they essentially mean is this businesses that don’t particularly fit within where the big corporation had moved to, and are kind of left adrift — but within. So they’d sold this business to a private equity, and the private equity engaged me to help with a transition. A transition of the business from this orphan state into an independent business. And the private equity really was clueless. The people there were absolutely clueless as to how best to manage the transition of the team, particularly the team and the way they interrelated to their ownership from how it used to be to how it was now. It’s a very good example of poor management, and I suspect it wasn’t one of one. It was one of a big pattern.  Yeah. I mean, experience is really hard to replicate in the classroom. And some of these MBAs, they come out from great business schools, and they do excellent case studies, but they just don’t have the reps to develop the pattern recognition that some of these business owners who have been in the trenches for 20 or 30 years have, right?  Yeah, you can’t put a high enough value on less experience. Yeah. And if you then harness that experience into a framework which enables people with that experience to share it really effectively with clients, that's a really powerful combination. Share on X   Yeah, I love it. Yeah. By the way, we all know that private equity groups, they often have their 100-day plan. They come into a company and then they want to make a string of changes, like a new prime minister or president would do as well. So is there an equivalent process in Summit OS® to do that? Can you speak to that?  There is, actually. And there’s a big premium today on speed of change. And the private equity guys think that a hundred days is rapid. Well, it’s not. Summit OS® has got a 45-day Execution Momentum plan, which takes the business through some very actionable processes, which result in very rapid and noticeable change. So that the 45-day Execution Momentum takes the business leaders through 2 one full-day meetings in which very heavy agenda is filled with things that really interesting and opposite ends of the scale. What do I mean by that? At the very macro, high end, there will be an examination — possibly for the very first time — of why the business exists, what it’s on the earth for, how is, how’s it going to create a dent in the universe over a 30-year period? What really big changes can an ambitious management team make in the business? And this at the opposite end of the scale, a whole bunch of very day-to-day actionable skills like how to run a really good business meeting that’s super effective and results in measurable change. And then things in between those two, which join the very high macro level to the very daily micro level. Putting these things into action over the 30-day separation period between these two days, and then a 15-day follow-on, gives you your 45 days. And that results in these really measurable, perceivable changes, which catapult the start of a company’s journey with Summit OS® — very quickly, double the speed of PE. Yeah, that’s definitely. I do believe that there’s no reason why every company should not adopt all the good management practices that already exist and widely known. And the faster we get them to adapt it, the faster they’re going to get a big push, a big momentum, and then it’s going to open them up for other changes. And suddenly this whole change management is not going to be that difficult because people will say that it actually works. So why not do more of it? Before we wrap this conversation up, can you share from your experience as an investment banker or senior CFO a story that really you feel relates to the work that we’re doing here? I can, and I’m going to illustrate this with a something negative, not something positive to learn from the negative, as I suggested. It was really valid for me to do learning from all the reasons businesses failed to get across the exit line and what we can do to help build businesses better. So, I was engaged to sell a business — owner-managed, a very successful call center business based in the UK, but with an American client base. And the vertical in which the call center business work was technology sales. So they were being engaged by large American technology houses to generate leads for selling their products into European customers. The entrepreneur who started it was an experienced businessman, but from the moment I met him, what I recognized was a brutish personality. A very tough taskmaster, very unforgiving, and actually very cold and lacking in emotion. He built this business to quite some success with a very high growth rate, and soon I got to meet his management team. These were young, thrusting, ambitious people who had been early enough in their careers for him to mold them into a likeness of his own. So what he’d created was a team of very similar-behaving, similar-acting people who were aggressive, over-assertive, cold, non-emotional in the business context and actually quite a scary team. Well, that could have been okay were it not for the fact that early on in the process, I had a word with him and I said, “Look, Chris, you’re going to need to motivate these guys in the exit. They’re well paid, but you need to give them a little bit of a taste of the proceeds you’re going to receive as the founder and 100% owner of this business. Otherwise, you might see some trouble brewing.” Nope — he wasn’t having any of it. This was his business. He was going to do this his way. Guess what happens, Steve? At the 59th minute of the 11th hour, as we came towards closing the transaction with a great buyer, the animals turned on their master. And they turned with a viciousness that was similar to his own character, and they basically held him to ransom. It cost him 30% of the business. He had to give 30% of the equity in order for them to come along and be supportive in the discussions they were at this stage, having with the buyer around satisfaction with the working there, continuing to work post-transaction and all those things that were super important for the buyer. So there’s an example, a real case study. We did actually get the business closed. It cost him millions more than it could have done had he done this deal with them early on when they didn’t have the whip hand. And here’s a great example of how adapting the way you work, respecting the senior people, and nurturing them into positions of ownership of their parts of the business, not just in terms of being mini CEOs, but actually sharing some of the equity of the business could have made a huge difference, both to the risk in the process and to the dollar outcome for him. Yeah. I think this is a common failing that the entrepreneur, they take under their wings, these young people, and they feel like that they owe everything to them for raising them. But they forget that those people stuck around because they actually had internal drive and they had ambition. It wasn’t the entrepreneur who create these people. These people were there to begin with. They just took advantage of the opportunity to have bigger responsibility, and as they rose in capability, if the entrepreneur or business owner didn’t recognize that and reward it, they’re going to go somewhere else and they’re going to get rewarded another way, or they’re going to turn on their master. Yeah. So this is a very tricky thing and you need a degree of self-awareness to realize that it’s not all you and you have to reward them. Even if you help them get there, you still have to pay them more because they did get there.  That’s right. It’s all part of respecting the people you work with and rewarding them appropriately. Yeah that’s a great way to finish this up. Okay. So, Ian, if the listeners would like to learn more about you, maybe connect with you, learn what you could do for them, where would you advise them to go? Well, it’s very simple.  They can contact me at https://ianleaman.com. There you’ll find some very comprehensive and interesting material all about coaching and about Summit OS® in particular, and how we work with businesses to help elevate them.  Awesome. So do check Ian out at https://ianleaman.com, not hard to remember. He is also has a great LinkedIn profile. And if you enjoyed this conversation, stay tuned, because every week I bring an exciting entrepreneur or business operator, or thought leader in some cases, who come and share their frameworks with us. And if you’d like to learn more about what Summit OS® can do for you, then visit SummitOS.co, and check out all the downloadable tools, videos, process maps, and everything, and client stories to learn more. So Ian, thank you very much for coming and sharing your war stories and experiences, and thank you for listening. Important Links: Ian’s LinkedIn Ian’s website