1272: The Goldhill Group: Generational Business Wisdom and Practical Advice for Successors with President Jonathan Goldhill

Jonathan Goldhill on Family Business Growth

Jonathan Goldhill covers Family Business Growth in this Marketer of the Day episode. Jonathan Goldhill shows how "disruptive successors" can modernize a family business and still keep relationships intact. He argues most breakdowns are about communication and trust, so he starts by facilitating frank cross-generation conversations. With EOS, Scaling Up, and Rockefeller Habits, he redraws the org chart, defines five key functions per seat, and sets a simple scorecard of metrics. He uses "delegate and elevate" to loosen the founder's sticky baton while keeping clear authority and accountability. He hires and coaches for Pat Lencioni's ideal team player traits: humble, hungry, and people-smart, reinforced by a few memorable, actionable values. Citing that only about 13% of family firms make it to a third generation and under two-thirds reach the second, he pushes focus on the vital few.

Running a family business comes with pressures that outsiders rarely understand—balancing tradition with innovation, managing family dynamics, and keeping the business alive for future generations. When visions clash between the old guard and the next wave, the result can be stagnation or, worse, collapse. But failure isn’t inevitable. The businesses that survive find ways to blend experience with fresh ideas, respecting the past while adapting to the future. The question isn’t just how to keep the business running—it’s how to build a legacy that lasts beyond any one generation. The right balance could turn survival into long-term success.

Jonathan Goldhill, a family business advisor, executive coach and the President of The Goldhill Group, has over 30 years of experience helping small and mid-sized businesses thrive. Author of Disruptive Successor and host of its podcast, he specializes in guiding next-gen leaders through generational transitions. With an MBA from USC and a family background in business, he understands the complexities of growth and succession. Today, he talks about the challenges family businesses face, emphasizing how younger leaders can innovate while maintaining trust, communication, and strategic alignment across generations. Stay tuned!

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Robert Plank 0:04 Hey, we're here with Mr. Jonathan Goldhill. He's a family business advisor and executive coach, growth coach, and he is the author of the very excellent book disruptive successor. And he's the podcast host of the disruptive successor show. And Jonathan is a business coach with over 30 years of experience, and he helps leaders of small to medium sized businesses, many of them family owned, achieve financial success and personal freedom. So we will find out from Mr. Jonathan himself, about who is a disruptive successor, how he helps disruptive successors, and what this idea is all about, as far as scaling up Rockefeller habits, Eos, and what Jonathan's coaching does, as far as helping you with your growth strategy, exit planning, strategic planning, scaling up all of that, how he stands out, how he can help you. So, Jonathan, glad to be speaking with you.

Jonathan Goldhill 1:03 Robert, thanks for having me on the show today.

Robert Plank 1:07 Glad to have you and so I'm here all about to get you energized and get you jazzed up by talking about what you do to help people and just what gets you excited to jump out of bed in the morning. So what is your recurrent focus and passion.

Jonathan Goldhill 1:22 So, you know, it's funny that you say that, because I get excited talking to other people about their challenges and their opportunities in their businesses and helping them. And it was pointed out to me recently that I've developed the consultants affliction having been a consultant and coach. Now for 3035, years, I'm great at asking questions and interviewing people, but I don't talk that much about myself, but I have to say that I wrote this book, disruptive successor, a guide for driving growth in your family businesses, and then I launched my podcast a month later, and this was all in 2020, during the beginning of the pandemic. And I'm really excited about what I about working with what I call disruptive successors, and that is a next generation leader, typically a millennial, taking over a business from their mother or father or both, who are typically baby boomers, and they know that to lead the company in in the way that it was led. But even better, greater that they need to be somewhat disruptive Robert. They need to change the way things were, because they know what got them there. You know, without got them here, isn't going to get them there where they want to go. So that's, that's kind of the concept. And look, if I can just go on for another moment, I'll tell you that what excites me about family businesses, and it's been in my blood. I mean, I went to business school and got my MBA from the University of Southern California go Trojans. Sorry, a little plug there. And that was back in in 1989 and I studied entrepreneurship in the MBA program. But I was keenly interested in family businesses, because that's what my family had, which was a large men's clothing manufacturing business, and it made it through three, arguably, maybe some, some fourth generation family members, but there really wasn't anyone to carry the torch. It was my grandfather and his his two brothers that were disruptive with their dad, and started at a very young age and built a very large business. And I would have been part of that fourth generation. I would have loved to have been part of it, but it just, it got sold off, and so it was just part of my legacy.

Robert Plank 3:56 And so there's a lot to navigate there, right? Just as far as I love this idea of the past generation. They did things a certain way, and then they pass it on to the next generation. And you would hope that the younger, up and coming generation that they can step up, and they also don't let their ego get in the way. And you would also hope that the older generation kind of advises and helps out, as far as building their legacy and that that they don't get in the way, but they also don't kind of prop the younger generation up too much, where they can't survive on their own. And it it seems kind of exhausting, and it's like you see this in reality and in fiction, right? You see it with like, the the Trumps, and you look at like, how those generations kind of acted, and then in like a TV that the show succession, right? That's a lot of fun, that's right there in your title. And you see, like, the the patriarch figure, he's all about the newspapers and the TV, and then the younger kids are all about like, internet and apps and websites. And you're like, Well, neither of them. Has a very good solution, right? The older generation, it's like, well, that's that worked, then it won't work now. And the newer generation, it's like, well, maybe they don't have it all figured out. And so in reality, what do you see when someone comes to you? Is the situation similar to succession or the the Trumps? Or is it something similar, like, what's the before picture? Look like?

Jonathan Goldhill 5:23 Robert? I think maybe I've been lucky up until now, or blessed that I work with what I think are pretty functional families. I would say that succession, which is loosely based on the Rupert Murdoch family, is a very dysfunctional family. There's no right, there's no doubt there. And And arguably, I guess, the Trump family is pretty functional, highly functional, but that's because there's a strong command and control in Donald Trump, the the leader there. And so what I find is that sometimes there's a strong command and control, and the typically, the father is getting in the way. Sometimes they've abdicated control and sometimes they've delegated control. And like what I teach is oftentimes so valuable, is about delegating with some authority and with some control, but letting go and learning to let go. And so this sticky baton syndrome, you might call it, I've got to come up with a better analogy. But where you know the old man is holding on to the baton too tightly, or or the young adult is grabbing it too quickly. I mean, it's a nuanced dance, and what I find that I'm really good at and valuable at is facilitating a conversation between these two generations and putting in some processes that they never had before, for how to run meetings, for how to measure what's going on in the business, for Having for how to have clarity and visibility and transparency around the agenda for growing the business. And I find that if we brought it broke it down to one word two, I'll say and this is no different than marital relationships or business partnerships. It's communication and trust. When you have communication and trust, and then you have some good systems in place. Then we can talk about technology. We can talk about, do we do a social media campaign? Do we do an old school advertising campaign? But these are, these are some of the debates that go on, and obviously technology and AI that that's a huge disruptor that is changing the landscape of all businesses, family businesses, especially,

Robert Plank 7:48 very nice so communication and trust and processes, and when you think about some of these, these concepts didn't even cross my mind until maybe, like five, six years ago, right? This idea that, well, if you don't have at least some boundaries or rules, then chaos will just sort of take over, right? And the the boundaries and the rules to be set anyway, it's just you won't be thinking them through, and it will be up to random chance. And so that's kind of an idea, just that, on its own, is, is navigating family, marriage, friends, right? You don't want to ruin it by adding a bunch of rules, but if you just let random chance happen, then it it'll just happen to you anyway. And so as far as this idea of you come to these family businesses, and they're more functional than than fiction would have us believe. So that's good. And then you say, Well, now you need to set these processes here to get the clarity and figure out the meetings and so, like, what does that look like? Do you have an example of, like, what it's like for you to put some of these processes, boundaries, rules in place for this business that's in this transition period.

Jonathan Goldhill 9:02 Yeah. So some of it looks like it starts off as me teaching some of the business growth tools that we use to help our clients make this for instance, I talked about, like practicing. I didn't talk about in terms of the vital few or trivial many. There's the EOS system, which uses something called delegate and elevate, but there's many varieties of this, and teaching this one tool as an example helps people to figure out what is it that they're really great at and they should be spending more time doing, and what is it that they should delegate and have someone else do and so getting people into the right positions, you know, on the organization chart, and then having them have clarity about what are their five key functions in that position and and what are the you know, metrics that they're being measured by? So when we start putting in processes where we've got metrics, we've got meetings, we've got priorities, we've got clarity around the business plan. And I'm teaching all this through the use of some tools. Business Growth tools really teach people how to think differently, and they'll look at their business differently. And so what's very popular these days, because it's become well funded, is the EOS Entrepreneurial Operating System, and this is an example of what it looks like when I go into a family business. It's not just about using some of the tools I learned from Rockefeller habits and scaling up, but it's about keeping it really simple and having people utilize the tools that helps them put these processes and manage their meetings better. So that's kind of what it looks like.

Robert Plank 10:54 And I think this is a really important conversation to have, and I love tapping into this business person's mindset of having things written out, but having it simple, because if it's not simple, then it'll just be a waste of everyone's time, right? It was. It would be a waste writing it down. No one will use it. So we need the simplicity. That way everyone's on board. That way everyone revisits. And I love this idea of like, doodling, mapping, diagramming, figuring out the org chart, figuring out what those five qualities are. And to help us get an idea, like, when you go to someone, you say, hey, this person, here's where their strengths are, here's where they belong in the org chart. Here's what they should focus on when they list these five qualities. Like, what are those like? Do you have a good example of like what they what their five qualities or skills are that they would really want to lean into.

Jonathan Goldhill 11:47 So if I understand correctly, what are the skills or qualities or characteristics of a human being that make for a successful transition between one generation to the other? Is that what you're asking

Robert Plank 12:01 I'm asking, like, a little, a little there, we're close. I'm saying, like, say, there's all these people in the organization, right? And you say, Hey, here's this person we're focusing on, and they have strengths and weaknesses, and here's, like, here's five things they should do more of, like, what? What might that be?

Jonathan Goldhill 12:18 So I think oftentimes it'll depend on this position and the strength, and that's where I'll use some psychometric instruments like behavioral assessments or profiling to understand, what are they naturally good at? Right? Some people are naturally good at motivating and managing people. Some people are good at operating things and fixing things. So, you know, right? I wouldn't put a mechanical person in a leadership role managing other people. They would probably do pretty poorly. So what I look for are more soft skills and general types of characteristics. I love Pat Lencioni concept of what is an ideal team player. So I look for people that are humble, hungry and smart like people smart, because if they're humble, then they will be open to learning. If they're hungry, they'll have a drive, and if they're people smart, they won't be tripping over people in the process of trying to get things done, or walking over people. So I like those characteristics a lot. And and then it's about figuring out how people are wired and helping them to understand that how you're wired, for instance, and how I'm wired, they're going to be different. So if I know how to communicate with you, if I know how to motivate and manage you, and vice versa, you know about my you know behavioral profile or tendencies, then we'll get along a lot better. So using some of these types of team building tools really helps in the process of getting a really strong organization and culture working together.

Robert Plank 14:08 I like it so hungry, humble, smart, yeah, yep.

Jonathan Goldhill 14:11 And I'll add one more other thing, which is that one of the first things I do with most of my clients is figure out two things. What is their why? Why? Why are they in business? Just like you started with the earlier question in the interview, why do you do this? What gets you out of bed in the morning? Because I think if you get with a really good why, or purpose, or mission, whatever you want to call it, although mission sounds a little too military, but if you come up with a really clear purpose, then it motivates everyone to get out of bed and get everyone get excited. And then the second thing that I work with my clients early on is making sure that they have really clear values around the business. And sometimes there's family values, and those might be a bit different than the business values, but what I'm talking about is, what are the handful of. Rules that you'll absolutely follow, and they're already living and breathing in the organization. They're not aspirational. So this is what builds a strong culture. So if someone can't fit with the cultural norms of the company, then they're probably not going to be a great team player or a great fit. So that's something else I look for, core purpose and core values.

Robert Plank 15:23 This is fascinating to think about, and it seems to all be with the objective of making sure everyone is just going in the same direction, right, that people aren't fighting. And I like how you say that. Well, these things like the the purpose and the values, they already exist. They're just hidden. They're kind of like you and I, you. We have organs in our body. We have blood flowing. It's all there. We just aren't aware of like, okay, well, my pancreas is here, my kidney is here. I don't really think about it until I learn what's already there, and then maybe I'm more well informed about what I'm doing moving forward. And so you provide this really needed service to take inventory, so to speak, and figure out what's going on within the organization. And so when you ask these deep questions, you ask about things like, what's your purpose? What are your values? Do the team members usually like, have a good guess. Are they giving like, similar answers, or is it just total chaos? Before you get there,

Jonathan Goldhill 16:22 they don't have good answers, and oftentimes they're similar. I hear the platitudes from the 80s where it's, you know, it's integrity. That's the word. I won't let anyone choose as a value, because everyone's got different definitions around what integrity is and looks like, and people bring into the relationship baggage from their prior history around integrity. So they usually give me these, like 80s things like leadership or teamwork, or, you know, humility, and these one word things are not so helpful because they're not actionable. And so I coach them on. Let's create some values that people can remember, that people feel are authentic, that don't read like a poster from a company that you know where you walked into and they had those posters on the wall with a one word thing. So that's usually, and people, what I see, and people really have no clarity on their why. It's usually about making money. And I always say, look, it's not about making money, because you could have done anything else and you chose this. So why did you choose this? And we dig and we dig and we dig, and sometimes we get to an aha moment, and that's when I know that we're on the right track. So really important to get that stuff right, because that's what builds excitement. It feels like you know when, when you are part of a cause, like, well, you'll die for that cause, almost, but if you're not part of it. You're just showing up, you're punching a clock, and then you're going home. It's a different thing altogether.

Robert Plank 18:07 Yeah, we want to have this purpose. We want to get excited if you're just running out the clock making money. That's not a life and that's not a very fun and interesting organization that doesn't attract people in and that's not something that lasts decades or generations. And so I love this idea of moving beyond the superficial, moving beyond the one words. It's kind of like when someone asks you about, well, what kind of a romantic partner would you like? And you haven't thought it through, you say, oh, I want someone who's kind and honest. Well, everyone wants that. What's more unique and specific to you, and what is more exciting and passionate. And so it's great that we're thinking these things through. And as far as this powerful why? Right? Like, I struggle with this sometimes, but every now and then, and I'm sure you come across this with you meet some amazing podcasters. You come across someone who, like, whoa. They really know their why? Like, I came across a guy a few years ago. His mission was to remove all plastic from the oceans. I'm like, that's, I don't know if anything bigger. So as far as when you help these people come across their Why have you come Have you experienced something like that? As I did, of like, you were blown away with like, man, that's like the best answer I've ever come across, as far as their why?

Jonathan Goldhill 19:26 Yeah, well, I think that it's easiest to point to the companies that we all know. I almost would say and love, but sometimes there's a love hate relationship. But for instance, I think of Tesla and Elon Musk, and what was his why? I mean, when he started Tesla, it was about creating, like, sustainable, electrical, you know, I can't even remember now, but it was about making it. Changing the entire automobile and transportation, and it was about electrifying everything. Or you take Starbucks, which was about creating a place between home and and work that felt like a third place that you wanted to hang out at, or Disney, where you'd look at a company that wanted to create a happy experience for everyone in the family, that everyone could enjoy, right or or 3m A company that wanted to provide innovative solutions to sometimes the smallest of problems. But so there's really, there's companies that have a big why that are game changers. So, you know, I use the Tesla example, and I unfortunately didn't explain it well, but you take his company SpaceX, which has been in the news lately because of the satellites that that kind of blew up, but his whole idea was to colonize Mars. Now I think that's pretty crazy, but there's probably a lot of people that think, like, wow, that's really cool. Let's do that. And obviously, you know, $550 billion market cap, or whatever it is later, there's a lot of people that believe in it. So I think when you have a really big why? Then you it foments incredible change within a company and and I'll just point to a couple of more examples, right? So when John F Kennedy said that we're going to put a man on the moon, he had no idea how it could be done, but he had a vision that it could and should be done. And so that was a big why. And a lot of the folks that worked in places like Jet Propulsion Labs, they figured out how to do it. Or when Martin Luther King talked about, you know, having peace on earth, I mean, I don't think he knew exactly how, but he felt it in his heart, and he created an entire movement of people that followed him. So people will follow the causes and people that they believe in and think are changing the world. You know, not a lot of people want to work for a ho hum company. And this is, this is what's challenging, by the way, at Robert and family businesses, because they might have been around for two or three generations, but to stay relevant, they're going to have to go through some really and maybe enormous changes. Right? You can't stay in the printer industry for three generations. If everything goes from analog to digital, you can't stay in the music industry. You can't stay in the you know, in every industry has been disrupted by technology, and now AI, you've got to continue to figure out, how are we going to make ourselves relevant? And so that's the big challenge, wonderful, and it is a challenge,

Robert Plank 22:55 but that's why your book isn't just and your podcast, it's not just successor. It's disruptive successor. So that way we can make waves, have this big, hairy, scary goal, and get other people on board. You think about how Commodore was a typewriter company, and then at some point they said, hey, you know, typewriters are going away. We need to make computers instead. And I just, I love the cleverness of some of these purposes of these companies, right? Three? I'm saying, well, let's solve the small problems. Post it notes Starbucks saying, let's make the third place. And you think about Elon and the I think I've been hearing a lot lately his goal of like being not just on Mars, but like us being like a multi planetary species. And you think, Well, cool, that plugs in the SpaceX for the rockets. You got Teslas as like, maybe like the rovers or the cars on other planets. You got the Solar City. You got the boring company. It's kind of fun to think about, like, man, like, all these things interconnect together, but it seems to require a lot of thinking, and especially help in thinking, from someone like you, right? You mentioned a lot in this conversation about the personalities, and perhaps, if someone has the the way that they've been doing it so far, and they've still got a ways to go, there's like developing their skills, finding their inner self. There's a disconnect between the way they see themselves and how others see them, or what excites them, on what they're good at. It's a lot to navigate, right? You need someone like you to figure out the org chart, to figure out these processes, these rules, and how can someone find out more about that? You have your book, you have your podcast, you have your company. If someone has gotten a little bit of a taste a tease about these ideas, because it's a podcast, and they say, Okay, you got my attention, but now I need more structured training, and kind of, you know, to actually get educated properly. By Jonathan, where should they go to get more of that education from you?

Jonathan Goldhill 24:52 So I am a very personable, I think, person, and I think it starts with a comment. Conversation, because, right? I mean, I have found chat GPT amazing, and I you can almost use it as a proxy for a coach by asking it really good questions and getting into a dialog. But I think that I've got my book, I've got my podcast, there's all sorts of other tools that will help people to figure out where they need to go, but I think a conversation with me where I can go into areas that might be blind spots for them, and that's not going to be picked up by an AI tool, not yet, not today, but I think that as a human being, I have the ability to go in and look for those blind spots. So I always invite people to, let's have a conversation. Let's talk about, you know, what are your challenges? What are your opportunities? How might we navigate through these things? That's usually where I like to begin.

Robert Plank 25:57 And where can they begin with you? How do they have that conversation.

Jonathan Goldhill 26:00 So they can go to my website, the Goldhill group.com, or and they can contact me right on my website. They can find a place to submit a request to have a conversation. They could reach me through LinkedIn, Jonathan Goldhill business coach, that's where I do most of my posting. And they can also check out my book website, which is disruptive successor.com and they can book a conversation through there as well. And so if you are having trouble in a family business, or you're even an entrepreneur and you're a next generation leader, and you need to level up all the next generation leaders. I look, you know, welcome people to reach out to me to have a conversation I understand the emotional, the relational and the structural complexities unique to family owned businesses and entrepreneurial businesses. So I think that's a great place to start. Those places,

Robert Plank 27:05 I think it is to have that person to person conversation, so that way you can have that chat. Jonathan seen so much, you can explain your situation. Only 13% of family businesses last through three generations, and less than two thirds survive through the second generation. This is scary stuff, right? You need help with some of this, and the ways that Jonathan said you can get help is number one, there's on LinkedIn search, Jonathan Goldhill, business coach, Adam on there. That way you can see his latest updates. That book we mentioned a few times is called disruptive successor, a guide for driving growth in your family business. But where Jonathan really wants you to go right now is the Goldhill group.com where you can transform your business. Check out the ultimate guide for next gen leaders and owners. You click on the button there that says, book your Are we a fit call and get that conversation started. And as Jonathan said a few times here, sometimes you have blind spots, right? You don't know what you don't know. You check out the books, the podcast, the chat, GPT, the Google searches, the articles, and you're looking at it through the lens of like you think you have it figured out. You know about all those known knowns, but what about the the unknown or the known unknowns or the unknown unknowns, right? There's all this other stuff that maybe you hadn't considered. And we've all been there where we just we had that one conversation with a lawyer, accountant, teacher, mentor, and we made it so complicated for ourselves. And that person that has just been around the block a few times said, Hey, you're stressed out about 37 different things. Didn't you say, Jonathan, that was called like the there's like the the many, the trivial many versus the the few things to be focused on, Vital Few? Exactly, yeah, the the trivial many versus the vital few. So have that conversation with Mr. Jonathan Goldhill, from the Goldhill group.com and figure out what are those vital few things that'll move the needle, that'll disrupt this family business for the next generation, that will get you on this path to Starbucks or 3m or a Tesla, or wherever your dreams take you? Right? How this big, scary goal, that way you get people on board with you who are just as crazy with you who are help get aligned and get you in that direction. And so as people are heading to the Goldhill group.com, Jonathan, it's time to put you on the spot a little bit. I hope that's okay. This is the part of the show where we it's kind of scary. We try to ask our guests about a fun or interesting quote or lesson that has served them. And you have your books, you have your speaking, you have your podcast. You're a man of many words. So what comes to mind for you as far as a fun quote or lesson that has served you in life or business?

Jonathan Goldhill 29:53 Yeah, so I think a really good quote comes from Buckminster Fuller, who was a a. Systems thinker, an architect. He was most popularly known for having created the geodesic dome, which didn't exactly become a worldwide success, but he did say this, if you want to teach people a new way of thinking, don't bother trying to teach them instead give them a tool the use of which will lead to new ways of thinking. And so that quote means so much to me, because I think that what I oftentimes do is give my clients a business growth tool that allows them to organize their thoughts, their their or organize their thinking and changes their behavior. And it's it's the use of that tool that now teaches them how to manage that activity, going forward, whatever activity that is

Robert Plank 30:59 very nice. So lived experience, right? Learning the facts and figures only get you so far. And what will really help you is going to the Goldhill group.com that we Jonathan, can introduce some of these business building tools to you, so that way you can break out of your own limited thinking and your own current frustration you solve problems. And Jonathan mentioned a few times about the ripple effect, right, that you you become a leader to others, and then, and then they're elevated, and they become a leader to others. You as a business owner, entrepreneur, you seek problems. You solve problems lead you to bigger problems. It's beautiful. It's wonderful to think about, especially moving into the future, and double especially as you go to the Goldhill group.com and you take what what helped you and inspired you today in our podcast conversation and use it as the motivation to contact myth reserve Jonathan Goldhill. You click on the button to book your Are we a foot call. You have that conversation. You tell Jonathan how impressed you were by him being on the podcast. You say, Here's my situation. Can you help have the conversation? You have fun, and just like Jonathan and I had fun today. So thank you very much, Mr. Jonathan Goldhill, author of disruptive successor, a guide for driving growth in your family business. The Goldhill group.com really appreciate you being here.

Jonathan Goldhill 32:22 Thanks, Robert. Appreciate your your time, and you're a great interviewer. So guys, listen to Robert's podcast. You got so many episodes. It's kind of amazing to me.

Robert Plank 32:38 This is Robert Plank from dfy podcast.com, forward slash free. Me and my team are super excited to jump into your podcast, whether it already exists, whether it's brand new, whether it's just in the idea stage, set up a call and contact us today. Claim your free gift at DFI podcast.com/free, and we will see you there. You.

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