Jordan DiPietro: The 3H Leadership Framework and Why Every Founder Needs a Coach

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The Business Owner's Journey Podcast host: Nick Berry
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Transcript for Jordan DiPietro: The 3H Leadership Framework and Why Every Founder Needs a Coach

00:00 Pattern Recognition and Founder Coaching

03:46 Autonomy and Founder Burnout

06:18 Knowing When to Make a CEO Transition

08:37 Accountability and Self-Awareness for Founders

11:29 Balancing Professional and Personal Goals

14:00 Leadership Framework and Pattern Recognition in Business

17:02 The Three Signals Diagnostic for Founder-Led Companies

22:02 The 3H Leadership Framework

27:33 Why First-Time Founders Don't Know What Great Looks Like

33:17 Why Every Founder Needs a Coach

36:44 The Founder Handoff and CEO Transition

Jordan DiPietro (00:00)

action creates information. And so the faster you move, the quicker you do things, the more information you get, good or bad, you know, but you gotta get kind of that feedback loop going. And when you're in a group of, you know, individuals like Hampton or Vistage or whatever it is, and you can quickly share ideas, get feedback, that's just one form of like, yep, quicker the better.

Nick Berry (00:06)

you

Jordan DiPietro (00:19)

That was one of the things that I first fell in love with as a marketer was like how quickly you could throw up a landing page or shoot an email at, you know, and almost instantaneously, you're getting, you're getting data back.

Nick Berry (00:42)

Jordan DiPietro is the former CEO of Hampton, which he led to a $10 million ARR. ⁓ He's also the former CEO of The Hustle and he spent decades in the C-suite with Motley Fool and the HubSpot. Now Jordan's coaching founders trying to scale without burning themselves or their teams out.

So what happens when a high performing founder realizes that they are the thing that's holding their company back? Today we talk about the patterns that keep showing up in every founder led company and what to do about them. Expect to learn what his 3-H leadership framework looks like in practice. How pattern recognition shortcuts the problems that every founder thinks are unique to them. His three signals diagnostic for what's really broken in a business. Whether high performance culture and treating people well can actually coexist.

what the founder handoff solves about CEO transitions, and why founders who grind the hardest often have no idea what great looks like. You can find out more about Jordan and get his newsletter at jordandipietro.com. Now enjoy this episode with Jordan Dipietro

Jordan DiPietro (01:38)

I love betting on myself and I love having flexibility and autonomy and, you know, more time to make sure that I'm focusing on the things that I want to focus on. also at the end of the day, if something's not going my way, it's like, well, I'm the only person to blame because I'm doing my own thing, you know? And so, I think you're just able to react.

quicker to when you see something you like or you're enjoying doing it, you can turn it up faster. And when you do something that you don't love or that maybe you thought you might enjoy, but you don't have a passion for, you can turn it down faster too. So I think just the autonomy over, you know, professional and personal has been just pretty incredible so far.

Nick Berry (02:17)

Do you think that this is more of what your path is going to look like in the future than bigger, bigger businesses, bigger teams?

Jordan DiPietro (02:24)

Um, it's hard to say. try not to honestly look like too, too far ahead. Um, you know, you never know what kind of curve balls life throws out, even what opportunities there are. But I think what I can say is I'm, you know, what I realized last year when I stepped aside was I thought what was happening was I was burned out after, you know, 20 plus years of grinding. And I wanted to like my, you know, my friends would make fun of me. They're like, you're going to small R retire. And so I thought what was happening was I just don't want to work that much anymore.

you know, because I'm just burned out. I'm just going to take it easy. And what I realized maybe three or four months in was that actually wasn't the case. I don't want to work for other people anymore. And I want to just do things my way. don't have a whole lot of tolerance or capacity for doing things other people's way anymore. But man, I'm still just as ambitious as I was 10 years ago. And I love working. And that's not a good thing, a bad thing. It just is what it is. And so I think what I realized was

I don't want to necessarily not work. Maybe I don't want to work 70 or 80 hours a week, but I still love working and I love building. I just want to do it my way. So do I think that this is kind of the end all be all that all I'm going to be doing is coaching other founders and CEOs and writing a weekly newsletter? No, I think it'll probably be bigger than that. But do I have aspirations that I need to build a billion dollar company? I don't think I need that personally for myself. I don't need the

recognition or fame or accolades of certain people to do and I don't need the wealth either that other people do. So I think it'll grow from here for sure but I don't think that I have any desire to go and build a hundred person team and get to a hundred million in ARR again. I think I'm good.

Nick Berry (04:04)

You only have to do things like that one time.

Jordan DiPietro (04:06)

One time is funny, man. One time is funny.

Nick Berry (04:09)

do you think that your need for the autonomy and wanting to do it your way has always been there and your resilience for it, you kind of reached a point where it's like, no more? Or did you evolve to where that became more important to you?

Jordan DiPietro (04:25)

That's a great question. I think autonomy has always been important to me for sure. But I also think that there's an arc, I think, in your career. And in my career, think the first 10 or 15 years of my career, even though I had a lot of autonomy and I had incredible managers and bosses and leaders who gave me lots of autonomy and lots of responsibility before I even probably earned it,

I still was in a constant mode of learning, know, and constant mode of like absorbing new information. And even if I mastered a certain role, then there was a new one to go on to. And so it felt very much like the kind of classic visual of like climbing a ladder. It felt like there was always more ladders to continue climbing just in terms of my own learning. And now that I think there's less to learn now,

But I do think that I've done so many different things, whether it's been product, whether it's been marketing, growth, ops, obviously in the C-suite and then being the CEO two different times as well. I feel like I've done so many things and now I just know how I like to do it. And so I just think I have less of a tolerance for different people's points of view that are impeding on my values or the way that I like to do things.

Now that I'm not still open to other people's points of view, I think there's different types of points of view, right? It's good to be open to different people's points of view if it comes to like business strategy or how to approach a problem or lots of other things. But I think when it comes to your own values, the things that you kind of hold as non-negotiables, I think it's good to be kind of, you know, steadfast in those things. And so when you're leading a company and you're the CEO of a company and you're calling all the shots, you really have to be, you have to make sure that you're kind of holding steadfast to those things.

And guess I just have less of a tolerance for doing things at that high of a level other people's ways than my own.

Nick Berry (06:18)

you've had a kind of a cool path. So butcher, Motley fool, HubSpot, Hampton, a lot of questions come out that, but like, how did you know it was time to make those changes?

Jordan DiPietro (06:21)

Thank

Yeah. You don't ever really know, honestly. I was having this conversation with, I'm interviewing for an assistant right now and one of them asked me a really good question that was similar to that. And I would say, you don't ever really know, but I love taking risks. When something starts to feel really comfortable to me and like I'm not being challenged anymore.

I think I start to get like little bit of like internal agita start like freaking out a little bit and I start feeling like a desire to move and kind of do something different. And I mean, I was at the Motley Fool for over 12 years, which obviously, you know, in today's world is like four decades, you know, an incredibly long time. And when I started there in my mid twenties, I was a writer writing about tech stocks and media stocks. And I kind of climbed up and did lots of different roles and learned a ton.

I it was the best education I've ever gotten was my 12 years there. But near the end, it felt like there was nothing left for me to do. I had literally done every major role of the company that I was interested in. And after working for over a decade on the same sort of business model, you know, solving the same sort of problems, I just kind of thought there's got to be something different. But it was hard. It was really, really hard. mean, when you spend that long at a place,

Those people are your family. You get very comfortable. know how to, not only do you know how to solve the business problems, but also the people and the political problems. You get so comfortable in a place and it was incredibly hard to move on. But, you know, was fortunate enough that Sam Parr had approached me and, you know, recruited me to come and be the CEO of the Hustle. And that felt like an incredible, you know, kind of once in a lifetime opportunity. So I jumped at it, but you don't ever really know. I think everything is a little bit of a leap of faith.

you know, do the same things that most people do, prone cons list, man, you know, talk to your closest friends, talk to my wife. But I love tackling new problems and I get really excited easily about new business problems. And so when something gets presented to me that seems excited where I think I can add value, it's hard, it's hard not to say yes.

Nick Berry (08:34)

Yeah, And just hearing you talk about some of the things that you said are,

Important to you, know, the risk taking and the buck stops, my words, but like the buck stops with you. If something doesn't work, you know, those are things to me that, that speak like accountability, right? Is that, is that, would you describe it like that? Or is that off the mark?

Jordan DiPietro (08:49)

Mm-hmm.

For sure. Yeah,

no, I'm definitely a high agency, high accountability sort of person. You know, the other thing I was just thinking about as you were kind of talking was I've been for the last, I don't know, five to seven years, I do like many people goal exercises with myself at the beginning and end of every year. So one thing I noticed because I do these exercises with myself and I've got different categories of goals, you know,

fun, family, friends, financial and professional. And every single year, the beginning of the year, I'll write down very specifically, like, what are all the things I want to accomplish this year? I'll check in with those goals quarterly. I like write myself little notes, update them. And then at the end of the year, I kind of do a review. What did I accomplish? What did I not? Kind of help me set up for the next year, et cetera. And what I noticed at the end of 2024, when I was reviewing my goals going into 2025 was,

I had gotten really, really good at consistently hitting my financial goals and my professional goals. And the two or three years prior to that, I kept missing 50 % of my family goals. And it was really pissing me off. And I've got a really beautiful eight and 11 year old who I'm, you just in awe of. And I was like, there's nobody to blame but myself. You know, at the end of the day, you've got to kind of…

Sometimes things can be pretty binary or black and white. And I kind of looked at it and said, look, at the end of the day, I am trading my very, very finite amount of time with my kids at this age for professional satisfaction and future wealth. You know, and like that's either a trade that I'm okay making or it's a trade I'm not okay making and neither is right or wrong, you know, and everybody's different, but I just kind of thought it's not really the trade I want to be making. And so at the end of the day, it's like, well,

You keep saying this, you keep missing some of your goals that you keep writing down. So, you know, are you going to do something about it are you not? And that was kind of when I made the decision that I was going to step away from CEO role and do something myself.

Nick Berry (11:01)

Most people do yearly goals, but I think it's really easy to let those kind of be gone, right? You turn the page to the next year and they're gone and not do too much reflection, especially if it stings. ⁓ And then you can, you can let that trend be, you know, five years, 10 years, 15 years, what? You may never catch it.

Jordan DiPietro (11:12)

Mm-hmm.

Nick Berry (11:21)

Like that's a scary thing to think about that you could have the epiphany that you had if it had taken you twice as long. Right? Like that's, I mean, I don't want to be flipping about it, but like tragic, right? That's a long time in your kids' lives, especially.

Jordan DiPietro (11:21)

Right.

Yeah.

Yeah.

For sure, for sure. I've been lucky, Nick. I've had some tough tragedies in my own life, but the benefit of having tragedies in your own life is it gives you perspective and a point of view on timelines and how kind of fleeting certain things are. So I try to hold some of those things pretty close to the best because it does make you kind of…

just realize like, you know, how short certain things are. And, you know, my, some of my, friends and family or my wife make fun of me because I'm constantly trying to optimize or like, what are you, you know, what are you optimizing? But I'm like, I'm trying to optimize for my own happiness. And what are the things that I want to achieve? You know, and it's in lots of different categories. but you gotta, you gotta be really clear with yourself about the priorities that you have, you know, and then make sure that your actions are following those things. And that's the hard part, you know, that's the real hard part.

Nick Berry (12:33)

So professionally, is it that you are the best at?

Jordan DiPietro (12:36)

Ooh, that's a good one. What am I the best at?

I think that professionally the two things that I am really, really good at, one I think is just being a incredible leader. I think that one of the main jobs of a CEO at a company is leading a team and to achieve a certain vision for a certain outcome. I think leadership is a very, very soft and hard skill. And

I've learned from some really, really great leaders in my life and CEOs and founders. I like to say, and I hope I've taken a lot of the good stuff that I've learned from them and applied it to myself. So I think that just leading a team and a company is definitely one of the strongest skills that I have. I think probably the second one is just pattern recognition at this point. One of the reasons that I got into coaching, we haven't touched on this too much, but like the

coaching advisory work that I do, it kind of fell into my lap a little bit a couple of years ago. But one of the reasons I've continued it is because what I've seen in my career with myself, with my own teams, employees, and now with lots of different founders that I coach, is that everybody thinks that their problems are unique. Everybody thinks that their companies are incredibly novel, you know, and oh, what I'm doing today, so you'll never understand what it is we're going through and the challenges we have.

But at the end the day, actually, it's not true. know, for the most part, like we're not building rockets. Most people's problems are all similar. And I call it like, I've got a loose framework for it. call it the three signals, but most people's problems in their company fall into one to three signal categories. One is self, two is team and three is model. And I can go into those more detail if we want, but basically just noticing those things over and time and time again, it made me realize.

how much I'm able to kind of help people through those problems. Again, just based on pattern recognition from just doing it for such a long time, making lots of mistakes myself, again, learning from others. And so I get really, really pumped and excited about helping other people because I think I'm just, I'm able to spot the reoccurring challenges and these kind of reoccurring themes that are going on in people's companies. And I love diving in to kind of help.

Nick Berry (14:53)

Yeah, so give a little bit more on the three signals, the self, team, and model.

Jordan DiPietro (14:59)

Yeah, so self is like, you know, working with founders to kind of look inward a little bit and trying to see what are the things about themselves that could be potentially holding the company back. So this could be, you know, an identity trap. Like maybe you're working with a founder who's just used to being an operator and can't let go of anything. So now they've hired a team that they're constantly micromanaging. Maybe they've become the core bottleneck in the company.

Maybe they're not great leaders. Maybe they haven't had the luxury of working for great leaders, so they don't actually know what great leadership looks like. Maybe they've simply never done something as elementary as just auditing their own calendar, and they don't realize that they're not spending time on the things they want to be spending time on, and they're not focused. There's lots of different biases involved with decision-making. Are you making good decisions? Are you not? Are you delaying your own decision-making? So there's all these different things when it comes to self. Team.

A whole host of other problems. Maybe you don't have an operating structure or cadence with your team. Maybe you don't have a hiring system in place to make sure that you're hiring A players. Maybe you're good at identifying talent, but you don't have a system in place to actually retain your A players and your high performing individuals. Maybe you've got talent gaps on the team and you're not really sure where or how to fill them.

You know, maybe you've never been intentional about building a culture at your company and just kind of happened by accident, but now it's starting to fall apart. So there's always different things can, can start to impede your company on the team. And then model is all the business mechanics, you know, um, and there's, you know, a myriad of things that could be going on in somebody's business. Um, you know, you've got marketing issues, sales issues, maybe your, your revenue is great, but your margin stinks. Maybe you're hedging in your ICP.

Maybe your positioning or pricing is off. You know, there's millions of different things that could be going on from a business mechanic standpoint. everything by and large, I've never run into a problem with a founder where it's not a part of one of those three categories, self team or, you know, or model. It's usually one of the same five or six things underneath each of those categories.

Nick Berry (17:02)

Yeah. And so you're able, you can just kind of step in, see the symptoms, map it back to that framework and essentially you should be able to shortcut somebody to here's the problem most likely. You know, we can validate that and then get to solving it. Yeah.

Jordan DiPietro (17:11)

Yeah. Yeah.

Yeah, and

I think it's one of those things, you working with people that have done things that you haven't done before, or maybe are either ahead of you or just on a different track than you are so incredibly helpful, you know. And yeah, it's like, why not give yourself all of the advantages that you can by trying to work with folks that are, you know, that are, I mean, I love reaching out to other people to learn from them what they've done. Just try and find as many shortcuts as you can.

Nick Berry (17:41)

Yeah. I mean, pattern recognition is probably the thing that I've grown to appreciate the most over 20 years that I've been in business for that reason. whether, it's recognizing a pattern for myself or for somebody else it's just there's the cheat code in there. I mean, I I really don't like using that language.

Jordan DiPietro (17:51)

Right.

Nick Berry (18:00)

But if there is one, it's being able to connect with people who are going to be able to do a quick diagnostic and help you bypass the queue in banging your head against the wall and figuring something out on your own.

Jordan DiPietro (18:11)

I was going to ask you real quick. What do you have any pattern recognition when it comes to when a guest comes on the podcast? Is there anything that you can tell on the first 30 seconds or a minute if it's going to be a great conversation or a dud?

Nick Berry (18:23)

You know, usually it happens before the podcast. because it doesn't take much, but just in the engagement with like how easy someone is like, Hey, yeah. Send me an email. And then it's booked like probably the, the speed to getting just the few things that we need done. It's like,

Jordan DiPietro (18:27)

Hmm.

Nick Berry (18:45)

you know, people who are the kind of people who are the guests that I want to have are going to be busy. They're going to be people who get things done. They want to like let the simple things be simple. And we'll spend our time doing the like the heavy lifting and, and you can just kind of see that's how it unfolds.

Jordan DiPietro (19:03)

interesting. So the most, yeah, the biggest signal for you is actually happens before you even get on with someone. Yeah, yeah, yeah. No, that sounds right. That's cool.

Nick Berry (19:09)

Usually, yes. And I mean, I try

not to, to like, create any expectation about, or think that someone might not be a good guest in advance, because it really doesn't matter whether I'd be right or wrong. Like I've got to go in and as if they're going to be great and, and stay out of their way. So yeah, most of the time they're, the signals have been there in advance.

Jordan DiPietro (19:21)

Right.

Nick Berry (19:31)

Um, but so to go back to the pattern recognition and its effect on you and, and at being a strength. And that to me makes perfect sense why something like Hampton would appeal to you because. So, um, you know, was a 10 year Vistage member of one of my companies. We, uh, it was a coaching business that we built. had, um, one-on-one coaches and did small groups like peer groups. And, and we did that because of my experience in.

Jordan DiPietro (19:48)

and cool.

Nick Berry (20:01)

Vistage and knowing like the, the advantage that it can give you putting yourself in the room with those other people who you have more things in common with who are like-minded in some ways who have either been there or done that, or are going to do that. They have some perspective on what the challenges that you're going to face that it's, can only serve to help you get through those things faster.

mean, at the end of the day, like speed, you have to have to find ways to access speed on this journey, or you can, you'll run out of juice really early on just banging your head against the wall, right?

Jordan DiPietro (20:38)

Yep, no, absolutely. I think one of my favorite kind of sayings is like, know, action creates information. And so the faster you move, the quicker you do things, the more information you get, good or bad, you know, but you gotta get kind of that feedback loop going. And when you're in a group of, you know, individuals like Hampton or Vistage or whatever it is, and you can quickly share ideas, get feedback, that's just one form of like, yep, quicker the better.

Nick Berry (20:50)

you

Jordan DiPietro (21:03)

That was one of the things that I first fell in love with as a marketer was like how quickly you could throw up a landing page or shoot an email at, you know, and almost instantaneously, you're getting, you're getting data back. You know, it's like, I mean, I'm dating myself now, but this was, you know, decades plus ago, it was just so incredibly exciting to get that kind of dopamine hit, you know, when you throw something out onto the internet and you get some data back, but that's like early stages, right?

understanding the importance of action and getting information back to help you make better decisions.

Nick Berry (21:35)

It's funny that you said that I was looking for something in my email inbox today and I have emails from you, from Motley Fool in 2013, maybe even 2012, until I saw them. I was

Jordan DiPietro (21:46)

That's amazing.

Nick Berry (21:48)

Yeah.

Jordan DiPietro (21:47)

That is wonderful. That makes me happy.

Nick Berry (21:49)

So it makes me happy because I've been looking for someone to thank for Nvidia in like 2011. yeah.

Jordan DiPietro (21:56)

you're welcome. You're very welcome.

Nick Berry (22:02)

So tell me about the 3H leadership and operator framework.

Jordan DiPietro (22:07)

Yeah, so I basically have just been trying for a long time to sort of distill, you know, whatever my own leadership philosophy or ethos kind of is, you know, and I, like I've kind of said earlier, I've taken many things from other people. love the radical candor framework. There's a lot of different ones that I kind of, again, I'm like taking parts and pieces from, but what I've landed on, like you said, I call it 3H, which basically stands for

high expectations, high support and high transparency. And, you know, there's components to each of those. But I think what I started noticing maybe halfway through my career was there were certain companies that were known for being like pretty hardcore performance driven companies and they had hallmarks of type A, ruthless, maybe didn't treat people the best.

pretty harsh, very, very stringent hiring practices, easy to let go of people that were underperforming, but incredibly high IQ sort of people, right? That was like maybe one model of company. And then another model of company was, you know, companies that were people first or culture first companies. And they tended to be, you know, have wonderful culture. They would get the high glass door awards, great benefits.

lots of freedom and flexibility, maybe didn't fire as much, looser standards, like very, you know, like almost more fluffy, you know, people friendly sort of companies. And I never, I never really understood why you couldn't be both. And I have to credit, you know, my first five or 10 years at the Motley Fool for kind of showing me this, but at that time I would say that the company was very high performance and very high expectations and a people first company as well.

But I just don't see it that often. I still feel like I tend to bump into companies that are more one way or the other. They either don't treat their employees incredibly well, but they preach high performance, high performance, high standards, high standards. But then the founders or the CEOs aren't actually that great to their employees and their employees end up burning out, not being that loyal or turnover quickly. Or they treat their employees incredibly, but they're almost too nice because they're used to avoiding conflict.

They don't want to let go of people until their performance standards are kind of lower. So my philosophy is like, I don't see any reason why they have to be mutually exclusive. So I'm all about high performance. Like if you're working with me or you're working at a company with me, the fucking ceiling is high. Like you have got to perform. You have got to hit your numbers. I expect a lot from you. But also you could ask any of my employees, like I also love the shit out of you.

and I will be there for you. I will do anything in my power for you, your family, your career. I will invest literally like personally, professionally in you. And now that doesn't mean if someone's not performing that I can't let them go. But also there's right ways and wrong ways to do those sorts of things too. And then high transparency is kind of the last leg of that stool, which is again, not every founder agrees with this, but I personally like to share

the numbers, I like to share the data, I like people to know how the company is doing and I like people to know how they're doing. And so I'm incredibly transparent with both of those things, which again, I think makes for a better team and a better culture, but certainly isn't everybody's cup.

Nick Berry (25:26)

Yeah, so what kind of founder is the right fit for you?

Jordan DiPietro (25:30)

Well, I think somebody has to hear those things and say, that sounds like me. And again, it's not right or wrong. It's just what I have found to be successful. I'll meet founders and they'll say, man, I really want a loyal team. Or God, I keep having all this turnover. It's super annoying. I got to take all this time to go rehire. How do I get people that are going to stay here forever?

you know, and then I'll start asking them questions about how much time and energy they put into hiring, how much time and energy they put into their benefits program, how much time and energy they put into just recognizing individuals that work there, doing things like office. I mean, there's so many little things that you can do to recognize your employees, you know, but the point is I'll start asking all those questions and it's obvious they spend no time doing that because for most founders, I think it's more fun and more natural to build products.

or to make sure that your customers are being satisfied. It's less fun and more of a pain in the ass to make sure you have a lot of clarity around performance reviews, to make sure that when somebody doesn't do something well, that you actually take the time to sit, not when you're pissed off or frustrated, but to sit with that person and explain to them what they did that wasn't up to your standards. And also more importantly, what great looks like.

So lots of founders will be like, hey, I just fired off an email to my growth marketer and told them that this thing stunk and the landing page was terrible and we didn't hit our numbers for X, Y, and Z. But then the follow up question is, well, did you show them what a great landing page does look like? Did you make sure that you were clear at the beginning of the campaign what numbers you were expecting? It's like, well, no, I just kind of assumed they I'm like, that's bad leadership. That's not high support. It's not high transparency.

You don't have to have all those things that I listed, but I think if you're working with me, then you've got to have a desire to have those things. And I think a lot of founders are kind of fooling themselves if they think they're going to get really, really loyal, long-term, high productive employees without also supporting their employees.

Nick Berry (27:33)

Yeah. Do you think that they are kind of sticking with more of the tendencies that got them there?

Jordan DiPietro (27:39)

Yeah, I think that's probably part of it. also think like candidly, Nick, many, many entrepreneurs have always been entrepreneurs or they've always been doing their, you know, a lot of the people that I work with are solopreneurs or solo or first time founders. They've done a thing because they were either solving a pain point that they had or chasing something that they're passionate about. And they did it and they did it and they were persevered and resilient and

10 years into it, they're like, holy shit, I have a $5 million revenue company. You know, it's like, they didn't set out to build a company and they also don't know what great looks like because they've never worked anywhere that was great. They've just been grinding, doing the thing. And I think that's where some of my experience is really helpful because, you know, I spent over a decade at the Molly Fool, which I think was the best in class company of its size. We were around probably 50 million when I joined, maybe 400 million when I left.

Obviously then I went and worked at the CEO of the hustle, which was an incredible company. It was a startup at the time acquired by HubSpot. Then I went for almost two years and was at HubSpot, which is also, think, a best in class kind of midsize SaaS company. And then of course at Hampton. So I have all these different experiences in different industries at different sizes and scales that I can pull all the great things, discard the not great things to come up with my own, know, formulate my own opinion on what great looks like.

And I just feel like a lot of first-time founders, have no context, right? To understand, what can it look like? What are the benefits of treating your employees really well or making sure that even though doing performance reviews is a huge pain in the ass, how to do those really well, you know, because they just haven't experienced it. So it's not even their fault. They just, they don't know what great can look like. And so I think that's what I love to do with the clients I work with is kind of give them examples. Like this is what it could look like.

you know, paint that picture for them and let them kind of take their own approach to get there. You know, so it's not a copy and paste sort of thing, but it's like, Hey, here's one example of how I do it and the results that I've seen. Can you take this and kind of mold it or modify it to be your own? I think the best clients are like, hell yeah. You know, they're, they're excited to do that.

Nick Berry (29:50)

Yeah. Well, I mean, for, for a lot of people, especially achievers who are going down that path, they're, they're just trying to figure out what it's supposed to look like. They, probably know that it, the role has evolved. The business has evolved. What it needs out of them has evolved. They've evolved some, but they, they're trying to figure out like, well, what's this supposed to look like next? mean, when, so we were talking about being in info marketing 15 plus years ago and we're like,

Jordan DiPietro (29:55)

you

Mm-hmm.

Nick Berry (30:18)

I mean, had a company was doing well and we're like, we don't know what this is. Like we don't know other businesses like this. So we're really not sure what we're trying to, to mimic or where do we look for inspiration? And that's just, that's an odd place to be, but to have someone in your corner, can say like, for someone in your stage here are the patterns that typically went out or that some of the actions, the things that you need to be thinking about. Right. Yeah. That's, that's invaluable. And,

Jordan DiPietro (30:22)

Right. Right.

Yep. ⁓

Nick Berry (30:46)

You don't know what you don't know. None of us do. And that's not, that's not the problem. It's when you're not trying to find out what's in those blind spots that it is a problem.

Jordan DiPietro (30:48)

Yeah, right.

Right. And it's funny, I see a very similar pattern with people that will reach out to me and I'll get an email from a founder and it'll say, know, Hey, you know, read your newsletter or I listen to you on a podcast or I saw you on social. Like I'd love to, I, you know, I desperately need you. There'll be something urgent in the email. Like I just lost my three hires or we just crossed 10 million and I don't know what I'm doing. It's usually urgent. Right. And so I emailed them back. Sounds great. Can't wait to learn more about your company. You know,

fill out this 10 second form and set up a call. And then typically there's like some week, two week, month long period where then it goes like crickets. Because what happens is as founders, as busy business owners, like then we go back to putting our heads down and doing all the things that are on fire, crossing things off our to do, you know, like we all just go back into our own worlds. And then I'm like, I just kind of smile. like in a month or two months, I get that same sort of urgent email back. I can't believe this is slipped. many, know, can we, can we find time, you know, tomorrow morning? You know, it's like.

Nick Berry (31:55)

Mm-hmm.

Jordan DiPietro (31:56)

And

sometimes it takes one or two of those. And then we get on and we have our first kind of meeting and they're like, you know, then it, then everything clicks and they realize, but, it's hard. It's hard to take time out of the day to day running our business. Also coaching, whether it's, you know, business coaching, executive coaching, having a personal therapist, anything like that. Like it feels like a luxury, right? Like it's so hard for any of us to be like, am I really like, that's what I'm going to pay for right now for.

a therapy session or coaching session or coaching. It's funny, I just shared a really interesting email last week in my newsletter written by, I forget the gentleman's name, but he's like one of the world's top surgeons. And he had hit a plateau in his career, like I think late 30s, early 40s or something, plateau meaning his error rate in the surgery in the operating room. And then he hired a coach, one of the best surgeons in the world. hired

one of the other best surgeons in world to basically go in to the operating room and watch him do surgery. the point of the article, I think in essence, like everybody needs someone to help them. Again, whether it's a therapist, a good friend, a coach, advisor, whatever, but it's hard for all of us to justify those sorts of things. Cause for some reason we feel like it's a luxury versus it being like an actual business necessity or personal necessity, you know.

Nick Berry (33:17)

Yeah. Yeah. But I mean, I think if you, if you get into it, the business case is pretty easy to make when most of the people that you're trying to emulate their path or their, their success, like, they've all had help along the way. And something that I hear that I've heard it for years and it still makes me scratch my head a little bit is the, when a founder or owner is saying things like, well, I should have to do that. I'm the owner. So I should have to figure this out on my own.

Jordan DiPietro (33:30)

Yeah.

Nick Berry (33:45)

It's like it takes something away from it. If they get help. I'm like, it's going to be a tough, tough road. If you're going to try to approach it that way.

Jordan DiPietro (33:45)

Mm.

Right.

Yeah, no, absolutely. I like to sit like, I like to tell people early in the business that you should try to understand everything in your business at a basic level and do everything once, but then delegated outsource it, scale it, whatever, you know, I think it's great. mean, I'm having been just an operator my entire career, right? Like I, it's also hard for me to like take my hands off the wheel sometimes. And I think there's a real advantage to.

understanding how to do most everything in your company so that you can hire well for each position so that you actually know how to evaluate people and whatever it is that they're doing. But unless it's incredibly high value, you know, as soon as you know what it is that needs to be done, you know, find leverage in your time and figure out somebody else or a different way automated, find a system, hire someone, you know, offshore, but do what you can to kind of continue to free up your time to focus on like the highest value task for sure.

It's hard. It's super hard for all operators, I think, to do that.

Nick Berry (34:49)

Leverage.

Yep. Yep. And some of us are maybe predisposed, maybe wired a little more for it than others. coming out of my time in the fitness industry, a lot of people that were getting business coaching were practitioners, they wanted to stay the practitioner. So you're having to balance that. circumstances and individual preferences, but at the end of the day, leverage is the word.

Jordan DiPietro (35:10)

Yeah.

Go.

Yeah. Yeah. I'm, I'm, there's a CEO I'm working with right now. She's absolutely wonderful. She's got a $50 million revenue business, first time CEO, and she inherited a very, very large team. It's probably not the same team that she would have hired if she was starting from scratch. And she said something to me in our last session, which I've heard a million times before, which is like, it's just faster and easier if I do it myself, you know, I'm like,

Nick Berry (35:18)

regardless.

Jordan DiPietro (35:43)

How are you ever going to find out who are the right people to keep and who are the right people to let go of or to move on from if you don't actually give people an opportunity to do it? It is hard because it's harder and it takes longer to stop, not do the thing and to coach someone and walk them through how you would do the thing. It's just simple. It takes longer. ⁓ It pays greater dividends in the long run. But man, when you have only a certain number of hours in the day,

Nick Berry (35:52)

Mm-hmm.

Yep.

Jordan DiPietro (36:11)

And you're like, well, I could send that email myself or I could walk my EA through how I would send the email or man, could, you know, I could build this campaign myself, or I could sit down with my junior growth market. You know, it's just, those are, those are hard decisions to make, but they're the right ones.

Nick Berry (36:25)

Yep, that muscle memory is tough to retrain or to get to work through.

Jordan DiPietro (36:31)

Totally.

Because going back to those dopamine hits, I mean, you get a quicker dopamine hit by doing it yourself, you know.

Nick Berry (36:34)

Yep.

Yep. So is there anything about your current, your advisory work or any specific topics that you want to make sure that we get mentioned?

your work with your advisory has moved into this hiring, finding, any C-suite roles?

Jordan DiPietro (36:49)

Mm-hmm.

Primarily right now, I'm just doing founders and CEOs, but I have recently had folks reach out to me who want me to coach up their leadership team. So I'm exploring that a little bit too, but for the most part, it's been just founders and CEOs.

Nick Berry (37:03)

tell us about that.

Jordan DiPietro (37:05)

Yeah, so right now, most of the coaching is one-on-one based, again, with founders and CEOs, typically in the 2 to 20 million revenue range. But one of the new things that I'm really excited about too is I partnered with a good friend of mine, Ty Burke, who runs an executive search firm. And one of the things that I've noticed in my career, having been a CEO that's been hired twice into a founder-led company and also somebody who has worked

in a founder led company for 12 years of the Molly Fool was being a CEO in a founder run company is a really, really unique challenge. I think both for the incoming CEO, but also for the existing founder. And I think that you can hire the best executive search firm in the world to go and get the best candidate ever. I still, think that there's some really important foundational work that needs to be done with the founder ahead of time to make sure that that transition is a success.

So Ty and I have partnered together to create this kind of product called the Founder Handoff. And essentially what he and I are doing is combining my skill and expertise, helping founders figure out, know, decision right mapping, role clarity, operating cadence with the new CEO, developing an onboarding plan and Ty's skill set and expertise, which is finding the best CEOs in the world to come and take over founder led companies.

So we just launched this a week ago, so we're pretty excited about that right now.

Nick Berry (38:29)

Yeah, it's a matchmaking service, And it's a tough match to make, which is why it's such a great idea. I love that.

Jordan DiPietro (38:31)

Yeah. Yeah.

And there's, you know, one thing I've noticed, Nick, is like, there's so many companies now that are founder led that are somewhere in the 10, 20, we'll call it like 10 to $30 million revenue range. The founder has built the company themselves. They've grinded for 10 plus years to get the company to where it's at. And they're either burned out, want to go and build something new. Maybe they've got young kids and they started a family, but whatever it is, they know that they're ready to move on. But the.

prospect of having to find a CEO, how much equity are they going to have to give away? What are they going to be in charge of? What's the CEO going to be in charge of? How can they make sure that the new CEO is going to be successful? All those questions are so overwhelming, but there's so many people in that scenario. And so I'm really excited to kind of just like dive into that world and help people make those transitions. Similar to how I made the transition in my life from being a full-time CEO,

to now doing my own thing. And it's been such a, you know, incredible blessing for me. So I love the idea of like, just helping push people over the edge to make that decision, but make sure that it's successful.

Nick Berry (39:43)

it's a unique situation, but you're well-designed for that, which is because you've got a unique path and skillset yourself. So that's awesome. Jordan, I I appreciate it. This has been great.

Jordan DiPietro (39:50)

Yeah. Yeah. Cool.

Awesome, man. Yeah, that was wonderful talking to you,