Why Founders Become Their Own Bottleneck with Cameron Herold

Speaker A: Welcome back everyone. Today I asked Cameron Herald to be here. He says most founders, they are the bottleneck in their own company and how should it be different? They run a business but they have never got the support, the training to actually do that, the skills to actually do that. He has scaled so many companies, one of them to 5,000 percent1,800 got junk in and he's about to tell us exactly how we can stop being in our own way when we run our business. Welcome, Cameron Simon.

Speaker B: Thanks for having me. Appreciate it.

Speaker A: So what's the number one thing that we are doing to be the bottleneck in our own business?

Speaker B: Well, the number one thing, it's not what I want to speak about, but the number one thing is that it's a lack of focus. I think so many entrepreneurs are just completely scattered. We're getting lots of information on social media, we're getting lots of information from the news, we're getting lots of ideas from different mastermind groups that we're in. Some of us have multiple coaches so we're getting different ideas from them. We're being told to read another book every single week. So we're getting all these ideas and it's all pulling us in a million different directions. And it's often that lack of focus. You know, if you take light and you, you disperse it, it lights up a room. But if you take light and you highly focus it, it, it becomes like a laser beam. And I think that's the big thing that's really harding most entrepreneurial companies is that lack of focus. I think the thing that I would like to really focus people on though is their ability to grow people.

Speaker A: Right.

Speaker B: If you can actually grow the confidence and the connections and the skills or the competence of your management team and your leadership team, then you can get results through others. You can scale the organization. Um, you know, everybody's job just gets easier. But most managers and most leaders have never been trained on how to lead others that are reporting to them.

Speaker A: Let's start there. How can we scale up? And even before in the age of AI, is it still adding people the number one scaling function, or is it changing?

Speaker B: It's possibly. I mean, I don't think that anyone is going to be able to deploy technology without people. So worst case scenario, you're going to one by one be replacing everyone that you have with people that can leverage technology. So I'll give you an example. You're running your own company today. How much training have you had on doing a job interview, on actually interviewing others and Selecting how much training have you had in interviewing?

Speaker A: Zero.

Speaker B: Right. Almost none. And yet you've interviewed people, you've hired people, you've hired freelancers, you've hired subcontractors, you've hired project management companies to do work for you. And we've had no training to do it. So it gets really, really difficult. That's just a good example. If you're hiring somebody to come into your organization and deploy agents across the organization, but you hire someone who's not the right cultural fit, maybe they know how to do it, but they've never done it before. Right? There's lots of people that have watched 50 videos on YouTube on how to deploy Claude code, but they've never really done it before. So yeah, if you're hiring the wrong person or the wrong cultural fit or, or somebody who's bumping up into their glass ceiling, business is still going to get difficult.

Speaker A: So the listeners right now, they're running businesses of midsize. Where do they start?

Speaker B: It's really sitting down and asking yourself what are the core things that everyone in my company that manages people does on a day to day basis? And I'll give you, uh, just a quick list off the top of my head. You interview people, you onboard and train people, you coach them, maybe you do one on one meetings with them on a weekly basis. You probably run meetings for people in the business, whether it's finance meetings, planning meetings, strategy meetings, business area reviews, metrics reviews, whether you're running project, um, wireframe meetings to build out apps, but you're running meetings, you're handling um, conflicts, you're dealing with messaging, coming in on multiple apps. But if you've never been trained on project management, priority management, if you've never been trained on this, you keep saying we need to hire more people. Well, we need to hire more people because you're not effective at leading and growing the people you have. Or if somebody's like, oh, I can't delegate this because I don't have anyone to do it, it's because you actually suck at delegation, you're bad at coaching, you're bad at situational leadership and you don't know how to actually grow others. So you end up doing your work yourself, which slows down your business.

Speaker A: What is, what makes good delegation?

Speaker B: That's a great question. Again, almost every, well I would say for certain, every leader, anyone who manages others is delegating projects and work to those people on a daily, hourly, weekly basis. So here's what makes really good delegation. Number one is Telling the person what you need back from them when it's completed so they're very clear on what the result looks like that you're looking for. Number two is letting them know how little time you want them to spend on that project. I can say, I need you to clean the office because we have people coming in tomorrow and somebody could spend eight hours doing it. Or I could say, I need you to clean the office because I've got people coming in tomorrow. Don't spend any more than 30 minutes, just get it done really quickly. It'll be done in 29 minutes. And now I've saved seven and a half hours that somebody could have spent all day trying to get to perfect. Number three is tell people how little money you want them to spend on that project. Whether it's hours or subcontractors or maybe buying software or even running tokens to actually generate the work. How little money and how little time do you want them to spend getting back what you need? And then number four is, has the person you're delegating it to got the skills and the confidence to do that project or that task or work? And if they don't, what coaching or development or problem solving or even cheering on do you need to do to help get them to success? So that's, that's just some short circuits that again, most leaders just simply say, hey, do this for me. And they miss those four massive things on getting the result. And then they sit down and go, oh, my team's terrible. I have to do the work myself. Well, no, you just don't understand delegation.

Speaker A: Two key points are hiring an executive assistant and hiring a coo. When are we ready? Is there a rule of thumb? When are we ready to do that?

Speaker B: Yeah, you're absolutely ready, first off, to hire an executive assistant. When you recognize that you're doing work that is below your effective hourly rate, or where you're doing work that is really minimum wage jobs, right? If you're booking hotel rooms, organizing flights, checking emails, replying to most of the emails, booking meetings with clients, changing schedules, um, organizing prep for meetings, whatever those things are reviewing project work, that's all minimum wage work that if you hire someone, whether they're part time, full time or freelance, and you set them up for success, you no longer have to do that work or you're just getting someone to automate and optimize some of your workflow so that you only do the two or three things you're really good at. So I've been running my own company for the last 19 years since leaving 1-800-got- junk. There's really four things that I love to do and I'm really good at. I love doing media interviews. So talking to you. I love doing speaking events and I've been paid now to speak in 30 countries on every single continent to groups of entrepreneurs. I love doing it. I love coaching entrepreneurs and I love attending mastermind groups and kind of organizational groups of other entrepreneurial minds to grow my ideas, to grow my connections and to get ideas on how to grow my, my clients companies outside. Uh, of that there's a bunch of stuff I'm good at but I don't love to do. So if you look at my calendar for this week and this month, it's almost exclusively networking, coaching, speaking and media interviews and then some project work stuff that I need to wrap my head around to then delegate the outcome and then I just simply coach the team to make sure they get to success. But I don't do a lot of the normal day to day work that a normal entrepreneur would be doing because I've tried to delegate everything except genius.

Speaker A: So executive assistant, we can start pretty quickly. I guess most, most of the listeners have one or are ready for one. The bigger lift is the CEO. How do we know we're ready for that?

Speaker B: And the first part is that. This is such a good question, Simon. Most people don't need to hire a COO right away. They need to hire their second in command. Maybe that's a general manager or a project manager. It could be a director of operations, maybe it's a VP of operations or maybe it is truly a coo. So you need to hire a second in command to again free you up to work on the bigger areas of the business that you love to do. And it's work that a normal executive assistant probably can't handle. Maybe it's leading other people, maybe it's managing P and L responsibilities or budget responsibilities or parts of the business that are above that typical EA kind of a role. And you know that if you get that stuff off your plate, you're going to generate a three to four term, three to four times return on the cost of that person in terms of additional gross margin. You also know you need to hire that second in command when you don't have time to grow the people who, who report to you. If you're constantly just delegating and managing fires and doing work and running at 100 miles an hour, your people are being ignored and your time as a leader should be There, removing obstacles, growing their skill set, reviewing their teams, helping them with what they need, help with making sure everyone's aligned. But if you don't have time to do that, that's a good signal that you could leverage that second command. But let me explain what the difference is between a COO and maybe a VP of Operations and a director of operations. If you're telling the person what to do, it tends to be a director level. If you and the person are deciding together what they need to do to get to your goals or to drive the company forward, that's more of a VP level. And if you're hiring somebody who can walk into the organization and they can tell you what needs to get done, they've got budget accountability, they understand the P and L, they understand cash flow. They can really come in with some good strategic insights. They're probably showing up with employees that used to work for them or partners or suppliers they've worked with before that can help your company. They also come in with this level of autonomy that they can just do their job without you having to oversee them. That's truly a CEO or a C level position, whether it's the head of finance, head of marketing, etc. Awesome.

Speaker A: Uh, um, what are decisions that you see business owners avoiding, but they actually,

Speaker B: they should tackle firing people? I think. So many entrepreneurs either haven't developed the muscle that they're good at doing something that's uncomfortable. Right. Good at removing that cultural cancer. Right. If you went to a doctor today and found out from the doctor that you had a cancerous tumor in your lung, you wouldn't leave it there for six months. You, you try to have that thing cut out tomorrow morning. And then so many entrepreneurs find out that Bob isn't doing a great job, or Bob is driving everybody crazy, or Bob doesn't live the core values, but will keep him for six more months or three more months or one more month. Well, Bob is a cultural cancer. So it's these entrepreneurs delaying those tough decisions to get rid of the underperformers or to get rid of the C players. And sometimes it's because they don't know how to do it or they've never really done it before. Often though, it's because they need to be liked. They're still at, uh, that wanting to be appreciated and wanting to be praised and wanting to be liked. Sometimes it's those childhood traumas that the underperforming students who become entrepreneurs, um, you know, really struggled with. Right. So that's what I often see how

Speaker A: do I know if I'm a business owner that's busy or if I'm a business owner that's building?

Speaker B: It's. If you sit down and analyze your work and you were to take a look at the number of hours on all of the projects on your plate this month and this week, and then you could say, are those projects true a priorities? Right? Are they driving revenue? Are they driving gross margin? Are they making my customers happier? Are they making my employees happier? I'm getting a really good return on investment in terms of the hours that I'm doing. Am I getting a big enough lift against all the other things I could be doing, or am I just doing that busy work? So it's doing an ROI analysis on the projects. I often see entrepreneurs spending time running the business because they get no other joy in their life. They have no other hobbies, they have no other passions. You know, I'm in Georgia right now, over in Europe, over near Turkey, if people don't know where Georgia is. And this week I have a cooking course, I have a photo shoot that I'm going on, and I'm playing golf. And I'm only here for seven days. I've already got three activities now I'm going to try and plan a hiking trip, um, on Saturday. So I'm going to try to do four different activities, plus all the sightseeing. I've got seven or eight different coffee shops to go and check out that I've never been to. So I've got. Already got these things in my calendar that will give me joy so that I don't spend time working 12 hours a day because I'm so busy

Speaker A: when. When you.

Speaker B: I mean, by the way, that. That sounds very simple, but I think for so many entrepreneurs, it's a really good gut check. Are you working on critical work or are you simply being busy because you've lost the relationship with yourself and your spouse and your kids and your friends? Right. Is work the only thing that gives you joy? Sorry, M. Simon, I cut you off. Go ahead.

Speaker A: No, uh, I think it's important. I use GTD as a. As a personal productivity method. And it forces me to go through the. They call them horizons, right? Planning horizons. And I have to have projects as a husband, as a father, as a. An athlete, not just as a CEO. I have to go through these projects once per week, and I feel the tendency. Ah. Uh, come, uh, on, let's just work more and go. Wait a moment. What are you avoiding?

Speaker B: Yeah, so I have. I have something Where I look at my, what I call my vivid vision. And I have a vivid vision for me as Cameron Herald and it talks about what I do for fun, what I do for fitness, what I'm doing for vacations. My wife and I, what we're doing for sexual growth, time I'm spending with my kids, what I'm doing for money, what I'm doing for spiritual, spiritual growth. So I have all these areas and I have a full paragraph written about what I look like three years from now. And then I'm constantly figuring out like you are, how do I make every sentence come true. Now what I've come to grips with is you can't have perfect balance. You, every day and every week of the year I almost see you. And I like elephants standing on a teeter totter and we're kind of like an elephant just kind of holding its balance. That's kind of what it's like to manage our wife and our kids and our relationship and our hobbies and our fitness and our finances. So what I try to do is pick a couple of areas that I work really, really hard on. Like last week my wife and I were doing a course in Europe. It was for some sexual exploration and growth that we're working on together. It was uh, an incredible seven day mastermind where we were just together as a couple. I ignored work, I ignored fitness, I ignored spirituality. I was completely immersed in my wife and in our sexual exploration. That was powerful. Well, this week I'm by myself in Georgia, so now I'm going to have some fun and I'm diving deep into work and I'm going to get back to the gym every day this week because I have a gym in the hotel that I'm in. But my wife will slide a little bit this week because I'm not going to see her for 11 days. So it's kind of that balancing act that if you can fall into that, it allows you to feel really good about taking a full week off because now I can have a full week on.

Speaker A: As long as you can trust your system, being it vivid vision or other systems where you know you will pass by and reflect and review and enrich. Right.

Speaker B: Um, well. And what you're talking about with getting things done by David Allen GTD is that you are managing priorities. You're not managing time. And most entrepreneurs, and I actually cover it in my invest in your leaders training. If you go to investinyourleaders.com, one of the 12 management skills or leadership skills is priority Management, and it was something that I was taught 31 years ago. Now, priority management doesn't change. And by the way, you can dump all your tasks and projects into ChatGPT or Gemini or Grok and say, prioritize this for me. It can't because it doesn't truly know your company's goals. It doesn't truly know what metric you're trying to make move forward. So as a leader, as an entrepreneur, you need to understand how do I evaluate every project and every task, which ones are going to give me energy, which ones are going to move one of those metrics forward, and which ones can I delegate to others? And I had a CEO recently that I was coaching and he said, well, I don't have anyone I can delegate it to. And I said, that's too bad. Pick one, pick someone, delegate it to them, and then spend your time growing their skills and growing their confidence and growing their connections so that they can do that ongoing to free you up. And he's like, ah, uh, darn it, I knew you kind of knew you were going to say that. So that that's what we need to focus on more as entrepreneurs. And you're trained in IT because you followed the, uh, GCD system. But everybody managing people needs to get trained in priority management.

Speaker A: And it's true that AI cannot do proper project management because the one thing it cannot do is what's the next action? So that's the missing piece. And if you don't have that, there is no execution. And the second thing is usually it doesn't know your whole company. So what we started doing is to build an ontology like Palantir does, where you have an actual full digital twin of your company in a digital way, including the goals, the monthly goals and the projects and priorities. It still is at 85% because it cannot pick the next action. But an 85% project manager is pretty good for tiny teams, you know, and

Speaker B: what you just, what you just identified is something I've been talking with all of our COO alliance members a lot recently and that's AI is a really good tool to produce really good work that still needs some human oversight to ensure that it's accurate and important. Because you could ask AI to produce a report of a meeting that you're in and it could come back with this great elegant four page PDF that's all perfectly laid out. But the reality is there were only three one sentence bullet points that everyone leaving the meeting needed to be reminded of. They didn't need the four pages. So if you let AI produce all of the reports and all of the work for you, sometimes it's actually not what you're looking for or it's more than you actually need. And AI can often expand not because it's doing anything wrong, but because it's so good at producing content, it can actually make people busier versus more productive.

Speaker A: You, you run masterminds, you run programs. You, you also visit, uh, Masterminds as a learner. What are some masterminds, yours or other people's, that you have found particularly alive and fun recently?

Speaker B: I did a video about this around two months ago on my YouTube channel. And I think it was loosely titled something like, I spent a million dollars on Mastermind so you don't have to. But I made a list and there's no exaggeration, and that does not include travel. I was a member of the Entrepreneurs Organization, which is called eo for five years. I was a member of the Genius Network for nine years. I was a member of Strategic Coach for seven years. I was a member of Mastermind Talks for five years. I'm going to my sixth Baby Bathwater event in October. Um, I've been to two War Room events. I'm going to a, uh, Four Rooms event with Amber Spears in November. I'm going to a Tony Robbins. Eventually. I just came back from one called Landmark. I've been to four Way Finders events. I've been at lots, and these are all 10 to $25,000 events. I went to the main 5 day TED conference for 11 years. So I've spent over $1 million on mastermind attendance fees plus my travel costs over 30 years. It depends on what you're trying to get better at. So it's hard to say which is the right Mastermind because it depends on what you're trying to learn. It's like if I said to you, do you need a coach? You'd be like, yes, I need a coach. And I send over a business coach to you and you're like, oh, I needed a golf coach or I needed a relationship coach, or I needed a mindset coach and I sent a strategy coach, right? So you need to know where you're going. Eo, the Entrepreneurs Organization is a very good global network of entrepreneurs where you end up with a small peer group in your local city. That's a great place to start, as is Vistage if you're in North America. I think the Genius Network, who is a big partner for the CEO alliance, is a premier entrepreneurial Mastermind. With members from all over the world. Joe Polish is the founder of the Genius Network. I would join that for sure. And, uh, then I love Baby Bathwater because of the entrepreneurial component to it, but because of the fun and social component. And they have it at these great locations all over the world every year.

Speaker A: What are you currently working on? What excites you right now?

Speaker B: What excites me right now? Um, well, the work that my wife and I are doing just to continue to grow our relationship has been really powerful. Um, I'm. Are you talking in the business landscape? I would say what I'm working on there is just getting the final people onto my bus. We've built it, a very, very strong team over the last two years. And we have one more person that we're bringing on over the next month and I think then we're got completion on any hiring for the next year or two. So I'm really excited now about aligning everyone and scaling. I'm, uh, excited to go to Brazil next month for the first time. I've never been to Brazil. I have six employees now in Brazil. So my employees from Rio and Sao Paulo are going to fly in and we're all going to spend a couple days together and they're all excited to have me coming down to Brazil. So looking forward to that.

Speaker A: Awesome. Um, where can people find the CEO programs that you run?

Speaker B: Yeah, if you go to cooalliance.com and then also my main website, Cameron herald.com has links to all seven of my books, my podcast, my YouTube channels, my course seal lines. It's all set up in a very organized fashion@cameron herald.com.

Speaker A: awesome. Cameron, did I forget to ask anything?

Speaker B: No. But I'll leave you with one final point that I tell everybody. And I got this tattoo, um, a year ago in, in Italy. The. It's in. Well, it's actually in Hindi.

Speaker A: Oh, Hindi.

Speaker B: And it's, uh, it's the. The quote from Ram Dass that says walking each other home. And it's a reminder that none of this actually matters. We're just taking care of each other until we die, until we go to the next place. And I just want everybody to enjoy the journey, to remember that everybody's struggling with something and we can be there to support them and love them, whether they're employees or co workers or people we bump into day to day. Everybody is struggling with that human condition and we're just walking each other home. So enjoy the journey and take care of each other as we do.

Speaker A: Cameron Herald. Everyone Thanks, Cameron, for being on the show, sharing your wisdom, your journey with us. Enjoy, Georgia and I'm excited when we talk the next time.

Speaker B: Appreciate it. Thank m you so much.