How to Stop Being the Bottleneck in Your Business with Cameron Herold

Cameron Herold – COO Alliance (00:00)

I’m also willing to work with people to kind of shake them a little bit and say like, you know, let’s have some fun. Let’s build a better life. You know, let’s get on with some of those hobbies that you should be doing. And I think when I do that, like I just coach somebody recently to take their first vacation in seven years. I’m like, why are you building a business that’s handcuffed you to the business? It sounds like if that was a job, you would hate your job, right? If your boss doesn’t let you take enough time to have a vacation, but if you’re the boss and you’re running the company, why are you

building such a crappy company that you can’t take time off.

Michelle Kesil (02:03)

Hey everybody, welcome to the Real Estate Pros Podcast. I’m your host, Michelle Kesil, and today I’m joined by someone I’m looking forward to chatting with, Cameron Herold of COO Alliance, helping entrepreneurs grow their business and their leadership skills. So, excited to have you here today, Cameron.

Cameron Herold – COO Alliance (02:23)

Thanks, Michelle. Appreciate it. Looking forward to it.

Michelle Kesil (02:24)

Perfect, so let’s dive in. First off, for those not familiar with you and your work, can you share what your main focus is?

Cameron Herold – COO Alliance (02:32)

Sure, my core focus right now, I guess, would be twofold. One is I have a large mastermind community, global membership. We’ve got members from 17 countries, and it’s exclusively for the second in command to the entrepreneur. So it’s called the COO Alliance. There’s so many groups of masterminds for the entrepreneur, I really started one for their second in command. And then the second thing that I have is an online training program called Invest in Your Leaders that is the 12 core leadership skills that any

when managing people needs to get trained in and most of us have had no exposure to. So growing both of those are really my core focuses today.

Michelle Kesil (03:08)

Awesome. And what led you to create these offers?

Cameron Herold – COO Alliance (03:12)

One was just kind of listening to the market. was coaching a couple of entrepreneurs 10 years ago and they were mid-sized companies. They were both doing around 30 or 40 million in revenue. They had about 150 employees each and their COOs were also people that I was coaching. So I was coaching the entrepreneur and the second in command and one of the COOs, Zach Morrison, that he would love to chat with some of the other COOs that I coached and I said, I don’t really coach any COOs and he laughed and he said, well, you’re

you’re

coaching Matt Wool at Acceleration Partners and you’re coaching Zach Oberon over at Book in a Box. I’m like, well, how do you know my other COOs that I coach? He goes, you mentioned their companies and I just looked them up. so why don’t you just get a group of us together? So we pulled 10 COOs together for three days. They all paid $7,000 to come and meet for three days. And at the end of the three days, nine of the 10 wanted to continue meeting. So I was just like, well, if there’s that much demand in the market for this kind of a service, let’s kind of create.

that and that was where we just scaled up from there. So now as I mentioned we’ve got members from 17 countries, 40 % of our members are women, so just really listening to the demand in the market.

Michelle Kesil (04:19)

Awesome. And what do you see as some of the biggest obstacles that these entrepreneurs face?

Cameron Herold – COO Alliance (04:29)

One is really around focus. think so many entrepreneurs feel overwhelmed. They just have so much on their plate. They have so many opportunities. They have so many ideas. They have so many people pulling them in different directions. That’s one big one. I think another is just the overwhelm. There’s so much change happening and so much coming at them so quickly that there’s a big sense of overwhelm within the entrepreneurial community, especially as it relates to AI. We’ve just spent really the last 24 months with people being bombarded with, try this AI

and use this AI tool and put this deep into your company. And that’s in addition to the day-to-day of just running their business. So think there’s a real feeling of overwhelm in that entrepreneurial community. And then lastly, there’s a real feeling of uncertainty right now. You we’re dealing with tariffs, we’re dealing with wars in the Ukraine and wars over in Iran, and we’re dealing with, you know, AI obliterating the employee sector, and we’ve got some inflation, and then we’ve got a potential recession. There’s a lot of uncertainty in the entrepreneurial market right now that I think has the weight on.

on the entrepreneurial group for sure.

Michelle Kesil (06:19)

Yeah, absolutely. And what does the process look like when you are working with someone?

Cameron Herold – COO Alliance (06:26)

When I’m working with them, we look for typically a mid-sized company in the five to $50 million range as a starting point. They usually have to have already got a good management team in place. And then I work with them and do one-on-one meetings over the course of a year to start. Some of them continue on for two or three years, but I do one-on-one coaching calls with them. We do one call a month for 90 minutes. And then I have a group call with all of my other coaching clients at the same time. So they get to hear a little bit of the wisdom of the crowd. They’ll ask a question and other CEOs.

that I coach or COOs that I coach will answer. You one of my coaching clients as an example is the COO of ButcherBox. So they’re about a $600 million company, a brand that most people have heard of, and I’ve been coaching their COO now for about 16 months. So I work with her on holding her accountable, sometimes holding up a mirror so she can see that she’s a part of the problem. Sometimes it’s brainstorming, sometimes it’s a bit of a kick in the ass, but I’m really there as a mentor who has been through a lot of these struggles in the past.

and sharing my experience. That tends to be the core.

Michelle Kesil (07:28)

Yeah. And what do you feel are some of the main keys that have allowed your business to grow and run successfully?

Cameron Herold – COO Alliance (07:35)

One right now related to the CEO Alliance is just that we’re in a bit of a blue ocean, right? We’re in a market that does not have a lot ⁓ of people competing, right? If you think about the entrepreneurial world, we’ve got, you know, Core and the Genius Network and Vistage and YPO and Breakthrough Academy and EO and, you know, Maverick and GoBundance and like there’s so many groups of entrepreneurs out there, but then there was really nowhere for that second in command. So in starting a community,

that didn’t have anything really in place, but that the CEO understood the value of masterminds. It’s almost like working with a husband and wife in a traditional marriage. If the wife is getting coached or is working on her health, she talks to her husband and goes, hey, you should be working on your health and working on your mindset or whatever. It’s an easy crossover. It’s very hard to sell to one person who’s never had any exposure or experience. So what we’re noticing is a

lot of CEOs that are in mastermind communities are very open to and in fact very keen on getting their second in command to join us.

Michelle Kesil (08:41)

Yeah, absolutely. And when you’re coaching entrepreneurs, what kind of mindset blocks are you mostly working through?

Cameron Herold – COO Alliance (09:28)

Well, one of them is that kind of fear about what’s happening in the market. Another one is just really sitting down and looking at them and finding out where their mental blocks are around growth. And I often hear them making excuses. You know, I don’t have anyone to delegate that to, or there’s just not enough hours in the day, or I’m the only person that could possibly do this. And what I tend to push back on is that’s not actually true. You know, I’ve heard these excuses so many times from so many different people that it’s almost the same stuff different days.

scenario, so when I can hold up a mirror and show them a different way to look at that, I also show them that delegating and taking time off and getting out of your business is a better way to scale the company. I think a lot of entrepreneurs are dissatisfied with their relationships, they’re dissatisfied with their health, they’re not super happy with themselves, they don’t really have a lot of hobbies, so that the only way that they really feel good

is by running their business. That’s where they get their dopamine rush. And it’s a very unhealthy relationship. It’s also very kind of a North American kind of phenomenon to say things like, well, business is my hobby. We’ve been traveling around the world for the last five years. I’ve been to about 80 countries in the last five years. And you just notice that people in the rest of the world have hobbies, or they have friends and family. And that’s what they’re obsessed about. Business is what they do to make money, but it’s not their hobby. And then I joke with entrepreneurs.

and say, if business is your hobby, do you like hearing accountants talk about accounting? Or do like hearing lawyers talk about law or dentists talk about dentistry? Like, no, we don’t like hearing about any other industry talk about their work as their hobby because it’s not. I think entrepreneurs are often on tilt and I try to get them to realize that so that if they take time off and if they have hobbies and if they spend time away from the business, it forces them to delegate more. It forces them to grow their people. It forces them

to put systems and skills in place to really scale up those people. ⁓ So that’s sometimes what they’re missing is that blind spot.

Michelle Kesil (11:30)

Yeah, definitely that’s a big one.

Cameron Herold – COO Alliance (11:32)

You know, I didn’t even realize that in the COO world, that often the COOs are very lonely in their role.

We knew that entrepreneurs were lonely because they can’t really tell their board, they can’t tell their employees that they’re scared, they can’t tell the leadership team that they’re frustrated or worried. Sometimes they don’t even tell their spouse because they don’t want to freak their family out. So they live in this very scary bubble. Well, the COO is going through that as well, right? They can’t really tell the entrepreneurial CEO that they’re scared or overwhelmed or don’t know what’s going on because they feel like they’re putting their job at risk. And most of their friends don’t really understand the pressure that they’re feeling running some

else’s company. So it tends to be a and then the other part is that every year or every six months as you grow the company it’s now bigger than anything you’ve ever run in the past. So like your your role just keeps changing and evolving and adopting and needing to change too.

Michelle Kesil (12:23)

Definitely and what are you most focused on solving or scaling to next?

Cameron Herold – COO Alliance (12:29)

I’m looking at scaling to just have a really good global reach with the organization. I think we have a lot more opportunity to learn from and work with and connect with entrepreneurs in the Middle East and in Europe and in Asia. So working to grow those markets for the CEO Alliance. Also working to bring on better and better speakers. So we’re working getting in some really, really strong experts into our monthly mastermind calls. Those would probably be the core focuses right now.

Michelle Kesil (12:54)

and besides the COO Alliance, are there any other opportunities or ventures that you’re currently involved in working in?

Cameron Herold – COO Alliance (13:03)

Not really, no. mean, it’s the CEO Alliance is the core business and then the coaching of these entrepreneurs. And then I’m still paid to do speaking events all over the world. I just spoke last month in Austria. I’m speaking next week over in Scottsdale, Arizona. In January, I spoke down in Mexico. So I’m still paid to go around the world to speak to these entrepreneurial audiences. And I still love doing that. I also really enjoying spending time with my kids. I’ve got a 25 year old and a 23 year old boy and love spending time with my wife. And so we’re doing a lot of

know growth and travel and and we’re calling it our bucket list life. Just exploring our bucket list activities

Michelle Kesil (14:17)

What are some of the core topics that you speak on?

Cameron Herold – COO Alliance (14:21)

I talk about leadership, I talk about culture, I talk about getting results through people and growing people. I kind of bring in some of the expertise around the CEO, COO relationship. What I’m very well known for is building these world-class company cultures. When we built 1-800-GOT-Junk, we ranked as the number two company in all of Canada to work for. So I got known, and then I’ve coached a number of companies globally that were number one in their countries or number one in their state to work for.

So that kind of exposure and experience is stuff that I bring into my speaking and bring into my coaching. And then I’m also really working with people.

Michelle Kesil (14:53)

And what do you,

yeah.

Cameron Herold – COO Alliance (14:55)

I’m also willing to work with people to kind of shake them a little bit and say like, you know, let’s have some fun. Let’s build a better life. You know, let’s get on with some of those hobbies that you should be doing. And I think when I do that, like I just coach somebody recently to take their first vacation in seven years. I’m like, why are you building a business that’s handcuffed you to the business? It sounds like if that was a job, you would hate your job, right? If your boss doesn’t let you take enough time to have a vacation, but if you’re the boss and you’re running the company, why are you

building such a crappy company that you can’t take time off.

So sometimes just pushing them in that direction and then when they take the vacation they end up delegating more and growing their people more and that ends up building a better company. It’s almost like by being a little bit out of the office more and enjoying your life more everything grows more.

Michelle Kesil (15:40)

Absolutely, that’s so important. And what do you think are some pillars of a company that has a strong culture?

Cameron Herold – COO Alliance (15:48)

Well, one is an alignment with core values. Another is an alignment with vision. Another is that greater purpose. with Elon, it’s right now it’s colonizing Mars. With Google, it was democratizing the world’s information. So with 1-800-GOT-JUNK, it was building a globally admired brand. For me right now, it’s replacing vision statements with vivid visions worldwide. So it’s always having a greater purpose and then a deep obsession with your core values. Because A, players don’t like working with jerks.

A players only want to work with really, really smart people. So it’s kind of helping companies understand that stuff. The media has talked about perks like free massages or free meals. That’s not culture. Those are merely perks.

Michelle Kesil (16:35)

Yeah, absolutely. And what do you think makes a leadership team stand out?

Cameron Herold – COO Alliance (16:46)

Well, the ability to have really good debate, the ability to talk about our facts and feelings and also look at the data. I think sometimes when leadership teams are only looking at the data and they ignore their intuition or they ignore feelings or they ignore what they’re seeing, that can be to their detriment. And then vice versa, leadership teams that are only talking about facts and feelings but don’t look at the data. So one is that ability to have really good, healthy debate. And then looking for leadership team people that already live with the core values of the organization, right?

show up day to day because those core values are already important to them in their daily lives.

Michelle Kesil (17:20)

Yeah, absolutely. And so what is a way that some of these CEOs or other entrepreneurs end up having more success from these shifts?

Cameron Herold – COO Alliance (17:35)

Well, one is that they end up, the more that they delegate, the more that they’ve kind of increased their free time and the more that they’re able to work in their area of unique ability. Right? I think that most leaders have two or three things that they’re really, really good at and they really love doing. And then they end up spending a lot of time doing other stuff that maybe drains them of energy or they’re just not amazing at. So the more that they delegate and the more that they get off their plate, the more that they show up with great energy and they’re working on cool stuff and they’re really fulfilled.

and they’re working shorter days, and then because they’re delegating more, everything just kind of grows. So they tend to double their revenue, they double their profit, and they double their amount of free time quite quickly by building a better brand, building a better company.

Michelle Kesil (18:18)

Yeah, absolutely, that’s amazing.

Well, before we begin, to wrap up here, if someone wants to reach out, connect, and learn more, where can people find you?

Cameron Herold – COO Alliance (18:29)

The best place would be the Cameron Herold website. So it’s Cameron, and then H-E-R-O-L-D, so cameronherold.com That has links to my online course, Invest in Your Leaders, has links to my Second Command podcast, all of my books. It’s all set up like a link tree. So cameronherold.com would be the easiest place to go.

Michelle Kesil (18:46)

Perfect. We’ll appreciate your time and your story. Thank you for being here.

Cameron Herold – COO Alliance (18:50)

Of course, thanks Michelle, appreciate you having me.

Michelle Kesil (18:52)

And for those tuning in, you got value, make sure you’ve subscribed. We’ve got more conversations with operators like Cameron who are building real businesses and we’ll see you on our next episode.