Ep. 199 – Boldheart COO/Fractional Integrator, Derek Fredrickson

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Our guest today is COO Alliance Member Derek Fredrickson, COO and Fractional Integrator of Boldheart.

Derek is responsible for overseeing and managing all aspects of the day-to-day operations of Boldheart, focusing on business development, planning, strategy, and team.

Derek is an expert in business operations, team building, systems, and marketing.

Derek’s down-to-earth leadership style allows him to effectively lead, manage and keep accountable a virtual team of 25+ individuals, while efficiently focusing on exponential growth activities that allow the business to scale and expand.

When he’s not “running the show” at Boldheart, he can be found skiing in the Alps, drinking French red wine (Médoc being his favorite), listening to house music, vying for a way to play more tennis, and spending time in Paris with his wife Fabienne and their three awesome kids.

In addition, Derek serves as a COO/Integrator for other entrepreneurial clients – supporting them and their vision into reality!

In This Conversation We Discuss:

• How Derek divides his time between multiple brands as a COO & fractional integrator
• How to set up boundaries and proper communication systems when your CEO is your spouse 
• The role KOLBE profiles play in finding a cultural fit for your company 
• The role of a fractional COO and its core responsibilities   

Resources:

Connect with Derek Fredrickson: LinkedIn 

Boldheart – https://boldheart.com

Connect with Cameron: Website | LinkedIn

Get Cameron’s latest book “Meetings Suck: Turning One of The Most Loathed Elements of Business into One of the Most Valuable

Get Cameron’s online course – Invest In Your Leaders

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Our guest is COO Alliance member, Derek Fredrickson, COO and Fractional Integrator of Boldheart. Derek is responsible for overseeing and managing all aspects of the day-to-day operations of Boldheart, focusing on business development, planning, strategy, and team. Derek is an expert in business operations, team building, systems, and marketing. Derek’s down-to-earth leadership style allows him to effectively lead and manage and keep accountable a virtual team of 25-plus individuals while efficiently focusing on exponential growth activities that allow the business to scale and expand.

When he’s not running the show at Boldheart, he can be found skiing in the Alps, drinking French red wine, Médoc being his favorite, listening to house music, vying for a way to play more tennis, and spending time in Paris with his wife, Fabienne and their three awesome kids. In addition, Derek serves as the COO-Integrator for other entrepreneurial clients, supporting them and their vision into reality. Derek, welcome to the Second in Command show.

Thank you so much, Cameron. It’s great to be here.

I’m curious how you actually divide your time between multiple brands and acting as that second-in-command for them. Then, we’ll bounce around a little bit from there. Can you talk to us about that, how you balance your time?

It’s been an evolution because in the beginning I was focused solely just on Boldheart, and that’s the business that I’ve been working on with my wife, Fabienne, for the last ten-plus years. As that business has scaled and leveraged over the last few years, it’s allowed me to free up my time more to focus on doing the Integrator-COO work for some other clients. I have two clients here in France and another client in the US, as well as the Boldheart team, which is based in the US.

Luckily, me living in France I can focus my mornings a bit on the French clients and working with their team and working with the visionary CEO and the founder and helping them with that. Usually, my afternoon is more focused on the work that I do with my US clients. I’m very diligent about my time, so I’m very structured as most COOs would have to be in terms of, “I’ve got my day’s calendar out. I’ve got my time meticulously planned and organized so I know exactly what I’m doing and where I’m doing it.” That’s part of, I think, why I’ve been successful in the role is being able to be very organized and planned out in that way.

Also, just having boundaries. I don’t work on the nights and weekends. I’m very cognizant of the fact that at 6:00 or 7:00 my time, it’s 12:00 or 1:00 on the East Coast. If you’re having lunch where you are in America and you need to talk to Derek, it’s dinner time. It’s going to have to wait until the next day. It gives me an opportunity to create some more boundaries of how I work with my team and how we communicate and collaborate in that regard.

I’ve got a bunch of questions I want to ask about this too. Just for clarity as well, the CEO of your company is Fabienne, your wife?

Yes, correct. That’s right.

When did you join her and come on board as the COO? How does that relationship work?

How much time do we have? My background is in Wall Street Project Management. That’s what I had done before I joined the entrepreneurial world. I did that in 2008 just before the whole financial crisis meltdown and everything else. My wife had grown at that time a company called Client Attraction to a very successful first time at the seven-figure mark. As she said, it was mostly built on toothpicks and Band-aids.

When I came in, I brought a lot of that structure, that process mindset into how we were going to build and scale the company even more. Through that work of leveraging the company and building the team and finding the right people in the right seats and developing processes and systems and more efficiencies and everything else, we were able to grow and scale the business more and more.

At that time, it was the first time obviously that we had worked together. She did a lot of the client-facing, the marketing, the sales, the delivery. I was focused more on the operation side, backstage versus front stage, managing the team, managing the processes, managing the projects, the plans, the P&L, and everything else.

Nobody else in that industry was working in a husband and wife capacity in that way, or at least working well where they could share a lot of best practices. We were figuring it out as we were doing it. Full transparency, there was some conflict. There were some challenges around the ways she wanted to run the company and some ideas and discussions that I had around how the company should evolve.

It’s a great thing when you have a partnership like a husband and wife that are in business together when they’re fully aligned, but it’s sometimes hard to get there, and we were able to do that over the last many years. Part of that is just very clear on what her role is as the CEO and the founder and the visionary, and very clear on what my role is as the COO and Integrator and respecting each other’s differences and strengths, and understanding and playing that more and more to our advantage and not trying to blur the lines.

I don’t want to try to be the visionary, nor does she want to try to be the COO. If we allow people to stay in their brilliance of what they should be doing to move the business forward, and we don’t let the ego get involved, we don’t let personal matters get involved or anything else, then that’s been the real magic sauce for us.

That’s really one of the keys to the CEO-COO relationship as well. I’m working on a book on that that’s going to come out. The magic or the art, I guess, of staying in your own lane and not trying to become the visionary. How do you do that when you’re also married to the person and you’re around the vision and excitement of that entrepreneur all the time? How do you not get caught up in that? How do you allow yourself to just stay where you are and vice versa?

There are times when we do get together. We tell the story that we have different hats. I might have the husband hat. I might have my COO hat. Also, at times I have the co-business owner hat. At the end of the day, it’s our business in the sense that because we’re married and we live together and work together and have a family together, it’s our business. It’s also very much her vision. She’s the one that created the company. She’s the one that built it to that level.

I know that without her being the visionary, if I tried to be the visionary to get it to the next level, I wouldn’t be able to do that. That’s not my skillset and that’s not my strength. I know that when I put my best foot forward to be the COO, it’s the way that I can actually help move the business the furthest. At the same time, we have those conversations as husband and wife and say, “What do you think?” It gives us that advantage, but we have to be careful because if we blur the lines, sometimes it can bite us.

It’s so interesting because that’s exactly the setup that we had with Brian and myself when we were building 1-800-GOT-JUNK. I came in as the fourteenth employee, and I had certain ideas for the business, but I really defaulted on the vision to him, then he really just let me figure out the how. I don’t think we realized until much later until we got to the $100 million mark how well we had allowed each other to stay in their lanes. I didn’t take anything personally that it was his vision because I joined him. It was his company. I also wasn’t married to him, although people called us. They thought we were.

I love what you said, Cameron, about staying in the lane, but also if you put the best interest of the company first, as opposed to your own personal interest or your own personal motivation or ego. If I look at my role in the company or Fabienne’s role in the company as an asset, as something that I can leverage in order to get a higher return on that investment of that asset. I just had this conversation with her. We did a planning session with some of our core leadership team, and Fabienne and I were doing that together.

Fractional Integrator: Look at your role in the company as an asset, as something that you can leverage in order to get a higher return on that investment asset.

What we realized is that for her to add the most value, she has to stay in that visionary box. She has to be in that CEO seat. When she starts to move over into something else, not only does it drain her energy, which deflates her and demotivates her in some way, it can then complicate things. I know the exact same thing. If I’m trying to create the vision and say, “Here’s where we’re going to go and here’s how we’re going to get there.” I need that from her, but we can do that together because we’re husband and wife. Because we’ve been able to do that, I think it’s allowed us to then have the business run almost like as a self-managing company, and allow us to explore other interests that really fit for what she wants to do as the visionary and what I want to do serving now other clients as their COO as well.

How do you make sure that you don’t let the business interfere in your life? I know you said you don’t like working on nights, you don’t work on weekends. How do you make sure that every meal you’re out with her, when you’re on date night or when you’re just hanging out doing whatever on weekends, that you don’t talk about business because it’s on your mind and it could be on hers? How do you separate that?

I have to 100%. In the beginning, full transparency, it was not easy. I could tell you so many different stories. I remember a Sunday morning, we were at the playground with the kids and I just happened to be looking at my phone. I got some email that was something related to work, and I think I mentioned something to her. It just shot the weekend from that one moment of interrupting what was a personal matter to something that was business related. If I wasn’t working with her and somebody else who was the CEO got that email, they wouldn’t have shared it in another way. I have to be very careful to not necessarily blur the lines in that way, and sometimes with her as well.

As the visionary, sometimes we’ll be talking about things. We’re just talking, we’re not getting into tactics. We’re not talking about implementing anything. As Fabienne will say, “I’m just throwing some spaghetti at the wall to see what sticks. I’m talking to my husband. I’m not talking to my COO.” I’ll say some things in the same way which is, “I’m talking to you as my partner, as my wife, not as I would talk about what my day was like, what your day was like.“ You have to have some reality sense in that way.

The other thing I’ll share, which is a hack, which is very important especially for the two of us because it relates to boundaries and communication. We have text messages and WhatsApp, and we use Slack for our company and everything else. I never do anything that’s personal on Slack, which we use for business, and I never do anything that’s business related on WhatsApp or text. I’ll never send her a WhatsApp and say, “Did you talk about the blah, blah, blah regarding the team launch or something like that?” Because that’s my sacred space, that’s personal. I do that with everything.

The same, I will never say something, or even a team Zoom or on Slack and refer to her as my wife. I refer to her as the visionary or the founder, and my role as the Integrator-COO because we try not to blur those lines. When we blur the lines, it complicates things. It creates more complexity. It adds confusion. You can then find yourself sitting at the restaurant and talking about work, and you’re in a rabbit hole like, “Where did the hour go? We’re supposed to connect, just the two of us. What is this? It’s a date night.” We have to respect those boundaries.

I remember when my brother started working with my dad’s company. My brother would call my dad when they were at the office, he would call him John. Later in the same day, they’d be at the golf course and he’d call him dad. He was able to intertwine that, “Dad, grab me my putter. John, can we work on this?” It was so weird to hear it. You used a term, backstage-front stage. Were you part of The Strategic Coach Program at some point?

Yes, for about 5, 6 years.

That’s a term that Dan Sullivan has talked a lot about where the front stage is usually the actor, the CEO, and then backstage is the operational, IT infrastructure side of things. Is that part of how you run the business as well, delineating roles front stage, backstage?

Yeah, for sure. Again, once I got really clear that the best way to tap the value of what we can both do in the company was for her to be in that front stage role and for me to be in that backstage role, it’s what I enjoy to do. Obviously, her as the visionary, the founder, she enjoys that front stage role very much. There were points in the beginning where I had my ego get in the way. I was still new to this and thinking, “Maybe I should do a launch. Maybe I should do an event. Maybe I should sell a product.” I realized I’d done that, but then I really felt like where I could add the most value was doing everything I wanted to be doing backstage, behind the scenes. I don’t necessarily need the accolades. I don’t need the star view in that regard. It’s what I enjoy doing.

I could be front stage to my backstage people. That’s where I like to show up. I can lead them, I can manage them, I can hold them accountable, I can inspire them. I did a team video, I do it once a week where it’s a state of the union, “Here’s where we are, here’s where we’re going, here’s how we’re going to get there.” I do a Loom, it’s about 30 minutes. I know, just in the same way that Fabienne does that for her clients, I’m doing that for my team so that they feel on board, they feel inspired, they know what their part is going to be. I have a front-stage aspect to my backstage role, but I enjoy doing that the most, for sure.

I love that example. To complete my thought on the Dan Sullivan component with backstage-front stage, when I first heard him talk about it back in the late ‘90s, early 2000s, he was talking about Phantom of the Opera as the theater production in New York. He said, “There are only ever 3 or 4 people on stage at Phantom of the Opera. Those are the actors, the performers, but the backstage that makes that happen are the set designers, the costume, the lighting, the people selling tickets and marketing and selling you the popcorn. Without all those people, the show would never happen. It didn’t matter how great the actors were without the backstage, and it didn’t matter how great the backstage were without the front stage.” I was like, “That makes so much sense.”

If you’re the person in charge of all of the costume people, you’re the leader of the costume group. You’re front stage at the back stage. That’s a cool way to look at it. You said something about there weren’t a lot of examples of couples working together. There was an organization in Canada called CAFE, which is the Canadian Association of Family Enterprise. It’s an organization that focuses on couples and multi-generational family businesses. Did you ever find any resources that you turn to or did you just talk and work through stuff and hodge it together from stuff like Strategic Coach, etc.?

It was mostly that. We got a lot of insights when we were in Strategic Coach because we were in that together. I remember one of the first few meetings that we had with Dan. We were in the room with 30 or 40 different entrepreneurs. It’s designed for the visionaries. It’s designed for the CEOs, the founders. I was there with Fabienne and having the same conversation around, “Where do we want to take the business? What’s going to help us get there?”

When we started to do some assessments and we started to get really get clear on things like unique ability, that’s where it started to shed a light on how do we do more of what we are really naturally gifted at. The things that are going to, again, add the most value to the company. You know about Kolbe, right?

Yes. I was just about to ask you. Go ahead.

I have a Kolbe that is not like anybody else in Strategic Coach because I am wired to focus on backstage. I remember I had this insight because I was walking around. You know how in Coach, they sell different resources like books and everything else. I went up to the back of the team and everybody has their Kolbe printed on their name badge. I had a Kolbe, the exact same Kolbe score as somebody that was working at the back of the room selling books at the table.

What’s your number, your Kolbe profile?

I’m an 8814.

I’ll explain that in a second for everybody. What’s Fabienne’s?

She’s a 7672. It’s not that far off, but as you know with Kolbe, there’s a big difference when you get to 8, 9, and 10 versus 5, 6, 7. I’m obviously long fact finder, a long follow-through.

I’m a 4393. For people that are reading, the first number is fact finder. That means that you initiate projects by asking a lot of questions. In layman’s terms, I’ve always said the higher your number, the more questions you’ll ask before you’ll start a project. You might ask eight questions to start a project. I have a four as a first number, so sometimes I don’t even ask questions to start a project.

You just go right to it.

The second number is called follow-through. I’ve actually talked to David Kolbe and Kathy Kolbe about that, I think it’s misnamed. It should be called the systemizer or the planner because it’s more about putting a playbook or a plan or a system or a checklist in place before you’ll start a project. You’ve got another eight. For you initiating projects, you ask questions, you put a system in place and then you go.

Fabienne’s is interesting because with her, the 7672, her third number is 7, which is higher and her first number is higher. That’s interesting. That’s not traditionally very entrepreneurial. That’s someone who’s really strong usually around working on corporate reorganizations, maybe working on understanding corporate, and then giving them plans to execute on. What’s the business of Boldheart? What do you guys do?

Business coaching. We help entrepreneurs basically scale and leverage their business. I’ll say what’s interesting is where there was some conflict was in the quick start, the third number, initiating ideas, coming up with improvising and risk tolerance. I’m a 1, she’s a 7. Whenever you have a difference of three or more, it’s like oil and water where there can be some healthy conflict. Before this, we didn’t know. We didn’t know why she was wired to want to throw spaghetti at the wall to see what sticks, and I’m here capturing ideas and thinking I’ve got to implement all of these with a team that’s already got 110 things on their plate like, “This isn’t going to work.” That’s where the conflict came from.

When I realized she’s a high idea generator, likes to start things, doesn’t necessarily always finish them, but she’s got a systems-oriented mindset, but I’m wired for systems. You give me a process or a system to implement, I’ll do that eight hours a day. That’s where the 8 fact-finder and 8 follow-through. That was an interesting insight I had at Strategic Coach. What I realized is that I can serve entrepreneurs and visionaries and CEOs at that strategic level being an 8814, that’s where there’s a lot of magic that happens. There was a big insight I had when I experienced that.

For anyone who has a high first two numbers dealing with an entrepreneurial CEO, there are two tricks that I’ll give you that will help you. When the entrepreneur comes to you with the idea, the first thing that we, as COOs, are supposed to say is, “I love your idea. Let me ask you a bunch of questions so that I can catch up with you.”

Exactly, it’s so true.

As long as they know that we’re going to ask them a bunch of questions but we like their idea, they don’t feel like we’re debating them or arguing with them. Then the second part is to go to the entrepreneur and give them the bottom line first, give them the executive summary, and know that they might ask us questions later, but don’t feel bad if they don’t ask us all the questions. It just means they trust that we’ve already done the questions ourselves.

Exactly, that’s great. I’ll say the other thing. Kolbe was a huge insight when we did StrengthsFinder by Gallup. That was a huge revelation as well to understand not just our five themes, but the five strengths with the themes. You know about StrengthsFinder. Four of my strengths are in executing. When I knew that I’m wired to execute with my strengths, and I’ve got a Kolbe that fits that type of profile, then I was like, “Just let me at it. What are the projects? What are the plans? What are the things that we can get done and help hire a team and train the team and onboard a team that can think like that and execute like that.” It’s how we were able to get so much done in such a short time. Those assessments and having that clarity to understand who we uniquely are and gifted at that, even though they may be completely different, but then being able to step into that was an absolute game changer.

I don’t understand why more companies don’t use these tools in the right way. I don’t tend to use them as much though in the interviewing and hiring process. I tend to use them more once I have the people in the roles, based on the fact that I know they’ve done it before and they’re the right cultural fit. I use it to try to learn how to work better with them. Do you use it in the interviewing and hiring of people as well?

Yes. We have two programs in Boldheart. One is called the Growth Track and one is called the Leverage Track. Our Leverage Track is for members that are making six figures or more. Every single member, when they join part of their intake or onboarding processes is they do their Kolbe and their StrengthsFinder. It’s essential for an entrepreneur to know how they’re wired to take action, their Kolbe and what their strengths are. Obviously, if you teach things like operate from your strengths and delegate your weaknesses, you need to know what your strengths are in order to be able to focus more on your strengths and delegate your weaknesses. That’s a huge part.

In the interview and in the screening process for onboarding team members, I don’t speak to somebody unless I know what their Kolbe and their StrengthsFinder is. Otherwise, I feel I might be having a conversation where they’re trying to sell me for a position or a role where it might end up being a square peg in a round hole. People are very good in selling themselves on LinkedIn, on selling their CV, and selling everything. If I know that I’m hiring, as an example, a bookkeeper, I don’t want somebody to be a low fact finder and a low follow-through and a high quick start. I don’t want somebody to be improvising and coming up with ideas on how to do my P&L. I want them to be fact finder, follow-through, low risk tolerance.

Conversely, if somebody’s in sales, it’s good if you can have some fact finder and you want to do some follow-through, but I want a high quick start because I want that person to be able to improvise, to pivot, to come up with objection handling on the fly. You need to have a high tolerance of risk for somebody to be able to operate in that way. We do use the assessments a lot in the hiring process.

You just touched on something that I’ve laughed about for years, which is that there’s no single great salesperson that will ever make it through an HR screening process. HR people hate salespeople because they’re completely different. HR people are policies and procedures and follow the systems, and they’re a little more calm and more stable. Salespeople are winging it and shooting from the hip and making it up on the fly. They don’t even know there’s a box, let alone the inside of it.

Let’s go back and talk about the multiple brands that you’re working on. I also want to talk a little bit about some of the time boundaries because you’re also operating from Europe. Your day really starts around 1:00 in Europe and can end at 7:00 or 10:00. What does your day look like working from Europe? How do you time block that out so you have a life and so that you’re working with clients?

The mornings are typically my buffer time. The two clients that I have are my French clients. They don’t take that much of my time. Any of the meetings I need to do with them are typically on the morning French time because then it doesn’t compete with my afternoon if I need to be with the team in the US for the two clients I have there. It’s also my buffer time.

I’m a structured guy. I’m using a lot of tools. I’m using Evernote. I’ve got Notion open. I’ve got Asana open. I’m getting really diligent about my plans. I’m getting focused on my activities of what I need to do and set things up for success in that way. After that, when I get into the afternoon, it’s mostly spent with some team, making sure that things are happening the way they need to be happening, checking in if I need to, doing discussions, etc. I also don’t volunteer my time unnecessarily.

Some of my team members think that I’m not the kind of person that wants to get on the Zoom and chat and everything else, but I’m a very busy guy. We’ve all got lots of things going on. If I can do something or get to a result that doesn’t involve spending 30 minutes on Zoom, talking something through that can be done on Asana, that can be done in a 5-minute Loom or on a Slack conversation or anything, I’m more than likely to do that because I’m all about efficiency and effectiveness and how to get the job done. I’m also cognizant that I’ve got 4 clients that I’m juggling that might have different priorities and different schedules and different launches happening. I need to be very diligent about that.

Like I said, Cameron, at the end of the day, first and foremost, none of this would matter unless I put family first. At the end of the day, I’m usually here. It’s 6:40 on a Friday night, and sometimes my son will come in from school and grab his computer. Then, we’re going to set up a dinner here in a little bit and everything else, and I have to honor and respect that. Otherwise, if it’s all work all the time, then I can’t show up and give the best value that I can to my clients.

I’m very cognizant that mornings are great buffer time, thinking time. Afternoons can be a bit busy, but I structure it so I’m not double booked. I’m not spinning my wheels until 8:00, 9:00, 10:00 at night and saying, “I’ve got to spend this time on Saturday afternoon and do all this work.” When my computer’s done here, when we’re done, I will not touch things until Monday morning.

I guess you’re lucky in Europe as well that they don’t start eating dinner until 10:00 or 8:00 at night.

Exactly, it’s a bit late here.

Have you adopted that schedule or are you still more North American like 6:00 PM dinners?

No, it’s later. We had dinner about 8:30 or so. It was an adjustment for everybody, but that’s part of the culture here. You tend to have your meals later and longer. I’ve seen you travel in Italy and other places. Saturday lunch here is sacred. It’s a multi-hour event every single Saturday. It’s not grab-a-sandwich-and-walk-down-the-street. It’s several courses with cheese, with wine, very good, fresh ingredients and products. Luckily, my wife is a fantastic cook, so she loves to cook and entertain, so I get the benefit of both worlds.

I want to go back to the term fractional. What is a fractional COO meaning for you?

Fractional COO for me is the concept of the COO in all sense of the word, being able to support the visionary, first and foremost, and support the founder, provide that structure, leading, managing and holding people, plans and projects accountable. That’s my mantra. That’s what I think of when I think of COO. They’re looking at plans, they’re looking at P&L, they’re looking at the big picture vision from the visionary and then making it happen.

Fractional Integrator: The concept of the COO, in the all sense of the word, is being able to support the visionary and support the founder. Provide structures, leading, managing and holding people, plans, and projects accountable.

You know this from Strategic Coach, and it was a game-changer when Dan first said it, is that the visionary makes it up. Somebody like the COO makes it real and then the team makes it occur. My role is making it real and then making sure the team continues to execute it and then occurs on an ongoing consistent basis. For me, it’s supporting the visionary so that they can truly be in the visionary seat and keeping them in their lane. To pull the phrase from you, which I think is really helpful, keeping them in their lane.

Fractional is being able to do that for clients that don’t necessarily have the need or the capacity for somebody to do that full-time. That’s why I’ve been able to split my time. I’ve got four clients. I split it equally about 25% each of them throughout the week. That’s what they need because they don’t necessarily have the team or the size of business that requires somebody to be there full-time.

What’s interesting though, one of the clients I have here in France, they’ve just hired a full-time COO because of what we’ve done with his business in the last two years. He now needs somebody to be that full-time, 40 hours a week person that could be there. For the first two years, I was ten hours a week. That’s what they needed. It’s a matter of just doing it in that part-time arrangement.

I was just speaking with one of our COO Alliance members, and they were looking for a Fractional Chief People Officer, like a Head of HR who could actually coach their HR person. I reached out to our former Head of HR that I helped recruit at 1-800-GOT-JUNK, our Head of People. She’s actually going to talk to our member, which is great.

There’s going to be more and more of that where we have companies that are in the 10 to 50 employee zone that would love to have a CFO. They’d love to have a CMO, a real one, but they don’t need that $250,000-$500,000 person, nor can they afford it. They’ve got a person with a big title, but they’re really more a director level. They need some of that strategic guidance. They need some of that mentoring but not full-time either. Is that part of what you play is the mentoring role?

Yes, it is. It’s what I was about to say is part of it is being able to bring that experience of what I’ve done with Boldheart, which is now a multi-seven figure company. It’s been like that for ten years. It’s a leveraged business. It’s a self-managing business. Of course, we’re still involved with it, but we’re not involved with it pushing the boulder up the hill 50, 60, 70 hours a week doing everything. We’ve got 25, 30 people now. We’ve got people that own marketing, people that own sales, operations, finance. I’m in my integrator seat and I love what I do. Fabienne’s in her visionary seat and she loves what she does.

Being able to take that experience and that expertise and that playbook, if you will, and bring that to these other clients that don’t have the mindset or don’t have the understanding or even the structure. When I went into a client and we created for the first time, they were doing daily huddles with their team and doing meetings all of the time. Everything was in Slack and email. I’m thinking, my head’s spinning, “I can’t keep track of what anything gets done here.” We implemented a whole structure of how we use Asana.

Now, everything’s cadenced out in Asana, our annual, our quarterly, our semi-annual, all of the projects, all of the team members know what to do, when to do it by, who needs to sign off on, etc. We’ve built this process, this structure in place that’s been really beneficial, and it’s leveraging what we’ve been able to do or what I’ve been able to do with Boldheart, and then coaching those clients and those companies and the visionary to use that model, that framework that allows them to do much more than they would have done on their own or without having that knowledge.

It’s interesting you talked about pushing a boulder up the hill. I’ve always talked about pushing a snowball up a hill because as you keep pushing, it keeps getting bigger as you get it up that hill.

Exactly, it takes a different shape.

You said you were in investment banking prior to joining Boldheart.

I worked on Wall Street, but it was more in project management. I was the liaison between a lot of the investment banking, trading, salespeople, and then building technology platforms. I was that person in the middle that can bridge the gap between the two.

What firm were you with?

I was with UBS. Before that, I was with Lehman Brothers before they went by the wayside. I started off with Deutsche Bank back in the late ‘90s.

My old roommate wrote the book called Bear Trap about Bear Stearns. It came out right at the start of the collapse. I’m like, “How did you know about Lehman?” He goes, “We all knew about Lehman.” I’m like, “The book came out the week that it was happening. How did you know?” “We all knew.” What was it like leaving the investment banking world and joining a small entrepreneurial organization? If we’re hiring somebody from similar industries, what do we look for? What’s the DNA to say it will work versus it will be a disaster?

That’s a great question. At the time, it was a huge leap of faith. Again, you have to remember, I was then working with my wife. We were making a decision to work together in her business, which I knew nothing about. I knew nothing about business coaching. I knew what she did from afar and the clients that she had and what she was doing, but I wasn’t involved in the business at all.

I really came in without any knowledge. I made the comment once, “I had to start in the mailroom and work my way up.” What I mean by that is I had to get into the weeds of the business to really understand, “What is it that we do here? How do we make money? How do we get clients? What’s an email list? What’s a product launch? Why do we do these masterminds?” All of those things that were happening that I knew nothing about.

It gave me that perspective so that when I went to go and find the team and look at the right people for the right seats, I needed to have that perspective of not necessarily having done all of the work. I didn’t build the website, but I knew the importance of what the website was for. It was to generate leads. It wasn’t necessarily to be a glorified business card, or all of these things that we needed to do.

That was part of the mindset of trial and error, throwing myself into the deep end and figuring it out, but also leveraging what I was able to do for my days in corporate. In my sense, being able to, like I’d described, bridge the gap between developers and technologists and computer engineers and traders and salespeople, and making sure that the two of them are talking together, so when I came in, I could understand.

I won’t say translate it, but understand, “What’s the vision? What do you want to see this year? What’s going to happen?” Then be like, “I need to hire social media people. I need two more VAs. I need to hire a salesperson. I need to hire somebody that can do the website. I need somebody to do bookkeeping, customer service, coaches,” and being able to cultivate that, fulfill on the vision of what was coming from the visionary. It was an evolution of understanding more and more of what the team looked like that we needed to hire, and then making sure we had the right people in those seats. It’s been a process.

Do it with a smaller budget than you have in the corporate world, right?

Yes.

Hiring a person in the corporate world is like, “Sure, go for it.” In the entrepreneurial world, it’s like, “Wait, that’s a major hit on the P&L.”

Fractional Integrator: Hiring a person in the corporate world is like, “Sure, go for it.” But in the entrepreneurial world, it’s like, “Wait, that’s a major hit on the P&L.”

The French client that I have, we’re grooming his full-time CEO. He comes from corporate. He comes from healthcare. Anything entrepreneurial is a completely different mindset. Sometimes what I’ve also learned, especially because of the way that I’m wired, it made me realize that sometimes the plan is not the plan. Sometimes the plan is what we’re doing. We have this expression which is, “Sometimes we have to build the plane as we fly it.” That’s the nature of the beast in building and bootstrapping an entrepreneurial company. You don’t have the coffer of the cash and an HR department to go and hire all these people. We’re all wearing multiple hats. We’re all juggling lots of balls in the air.

When you can have the structure and this process to have some normalcy around it, and it feels like every day is whack-a-mole or flying by the seat of our pants, it allows us to scale and leverage. That’s part of what we’ve been able to do more and more. It’s a mindset. You need to be able to have some tough skin to know that not everything is going to work out to plan. Things change, things pivot. Just look at the last two years by itself, everything was pivoting. Everything was used to be in the events business. Now, we’re in the enrollment business. You have to be able to adjust and adapt like that.

That’s where the entrepreneurial builds or scales is when the momentum that creates momentum and then you scale the plans along the way, and then all of a sudden that plan becomes the infrastructure for the next stage of momentum. You’re working along that. Let’s go back to the 22-year-old Derek. I want you to give yourself some advice when you were 22. What do you wish you had known back then that you know for sure to be true today?

On 22, I had just started working at Deutsche Bank on Wall Street in New York City. I would say trust yourself that you don’t always have to have the entire plan fully laid out. I had this expectation in my mind, perhaps it was from my parents or society, that I needed to be in investment banking. I needed to be on Wall Street. I needed to have that trajectory of my career to the nth degree.

I shared this when I started working with Fabienne. I lived in Stanford, Connecticut, right outside of New York City. I used to take the Metro line from Stanford into Grand Central. I’d take a 6:00 AM train, and I would come home at 8:00 or 9:00 at night. I was working hellish hours. I didn’t see my daughter at the time who was just born. I was exhausted and cranky on the weekends. I remember sitting on the train, and if you ever take a commuter line, often enough, there’s an unspoken code of conduct, which is one, you usually have your own seat. Especially on this line, everybody is reading the New York Times, the Wall Street Journal.

I sat across from this guy for a few weeks where he was in the same seat, and he was older than I am, and looked very seasoned and professional, but it looks like he’d been doing that for 30, 40, 50 years. I had this epiphany being like, “I’m in my young twenties. Am I going to want to be doing that in 40 or 50 years? Is that who I want to become?”

Nothing against him. He probably had a great life and everything else, but that’s a long trajectory of what I’m going to be doing now, which yes, I might evolve and go to different companies and then slightly different role. I went from one industry to a completely different industry being an entrepreneur overnight. I could never be more grateful for having that experience because I am more of who I am today and could trust more of what I’m capable of doing today than I ever would have been able to if I’d stayed in that career path. That’s what I would share.

I’m guessing this is your last business call of the day. Your commute for now at the end of the day is about a one-minute commute to the kitchen and a kiss to your wife and a grab a glass of wine, right?

That’s exactly it. It’s a big change from that moment. I don’t know what it was, and maybe part of it was the inspiration from my wife of having done that. She left corporate and created her own business and then seeing that that’s something that I can do. That’s something that I could be a part of. I think also knowing that if we were going to do that together and have that foundation of our partnership be the backbone of everything that we could one plus one equals three, in terms of what we would be able to accomplish together.

It was very exciting, but it was a leap. It was like, “I’m leaving the cushy job. I’m leaving the salary, the insurance, everything else.” Honestly, Cameron, within three months, I remember, “I should have done this years ago. Look at the impact that we’re having.” Not just financially, but meaning and fulfillment, which I don’t think I would have got if I stayed in that career.

Derek Fredrickson, the COO of Boldheart, Fractional Integrator and COO Alliance member, thanks very much for sharing with us on the show. I really appreciate your time.

You’re welcome, Cameron. Thank you so much. It’s great to be here.

I appreciate it. 

Important Links

• Boldheart
• The Strategic Coach Program
• Canadian Association of Family Enterprise
• Bear Trap