1757- How Outsourced Leadership Can Help Businesses with Bill Simmons

In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Founder & CEO of Thrive Business Operations, Bill Simmons.

Simmons wide

Bill Simmons founded Thrive Business Operations with a clear vision in mind. He saw a gap in the market for outsourced executive leadership, specifically on the operations side of businesses. For over a decade, Thrive Business Operations has been offering fractional SEO services and serving as a chief operations officer for various businesses.

Bill's role is to assist business owners whose vision is outpacing their operations. While he acknowledges that he can't eliminate the gap entirely, his goal is to shrink it and help operations meet the demands of the company's vision.

Bill emphasized the importance of a clear vision for founders. He believes that founders are visionaries and creators who aspire to be part of something bigger than themselves.

However, he also warned against the trap of thinking that nobody can manage or love the business like the founder. This mindset, he cautioned, can limit growth and prevent the founder from scaling their business.

Key Points from the Episode:

  • Bill Simmons' role at Thrive Business Operations
  • The need for outsourced executive leadership in operations
  • Shrinking the gap between vision and operations
  • The role of a founder and the importance of a clear vision
  • The five-step process called the Thrive Ops Cycle
  • Connecting and aligning with client values and vision
  • Identifying impactful goals and initiatives using the OKR framework
  • The involvement of the Thrive team in client's operations

About Bill Simmons:

Bill Simmons is a seasoned entrepreneur with over 30 years of experience dedicated to aiding business owners in enhancing profits and reducing frustrations through strategic execution and organizational advancement.

As the founder of Thrive Business Operations, he specializes in Fractional COO Services, addressing operational challenges for growing businesses.

Bill's expertise extends to leadership and success, and he has captivated audiences worldwide, delivering impactful speeches to over 250,000 individuals.

His gift as a storyteller inspires and imparts valuable insights from his wealth of experience. Thrive Business Operations focuses on unlocking business growth by integrating a Fractional Team and optimizing operations through The Thrive OpsCycle, emphasizing smooth operations, improved communication, and heightened accountability.

About Thrive Business Operations:

Thrive Business Operations specializes in Fractional COO Services, offering expertise in team building to bring entrepreneurial visions to fruition.

Targeting entrepreneurs and small business leaders seeking relief from the challenges of having their business run them, Thrive excels in minimizing operational frustrations, even for those opposed to systems and processes.

The company's strategies are designed to optimize time management, enhance team efficiency, and yield cost savings.

Thrive Business Operations stands out for its commitment to streamlining operations by addressing the common struggle of businesses running individuals.

Whether you dislike systems and processes or seek improved effectiveness, Thrive's approach is tailored to reduce frustrations and empower business leaders to regain control.

Tweetable Moments:

03:25 – “Don't be a founder or business owner that we've all fallen into that trap where we may be tempted to say nobody does it like me, nobody will manage this or love this like me.”

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Links Mentioned in this Episode:

Want to learn more? Check out Thrive Business Operations  website at

Check out Thrive Business Operations on LinkedIn at

Check out Thrive Business Operations on Facebook at

Check out Thrive Business Operations on Instagram at

Check out Bill Simmons on LinkedIn at

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Check out Bill Simmons on Instagram at

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Josh (00:00:05) - Hey there, thoughtful listener. Would you like consistent and predictable sales activity with no spam and no ads? I'll teach you step by step how to do this, particularly if you're an agency owner, consultant, coach, or B2B service provider. What I teach has worked for me for more than 15 years and has helped me create more than $10 million in revenue. Just head to up my influence and watch my free class on how to create endless high ticket sales appointments. You can even chat with me live and I'll see and reply to your messages. Also, don't forget the thoughtful entrepreneur is always looking for guests. Go to up my influence and click on podcast. We'd love to have you. With us right now, it's Bill Simmons. Bill, you are the owner and CEO of Thrive Business Operations. You're found on the web at Thrive Business Operations. I love this subject. Bill, it's great to have you.

Bill (00:01:12) - Gosh, thank you for letting us be a part of this. I've been excited about this.

Bill (00:01:16) - I've actually listened to a couple of podcasts where you were the guest, and I just couldn't wait till we were going to get together.

Josh (00:01:22) - Oh, fantastic. Well, I appreciate that. Well, Bill, give us an overview of the work that you do at Thrive Business Operations and Founders. Listen up. Bill's about to become your best friend.

Bill (00:01:31) - Yeah. So very simply fractional SEO services chief operations officers. You know, the marketplace has been using fractional CFOs on the financial leadership side for decades. And I saw a need in 2006 of outsourced executive leadership on the operations side, and about ten years of that, doing it solo now, doing it on my own. The way I describe it is if you have a vision as a business owner that operations can't keep up with, we should have a conversation, right? And I can't promise you that we're going to eliminate that gap, because if you're a good visionary, there's always a gap. But we want to shrink that gap, right. Let's try to get operations to be able to meet the demand of where your vision and where you want to go as a company.

Josh (00:02:18) - Yeah. Would you mind talking just a little bit about the role of a founder? And also you had mentioned kind of that personality type of visionary. And I think my suspicion is that a lot of founders are visionaries. But I'd love your take on this.

Bill (00:02:36) - Yeah. Visionary. I love the word creator too. Right? I don't think creativity is limited to artistry. I think business and entrepreneurship is an act of creation. And we get to create, we get to have ideations and get those ideas executed. And in the life of a lot of founders and business owners, when they have that clear vision and and they are successful and what that baby they've created, there comes a point where scaling it needs partnership, right? And you're not on your own. And being able to bring somebody else where you are, it's not, you know, the book is right, not how, but who. Right. We and we're big on being the who to come alongside that creator, that visionary to take their business to beyond where they can on their own.

Bill (00:03:25) - I think the other thing is, most founders and business owners feel compelled that they want to be part of something bigger than themselves. And if that's the case, you need more than yourself to be a part of it. So don't be a founder or business owner that we've all fallen into that trap where we may be tempted to say, nobody does it like me, nobody will manage this or love this like me. That is a trap to contain you right where you are as a yes. And so get out of that trap. Find real, legitimate partners that believe in what you're doing, and take this beyond your wildest imagination.

Josh (00:04:03) - What are the consequences of saying stuck in that trap?

Bill (00:04:07) - Well, certainly frustration. I call it the frustration quadrant. There's that's a whole other thing. Give me a whiteboard or a yellow pad and love to draw things out. But in the context of this, I think it's really about understanding that when you get trapped being the person and the process and developing the processes to execute the majority of your business, frustration is the result.

Bill (00:04:31) - And then what happens is you start turning on the thing that you love, right? Because it's working you instead of you working it. And you need to be a leader, not just a business owner. I know that can be semantics, but leadership requires people and processes to lead, and that's what we're looking for. We're looking to work alongside leaders.

Josh (00:04:53) - Yeah. What do you think keeps most founders and or CEOs from bringing in the operational leadership that they need?

Bill (00:05:04) - Well, I think there's a couple of things. One, the first and foremost, not really knowing what they want them to do, they just know there's a gap and there's a hole to be filled or there's just stuff I don't want to do anymore, and I need somebody else to do it. Not being clear on what a CEO should be doing, I think that's the first thing. The other thing is they've had some type of operational support and it went bad. And dare I say, because of unclear expectations, I'm using that word frustration a lot.

Bill (00:05:35) - That's when, you know, unspoken unmet expectations equals frustration. Right. And so you have either a bad experience with somebody operationally. And now you're like, hey, I might as well just do it myself, which is again, a lie. You tell yourself, or you just really don't know how to use them. And I think that's part of what we do. We want to say, here's how you should use us. And a good fractional COO. Now listen, there's a lot of competence. Out there and we're getting into a crowded market. I've been doing this a while when I can say, hey, I think we were on the early stages of fractional Clos. And the reality is, Josh, most people don't care, but I want to at least carry that card as long as I can. Right. But the market's getting crowded. Don't settle just for somebody who has competency and experience because they've been with a company in the past. Yes that with a fractional Co that has a process and how they're going to deliver this operational service to your company.

Bill (00:06:28) - That's a whole other conversation. We talk about how we do that. But I think that sets us apart to be able we can tell you as the business owner, here's how you should be using us. Here's how we implement that so that you are on the right track. We're big on what we call quarterly sprints. We believe our number one job is to help you run your business 90 days at a time, and being clear on those expectations on how we work together. So if you can overcome those two things, you know, having that bad experience, let's work with somebody that has experience doing this in multiple industries over multiple years, and at the same time, that really knows how to help you utilize the service.

Josh (00:07:07) - Yeah, Bill. And I think that that kind of moves nicely into my next question. And that is, you know, in terms of options that are available to us. So three, I think that immediately come to mind is to say, well, look, I'm still going to stay on pretty hands on.

Josh (00:07:21) - I'm just going to bring in this project manager or something like that. Not necessarily. They're not C-suite, they're not executive level, but at least they're going to start managing some things. So I don't, you know, hopefully I can kind of tell them what my vision is and they can kind of manage the troops a little bit, you know, a small team or something like that. That's one option. The other option could be, again, you know, fractional C-level executive leadership, but on a fractional basis. And then finally, you could also say, well, no, I'm just going to bite the bullet and I'm going to get a full time coach in here. Maybe you could talk about the pros and cons of each of those and those are just three off the top of my heads of ways to kind of solve this. Oh, guess option number zero would be do nothing, which we already talked about. Yeah.

Bill (00:08:06) - Do nothing as a guaranteed way to stay right where you are right.

Bill (00:08:09) - Yes. So you are a business owner. You're the founder. You're the entrepreneur because you took a risk. Scaling is risk taking also. Right. And so, you know, dance with who brung you. You know, you want to make calculated risk. But if you are a risk taker when you began be a risk taker to nugget there. Let's talk about your three things. I believe that when it comes to fractional Co versus a full time Co, sometimes that depending on the company that a person coming in full time still gets lost in the day to day urgency of executing fire drills and maybe doesn't have a strategic approach that really is driving having somebody that is willing to partner with you but is also somewhat disconnected from you, gives you the ability to have a fraction of the time and a fraction of the cost actually get more accomplished because you want high level things to accomplish. I'll use numbers for exaggeration for a fact, but let's don't pay $500 an hour for somebody to do tasks that should be $5 an hour, right? Just, you know, exaggeration for a fact.

Bill (00:09:20) - And so we want to make sure that we can actually get more accomplished. And when we hire somebody full time, I say we end up asking them to deliver lower level tasks they shouldn't be doing. Now, talking about the director side of things, that's actually somebody Josh we'd love to work with in a company. If a company has maybe somebody that seems very competent, very organized, that office manager or director of operations, but they're not quite strategic in their direction. Well, that's where we can come in and be a partner on the strategy and execution and clarifying quarterly objectives along with that person, and elevate their efficiency and effectiveness as a director and saving you cost in dollars in revenue as well.

Josh (00:10:09) - Yeah. So, Bill, what does engagement look like? So someone says, look, I think we might be a good candidate. All I know is I'm overworked. And what does that those initial conversations, the kind of that initial discovery look like.

Bill (00:10:25) - Yeah. You know, certainly the discovery is everything's built on relationships.

Bill (00:10:29) - And, you know, first thing we want to do is connect and make sure that we're aligned and we want to work with people that we can share values and we want to share their vision. We can get behind that vision as well and support that. Ultimately, you know, our engagements, we have a five step process we call the thrive ops cycle. So I can say every engagement is going to work along this way. We start with our strategy advance. We want to be clear on the vision and culture you're trying to create. It is not our job to come in and disrupt your vision and disrupt your culture, but we can't replicate it if we don't take time to truly understand it. So we want to start the engagement there. Then recognizing as a part of that strategy. Advance. What are the most impactful goals and initiatives we can take on in the next year to bring growth and health to this company? And then once we've identified those, then it's off to the races, identifying quarterly objectives.

Bill (00:11:29) - We're an OKR firm we love. I know it stands for our objectives and key results. I like the term outcome and key results. What outcomes are we clearly going after on a quarterly basis. And that's where the rhythm just keeps working from there. So every engagement starts that way. And then from there it's rolling up your sleeves and getting involved. We often say don't call us coaches or consultants, but everybody on our team is capable of being a coach and consultant, and we do that stuff for free. And not to be cynical, okay, I'm being cynical. Everybody's a coach and everybody's a consultant these days, so let us just bring that as a value add. Let us roll up our sleeves and get involved in your team.

Josh (00:12:08) - Yeah. Bill, your website thrive business operations. You know, I know we've shared a lot of great value here, but I suspect that you've got some valuable resources here.

Bill (00:12:20) - You know, one of the things we're very proud of is our e-book, The Thrive OP Cycle, that shares our business operating system that we want to install in your business to keep us on track.

Bill (00:12:31) - You may have heard of other business operating systems like retraction and EOS and the 12 week year and scaling up. We're all saying similar things. This is our version of our business operating system, so we can have predictable executable results. And so I would highly encourage somebody to visit our site. That's our free gift to you. And it's a great way for us to start a conversation, to know how we can come in and help you install that now.

Josh (00:13:01) - And, you know, kind of finally, tell me a bit about thriving business operations as a business itself. Who are you? Like, where have you come from and where are you going?

Bill (00:13:10) - Yeah, so I started the company in 2006, and that's a story in and of itself. I had been an executive director of a nonprofit in Washington, DC. I had the privilege of being on the road quite a bit with a lot of speaking engagements. At 300 speaking engagements in six years. I did a lot of public school assemblies. I was young, skinny and had hair back in those days, and you got to be a little ballsy to stay in the middle of a high school gymnasium with 3000 high school students, right? But that led me to having a lot of conversations with leaders, community leaders, business owners that were funding our participation in those events.

Bill (00:13:48) - And I just saw a need of that's outsourced executive leadership and started a company, did a lot of it from all my own, but then had a vision for what a firm looks like and how we could productize delivering the service, bringing other highly capable, experienced CEOs to help serve our clients along the journey. We had different team members, but Kai Bailey is my partner now. I'm in the Greenville, South Carolina market. She's in Atlanta. We serve clients all across the country, but we're now business partners. We join forces, and I think we are the definition of synergy. We truly are better together than we are separated and are able to provide a much better service and product for our client.

Josh (00:14:32) - Excellent. All right. Again, Bill, your website thrive business operations. What does somebody click on. What do they do. Where do they go next.

Bill (00:14:40) - Yeah definitely go to the website. And right on the front page is going to be the thrive op cycle. You get an instant download of the e-book.

Bill (00:14:49) - Also, I love having conversations like this, but schedule a time with me. You're going to get me and sometimes Kai will join me, but we can just have a get to know each other's session. You can also just go to just about any social media platform LinkedIn, Instagram, all of them. Find Bill Simmons Live. Live. If you look for Bill Simmons Live on Facebook, Instagram, LinkedIn, you're going to find me. I like being friends, I like being connected, and I love sharing. Hopefully what we think is good, motivating and sometimes contrarian content when I'm just tired of hearing the same things over and over again. So I like to say things just a little bit different and hopefully we're providing that for you.

Josh (00:15:29) - Awesome. All right. Bill Simmons again, thank you so much. Founder and CEO of Thrive Business Operations. The website one last time is Thrive Business Bill thank you so much for joining us.

Bill (00:15:39) - Thanks, Josh. It's been great.

Josh (00:15:46) - Thanks for listening to the Thoughtful Entrepreneur show.

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