The Entrepreneur’s Playbook: Scaling and Avoiding Costly Mistakes With Eric Crews

Eric Crews is the Founder and CEO of Crews & co., a management consulting firm dedicated to helping businesses increase revenue, profitability, and salable value. With decades of entrepreneurial experience, he is an EOS Implementer®, helping companies implement a business operating system into their organizations. In 2021, Eric launched the Growth Method℠, a proprietary business operating system designed to propel companies to new heights. He is also the CEO and Co-founder of CE Painting, one of New England’s largest commercial painting businesses.

Here’s a glimpse of what you’ll learn:

• [03:27] Eric Crews explains Crews & co.’s mission and consulting approach
• [04:57] Why Crews & co. provides finance, marketing, and operations support for SMBs
• [07:32] The importance of a three-year financial vision for business growth
• [10:10] Common financial mistakes businesses make and how to avoid them
• [12:26] What to look for when hiring a CFO
• [16:39] Eric talks about the Growth Method, a proprietary system for scaling businesses
• [21:09] How OKRs create company-wide alignment and drive growth
• [34:00] How Eric helped Mission Cloud grow from $500K to over $80M and get acquired
• [39:56] Why tough conversations and team trust exercises are crucial for scaling businesses

In this episode…

Scaling a business is no easy feat — many entrepreneurs hit roadblocks that stall growth, drain resources, or create inefficiencies. Whether it’s financial missteps, leadership blind spots, or an unclear strategy, these challenges can quickly derail even the most promising ventures. So what separates companies that scale successfully from those that struggle to grow?

According to Eric Crews, a seasoned entrepreneur and business strategist, sustainable scaling starts with financial clarity and strategic alignment. He highlights the importance of setting a three-year vision tied directly to financial planning, ensuring that every decision contributes to long-term growth. By leveraging OKRs — “Objectives and Key Results” — companies can align priorities from leadership to frontline employees, creating accountability and momentum. Without these foundational elements, Eric warns, businesses risk wasting resources on ineffective initiatives or hiring the wrong talent, both costly mistakes that can stunt growth.

In this episode of the Inspired Insider Podcast, host Dr. Jeremy Weisz sits down with Eric Crews, Founder and CEO of Crews & co., to discuss the key principles of scaling a company while avoiding common pitfalls. Eric explains how to build a financial framework that supports expansion, the role of OKRs in driving alignment, and the biggest hiring mistakes that hinder growth. He also shares insights on structuring businesses for long-term profitability and exit potential.

Resources mentioned in this episode:

• Eric Crews on LinkedIn
• Crews & co.

Special Mention(s):

• CE Painting
• Entrepreneurial Operating System (EOS)
• Measure What Matters: The Simple Idea that Drives 10x Growth by John Doerr
• Brendan Leonard on LinkedIn
• Glenn Grant on LinkedIn
• Great Hill Partners
• Mission Cloud
• CDW
• Mark Moses on LinkedIn
• Jeff Hoffman on LinkedIn
• John Corcoran on LinkedIn
• Gino Wickman on LinkedIn
• Traction: Get a Grip on Your Business by Gino Wickman
• Scaling Up: How a Few Companies Make It…and Why the Rest Don’t by Verne Harnish

Related episode(s):

• “[Top Agency Series & EO Chicago] Driving Digital Dominance With Mark Bealin of SearchLab Digital” on the Inspired Insider Podcast
• “Building Businesses and Meaningful Partnerships With Craig Swanson” on the Inspired Insider Podcast
• “How to Sell More And Save Time with Robert Hartline of Absolute Wireless” on the Inspired Insider Podcast

Quotable Moments:

• “Scaling a business isn’t just about growth; it’s about aligning strategy, finances, and execution at every level.”
• “Most companies don’t fail because of bad ideas; they fail because of poor financial planning and execution.”
• “OKRs help businesses focus on what truly matters, ensuring every team is aligned with key objectives.”
• “Hiring the wrong financial leadership can silently kill a business before you even realize what’s happening.”
• “The biggest difference between companies that scale and those that don’t? Clear priorities and relentless execution.”

Action Steps:

1. Align your company with a three-year financial vision: Mapping out revenue, profit, and valuation goals ensures long-term strategic growth and sustainability.
2. Use OKRs to drive company-wide alignment: Setting clear objectives and measurable key results keeps teams focused on the priorities that matter most.
3. Ensure financial leadership is the right fit: Hiring skilled CFOs, controllers, and bookkeepers prevents costly mistakes and strengthens financial decision-making.
4. Communicate priorities transparently in team meetings: Regularly reinforcing goals and expectations fosters accountability and prevents misalignment within the organization.
5. Assess and refine your business model regularly: Evaluating customer retention, acquisition costs, and revenue streams helps maintain profitability and long-term scalability.

Episode Transcript

Intro  00:00

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz  00:22

Dr. Jeremy Weisz here founder of inspiredinsider.com, where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Eric Crews. You can check him out at crewsandco.com. Eric, before I formally introduce you, I always like to point out other episodes of the podcast people should check out.

This is as part of the top EO member series. I’ve had quite a bit of EO companies on actually. Eric and his company work with a lot of EO companies as well. Mark Belen talked about driving digital dominance, and he runs — he’s in Chicago, runs Search Lab Digital. I had Craig Swanson of Seattle.

He talked about building businesses in meaningful partnerships. He was the co-founder of Creativelive. And Robert Hartline of EO Nashville was another one he built up absolute Wireless to. He started from scratch and built it to over $100 million. And it was a pretty incredible journey that he shared.

That and many more and inspiredinsider.com. This episode is brought to you by Rise25. At Rise25, we help businesses give to and connect to their dream relationships and partnerships. How do we do that? We do that by helping you run your podcast.

We’re an easy button for a company to launch and run a podcast. And we do the accountability, the strategy and the full execution. So, Eric, we call ourselves the magic elves that run in the background and make it look easy for the company so they can create amazing content, create amazing relationships, most importantly, run their business. You know, for me, the number one thing in my life is relationships, and I’m always looking at ways to give to my best relationships, and I have found no better way over the past decade to profile the people and the companies I most admire and share with the planet what they’re working on. So if you’ve thought about podcasting, you should.

If you have questions, go to rise25.com or email us at [email protected]. Eric also has some amazing content on his website, which we’ll check out. I’m excited to introduce introduce. Eric Crews is founder and CEO of Crews & co. Eric has guided over 100 organizations to increased and sustainable profitability while optimizing their operations and also instituting an elevated quality of life for their leadership teams, which is super important.

He’s been building on decades of successful entrepreneurship, eight years as a certified EOS implementer with over 1,000 sessions. And Eric led Crews & co.’s 2021 launch of the Growth Method, which we’ll talk about. It’s a proprietary business operating system designed to propel companies to increase revenue, profit and saleable value. And Eric is also the co-founder and CEO of Sea Painting, one of the largest commercial painting businesses in New England. Eric, thanks for joining me.

Eric Crews  03:13

Thank you, Jeremy. I appreciate you having me. Appreciate it. I’m excited to dig in.

Dr. Jeremy Weisz  03:17

Because I’ve been consuming your content online. I figured just start us off and talk about Crews & co. and what you do. I’m going to pull up your site as you do it.

Eric Crews  03:27

Awesome. So Crews & co. is a management consulting company that focuses specifically on small and medium sized businesses where like consulting for the rest of us, we’re the Deloitte for small and medium sized companies. Ultimately, when a company brings us in, they’re trying to align the company from top to bottom on the right priorities. They’re going to drive what we call RPV, which is revenue, profit and valuation. So we get hired by a small and medium sized company.

They’re trying to take this vision where they’re trying to go, and they’re trying to figure out what do I need to be doing to achieve that vision. And then how do I align my company from the senior team throughout the entire company on what those priorities are and how to get them to do it? And then we also have all the resources they need. We have a finance company, we have a marketing company, we have an operations component of our business as well. So we have all the resources they need along the journey. But ultimately we’re trying to drive RPV in every company we work with.

Dr. Jeremy Weisz  04:33

Eric I find that to be unique. When I hear a company that you actually have pieces that the companies you help, like with the finance and other things. Talk about that decision. Because that’s also a lot of work, right. Like you can help them with, you know, the strategy and everything they need to do, to do, but you’re also behind the scenes doing some of the stuff too.

Eric Crews  04:57

Yeah. So you’re asking. It’s a really insightful question. I don’t get very often actually. So I we’re kind of like the anti-consultant company.

Honestly I, we’re a consulting company. It’s what we do. We’re going to help you grow. We’re help you figure out the priorities. But we really are designed for small and medium sized companies.

Companies under 1,000 employees. That’s I mean some our companies are quite large. We work with. But what I found after being an entrepreneur for so many years is you can set these priorities as a company. You can align to the priorities you have as a company, but then you can go out and hire resources to help you achieve some of these things that you need to get done.

And you just get bamboozled. For lack of a better word, you get vendors who sell you a bill of goods, they charge you a fortune, marketing companies that will charge you X amount of dollars per month, and then you won’t get any ROI. Finance companies that don’t know how to speak the language of a CEO or a small CEO, or recruiting resources that aren’t set up properly for you or, you know, whatever the case might be. So ultimately, we built all these different parts of our company, specifically with the small business person in mind, because when we were working with these teams to figure out what they needed to do, we’d find they’d go out and try to get things done, and they’d hire these resources, which would set them back six months. So we created boutique resources that we think are designed that we know have been proven to help our companies in these specific areas.

So we have M&A and M&A function that’s set up just for small and medium sized companies. We have search functions that are the same. And the finance company that’s designed to speak to CEOs and leadership teams using words. They can get it. They can understand.

But we’re also giving them the top cream of the crop resources. We’re just putting them together in a way that they can afford and process. So that’s our goal. And it’s not easy. It has not been easy to do.

But after being an entrepreneur for 20 years, I just got sick of hearing so many people say they’re going to help me and then spending a fortune and then not being able to get results from what I was being sold.

Dr. Jeremy Weisz  07:05

Yeah. Do you remember that time? Because like obviously you have the growth method, which you’ve developed over decades, right? But then do you remember that moment where someone’s like, hey, we’re struggling finding, I don’t know what the finance or the operations and you’re like, okay, we’ll just do it for you because, you know, that’s a big decision, right? I mean, because you have a certain focus.

What was one of those times when you’re like, let’s just do it for you and make it easy.

Eric Crews  07:32

So here’s what happens a lot to us. So for us, one of our most important things we’re focusing on, we’re helping a company scale is not just a one year plan or quarterly priorities or OKRs. We use OKRs objectives and key results to set priorities with the small business. In Business in particular, we find that they don’t focus enough on dialing in the three year vision of the company and even converting it into like a mini business plan. Now, not going crazy.

You don’t need to hire Deloitte to do this stuff, but to the degree that you’re going to scale your company is way beyond one year. It’s usually needing a vision. That’s pretty clear in terms of how you’re going to get to where you’re going in three years. To that end, I like our companies to link that to their finances. So if they say they’re right now there are $7 million company and they’re going to grow to $14 million, I want to have them map that out.

What does that look like for this year financially? What does that look like for the next two years? Beyond that, what do I need to have for cash flow, for investment? What exactly am I investing in specifically, and what’s the ROI need to be? And is my plan just crap?

Honestly, I’ve spent so much time creating my own plans that were junk, honestly, that I finally just said not. I’m not going to work with a company anymore where they say they’re going to double the company without having the financial plan. And the backdrop to say it’s actually going to be actually going to work. And what we found is that that financial planning, three year and one year and quarter actually then drives all the decision making in the company. And without that, you end up just setting a bunch of priorities that you really can’t figure out if you’re getting ROI on those things or not.

So we think it all links up and we had to build. I had to build a finance function because I would send people to other firms, and I wouldn’t be able to get the results I needed for them to get to help them as a company. So we just built it ourselves. It took us years to build this engine, honestly, but now we have a team of, I think 16 or 18 people inside the finance company, 4 or 5 CFOs, bookkeepers, controllers. And if we have an issue we have with the client or client wants to really translate that vision into a financial reality. We can get that done pretty quickly.

Dr. Jeremy Weisz  09:50

I’m looking here at the page here. Right. We’re in the Crews & co. We’re on the finance page here. And you can see kind of the executive coaching operations human resources contingency and everything else.

What are some of the biggest mistakes people make with this. When they’re thinking of their financial engine.

Eric Crews  10:10

So. So it’s interesting you’re keying on finance. Finance is a fractional finance is one of the fastest growing spaces that exist in the business world, which is kind of funny. We kind of stumbled into it. We weren’t trying to grow a big finance company.

We were trying to help our clients. But we have plenty of companies that we work with that are just finance clients. Also, they’re not clients of our growth method or of our consulting team. So what issues do I see that people making? One, because unless a CEO or a senior leadership team has strong financial background of some kind, They will put people in roles that have titles and think that they’re going to deliver because they have a certain title, so they’ll put somebody in a controller role who really is more of a bookkeeper.

They’ll put people in a CFO role who really is more of a controller. And ultimately, you have overreliance on people and numbers and delegating to people that really can’t drive the business financially. So sometimes a CFO will be there, and a CFO whose job is to tell you where to take the business financially. And they will not actually have the basics covered. Sometimes I’ll see a controller who people love.

I have a phenomenal controller. I absolutely love my controller, but he’s not a CFO. He won’t tell me where to go. He will tell me how things look and he’s very good at that. And people don’t understand the differences between bookkeepers, controllers, CFOs.

And without knowing that information, you think you have a resource that’s guiding you. And then we go in there and I say you’re this is not it’s not, you’re not where you think you are. And you don’t have a plan to get to where you want to go. And then we have to figure out what that combination you need is. And usually it’s a combination.

It’s usually a combination of controller and CFO and bookkeeping. Honestly. And knowing the mix that’s required based on where you are is crucial.

Dr. Jeremy Weisz  12:11

Yeah. As you were saying, controller is like how things look.

Eric Crews  12:15

CFO is where do I need to go?

Dr. Jeremy Weisz  12:19

Where do we — where do I need to go? What do you look for in a good CFO?

Eric Crews  12:26

So first of all, hiring is difficult as a whole. So we built a hiring engine. We also have hiring partners we work with for C-suite positions. But we hire a lot of people ourselves. Also, we have an internal recruiting engine.

Hiring is an art. So. If us or one of our partners is hiring for a CFO in particular. First, we’re trying to look at the story. I recommend this for anybody.

Does the story of them being a CFO actually makes sense? Are they actually even a CFO? That’s one thing we get. Some people bill themselves as CFOs when they’re really not. So we look at what did they achieve in their previous background.

What companies have they driven to success? Who was around them on the leadership team and the companies they were had they were previously? Were they a financial reporting element of that team or were they a financial driving element of that team? So for a CFO, we really want more of a person that can kind of tell us how to build the clock, to use a Jim Collins analogy, rather than tell us what time it is. And we’re going to be looking to see how much of that they’ve done in the past.

For comptroller, we’re going to index more on accuracy of the books. Are the books accurate? Are they telling us what we need to know, at least accurately, from a numbers standpoint and from a bookkeeper. It’s just the magic elves, as you would say. Are they actually working in the background to get the numbers in the right spot?

Dr. Jeremy Weisz  13:56

At what level have you found? Obviously there’s a lot of different services here. I’m just speaking the finance piece. Does the company have to be at to make sense? Right.

I don’t know if it’s a staff level or revenue level to be like, listen, we need, you know, because we’re looking at this bookkeeping comptroller and CFO services. What is where should they be at? To make sense to work with you.

Eric Crews  14:21

It’s a great question. So everybody needs a finance function. So for us it’s less about whether or not. So if you can have one full time person you don’t need to go. Fractional.

You can you can hire somebody yourself. We only provide resources because our clients happen to need a lot of these things. But you can hire somebody yourself if you need a need a full time person for. Usually a controller will show up when a company is $5-6 million and they can usually get away with it up to $8-10 million, sometimes $12 million. You start seeing the CFOs appear $12 to $15 million, but there’s a different reality behind that.

So for us, we’re a consulting company. So when we go in and help a company, our consulting team comes in, helps them set priorities and figure out what actually needs to be done to grow. The different component is we may not need a CFO until we’re ten, $12, $15 million, but we need sprinklings of a CFO potentially now even at $6, $7, $8 million. So when we build a scope of work for a company, we’re asking ourselves, what does this company need for sprinklings of these resources? And our goal is we’re pretty boutique, and it’s not the only reason we can get away with it, honestly, is Because the marketing, we don’t need a marketing engine of our company.

We already have a consulting firm, so we have our costs pretty low. So we’re a little more boutique than a lot of finance companies. We can do custom engagements short term, longer term and still do well financially as a company. So we’ll come in and say you only need a couple of hours a month of a CFO. You need ten 20 hours of a controller, and you’re going to get a higher horsepower engine.

Sometimes even for less than you’d pay for one employee. So we’re just about figuring out what is the sprinkling of the combination of these that you actually need.

Dr. Jeremy Weisz  16:14

That makes sense because in order to grow, it’s like, well, you need to like you said, someone saying, where do we need to go? But, you know, you’re maybe not someone’s not at the point where they need a full time CFO at that point. I’d love to talk about the growth method. Because this is kind of what you’ve created over decades as an entrepreneur. So can you talk about that?

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