GROWTH PILLAR: Leadership & Ops
WHO THIS IS FOR: SMB owners / Solopreneurs / Corporate escapees / Leaders building systems
WHAT THEY'LL GAIN: Actionable insights, hard-won lessons, real growth strategies
Most business owners can't see cash flow trouble until it's already a crisis.
Diesha Cooper is the founder of Execuly, a fractional CFO/COO practice built around one job: walking into businesses in distress and getting them moving again. She bought her family's industrial company at 28, turned it around in four months, and grew it into a multi-million dollar operation before selling to her partners in 2021.
In this conversation, Diesha breaks down the warning signs owners miss — profit on paper that hides negative cash flow, owner wages that are too low to reflect real market value, and operating systems that were never built to scale. She also shares how she's applying agentic AI training from Harvard to turnaround work, and how launching her own product, Siplux, taught her e-commerce and marketing from the ground up.
Key topics covered: cash flow blind spots, paying yourself a reasonable wage, operational architecture, and what it actually takes to rebuild a business under pressure.
Connect with Diesha: LinkedIn | Execuly | Execuly blog | Siplux | Siplux Instagram
Co-hosted by Percy Barr and Wayne Pratt.
— PARTNERS ON THIS EPISODE —
Next Steps:
Diesha (00:05)
I'm from Lancaster, Pennsylvania, and ⁓ I my
Private practice is in turnaround consulting as a fractional CFO and administrative officer. I got into this work about four years ago after a 20-year run in family business. I co-founded an industrial company as a teenager with my dad and did 11 years with him, started out as the bookkeeper and the welder.
and ended up a general business administrator and ⁓ it was a pretty wild run with my family. my dad got involved in a cult. That's a whole other story and basically you know the pending Netflix series if it was up to my friends. they keep begging for that show. but my cash stripped his business and moved out of state.
down to Kentucky from Pennsylvania in 2014. And I went to his private lender, who was he was in default to and bailed my dad out of debt and bought his business on a very large private note to his private lender. And at 28 years old, I looked at my two younger brothers who are working in the business there, 20 and 22, and I said, we're gonna work harder and smarter.
And you're gonna listen to me and you're gonna work your butts off. Get busy. And that was my first turnaround. We started servicing our debts within four months of a negative cash situation. And I also took it from it was a couple hundred thousand of revenue at the time when I bought it and took it to a multi-million dollar company over the next seven years. When I sold to my partners, ⁓ 20 years in the industrial sector was long enough for me with family, as you can.
only imagine what it's like. And my welding skills, while it makes me sound like I'm pretty tough and badass, I I might be a little still thin skinned when it comes to relationships. so I exited end of 2021 and took a six month sabbatical, did a lot of kayaking.
To figure out what do I want to do next with my life, is kind of at that transition point. And I said, you know, I know a lot about business administration and finance. I'd been in the CFO role for a while. and I came back to work as a business consultant and got hired by a firm. It lasted six months there when I realized my entrepreneur streak is quite deeply embedded and working for
Someone as a W-2 and just being the billable hours on it in a big operating system was really not the vision that I had for myself. and in that six months that I worked for that firm, I met other people who were doing fractional work. And I was like, wait, what are you doing? You're not just telling people what to do, you're actually in there doing it. And I was like, yes, that's what I want to do. So I ⁓ exited again the consulting firm and hung up my own shingle as a fractional CFO.
and started prospecting. It was really the first time in my life I've had to do sales or marketing for myself. Having, you know, bought a business that was that had a full team, I was like, okay, now it's the the person of one doing everything, consulting my clients, getting out there, networking. And you know, in the last couple of years have built a fairly successful consulting practice as a fractional.
I think the thing that a lot of people want to hear from me, and I suppose probably this group too is like, how do we avoid as a as a turnaround consultant? I'm in, I go in when there's fires burning, the cash is run out. we're saying, is this a bank propsy situation, which sometimes it is, or is it something we can actually fix and turn around? which thankfully in my case, most of the times
we are able to do a turnaround on these businesses. And the question is like, how do you see the writing on the wall? How do you know what is, you know, what you need to be looking for so that you don't end up distressed, especially when you're a founder or a very technical business owner and you don't necessarily understand finance or debt servicing and some of these things and can really get stuck. And I think for me when
When I look at small businesses, one of the first things that we're looking at is what is their cash flow. you can look profitable on paper, but ⁓ one of the big things that happens is with especially single member LLCs or small LLCs where owners take distributions off the balance sheet, it can look like they're profitable, but maybe they're making 20,000 in net income and they're taking home 40,000 or 50,000.
off their balance sheet and they're actually ⁓ cash flow negative and they're struggling. And, in my mind, if you've ever heard me talk or follow me on LinkedIn, one of the things I'm I'm really keen on is that if you're gonna be a business owner, you should pay yourself a reasonable wage. And when I say reasonable wage, I'm not talking about the IRS standard. I'm talking about what's the wage you go out and get replaced with.
if you took this job elsewhere or if you hired someone to do this work in your company, whether that's you know, if that's $70,000 plus benefits and employer portion of health insurance or 401k matching it often comes out to about $100,000 for a basic $70,000 ⁓ wage, which in the US, I don't know about Canada, when we look across
the board as ⁓ operating managers, $70,000 to $80,000 is a pretty realistic small town ⁓ income. And so over 86% of our US small businesses are taking home much less than that. Their entire revenue is less than 100,000 and the business owner themselves are paying themselves $30,000, $40,000 in hopes that they're building an investment for later
Basically believe they're putting a sweat equity and they're all of their hopes and dreams are in the future than them right now. It's the struggle. and only 10% of the one that we put our businesses up for sale in the in the US even sell. So most of them aren't even building an asset. the space that I work in primarily with larger turnarounds is between one to 20 million, which is a big range.
And you know, I I usually have about 20 million total in operating revenue that I'm managing. and it's really interesting to see how similar a business at a million and a half revenue is to a build business in 10 million in revenue when they're distressed. The things that we usually see are operational chaos.
And this is the thing that I've gotten really fascinated with in the last year as I've begun to see patterns in the last few years as I've been working with small businesses where you have say a 20-year-old business where it's family or founder-led businesses, and they've kind of patched together their operating architecture as they grew. So that you know, they start out their hundred thousand, they're two hundred thousand, they're
using these tech tools, they have certain ways of doing things and then they they get successful and they start building, but the profit isn't coming along with and then they hit you know a real growth spurt and suddenly they're they're cash deprived and they're panicking. And that's when I get the call of like what's wrong? We need help come in. I think we're gonna have to file bankruptcy. and consistently what I see is they've
They've gotten very excited about growth and put a lot of eggs in one basket and just gone all in for growth and not done it right. They haven't built the architecture to scale to enjoy economies of scale. Instead, they're scaling up with increased labor costs, they're scaling up with increased technology costs, these things, instead of actually being able to ⁓ optimize what they have and get more.
production through they're simply scaling everything at size. And so this becomes a really fascinating and very individual process for each of these companies is walking in and saying, okay, what works, what doesn't work, what can be optimized. And I think in in my own evolution as the consultant slash executive leader, I am learning to step back and instead of fixing processes, I'm beginning to question
The entire operating architecture and say, if we were building this again today, would we build this system? I have a client right now that I've just been frustrated and frustrated with trying to get financial reports from the controller. and I've taken a step back and they've said, you know what? When I if I would walk in here tomorrow and buy this company, I would not take.
anything from their technology stack with me. I would say, I'll buy your product, but I won't buy your tech stack. I'll buy your customer list, but I won't take your CRM. I buy this, but I wouldn't take and I said, well then if I wouldn't buy this as an investor, why do we keep operating with it? What if we make my client's company 2.0 and we say on this date we move everything into a new operating structure just like if we had been acquired by someone
So that we can actually scale this thing because we can't go from 2 million to 10 million in the system that we have. And I think that the thing that just keeps standing out to me so much is this the need for me to stay curious, to stay educated. I just completed a course with Harvard on agentic AI and finance, which was incredibly eye-opening, understanding how to work alongside AI agents to
have more profitable companies and to ⁓ delegate mundane tasks to. And again, it comes back to operating architecture and what the future of architecture looks like for businesses as we commingle both AI workers and human workers with humans moving into more creative and intuitive roles that will increase profitability that will
increased work-life balance, productivity, all of these things. So I'm I think like for me I'm really leading with curiosity and ⁓ working to understand what is it that is going to move the needle for businesses as we see more and more distressed companies coming out as through this huge tech change that's happening.
⁓ across the world right now in the boom of technology and AI-led technology, and how do small businesses capture some of that profitability and revolutionize their businesses in a way that founders and small business owners will be able to enjoy work-life balance, enjoy profitability in those things. Anyway, that's that's a little in a nutshell what I do, some of the things that I'm learning.
The other thing I want to talk about, I have this little itch to be an entrepreneur besides consulting. Because when you're in the numbers and spreadsheets all day long, it gets a little mind-numbing. And I've been really drawn to working with product companies and more advanced manufacturing because my previous company was in industrial services with services and inventory and parts and all these things.
One of my clients is in e-commerce. And about a year and a half ago, I said to myself, You just need to know more about e-commerce. Like as a as a CFO, I was really good with the numbers. And I came in and I was like, okay, we need more revenue, we need better marketing. ⁓ and I started looking at courses that I could take to learn more. And then in this process, I said, Well, why not launch a product?
⁓ and learn that way. You could learn e-commerce, you could learn marketing. So I said, All right, I'm gonna try this. What what would I lunch? And they said, What's something you want? And ⁓ I said, you know what I've really been wanting is a travel cup that's glass. And every time I order them, they come with like a weird top or a silicone top, which I hate drinking out of silicone, feels so terrible. ⁓
And I hate drinking out of metal travel cups because they smell bad and they leak around your mouth and the mouth feels terrible. Anyway, so I've developed this. It's a glass travel cup with a glass top, silicone band to seal it, double wall glass on the bottom. It's called Siplux, if you want to check out my website. S-I-P-L-U-X dot com. And ⁓ I have been on a journey of learning.
⁓ designed production outsourced manufacturing in China, importing, navigating tariffs, and then launching a Shopify store, learning all the apps, the integrations, how it integrates to finance, and I think most importantly paid advertising, which is brand new for me in my career. I've been consuming every book and different things that I can read on this and
we're hitting a you forecast of six figures now with our monthly sales. So it's making progress. And I think this has been one of the most ⁓ curious parts of my career is that I've never been in a role where I launched something myself. I've always been facilitating other people and their products, their ideas. even in my family business, I was the one that brought
product or service to market, made sure the books were sound, our services were sound. But I've never been that creative role and learned marketing. So this has been something that's been really good for me and expanded my mindset, definitely made me a better CFO as I understand systems and architecture better and understand how to spend marketing dollars in turnaround situations where you do need to get revenue moving again.
I'm pretty excited about the expansion of my own education and and the product because I'm in love with it and I now have my sister working part-time for me, shipping out boxes. But if anyone has questions or or wants to more, you know, have dialogue or hear more about my practice, I'm happy to