Operational Scalability: Jayson Koss and Ed Mileto Of Eightfold Ventures On How To Set Up Systems, Procedures, And People To Prepare A Business To Scale
Strong Leadership Team. You don’t need three data nerds, none of whom like to talk to customers. What you need are different but complementary experiences and viewpoints. We help create that between ownership and team leaders.
In today’s fast-paced business environment, scalability is not just a buzzword; it’s a necessity. Entrepreneurs often get trapped in the daily grind of running their businesses, neglecting to put in place the systems, procedures, and people needed for sustainable growth. Without this foundation, companies hit bottlenecks, suffer inefficiencies, and face the risk of stalling or failing. This series aims to delve deep into the intricacies of operational scalability. How do you set up a framework that can adapt to growing customer demands? What are the crucial procedures that can streamline business operations? How do you build a team that can take on increasing responsibilities while maintaining a high standard of performance?
In this interview series, we are talking to CEOs, Founders, Operations Managers Consultants, Academics, Tech leaders & HR professionals, who share lessons from their experience about “How To Set Up Systems, Procedures, And People To Prepare A Business To Scale”. As part of this series, we had the pleasure of interviewing Jayson Koss and Ed Mileto, founders of Eightfold Ventures.
Eightfold Ventures is a consultancy/venture capital fund based in Delray Beach, Florida. Its portfolio is limited to eight active companies — all specialty brands poised for exponential growth within their unique segments. Eightfold Ventures is committed to deep operational engagement, not just capital, by installing step-by-step, proven growth playbooks into each function of the business. Eightfold provides insights and guidance based on its founders’ personal entrepreneurial journeys, in support of companies in theirs.
Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
We were two guys who had recently gone through highly successful exits: Ed with Perfect Practice Golf and Jay with Delivery Dudes. We had done something exceptional and wanted to keep that going, but we didn’t just want to invest in businesses or go the traditional VC route. We wanted to install our proven system into businesses primed for big growth. So, we decided to start Eightfold Ventures, a consultancy/venture capital fund based in our hometown of Delray Beach, Florida. We don’t just invest funds, we work side by side with these businesses to scale them, using our proven operations system and growth strategies.
What do you think makes your company stand out? Can you share a story?
We’ve both been in the trenches. For example, Jay started Delivery Dudes off his moped with just the cash in his pocket. And when DoorDash came in and killed all the regional businesses, Jay fought back. He got meetings with Google. He stood on a stage in Chicago and called DoorDash out directly. He survived — and thrived — when no one else did. Ultimately, he ended up in the same rooms as Softbank and DoorDash and these giant venture-backed machines, so he understands both sides of the capital game — a very rare thing. His insights into capital use are unparalleled: How important is capital in the war chest? When and how much should you use? These are the kind of things you need guidance on if you want an eight-figure company.
Ed’s basically a legend in the e-comm golf industry. He did what every e-commerce business wishes they could do. After selling only 25 Perfect Practice mats at the PGA show in 2019, they sold 10,000 at that very same show 12 months later. After that, ecommerce took off and they had big retailers like Dick’s Sporting Goods and Costco knocking at their door. How did he do it?
As Ed likes to say, “There’s no silver bullet, you have to do everything right.”
To make Perfect Practice what it was, Ed put a team into place to execute a strategic operational scalability system. That’s where most businesses trip up. They don’t really know what to do day-by-day to get where they want to be.
Something else that sets us apart is our belief that good business is about more than money…it’s about creating — and sustaining — a brand that fills a real need in the marketplace, something that people really gravitate toward. We want our companies to achieve a successful outcome, sure, but we also want them to enjoy the trek getting there.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
- Acceptance — whatever comes your way, you need to be in state of acceptance so you can get through it. Learning to overcome adversity is one of the toughest — and most valuable — lessons in business.
- Patience — except on the rarest of occasions (ok, maybe never), success does not simply come overnight. Patience is a virtue, as the saying goes, and it will greatly benefit entrepreneurs to enjoy the wins when they come in — no matter how long it takes to get there.
- The relentless pursuit of — well, we probably shouldn’t use that trademarked tagline. But being relentless in your quest to build a successful company goes without saying. If you don’t fully believe in it and put 1000% of your efforts behind it, it will fail. For us, failure is not an…yeah, you know that one.
Thank you for all that. Let’s now turn to the main focus of our discussion about Operational Scalability. In order to make sure that we are all on the same page, let’s begin with a simple definition. What does Operational Scalability mean to you?
Most companies are really good at one thing. And they take that as far as they can. But what happens after that? Where do they go? That’s why people come to us.
The thing is, if you want to grow in the long term, you have to know how and have a concrete game plan. And most businesses don’t have a long-term growth system, they have a “get through the day system.”
Each week we look at parts of the business most owners don’t fully understand and ask: Where can we press? What are the purchasing trends? What are our customers doing? We assess all of this and put together a plan for that business to grow.
Which types of business can most benefit from investing in Operational Scalability?
Is there really a business out there who wouldn’t benefit from more organization and getting access to a successful playbook…? Unless they have no desire to grow… which is completely crazy, of course.
The truth is businesses that are just scrambling with no proper systems in place just simply won’t survive. Efficiency = profitability, plain and simple.
Why is it so important for a business to invest time, energy, and resources into Operational Scalability?
The big problem we see among most founders is “shiny object syndrome.” So, we eliminate it. As author and business strategist Patrick Lencioni has said, “If everything is important than nothing is important.” And that’s never been truer than in scaling a business. Every company we work with is required to set — and reach — three key goals each quarter…that’s it. Getting distracted or sidetracked or spinning your wheels on things that aren’t driving revenue is a company killer.
In contrast, what happens to a business that does not invest time, energy, and resources into Operational Scalability?
Typically, those companies just tread water. They’ll end up hitting an operational ceiling with revenue and growth. The team becomes messy, good talent will quit, partnerships unravel and go south, and they’re just perpetually ‘stuck’ on a hamster wheel until something goes off track and the whole thing either jams or spins out of control. That’s not a winning formula, clearly.
Can you please share a story from your experience about how a business grew dramatically when they worked on their Operational Scalability?
Sure. One of our partners is golf technology brand. When they came to us, it was three guys who had a great idea but were struggling to figure out what to do with it. Two of the partners were part-time and one of them was basically carrying the company on his back…they were just stuck.
For two years revenue remained flat. Decent, but flat. We brought them into Eightfold and within six months they were growing so fast the two other founders quit their jobs and came on full-time. They’ve increased revenue by 600% since they started with us and this is just the beginning. And, their product, The Caddie, just won Best New Product of 2025 at the PGA show.
Based on your experience and success, what are the “Five Most Important Things A Business Leader Should Do To Set Up Systems, Procedures, And People To Prepare A Business To Scale”?
Here are five things that we believe are necessary for every company who truly wants to experience sustained growth:
1 . Product/Market Fit. There must be proof that the product is something that people want.
2 . Growth Margin. You must be able to sell your product at a substantial profit. This is where businesses kill themselves. Most e-commerce retailers woefully underestimate this. Healthy growth margins are essential.
3 . Strong Leadership Team. You don’t need three data nerds, none of whom like to talk to customers. What you need are different but complementary experiences and viewpoints. We help create that between ownership and team leaders.
4 . Pioneering Product. How do you stand out? The product needs to have something interesting, unique, pioneering, or revolutionary about it to compete in an extremely competitive marketplace.
5 . Sound Financials. Companies need to have a reliable bookkeeper and a good CPA at minimum. We highly encourage financials are regularly compiled, reviewed or audited. This will make any eventual exit that much easier.
What are some common misconceptions businesses have about scaling? Can you please explain?
Everyone runs a business because they want to make money or create some kind of exit event. But how do you get there? Small, private businesses should operate just like a large, public company does — with accountability, transparency, due diligence, etc.
Many entrepreneurs have had game-changing ideas, but without a system, their financial and exit goals will likely become just a pipe dream.
How do you keep your team motivated during periods of rapid growth or change?
It’s easy to stay motivated when you see progress. As corny as it sounds, progress all comes down to staying focused on core values. Every week we have systems in place to check in and say “Hey, are we being loyal to who we are?” Weekly check-ins are essential.
And this applies to employees’ workloads too. There must be a system for communicating and checking in: Is your workload manageable…or do we need to take some stress off your back? If your team is going through stressful growth, then reward them with spot bonuses, paid time off, even a profit-sharing opportunity, or other incentives to show how much you value the work they do.
But always be thoughtful and appreciative. That’ll often reap far more rewards than a new title and a gift card to Starbucks.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
We have a couple of quotes we like, and we couldn’t decide which one, so…
“Indecision may or may not be my problem.” — Jimmy Buffett
“Would you rather be a Ferrari or a Volkswagen? Make your choice and get ready to ride.” — A former boss
Our mantra is READY. FIRE. AIM. Just take your shot. Entrepreneurship is about failing as fast as possible (because it’s likely to happen) but to keep on firing…you’ll get a direct hit eventually, as long as you don’t give up and have the tools it takes to succeed.
How can our readers further follow your work online?
We’re at eightfoldventures.com and LinkedIn @eightfold-ventures
(https://www.linkedin.com/company/eightfold-ventures/)
Thank you so much for sharing these important insights. We wish you continued success and good health!
Operational Scalability: Jayson Koss and Ed Mileto Of Eightfold Ventures On How To Set Up Systems… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.