This interview is with Ronald Osborne, Founder at Ronald Osborne Business Coach.
Ronald Osborne, Founder, Ronald Osborne Business Coach
To help Featured readers get to know you, how do you describe your coaching focus and the types of small businesses you work with?
My coaching focus sits squarely on helping service-based business owners break through the operational bottlenecks that keep them stuck between 150K and 500K in annual revenue. That transition point where you have one or two employees and want to scale to five or more is where most founders hit a wall because they know how to do the work but struggle to teach others to replicate their quality. I specialize in building system-dependent operations rather than person-dependent ones, which means creating documented processes, performance tracking frameworks, and increasingly AI-driven workflows that let owners step back from daily execution without watching quality collapse.
The businesses I work with span over 50 industries at this point, though my strongest results come from construction trades like roofing and hydraulic repair, medical practices including chiropractors and assisted living facilities, and general service companies where the founder built something through sheer hustle but lacks the infrastructure to scale. I charge a modest monthly retainer with a performance fee tied to revenue growth because I believe coaches should have skin in the game alongside their clients. If I cannot move the needle on your business within six months, something is fundamentally broken in our approach and we need to fix it fast. That accountability structure keeps me honest and keeps my clients focused on execution rather than endless strategy sessions that never translate into results.
What key experiences—from your military telecommunications background to your MBA in finance—shaped your path into business coaching and international work?
My path into coaching started in the Australian Army where I served in signals after an injury derailed my special forces aspirations. Working alongside brigade commanders during operations taught me something that changed how I view leadership forever. These senior officers making life and death decisions were human beings who made mistakes and did not always have the answers. That realization stripped away the mystique around success and showed me that execution and adaptability matter far more than having a perfect plan. When I transitioned out and built my telecommunications company to 30 employees and 5.7 million in revenue before turning 30, I learned firsthand what breaks when you scale. Systems documentation, cash flow management, hiring the right people for roles instead of hiring friends. Every painful lesson cost me real money, including one hiring mistake that set me back a quarter million dollars.
The MBA specializing in finance gave me the technical vocabulary and frameworks to communicate with accountants, attorneys, and investors across different markets. But honestly the real education came from operating internationally and discovering that business culture varies dramatically by region. Americans will trust you quickly if you demonstrate results. Australians are more hesitant to engage coaches. Middle Eastern and European clients prioritize relationship and character over your track record. Understanding these differences lets me adapt my approach depending on who I am working with rather than forcing a one size fits all methodology that ignores how people actually make decisions in different parts of the world.
When you begin with a new small business, what first-principles diagnostic steps do you take to pinpoint growth bottlenecks?
The first thing I do with any new client is get them to track their week minute by minute. Not what they think they do but what they actually do. Founders will tell me they are too busy and need to hire someone, but until I see where their hours go I cannot diagnose anything accurately. We upload this data into AI systems I have built specifically for pattern recognition, and within days we can identify exactly where time is bleeding. Maybe they spend 15 hours weekly on lead generation tasks that could be automated or outsourced. Maybe they are doing admin work that a virtual assistant could handle for a fraction of their hourly value. This exercise alone often reveals that the problem is not capacity but allocation.
From there I examine three core areas in our initial three to four hour onboarding session. First is cash flow, specifically payment terms and whether clients or contractors are actually adhering to agreements. I have seen countless businesses bleeding money simply because they are afraid to enforce 90 day terms that have stretched to 110 days. Second is pricing, where I conduct competitive research by calling competitors directly to understand market rates. Most owners I work with are undercharging by 10 to 50 percent because they have never systematically studied what others charge for equivalent services. Third is employee output, measuring actual productive hours against paid hours. Once I have clarity on these three areas I can build a 12 month roadmap with specific measurable objectives rather than vague goals that never translate into action.
Building on that, how do you use financial frameworks to improve cash flow, budgeting, and forecasting in a way owners can apply quickly?
The fastest cash flow improvement I implement has nothing to do with spreadsheets or forecasting models. It starts with pulling out the contracts and checking whether payment terms are actually being honored. I work with a lot of contractors and service businesses where the agreement says 90 days but the paying party has quietly stretched it to 110 or 120 days to buffer their own books. Most owners are intimidated to push back because they feel like they are biting the hand that feeds them. So I step in, review the contract with my attorneys if needed, and we send a firm but professional notice demanding adherence to the original terms. That single action can free up tens of thousands in working capital that was just sitting in someone else’s account.
For ongoing management I use a 12 month cash flow template I built specifically for contractors and service businesses that tracks receivables, retention amounts, and projected gaps before they become emergencies. The framework is simple enough that owners can update it weekly in under 20 minutes. I teach clients to forecast based on three scenarios. Worst case where deals fall through and payments delay, expected case based on current pipeline, and best case if everything closes on time. Running all three prevents the dangerous optimism that kills businesses when reality hits harder than expected. The owners who actually update their numbers weekly can see cash crunches coming 60 to 90 days out, which gives them time to adjust spending, chase receivables harder, or arrange financing before desperation sets in.
Speaking of teams, what practical methods have you used to reduce turnover and build a culture of accountability?
The biggest accountability killer I see is when owners cannot clearly explain what success looks like for each role. Employees drift when expectations are vague, so the first thing I implement is weekly performance tracking where every team member documents three specific objectives they committed to, whether they executed, what roadblocks they hit, and how they plan to overcome them. This is not micromanagement but clarity. When someone writes down their own commitments and reports on them weekly, accountability becomes self generated rather than imposed from above. I upload all this data into AI systems that help identify patterns over time, so after a couple months we can see exactly where each person consistently struggles and address root causes instead of symptoms.
On the compensation side, I learned from my telecommunications company that hungry workers want their income tied to output not just hours. I paid base rates as required by law but built custom software that let employees track their productivity and earn significantly more based on what they actually produced. Some of my team members hit 200K annually because their pay reflected their effort. The other non negotiable is leading from the front. I refused to ask employees to do anything I would not do myself, including turning down lucrative mobile tower work because the radiation exposure was something I was not willing to accept personally. Workers notice when owners share risk and discomfort with them. That consistency between words and actions builds loyalty that no bonus structure alone can match.
Drawing from your study of 675 entrepreneurs, how do you help clients sharpen their niche and position themselves as premium providers?
Working with over 300 business owners across more than 50 industries has shown me that most struggle with positioning because they try to appeal to everyone. The contractors and service providers I coach often describe themselves in generic terms that make them indistinguishable from competitors. A roofer says they do quality work at fair prices. A chiropractor says they provide personalized care. None of this means anything to a potential client scanning options. The shift to premium positioning starts with identifying the specific problem you solve better than anyone else in your market and being willing to let go of customers who fall outside that focus. When I helped Air Force Roofing scale from 100K to million annually, part of that growth came from narrowing their target rather than broadening it.
The practical method I use is competitive research that most owners skip entirely. I have clients call their competitors directly posing as potential customers to understand exactly what others charge and how they present their services. This intelligence reveals gaps in the market where you can position as the premium option. Almost every client I work with discovers they are underpricing by 10 to 50 percent simply because they never studied the landscape. Once you know the top competitors charge significantly more for comparable work, raising your prices becomes a logical business decision rather than a leap of faith. Premium positioning is not about being expensive for its own sake but about matching your price to the actual value you deliver and communicating that value clearly.
As services scale, what process do you follow to turn one-on-one work into group programs without losing quality?
The foundation for scaling any service without sacrificing quality is documentation that exists independent of you. When I built my telecommunications company to 30 employees, the breakthrough came from creating detailed SOPs and custom software that captured exactly how work should be done. The knowledge could not live only in my head or in one key employee who might leave. I apply the same principle when helping clients transition from one on one delivery to group formats. Before you add a single person to a group program, you need every repeatable element of your process documented in video, written guides, or templated frameworks. The diagnostic questions you ask, the sequence of steps you follow, the common problems and their solutions. All of this becomes curriculum that delivers consistent value whether you are in the room or not.
The mistake most service providers make is trying to scale by simply adding more people to calls without restructuring the delivery model. What actually works is identifying which elements require your direct involvement and which can be handled through peer accountability, recorded trainings, or structured assignments between sessions. I use weekly performance trackers with all my clients where they document objectives, execution, setbacks, and wins. This data feeds into AI systems that help identify patterns across the group, so I can address common struggles in group settings while reserving one on one time for issues that genuinely require individual attention. The hybrid approach lets me work with 15 to 25 clients simultaneously without the quality collapse that happens when coaches just pack more bodies into the same format they used for individual work.
To reinforce trust, how do you collect and use client testimonials so they translate into measurable business growth?
The testimonials that actually convert prospects into clients are the ones tied to specific numbers rather than vague praise. When I helped Mr. Hose generate 51,000 dollars in additional revenue over four months or took Air Force Roofing from 100K to 1.5 million annually, those figures tell a story that generic statements about great coaching never will. I collect these results as part of my normal tracking process since every client has weekly performance data feeding into our systems. When we hit milestones, I ask for a brief testimonial while the win is fresh and the specifics are clear in their mind. The request comes naturally because they are already documenting their progress and can see exactly what changed.
The strategic use matters more than volume. I match testimonials to the objections prospects typically raise during discovery calls. Someone worried about whether coaching works for their specific industry sees a case study from a similar business. Someone skeptical about ROI sees the Sunny Hills story where we took an assisted living facility from nearly closing down to opening a third location. I place these strategically on landing pages, in email sequences, and reference them directly in sales conversations when relevant concerns surface. The measurement side is straightforward. I track which testimonials appear on pages that convert versus those that do not, and I note which case studies I mention in calls that close versus calls that stall. Over time patterns emerge showing which proof points resonate with which types of prospects, and I lean harder into what actually moves people to action.
For sustainable growth, how do you coach owners to step back from day-to-day operations while keeping the business performing?
The transition from operator to owner starts with brutal honesty about what you actually do every day. I have every client track their week minute by minute because what founders think occupies their time rarely matches reality. Once we have that data, we categorize tasks into three buckets. Work only you can do, work someone else could do with proper training, and work that should not exist at all. Most owners discover they spend 60 to 70 percent of their hours on tasks that fall into the second and third categories. The goal is systematically eliminating your involvement in those areas through documented processes, trained employees, or increasingly through AI automation that handles repetitive work without adding payroll.
The critical mistake I see is owners who delegate tasks without transferring the knowledge required to maintain quality. When I scaled my telecommunications company, I built custom software and detailed SOPs that captured not just what to do but why each step mattered and what quality standards looked like. My employees could reference these systems instead of constantly asking me questions. The second piece is building accountability structures that do not require your daily presence. Weekly performance trackers where team members document their own objectives, execution, and obstacles create self management rather than dependence on you hovering over them. I still contact my coaching clients every couple of days but that is a quick check in not micromanagement. The owners who successfully step back are the ones who invested months building infrastructure that runs without them rather than just hoping employees figure it out on their own.
Thanks for sharing your knowledge and expertise. Is there anything else you’d like to add?
The one thing I wish more business owners understood is that the challenges you face at 150K are completely different from those at 500K, which are different again at a million. A coach who has not personally navigated each of those stages cannot recall the sleepless nights staring at the ceiling wondering how payroll gets covered next week. I only work with clients whose goals align with territory I have actually walked through myself. When someone comes to me wanting to build a 30 million dollar company, I tell them to find someone else because I have never operated at that level and would be guessing rather than guiding.
The other truth nobody wants to hear is that balance is a reward you earn after building something, not a strategy for building it. Every successful founder I have spoken with laughs when asked about their twenties because they did not have a life outside of work. I worked seven days a week averaging 12 hour days for years, which meant I had roughly 100 extra working days annually compared to someone chasing balance at 40 hours weekly. That compounds fast. If you are still in the building phase and wondering why progress feels slow, look honestly at whether you are actually outworking your competition or just hoping talent alone carries you through. The market does not care about your potential. It only rewards execution.