One-On-One
Executive Coaching for Business Owners
You built the business. Now it’s running you. Tony DiSilvestro’s one-on-one executive coaching gives founders and CEOs a direct path to working less, leading better, and scaling with intention, with someone who’s actually done it.
Coaching For The Seat You're Actually Sitting In
Most business owners don't need more information. They need someone who's sat in their seat. Someone who knows what it costs to build something real, sign the front of the checks, and carry the weight when everything falls on your desk.
Tony has founded and scaled businesses across hospitality, construction, real estate, and multiple other industries, including growing Ynot Italian past the 8-figure mark. He's not teaching theory. He's coaching from 40+ years of running his own companies, making the same calls you're making right now, and figuring out what works and what doesn't the hard way.
One-on-one coaching with Tony is private. Direct. Built around your business, your team, your numbers, and your life outside the business.
What One-on-One Executive Coaching Actually Looks Like
Every engagement is built to move you forward on what actually matters. Here's how it works.
Diagnostic Start
Every engagement opens with an honest assessment of where the real bottlenecks are. Your team, your time, your numbers, and the decisions running through you that shouldn't be.
Private Sessions
Direct coaching calls with Tony, focused on the decisions in front of you right now. No group, no playbook template, no generic advice. Just the work that moves your business this month.
Structured Outcomes
Each session ends with decisions made, priorities set, and specific actions assigned. You don't leave with insight. You leave with a plan and a deadline.
Accountability Between Calls
Tony holds you to what you commit to, the same way you expect your team to hold their commitments. No excuses, no slippage, just forward movement week over week.
The Five Patterns That Keep Owners Stuck
Coaching engagements are built around the specific problems that stall growth, drain profit, or cost you your life. These are the ones that show up the most.
Breaking the Bottleneck
You Are The ProblemIf every major decision runs through you, your business has a structural problem, not a people problem. Coaching identifies where you're holding on too tight, then builds the systems and leadership around you so you can let go without everything falling apart.
Scaling Without Breaking
Growth With InfrastructureGrowth without infrastructure creates chaos. Quality slips, key people burn out, and margins shrink while revenue climbs. Coaching builds the operational foundation, the systems, the processes, and the team structure that lets your business grow without breaking under the weight of its own success. For owners needing a top-down rework, business transformation consulting runs alongside 1:1 coaching.
Building a Leadership Team
Leaders, Not Just ManagersYou can't scale what only you can lead. Coaching helps you identify who on your team is ready to step up, how to develop them, and what leadership development training looks like inside your specific organization. The goal isn't more managers. It's real leaders who own outcomes.
Owner Mindset & Decision-Making
Lead From The FrontThe decisions you make at your level set everything below it. Coaching sharpens how you think, how you prioritize, and how you lead under pressure, so you stop reacting to the business and start directing it.
Work-Life Balance That's Actually Real
Freedom By DesignFreedom was the reason you started the business. Coaching maps a real path back to it. Fewer hours, more presence, and a company that doesn't collapse the moment you step away for a week.
Coaching That Speaks Your Industry's Language
Coaching isn't one-size-fits-all. Tony's spent decades inside these industries, running businesses in several of them personally. The problems, the language, and the pressure are already familiar.
Hospitality & Restaurants
High-volume, high-turnover environments demand leaders who execute consistently at every level. Coaching helps hospitality owners build the team culture and operational standards that deliver a great guest experience, every shift.
Explore →Construction
Project-based businesses live and die by their systems and their people. Coaching helps construction owners build leadership layers, tighten job costing, and stop personally carrying every project from bid to close-out.
Explore →Real Estate
Whether it's a brokerage, a development firm, or a property management portfolio, growth creates new problems at every level. Coaching gives you the clarity and systems to scale without losing control of quality or culture.
Explore →Manufacturing
Thin margins, workforce turnover, and constant operational pressure. Coaching builds the leadership structure and process discipline that runs a leaner, more profitable operation, without you on the floor every day.
Explore →Healthcare & Wellness
Practice owners face a unique mix of clinical oversight, staffing complexity, and compliance pressure. Coaching gives you the structure to lead the organization without being the answer to every clinical and operational question.
Explore →Franchising
Multi-unit operators need systems that replicate across locations and leaders who can run each site independently. Coaching builds the infrastructure to grow the portfolio without growing your personal workload proportionally.
Explore →"Most business owners don't have a strategy problem. They have a leadership problem. Fix the leadership, the strategy takes care of itself."
Tony works with owners who are already successful on paper but running out of gas personally. Watch a few minutes of how he thinks before you book a conversation.
Questions Owners Ask Before Starting
Who is one-on-one executive coaching actually for?
It's built for founders, CEOs, and owner-operators running businesses that already work but have hit a ceiling the owner can't push through alone. Typically owners of companies past the startup stage who are stuck being the bottleneck for every major decision. If you're starting from zero, this isn't the right fit.
How is this different from a group program or mastermind?
Group programs are built for the average. One-on-one coaching with Tony is built for your specific business, your specific team, and the decisions you're making this quarter. There's no cohort, no curriculum to keep up with, and no sharing airtime. It's a private conversation focused entirely on moving your company forward. If the leadership team needs development as a group, business team coaching runs alongside or instead.
What kind of commitment does a coaching engagement require?
Engagements are structured around your schedule, but the work itself requires real commitment. You'll be asked to make decisions, implement changes, and hold your team accountable between sessions. Owners who show up half-in get half-results. We talk through scope and cadence during the discovery call.
Does Tony coach owners in specific industries?
Tony has personal operator experience in hospitality, construction, real estate, and multi-unit businesses, and has coached owners across manufacturing, healthcare, franchising, and retail. The fundamentals of scaling a business, building leaders, and getting out of the operator seat apply broadly. The tactics get industry-specific once we start working together.
How do I know if this is the right next step?
The easiest way is a discovery call. No pitch, no pressure. You share what's going on, Tony shares an honest read on whether coaching is the right fit, and you decide from there. If it's not the right fit, he'll tell you.
Your Business Should Give You Freedom, Not Take It
If you're working 60+ hours a week, missing the moments that matter, and wondering whether the sacrifice is worth it, the answer isn't to work harder. It's to build smarter.
One-on-one executive coaching is the fastest path to clarity, accountability, and real progress. No group. No program. Just you, Tony, and the work that actually moves the needle. See all of Tony's business coaching options or entrepreneur coaching for earlier-stage founders.
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