I’m Anthony Spitaleri.

Business experience

I’ve built businesses of my own and I’ve built the inside of someone else’s. The second one taught me more, because I was responsible for the parts that break when a company grows faster than its structure.

I started my first business at 18, repairing computers. From there I sold aircraft parts and brokered aircraft sales, then spent four years as a flight attendant at Delta Air Lines out of New York while I held my own pilot’s license. Then real estate, where I opened my own brokerage, sold my first million dollar property and ran a property management company alongside it. I left that brokerage while it was producing to help build the firm.

I was part of a professional services firm from its early days, eventually as vice president, and helped grow it from a small team to more than a hundred employees across two countries. The firm was later named to the Inc. 5000. My part was the operation behind the service: the people, the money and the systems that let the firm grow past any one person.

Here is the work itself, because the specifics are the only part of it that’s useful to you.

Sales. I worked to grow sales by finding the gaps between a new lead and a signed client, fixing them and then scaling what worked, including tying the team’s pay to performance and growing the team as the firm expanded.

Hiring. I set up the hiring and grading process and hired across the business, from assistants and sales staff to operations managers and leaders. I also worked on pay plans, bonuses and benefits.

Money. I handled the firm’s finances as it grew: payroll in two countries, budgets and forecasts, working with a fractional CFO and an accounting team for the second country.

Systems. I put KPIs in place for every area of the business and led the move to a new CRM and a cloud phone system, working with our team and the vendors, along with office space and technology requirements.

Expansion. I helped replicate the operation in a second country. The team there started as contractors paid through international payment platforms. We then set up a local company so they could become employees with benefits, which came with a different set of HR rules than at home.

Leadership. I began researching firms we could acquire and started designing a compensation package for the leadership team.

Why that matters in coaching

I don’t assume that because something was right for that firm, it’s right for your business. Your customers, resources and goals matter.

The work is on your business: where sales stall, who to hire next, what the numbers are telling you, which systems to change and whether to expand. When a decision needs an accountant, a lawyer or another specialist, we work out what to bring them and when.

I coach because the decision layer is where I was most useful, and where most owners are most alone. Not because I want to sell you the company I helped build.

What I bring is experience of connected decisions. A hire changes cost and capacity. A pay structure changes expectations. A new system asks people to work differently. We can examine those connections before you commit, then keep working with what actually happens.

I’ve been coached myself since 2019, and I became a certified coach in 2025.

What we’re building now

We’re building this coaching company with AI. I’m interested in what it can take off my plate, where it still needs my judgment and whether the result makes the business better.

I run my own businesses on an operating system I built: more than a hundred scheduled automations and dozens of agents that handle research, preparation, publishing and follow up, with my judgment on anything that matters.

I want to do useful work, build a strong business and have time and energy for my life outside it. Those goals belong in the decisions I’m making now.

See what I’m working through