ANTHONY L. MAY

I bring more than 30 years of experience to building businesses, developing opportunities and turning ideas into sustainable ventures.

My work includes ownership, partnerships and strategic contributions across a diverse portfolio. Each venture has its own direction, supported by a consistent approach: a clear purpose, the right people and a practical path to lasting value.

I focus on building strong teams, sound systems and businesses that can grow beyond any one person. The goal is to create lasting value and more freedom for the people behind them.

For more than a decade, I worked tirelessly for a company. Then I was mistakenly copied on an email discussing my termination. From what I read, they were looking for a reason to fire me because I was "making too much money."

That moment changed how I thought about my future. I had invested years of work in that business, yet decisions about my livelihood were being made without me. I decided I wanted more control over my time and my destiny.

I grew up poor, in a broken household. Having choices matters to me. I am a father, grandfather, and brother, and I share my life with an incredible fiancée. I wanted time to be present for the people I love, the ability to travel, and the freedom to be there when family needed me.

Today, freedom can be a hike somewhere new, a quiet coffee looking at the ocean, or being able to leave when family calls. It also means choosing the work and relationships I want to invest in.

I still work long hours. I love building businesses, and I am still learning to protect the time I worked so hard to gain. Nimblepreneur is where I share both the possibilities and the lessons.

The advice that shaped how I build

“In business, don't do anything here that you can't also do when you're a million miles away.”

My dad told me that. It became the cornerstone of how I conceive and build businesses.

I think about who can lead, how decisions will get made, and how customers will be served when I am somewhere else. My captains, our relationships, and clear responsibilities make that possible.

Build income. Build systems. Build freedom.

The Hard Parts

Making payroll. Letting someone go. Realizing you trusted the wrong person. Starting over after a loss. These decisions are part of running a business. I’ll talk about them here, along with the people, systems and choices that make the work worthwhile.

You don't have to move abroad to begin. You can start by giving your business a stronger foundation and yourself more choices.

BUSINESS · AI · MONEY · FREEDOM

No greater than, no less than.

Nobody builds alone. A business needs customers, people who can execute, and partners who bring different strengths. Someone may know more than me in one area and less in another. That does not make either of us worth more. Trust grows when we treat people accordingly.

Develop people who can lead.

I call my trusted leaders my captains. We agree on the goals, make responsibilities clear, and stay in communication. They need the authority and support to make decisions, not just a list of tasks.

Make the business work.

Know where revenue comes from, what delivery costs, and what needs your attention. Use systems and technology, including AI when it helps, to make the work more reliable.

Create room for your life.

Where you live, who you spend time with, and how you work should be choices you can build toward. That takes effort, responsibility, and people you trust.

Opportunity and judgment

Spotting an opportunity is only the beginning. I look at who it serves, whether the business can work and what it will take to sustain it. Experience has taught me to pair ambition with judgment: ask hard questions, understand the risks and know when to move forward.

Recognizing a market early

Helping companies identify niche opportunities has long been part of my work. I owned ModelingPages.com in the early 1990s and acquired hundreds of podcast domain names in the early 2000s.

I conceived GridToday and a conference around grid computing after seeing where the technology was heading. My work in high-performance computing publishing taught me to connect an emerging market with the people and businesses it could serve.

Through Men for a Cause, I taught men that they could get breast cancer too, so they could better understand and support the women in their lives. Support has always been the thread running through my work: helping people understand what others face and giving them practical ways to show up for one another.

The lesson that changed how I evaluate opportunity

With San Diego Tour Coupes, I pushed to launch quickly, partly because a competitor might be entering the market. Our vehicles looked like cars but were classified as motorcycles, and we faced questions from local authorities.

Within 18 months, we were out of business. I lost my life savings at the time.

That changed how I think about speed. Recognizing an opportunity is only the beginning. You also need to understand the operating conditions, the risks, and whether you have the resources to stay the course.

Before the plane ticket, make a plan.

Heading abroad for the holidays, spending winter in Mexico, or checking in on parents living overseas? Does someone you trust know where your important information is if you cannot answer?

I kept seeing posts in expat groups trying to find someone's next of kin after a death abroad. I couldn't stop thinking about the family who hadn't been reached.

That led me to create The American Abroad Protection Kit: a way to organize important information and give a trusted person somewhere to start when you cannot answer.

Your household receives eight PDFs: a 113-page workbook in three formats, trip essentials, emergency action cards, a wallet card, a U.S. connection guide, and Start Here instructions.

Launch offer: $29 for the first 100 paid household purchases. Then $49. Digital download only. Planning resources, not insurance or emergency response. No app access or automated alerts are included.

Holiday gifts from SHAVA

As SHAVA, I explore identity, history, faith, and the questions that stay with me. Art gives those ideas another form.

Discover holiday works including Hot Chocolate For Santa, A Christmas Eve (Waiting for Santa), and Santas Helper (Dorothy Dandridge), alongside portraits and other pieces with a story to tell.

A Christmas Eve (Waiting for Santa)

Artist: SHAVA

An artistic commentary and recontextualization of Gil Elvgren's 1954 work of the same name, exploring the historical exclusion of Black women from mid-century pin-up art.

Choose from the print formats and sizes available on the SHAVA store. Check current production and delivery estimates before ordering for a holiday date.

Writing is another part of my life. I have at least five children's manuscripts waiting to be published, along with Everything You Should Know But Your Daddy Didn't Tell You, a practical guide for young men navigating life.

I am also working toward completing a longer book about loving yourself in 2027. These writing projects are in progress and are not yet available to buy.

For select business, strategy, partnership, media and advisory conversations.

Tell me what you’re building, why you’re reaching out, and what a useful conversation would accomplish. Include your website and relevant timing.

My team and I review inquiries for fit. Paid advisory or implementation work is scoped separately; an inquiry does not commit you to an engagement.

My work in wellness brings business, technology and access to care together through SWONKDOG.

I focus on building responsible businesses and the systems behind them. Clinical decisions, testing orders and interpretation belong to licensed providers.

Explore the broader project at SWONKDOG.

Business • AI • Money • Freedom

I’ll share what I’m building, lessons from running businesses, AI tools worth trying, and ways to make more room for life outside work.

Join for Nimblepreneur news, new content and occasional product updates.

“In business, don’t do anything here that you can’t also do when you’re a million miles away.”

My dad told me that. It became the cornerstone of how I build: systems, trusted leaders, clear responsibilities, and technology that helps the work continue when I’m somewhere else.

Build income. Build systems. Build freedom.