Entrepreneur · Operator · Builder

Jonathan Shilalis

Serial entrepreneur who builds, scales, and exits businesses. From $185M+ in real estate to product invention to AI consulting — I turn ideas into revenue and chaos into systems.

Jonathan Shilalis - Serial entrepreneur, operator, and executive leader

Boca Raton, FL

Jonathan Shilalis

0

Businesses Built

$0M+

In Transactions

0+

Agents Recruited & Trained

Top 0%

First OpenAI Users

What I Bring

What I Bring to the Table

A rare combination of entrepreneurial grit, technical depth, and hands-on execution across multiple industries.

I don't just have ideas — I build them. Every business I've started was built from zero with my own hands.

Builder & Scaler

Built 5 businesses from the ground up across real estate, hospitality, product development, AI consulting, and business brokerage. I don't just strategize — I execute.

AI-First Operator

Among the first 1% of OpenAI users. I implement AI into real businesses — not theory, not demos. Actual revenue-generating AI workflows for real companies.

Mechanically Inclined

Can fix or build just about anything. From construction projects to backend systems to factory negotiations — I understand how things work at a fundamental level.

Licensed Professional

Licensed Real Estate Broker (FL, MA, ME) and Licensed Business Broker (FL). Trusted with the largest transactions in people's lives.

Results-Driven

$185M+ in closed transactions. Hundreds of 5-star reviews. Patents filed. Websites built. Every venture has measurable outcomes — I don't dabble, I deliver.

Financial Freedom

My hard work has provided the luxury of choice. I work because I'm passionate about what I do, not because I have to. That means full commitment, zero desperation.

DISC Profile

The Strategic Implementer

A Tony Robbins DISC assessment reveals a C/D blend — someone who combines deep analysis with decisive action. Purpose-built for leadership and execution.

Strategic Implementer

C/D Blend — Deep Analysis + Decisive Action

Natural Score■ solid = natural · ■ ghost = adaptive (at work)
Conscientiousness (C)
7384 at work

Quality-obsessed systems thinker — jumps to 84 in professional settings

Steadiness (S)
5866 at work

Reliable, calm under pressure, patient with processes

Dominance (D)
5545 at work

Decisive when needed — lets quality lead over ego at work

Influence (I)
1916 at work

Results speak, not charm — substance over schmooze

Key Motivators

Theoretical: 71 (deep learning) · Economic: 68 (ROI-focused) · Power: 66 (authority) · Altruistic: 8 (zero BS — tells the truth)

Quality That Scales

C at 84 in professional settings means clients and partners get thorough, bulletproof work — not half-baked advice.

Deep Researcher

Theoretical motivator at 71 = learns everything before acting. Clients trust expertise, not charm.

Multi-Project Juggler

5 businesses running simultaneously proves the ability to manage multiple accounts and initiatives.

Tells the Truth

Altruistic at 8 = zero BS. People hear what they NEED to hear, not what they want to hear. That builds real trust.

Born Enabler

High Theoretical motivator = love of learning AND teaching. Enablement is a calling, not a job.

Substance Over Schmooze

Low I means earning trust through proof and results, not glad-handing. That's more effective in every industry.

Portfolio

5 Businesses. One Builder.

Serial entrepreneurship isn't a buzzword — it's a lifestyle. Each venture sharpened a different skill set and proved I can build in any industry.

10x AI Consulting - portfolio image
2024 – Present

10x AI Consulting

Helping businesses 10x their results with AI

AI implementation consulting that transforms how businesses operate. From prompt engineering to full AI workflow design, helping executives understand and leverage artificial intelligence for measurable results.

10x ad ROI for clients
C-suite AI training & adoption
Rapid client acquisition systems
Visit Website
Shilalis Real Estate - portfolio image
2011 – Present

Shilalis Real Estate

$185M+ in real estate transactions

Founded and grew a real estate empire from scratch. Built a team of 150+ agents, managed multi-state operations, and sold the Massachusetts brokerage in 2025. Now active in Florida market.

$185M+ in transactions
150+ agents hired & trained
Sold MA brokerage in 2025
Visit Website
VacaMojo - portfolio image
2020 – Present

VacaMojo

Highest-rated vacation rentals on Airbnb

A portfolio of premium vacation rental properties earning top ratings on Airbnb. Built remote management systems and leveraged AI for guest communication, pricing optimization, and operations.

Hundreds of 5-star reviews
Highest-rated Airbnb properties
AI-powered remote management
Nessa Bottles - portfolio image
2025

Nessa Bottles

From concept to product — patents, trademarks, and beyond

Invented a product from the ground up. Navigated patent filings, trademark registrations, factory negotiations, and built the entire e-commerce operation. Proof that innovation never stops.

Patents & trademarks filed
Factory negotiations completed
Full e-commerce buildout
Visit Website
Sun Biz Broker - portfolio image
Jan 2026 – Present

Sun Biz Broker

Business brokerage in the Florida sunshine

Newest venture bringing real estate acumen to business brokerage. Helping entrepreneurs buy, sell, and transition businesses with the same data-driven approach that built a $185M real estate portfolio.

Business buy/sell facilitation
Market opportunity analysis
Entrepreneur-focused approach
Visit Website
Technical

AI Expertise

From the first wave of GPT to deploying AI agents at scale — a timeline of staying ahead of the curve.

AI Journey

2020

Early Crypto/DeFi Adopter

Recognized disruptive technology patterns early and built expertise in emerging tech ecosystems.

2022

First 1% of OpenAI Users

Among the earliest adopters of GPT and AI tools, immediately seeing the business transformation potential.

2023

AI Consulting Launch

Started helping businesses implement AI workflows, achieving 10x ad ROI for clients.

2024

Enterprise AI Consulting

Launched 10x AI Consulting. Training C-suite executives and achieving 10x ad ROI for clients.

2025

Full AI Integration

Every business now runs on AI. From real estate to vacation rentals — AI-first operations across the board.

2026

AI-First Everything

Building websites, automating workflows, deploying agents. Helping businesses transform with AI daily.

Technical Skills

LLM Workflow Design95%
AI Agent Deployment90%
Prompt Engineering95%
Business Process Automation90%
Full-Stack Development80%
E-Commerce Platforms85%

Additional Expertise

  • Crypto & DeFi protocols (early adopter)
  • Website development with backends
  • Factory negotiations & supply chain
  • Mechanically inclined — can fix or build anything

A personal message about my AI journey

Get in Touch

Let's Build Something Great

Whether it's a partnership, opportunity, or just a conversation — I'd love to connect.

Contact Information

“Helping people has led to every business I've ever built.”

With 5 successful businesses and financial freedom, I choose to work on things that excite me and create real impact.

Send a Message

Your message will be saved securely. I'll respond as quickly as possible.