Real Estate Broker · Investor · Entrepreneur

Jonathan Shilalis

Real estate broker and investor who builds, scales, and exits businesses — with $228M+ in total real estate volume, a personal portfolio of multifamily developments, fix-and-flips, and short-term rentals, and ventures spanning AI software, product invention, and business brokerage.

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Boca Raton, FL

Jonathan Shilalis

Businesses Built

$228M+

Total Real Estate Volume

150+

Agents Recruited & Trained

15+

Years in Real Estate

Core Competencies

Where I Add Value

Acquisitions, underwriting, asset management, and due diligence across multifamily and commercial real estate.

Investment Strategy

Value-add and BRRRR (buy, rehab, rent, refinance, repeat)
Forced appreciation
Portfolio repositioning
1031 exchanges

Multifamily

Cap rate analysis and underwriting
Leasing
Sales and dispositions
Section 8 and affordable housing

Commercial

Leasing and sales
Industrial
Retail
Office
Mixed-use

Transactions & Due Diligence

Letters of intent (LOI)
Phase I environmental site assessments (21E reports in Massachusetts)
Deal sourcing
Commercial marketing

Tools

CoStar
LoopNet
Crexi

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

AI-First Operator

I implement AI into real businesses — not theory, not demos. Actual revenue-generating AI workflows for real companies.

Hands-On Developer

Developed ground-up multifamily projects and led value-add renovations — managing contractors, permitting, zoning, and CapEx budgets from site acquisition through lease-up.

Licensed Professional

Licensed Real Estate Broker in Florida, Massachusetts, and Maine. Trusted with the largest transactions in people's lives.

Results-Driven

$228M+ in total real estate volume. 4.9★ across 1,000+ reviews. Granted U.S. design patent and trademark. Websites built. Every venture has measurable outcomes — I don't dabble, I deliver.

Investor-Operator

Short-term rental (STR) operations with full P&L ownership — revenue management, dynamic pricing, occupancy, and RevPAR (revenue per available room). Acquisitions underwriting on cap rate and NOI (net operating income), due diligence, asset management, and workflow automation.

Philosophy

What Drives Me

At my core, I genuinely enjoy helping people succeed. This isn't just a professional philosophy — it's what drives every venture I pursue. I've donated significant time helping businesses leverage AI and technology to transform their operations, often with no expectation of return.

When I was at my previous brokerage, colleagues I mentored encouraged me to open my own office because of the impact I had on their careers. That's how Shilalis Real Estate was born — not from a business plan, but from relationships built on genuinely wanting to see others succeed.

This pattern has repeated throughout my career: helping people has always organically led me to my next business venture. It's a philosophy that creates lasting partnerships and sustainable growth.

Helping people succeed isn't a strategy — it's who I am.

How I Lead

Leadership Approach

Strategic Executor

Balances speed-to-market with quality control

Analytical Decision-Maker

Thorough on major initiatives, decisive on tactical matters

Performance-Driven

High standards, measurable outcomes, ROI-focused

Systems Builder

Creates scalable frameworks and processes

Core Competencies

M&A Negotiations

Team Building

P&L Management

Strategic Growth

Business Development

Operations Management

Portfolio

Experience & Projects

Real estate is the foundation. Every venture since has been built on the same discipline — find the opportunity, build it right, and run it well.

012010 – Present

Shilalis Real Estate

$228M+ in total real estate volume

Founded the firm in Watertown, MA in 2010 and grew it from 3 agents to 20+, expanding from rentals into full-service residential, multifamily, commercial, and property management — $228M+ in sales and lease volume, including 1031 exchange transactions. Represented buyers and sellers in commercial sales and leasing across industrial, retail, office, multifamily, and mixed-use property, from LOI through due diligence and closing, and marketed commercial listings on CoStar, LoopNet, and Crexi using comps and cap rate analysis to support pricing. Recruited and trained 150+ agents, then sold the Massachusetts brokerage in 2025 (now PH Realty Group). Licensed broker in Florida, Massachusetts, and Maine, and actively practicing in South Florida.

$228M+ total volume
150+ agents hired & trained
Sold MA brokerage in 2025

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022020 – Present

Real Estate Investor

Multifamily, fix-and-flip & short-term rental portfolio — sourced, built, and managed

My own real estate investment portfolio spanning ground-up multifamily development, fix-and-flip projects, and short-term rentals across Maine, Massachusetts, and Florida — Airbnb Superhost with Guest Favorite listings, 90% average occupancy, and a 4.9-star average across 1,000+ guest reviews. I source off-market deals, underwrite them (pro forma, cap rate, NOI, cash-on-cash), secure acquisition and construction financing, and use 1031 exchanges to defer gains and recycle equity, delivering 28% average cash-on-cash returns. I acquire and reposition value-add properties using the BRRRR method, forcing appreciation through renovation and better management. AI guest-messaging and dynamic-pricing workflows eliminated 20+ hours a week of manual work, so the portfolio runs on about 5 owner hours a week.

Ground-up multifamily development
Fix-and-flip & short-term rentals
Superhost · Guest Favorite · 4.9★ across 1,000+ reviews

03May 2026 – Present

DISCpute Resolve

The AI mediator that actually takes a side

Founder / Product Lead. Conceived, designed, and shipped an AI mediation app solo in about 5 months using AI-assisted development. Live on the App Store and Google Play with 1,500+ installs, with LLM and voice features and Stripe / in-app subscription billing.

Founder / Product Lead
Live on the App Store & Google Play
1,500+ installs

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04Jan 2026 – Present

Sun Biz Broker

Business brokerage in South Florida

Brings 15 years of real estate deal-making to business brokerage — helping owners and buyers value, sell, acquire, and transition businesses with the same disciplined approach behind $228M+ in real estate volume.

Business buy/sell facilitation
Valuations & market analysis
Entrepreneur-focused approach

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052024 – Present

10x AI Consulting

AI implementation for operators and executives

Consulting practice that helps businesses put AI to work — from prompt engineering and workflow design to automated operations — with a focus on measurable results rather than experiments.

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062025

Nessa Bottles

From concept to product — granted U.S. design patent and trademark

Invented a product from the ground up. Secured a granted U.S. design patent (D1,140,040) and trademark, negotiated directly with overseas factories, and built the entire e-commerce operation.

Granted U.S. design patent & trademark
Factory negotiations completed
Full e-commerce buildout

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Technology

AI Expertise

AI and automation applied to real operations — guest messaging, pricing, workflows, and software that actually ships.

AI Journey

2022

Started Building with GPT

Began using GPT and AI tools in day-to-day operations and saw the business potential early.

2023–24

AI Consulting

Started helping businesses implement AI workflows, then launched 10x AI Consulting in 2024 to build automations and websites for small-business clients.

2025

Full AI Integration

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

Technical Skills

LLM Workflow Design

AI Agent Deployment

Prompt Engineering

Business Process Automation

AI-Assisted App Development

E-Commerce Platforms

iOS & Android Apps

Additional Expertise

App development (App Store & Google Play)
Market research & product design
Website development with backends
Factory negotiations & supply chain

A personal message about my AI journey

What People Say

References & Testimonials

From LinkedIn recommendations to Zillow client reviews — here's what colleagues and clients have to say.

“Jon brings an unmatched work ethic to every project, diving into every detail and exploring every possible angle to ensure the best possible outcome for our clients. Jon’s ability to combine relentless effort with a sharp focus on client satisfaction makes him an invaluable asset to any team.”

Ethan Piani-Hohmann

Founder & Broker, PH Realty Group

“I had the privilege of working with Jon for nearly 13 years, and I can confidently say that he has been instrumental in shaping my career in real estate. His mentorship has helped me grow professionally, and his leadership has always been an inspiration.”

James Kousoulos

Broker/Owner, Capitol Square Realty

“I had the pleasure of working with Jon in a managerial capacity, and I can confidently say he is one of the most driven and knowledgeable real estate brokers I’ve encountered. His professionalism, integrity, and ability to navigate complex transactions set him apart in the industry.”

Shant Cimenian

Founder & CEO, Oakwood Financial Partners

“[Jon] helped my family find and close on an investment property in the Boston area. He was very knowledgeable and helpful throughout the process. I would highly recommend!”

Ariana

Investment Property Buyer

Zillow

“Jon was terrific. I'm a part-time landlord, and he gave me excellent pointers. He found qualified tenants extremely quickly, far faster than any other rental agents I have worked with in the past.”

Dan

Landlord

Zillow

“Great to work with! We've moved around the Boston area a few times and this apartment search / lease signing with Shilalis Realty was the easiest process. Jon was very responsive and knowledgable.”

Kaitlyn B.

Tenant

Zillow

View All LinkedIn Recommendations

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

Jon@shilalis.com

Phone

(508) 801-9530

Location

Boca Raton, FL

linkedin.com/in/jonshilalis

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

Six businesses built — from acquisitions, underwriting, and asset management to STR revenue management and AI workflow automation.

Send a Message

The fastest way to reach Jon is by email or by booking a time on his calendar.

Email Jon Schedule Appointment

Jon@shilalis.com · 508-801-9530