INSIGHTS & UPDATES

Highland Insights

Perspectives on private office coordination, business strategy, and investment opportunities in Central Florida

FEATURED POST

Two business owners shaking hands over a completed deal
Investments July 15, 2026 5 min read

The SBA Just Doubled the Ceiling. Here's What That Changes for Central Florida Business Owners.

On July 4, the SBA doubled its combined 7(a) and 504 cap to $10M, the biggest cap increase in fifteen years. Here's what that shift means for owners weighing an acquisition, a real estate move, or a succession decision in this market.

Read Full Article →

All Articles

Two business owners shaking hands over a completed deal
Investments 5 min

The SBA Just Doubled the Ceiling. Here's What That Changes for Central Florida Business Owners.

The SBA quietly doubled its combined 7(a) and 504 cap to $10M on July 4. For Central Florida owners weighing a growth acquisition, a real estate move, or a succession decision, the addressable deal size just expanded meaningfully.

July 15, 2026 Read More →
Downtown Orlando skyline reflected across Lake Eola at sunrise
Investments 5 min

Capital Is Getting Organized in Central Florida. Are You?

Penske, Modern Wealth, and DFCU are organizing capital in our market. Two readers should be paying attention: business owners facing an acquisition conversation, and high earners with no system around the household balance sheet.

June 17, 2026 Read More →
Evan Ross featured in Orlando Voyager
Press & Media 3 min

Featured in Orlando Voyager: Highland's Story, In My Own Words

Orlando Voyager published a feature on Highland Private Office. The full interview covers Celltronix, COVID, why I built Highland the way I did, and how I think about risk.

May 5, 2026 Read More →
Organized desk with documents and planner for an operational audit
Private Office Coordination 9 min

The 7-Day Operational Audit Every High-Net-Worth Family Should Run

A practical week-long audit that surfaces the bill-pay leaks, vendor sprawl, and document gaps most HNW families don't realize they have. Block 30 to 60 minutes a day for a week.

Apr 28, 2026 Read More →
Private Office Coordination 8 min

Why High-Net-Worth Individuals Need a Private Office Coordinator

When your financial life involves multiple advisors, business interests, and complex decisions, coordination becomes the missing piece. Here's why alignment matters.

Mar 19, 2026 Read More →
Steve Jobs iPhone launch 2007, the smartphone parallel for AI agents
Business Strategy 6 min

Your AI Agent Is Coming. Probably Sooner Than You Think.

AI agents aren't science fiction, they're the next platform shift. The question isn't if you'll have one. It's whether you'll be ready when it arrives.

Mar 2, 2026 Read More →
Wheels Watches Whiskey Wine event at Land Rover
Client Experience 6 min

Wheels, Watches, Whiskey & Wine: Where Business Meets Passion

An evening among exotic cars, rare timepieces, and new connections at Land Rover of South Orlando, what it means to work with clients who share a passion for excellence.

Feb 25, 2026 Read More →
AI and business automation
Business Strategy 6 min

AI Implementation: Essential for Business Survival

Real case study shows 97% cost reduction. What Central Florida business owners need to know about AI implementation.

Feb 10, 2026 Read More →
Modern business technology
Business Strategy 4 min

Why Local Businesses Need Better Technology Systems

Transform your operations with the right technology. Practical solutions for Central Florida small businesses.

Feb 5, 2026 Read More →
Business investment partnership
Investments 5 min

What Makes a Good Business Investment?

Our criteria for evaluating business investments in the Central Florida market. Leadership, proven models, and growth potential.

Feb 1, 2026 Read More →
Supreme Court and economic policy
Policy Analysis 8 min

Supreme Court Strikes Down Trump-Era Tariffs

What family offices and small businesses need to know about the Supreme Court ruling and potential tariff refunds.

Feb 15, 2026 Read More →
AI assistant Crabby
AI & Automation 7 min

Building an AI Assistant for Business Operations

How we built Crabby, an AI assistant that handles scheduling, email, and administrative work autonomously.

Feb 11, 2026 Read More →

Important Disclosure

Highland Private Office is a business consulting firm, not a registered investment advisor, broker-dealer, or financial planner. We do not provide investment advice, manage client portfolios, offer securities, or act as a fiduciary for investment purposes. Our services include business consulting, private office coordination, and facilitating relationships with licensed professionals including registered investment advisors, CPAs, and attorneys. All investment and financial planning decisions should be made in consultation with appropriately licensed professionals.