Shookster.
Joe Shook · Founder · South Florida

I build companies that answer to the records.

Thirty years in enterprise technology, including CIO of Zimmerman Advertising and EVP of IT at Omnicom. Now building lean, AI-run businesses where every claim traces back to a document. My main focus is HOAShark.

As featured onBeyond Success TVDocuseries on the Inside Success TV app · Episode early 2027

Every line. Every figure. Every exhibit. Traced to the source.

That's the standard at every company I build, from a condo association's ledger to a client's campaign report.

30yrsLeading enterprise technology
12yrsRunning IT inside a national ad agency
3Companies, each its own LLC
Company register

What I'm building

Entry 01

HOAShark

Litigation-grade forensic review of Florida HOA and condo association records. It turns ledgers, bank statements and board records into an organized case file for attorneys and forensic CPAs.

HOAShark LLC · hoashark.com
Main focus · Live
Entry 02

CondoCheckpoint

A report on a condo building's records for buyers, before they sign. Think of it as a history report for the building.

CondoCheckpoint LLC · condocheckpoint.com
Coming soon
Entry 03

Shookster.ai

AI marketing systems for agencies and growing companies: outbound appointment setting, creative and ad production at volume, and client reporting. Agency experience, rebuilt around AI.

Shookster.ai LLC · marketing services below
Active

Each company is its own LLC, owned by Joe Shook and run separately.

Flagship · Entry 01

HOAShark: follow the money, every line

Forged in fire.

Watch Forged in FireThe 50-second film about how HOAShark was made →

As a Florida condo owner, Joe saw how slow and expensive it is to answer a simple question about an association: where did the money go? A forensic accountant was out of reach, so he did the work himself, then built the tools to make that work repeatable.

HOAShark does the first forensic pass on an association's books, the part that usually waits until an expert is hired, and ties every finding to the document it came from. The expert's hours go to judgment instead of data entry.

  • Every figure traces to its sourceEach finding points to an exhibit and a page.
  • Facts firstFindings state what the records show. Opinions stay labeled as opinions.
  • Nothing is lostEvery file is kept unchanged with its SHA-256 fingerprint.
  • Your matter stays yoursEach matter is sealed off from every other.
  • Early access is openFlorida attorneys and forensic CPAs get a direct line to the founder.
Entry 03 · Shookster.ai

The systems behind a national ad agency, now run on AI

From 2012 to 2024 Joe ran technology inside one of the country's largest advertising agencies: first as EVP of IT and Chief Information Officer at Zimmerman Advertising, then as EVP of IT for Omnicom's Advertising Collective and Commerce Groups. That meant the systems behind media, digital, social, creative and video production for national brands.

Shookster.ai takes what that work requires, steady pipeline, creative at volume and reporting a client can trust, and builds it as AI systems a lean team can run.

The same rule applies as at HOAShark: the numbers in a report have to trace back to something real.

  • Outbound appointment settingAI-run prospecting that books qualified meetings without a full SDR team.
  • Creative and ad productionOn-brand creative produced and tested at volume, every month.
  • Client retention and reportingAutomated reporting and early warnings on accounts that are slipping.
About

Joe Shook

Joe has spent 30 years leading enterprise technology, most recently as CIO of Zimmerman Advertising and EVP of IT at Omnicom, where a system was only as good as the records behind it. Along the way he worked through many high-stakes corporate legal matters, where the outcome often came down to what the records could prove.

Today he builds companies the same way: AI does the heavy lifting, the records settle the argument, and Joe makes the calls.

2022–2024
EVP of IT, Advertising Collective & Commerce Groups, Omnicom
2012–2022
EVP of IT and Chief Information Officer, Zimmerman Advertising
Before that
CTO of a Florida college group, CIO of a national restoration franchise, founder of a technology consultancy, and IT leadership at a trading firm
Based in
South Florida
Companies
HOAShark, CondoCheckpoint, Shookster.ai
As featured on
Beyond Success TV, a docuseries on the Inside Success TV app. Episode early 2027.
Staff
Luna, a beagle. Chief Sniffing Officer.
Contact

Talk to Joe

Press, partnerships, Shookster.ai marketing work, or a matter that needs a careful look at the records. For HOAShark support, use hoashark.com.

joe@shookster.com