A CTO’s Strategic Takeaways from the 2025 Rosemont/Chicago Great American Coin Show: Lessons in Leadership, Authentication, and Digital Transformation

As CTO, I see my role differently now. Technology isn’t just about code or infrastructure—it’s about building systems people actually trust. My weekend at the 2025 Rosemont/Chicago Great American Coin Show reminded me why that matters. Here’s what I learned that’s already changing how we work.

The Unseen Parallels Between Numismatic Authentication and Digital Asset Verification

Let me paint you a picture: A room full of people examining tiny details on century-old coins under powerful magnifiers. The stakes? Sometimes millions of dollars. But what really grabbed me wasn’t the 1914-D Lincoln cent or the 1885-O Morgan dollar.

It was the process. The same challenges we face with digital assets—fakes, forgeries, trust gaps—were playing out right there on the bourse floor.

Take the guy who brought in a “1943 copper cent,” still wearing his PCGS slab. He insisted it was real, despite the certification being fake. Sound familiar? We see this daily with digital asset verification. The patterns are eerily similar:

• Automated checks catch the easy stuff, but won’t stop sophisticated fakes
• Experts can spot nuances algorithms miss—but they’re expensive and rare
• Trust gets broken in the middle, whether it’s a coin grading service or an exchange
• Community consensus matters more than any single authority

Strategic Implications for Our Authentication Stack

This experience confirmed our authentication approach—but also forced us to refine it. We now structure our system like PCGS does their workflow, but for digital assets:

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1. Automated screening (like checking coins for magnetism)
2. Expert review with clear, documented criteria
3. Third-party validation (think CAC’s secondary review)
4. Blockchain audit trail so everyone can verify the process

Here’s the technical implementation we built, inspired by numismatic best practices:


{
"verification_layers": [
{
"layer": "automated_screening",
"checks": ["metadata_analysis", "pattern_recognition", "historical_frequency"],
"threshold": 0.85
},
{
"layer": "expert_review",
"reviewers": ["senior_curator", "technical_specialist"],
"documentation": "required"
},
{
"layer": "consensus_validation",
"validators": ["external_expert", "community_vote"],
"quorum": 2
},
{
"layer": "blockchain_audit",
"ledger": "ethereum",
"immutable_log": true
}
],
"timeouts": {
"automated_screening": "5m",
"expert_review": "48h",
"consensus_validation": "72h"
}
}


Leadership Lessons from the Bourse Floor: Managing Distributed Expert Networks

The coin show floor wasn’t just a marketplace. It was a working model of decentralized trust—something we’ve been trying to figure out for years.

Picture this network:

• PCGS and NGC as the quality control centers
• Dealers like Rick Snow as the domain experts (you’d wait in line to hear their opinion)
• Artists like Robert Julian preserving authenticity through original work
• Collectors bringing real-world data from years of hands-on experience

Applying This to Our Engineering Team Structure

This changed how we organize our teams. Instead of one monolithic engineering group, we created specialized “authentication pods”:

Results? 37% fewer authentication errors. 22% faster processing. Not bad for lessons from a coin show.

Budget Allocation: The “Three Bottle” Approach to Resource Management

Here’s a moment that stuck with me: Three wine bottles making the rounds at dinner—Rombauer Zinfandel, Cline Zinfandel, Oregon Bellingar Pinot. No hierarchy, no one refusing to share. Just a network sustaining itself.

That became our budget model:

The Three Bottle Budget Model

1. Base Allocation (Rombauer): The essentials—servers, salaries, the stuff that just works
2. Flexible Pool (Cline): Shared resources for surprises (like when Rick Snow’s team needed coverage during a health scare)
3. Innovation Reserve (Pinot): Riskier bets, like that shipwreck display that drew crowds despite uncertain value

Our allocation looks like this:

• 65% Base (infrastructure, team)
• 20% Flexible (crisis response, cross-team projects)
• 15% Innovation (emerging tech experiments)

When we found a critical authentication vulnerability two days before launch, the Flexible Pool let us redirect three senior engineers without blowing up other timelines. Just like dealers covering tables at the show, we had a system for mutual support.

Hiring Strategy: The “Dinner Table” Filter

Let’s talk about the dinner scenes at Gibson’s and Carlucci’s. These weren’t just meals. They were stress tests.

Watch how someone handles themselves when:

• A 20-person private room full of industry leaders is watching
• Conversations jump between technical details and personal stories
• Someone brings up a controversial topic just to see reactions

Implementing the “Dinner Table” Interview Process

We scrapped the whiteboard. Now we do:

• Problem-solving over food (much more revealing than standing at a board)
• Guided discussions that show how they think and communicate
• Natural interactions with potential teammates
• Real scenario pressure tests (like, “How would you handle a client insisting they have a ‘1943 copper’ that’s clearly fake?”)

Since we started this? Early attrition dropped from 25% to 11%. Team cohesion scores jumped 40%. Turns out, sharing a meal reveals a lot about someone.

Tech Roadmap: The “Show Schedule” Release Cadence

Notice the coin show’s rhythm? Wednesday setup, Thursday-Friday peak, Saturday wind-down. It’s not by accident.

We now run our major launches like this:

“Show Schedule” Release Framework

1. Wednesday – Dealer Day (Internal): Final checks, security review, team prep (like dealers doing bag checks before opening)
2. Thursday – Public Opening (Phase 1): Controlled release to trusted users (that long line of early collectors)
3. Friday – Full Floor (Phase 2): General release with extra support (peak traffic)
4. Saturday – Wind Down (Post-Mortem): Review while monitoring (as the show slowly empties)

This cut our critical post-release bugs by more than half. Team stress levels? Way down. Turns out, pacing matters.

Long-Term Strategic Planning: The “Next Year’s Dates Announced” Principle

Here’s a detail most people miss: The 2026 dates (September 30 – October 3) were announced right in the middle of the 2025 show. No waiting for the next newsletter. Right then. Why?

Because stability matters. For our teams, that means:

• 3-year technology plans released at our annual Tech Summit
• Clear pictures of where we need talent in 2-3 years, not just next quarter
• Budget frameworks set before we start arguing about specifics
• Career paths tied to long-term projects

Our roadmap now includes:

• Platform milestones mapped out years ahead
• Team growth plans that match technical needs
• Themes that guide innovation: AI authentication (2024), decentralized validation (2025), quantum security (2026)

Actionable Takeaways for Tech Leadership

• Layer your authentication: Automated checks + expert review + consensus + audit trail
• Structure teams as specialized pods: Deep focus beats generic departments
• Try the “Three Bottle” budget model: Stable base, shared flexibility, room for risk
• Use social interactions to hire: A dinner conversation reveals more than a technical test
• Release like a show: Prepare, phase, peak, review—no big bangs
• Plan publicly: Give your team the security of long-term vision

Conclusion: The Numismatic Model for Modern Tech Leadership

The 2025 Rosemont/Chicago Great American Coin Show wasn’t just about old coins. It was a working model of trust, expertise, and community—exactly what we struggle to build in digital spaces.

What surprised me most? The human side matters as much as the technical. A PCGS slab only means something because of the experts behind it. Our digital infrastructure needs the same.

Whether you’re verifying a rare coin or a blockchain transaction, the fundamentals are the same:

• Trust is built through transparency
• Expertise can’t be centralized
• Community validation beats any single authority
• Process matters as much as results

The coin show taught me that our most important technology isn’t what’s in our servers. It’s the network of people, expertise, and shared standards that keep the whole system honest.

For CTOs building in the digital asset space—authentication, security, distributed trust—I can’t think of a better classroom than the bourse floor. I’m already prepping for next year’s show. Not for the coins. For the lessons.

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