Why VCs Should Care About the ‘Cherrypick’ Mindset: How Technical Precision Impacts Startup Valuation

As a VC, I look for signals of technical excellence and efficiency in a startup’s DNA. But here’s what most miss: the *mindset* behind the code matters more than the stack itself. After evaluating hundreds of technical teams, I’ve found one pattern that consistently predicts higher valuations: the “cherrypick” mentality.

The Art of the Cherrypick: What Coin Collecting Teaches Us About Technical Due Diligence

I remember the first time I saw a 1937 Washington Quarter DDO (FS-101) “cherrypick” – a rare double die obverse coin found in raw, ungraded condition by a collector who noticed subtle doubling others missed. As a collector myself, I wasn’t just impressed by the find. I saw a mirror for early-stage investing: the ability to perceive hidden value where others see uniformity is the hallmark of elite technical judgment.

In numismatics, a “cherrypick” means spotting a high-value variant in a sea of common items. The same applies to tech investing. The best startups don’t always have the flashiest pitch. They’re the ones that, at first glance, look ordinary but contain extraordinary technical depth. The tell? How the team approaches technical assessment, iteration, and stack optimization.

Why the Cherrypick Mentality Matters in Seed & Series A Investing

At seed stage, we evaluate vision and team. By Series A, we need proof. And that’s where the cherrypick mindset separates the winners. The founders who, like that coin collector, can “see the doubling” in their own stack – who obsess over inefficiencies, optimize relentlessly, and validate their architecture – are the ones who command premium valuations.

Consider two startups using identical stacks (React, Node.js, PostgreSQL). One stands out because they:

• Squeezed 70% faster database queries through smart indexing and caching
• Spotted bottlenecks in real-time with distributed tracing
• Cut deployment risk with custom CI/CD automation
• Built clear microservices boundaries with documented SLAs

They didn’t change their stack. They changed how they *used* it. That’s the cherrypick.

What VCs Look for in a Tech Stack: The Technical Due Diligence Checklist

During due diligence, I care less about *what* tools a team uses and more about *how* they think about them. Here’s my framework:

1. Evidence of Iterative Optimization (Not Just “It Works”)

Great teams don’t just ship. They measure, iterate, and optimize. When I meet a team, I ask for:

• Load testing results: What happens at 10x traffic?
• Error tracking & SLA compliance: Are they watching for 5xx errors, latency spikes?
• Tech debt tracking: Do they log and prioritize technical improvements?

Code Example: This startup used OpenTelemetry to track request latency:


const tracer = require('@opentelemetry/api').trace.getTracer('api-service');

app.get('/api/users/:id', (req, res) => {
const span = tracer.startSpan('fetch-user');
try {
const user = db.query('SELECT * FROM users WHERE id = ?', [req.params.id]);
span.setStatus({ code: SpanStatusCode.OK });
res.json(user);
} catch (err) {
span.setStatus({ code: SpanStatusCode.ERROR, message: err.message });
span.recordException(err);
res.status(500).json({ error: 'Internal server error' });
} finally {
span.end();
}
});


That’s not just observability. That’s a team that thinks like collectors.

2. Architecture That Scales (Without Over-Engineering)

Too many startups jump to microservices too early. The cherrypick teams know when to keep it simple and when to modularize. I look for:

• Domain-driven design: Services organized by business capability
• Async communication: Using queues like Kafka or RabbitMQ for critical workflows
• Smart database scaling: Read replicas or sharding where it matters

They avoid cloud-native bloat but embrace enough abstraction to scale.

3. Security & Compliance Built In

Security isn’t a checkbox. It’s a culture. Cherrypick signals:

• Automated dependency scanning (Snyk, npm audit)
• Input validation at every layer – no surprises
• Regular penetration testing and OWASP compliance

I met a founder who said, “We run a weekly security checklist. It’s boring, but it finds problems before they find us.” That’s the cherrypick mindset.

The “Second Pass Through the Room” Effect: Why Patience Pays

That coin collector found the 1937 DDO on their second pass. They didn’t rush. They compared, analyzed, trusted their eyes. The best VCs do the same. We don’t invest in the first pitch. We:

• Re-watch technical demos with a finer lens
• Ask for raw performance data, not just polished charts
• Talk to junior engineers – they see what leadership misses
• Stress-test the stack with real-world scenarios

Just like the collector finding a “struck-through fragment” in their own collection, I’ve spotted startups that revealed their edge only after digging. One fintech team had quietly built a fraud detection module that slashed false positives by 40% – buried in GitHub commits. They didn’t highlight it in their deck. That’s the hidden value that justifies a premium valuation.

Grading the Stack: How Technical Excellence Translates to Valuation

When a coin gets graded, it’s assigned a number (MS63+) reflecting condition, rarity, demand. The same applies to tech stacks. Here’s my “grading” framework:

The “cherrypick” stack isn’t about tools. It’s about how deeply they understand and improve them. A team using the same frameworks as their peers but achieving 10x faster CI/CD or 5x lower error rates? That’s like the 1937 DDO: rare, valuable, and worth documenting.

Actionable Takeaways for Founders & Investors

For Founders: Be the Cherrypicker

• Audit your stack quarterly: Find inefficiencies before investors do
• Document everything: Architecture diagrams, benchmarks, security policies
• Highlight your “doubling”: Call out technical optimizations in your deck
• Experiment “raw”: Not every feature needs polish – but your core architecture does

For Investors: Look for the Doubling

• Ask for raw data: Not “we use AWS” – but how they use it
• Demand traceability: Show me error rates, deployment frequency, cache hit ratios
• Spend time with engineers, not just the CTO
• Value the second look: The best insights come from looking again

Like that coin collector, I’ve learned: the most valuable things are often hiding in plain sight. For VCs, that means seeking startups that treat their stack like a treasure hunt – not a checklist. The 1937 DDO didn’t look special at first. But with a keen eye, it became a gem. The same applies to technical excellence in startups. Find the cherrypicks, and you’ll find the next unicorn.

The Cherrypick Principle in VC

The story of the 1937 Washington Quarter DDO isn’t just about a rare coin. It’s a metaphor for technical investing. The teams that “cherrypick” their stack, optimize relentlessly, and validate their architecture are the ones who:

• Stand out in crowded markets
• Command higher valuations at seed and Series A
• Build products that scale efficiently
• Attract investors who appreciate depth

As a VC, I don’t just look for startups that work. I look for those that know why they work. The cherrypick mindset is the difference between a “me-too” product and a technical marvel. In a world of undifferentiated tech, that’s the coin every investor should be hunting for.

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