How Investors Evaluate Founders: The "Jockey" vs. The "Horse"

How Investors Evaluate Founders: The "Jockey" vs. The "Horse"

In the VC world, we often say we bet on the jockey, not the horse. At the Seed and Series A stages—especially in competitive markets like London, New York, and San Francisco—the business model will likely pivot, the market will shift, and the product will be rebuilt. The only constant is you.

The brutal truth? We are quietly evaluating your "Trajectory" rather than your "Pedigree." I’ve seen founders with three Ivy League degrees fail our evaluation because they lacked "Coachability," and I’ve seen dropouts from Toronto raise $10M because they possessed "Obsessive Domain Expertise." Behind closed doors, we aren't just looking at your CV; we are performing a psychological audit of your ability to withstand the "Trough of Sorrow" and emerge as a category leader.

This sub pillar is part of our main Pillar 4 — Investor Psychology

The VC Lens: The Three Dimensions of Founder Fit

When I’m sitting in an IC (Investment Committee) meeting, we evaluate founders across three non-negotiable dimensions. If you fail one, the deal is dead, regardless of your MRR.

1. Founder-Market Fit (The "Earned Secret"): Why you? Why now? Do you have a deep, almost unfair understanding of the industry's friction, or did you just pick a "hot" sector from a TechCrunch headline?

2. Velocity of Learning: How fast can you absorb new data and iterate? If I give you a "red flag" on Tuesday and you come back on Friday with a pivot, a new data set, or a customer quote addressing it, you’ve moved into the top 1% of founders.

3. The "Magnet" Factor: Can you hire people smarter than you? Can you convince a senior engineer to leave Google or a top VP of Sales to leave a unicorn to join your "dream"? If you can't recruit, you can't scale.

In the US (SF/NY), we lean into "Aggressive Ambition." We want the founder who thinks they can build a $100B company. In the UK and Canada, we look for "Pragmatic Resilience." We want to know you won't blow through $5M in six months on a "vision" that hasn't been unit-economic tested.

The "Trench" Report: The $20M "Ego" Pass

Last year, a New York-based founder pitched us a brilliant AI infrastructure play. He was a "Star" on paper—Ex-Meta, PhD, brilliant technical mind. But during the Q&A, every time a Partner challenged his assumptions on GTM (Go-to-Market) strategy, he became defensive. He "lectured" the room rather than engaging in a dialogue.

The consequence? We passed. Not because the tech wasn't great, but because he lacked "Coachability." As a VC, I am entering a 7-to-10-year marriage with you. If I can't have a difficult conversation with you during the honeymoon phase (the pitch), I certainly can't help you when the business hits a wall in year three. Arrogance is a signal of a low "Learning Velocity."

The Tactical Framework: The "Founder Signal" Audit

To win the "Jockey" evaluation, your pitch and presence must project three specific signals:

1. The Signal of "High Agency"

Show, don't tell, that you can bend reality to your will.

• The Fix: Mention a specific hurdle—regulatory, technical, or financial—that should have killed the company, and explain exactly how you navigated it.

• The VC Thought: "This founder is a heat-seeking missile for solutions."

2. The Signal of "Domain Authority"

You must know your numbers better than the Associate who spent all night researching your sector.

• The Fix: Don't just know your LTV/CAC; know the Standard Deviation of your customer cohorts and the Marginal Cost of your next 1,000 users.

• The VC Thought: "They aren't just a visionary; they are an operator."

3. The Signal of "Storytelling Mastery"

VCs need to know you can sell—to investors, to employees, and to customers.

• The Fix: Frame your business as an Inevitable Market Shift, not just a product. Use the "Big Change" narrative (Sub-pillar 6) to show you are the conductor of a global trend.

Semantic Depth: Screening for "Resilience" and "Scale"

Beyond the "vibe," we are looking for technical indicators of your leadership potential.

The "Hiring Bar" Test

On your Team slide, don't just list names. List where they came from. If your first three hires are all "Junior" or "Generalists," it signals you are afraid to manage people who know more than you. If you have a "Principal Engineer" from a successful scale-up, it signals that you have the "Magnet Factor."

The "Capital Allocation" Mindset

We screen for how you think about money. If your "Ask" slide is purely for "Hires" without specific Value-Inflection Points, you look like a "Spender."

• Signal: "We are raising $4M to reach $10M ARR, which we will achieve by scaling our proven outbound channel from 2 to 10 AEs."

• The VC Thought: "This founder treats my capital like an investment, not a bank account."

Cognitive Diversity in the Founding Team

In London and Toronto, we look for "Balanced" teams. If you have three "Product" founders and zero "Sales" or "Operations" DNA, we see Execution Risk. We want to see a "Hacker," a "Hustler," and a "Designer" (or the equivalent) to ensure the business is a three-dimensional machine.

The Contrarian Take: Your "Pedigree" Might Be a Liability

Here is a secret: Some VCs are wary of the "Perfect" founder. If you’ve spent your whole life at McKinsey, Goldman Sachs, and Harvard, you’ve never really failed. You’ve always been in an environment where the "brand" did the work for you.

I often prefer the founder with a "Chip on their Shoulder." The one who was told "No" by the elite institutions. They are the ones who will work 100-hour weeks when the bank account is low and the "Big Tech" firms are poaching their staff. Resilience is built in the shadows, not the spotlight.

Key Takeaways for Founders

• Optimize for Coachability: Engage with questions as a collaborator, not a defendant.

• Prove High Agency: Use your "Origin Story" to show how you overcame impossible odds, not just how you got the idea.

• Sell the Mission: VCs bet on leaders who can recruit a "Mercenary" team and turn them into "Missionaries."

• Know Your Metrics: Domain authority is the only antidote to "Founder Risk."

Expert FAQ: The "Founder Audit"

Q: Does my age matter?

A: In SF, there is a bias toward the "Young Disruptor." In London and Canada, there is often a bias toward the "Experienced Executive." To counter either, focus on Velocity. If you’re young, show me you can learn in a month what takes others a year. If you’re experienced, show me you haven't lost your "Hunger."

Q: Should I mention my co-founder conflicts?

A: Never in the first pitch. But if you've lost a co-founder, have a clean, logical explanation for why it was the right decision for the company’s Long-term Health.

Q: What is the biggest "Red Flag" during a founder evaluation?

A: Inconsistency. If your "Vision" on Slide 1 doesn't match the "Financials" on Slide 10, or if you tell me one thing and the Associate finds another in the data room, the trust is gone. In VC, trust is the only currency that doesn't deflate.

Q: How do I handle a question I don't know the answer to?

A: Don't guess. Say: "That is a great question. We have the raw data in the data room, but my intuition says [X]. Let me get you the exact cohort breakdown by the end of the day." This signals Authority and Speed.