What does an operator who becomes a VC look for? We asked Rachel ten Brink, Red Bike Capital.
With Andy Walsh
The Big Idea
Rachel ten Brink sat across from me and said something that landed differently than I expected.
She wasn’t talking about pattern-matching or deal flow or fund thesis. She was talking about pancakes. Specifically, the pancakes she made the morning of her second YC interview — the one they also said no to. She flew to San Francisco, did the pitch, came back to the Airbnb, and got the rejection. Three attempts before they got in. Scentbird is now in the top 2% of YC companies by revenue.
That gap between rejection and result — that’s where most of the real founder story lives. Not in the highlights reel. In the part where you keep going anyway.
But here’s what this conversation actually made me think about: the operator who becomes an investor doesn’t just bring capital. They bring pattern recognition that most VCs don’t have access to. Rachel spent two decades inside Fortune 500 companies — P&G, Estée Lauder, L’Oréal. She’s been the enterprise client. She knows how their procurement works, who makes the real decisions, why they require 24 months of runway before they’ll onboard a startup vendor. That’s not in any CRM. You can’t enrich your way to it with Clay.
The single most important takeaway: the operator mindset is a durable competitive advantage — whether you’re a founder or an investor. And most founders don’t build it deliberately.
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The Constraint + Filter Question
Here’s the specific friction point this episode speaks to.
Most early-stage founders think their primary job is to build a great product and tell a compelling story. Rachel’s position is more useful: your primary job is to generate traction that tells the story for you.
She’s direct about it: “Traction explains a heck of a lot more than the most beautiful deck.”
This matters most when you’re approaching enterprise clients. Not SMBs. Enterprise. The kind of client that takes three months just to onboard you. The kind that won’t work with a company that has less than 24 months of runway — not because they don’t like you, but because they’ve been burned by vendors disappearing mid-contract.
If you’re building toward enterprise, the question isn’t whether your product is ready. It’s whether you understand the world your client lives in well enough to survive their process.
Filter question: If your enterprise prospect had to explain your value to their procurement team tomorrow, what would they actually say?
If you don’t know the answer to that, you’re not ready to pitch them.
The Framework — In Full
Rachel describes herself as a pragmatist. I think that’s actually a framework — and it’s one worth breaking down.
Step one: Ground yourself in reality, not aspiration.
She gave a specific example: a founder she’d been advising who was trying to raise at a $20M valuation with no real business yet. Not pre-revenue — pre-business. The founder kept citing YC benchmarks as justification. Rachel’s advice: do the $15M, close the round, get back to building. Speed is one of the only real advantages an early-stage startup has. Burning 18 months on a fundraise neutralises it entirely.
The failure mode here is letting benchmarks from other companies override your actual situation. What YC companies raise at is irrelevant if you don’t have what YC companies had when they raised it.
Step two: Understand what optionality actually costs.
There’s a version of “protecting your equity” that becomes self-defeating. Rachel’s been explicit about this: she’s seen founders at pre-seed who’ve given up more than 50% of their economics before they’ve built anything. Those companies become uninvestable. You can’t run a clean cap table at Series A when the founder has already diluted themselves into a corner.
But she’s equally clear about the other failure mode — founders who hold so firm on valuation that they spend a year and a half fundraising while the business stagnates. Equity means nothing if you run out of runway.
The edge case that changes the calculus: sometimes waiting two weeks to lock in a signed pilot — even unpaid — transforms your fundraise. Walking in with CVS and United Healthcare as pilots, even at zero revenue, shifts the room. That’s not about ego. It’s about evidence.
Step three: Know what’s being said when you’re not in the room.
VCs talk. A lot. If you’ve been on the circuit for six months and you’re coming in defeated, frustrated, visibly worn down — that follows you. You don’t get a second first impression. Managing your state isn’t soft skill territory. It’s strategic.
The Case
In 2012, I signed Microsoft as a client in the first year of my business. I thought that was the win.
What followed was three months of procurement process I hadn’t anticipated. Compliance reviews. IT security questionnaires. Legal redlines. The infrastructure of a publicly listed company that had to protect itself at every step. To be clear: they were professional, fair, and ultimately great to work with. But I walked into that deal thinking the signature was the finish line. It wasn’t even the start line.
What I should have known: enterprise clients are evaluating whether you can survive their process, not just whether your product solves their problem. Those are two different things. A lot of startups close the deal and then collapse under the weight of operationalizing it.
The real lesson isn’t that enterprise sales is hard. It’s that you need to understand the client’s world before you pitch into it. What does their procurement cycle look like? Who has internal sign-off authority? What are their vendor requirements? You can’t discover these things in the sales cycle. You need to know them before you book the first meeting.
Rachel’s advantage — the reason Red Bike can help founders land enterprise clients with unusual effectiveness — is that she was that client. She sat on the other side of the table. That’s not replicable by reading a playbook.
The Mindset Section
There’s a moment in the episode where Rachel talks about founders who walk into investor calls already defeated.
She’s seen it on camera. The Zoom turns on, and the founder is already projecting six months of accumulated rejection before a word is spoken. And she’s sympathetic — she’s been there. She made pancakes the morning of a pitch and still got a no. But her point is pointed: that investor has never met you before. It’s their first conversation. Whatever happened to you in the previous 25 meetings is yours to manage — not theirs to absorb.
This is the thing that separates founders who close rounds from founders who technically deserve to. Not the deck. Not the product. The state they’re in when they show up.
Rachel calls it managing your emotional state. I’d call it one of the highest-leverage skills in the founder toolkit — and the one nobody talks about because it sounds like it belongs in a self-help book rather than a strategy session.
It doesn’t. It belongs here.
The operating rule: A founder who manages their state well will outlast a technically better founder who doesn’t.
The Worksheet
Three questions to run before your next enterprise pitch:
Can I describe their procurement reality, not just their pain point? What does the sales cycle actually look like from their side? What do they need from a vendor before they’ll say yes — financially, operationally, legally?
What does my traction say without me explaining it? If an investor or client saw only your numbers — no narrative, no context — what conclusion would they reach? If the answer is “I’d need to explain it,” that’s the gap to close before you start the conversation.
What state am I in right now, and is it the state I want to show up in? Not in a wellness sense. In a strategic one. If you’re carrying six months of rejection into the room, it shows. What would you do differently in the next 48 hours before a high-stakes conversation?
“Your most valuable asset at this point is your equity. If you’re going to give it up, make sure you’re getting something that actually moves the business forward.” Rachel ten Brink
Research + Context
The idea that early-stage startups need to think like enterprise vendors — not just product builders — is backed by how procurement actually functions at scale. Enterprise procurement teams routinely require financial stability proof before onboarding new vendors, which is why runway visibility matters not just for investors but for customers. The expectation gap between how founders think enterprise sales works and how it actually unfolds inside large organisations is one of the most consistent sources of lost deals at the post-pilot stage.
Rachel’s point about AI compressing product advantages is also well-supported: when a competitor can replicate your core feature set in a weekend, the moat shifts to distribution, proprietary data, and operational context. Product differentiation alone no longer buys the time it once did.
Related Episodes
Ep#19 — Mark McNally - The AI Playbook: How Founders Must Adapt — pairs well here because it goes deep on product differentiation in an AI-first world, which is the exact context Rachel’s framework for distribution moats lives inside.
Ep#47 — Mihir Deo, Invoice Butler — the enterprise sales angle is more operational here, but the through-line on AI + humans in finance directly connects to Rachel’s thinking on team structure and where the 100x engineer fits.
Ep#44 — Ashley Bell Use Banks, Not VCs: Non-Dilutive Capital for Founders — a natural counterweight to this episode. Rachel’s pragmatic take on equity preservation is sharper when you have this conversation alongside it.
The Operating Rule
A founder who manages their state well will outlast a technically better founder who doesn’t.
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