Sam Corcos: Why Founders Should Take as Many VC Meetings as Possible | E1093

Sam Corcos: Why Founders Should Take as Many VC Meetings as Possible | E1093

The Twenty Minute VCDec 11, 20231h 19m

Harry Stebbings (host), Sam Corcos (guest)

Fundraising strategy and taking many VC meetingsExtracting real value from angels, VCs, and platform teamsRadical transparency, performance management, and the keeper testHiring philosophy, product vs. engineering balance, and A-players at scaleRisk tolerance, luck, and the psychology of failure for foundersTime management, calendar auditing, and high-performance habitsIntentionality in relationships, parenting, and co-founder dynamics

In this episode of The Twenty Minute VC, featuring Harry Stebbings and Sam Corcos, Sam Corcos: Why Founders Should Take as Many VC Meetings as Possible | E1093 explores sam Corcos: Fundraising, Transparency, And Intentional Living For Founders Sam Corcos, CEO and co-founder of Levels, discusses how extreme transparency, intentional time management, and a wide-net fundraising strategy shape how he builds companies and relationships.

Sam Corcos: Fundraising, Transparency, And Intentional Living For Founders

Sam Corcos, CEO and co-founder of Levels, discusses how extreme transparency, intentional time management, and a wide-net fundraising strategy shape how he builds companies and relationships.

He advocates taking as many investor meetings as possible, treating fundraising as building long-term lines, not one-off dots, and being ruthlessly specific about what help you need from investors.

Internally, he shares how Levels uses radical transparency on performance and one‑on‑ones, the Netflix-style keeper test, and a strong bias toward A-players, while admitting to missteps like over-growing the product org.

Beyond company-building, he dives into risk tolerance, luck, parenting fears, partner selection, co-founder dynamics, and how being deeply intentional—yet allowing for spontaneity—guides his personal and professional life.

Key Takeaways

Treat fundraising as building long-term relationships, not single-shot pitches.

Corcos emphasizes Mark Suster’s ‘lines, not dots’ idea: take many meetings, share metrics over time, and let investors observe your progress rather than waiting for a “perfect” moment to pitch one precious contact.

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Be radically specific and proactive in how you use investors.

Most founders under-utilize investors; Sam tracks thousands of explicit “asks,” includes a clear ‘Asks’ section in updates, and crafts time-bounded, concrete requests (e. ...

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Use transparency and the keeper test to maintain a high-talent culture.

Levels shares internal one‑on‑ones and performance feedback by default and applies Netflix’s keeper test; when someone doesn’t pass, they discuss it openly, which Sam says increases trust and often rallies support around underperformers.

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Optimize team structure: more great engineers, fewer unnecessary product roles.

Reflecting on mistakes, he notes Levels overbuilt its product org; like Brian Chesky, he’s concluded product management should be leaner while strong engineers are often the higher-return investment.

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Send materials ahead and let uninterested investors self-select out.

Contrary to the “never send the deck early” advice, Sam prefers to share deep Notion docs before meetings; those who read and still want to meet are already aligned, saving him time and avoiding superficial, repetitive conversations.

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Know exactly what you’re optimizing for—both in life and in work.

From spontaneous travel to rigid scheduling and relationship ‘one-pagers,’ he argues the key is intentionality: decide whether you’re optimizing for serendipity, experiences, or specific outcomes, and design your behavior accordingly.

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Address emotional friction with co-founders quickly but thoughtfully.

When he noticed resentment toward his co-founder, he scheduled a candid conversation within a day, unpacked the feeling, and resolved it; he cautions against letting such issues linger for months or years.

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Notable Quotes

When you’re fundraising, you’re a prophet, not a missionary.

Sam Corcos

One of the major mistakes that people make early on is they treat investor contacts like precious gems.

Sam Corcos

If ultimately you cannot get behind the idea then you have lost confidence in the CEO… you should probably leave the company.

Sam Corcos

If you don’t know what you need, you’ve already failed when an investor asks, ‘How can I help?’

Sam Corcos

I try to be very intentional with my time. Most people are not very intentional with how they spend their time.

Sam Corcos

Questions Answered in This Episode

How far can radical transparency be pushed before it starts to damage psychological safety and trust within a company?

Sam Corcos, CEO and co-founder of Levels, discusses how extreme transparency, intentional time management, and a wide-net fundraising strategy shape how he builds companies and relationships.

Get the full analysis with uListen AI

What practical steps can a first-time founder take to build the kind of investor network that a serial founder like Sam relies on?

He advocates taking as many investor meetings as possible, treating fundraising as building long-term lines, not one-off dots, and being ruthlessly specific about what help you need from investors.

Get the full analysis with uListen AI

How should founders balance the trade-off between optimizing for many small, high-value angel checks versus a few large institutional checks?

Internally, he shares how Levels uses radical transparency on performance and one‑on‑ones, the Netflix-style keeper test, and a strong bias toward A-players, while admitting to missteps like over-growing the product org.

Get the full analysis with uListen AI

In what ways might over-structuring time and relationships backfire, even when done with the best intentions of ‘being intentional’?

Beyond company-building, he dives into risk tolerance, luck, parenting fears, partner selection, co-founder dynamics, and how being deeply intentional—yet allowing for spontaneity—guides his personal and professional life.

Get the full analysis with uListen AI

How can startups experiment with keeper-test-style performance management without creating fear and politics in their early teams?

Get the full analysis with uListen AI

Transcript Preview

Harry Stebbings

Do you agree with Vinod Khosla that 90% of VCs actually detract value?

Sam Corcos

It's a little bit challenging because when you're fundraising, you're a prophet, not a missionary. You have the vision and you're trying to get people who already get it. You're not trying to convert people to your religion. I think one of the major mistakes that people make early on is they treat investor contacts like precious gems. The reality is that-

Harry Stebbings

What was the best first investor meeting that you had?

Sam Corcos

I think the best we had was with-

Harry Stebbings

Sam, I am so excited for this. I was just running on the treadmill. I was listening to you and Tim Ferriss, and it was the worst episode to listen to running on a treadmill because I was constantly typing notes, which is a great sign. But thank you so much for joining me first.

Sam Corcos

Glad to be here.

Harry Stebbings

Now, I would love to start with a little bit of background. I always find actually what people wanted to be when they were younger very informative. When you were a child, what did you want to be when you grew up?

Sam Corcos

My first real memory was I wanted to be a scientist. I was fascinated by biology and oncology, so I think it was a research scientist.

Harry Stebbings

(laughs) Well, you know, there's still time. There's always a second chapter, Sam.

Sam Corcos

Yeah. (laughs)

Harry Stebbings

Um, were your parents pushing you to be a doctor? You're not an Asian child and so I don't think they were like beating you to either be an engineer or a doctor. (laughs)

Sam Corcos

Yeah, well, I- I do have Jewish parents, so doctor or lawyer were the- the default two choices. (laughs)

Harry Stebbings

I- I- I've learned, you know what? We can only, uh, we can only disappoint parents. Um, but I wanna start with a story that Vinay at, uh, Loom told me.

Sam Corcos

Uh-huh.

Harry Stebbings

And he said that, uh, he encountered you one day in the street when you weren't with a home base, we should say. And, uh, you asked him if you could stay the night.

Sam Corcos

Yeah. (laughs)

Harry Stebbings

Can you talk about that story, Sam?

Sam Corcos

Yeah. I- it's, uh, from the perspective of Tom, who was, uh, on our growth team. I had just landed in New York to spend some time with him and other people, and he asked me where I was staying, and I said, "I don't know. That's a, that's a, like, multiple hours from now problem." And he said, "Well, what- what do you think is gonna happen? Like what normally happens in these situations?" And I said, "You know, I'll run into a friend and then I can stay with them. Worst case, I get a hotel." And then about 30 minutes later, I bumped into Vinay walking through Washington Square Park. He mentioned he had just arrived. He had an extra bedroom in his Airbnb. I asked him if I could stay there, and that was it. And Tom, I think, is absolutely convinced that I staged that whole situation. (laughs)

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