✨ Hey! Louis here, founder and CEO@Upstream.
This blog post is part of our Startup & Company Building stories, in which Jonathan and I share learnings from our founding journey with Upstream (YC S23). None of this would be possible without our early (dream) team: shoutout to our stars Joseph, Ben, Kostya, Sarah, Patryk.✨
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Fundraising is hands down the most nerve-wracking process any founder can go through.
Picture this: You believed enough in your idea to go all in. You’ve been working yourself silly on your startup for months. You’ve sacrificed so much for it: sleep, quality time- money 💰.
And now, it’s not enough to build something people want. You have to build something VCs want.
Somehow, it gets worse if you’re an introvert.
The truth is that fundraising is a sales process just like any other. So how do you do ace your fundraising?
When I coach early-stage founders on fundraising, I remind them of one simple truth:
Most VCs don’t have your depth of expertise in your market. They’re making a gut call in 30 minutes.
And that’s exactly why your attitude matters so much in your early interactions.
In summary: In every fundraising meeting, coach yourself to speak like the expert and frame the conversation.
Why your attitude matters more than what you think
Wby your attitude matters more than what you think
VCs meet dozens of startups each week. Even those who specialize in your space aren’t operating at your level of depth.
What this means is that your job is to frame the opportunity and teach them how to think about it.
You are the domain expert: act like it and speak like it. Don’t rely on jargon or deep tech to impress, but instead try to make the problem as clear and understandable as possible.
You decided to launch this company, so you should have made the case for yourself that you are solving a huge pain in the best possible way. Go for it!
💡1. Investors are market outsiders (relative to you)
VCs meet dozens of startups each week. Even those who specialize in your space aren’t operating at your level of depth.
What this means is that your job is to frame the opportunity and teach them how to think about it.
You are the domain expert: act like it and speak like it. Don’t rely on jargon or deep tech to impress, but instead try to make the problem as clear and understandable as possible.
You decided to launch this company, so you should have made the case for yourself that you are solving a huge pain in the best possible way. Go for it!
💪 2. Confidence is the strongest early signal you can send
Especially for the first meeting, where you only have 30 minutes to make an impression.
Fundraising is part performance. People trust leaders who sound like leaders. Your ability to communicate clearly becomes a proxy for your execution ability.
"I know this space, I know this problem, and I’m the right person to solve it."
But mind you: true confidence comes from a deep understanding of your market, so don’t skip your homework: be an actual expert.
Pro tips to implement and execute in meetings
🤓 Know each and every one of your market/problem/solutions convictions by heart
One thing I did during our pre-seed fundraising was to write down all the reasons I believed in Upstream and our bets to win in the space. I would re-read it before every meeting to make sure Iw as able to drive the point home during the meeting.
More on my fundraising routine in the next section 🙂
That’s the price of building a truly world-class team. No shortcuts.
❓Reframe VC questions
One of the best tools I coach founders to use:
If a VC asks a misaligned or surface-level question, reframe it:
“You asked X, but I think the real question is Z — and here’s how we’re thinking about it.”
This subtle shift does three things:
Positions you as the expert.
Prevents you from chasing irrelevant threads.
Puts you in control of the conversation.
🍫 Reframing Example - Cybersecurity SaaS
VC Question: "How are you different from CrowdStrike?"
Bad reframe (evasive): "You're asking about CrowdStrike, but the real question is market positioning..."
Good reframe (direct + insightful): "You're asking about CrowdStrike, but I think the real question is whether endpoint detection is even the right battleground anymore. Here's what we're seeing in the field:
CrowdStrike is phenomenal at catching threats that have already breached your perimeter. But 73% of successful attacks in 2024 came through SaaS app misconfigurations - think exposed S3 buckets, overprivileged OAuth tokens.
CrowdStrike can't see those because they're not on endpoints. They're in your cloud infrastructure. That's why we built for SaaS security posture management instead of trying to build a better endpoint tool."
The key is pivoting from their surface-level question to the strategic insight that only you, as the domain expert, would know to focus on.
Original Insight: the confidence loop
It’s simple: the more clearly you explain the market, the more a VC trusts you.
That trust:
Increases likelihood to invest
Enhances their confidence in your leadership
Fuels momentum for future conversations
This is the “Confidence Loop”, and it starts with how you show up on the call.
🎯 My pre-pitch ritual: The “Expert Mode” Reset
Every fundraising conversation is a mini-performance. My personal reset routine helps me show up with clarity and conviction:
🚫 Avoid back-to-back calls
⏳ Carve out 5 minutes of quiet buffer time
🎵 Play one song that helps you shift into “domain expert” mindset
It’s small, but it creates a huge difference in how I show up.
👉 Key Takeaway
VCs don’t need to understand every technical nuance. They need to believe:
You understand the market deeply.
You’re the person to solve this problem.
You can communicate that clearly to future hires, customers, and investors.
Confidence—anchored in clarity—is what unlocks that belief.
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🧠 FAQ
Q: What if I need time to think before answering their questions?
It's completely fine to pause. Try: "That's a great question- let me think through the best way to frame this." Use the 2-3 seconds to collect your thoughts. VCs respect thoughtful responses over rushed ones.
Q: How do I handle it when they interrupt or talk over me?
Lean into your prepared anchor points. When there's a natural pause, redirect: "Before we move on, I want to make sure I've clearly explained why now is the perfect timing for this market." Your preparation becomes your confidence shield.
Q: What if they ask something I genuinely don't know?
Own it confidently: "I don't have that data point with me, but here's what I do know about [related area]..." Then pivot to something you're certain about. Honesty + expertise in adjacent areas shows maturity.
Q: I freeze up when they challenge my assumptions. How do I stay composed?
Remember: they're not attacking you, they're stress-testing the opportunity. Reframe it as teaching: "I understand the skepticism- I had the same concerns before I saw [specific evidence]. Here's what changed my mind..."
Q: What if the conversation goes off-track and I lose control?
Have 2-3 transition phrases ready: "That's interesting, and it actually ties back to our core thesis that..." or "You're touching on something important- the real insight we've discovered is..." Practice these until they feel natural.
Q: How do I follow up without seeming desperate?
Send a thoughtful follow-up within 24 hours that adds value: "I realized I didn't fully address your question about [topic]. Here's additional context..." Include one piece of new information or a relevant customer insight. Value-add beats frequency.
Related Resources
How to Build Your Seed Deck - Y Combinator's comprehensive guide to structuring your pitch deck and messaging
The Fundraising Framework - NFX's step-by-step breakdown of the fundraising process, from preparation to closing
First Round's Pitch Advice - First Round Review's guide on crafting compelling narratives for investor meetings
