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Two years ago, I knew nothing about how venture capital worked, and it was bizarre to me that an investor would give a college dropout millions of dollars to build their dream.
But through the community I was building, I had the opportunity to become more involved and angel invest in the entrepreneurs in my network. In March 2024, I took it a step further and joined Next Wave NYC, a pre-seed venture fund, as an Investment Partner. Now, together with a group of experienced founders + operators from OpenAI, NVIDIA, Chief, and Snowflake, we back the “Next Wave” of founders in NYC.
I’ve reviewed 500+ pitch decks and met with 2,000+ founders, and I’ve seen first-hand the types of startup pitches that work vs the ones that don’t. I’ve seen people raise tens of millions of dollars effortlessly while other brilliant entrepreneurs with unique ideas completely fumble their way through startup pitches.
It’s a shame because the fundraising process is often foreign and counterintuitive for first-time founders. And if they don’t understand the fundraising game, it doesn’t matter how good their idea is, they might not ever get funded.
So, my goal today is to share the 10 things I’ve learned about How to Pitch Your Startup… from the other side of the table.
Btw, if you’re around on April 9, I'm hosting a fireside chat with Jeffrey Bussgang, General Partner, Co-founder of Flybridge + Senior Lecturer at Harvard Business School, about how entrepreneurs can find product-market-fit in the AI era.
Jeff teaches one of the most popular classes at HBS on entrepreneurship and venture capital, and our session will be like a micro HBS course, distilled into 60 minutes and packed with insight. You don’t want to miss this!
1. Cold outreach is good, but warm intros are king:
Cold emails and messages can work, but warm intros are a million times more effective. Two ways to build better relationships before you fundraise:
Expand your people surface area. Get in the room. Go to industry events. Meet more people. Some call this “cushioning” - building genuine connections before you need them.
Give before you ask. Share insights, make intros, or help others in small ways before you ever pitch them. Relationships compound.
2. Don’t skip your backstory:
At the earliest stages, investors bet on founders first, ideas second. Your track record, grit, and ability to execute are what make people want to invest.
Make sure you sell yourself:
What have you accomplished?
What makes you uniquely qualified to build this company?
Why are you a machine who won’t stop until this works?
Too many founders skip over their backstory and jump straight into the product and market. No, we want to hear about why YOU are awesome.
3. Don’t monopolize the conversation:
A great pitch is a conversation, not a one-way monologue. Your goal within the 30 minutes is not only to explain your idea and vision, but to answer any lingering questions in the investor’s head too.
Some investors prefer a deep-dive discussion. Others want a tight, polished pitch. Some just want you to share your screen and show them what you’ve built. Remember to read the room.
4. Don’t always stick to the script:
Common wisdom tells you that startup pitches should always follow the same format and template. But I recently chatted with two founders—one who raised $400M throughout the journey of the company, his first deck was 140 slides. Another who just raised $10M… but he didn’t have slides at all.
The key is to find the best way that is natural to you and brings out your best strengths. If you’re a great storyteller, lean into narrative. If your product is insanely good, do a live demo. If numbers are your strong suit, let the data lead.
As a general rule, 10 slides is fine, but don’t force a template if it doesn’t fit your style.
5. Don’t miss the golden question: “Why now?”:
Most investors see hundreds of pitches, so the real question they’re asking isn’t just why this company; it’s why now?
Airbnb, Uber, Snap… none of these were original ideas. Variations of them existed before, but at the wrong time. And that made all the difference.
6. Master the hard questions:
Investors will poke holes in your vision. They’ll challenge your market size, your product defensibility, and whether you’ve actually done the deep work to diligence your own idea.
Prepare for the toughest questions ahead of time:
Market:How big is this, really?
Product:Why is this 10x better than the alternatives?
Vision:If this works, what does the world look like in 5-10 years?
7. Don’t underestimate speed:
How fast you get stuff done says everything about how you operate as a founder. Investors are always looking for positive signals—speed is one of them. I’ll build on this with my hot take: The speed of your email responses matters.
I was recently on the fence about investing in a company. I sent them an email with five questions. Nothing crazy, just things I needed clarity on. Within 20 minutes, they responded with detailed, well-thought-out, and perfectly articulate answers.
That speed told us everything we needed to know. The other partner on the deal texted me immediately: We were in.
The other investing partner’s response:
8. Pitch from a position of strength:
i.e., don’t act too desperate.
As a founder, you should have the absolute conviction that your idea is unique and that you are the right person to bring it to life. So, any conversation with an investor isn’t about trying to convince them to give you money; it’s about giving them the opportunity to be a part of your journey.
Be confident. Be honest about the risks. And remind yourself: money is abundant. There are more investors than great companies to invest in. The best founders know that investors can smell desperation from a mile away.
9. Don’t underestimate momentum:
The most effective fundraises I’ve seen are intentional, purposeful, and driven by urgency.
Intentional – Only pitching when fully prepared and targeting the right investors.
Purposeful – Having a clear use case for the capital you’re raising.
Urgent – Running a tight, structured process with clear deadlines.
Fundraising should be fast and efficient: get in, get your capital, and get back to building your company.
On the contrary, the most ineffective fundraises I’ve seen have been dragged over years, with no urgency, no clear next steps, and no end in sight.
✅ Stay on track with our Fundraising Tracker!
Momentum is everything when raising capital, so I built a fundraising tracker to help you stay organized, keep investor details in one place, and maintain momentum throughout your raise. Get it here.
10. Don’t fumble your pitch:
Now that you have all the ingredients for a good pitch, remember the only way to improve is to practice.
Practice in front of your friends. Nail specific moments and transitions. Prepare for objections. Make sure your demo is working. Catch any typos. The delivery is often just as important as the content.
But remember, at the end of the day, the perfect pitch or the smoothest fundraising process is nothing without the fundamentals of an ambitious idea, a big vision, and a growing market.
💻 Use my fundraising tracker: I built a fundraising tracker to help you stay organized, keep investor details in one place, and maintain momentum throughout your raise. Get it here.
🖥️ Join our online workshop: On April 9, I’m co-hosting an online workshop with Naomi Goez, Principal at Forum Ventures, on How to Pitch Your Startup. Save your spot here.
The only way to stop the rat race — As someone who “escaped” the traditional corporate rat race, only to join the big tech rat race, and then the bootstrapped entrepreneur rat race—this hits home. No matter where you are, the grass always seems greener.
Have a job to share? Let me know by replying to this email.
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🖼️ Behind the Scenes
Four years ago, I met Euwyn Poon, co-founder of Spin, the mobility company that later sold to Ford. He was one of the first people I connected with when I moved to New York during a time when everyone else seemed to be leaving.
I always thought he was brilliant. But it wasn’t until he shared the behind-the-scenes founding journey of Spin - off the record, in a closed-door conversation at Lumos House Austin - that I realized how extraordinary his journey was.
It made me realize that we need more of these off-the-record, private conversations where entrepreneurs can be honest about their founding journey.
So, on May 16, we’re making it happen. Together with Ankur Nagpal (Co-founder of Teachable, sold for $200M), we’re hosting The OOO Summit, an invite-only event bringing together the smartest builders, founders, and operators.
If you want to hang with brilliant people like Euwyn, save your spot here.
Early bird tickets are just $99 ($100 off) with code “WEREBACK”. This ends on March 20!
With Euwyn Poon (Co-founder of Spin) at Lumos House Austin
Great common sense perspective! Founders love their product or service and want to expound on the beauty and technical capabilities but that is not always what investors like to hear. This is a good guide which I will be sharing with the startups I advise.
Great common sense perspective! Founders love their product or service and want to expound on the beauty and technical capabilities but that is not always what investors like to hear. This is a good guide which I will be sharing with the startups I advise.
Still early in my own VC journey, and this really helped frame the gap between good ideas and investable ones. Bookmarking this — thank you.