What Top-Tier VCs ACTUALLY Want to Know: 10 Questions to Nail Your One Shot with Silicon Valley’s Elite (From 269,000 Words of Seed-Stage Transcripts)

You only get one shot at making a first impression, so you better make it count. Especially when you meet with investors to raise money for your startup, particularly if you’re early stage.

And you can’t afford to wing it.

My team and I have been very fortunate to meet with some of the most prominent venture capital firms in the world. They excel at what they do because they know how to ask the right questions—something they’ve perfected through extensive practice.

The very best salespeople show up prepared. They know what kind of questions to expect, have the right answers, and can anticipate (and consequently pre-empt) objections. The same could be said about founders that have mastered the art of fundraising. But there’s a big difference.

You don’t get to target practice. Each and every meeting counts. You only get one shot… and you won’t have that many venture capital firms on your shortlist. So how do you prepare for that?

This is the answer to that question.

I sat down to analyze some 269,000 words (from dozens of hours of transcribed conversations) between our team and some of the world’s leading venture capital firms, including Sequoia Capital, Google Ventures, EQT Ventures, Mosaic, Bessemer, Lakestar, and others.

And you know what happened? Certain patterns and trends emerged. Specific questions, statements, and objections repeatedly surfaced.

Showing up prepared can make all the difference.

Understanding the common patterns in VC questions, objections, and perspectives helps you make a lasting first impression, address objections effectively, and increase your chances of securing investment.

In this first article I’ll outline the ten most important questions you need to prepare for when meeting with seed-stage investors. You’ll see actual excerpts from our meetings, my commentary and reflections, and a couple of bullet points on what you can do to prepare.

My sincere hope is that it can function as a way for founders to show up and be better prepared and for investors to have even better and more meaningful conversations with the companies they may back. Win-win.

Note: While these transcripts focus on B2B sales and marketing tech, the underlying principles apply to almost every industry. The questions might be phrased differently, but the VC mindset remains the same.

1. What's the Problem, and Why Is It Burning NOW?

"You mentioned you're targeting [customer segment X]. Where do you think the pain point is the most acute?" 

 "...when did you guys kind of come together on the...idea?" 

VCs are obsessed with timing. It’s not enough to identify a problem – you need to prove why it’s a burning need today and why your solution is the answer at this precise moment.

They want to understand why you’re building this company now, and they’re looking for startups capitalizing on a specific “why now” moment – a shift in market dynamics, a technological advancement, or a new customer need.

How to Prepare:

• Quantify the Pain: Use data, research, or compelling customer stories to illustrate the scope and urgency of the problem.

  Connect to Current Trends: Show how your solution aligns with current market shifts, technological advancements, or regulatory changes.

  Make It Visceral: Paint a vivid picture of the problem’s impact, making it relatable and emotionally resonant for the investor.

  Show Why This Moment is Unique: Explain what’s different now compared to the past and why your solution is poised for success in the current landscape.

2. Who are Your Ideal Customers, and Can You Prove They Exist?

"What is the distribution across the two ICPs you mentioned? Are there any customers that are not startups...?"

VCs want to know that you can pinpoint your ideal customers with laser precision and that you've validated their needs directly. They want to see that you have a real understanding of your audience, and that these potential customers are real, reachable and ready to pay.

How to Prepare:

• Go Beyond Demographics: Show that you've spoken to real customers, validated their needs, and understand their buying behaviors.

• Present Early Evidence of Demand: Share data from customer interviews, surveys, or early sales to prove market traction.

• Articulate the "Why Now" for Your Customers: Explain why your target customers are motivated to buy today and what's driving their urgency.

3. What's Your "Secret Sauce," and Why Can't Anyone Else Replicate It?

"What are the other... companies...trying to redesign the category... using...new technology? What are some comparables?"

"The key for us is understanding what the defensibility is in these companies over time. Right? How does company A from company B...differentiate?"

This is about defensibility and “moat”. Early stage investors want to know what's truly unique and difficult to copy about your solution, ensuring a lasting competitive advantage.

 How to Prepare:

• Define Your "Unfair Advantage": Clearly explain what sets you apart from competitors and why it's difficult for them to catch up.

• Think Beyond Features: Your moat could be technology, data, network effects, brand, or even a unique go-to-market approach.

4. Show Me the Traction: Metrics Speak Louder Than Words and Numbers Don't Lie (But People Sometimes Do)

 “...when it comes to the fundraising, where are you at...with the timeline and..."

Be prepared to back up your claims with evidence. VCs want to see numbers that demonstrate real progress: paying customers, revenue growth, engagement, or other relevant metrics.

That being said— Don't be afraid to share "ugly" early metrics. VCs appreciate transparency, and even modest traction can be compelling if it demonstrates progress and learning.

 How to Prepare:

• Doesn’t Have to be Perfect: Focus on your most impactful metrics and the story they tell about your progress, even if they're not perfect.

• Track and Measure Key Metrics: Customer acquisition, revenue, engagement, or other indicators that demonstrate progress.

• Showcase Early Wins: Highlight positive customer testimonials, case studies, or early wins that validate your value proposition.

• Be Transparent and Realistic: Don't exaggerate your achievements. Honesty and transparency build trust with investors.

5. Go-to-Market Strategy: Beyond "Just Add Salespeople" 

 "...how you're thinking about distribution and what your metrics are gonna be for...working with those early engagements?"

"How are you... going to market... how you're thinking about... replacing existing tooling? Does it work alongside...?"

VCs are seeking innovative go-to-market approaches that go beyond simply hiring a sales team. They're looking for strategies that leverage product-led growth, partnerships, and efficient customer acquisition.

 How to Prepare:

• Think Beyond Traditional Sales: Explore PLG tactics, content marketing, community building, and creative partnerships.

• Demonstrate CAC Efficiency: Show how you'll acquire customers cost-effectively and optimize your marketing spend.

6. Pricing: Don't Be Afraid to Charge What You're Worth (But Start Low)

“ ...nine hundred dollars is that...also works for...young companies? It seems pretty pricey?”

VCs are looking for pricing strategies that balance attracting customers with generating meaningful revenue. They'll scrutinize your pricing model, tiers, and ability to upsell. VCs want to see that you understand your value and can charge accordingly.

However, at the seed stage, a lower entry price point can be strategic for driving initial adoption and gathering customer data.

How to Prepare:

• Justify Your Pricing Based on Value: Clearly articulate the ROI for your customers and why your pricing is justified.

• Experiment with Different Models: Explore freemium, subscription, usage-based, or value-based pricing to find the right fit for your market.

• Show a Path to Sustainable Growth: Demonstrate how your pricing strategy will contribute to long-term profitability.

7. How Does AI Give You a Sustainable Edge (Beyond the Buzzword)?

“Many new startups try to leverage LLMs...but...we had the feeling...it's a rather thin wrapper around the LLMs....”

VCs are looking for companies that are using AI to create a lasting competitive advantage, not just riding the AI hype wave.

 How to Prepare:

• Highlight your AI "secret sauce": Explain the specific AI technologies you're using and how they create a true competitive advantage.

• Showcase your data strategy: Demonstrate how you're capturing, enriching, and analyzing data to power AI-driven insights.

8. Integration: Make It Easy to Say "Yes" (Without a Six-Month Migration)

 "The CRM marketing is definitely transitioning...The older...players have not much of the speed, and I think the new players...have the advantage."

VCs know that B2B buyers are hesitant to adopt solutions that require complex or disruptive integrations. Show how your product fits seamlessly into existing workflows and systems.

How to Prepare:

• Prioritize Integrations with Popular Platforms: Make it easy for customers to connect your solution to their existing CRMs, marketing automation tools, and other critical systems.

• Offer Flexible Deployment Options: Provide both standalone and integrated versions of your product to cater to different customer needs and preferences.

9. Data: Your Most Valuable Asset (and a Potential Liability)

"...at least at scale... It needs to be in a transparent way where...you send a link...you say click here, and you'll see all the notes which have been captured."

VCs recognize the power of data, but they're also increasingly concerned about privacy, security, and ethical implications. Demonstrate that you're handling data responsibly.

How to Prepare:

• Be Transparent About Data Usage: Explain how you're using data to power your AI, but emphasize your commitment to user privacy and security.

• Stay Ahead of the Regulatory Curve: Be informed about evolving data privacy regulations (e.g., GDPR) and ensure your practices are compliant.

• Build Trust Through Transparency: Communicate your data policies clearly and be upfront about any potential implications for customer data.

10. What Does Your Team Bring to the Table?

 "…and you guys met at Spotify or before that?" 

“And how do you work as a product team?... Is it like...there's PM? There's product designer? Engineering? Or how it's set up, how you work, how you push things?”

VCs invest in people as much as ideas. They're evaluating your team's experience, expertise, and ability to execute the vision.

How to Prepare:

• Tell the team's story: How did the team come together? What unique skills and experiences does each member bring?

• Showcase relevant expertise: Highlight past achievements, industry knowledge, and technical capabilities.

• Demonstrate strong team dynamics: Convey a sense of shared vision, collaboration, and a positive team culture.