The 10 Questions That Reveal a VC’s True Character
How to reference check your investors before signing them on.
Doing reference checks on investors might not always matter, especially if you are the type of founder who can command the VCs and ask them to wire the money and then just make them step out of the way.
But for 99% of the founders out there, especially ones who are raising for the first time, a thorough reference check process will make a lot of sense, especially if you are able to pick from several VCs who want to lead your round.
Even if there's one investor you are talking to, you should still consider who you are bringing on your cap table. They will be with you for years, possibly decades, as part of the company. If you want it or not, their behavior and reputation will still become linked with your company.
The best time to run reference checks is right after an investor signals serious intent, ideally when they say they want to invest. At that point, you should clearly communicate that you’ll be speaking with founders they’ve backed. After all, just as they’ll be doing diligence on you, you have every reason to do the same on them.
If I would be a founder, raising a round from investors, here's how I would conduct reference checks on an investor.
Preparation
I’d speak with at least three founders who’ve previously raised from the investor, and I’d aim for diversity: talk to one whose company failed, one that’s still operating but hasn’t scaled dramatically, and ideally one who’s doing really well or has exited. This gives you a well-rounded view of how the investor behaves across the full spectrum of startup outcomes. Pay close attention to questions like, “How did they respond when things went wrong?” These answers often reveal the investor’s true character.
Schedule these meetings as video calls, so that you can easily record the call and take notes. There's no need to share the questions beforehand, as it will give the founder too much time for preparation and often soften their response, when you want transparency and honesty.
The ten questions
Here, I will share my top 10 questions. These questions attempt to discover behaviors that only founders would spot, and many of them are meant to understand how they work with founders in stressful moments.
1. "Can you tell me how you met the investor, how was the negotiation phase before the investment, and how long were they involved with your company?"
First, understanding how they met the investor reveals the VC's sourcing approach and network. Were they proactively seeking investments in that space? Did they come through a warm introduction? This gives you insight into how the investor typically finds and evaluates opportunities, which can indicate their level of expertise and commitment to your sector. In other words, how serious are they at their job? I’ve noticed that investors who actively pursue outbound opportunities tend to have a stronger focus on long-term potential, compared to those who primarily rely on opportunistic inbound deals.
The negotiation phase details are crucial because they show the VC's true operating style. You'll learn important aspects about their character: whether they're straightforward, try to renegotiate settled terms, if they move quickly or drag out the process, whether they're reasonable with their demands and transparent about their concerns, and most importantly, how they handle disagreements during tense moments.
The duration of involvement tells you several important things about the investor's long-term behavior. If they're still involved, it suggests they maintain long-term relationships and support. If they exited, you can learn about their behavior during different phases of the company. The length of the investor’s involvement also helps you assess whether they remained actively engaged or drifted away after the initial check. It also gives you a sense of how recent, and therefore relevant, their experiences and insights really are.
2. "How accessible are they? Do they respond quickly when you need them? (For bigger VC firms) Did you get to spend time with the people you wanted at the firm?"
This question helps reveal the true nature of the investor's day-to-day relationship with portfolio companies and their operational approach after the investment closes. Understanding their accessibility and responsiveness patterns gives you insight into what working with them will actually be like, beyond the courting phase when VCs are typically highly responsive.
For larger firms, the question about access to specific team members is particularly crucial because during the pitch process, you'll often meet partners and specialists who seem eager to help. However, post-investment reality can be quite different. You want to know if portfolio companies actually get meaningful time with senior partners, domain experts, or operating partners who were showcased during the fundraising process, or if they get delegated to less experienced team members.
The response time aspect is important because many critical business situations require quick investor feedback. Whether it's an urgent hiring decision, a strategic pivot, or an unexpected crisis, knowing how quickly the VC typically responds can help you understand if they'll be of help during crucial moments.
Continuing from my outbound vs inbound comment earlier, the investor's accessibility style can reflect on their broader investment philosophy and how they view their role. Some investors maintain close contact because they want to be genuine partners in building the business. But others might be more hands-off because they trust founders to operate independently. Neither approach is in itself wrong, but you need to know which style matches your needs and expectations.
3. "What specific ways have they helped your company grow (introductions, hiring, strategy)?"
You might say that this doesn't matter that much as you want their money and then you want them to get out of the way. But the main reason for this question is to uncover the true nature of their partnership approach. Early-stage investors who add genuine value can dramatically accelerate a company's trajectory.
When you ask about specific contributions, you're looking for concrete examples rather than vague claims. Did they actually open doors? Did they help during strategy inflection points? The specificity reveals whether they're hands-on partners or simply capital providers.
This question also exposes their working style. Are they assertive and directive? Are they proactively identifying opportunities? Do they respect founder autonomy while still offering substantive support?
The introduction aspect is particularly telling. Making valuable introductions for portfolio companies is often the most impactful way VCs can help at the pre-seed stage. If an investor hasn't been connecting their founders to customers, talent, or follow-on capital, that's a red flag worth exploring further.
Ultimately, this question helps you distinguish between investors who view themselves as true company builders versus those who see themselves primarily as financial backers.
4. "How strong is their network, and do they actively leverage it for portfolio companies?"
This question helps you evaluate one of the most important aspects of VC value beyond just capital - their network leverage capabilities.
When you ask previous founders about the investor's network strength and how actively they deploy it, you're uncovering whether the VC's claims about "opening doors" actually materialize post-investment. Many investors tout impressive networks during pitch meetings, but the reality of how effectively they make introductions varies dramatically.
Previous founders can tell you if the investor proactively makes meaningful connections or if you'll need to constantly request help. They can share whether introductions were to high-level decision makers or just perfunctory connections. You'll learn if the VC's network extends beyond their immediate circle into areas that might benefit your specific business needs.
The quality of introductions matters tremendously. Some investors make thoughtful, warm introductions with proper context that lead to productive relationships, while others might simply share contact information or make superficial connections that go nowhere. Former portfolio companies can tell you which category this investor falls into.
This question also reveals how the investor thinks about their role in your company's growth. Do they see themselves as active partners in building your business, or more as passive capital providers? Their approach to leveraging their network often reflects their broader investment philosophy and engagement style.
For pre-seed companies especially, these network effects can dramatically impact your trajectory, helping with everything from recruiting key talent to securing early customers or partnerships. Understanding exactly how the investor has helped other companies with similar needs gives you realistic expectations about what value they'll bring beyond their check.
5. "How did they behave in subsequent funding rounds? Did they follow on or help attract other investors?"
A strong investor becomes an invaluable fundraising ally when you're ready for your next round. They should proactively leverage their network to connect you with appropriate later-stage firms that match your company's needs and trajectory. The quality of these introductions—whether they're warm, thoughtful connections to decision-makers versus generic referrals—can dramatically impact your fundraising efficiency.
Their willingness to advocate for you speaks volumes. Do they actively champion your company to other investors? Do they help refine your pitch based on what resonated with them? Do they provide credibility by sharing why they invested and their positive experience working with you? These endorsements can significantly influence new investors' perception of your company.
Even without contributing additional capital themselves, valuable investors prepare you for future fundraising by helping strengthen your narrative, advising on timing, and providing guidance on deal terms. They understand the evolving funding landscape and help position your company advantageously within it.
6. "How do they react to bad news, or to situations like when the company pivoted or missed a target?"
Former portfolio founders can tell you whether the investor maintains composure and provides constructive guidance during crises or if they become punitive and add pressure. Some investors present themselves as founder-friendly during good times but transform into demanding critics when targets are missed or when market conditions change unexpectedly.
Their reaction to pivots is especially telling. Strong investors understand that early assumptions often require adjustment and will support thoughtful changes in direction with additional resources and connections. Others may resist necessary pivots, creating friction when you need flexibility most.
The best investors distinguish between temporary setbacks and fundamental problems, remaining steady during the former while helping address the latter. They bring perspective from other portfolio companies, suggesting practical solutions rather than just highlighting problems.
7. "What's the biggest disappointment or challenge you've had working with them?"
Former founders are typically hesitant to speak negatively about their investors, so framing the question around "disappointments" or "challenges" creates space for honest feedback without requiring outright criticism. Their answer often reveals the investor's blind spots, communication issues, or areas where they overpromised and underdelivered.
Pay close attention to patterns across multiple references. If several founders mention the same challenge, it likely represents a consistent issue rather than a one-off situation. Common themes might include responsiveness problems, micromanagement tendencies, conflict avoidance, or misalignment between stated and actual investment priorities.
The nature of the disappointment also matters. There's a significant difference between frustrations about limited network access versus ethical concerns or trustworthiness issues. Some challenges can be managed with clear expectations, while others might be dealbreakers.
8. "Would you take money from them again?"
This question is simple but powerful. It distills a founder’s entire experience with an investor into a single judgment call. The directness of the question can elicit an immediate, visceral response before the founder has time to filter their answer. Their initial reaction - whether enthusiasm, hesitation, or reluctance - tells you more than their detailed explanations might.
Pay attention not just to the yes or no, but to the qualifications that follow. A founder might say "Yes, but only if..." or "No, unless..." which can reveal specific circumstances where the investor shines or struggles. These conditions often highlight the investor's particular strengths and weaknesses that might be relevant to your situation.
This question also naturally prompts founders to consider their full journey with the investor - from initial pitch through exits or challenges - providing a comprehensive evaluation that goes beyond isolated incidents. It reveals whether any disappointments or conflicts were ultimately outweighed by the value the investor brought.
The answer gives you insight into the long-term relationship quality, which is critical since you'll potentially be working with this investor for 5-10 years. A founder who would enthusiastically take money again is telling you that despite inevitable bumps, the investor was ultimately worth the partnership.
9. "What type of founder or company would be a good fit for this VC?"
This question reveals the investor's true strengths, preferences, and operating style beyond their public marketing. Every VC has specific types of founders and companies they work best with, regardless of what their website claims.
Former portfolio founders can tell you if the VC is better with technical founders who need business guidance, or business-focused founders who need technical resources. They can share if the investor thrives with first-time entrepreneurs who need hands-on mentoring or if they prefer seasoned founders who require less direction.
The answer often exposes the investor's unspoken biases and comfort zones. Does the VC work well with confrontational founders or those who are more collaborative? Do they connect better with methodical builders or aggressive growth-hackers? Understanding these preferences helps you assess whether your personality and approach will mesh with theirs during challenging periods.
Beyond founder fit, this question uncovers the investor's genuine sector preferences. Some VCs excel with capital-efficient SaaS companies but struggle with hardware startups despite investing in both. Others might say they're sector-agnostic but actually provide much better support in specific industries where they have deeper networks.
This perspective helps you determine if you're genuinely in the investor's sweet spot or if you'd be an outlier in their portfolio, which could impact the attention and support you receive compared to their more "typical" investments.
10. "Do they try to control decisions, or do they act as a true partner?"
Former founders can tell you if the investor respects founder autonomy while still providing valuable input, or if they attempt to override decisions when views differ. Some investors present themselves as hands-off partners but become surprisingly controlling when business challenges arise or when the company moves in directions they didn't anticipate.
Pay attention to specific examples of how the investor handled pivotal moments. Did they support founder-led decisions even when they initially disagreed? Did they offer perspective but ultimately defer to the team's expertise? Or did they use formal or informal pressure to redirect the company's path?
The answer also reveals their communication style during strategic discussions. Effective investor-partners express concerns constructively, ask probing questions, and help strengthen ideas rather than simply shutting them down. They understand the difference between governance oversight and operational management.
Final words
Here's a few more items to consider when doing these reference check calls:
Respect the founder's time but go deep. Start with your most important questions, but be prepared to explore revealing threads that emerge during the conversation.
Look for patterns across multiple references. One negative experience might be an anomaly, but consistent feedback across several founders likely reveals a pattern.
Be transparent about your concerns. If you have specific worries about the investor, share them with references to get their perspective.
Consider fit specifically for your situation. The investor might be great for some founders but not a match for your communication style or decision-making approach.
Take notes during calls rather than trusting your memory. Better yet, get an AI notetaker to join the call and record the conversation for the best notes.
Remember that all investor-founder relationships involve some challenges. Focus on identifying red flags that would be problematic for your specific company and working style.