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Source | Citation share |
|---|---|
 How to Diligence a VC - Chris Neumannhttps://chrisneumann.com/archives/how-to-diligence-a-vc | 9.3% |
 Doing Due Diligence on Potential Investors - NextView Ventureshttps://nextview.vc/blog/doing-due-diligence-on-potential-investors/ | 5.0% |
 15+ Due Diligence Questions You Really Should Be Asking Every VC You Meet | SaaStrAIhttps://www.saastr.com/what-is-the-proper-way-to-do-due-diligence-on-a-vc-firm/ | 3.5% |
 How founders might check VC references - Also by Roy Bahathttps://also.roybahat.com/how-founders-might-check-vc-references-a13bcb169301 | 3.4% |
 Doing due diligence on your investor: A checklist for founders | Airtree Ventureshttps://www.airtree.vc/open-source-vc/diligencing-your-investor-a-checklist-for-founders | 3.2% |
 How to Assess Founders During Due Diligence — Allied Venture Partnershttps://www.allied.vc/guides/how-to-assess-founders-during-due-diligence | 1.4% |
 VCs You Should Avoid: Red Flags to Spot Before Signinghttps://sheetventure.com/blog/vcs-you-should-avoid | 1.4% |
 The Ultimate Venture Capital Firms List for Founders in 2026https://www.gritt.io/blog/venture-capital-firms-list | 1.3% |
 CRV | How to Evaluate if a VC is Founder-Friendly Before Raisinghttps://www.crv.com/content/how-to-evaluate-if-a-vc-is-founder-friendly-before-raising | 1.3% |
 How to diligence VCs you’re raising fromhttps://stephmui.beehiiv.com/p/howtodiligencevcs | 1.3% |
Yes. **Diligencing the VC is at least as important as them diligencing you.** You're potentially choosing a partner who may sit on your board, influence future fundraising, control information rights, and remain involved for 5–10+ years. The highest-signal approach is **not** reading the firm's website. It's…
Yes. Diligencing the VC is at least as important as them diligencing you. You're potentially choosing a partner who may sit on your board, influence future fundraising, control information rights, and remain involved for 5–10+ years.
The highest-signal approach is not reading the firm's website. It's systematically finding founders—especially founders the VC wouldn't naturally hand you—and interviewing them.
Start by identifying:
Partner behavior can vary dramatically within the same VC, so you want to reference-check the individual who will be your partner, not simply ask whether people like the fund.
Don't accept the VC's reference list as your universe.
Create a spreadsheet with:
| Company | Partner | Investment year | Stage | Outcome | Founder(s) | Contact found? |
|---|---|---|---|---|---|---|
| Company A | Partner X | 2022 | Seed | Acquired | Jane Doe | Yes |
| Company B | Partner X | 2023 | Series A | Active | John Smith | Yes |
| Company C | Partner Y | 2021 | Seed | Shut down | Jane Smith | Yes |
Use several sources:
The partner's historical portfolio is particularly valuable. Someone who joined the current firm two years ago may have another 10–20 companies from their previous fund that tell you much more about their behavior.
This "full portfolio mapping + partner history" approach is specifically recommended for finding references outside the VC's curated list.
This is probably the biggest mistake founders make.
You want roughly:
Five to seven conversations gives you a much better picture than two hand-picked references.
In fact, the failed/struggling companies may be your highest-value references.
Ask the VC:
"Can you introduce me to a founder where the investment didn't work out as planned?" If they won't, don't necessarily walk away—but notice it.
You want to know: What does this investor look like when the company is doing badly?
Once you've built the portfolio list:
Search:
"Company Name" founderThen identify:
Then look for mutual connections.
Your warm-intro request can be extremely simple:
"I'm considering taking investment from [VC/Partner]. You previously worked with them. Would you be comfortable sharing 15 minutes about your experience?" You don't need to tell them you're trying to get dirt on the investor.
Ask:
"Who do you know who has taken money from [VC]?" Then:
"Who knows someone who took money from [VC]?" The second-degree network is often dramatically better than the obvious references.
If Partner X previously worked at Firm Y, repeat the exercise for Firm Y.
This is one of the best ways to find off-the-record references the current VC isn't going to volunteer.
Don't ask:
"Do you like Partner X?" You'll get:
"Yeah, they're great." Instead ask:
"If you were raising your next round tomorrow, would you take money from this partner again?" Then stop talking.
The hesitation is information.
CRV's recent founder-diligence guide specifically highlights essentially this question as one of the strongest diagnostic questions.
Then drill down:
"Tell me about the hardest period of your company. What did the investor actually do?" "Did they become more helpful or more difficult when things went south?" "Did they push you toward a particular outcome?"
"What are they like in a board meeting when they disagree with you?" "Have you ever had a serious disagreement? What happened?" "Do they challenge you privately or in front of the board?" "Do they respect decisions they disagree with?"
"Did they ever use their board seat or investor rights in a way that surprised you?" "Were there any terms you wish you'd negotiated differently?"
Don't ask whether they're "value-add."
Ask:
"What's the most valuable thing they actually did for you?" And:
"Can you give me a specific example?" A claimed network is worthless until someone can point to actual introductions, hires, customers, financing help, recruiting, etc.
This one is particularly important:
"Did they participate in your subsequent rounds?" "If they didn't, why not?" "How did they behave when you needed additional capital?" "Did they help you find the next investor?" A VC that writes the initial check but disappears when you need the next round may not be the partner you think you're getting.
At the end of every call:
"Is there anything about working with this investor that you think I should know but haven't asked about?" Then wait.
And if they give you something vague:
"Can you tell me more about that?" Don't fill the silence.
The objective isn't to collect complaints. It's to identify patterns.
One founder saying "they were occasionally slow on email" means little.
Four founders independently saying:
"They're fantastic until they disagree with you, and then they become extremely controlling." That's a signal.
I'd be particularly cautious about:
Independent references are important precisely because the firm's supplied references are inherently curated.
I'd ask the partner:
"How much capital remains in the current fund?" "What's your typical initial check?" "What's your typical ownership target?" "How much do you reserve for follow-ons?" "What percentage of companies receive follow-on investment?" "Under what circumstances would you not follow on?" "What's the largest check you could realistically write into our Series A/B?" You want to know whether they can actually support you through the financing journey you're likely to need.
Also understand whether your company is strategically important to this particular partner or whether you're one of 30 companies in their portfolio.
Make two columns:
| VC says | Founders say |
|---|---|
| "We're very founder-friendly" | ? |
| "We're highly involved" | ? |
| "We help with recruiting" | ? |
| "We have enormous follow-on capacity" | ? |
| "We don't interfere operationally" | ? |
| "We have no conflicts" | ? |
Then fill the right side through references.
The discrepancies are often more informative than either answer individually.
If I were taking a serious VC term sheet, I'd do this:
Day 1: Map every investment made by the relevant partner.
Day 1–2: Identify founders, including failed/struggling companies and previous-firm investments.
Day 2: Ask the VC for 3–5 references, explicitly requesting at least one difficult outcome.
Days 2–4: Conduct ~5–7 calls.
During this: Ask every reference essentially the same questions so you can compare answers.
Then: Talk to 1–2 founders you found independently who the VC doesn't know you're contacting.
Finally: Ask the partner about every material discrepancy you uncovered.
That last step is important. You're not trying to conduct a secret investigation; you're trying to understand the relationship before entering it.
The best recent guidance I've found reaches essentially the same conclusion: don't rely on the firm's curated references; map the portfolio yourself and investigate how the investor behaved when things went wrong.
I can do the portfolio mapping for you: identify the companies they've backed, trace the relevant partner's previous investments, find the founders, separate successful companies from failures/acquisitions, and build you a VC diligence/reference-check spreadsheet with specific people to contact and questions to ask.
"Do they respect decisions they disagree with?"
"Did they ever use their board seat or investor rights in a way that surprised you?" "Were there any terms you wish you'd negotiated differently?"
Don't ask whether they're "value-add."
Ask:
"What's the most valuable thing they actually did for you?" And:
"Can you give me a specific example?" A claimed network is worthless until someone can point to actual introductions, hires, customers, financing help, recruiting, etc.
This one is particularly important:
"Did they participate in your subsequent rounds?" "If they didn't, why not?" "How did they behave when you needed additional capital?" "Did they help you find the next investor?" A VC that writes the initial check but disappears when you need the next round may not be the partner you think you're getting.
At the end of every call:
"Is there anything about working with this investor that you think I should know but haven't asked about?" Then wait.
And if they give you something vague:
"Can you tell me more about that?" Don't fill the silence.
The objective isn't to collect complaints. It's to identify patterns.
One founder saying "they were occasionally slow on email" means little.
Four founders independently saying:
"They're fantastic until they disagree with you, and then they become extremely controlling." That's a signal.
I'd be particularly cautious about:
Independent references are important precisely because the firm's supplied references are inherently curated.
I'd ask the partner:
Diligencing a venture capital firm is just as critical as the VC diligencing your startup. You are entering into a multi-year marriage, and you need to know how they behave when things go right—and more importantly, when things go wrong. The Best Ways to Diligence a VC Firm - Do not just talk to the cherry-picked…
Diligencing a venture capital firm is just as critical as the VC diligencing your startup. You are entering into a multi-year marriage, and you need to know how they behave when things go right—and more importantly, when things go wrong.
The Best Ways to Diligence a VC Firm
- Do not just talk to the cherry-picked references the VC hands you.
- Find founders from their portfolio whose companies are struggling, pivoted, or shut down entirely. Ask them: *"How did the partner react when you missed your milestone? Did they roll up their sleeves or panic? Were they supportive during the bridge round or did they push you to shut down?"* [](https://www.crv.com/content/reference-check-questions-for-founders) [[1]](https://www.crv.com/content/reference-check-questions-for-founders)
- Ask the VC for data on their fund's reserve ratio. Do they have dry powder to support you in a Series A or B, or are they a one-and-done check who will look dilutive or absent in subsequent rounds?
- Venture capital firms are made of individuals, not monoliths. Figure out which specific partner will actually lead your deal and sit on your board. Have they led deals in your exact sector? Do they have decision-making authority, or do they need consensus from senior partners who know nothing about your space?
- Look out for aggressive or predatory terms—such as participating liquidation preferences, overly restrictive protective provisions, or suffocating founder vesting schedules that aren't market standard.
How to Find Founders They Have Backed Previously
- Check platforms like PitchBook, Crunchbase , or Dealroom to pull the complete investment portfolio of the specific VC firm. Look at the "Portfolio" or "Investments" tab on their company profiles.
- Go directly to the firm's website portfolio page. While some VCs only highlight their "unicorns," many list all current and past investments. Cross-reference those company names on LinkedIn.
- Search for the name of the VC firm in the "Past Experience" or "Current Experience" filters, combined with titles like "Founder," "Co-founder," or "CEO." This will surface founders who might not even be prominently displayed on the VC’s official website.
- Utilize crowd-sourced founder platforms like [OpenVC](https://www.openvc.app/) or community-driven investor feedback databases (such as landscape spreadsheets shared in founder slack channels or Twitter/X threads) where founders openly review investor behavior.[](https://www.openvc.app/) [[1]](https://www.openvc.app/)
If you'd like, let me know:
I can share a tailored list of the exact questions you should ask their backed founders during your reference calls.
Yes. The key is to **diligence the specific partner, not just the VC firm**. A great firm can have a bad partner, and a mediocre firm can contain an exceptional one. The highest-signal diligence is usually: **map the investor's actual portfolio → identify founders independently → talk to a mix of winners, ordinary…
Yes. The key is to diligence the specific partner, not just the VC firm. A great firm can have a bad partner, and a mediocre firm can contain an exceptional one.
The highest-signal diligence is usually: map the investor's actual portfolio → identify founders independently → talk to a mix of winners, ordinary outcomes, and troubled companies → triangulate what you hear. Recent VC diligence guidance similarly recommends combining VC-provided references with independently sourced and difficult-outcome references.
Before looking at the firm broadly, write down:
This matters because partner behavior can vary substantially within the same fund.
Don't just accept the 5–10 "reference founders" the VC gives you.
Start with the firm's portfolio page, then cross-check it against:
"VC name" "founder name" and "partner name" investmentCreate a spreadsheet with:
| Company | Partner | Year | Stage | Outcome | Founder | Founder contact | Your connection |
|---|---|---|---|---|---|---|---|
| Company A | Partner X | 2021 | Seed | Acquired | Jane Doe | 2nd degree | |
| Company B | Partner X | 2022 | Series A | Growing | John Doe | Friend of friend | |
| Company C | Partner X | 2019 | Seed | Shut down | Jane Smith | Cold |
The failed/shut-down companies are particularly valuable. You want to know what the investor is like when things aren't going well—not just when they're sitting on a 20x winner.
This is one of the best tricks.
Look at the partner's entire career history.
Suppose Partner X was previously at Fund A and is now at Fund B. Find the companies Partner X backed at Fund A and contact those founders too.
Those founders aren't necessarily on the current firm's reference list, and they can give you a much less curated view.
Crunchbase explicitly supports searching for investments made by individual partners, including investments they made while acting as a partner at an investment firm.
I'd aim for roughly:
That gives you enough data to see patterns rather than overweighting one person's experience. Recent guidance recommends roughly five to seven conversations with this kind of mix.
And don't make the calls all to unicorn founders.
A founder who sold for $500M may love their VC because everything worked. A founder whose company struggled can tell you much more about:
Avoid:
"Do you like them?" You'll almost always get a polite answer.
Instead ask:
Relationship
Board behavior
Hard moments
Fundraising
Value-add
Don't accept "they're very helpful."
Ask:
"What's the most valuable thing they actually did for you?" Then:
"Can you give me a specific example?" Concrete examples are much more informative than descriptions of a firm's "platform."
And finally ask:
"Is there anything I should have asked you that I haven't?" That often surfaces the thing someone was reluctant to volunteer.
This is where the diligence gets really interesting.
Suppose the VC tells you:
"We're extremely founder-friendly and hands-off." Founder #1 says:
"They're hands-off." Founder #2 says:
"They let me run the company." But Founder #3 says:
"They were extremely involved in hiring." That isn't necessarily a red flag. Maybe the third company had a different situation.
But if multiple independent founders describe the same behavior, believe the pattern.
Also compare what the VC promises you with what happened historically:
| VC says | Check with founders |
|---|---|
| "We support follow-ons" | Did they actually invest in later rounds? |
| "We help with hiring" | Who did they actually recruit? |
| "We're founder-friendly" | What happened during disagreements? |
| "We have a huge network" | Which customer introductions actually happened? |
| "We don't interfere" | How involved were they in operations? |
| "We're here for the long term" | What happened when companies struggled? |
Founder references aren't enough.
Understand:
You are effectively choosing someone who may sit on your board for years, so terms and governance matter almost as much as reputation.
I'd ask every founder:
"If you were starting your company again tomorrow, would you take money from this investor again?" Then stop talking.
Don't rescue them from the silence.
The first reaction—and the explanation afterward—is often more revealing than a 20-minute discussion. This question is also specifically recommended in recent investor-reference guidance.
If you give me the name of the VC firm (and ideally the partner you're dealing with), I can do the research for you.
I can map out:
That is substantially more useful than just looking at the firm's website.
"If you were starting your company again tomorrow, would you take money from this investor again?" Then stop talking.
Don't rescue them from the silence.
The first reaction—and the explanation afterward—is often more revealing than a 20-minute discussion. This question is also specifically recommended in recent investor-reference guidance.
This is where the diligence gets really interesting.
Suppose the VC tells you:
"We're extremely founder-friendly and hands-off." Founder #1 says:
"They're hands-off." Founder #2 says:
"They let me run the company." But Founder #3 says:
"They were extremely involved in hiring." That isn't necessarily a red flag. Maybe the third company had a different situation.
But if multiple independent founders describe the same behavior, believe the pattern.
Also compare what the VC promises you with what happened historically:
| VC says | Check with founders |
|---|---|
| "We support follow-ons" | Did they actually invest in later rounds? |
| "We help with hiring" | Who did they actually recruit? |
| "We're founder-friendly" | What happened during disagreements? |
| "We have a huge network" | Which customer introductions actually happened? |
| "We don't interfere" | How involved were they in operations? |
| "We're here for the long term" | What happened when companies struggled? |
Founder references aren't enough.
Understand:
You are effectively choosing someone who may sit on your board for years, so terms and governance matter almost as much as reputation.
I'd ask every founder:
Diligencing a venture capital firm is just as critical as them diligencing your startup. You are entering a 7-to-10-year marriage, and capital is only as good as the partner wielding it. Part 1: The Best Ways to Diligence a VC Firm 1. **Map the Portfolio Health and Velocity**
Diligencing a venture capital firm is just as critical as them diligencing your startup. You are entering a 7-to-10-year marriage, and capital is only as good as the partner wielding it.
Part 1: The Best Ways to Diligence a VC Firm
Part 2: How to Find Founders They Have Backed Previously
If you'd like, let me know:
I can tailor a specific list of probing questions to ask their partners or help you figure out how to approach their past founders.
Yes. **Diligencing a VC is basically the same exercise as diligencing a major hire:** don't rely on the pitch deck or references they hand you. Reconstruct their actual behavior, then talk to people who experienced it. The highest-signal question is not "Are they good investors?" It's **"Would you take their money…
Yes. Diligencing a VC is basically the same exercise as diligencing a major hire: don't rely on the pitch deck or references they hand you. Reconstruct their actual behavior, then talk to people who experienced it.
The highest-signal question is not "Are they good investors?" It's "Would you take their money again?"
Figure out exactly which partner would own your investment.
Then investigate:
This matters because a firm's website can make a 10-person partnership look like one homogeneous investor. It isn't.
In particular, search the partner's name alongside:
portfolioinvestmentfounderboardleftconflictfounder experienceterm sheetfollow-onacquisitionPartner history is one of the best ways to uncover founders the firm won't put on its reference list. CRV's own recent founder-diligence guide makes essentially this point: following a partner across prior firms surfaces companies—and founders—missing from the current firm's portfolio list.
Don't just copy the firm's "Portfolio" page.
Create a spreadsheet with:
| Company | Partner | Year | Stage | Outcome | Current status | Founder | Your connection |
|---|---|---|---|---|---|---|---|
| Company A | Partner X | 2021 | Seed | Acquired | — | Jane Doe | 2nd degree |
| Company B | Partner X | 2022 | Series A | Alive | Growing | John Doe | Cold |
| Company C | Partner Y | 2019 | Seed | Shut down | — | Sarah Doe | 1st degree |
Then find every company they've ever invested in, including:
For paid research, pitchbook.com is particularly useful because it tracks investor/deal/company relationships and combines public sources with primary research.
You can also use Crunchbase, LinkedIn, company press releases, Google searches, and SEC filings to reconstruct the list.
This is one of my favorite diligence tricks.
Suppose the firm's website says:
"We've backed 35 companies." You discover 50 companies associated with the firm/partners.
Ask:
Why aren't the other 15 on the website?
Some perfectly legitimate reasons exist—failed companies, old investments, portfolio strategy changes, etc. But you want to understand the selection bias.
The companies they don't showcase can be more informative than the ones they do.
There are several ways.
For each portfolio company:
Don't ask:
"Is VC X a good investor?" Ask something much more specific:
"I'm considering taking money from VC X and would love to hear what it was actually like working with them—particularly around board dynamics, follow-on financing, and what happened when things got difficult." That gets you much better information.
Try combinations like:
"Company Name" "VC Name""Founder Name" "VC Name""Partner Name" founder"Partner Name" "Company Name""VC Name" "board""VC Name" "follow-on""VC Name" "term sheet"You can often uncover interviews, podcasts, conference talks, acquisition announcements and old portfolio pages this way.
Ask other founders:
"Who do you know who has taken money from X?" Then keep following the chain.
One warm intro to a founder is worth substantially more than 20 LinkedIn reviews.
Don't just talk to the successful ones.
I'd deliberately get:
The failures are often the highest-signal references.
Ask the same questions to everyone.
Relationship
Board behavior
Follow-on
Bad times
Hiring
Exit
And then ask the most revealing question:
"If you were starting the company again tomorrow, knowing everything you know now, would you take their money again?" Then stop talking.
The hesitation is information.
This is even better:
"What's the thing about them that you wish you'd known before taking their money?" Or:
"What is their biggest weakness as an investor?" You're looking for specific behavioral patterns, not generic complaints.
"Sometimes they're busy" = probably irrelevant.
"They stopped answering my calls when we missed our revenue target" = extremely relevant.
"They pushed our CEO out after two bad quarters" = extremely relevant.
This is an underrated part of VC diligence.
Look at the firm's existing portfolio and ask:
You should ask the partner directly:
"What information about my company would you consider confidential, and what circumstances could lead you to invest in a competitor?" You should also ask for their conflict policy if appropriate.
For registered advisers, Form ADV is worth checking. The SEC's IAPD database provides registration information, business practices, conflicts, disciplinary history and other disclosures.
Not every VC will have the same regulatory footprint—many operate under venture-capital/exempt-reporting structures—so don't interpret absence of a particular filing as a red flag by itself.
Ask the partner:
This tells you whether you are actually important to them.
A $500M fund writing a $1M check to you may have a very different incentive structure from a $50M fund writing a $5M check.
I'd want to understand:
Fund size → check size → ownership → reserve strategy → portfolio construction → your expected importance.
A useful question is:
"What would have to happen for you to consider this investment a failure?" Then:
"What percentage of your portfolio companies do you expect to become meaningful winners?" You don't need them to predict your outcome. You're trying to understand whether their economics make sense for your company.
This is one of the strongest historical indicators.
If the firm has been around long enough, investigate what it did during:
For companies that hit trouble:
A VC's behavior when a company is winning tells you surprisingly little.
Their behavior when the company is losing tells you almost everything.
If you're currently evaluating a specific VC, I'd do this:
First 30 minutes
Next 30 minutes
For each company, find:
Next 30 minutes
Find 5–10 founders you can potentially contact.
Prioritize:
Final 30 minutes
Conduct 2–3 calls and ask the same questions every time.
Then compare what founders told you against what the VC told you.
I'd take these seriously:
And one particularly important signal:
If every founder you speak with says the VC is "great" but nobody can give you a concrete example of how the VC helped, that's not necessarily a good sign.
The best references usually sound something like: "They did X during our Series B, Y when we had a CEO problem, and Z when we were nearly out of cash."
That's evidence.
If you give me the name of the VC firm and the partner you're talking to, I can do the first-pass diligence for you: reconstruct their portfolio, identify the partner's prior investments, find founders you could potentially contact, and flag the companies/outcomes I'd investigate most closely.
If you're currently evaluating a specific VC, I'd do this:
First 30 minutes
Next 30 minutes
For each company, find:
Next 30 minutes
Find 5–10 founders you can potentially contact.
Prioritize:
Final 30 minutes
Conduct 2–3 calls and ask the same questions every time.
Then compare what founders told you against what the VC told you.
I'd take these seriously:
And one particularly important signal:
If every founder you speak with says the VC is "great" but nobody can give you a concrete example of how the VC helped, that's not necessarily a good sign.
The best references usually sound something like: "They did X during our Series B, Y when we had a CEO problem, and Z when we were nearly out of cash."
That's evidence.
If you give me the name of the VC firm and the partner you're talking to, I can do the first-pass diligence for you: reconstruct their portfolio, identify the partner's prior investments, find founders you could potentially contact, and flag the companies/outcomes I'd investigate most closely.
Conducting "reverse diligence" on a venture capital firm is just as important as the diligence they perform on you . A term sheet is the beginning of a multi-year marriage, and you need to know how a partner and their fund behave when things go sideways—not just when they…
Conducting "reverse diligence" on a venture capital firm is just as important as the diligence they perform on you . A term sheet is the beginning of a multi-year marriage, and you need to know how a partner and their fund behave when things go sideways—not just when they win.
Part 1: How to Diligence a VC Firm
To thoroughly vet a VC firm, look across four core dimensions: fund mechanics, portfolio track record, partner reputation, and value-add dynamics.
Part 2: How to Find Founders They Have Backed Previously
Backchannel reference checks with founders who have taken money from the firm are your highest-signal tool.
If you'd like, let me know:
I can share a more tailored set of questions to ask their portfolio founders during your backchannel calls.
Yes. **You should diligence a VC almost like you would diligence a senior hire who is going to sit on your board for 5–10 years.** The biggest mistake is evaluating the firm's brand rather than the *specific partner who will own your deal*. The highest-signal diligence is talking to founders the VC **didn't choose for…
Yes. You should diligence a VC almost like you would diligence a senior hire who is going to sit on your board for 5–10 years. The biggest mistake is evaluating the firm's brand rather than the specific partner who will own your deal.
The highest-signal diligence is talking to founders the VC didn't choose for you.
I’d break it into six areas:
| Area | What you're trying to learn |
|---|---|
| Partner | How they behave when things go badly; responsiveness; judgment; board behavior |
| Firm | Reputation, fundraising health, conflicts, decision-making |
| Portfolio | Relevant companies, concentration, competitive conflicts |
| Follow-on | Whether they actually support companies through difficult rounds |
| Value-add | Specific introductions/recruiting/product help—not generic "platform" claims |
| Terms & control | Board seat, pro rata, protective provisions, information rights, founder-unfriendly clauses |
For the regulatory/background piece, you can search the firm's SEC Investment Adviser Public Disclosure (IAPD) record and Form ADV. Those filings can reveal ownership, business practices, affiliations, fees/conflicts and disciplinary disclosures.
But founder references are where I'd spend most of the time.
Don't just ask:
"Can you give me three founder references?"
Do that, but assume those will be the firm's best references.
Instead, construct the list independently.
Go to the firm's portfolio page and copy every company, not just the logos they prominently feature.
Then for each company find:
Crunchbase is particularly useful here because its portfolio-company data can connect an investor to companies, funding rounds and founders.
Then use LinkedIn and your own network to get to the founders.
The key is to map the partner, not merely the firm.
If Partner A is giving you the term sheet, you care much more about the companies Partner A personally worked with than whether another partner at the firm backed a unicorn.
This is probably the single most important trick.
Don't only find:
Find:
A founder whose company failed can tell you something a successful founder often can't:
"What did this investor do when things got really ugly?"
That is exactly when you'll discover whether the VC is a partner or a problem.
Several current VC diligence guides recommend explicitly asking for references from companies that struggled or failed and then independently finding additional references.
Suppose you're diligencing XYZ Ventures and Partner Jane Smith.
I'd do this:
Step 1 — Portfolio
Search:
"XYZ Ventures" portfolio
and their website.
Make a spreadsheet of every company.
Step 2 — Funding databases
Search XYZ Ventures on Crunchbase and similar databases to identify companies that don't appear on the firm's current website.
Step 3 — Partner history
Search Jane Smith's LinkedIn/profile and previous firms.
This is important. If she previously worked at ABC Capital, look at ABC's historical portfolio too.
You can uncover founders she backed 5–10 years ago who aren't associated with her current firm's marketing materials.
Step 4 — Founder identification
For each company:
[company] founder
[company] CEO
[company] Jane Smith
LinkedIn is usually enough to establish the relationship.
Step 5 — Find warm paths
Look through:
A warm intro is ideal.
Step 6 — Cold outreach if necessary
You don't need a complicated story. Something like:
"I'm considering taking investment from [Partner] at [Firm]. I noticed you worked with them at [Company]. Would you be willing to spend 15 minutes sharing what the relationship was actually like?"
Founders generally understand why you're doing it.
Don't ask:
"Was XYZ a good investor?"
You'll get:
"Yeah, they were great."
Instead ask questions where they have to recall actual behavior.
1. "Would you take money from this partner again?"
Then stop talking.
This is probably the best single question. The hesitation, qualification and enthusiasm are often more informative than the eventual answer.
2. "What happened the first time you missed your plan?"
You're looking for behavior under pressure.
3. "Tell me about a disagreement you had with them."
Not whether they disagreed—the interesting question is how the disagreement was handled.
4. "How did they behave when you needed more money?"
This gets at follow-on behavior and whether they become difficult when the company isn't performing.
5. "How involved were they after the investment?"
Distinguish:
6. "What did they promise during the fundraising process that turned out not to be true?"
Extremely high signal.
7. "What is their biggest weakness as an investor?"
If the founder can't identify one, you may be talking to a curated reference.
8. "How are they in a board meeting when things are going badly?"
Very important if they'll have a board seat.
9. "Did they ever surprise you—in a good or bad way?"
This often produces stories rather than canned answers.
10. "Is there anything I should know before taking their money that I haven't asked?"
Then be quiet.
That "but" is usually the interesting part.
Not necessarily bad—but insufficient.
That's much more concerning.
Current VC diligence guidance specifically recommends asking for references beyond the firm's curated list and including companies where things didn't go well.
Ask:
"What is the most valuable thing they actually did for you?"
You want answers like:
"They got us our first Fortune 500 customer."
not:
"Their platform team is incredible."
This is a common thing to test explicitly. Ask how responsive the partner was six months after the investment, not immediately after signing.
Again, you are choosing a person, not a logo.
This is underrated.
Find founders who have raised subsequent rounds and ask:
"When you raised your Series B, how did [VC] behave?"
And, if appropriate, ask another investor:
"What's the reputation of [Partner] among other VCs?"
Other investors can tell you things founders may not know:
Don't let the excitement of getting a term sheet overwhelm your judgment.
Score each category 1–5:
Partner
Firm
Founder references
Economics/control
And record actual quotes/examples, rather than just "4/5."
If I were doing this myself, I'd aim for 8–10 founder conversations:
That gives you a much more representative sample than three glowing references.
And I'd do this before signing the term sheet if possible, but definitely before the financing is finalized.
If you give me the name of the VC firm (and ideally the partner who's leading your deal), I can actually do the next step with you: map their portfolio, identify the founders they've backed, separate the partner's investments from the firm's, and help you build a back-channel reference list.
Diligentia on a Venture Capital (VC) firm is just as important as the diligence they do on you. You are entering a 10-year partnership, so you need to look past the branding and evaluate their actual track record, value-add, and…
Diligentia on a Venture Capital (VC) firm is just as important as the diligence they do on you. You are entering a 10-year partnership, so you need to look past the branding and evaluate their actual track record, value-add, and reputation.
How to Diligence a VC Firm
How to Find Founders They Have Backed Previously
If you'd like, let me know:
I can give you a tailored list of specific red flags to look out for during your conversations.
Diligencing a venture capital firm is essentially **interviewing a boss you cannot easily fire** ; because VC money is virtually un-refundable, conducting comprehensive "reverse due diligence" is a mandatory step before signing any term…
Diligencing a venture capital firm is essentially interviewing a boss you cannot easily fire ; because VC money is virtually un-refundable, conducting comprehensive "reverse due diligence" is a mandatory step before signing any term sheet.
The absolute best way to diligence a VC is to speak directly with founders they have previously backed, specifically focusing on "off-list" references from failed or struggling portfolio companies.
🔎 How to Find Founders They Have Backed
When a VC offers you references, they will provide a curated list of their absolute biggest success stories. To get the truth, you must bypass this list and find "back-channel" or off-list references.
"[VC Firm Name]" + "seed" or "Series A" . This often reveals early-stage investments that failed later on and were quietly scrubbed from the active portfolio website.📋 The Reverse Due Diligence Framework
To thoroughly vet a VC, evaluate them across four distinct pillars.
Do not just call the winners. You need to hear how the VC behaves when things go horribly wrong. Aim for 4–5 total conversations : 2 from their approved list, and 2–3 via your own back-channels.
Understand the firm's structural health to ensure they can support your future rounds.
💬 Key Questions to Ask Portfolio Founders
When you get a past founder on the phone, use these precise prompts to cut through polite corporate filters:
If you'd like to narrow this down, let me know:
I can give you specific notes on their reputation or help draft a tailored reference-checking email.
Yes. **Diligencing a VC is a lot like diligencing a potential cofounder**: don't just evaluate their brand and stated thesis—talk to the people who have actually worked with them. The most useful question is not “Is this a good VC?” but **“What will this particular partner be like when things go well, and when things…
Yes. Diligencing a VC is a lot like diligencing a potential cofounder: don't just evaluate their brand and stated thesis—talk to the people who have actually worked with them.
The most useful question is not “Is this a good VC?” but “What will this particular partner be like when things go well, and when things go badly?”
If you're considering taking money from a VC, identify the actual partner who would own the relationship.
Research:
This matters because a firm's brand can be excellent while your individual partner is mediocre, or vice versa. PitchBook specifically recommends looking at the deals individual fund managers have led, their co-investors, and the firm's investment history when evaluating an investor.
Start with the firm's own portfolio page. Many firms explicitly list their companies and sometimes the founders.
For example, some firms provide unusually good information: Founders Fund's portfolio lists its portfolio companies, while LOI VC's portfolio actually names the founders alongside the companies.
Then cross-check it against independent databases. PitchBook is particularly useful for reconstructing investment history; other databases such as Crunchbase, Dealroom, and VCBacked can help fill gaps. For example, VCBacked maintains investor → portfolio-company mappings and founder information.
I'd build a spreadsheet with:
| Company | Founder | VC Partner | Entry Stage | Led? | Follow-on? | Outcome | Founder sentiment |
|---|---|---|---|---|---|---|---|
| Company A | Jane Doe | Partner X | Seed | Yes | Yes | Acquired | ? |
| Company B | John Smith | Partner X | Series A | No | No | Active | ? |
| Company C | Sarah Lee | Partner Y | Seed | Yes | Yes | Failed | ? |
The failed companies are particularly important. Don't only talk to the winners.
There are several increasingly effective ways to do this.
A. LinkedIn
Search:
"Company Name" founder LinkedIn
Then:
"VC Firm" "Company Name"
You can usually identify the founder and the partner who announced the investment.
B. Google
Search combinations like:
"VC Firm" "portfolio" founder
"Partner Name" "Company Name"
"VC Firm" "Founder Name"
"VC Firm" "former portfolio"
Investment announcements are particularly valuable because they often identify the partner responsible for the deal.
C. The VC's own website
Some firms explicitly structure their portfolio around founders. Flex Capital, for example, has a searchable portfolio of 241 companies and identifies when it partnered with each company.
D. Database tools
If you're doing serious diligence, PitchBook is probably the most comprehensive paid option. Crunchbase is useful for funding history and relationships, while specialized databases can make the investor → company → founder mapping easier.
You'll get polite answers.
Instead, ask questions that force specificity.
I'd ask 5–10 founders individually:
Relationship
Fundraising
Hard times
Governance
Fundraising dynamics
Founder relationship
That last question is particularly powerful.
Don't just interview the VC's showcase companies.
I'd deliberately find:
Also try to find someone who declined their investment. That's a different and very useful perspective.
And if possible, find a founder who had a disagreement or conflict with the partner. That's often more informative than five glowing references.
VC websites are marketing material. Their current portfolio isn't necessarily their complete historical portfolio.
Look for:
A database can help here. For example, Seedtable's investor records can distinguish companies where a fund led rounds, followed on, and exited, which is much more informative than simply looking at a logo wall.
I'd score them on:
Partner
Capital
Network
Governance
Reputation
Fit
Ask the VC:
“Can you give me the names of 3–5 founders I should talk to, including one company that didn't work out?”
Their reaction is data.
If they enthusiastically give you a struggling founder, that's a good sign. If you only receive carefully curated unicorn CEOs, do your own reference checking.
And when you contact founders yourself, don't say “I'm considering taking money from them—what do you think?” A better approach is:
“I'm considering working with [Partner]. I'd really value 15 minutes on what it's actually like to have them as an investor.”
You'll generally get much more candid information.
If you give me the name of the VC firm (and ideally the partner you're talking to), I can do the research with you: map their historical portfolio, identify the founders, distinguish winners/failed companies, find likely founder contacts, and build a VC diligence scorecard specifically for that firm.
