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By Larry Chiang 

author of What They Don’t Teach You at Stanford Business School, former Stanford EIR, and frequent writer on street-smart entrepreneurship) 

I have written and spoken extensively about getting venture capitalists to mentor you, even ones you don’t know. My core idea is that mentorship is often more valuable (and more accessible) than immediately asking for money; advice and relationships can open the door to funding later. quora.com 

Key articles and sources include my 2010 GigaOM piece “How to Charm a VC Into Mentoring You,” a related VentureBeat column on getting industry leaders/VCs you don’t know to mentor you, detailed Quora answers on networking with VCs, and material tied to my books chapter 5 (especially chapters on networking ch4 and mentorship). The original GigaOM page is no longer live, but the advice is consistent

Core principles from Chiang

•  Ask for advice or mentorship first, not money. As Dave McClure (500 Startups) advised on a panel Larry Chiang moderated: if you want a VC to consider funding you, start by asking for mentorship. quora.com 

•  VCs have valuable networks and pattern-recognition skills beyond capital. Getting them to open their “rolodex” or give advice is a win even without a check.

•  Use “accelerated networking,” short high-leverage interactions, research, and follow-through. Chiang draws from Mark McCormack (What They Don’t Teach You at Harvard Business School) and emphasizes street-smart execution over formal pitches.

Practical tips he outlines

Here are the main tactics compiled from his Quora answer and related VentureBeat pieces:

1.  Don’t start with “coffee.”
A coffee often signals a long (90-minute+) commitment. Prefer a short 5–10 minute phone call or a brief in-person interaction. Ambush them at parties, conferences, panels, or events: combine a tight elevator pitch with charm and solicit a next step whose goal is mentorship. quora.com 

2.  Use the “transitive property of influence.”
Pre-network by charming a CEO of one of the VC’s portfolio companies and securing an introduction. Charm once and transitively transfer that goodwill to the VC. quora.com 

3.  Woo through deep research.
Thoroughly read about them (bios, writings, investments, public statements). The more genuine common ground or informed context you bring, the better. Chiang compares this to a Vulcan mind meld—know them well before you approach.

4.  Lead with insights and specific value.
Share what trends you’re seeing, your take on recent news, other companies or approaches you like in the space, and the specific industry problems you’re solving. This educates them about your domain while signaling you’re thoughtful. quora.com 

5.  Be specific, not generic.
“Pick your brain” or “be my mentor” is a turn-off. Ask for concrete help on a defined issue. Get in late to conversations and get out early—this signals you execute and respect time. At events where they speak, try for a short walk to/from the car (often ~12 high-value minutes).

6.  Flattery and ego management (use carefully).
Chiang notes tactical compliments grounded in research can help (he gives examples of strongly worded praise of their intellect or work). Document interactions, blog or write about useful advice (which also feeds their ego and creates a record), and follow up meticulously—take action on advice and confirm any verbal offers quickly.

7.  Other supporting moves.
Target events where they appear, recommend them as speakers to conference organizers (after a positive interaction), acquire contact info smartly, use clear subject lines, and prepare by role-playing interactions so you can anticipate their advice. Thank-you notes or small gestures reinforce the relationship. Many mentors help for free; reciprocity (thanks, updates, public recognition) matters.

Chiang also discusses related ideas such as “mentor ledge” (quasi-cold outreach for one or two quick live questions), mentoring the VC on industry problems while positioning your solution, and building momentum through documented follow-up.

Related resources

•  His book What They Don’t Teach You at Stanford Business School (and related site/content) covers networking with VCs and mentorship in depth.

•  VentureBeat pieces by him on getting unknown industry leaders and VCs to mentor you.

•  Quora answers on best forms of networking with VCs and angels.

•  Occasional YouTube clips (including ones titled around the VentureBeat advice).

These tactics are classic Chiang: opportunistic, research-heavy, focused on short high-signal interactions, and oriented toward turning advice into ongoing relationships (and eventually capital or introductions). Success still depends on having something real to discuss—traction, a clear problem, or genuine insights—so the mentorship feels productive rather than one-sided.​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​