Aug 14, 2020 · 42m · 20vc
20VC: Why Few Firms Are Doing True Early Stage Investing Today, Why Founders Should Spend Time with Analysts When Raising & The Rise of Pre-Empting Rounds and How To Know When To Engage vs Wait with Anna Khan, General Partner @ CRV
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In this episode of The 20 Minute VC, host Harry Stebbings speaks with Anna Kahn, General Partner at CRV, about her path into venture capital, early-stage investment conviction, deal sourcing strategies, and actionable solutions for closing the gender diversity gap in venture capital.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 34% of the talking time here. How this is scored →
Harry as informed peer 3.4 Guest teaching 4.6 Guest disagreement 2.7 Harry pushing back 2.5
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 26:15 Anna destroys the 'pipeline problem' argument
When Harry brings up the common industry narrative that a lack of female partners stems from a pipeline problem, Anna forcefully rejects the premise, calling it a lazy crutch and explaining that technical degrees are not required for VC success.
Hardest push from Harry ▶ 24:17 Harry challenges early-stage fund alignment vs multi-stage fundsHarry actively pushes back against Anna's thesis that founders are always better off taking dedicated early-stage capital, offering a price-optimization framework and pointing out that multi-stage firms are winning market share at seed.
Biggest teaching moment ▶ 8:55 Anna corrects Harry and Paul Graham on analyst importanceWhen Harry aligns with Paul Graham's stance against meeting analysts, Anna educates him on board dynamics, showing how partner bandwidth limitations make analysts a founder's most vital internal champion.
Harry holds his own ▶ 33:00 Harry demonstrates his empathy-first investing philosophyHarry demonstrates his high-EQ investment strategy by detailing a deal where he evaluated the founder's wisdom and resilience through personal trauma rather than needing product specs or financial metrics.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome and Opening Remarks with Anna Kahn | 1 | 2 | 0 | 0 | Harry welcomes Anna Khan and asks standard setup questions about her background. Anna outlines her path from finance to startups and venture, prompting a friendly joke from Harry about startups and finance having a baby. | |
| Growing Up in Pakistan and Moving to the US | 1 | 4 | 1 | 1 | Harry asks Anna about growing up in a 21-person household in Pakistan and moving to the US alone at 17. Anna provides perspective on living through a military coup and political turbulence, which instilled resilience and grounded her career drive. | |
| The Critical Role of Analysts in Venture Capital | 4 | 6 | 5 | 5 | Harry cites Paul Graham's advice that founders should only talk to partners in VC firms and agrees with it. Anna firmly pushes back, reframing analysts as a founder's fiercest internal advocate because busy partners rely heavily on junior talent. | |
| Key Lessons Learned at Bessemer Venture Partners | 2 | 4 | 1 | 1 | Harry asks about Anna's foundational takeaways from her years at Bessemer. Anna outlines three core lessons regarding sourcing, first impressions, and evaluating founder character by how they treat junior team members. | |
| Effective Sourcing Strategies and Differentiation | 3 | 5 | 4 | 2 | Harry probes Anna on sourcing methods and network building. Anna presents a contrarian view that VC networking happy hours are counterproductive, advocating instead for deep engagement with small peer groups and technical leaders. | |
| Evolving Investment Decision-Making and Conviction | 3 | 4 | 1 | 2 | Harry asks how Anna competes as a younger GP against legacy venture heavyweights like Marc Andreessen and Peter Thiel. Anna shares tactical approaches, such as out-investing time and bringing sector-specific depth rather than general status. | |
| Market Compression and Pre-Empting Rounds | 6 | 6 | 4 | 6 | Harry challenges Anna's thesis on pure early-stage funds, noting that multi-stage funds frequently win seed deals. Anna defends focused early-stage funds, arguing they build stronger founder alignment without applying generic playbooks. | |
| Addressing Gender Diversity and the Pipeline Fallacy in VC | 5 | 7 | 7 | 4 | Harry brings up the argument that the scarcity of female partners is a pipeline problem. Anna forcefully rejects the premise as a lazy crutch and highlights how promotion standards differ between men and women in VC. | |
| Actionable Steps for Increasing Diversity and Female Representation | 4 | 6 | 3 | 3 | Harry asks for actionable solutions for male-dominated partnerships to improve diversity. Anna outlines educational initiatives like LaunchX, hiring female junior investors, and emphasizes that true commitment requires sharing GP carry. | |
| Media Role Models and Evaluating the Human Element in Founders | 5 | 3 | 1 | 1 | Harry points out that Anna's role models are media figures like Oprah and Christiane Amanpour. Anna explains how their interviewing style gets to human core truths, prompting Harry to share an anecdote about investing based on emotional wisdom over metrics. | |
| Quick Fire Round with Anna Kahn | 3 | 4 | 3 | 2 | In the quickfire round, Anna offers strong opinions, arguing that operators often make poor VCs because they try to act like second CEOs in the boardroom. Harry engages with brisk follow-up questions across multiple topics. |
Statements from this episode (23)
Anna Khan: Every Stanford Senior Today Knows What Venture Capital Is
“Today, every senior at Stanford knows what a VC is, but back then it wasn't really an industry that was accessible to young people.”
Anna Khan: Top VC Deals Rely on Junior Analysts Pounding the Table
“And in my kind of seven to eight years in venture, some of our best deals would have never gotten done had an analyst not pounded the table and made the argument on behalf of the entrepreneur.”
Anna Khan: Founders Should Test Junior VCs by Asking for Work
“What I always tell my founders is, you should reply, and then you should get them to do work for you. It's very easy to send an email to an entrepreneur, but when they reply, you And they ask you to do something. I think that's when you can really shine both a…”
Anna Khan: Sourcing Founders Early Remains the Core of VC Success
“The first is never forget that sourcing is still the heart of venture investing. Getting to a founder and Earlier than anyone else is how you succeed, and a lot of partners forget that because once you reach that level, you sort of think sourcing is below you,…”
Anna Khan: Respecting Junior VC Analysts Signals Future Founder Success
“If I look back at all the outbound emails that I sent when I started, and the founders that responded to me, and the way in which they responded to me, the ones that ended up being very successful, they responded honestly, they were transparent with their numb…”
Anna Khan: VC Networking Is Antithetical to Good Deal Sourcing
“Hanging out with other VCs as fun as it is, is It's antithetical to good sourcing. If we're very honest, the only deals you pass on to other VCs are deals that you don't want to do, especially if you're collaborating with firms that invest at the same stage.”
Anna Khan: Spending Time With Product Leaders Beats Networking With VCs
“Hanging out with product or engineering leaders is time much better spent because they're actually using the products that you want to invest in.”
Anna Khan: Publishing Thesis-Driven Articles Drives Significant Inbound Founder Deal Flow
“Blogging has been really helpful for me. It really helped me get my voice out there. I wrote about The things I wanted to invest in, whether it was open source or finance as a service. And I have founders email me a tremendous amount saying things like, I'm ac…”
Anna Khan: Early-Stage VC Requires Leaps of Faith Over Financial Metrics
“Earlier in my career, I was much more data-driven, but I think what's really evolved over this time is my ability to take a leap of faith based on early signs, whether that's chatter about a product, whether it's a founder that spent time in the industry that …”
Anna Khan: Younger VCs Win Competitive Rounds by Out-Investing Time
“Spending more time with the entrepreneur is one of the main ways, because as I mentioned in sort of our analyst conversation, partners are really busy and they have made a commitment to 10, 12, sometimes 15 other entrepreneurs that they have long-term relation…”
Anna Khan: Deep Sector Domain Experience Trumps Generalist VC Longevity
“I think the last thing that has really worked for me is just always showing up with more information and saying, I may have only eight years of venture experience, but I know your space so well. I have deep sector experience. And in a lot of ways, I think that…”
Anna Khan: Top Founders Are Skipping Formal Fundraising Processes Post-COVID
“Especially now after COVID, the supply of good companies has decreased, and the best companies frankly aren't going through a formal fundraising process”
Anna Khan: Early-Stage VCs Should Stretch on Valuation for Proven Markets
“If you spend time on a market and see strong precedent there for meaningful exits, I wouldn't wait. I would stretch on valuation, make it a deal that is hard for the entrepreneur to say no to, especially at the early stage, because the more late stage you go, …”
Anna Khan: Early-Stage VCs Build Deeper Founder Bonds Than Multi-Stage Firms
“It's really hard to forget the person that bet on you when no one knew your name or used your product, and I think that is sort of that secret weapon that early stage funds can use because they come out of it with a much deeper and much more emotional connecti…”
Anna Khan: Multi-Stage VC Funds Apply Generic Playbooks to Early-Stage Startups
“I think multi-stage funds kind of slap on playbooks. They're not very customized, and it's hard to launch with those kind of plain vanilla playbooks.”
Harry Stebbings: Multi-Stage Seed Investors Lack Incentive to Drive Up Series A
“If you take in a multi-stage fund at seed, they are not incented to price you up at the A because they're already in and they've got their ownership.”
Anna Khan: The VC Gender Gap Is Not a Pipeline Problem
“I think pipeline is a lazy crutch. I think the reality is it's only a pipeline problem if you believe the best VCs have to be technical, which if you look at the Midas list is not the case at all.”
Anna Khan: Women in VC Are Promoted for Results, Men for Potential
“Women still get promoted for results while men get promoted for potential, and that's what we need to change.”
Anna Khan: Hiring Female Junior Investors Expands Deal Flow to Women
“Hire great female analysts and associates. You, after hiring them, will realize that you will see more female CEOs pitch you, because through hiring these analysts, you are getting access to networks that you just have no access to.”
Anna Khan: Sharing Carry Is the Most Meaningful Validation for Women
“When you hire a female GP, you're telling the rest of the world, I believe in this woman's work so much that I am willing to give more share of my dollars in my pocket to her, and more than that, I believe she is going to bring so much more to this GP pie that…”
Anna Khan: VC Pitching Has Become Overly Commoditized Around Software Metrics
“Unfortunately, I see that less and less in venture, because I think it's become So commoditized, where within five minutes, we're asking about the ARR, and the net dollar retention, and the growth rate, and few people really take time to ask the questions like…”
Anna Khan: Former Operators and CEOs Do Not Make Good Venture Capitalists
“That operators don't make good VCs. That's what I believe. I think it's really tough to have two CEOs in the boardroom. I think CEOs, when things work well for them, they're so used to repeating that, and sometimes it can work for another founder, but it's oft…”
Bessemer Created the Original Metrics for Evaluating Cloud Software Growth
“At Bessemer, we were the ones that came up with metrics on how to measure great cloud companies when no one knew how to measure cloud growth, and so as a result, we gravitated a lot more to that than really focusing on kind of team or the early signs in the ma…”