Apr 25, 2022 · 36m · 20vc
20VC: Why You Should Think Twice Before Taking Multi-Stage Money at Seed, Why Venture Has Never Been Less Collaborative, How Becoming a Parent Made Me a Better Investor and Why We Should Be Optimistic About the Future of Diversity in Venture with Deena Sh
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Host Harry Stebbings interviews Dina Shakir, Partner at Lux Capital, discussing her non-linear path into venture capital, strategies for navigating high-stakes deal competition, the risks of multi-stage seed investments, and how parenthood and diversity enrich decision-making in tech.
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 37.2% of the talking time here. How this is scored →
Harry as informed peer 4.1 Guest teaching 4.6 Guest disagreement 2.7 Harry pushing back 3.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 19:56 Rejecting gendered interview tropes
When Harry asks how she juggles career and family, Deena immediately confronts the host, asking if he poses the exact same question to working fathers on his show.
Hardest push from Harry ▶ 25:34 Challenging diversity optimism with statsHarry bluntly pushes back against Deena's optimism regarding diversity in venture, stating 'Respectfully, the numbers look shit. Why are you positive?' and citing the 2 percent female founder figure.
Biggest teaching moment ▶ 21:56 Translating toddler negotiations to venture dealsDeena educates Harry on high-stakes negotiation psychology by drawing direct parallels between calm toddler conflict resolution and managing intense board level business negotiations.
Harry holds his own ▶ 17:36 Calling out predatory optionality checksHarry forcefully articulates industry mechanics around multi-stage funds writing small 200k checks in seed rounds just to buy party tickets and optionality at the expense of founders.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Welcoming Dina Shakir and Reflecting on High Interview References | 3 | 3 | 1 | 1 | Harry warmly welcomes Deena, referencing top-tier feedback from past interviewees, and asks about her unique entry into venture. Deena shares her background as an immigrant child from Iraq, Harvard student, journalist, state department fellow, and Googler before venture. The tone is highly collaborative and banter-filled. | |
| Bringing Authenticity to Investing and Handling Preemptive Funding Rounds | 6 | 4 | 2 | 4 | Harry demonstrates deep industry knowledge when criticizing large funds writing small 200k checks to buy optionality, calling it predatory. Deena agrees with his critique and explains how she advises founders when dealing with preemptive rounds and signaling risks. | |
| Dina's Competitive Edge, Creative Founder Outreach, and Brand Building | 5 | 4 | 2 | 2 | Harry asks Deena about her competitiveness and proposes that brand is a hack for track record in early days. Deena shares stories of creative founder outreach like sending a tiger piggy bank and recounts losing a deal early on that pushed her to build a public brand. | |
| Managing Deal Competition, Online Harassment, and Social Media Noise | 3 | 5 | 3 | 3 | Harry asks Deena why Marc Andreessen blocked her on Twitter and asks about coping with online trolls. Deena candidly describes extreme online harassment and rape threats, acknowledging that despite a tough exterior, personal insults still hurt. | |
| How Becoming a Parent Enhances Investment Strategy and Negotiation Skills | 4 | 7 | 6 | 5 | Harry deliberately asks Deena how she juggles work and parenting, prompting Deena to forcefully reject the premise of the question and ask if he asks fathers the same. She then educates Harry on how parenting skills, like toddler negotiation tactics and ruthless time management, make her a much sharper investor. | |
| Optimism for Diversity and Female Founders in Venture Capital | 5 | 6 | 4 | 6 | Harry challenges Deena's optimism regarding diversity in tech by citing dismal statistics around female founder funding. Deena acknowledges the 2 percent stat but reframes the topic by sharing positive trends in overall capital, competitive multi-term sheet deals for female founders, and a poignant story about her daughter. | |
| Quick Fire Questions, Personal Growth, and Doubling Down on Moss | 3 | 3 | 1 | 1 | In a quick-fire round, Deena discusses her favorite book, changing her mind on rest, writing a children's book on entrepreneurship, her mentor Maha Ibrahim, and doubling down on Moss. The segment is lighthearted, respectful, and highly agreeable. |
Statements from this episode (14)
Shakir advises against attending graduate school immediately after undergrad
“Straight to grad school, which I really do not recommend, by the way”
Shakir: 47% of Harvard's 2007 class entered banking or consulting
“At the time, literally 47% of the class before mine went into investment banking or consulting.”
Shakir: Fast VC investment decisions prevent founders from understanding investor dynamics
“The fact that these decisions can be made so quickly without any real insight into what that dynamic is like with the investor, I think is really problematic.”
Stebbings: Venture capital is less collaborative than ever before
“I think venture's less collaborative than ever before.”
Shakir: Multi-stage funds writing small checks won't prioritize early-stage founders
“If they're just barely giving you a couple 100,000 dollars, they're not going to have time. They're just not going to give a shit. It's not going to be a priority for them.”
Shakir: Multi-stage investors skipping follow-on rounds creates major signaling risks
“It's going to look badly if they were in your prior round and don't do the next round. That ends up being a flag in a lot of cases.”
Stebbings: Personal brand is a temporary substitute for early VC track record
“Brand is a hack to track, and what I mean by that is when you don't have track, you gotta have something, and brand is that shop sign that is a replacement for track in the early days.”
Shakir: Building a public VC brand led to severe online harassment
“I've gotten, like, rape threats. I've gotten some weirdo DMing me that he's gonna come eat my pets. I don't even have pets.”
Shakir recommends a popular parenting book as an essential founder leadership guide
“And one of the best books I love to have founders read about leadership is not a business book, but a book called How to Talk So Your Kids Will Listen and Listen So Your Kids Will Talk.”
Shakir: Resolve high-stakes business conflicts using parenting de-escalation tactics
“What it takes is to get them into a small space, a quiet room, literally put yourself, sit down, put your face at their level, hear them. So instead of trying to convince them, stop crying. Why are you crying? This is irrational. I hear you. I know that really…”
Shakir: VC funding for all-female founding teams dropped to 2%
“In terms of the percentage of dollars deployed to solo female founders or women-only founding teams, it's dropped down to two percent, the lowest number since 2016.”
Shakir: Mixed-gender co-founding teams received 15.6% of 2021 venture funding
“I think 15.6% in 2021. They're founding teams that had a woman, but also a male co-founder.”
Shakir: Aspiring VCs should pitch specific deals instead of asking to network
“So rather than asking for someone's time, for the love of God, please don't ask me to freaking pick my brain, which reminds me of the COVID test stick going up. I mean, that is like the worst words you can hear. Tell me something interesting. Tell me is a comp…”
Stebbings: Sending VCs three relevant deals monthly for six months gets hires
“Show the freemium version of yourself. Like, choose five VCs that you want to work with. Like, all of our portfolios are very public. Understand the type of deals they like, and for six months, send them three deals every single month. And after six months, Di…”