Nov 19, 2022 · 41m · news
Oana Olteanu: Why Founders Should Expect More From Their VCs | 20VC #950 · 20VC with Harry Stebbings
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, SignalFire Partner Oana Olteanu shares her unique journey from a Romanian village to Silicon Valley and outlines tactical strategies for how founders can vet, manage, and extract maximum value from their venture capitalists.
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 37.6% of the talking time here. How this is scored →
Harry as informed peer 3.6 Guest teaching 4.3 Guest disagreement 2.0 Harry pushing back 3.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 15:34 Calling out bad venture actors and non-diverse hiring
Oana forcefully criticizes VCs who focus on constant self-promotion and openly calls out firms announcing associate benches made up entirely of white males.
Hardest push from Harry ▶ 16:52 Harry defends VC self-promotionHarry explicitly rejects Oana's anti-promotion thesis, arguing that capital is a commodity and marketing oneself is required to reach decentralized founders.
Biggest teaching moment ▶ 4:16 Defining Schrodinger's VC and diligence stepsAfter Harry admits to having to Google the term, Oana breaks down the concept of Schrodinger's VC and provides actionable framework steps for founders.
Harry holds his own ▶ 14:00 Pressing on seed fund DPI pressureHarry uses his operational understanding of venture economics to present a sharp counter-example where fund DPI needs clash directly with founder interests.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Oana Olteanu's Journey to Silicon Valley | 1 | 1 | 0 | 1 | Harry welcomes Oana and asks open-ended questions about her background moving from Romania to Germany and the US. Oana shares her personal journey into software and venture without conflict. | |
| The Concept of Schrodinger's VC | 2 | 6 | 1 | 1 | Harry admits having to Google the term 'Schrodinger's VC' after Oana introduced it. Oana educates Harry on the definition and provides three concrete diligence steps for founders evaluating VCs. | |
| Maximizing Value and Setting Board Expectations | 4 | 5 | 2 | 3 | Harry questions whether net-neutral VCs are acceptable and asserts boundaries for founder responsibilities like hiring. Oana reframes this by explaining how VCs can constructively advise from near the chessboard without micromanaging. | |
| Delivering Feedback and the Romanian Village Mentality | 5 | 4 | 2 | 6 | Harry challenges Oana's founder-aligned idealism by pressing her on portfolio size constraints and the harsh reality of VCs needing DPI to raise new funds. Oana responds by detailing her hands-on approach and peer-support model. | |
| Bad Venture Actors and the Self-Promotion Dilemma | 6 | 3 | 4 | 6 | Oana criticizes bad venture actors who engage in ego-driven self-promotion and post non-diverse team photos. Harry explicitly pushes back, arguing that money is a commodity and public self-promotion is essential for reaching global talent. | |
| Running Effective Startup Board Meetings | 5 | 4 | 2 | 3 | Harry demonstrates board expertise by advocating for Word docs over Google docs to encourage candid notes, while asking how founders can shut down aggressive VCs. Oana provides tactical advice on pre-board calls and leveraging boardroom allies. | |
| Inclusive Hiring and Female Engineering Talent | 3 | 6 | 3 | 2 | Oana dismantles typical founder excuses regarding diverse candidate pipelines and tokenism, offering specific tactical fixes and benefits policies. Harry plays the inquiring host asking for practical definitions. | |
| Quickfire Round: Stoicism, AI, and Tank Driving | 3 | 5 | 2 | 2 | In a fast-paced quickfire segment, Oana shares strong counter-consensus opinions on foundational AI models and engineering pitfalls. Harry guides the conversation amicably, reflecting on different venture styles. |
Statements from this episode (17)
Olteanu: 'Schrödinger's VCs' promise help but add no value post-investment
“Schrodinger's VC is what I call a VC who preaches a lot of help, especially before winning a deal. But then if you ask the founders, they will tell you they added no value.”
Olteanu: VCs taking credit for founders' work is a major red flag
“A positive sign would be them walking you through their entire portfolio, and especially how they serve the founders when things were not going so well. A negative sign would be Them taking credit for the founders work, and there's nothing more sinister than t…”
Olteanu: Founders should expect more from VCs than just doing no harm
“Right now, many founders will tell you that if a VC is not harmful to the company, that's already a success. And I say the expectations should be higher from founders because while a VC cannot play the chess game for you and move the pieces. They have seen a l…”
Stebbings: A founder's job is to fund, hire, and drive the mission
“Like, your job as a founder is to fund, hire, and expel the mission.”
Olteanu: Founder-to-founder advice always beats VC advice
“Founder to founder talk always beats VC talk.”
Stebbings: 20VC holds 150 investments and makes 35 new deals annually
“I mean, my portfolio, I've got a 150 investments. I do 35 a year.”
Stebbings: Seed VCs seeking early DPI creates core misalignment with founders
“It is not in the interest of the founder for you, the lead seed VC, to sell your position at this time, but It is in your interest because you need to provide DPI to your investors. Very common right now. Core misalignment between founder and VC.”
Olteanu: Constant self-promotion by new VCs spreads misinformation to founders
“I think a lot of VCs who recently joined the industry they take this common approach of constant self-promotion. And that erodes the mind and spreads misinformation among the founders.”
Olteanu: There is no excuse for all-white male VC associate classes
“I will call out if a VC takes credit for a founder or if they announce their newest associate bench, which is all white five, you know, five white males. I think it's 20, 22 and there is no excuse to hire only like that.”
Olteanu: Dan Scholnick is an exemplary low-ego, action-oriented board member
“Dan Sholnik who invested in Urelic, Docker, Weights and Biases, and a bunch of other amazing companies. I like Dan because he's low ego. He's very action oriented. And he acts in service of the founders.”
Olteanu: Younger investors' biggest board mistake is talking too much
“As a younger investor, you tend to talk too much and not listen, so I think that's the biggest mistake.”
Stebbings: Word docs yield truer board feedback than Google Docs
“I really like it when they send, not slide decks, because they can just be used as like crutches, but like a doc, and then I say send it in a Word doc, not a Google doc, because if you send it in a Word doc, you write in isolation, because if, you know, you're…”
Olteanu: Founders must prevent dominant investors from monopolizing board meetings
“And sometimes you might have an investor which acts like the mob and tries to monopolize the entire discussion and you have to stop that as a founder. You control the board meeting, and it's on you to give everybody room.”
Olteanu: AI foundational models will commoditize like compute power
“Foundational models. I think they will get commoditized like compute, and I think the companies who deliver the last mile will be the ones to capture most value.”