Oana Olteanu on What Founders Should Expect From Their Investors

Oana Olteanu grew up in a Romanian village and left at 18 after winning a NASA competition. Her visit to NASA Ames introduced her to work on intelligent systems and convinced her to study software. She moved alone to Germany to study computer science and machine learning, working several jobs alongside her studies.

A job at SAP eventually brought her to Palo Alto. She recalls finding a room through Craigslist in the home of Atari microwave electronics division head Robert Brown, an exciting coincidence for an Atari fan. Moving to Germany had been harder than moving to the US, she says, because she initially knew no German and had no phone or laptop.

Asked what drives her, Olteanu says she is running from unfulfilled potential and toward fairness and opportunities for good people. She connects opportunity with diversity, a theme that recurs throughout the conversation.

Her term “Schrödinger's VC” describes an investor who promises extensive help before a deal but whom founders later find has added little value. She thinks founders can avoid such a partner by examining actions during diligence rather than accepting promises.

She recommends choosing the individual partner, not only the firm, and asking how the investor behaves when a company encounters bad news. Ask for examples across the portfolio and speak directly to the founders involved. An investor taking credit for a founder's work is, in her view, a warning sign.

If the investor is already on the cap table, she says founders can still make specific requests and hold them accountable. For one company she researched the ideal customer profile, gathered findings and prepared relevant introductions. Sending a board deck without clear requests, she argues, often yields passive meetings.

Harry Stebbings asks whether a neutral investor matters when capital is cheap and fast. Olteanu says recent experience has lowered expectations until some founders consider a non-harmful VC a success. She wants founders to expect more: an investor cannot play the founder's chess game, but experience from observing other games can inform advice.

Stebbings draws a boundary: a founder must own hiring, fundraising and the mission, even if investors help with introductions or closing candidates. Olteanu agrees that hiring is the founder's job, while proposing that investors source diverse candidates, help assess culture and warn of challenges they recognize from experience.

She gives an example of difficult feedback to a seed founder whose go-to-market progress seemed slow. Rather than simply delivering criticism, she says, she contacted 50 prospective customers, documented feedback, assembled quarterly revenue comparisons for 15 companies and introduced the founder to peers who had overcome similar problems.

Stebbings acknowledges that he cannot work this way across his reported 150 investments and roughly 35 new investments a year, and asks whether the model requires a small portfolio. Olteanu says she had nine companies at the time and uses a Romanian village analogy: build a community where founders choose to help one another.

Her founders' Slack community includes people in whom she has not invested but who consider her part of their “mental cap table.” She says it gives founders a space to discuss difficult experiences and compensation, with her participation mainly limited to sharing useful data. A planned group tank-driving outing had not yet happened.

The conversation turns to incentives that can divide founders and investors. Stebbings describes a seed fund needing distributions to investors, or DPI, to raise a larger fund: selling a valuable stake for the fund's needs may be poorly timed for the founder. This is a hypothetical illustration of the conflict, not a reported transaction.

Olteanu emphasizes discussing the founder's needs and taking a long-term view. She says an investor can remain helpful after selling a position or changing firms, noting that she still keeps in touch with founders from Scale Venture Partners. Her response does not eliminate the economic conflict Stebbings identifies.

She criticizes investor self-promotion that takes credit for founders, and all-white male associate cohorts in 2022. Asked whether Stebbings himself promotes too much, she distinguishes useful tactical content from promotion that serves only the investor's ego.

Stebbings pushes back that capital is a commodity and investors must communicate what they offer, especially to talent outside established networks. He argues that founders' positive references for Olteanu should reach a wider audience. They agree that the value of public communication depends on what it contributes.

Aside from formal governance, Olteanu sees value in board meetings because functional leaders can present their work, giving directors a view of the team and giving those leaders a voice. She names Dan Scholnick as an example of a low-ego, action-oriented board member who serves founders.

Her advice to younger board members is to listen more and talk less. She recalls first-time founders who watched the HBO show Silicon Valley to prepare for a meeting and offers a more practical approach: summarize highlights and lowlights, and speak with each director before the meeting.

A founder can ask each board member to prepare a few contributions or complete specific homework. Preparation allows the meeting to focus on discussion instead of a one-way update. Stebbings agrees and describes his preference for a written document that lets directors form views independently.

During the meeting, Olteanu recommends addressing substantive issues rather than repeating material already circulated. If a director monopolizes the conversation, the founder can redirect it or ask an ally in advance to intervene with a question and suggest returning to the main topic.

Some boards meet without the founder afterward. Olteanu says alignment among directors can help, but she always debriefs the founder, sharing positive and constructive feedback and offering help. For later-stage companies she also values clarity on quarterly expectations and feedback on functional leaders.

Asked how candid founders should be with their teams about difficult board meetings, she says transparency should be respectful and create a relationship in which people can share bad news. The aim is to understand what happened and what actions might improve the next outcome.

Stebbings asks why engineering teams still struggle to hire women. Olteanu says a company cannot hire diverse candidates who never enter the pipeline. If it cannot identify what makes the workplace attractive to them, she advises examining its policies and inclusiveness.

She warns that people often repeat the hiring patterns they already know. If a recruiter consistently produces only similar candidates, consider another recruiter. Direct outreach should respect candidates as individuals rather than reducing them to their gender.

Olteanu created She's Ready to Dev, a free community for technical women where companies can post jobs and review candidate lists. She says expanding a pipeline is only a first step: companies must also win candidates over by showing inclusive leadership and real practices rather than abstract commitments.

Asked for examples of inclusive policies, she mentions parental leave, training and access to mentors. Even a very early company with limited management time can introduce a new graduate to someone who will help them develop. The objective is to set employees up to thrive rather than treat one woman as a token.

Olteanu says she has often been the only woman on an engineering team or board and that the experience can be difficult. She also describes relationships and earned respect as ways situations can improve. Stebbings worries that economic downturns may push diversity and climate priorities aside.

Rather than claim the problem is solved, she says people trying to help should find one another and act. If a woman founder contacts her outside her infrastructure or developer-tools focus, she says she will try to offer introductions or feedback rather than dismiss the request as commercially irrelevant.

She wants venture investors to serve founders and their missions rather than their own egos. One difficult adjustment from operating to investing was working for months on an opportunity without a tangible result, compared with showing a product at a customer conference.

Olteanu says she joined SignalFire after obtaining a green card at Scale, because she wanted to invest earlier and liked SignalFire's focus on founder feedback, portfolio support and its Beacon data platform. As a SignalFire partner, she has a direct professional interest in describing that model favorably.

In the quick-fire round, she chooses The Daily Stoic as a book that helps her slow down. She predicts foundation models will become commoditized like compute and that companies delivering the “last mile” may capture much of the value; this is her 2022 view, not an established outcome.

She names Honeycomb CEO Christine Yen as an angel who shares knowledge generously. Asked about engineers' traps, she lists writing more code instead of speaking with customers, emphasizing technology over developer experience, and assuming every growth channel must be organic rather than paid.

Her father is a tank mechanic, and she says she grew up playing in tanks and enjoys the feeling of being able to overcome obstacles. Her parents do not fully understand her investing job, she jokes; they think she fixes computers, so neighbors bring broken devices when she visits.

Olteanu describes winning a competitive investment in a company using language models for developer tools. When she heard a larger brand might win, she prepared a pitch deck made of memes alongside product ideas, presenting it while ill with COVID. She says the founders appreciated the effort and chose SignalFire.

She would like VCs to listen more and improve the profession's reputation. She says immigration circumstances first drew her into venture: Scale offered to sponsor a green card, and she discovered that working with founders suited her. She did not know she wanted to be an investor until she became one.

Her advice to her younger self is to develop an authentic style, work from personal strengths and be helpful rather than imitate a particular club or archetype. Stebbings agrees that there is more than one way to practice venture, provided one does it well.

Her most recently announced investment at the time was Kurtosis. She describes its software for testing distributed systems and says the Ethereum Foundation used it to test the Merge. She cites the founders' product care, technical rigor, reflective thinking and attention to healthy culture as reasons for investing; these are her account and investment judgment.