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Oana Olteanu: Why Founders Should Expect More From Their VCs | 20VC #950

Oana Olteanu is a Partner @ SignalFire where she focuses on enterprise software at Seed, Series A and Series B. At SignalFire, Oana has led deals in the likes of Kurtosis, Enso, Kolena, Budibase, Plural, and Explosion. Prior to joining SignalFire, Oana was at Scale Venture Partners where she invested in applied ML and developer tooling. Oana sourced Scale’s investments in Observe.ai, Flatfile, and Proscia. She was part of the deal teams for Honeycomb and AllyO (acquired by HireVue). She also supported existing portfolio companies such as Dialpad, Matillion, and BigID. Prior to Scale, Oana was an AI seed investor at SAP.io, SAP’s $35M seed fund, where she sourced the investments in Plum.io, Oto.ai, and Akorda. ---------------------------------------- Timestamps: 0:00 Who is Oana? 3:15 What are you running from/towards? 3:55 Schrödinger's VC 8:36 What should founders lean on their VCs for? 10:02 How to Give Negative Feedback 11:38 How to Scale like a Romanian 12:13 What do you do to bring your founders together? 13:31 Misalignments between VCs and Founders 15:30 The Main Ways VCs Behave Badly Today 16:15 Does Harry promote himself too much? 18:12 The Art of the Board Meeting 25:38 Hiring for Diversity 31:51 What changes do you want to see in VC? 32:22 What do you find hard about VC? 33:05 What compelled you to join SignalFire? 34:13 Oana’s Favourite Book 35:11 Most Underrated Angel Investor 35:21 What traps do most engineers fall into? 36:01 How Oana Learned to Drive a Tank 36:15 What do Oana’s parents think of her job? 36:42 Oana’s Biggest Win 37:55 What would you most like to change about VC? 39:09 What do you know now that you wish you’d know when you started? 39:55 Oana’s Most Recent Publicly Announced Investment ---------------------------------------- In Today’s Episode with Oana Olteanu We Discuss: 1.) From Tank Driving in Romania to VC’s Rising Star: How Oana made her way from driving tanks in Romania to becoming a VC? How did leaving Romania for Germany and then moving to the West Coast impact her mindset? What does Oana know now that she wishes she had known when she entered VC? 2.) How to Assess a VC: The Founders Guide: Pre-investment, how can founders know whether a VC can add value? What are the signs? What three core questions will reveal how much value a VC can add? Post-investment, what can founders do to extract the most value from their VCs? What should the founders ask their investors for help with? What should they do themselves? 3.) The VC-Founder Relationship: Oana has the highest founder NPS of any VC I have ever had on 20VC, what does Oana believe makes her founders rate her contribution so highly? What works? What does not? How does Oana give sometimes very hard feedback to founders but retain that relationship of trust and safety at the same time? What mistakes do other VCs make in giving feedback? What does Oana believe are the single biggest misalignment between VCs and founders? 4.) VCs Behaving Badly: 101 What are the single biggest ways Oana sees VCs behaving badly? How does Oana think founders expectations of the product of venture should change? Does Oana believe boards are valuable? What can be done to improve them? ---------------------------------------- #OanaOlteanu #HarryStebbings #20VC #signalfire #venturecapital

Harry StebbingshostOana Olteanuguest
Nov 19, 202241mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 3:15

    Who is Oana?

    1. HS

      Oana, this is such a joy to do. As I said, I tweeted about the most incredible rising stars to have on the show, and the influx of messages I got on the back saying you, with the most incredible praise, was wonderful. So thank you so much for joining me today.

    2. OO

      Thank you for having me. And it wouldn't be without the founders to be on this show or in Venture, so I'm very grateful to you and to them.

    3. HS

      That's amazing to hear. But I want to start with a little bit on you. So tell me, from Romania to studying in, in Germany. I heard little bits about driving tanks. Not the usual HBS and, (laughs) you know, living in Menlo Park. So how did you, you know, come to Venture and come to be the rising star, as we said, and, and now obviously a partner at SignalFire?

    4. OO

      Um, so I grew up in Romania in a village until the age of 18. At 18, I won this grand prize in a contest organized by NASA, and, uh, that was the first time for me on a plane. I was flying to Mountain View to NASA Ames. And there I was mesmerized by, uh, the amount of intelligent system work they're doing, and I knew I have to be in software. So I get back home and I tell my dad, "I want to go to college," and he got a shock because this was, uh, something new for our family. Um, and I moved to Germany by myself to study computer science, um, actually machine learning, back when MATLAB was the only MLOps tool around. Um, after classes I was working for, um, SAP and two other jobs, but SAP was the one who got me back to the Bay Area. I transferred into their, uh, Palo Alto office. My first experience in the US was finding a room to rent on Craigslist, and I ended up living in the house of the head of microelectronics division at Atari. Um, I was and still am a diehard Atari fan, so I was starstruck when I met Mr. Robert Brown. And that's when I felt like I truly arrived to, to the Valley.

    5. HS

      Can I, can I just ask you a blunt question, which is like, it's a massive move, like moving, you know, uh, halfway around the world to the US without knowing people, without having a support network. Were you nervous? And how did it feel as a young person uprooting your life?

    6. OO

      It was different, and it... I think maybe because when you're young you take more risks. But I think it's also the fact that many people don't realize that wasn't the first time I moved somewhere. The... It was a lot harder to move to Germany, um, having only known English and French, no German (laughs) and being away from home for the first time, and away to a totally different country and not having a mobile phone, um, not having a laptop, trying to get all the things set up for myself. So coming to the US was easier because I knew the language. I knew I want to come back. Ever since the NASA, the NASA experience, I knew I want to come back. So it was everything I was wishing for. But yes, it was a shock, especially as a European, to arrive at the airport and realize there is no easy public transportation to where you were going (laughs) and you have to rent a car and drive everywhere.

    7. HS

      Yeah. It's, uh, it's a shock for all Europeans. I, I do wanna-

    8. OO

      Yeah.

    9. HS

      ... before we dive into the show and kind of focus obviously on Venture and founders,

  2. 3:15 – 3:55

    What are you running from/towards?

    1. HS

      but I always believe that we're all running towards something and we're all running away from something. What, what do you think you're running from, first? And then what do you think you're running towards, Oana?

    2. OO

      I'm running from unfulfilled potential. I think there is nothing sadder than unfulfilled potential. And I'm running towards fairness and many amazing opportunities for good people. And good people are often very diverse people.

    3. HS

      I totally agree with you, especially, well, on both. Um, I'm always terrified about kind of unfulfilled potential personally, and it's, uh, what keeps me up at night. (laughs) Um, but, uh, that and tequila. Um, but I want to start on, uh, the venture market itself,

  3. 3:55 – 8:36

    Schrödinger's VC

    1. HS

      'cause when we chatted before, w- you gave me a couple of hints on where you wanted to take the conversation, and one of them was Schrödinger's VC, both helpful and useless at the same time. I had to Google Schrödinger's VC. It, it didn't really come up with anything. Apparently the combination of words don't work.

    2. OO

      (laughs)

    3. HS

      So what, what is it, and why is it helpful but also useless? (laughs)

    4. OO

      Yes. Um, Schrödinger'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. And ideally, you want to avoid the Schrödinger's VC, but if you already have one, there are ways to extract value from them.

    5. HS

      Okay. This is too... I love that. I didn't know that was the explanation. (laughs)

    6. OO

      (laughs)

    7. HS

      Okay. So first, how can we tell a Schrödinger VC before we get into a formal relationship with them? What questions can we ask? How do we determine it?

    8. OO

      I think three things. One, you have to really pay attention in due diligence process. Do they act in service of you? Not talk, act in service of you. Second, you have to select from first principles. You're rather selecting a partner rather than a firm. Would you rather go to Harvard and have an awful professor or maybe go to an okay school and learn from somebody amazing? Um, third, do you know how they react to bad news when everything, you know... the ARR (laughs) and the curve is up, everything is great, but when things are not so good, that's when, in face of adversity, true character gets revealed? So, 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 that.

    9. HS

      Okay. So that's like acting in service. How do you determine reacting? 'Cause I think now also we're seeing, you know, companies struggle for the first time in years given, you know, capital environments. Uh, how do you determine whether they react in positive and helpful ways versus negative ways?

    10. OO

      Yes. You determine by, um, basically asking them to give you an example when things were not going so well, what did they do, how did they react, and also taking that information from the founder, so triangulating from all the sides.

    11. HS

      Totally get you and agree. And then I, I would also say, ask for the reference.

    12. OO

      Yes.

    13. HS

      Like, say, "Hey, can I speak to that founder?" Would love to hear. Uh, so I totally agree with you there. Okay, so now we've kind of hopefully discovered the, you know, Schrödinger from the non-Schrödinger (laughs) -

    14. OO

      (laughs)

    15. HS

      Love this statement. Um, let's just say we made a mistake, Oana, and we're in the position now where we have one. How do we extract value from one we already have on the cap table?

    16. OO

      Yes. So the good news is you can extract value and it's up to you as a founder how to manage and keep them accountable and give them homework. For example, one of my companies asked me, "How do you nail platform ICP?" What I did was I went, did the work, collected the results, and presented it back to the founder together with a list of potential intros to relevant people. What doesn't work is you sending material or a deck before a board meeting with no asks. Usually, those tend to go. F- uh, for example, the founder presents, the VC listens, there is nothing being shared back, and that's a waste of time and, and time is precious, should not be wasted.

    17. HS

      I, I, I totally agree with you. Can I ask, in terms of, like, uh, Schrödinger's VC, um, and... (laughs) It's, uh, brilliant. Does it matter? And what I mean by that is, in the last few years, we've seen fast, cheap capital, and it's not been particularly useful, uh, either good or bad. Does it matter? And how do you advise founders on whether actually net neutral is okay? Do you know what I mean?

    18. OO

      Well, I think, as you said, in the past few years, that has happened, which has led to a bunch of, besides Twitter jokes about how useless the VCs are, also it led to very low expectations. 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 lot more games and therefore they can advise from near the chessboard. And there is value in that to the founder, and the value is there. It's up to the founder to extract it and manage the VC

  4. 8:36 – 10:02

    What should founders lean on their VCs for?

    1. OO

      and give them homework.

    2. HS

      I, I, I, I, I love that in terms of raising the bar in terms of expectation setting. There are some things I think where, like, honestly, I shouldn't help and I think it, it is their job. So I think, you know, whether it's customer intros, whether it's getting hires over the line, but I shouldn't be in charge of the hiring process.

    3. OO

      (laughs)

    4. HS

      Like, your job as a founder is to fund, hire, and expel the mission. Do you... What do you think the founders should monitor and own versus should lean on their VCs for?

    5. OO

      Yes, I do believe that hiring is the founder's job, but that doesn't mean for me as a VC, I cannot source them diverse candidates, I cannot guide them how to filter for culture in the process, that I cannot help them land amazing candidates in the final stages of the process. So all those things providing the perspective, showing them maybe ahead of time when there is a crucial moment because you've done this many times and you can sense that. Or to give an example, maybe you can sense when they are lagging behind go-to-market and they will be heading towards a very difficult fundraising process for the series A. That's a conversation a VC can have and can help the founder realize that and get back into gear. The founder is doing the work. You're just advising.

    6. HS

      Oh, well, I have to ask. The amazing feedback

  5. 10:02 – 11:38

    How to Give Negative Feedback

    1. HS

      I got, um, from everyone, but especially the founders, in how aligned you are and the relationships you have with them, how do you give negative feedback or challenging feedback and retain this? Help me out.

    2. OO

      Yes. I will give an example. So because I've invested at the later stages of Scale Ventures, I could tell that one of the founders I get to work with at seed is lagging behind go-to-market. Now, if I was a Schrödinger's VC, I would look the other way and spend my time elsewhere. I'm not one of those and so what I did, I reach out to 50 potential customers, I put together a document on the feedback, I prepared a list of 15 companies and where they were in revenue each quarter, I presented the material together to the founder, and I've made intros for him to other founders who have overcome that hurdle. Founder-to-founder talk always beats VC talk. That way you show that you're supportive, you also put the bone to work, and you provide data so the founder themselves, they actually can reach to that conclusion.

    3. HS

      (laughs) I mean, it, it's amazing to hear. My, my question is- Honestly, and I, I'm being very transparent, I do not do that. I mean, it's not my style of venture, number one. But, like, fundamentally, I think a generation of vent- VCs doesn't, because we can't. I mean, my portfolio, I've got 150 investments, I do 35 a year. Um...How do you advise- like, is that model only worthy if you have few investments?

  6. 11:38 – 12:13

    How to Scale like a Romanian

    1. HS

    2. OO

      I think if, for example, um, in the beginning, I only had a couple. Now, I'm at nine. Um-

    3. HS

      Ooh.

    4. OO

      ... and the way I scaled myself is I adopt the Romanian village mentality of, if you get it, if you raise one or two of the kids right, the other kids will raise themselves. And maintaining this sense of community among the founders that they do want, not, nobody asks them, I don't ask them, they want to help each other out and elevate each other and, and help each other overcome these, these

  7. 12:13 – 13:31

    What do you do to bring your founders together?

    1. OO

      common hurdles.

    2. HS

      Can I ask, do you do anything to bring them together? Is it in-person dinners, drinks, events, meetups, hackathons? Is it WhatsApp groups? Slack groups? What do you do to create that- I love that Romanian family analogy.

    3. OO

      Well, ideally, I would love to get all the founders I get to work with together for an offsite for tank driving. But that hasn't happened yet, and many of them are all over the world. So, um, there is a Slack channel, uh, where founders that I get to work with or founders where I'm not an investor but they say I'm on their mental cap table, I invited them all there and they can be vulnerable and share how hard it is as a founder or ask each other what's fair compensation for each stage. It's a safe environment with no VCs. Um, I only chime in if there are some data points that I can share. Other than that, it's their space.

    4. HS

      Can I ask? I- I love how founder-aligned you are. Um, I- I feel like this evil Wall Street character 'cause like- (laughs) you- I'm not quite as founder-aligned as you are, uh, to be blunt. Um, the joys of podcasting is you edit out some things. Um, but in terms-

    5. OO

      (laughs)

    6. HS

      ... of, uh, like alignments, um, there are some things where founders and VCs

  8. 13:31 – 15:30

    Misalignments between VCs and Founders

    1. HS

      are just not aligned. What do you think are some of the misalignments between VC and founder if we put on our idealist- on, on our kind of pragmatist hat?

    2. OO

      I think it doesn't have to be. Our job as investors is to maximize the success of the companies while listening carefully to the founder. So I think if you manage to do that, there can be goal congruency and the founder can feel like they have the sounding board that they desperately need.

    3. HS

      Okay, here's an example. You have a seed fund. The seed fund has an amazing position in this company. Um, but actually, the rest of your portfolio is not very good and you need DPI to show to your investors and you need to return cash back to them to get the new bigger fund that you need because you've just hired a bigger team. 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.

    4. OO

      Think it depends on the type of VC again. I like to think long term. And long term, long term and also putting the founder's needs first. At the same time, if I'm selling my position in a company, that doesn't mean I cannot still be there for them. I left Scale Ventures, I'm still very much in touch and there for whenever the founders need me. So I think it's a talk with the founder and figure out what's best for them and where there is a will, there is a way.

    5. HS

      Can I ask, we- we mentioned Schrödinger's VC, um, and we mentioned about VCs selling positions, which can be done graciously and some not so graciously. (laughs) Um, uh, I- I have to ask, uh, Jay at, um, at- J- JDAS, uh, told me before the show that, um, you're very outspoken when it comes to bad actors in venture. Um,

  9. 15:30 – 16:15

    The Main Ways VCs Behave Badly Today

    1. HS

      I'd love to hear, what are the main ways you think VCs behave badly today?

    2. OO

      I think a lot of VCs who recently joined the industry, um, they take this common approach of constant self-promotion and that erodes the mind and spreads misinformation among the founders. Um, yes, I am outspoken. 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 2022 and- and there is no excuse to- to hire only like that.

    3. HS

      I totally agree with you on the hiring diversity wise. On the promotion

  10. 16:15 – 18:12

    Does Harry promote himself too much?

    1. HS

      side, people would say that I promote myself too much. What do you say?

    2. OO

      I think you're providing valuable, actionable tactical advice. I follow you on Twitter and I'm amazed how focused you can be and how valuable the advice is. And the proof of that is I'm sending it to my founders, I'm forwarding some of the tweets, and I think that's amazing. I think as long as you provide value versus serve your own ego, then that's a winning formula.

    3. HS

      Oana, firstly, I'm very touched and thank you. Secondly, I- I- I totally agree. I think if you're providing value back into the ecosystem, it makes sense. Chest pumping doesn't. I- I do also think though, like we do sell cash, which is the most basic form of commodity, and to a certain extent, you do have to tell the world how good you are. Um, and actually, I- and I mean this not patronizingly, but like, the references I get on you, the world should hear what people have to say about you. And so whether that's you telling that or whether it's them telling the world, someone needs to be the messenger to the broader population on how good you are with your founders. And so I- I actually-... I would, I would almost say you're doing a disservice to yourself by not being more promotional. (laughs) So I guess I'm pushing back a little bit, but in-

    4. OO

      (laughs)

    5. HS

      ... a pro way, because people need to know, and as you said, in a world of decentralized talent, if you are in, uh, uh, Paris, or Bucharest, or Sydney, it's, it's how we discover today through Twitter, because they don't know the engineers in this specific circle. So I, we can talk about promotional elements in, in other areas. Um, I, I do wanna ask, though, you know, uh, well we've spoken about Schrodinger's many, many times, VCs often claim to their LPs that boards,

  11. 18:12 – 25:38

    The Art of the Board Meeting

    1. HS

      boards are where we're valuable. Do you think boards are valuable, Ioana? 'Cause you've seen them across spectrum, I guess, with Scayul and then with Signalfire. Do you think they're valuable?

    2. OO

      I think putting aside the governance issues, um, they're valuable in seeing some of the functional leaders present. That gives you as a board member a better lens into how the founder built the team, but also gives these functional leaders a voice.

    3. HS

      Totally agree. Who's the best board member that you've sat on a board with, and why?

    4. OO

      This is a hard one because I do sit on a bunch of boards with very amazing people. (laughs)

    5. HS

      Nevermind, none, n- none of them will listen, it's just you and me.

    6. OO

      (laughs)

    7. HS

      (laughs)

    8. OO

      I, I will pick the most, uh, recent board meeting, and that was with, uh, Dan Scholnick, who invested in New Relic, Docker, Weights & Biases, and a bunch of other amazing companies. Um, I like Dan because he's low ego, he's very action oriented, and he acts in service of the founders.

    9. HS

      I, I, I love that, and thank you for giving one, very few people actually give one, so I'm super grateful for that. In terms of your learning process on like what it takes to be a good board member, like what do you think are the biggest mistakes you see younger people and younger investors make on boards that you've observed?

    10. OO

      As a younger investor, you tend to talk too more, too much, and not listen, so I think that's the biggest mistake.

    11. HS

      I totally agree. I also think for founders, it's very tough, like young founders, how do you know how to run a board meeting? It's, it's-

    12. OO

      (laughs)

    13. HS

      ... not a normal skill to learn at school or university. What advice do you give to young founders on how to, first prepare actually, and then how to execute a board meeting? I'd love to hear your thoughts on that.

    14. OO

      So I had, uh, a board meeting recently, uh, first time founders where the founders told me they watched the Silicon Valley, um, HBO show to prepare for the board meeting. (laughs)

    15. HS

      (laughs) You're like-

    16. OO

      And-

    17. HS

      ... "No, no, no, don't do that." (laughs)

    18. OO

      Yeah. (laughs) Yes. (laughs) Um, I d- so I have a guide on this and it's public that I share with founders, um, you have to basically distill down what has happened and talk about some highlights, low lights, um, be able to, um, before the board meeting, talk with each board member individually, figure out what is it that they want to talk about, and ask them for, even like three things. Ask them to do some homework, be prepared, come to the board meeting ready to have a discussion and, and add value. If you're not doing any of these things and you just show up, it might be okay for a first board meeting where people are still getting to know each other and it's anyway a very early stage company, but ideally you have to prepare. Board meetings can be very valuable if you do the work upfront.

    19. HS

      I totally agree with you on the call beforehand, I just haven't had anyone do it. (laughs) Um, so I completely agree with you. The, the other thing I would say is actually I, I really like it when they send not slide decks, 'cause they can just be used-

    20. OO

      Yeah.

    21. HS

      ... as like crutches, but like a doc, and then I say send it in a Word doc, not a Google Doc, 'cause if you send it in a Word doc, you write in isolation, 'cause if, you know, you're much more engineering centric than me, if you make a comment, I'm not gonna argue with you Ioana, because you're much smarter than me, especially when it comes to technical. But that's a shame, I should comment, and so doc is better than a Google Doc because it brings out the truth more I find. So totally agree there. In terms of the execution, we're in the board meeting, how do you advise young founders in terms of running the best board meeting in, in actual play?

    22. OO

      First of all is focus and getting to the heart of the issue. If there is anything that people can be informed beforehand, we don't need to reiterate it in the meeting.

    23. HS

      Yeah.

    24. OO

      Let's talk about the meaty topics. And also, reading the room and sometimes you might have an investor which acts like the mob and (laughs) tries to monopolize the entire discussion and, and you have to stop that as a founder. You control the board meeting and it's on you to give, uh, everybody room.

    25. HS

      What's the right way to stop that? I l- I'm sure we've both seen it, I've seen it often at some, you know, middle-aged white guys-

    26. OO

      (laughs)

    27. HS

      ... um, and I feel v- (laughs) uh, obviously I'm a young white guy-

    28. OO

      (laughs)

    29. HS

      ... so it's very different. Uh, (laughs) very different, I'm much better.

    30. OO

      (laughs)

  12. 25:38 – 31:51

    Hiring for Diversity

    1. HS

      moderated temperament. In terms of kind of taking it back to the team, the challenge is when you take it back to the team today, the team is mostly white engineers or male-

    2. OO

      (laughs)

    3. HS

      ... engineers. And, and one area where you've really, I think, done just so incredibly well, um, and many obviously told me about how well you've done and the work that you've done, is in terms of really kind of making a change and making a difference in hiring women, uh, in kind of startups, but also engineering specifically. Uh, you've said before that it's not the hardest thing to do. So, why is it not? Why do you think it's over-exaggerated, and what are founders doing wrong today, just to set the scene?

    4. OO

      Yes. I think you cannot hire diverse people if they are not even in your candidate pool.

    5. HS

      Mm-hmm.

    6. OO

      And so if you cannot get them into your pipeline, you should make a list with what makes your company attractive to these people. And if that list is short (laughs) or there isn't anything you can put on the list, then the problem is you and the non-inclusive policies, and you should revise that.

    7. HS

      So, if we then kind of revise that and we think, "Okay, these are the four or five things that make it attractive," um, but honestly, we came out of Berkeley or Stanford, and I've just got a load of n- guys as my friends who I've got as the talent pool. Sorry, it's just common, we both know. (laughs)

    8. OO

      (laughs)

    9. HS

      Um, what can I do to diversify my pipe to then work to bring in amazing female talent? What works? What doesn't work?

    10. OO

      I think first being aware of unconscious bias. We tend to, when faced with a new task, to draw upon what has worked in the past. And so, if you worked in all-male teams and you do what has worked in the past, you might not lead down the path to where you can have diversity in your team. Then there are three things you could, like, places where you can find these people. One, for your re- recruiters. I keep hearing from founders that, "I told my recruiters I want more women, but they keep bringing me white males." Well, get another recruiter. Second, you could, for example, reach out directly, but do it in a respectful manner, in a manner where you don't reduce people to their gender. Just saying that, "I want to hire women developers, and I think you would be great for the role," like, who wants to work for such a company? Um, and third, um, in my free time I started this thing called She's Ready to Dev, which is a community for technical women. It's free, no sponsors. You can post the job there, you can browse the candidate lists. And, and that's a way where I'm doing the work for you. You have to be intentional, and you have to be able to hire these people to win them over.

    11. HS

      You said about winning them over. So, say we increase the, the quality of diversity within our pipe. Great, we're super happy with that. But they've always got multiple offers, like any great person does. How do we win them, and what does it take to get them over the line?

    12. OO

      An example of this, for example, is, uh, Ashley at Axo. She hired the first four people, all women. So, what helps, if you have women in leadership, and second, if you have inclusive policies and processes to collect feedback from all, and you don't talk in the abstract that you're committed to diversity. You actually show some of these policies.

    13. HS

      I'm sorry, I'm just asking the basic questions 'cause I know there's a load ... I'm writing down on my hand notes. (laughs)

    14. OO

      (laughs)

    15. HS

      Uh, because I know there's a load of dudes who are gonna be listening on, like, a subway or on a tube going, "Okay, great." Wh- what are inclusive policies? Just, just to help me actually understand that.

    16. OO

      Benefits, parental leave, both for men and women, resource groups, training, introductions to potential mentors. And I do get that if you're an early stage company, you might not have the time to think about this because you're maybe seed or pre-seed, or maybe you might not have the time as a CEO to, to coach some of these people who maybe just graduated from Berkeley and are- they're just getting their first job. But there are other people that you could introduce them and, and give them that feeling that you are setting them up for success, that if they are joining, they're not just joining to be your token woman. You actually care about helping them thrive.

    17. HS

      Does it piss you off when you see the token woman? (laughs)

    18. OO

      Oh, all the time. I was countless time the only female at the startup working or in an engineering team, and now in boards, so, yes.

    19. HS

      Do you feel that? And I don't mean that too personally, but do you feel like you're the only woman or actually do you find them quite inclusive where you're like, "Ah! I am, but I- I feel fine"?

    20. OO

      Sometimes I do feel like I'm the only woman and the struggle is very much real. Um, but I think as you establish a relationship with people and you earn their respect, even if you might be the youngest person in the room, things are starting to course correct.

    21. HS

      Do you think things... Sorry, I'm just completely going off course here. Do you think things are going better or worse in this respect? 'Cause I'm worried actually, in um, e- economic downturn, f- you know, economics wins, diversity and climate specifically are two that lose generally. Um, do you agree with me and do you share the same concern?

    22. OO

      I think there are people who are trying to make a difference who do not care if what gender you are as long as you're building an amazing company. I think you just have to seek them out and for us to make any changes we have to focus on the positives and those people and help each other out. So, if a female founder reaches out to me, even if it's out of my field of infrastructure and developer tools, I'm not going to be, "No thank you. It's not worth my time. It doesn't make me any money." I will try and get her introductions. I will post in the VC channels I'm part of. I will provide feedback on her deck. I will try to do something.

    23. HS

      I- I- I totally

  13. 31:51 – 32:22

    What changes do you want to see in VC?

    1. HS

      get you and uh, agree. Can I ask, what would you like to see change? What do you think really still needs to be changed despite the improvements that have been made?

    2. OO

      What I would like t- the- the best to see is VCs who are in the business to serve the founders versus being in ventures to serve their ego. I think if you start with that thinking in mind, things will change. And yes, the founders don't have to be only men. You're there to serve the founders and the mission of those companies and

  14. 32:22 – 33:05

    What do you find hard about VC?

    1. OO

      that doesn't have gender in it at all.

    2. HS

      Can I ask, what do you find really hard about venture?

    3. OO

      The hardest thing coming from a operator role was the fact that you can work for months on something and not have (laughs) anything to show. While before I would go to a customer conference, show the product, there was something tangible.

    4. HS

      I- I totally agree with you. I- I find it now obviously, run a media company where if you put in four hours of work you get four hours of work. And then venture, you do a week of r- uh, of meeting founders, deep dives, whatever, and it's like, "Well, that wasn't actually an interesting space (laughs) in the end." (laughs)

    5. OO

      (laughs)

    6. HS

      I- I totally agree with you there. Can I ask on Signal Fire, why did you join Signal Fire? And as I said, you know, Walter

  15. 33:05 – 34:13

    What compelled you to join SignalFire?

    1. HS

      Jim said the most amazing things. Talk to me, what compelled you to join Signal Fire?

    2. OO

      Yes, so at Scale Venture Partners I got my green card, and once I had my immigration freedom I wanted to invest at the earlier stages. And the other compelling factor was the focus on founder NPS. And not only verbal but also in action. Signal Fire has a world-class portfolio support team and a data science platform called Beacon, an engineering team. That's where I ha- I hang out with them. My desk is with the engineering team. It attracted me, that aspect of you can have a VC fund which is built like a tech company. And if I'm not mistaken, that it was the first VC fund built like a tech company.

    3. HS

      Yeah. No, I- I think it was. I remember Chris Farmer five or six years ag- I'm- I'm showing my age here, Oana, but sh- uh, came on the show and talked about his, like, plans to do it-

    4. OO

      (laughs)

    5. HS

      ... I think at the time. Um, so I totally agree with you. I do wanna move into a quick fire round here. So as you know, I say a short statement and then you give me your immediate thoughts. Does that

  16. 34:13 – 35:11

    Oana’s Favourite Book

    1. HS

      sound okay?

    2. OO

      Yes.

    3. HS

      So you have a very well-prepared, um, bookshelf behind you, so this should be an interesting one.

    4. OO

      (laughs)

    5. HS

      What- what's the favorite book and why, Oana? (laughs)

    6. OO

      I think right now is, um, The Daily Stoic because it helps me slow down and sometimes I post, it's one thing per day and- and fathers also find it very helpful. It speaks differently to each person reading it.

    7. HS

      Sorry, The Daily Stoic, that's a book? It's a blog? It's a...

    8. OO

      It's a book.

    9. HS

      (laughs)

    10. OO

      It's basically-

    11. HS

      Ooh.

    12. OO

      ... this book.

    13. HS

      Oh, wow. And so you... Oh, Ryan Holiday. Yeah.

    14. OO

      And you can... It's one per day.

    15. HS

      I like that. Yeah. I like it as well. I'm- I'm not much of a reader and so anything longer-

    16. OO

      (laughs)

    17. HS

      ... than a tweet, uh, I find, uh, too challenging. Uh, tell me, what do you believe that many around you do not agree with?

    18. OO

      Foundational models. I think they will get commoditized like compute, and I think the companies who deliver the last mile

  17. 35:11 – 35:21

    Most Underrated Angel Investor

    1. OO

      will be the ones to capture most value.

    2. HS

      Who do you think is the most underrated angel in the ecosystem and- and why them?

    3. OO

      Christine Yen, the CEO of Honeycomb.

  18. 35:21 – 36:01

    What traps do most engineers fall into?

    1. OO

      She has a ton of knowledge and know-how.

    2. HS

      What predisposed traps do most engineers fall into?

    3. OO

      I'll cover three of them. First, when out of the comfort zone we fall back into what we know best, which is write more code instead of talking with customers.

    4. HS

      Mm-hmm.

    5. OO

      Second, we do have a passion for technology, however, if you want to reach wide adoption you have to talk about the developer experience first. Pay attention to what words Vercel uses on their website. Um, third, if you, we have this belief of everything has to be organic. And it doesn't have to be organic. If it saves you time, why not pay for it?

  19. 36:01 – 36:15

    How Oana Learned to Drive a Tank

    1. OO

    2. HS

      (laughs) I love that. Um, how did you learn to drive a tank, Oana?

    3. OO

      I grew up playing in a tank. My dad is a tank mechanic. And I love the feeling that a tank gives you of, uh, basically feeling unstoppable. You

  20. 36:15 – 36:42

    What do Oana’s parents think of her job?

    1. OO

      can overcome any obstacle.

    2. HS

      Do your parents understand what you do at all?

    3. OO

      No, they think I fix computers. So whenever I go home, (laughs) all the neighbors come with something broken that I could fix.

    4. HS

      (laughs) I love that. Um, tell me, what is your biggest miss and how did it change your mindset?

    5. OO

      MindsDB, move faster.

    6. HS

      Hmm. That's such a hard one. Move faster is a, (laughs) I

  21. 36:42 – 37:55

    Oana’s Biggest Win

    1. HS

      g- I get you, but yeah, fair. What's your biggest win so far and how did that impact your mindset?

    2. OO

      There is a company in stealth using LLMs for dev tools, and it was a very competitive round. I went the extra mile and it reinforced that hustle does pay off, even if you go against some top-tier funds.

    3. HS

      How did you go the extra mile in this case, if you can share that?

    4. OO

      Yes. Um, I put... When I was told that they're likely to go with another bigger brand, I put together a pitch back tech based out of completely just memes. But also with content of what is the vision I see for potentially the product and why I'm excited, um, especially for these large language models to now be applied in the developer tooling space. And I was told it was funny, and they got also some ideas they haven't thought about it before. Um, I was also sick with COVID and coughing my lungs out while giving this presentation. So all those things together, uh, were appreciated by the founders and they decided to join SignalFire.

    5. HS

      I love that. That's, uh,

  22. 37:55 – 39:09

    What would you most like to change about VC?

    1. HS

      that's fantastic. A deck full of memes.

    2. OO

      (laughs)

    3. HS

      Um, what would you most like to change about the world of venture?

    4. OO

      I would like for, for VCs to pay more attention to the founders, listen to them, and, and do more work. And maybe change a bit the, the reputation that a VC has. I... Even today when somebody calls me a VC, I, I cringe a little (laughs) because I don't see myself as the vest-wearing person who talks a big game, is a blowhard and, you know, (laughs) does not really (laughs) care about the, the founders. Um, that's not me. And I think that kind of perception deters other people like me to get into ventures. And to be honest, the only reason how I landed in ventures is, I'm an immigrant, Skale promised me to scon- sponsor a green card. And, and I said, "Sure, I can be a VC." And while I was a VC, I got a taste for working with founders and, and I felt like this is, this is... doesn't feel like a job to me when I work with the founders. And so I didn't know I want to be a VC until I was one

  23. 39:09 – 39:55

    What do you know now that you wish you’d know when you started?

    1. OO

      for immigration reasons.

    2. HS

      What do you know now that you wish you'd known when you started in venture?

    3. OO

      Just focusing on your strengths and finding your own style. And being honest and trying to be helpful gets you a long way. You don't have to be part of the golf club or the battery club or whatever club. Um, you can just be yourself and people will appreciate that.

    4. HS

      Uh, yeah, it's so funny you say that. Mine's exactly kind of the same. I say like, there's no right way to do venture. I, I looked at people before and I was like, "Oh, I have to be analytical or I have to be engineering-centric." No, it's just about finding your way of doing it, which is fine, as long as you're good at it, hopefully.

  24. 39:55 – 41:04

    Oana’s Most Recent Publicly Announced Investment

    1. HS

      (laughs)

    2. OO

      Yes. (laughs)

    3. HS

      Um, uh, final one for you. What's the most recent publicly announced investment and why did you say yes and get so excited?

    4. OO

      Yes. The most recent publicly announced is Kertosis. Um, it containerizes entire distributed systems and allows testing on them. The Ethereum Foundation used them to test the merge, for example. I said yes because the founders, um, showed deep care for the product, technical rigor, and they are also very deep reflective thinkers who actually do pay a lot of effort into building a, a healthy culture. And, and if you ask any of my founders, they will tell you, "I don't like to work with jerks." So (laughs) that's very important for me. You can be amazingly smart, but you also have to actually want to build a healthy culture in your company.

    5. HS

      Oana, I've absolutely loved doing this. Thank you so much for joining me today. As I said, I heard so many great things. I felt quite unfair 'cause I knew all this about you. And so the asymmetric information was, uh, very unfair of me, but I love doing it. So thank you so much for joining me today.

    6. OO

      Thank you. It was a pleasure meeting you, and I love the show.

Episode duration: 41:05

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