About this episode

What happens when a CEO who helped build Old Navy from a startup into an $8 billion company decides to flip venture capital on its head? Dawn Dobras reveals the shocking truth: 93% of venture capital goes to men, and she’s built a fund that’s 70% female investors to change that.

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10 June 2025

SEASON 1, EPISODE 29

Show Notes

In this episode, she exposes why most startup founders get ghosted by VCs (hint: it’s not your pitch deck), shares the brutal math behind venture funding (1,000 deals reviewed, only 1-3 funded), and reveals exactly what she looks for beyond the typical metrics.

Plus, she drops game-changing advice on how students are breaking into VC right now without connections or trust funds – including the “shadow portfolio” strategy that’s getting MBAs hired.

If you’re interested in VC, micro-investing as an Angel investor, or working at a women-led start-up — this is your episode as Dawn will give you the inside scoop.

Key Points From This Episode
  • Dawn spent 30 years as an operator running companies, including transforming Old Navy from a startup with less than $1M in sales to an $8 billion company, before transitioning to venture capital.
  • Only 7% of venture capital check writers are male, with less than 3% of funding going to all-female founding teams and only 2% of healthcare funding directed toward women’s health.
  • Women invest in venture capital at half the rate of men, largely due to structural barriers including high minimum investments ($500K-$2M) and lack of access to information about the asset class.
  • Capital F Fund has over 70% female investors, which is virtually unheard of in venture capital and creates a powerful mentorship network for portfolio companies.
  • The fund focuses on three areas where technology shapes women’s lives: women’s health, digital commerce, and AI enablement, specifically targeting companies with valuations under $12 million.
  • Dawn emphasizes that venture funding is extremely selective – they review about 1,000 deals annually and invest in only 1-3, meaning rejection doesn’t reflect on the business quality.
  • Key investment criteria include emotional resilience and ability to take feedback, as startups face constant challenges and founders must remain open to new ideas and counsel.
  • Archive Resale, a portfolio company enabling brands to host resale on their websites, exemplifies the “triple threat” of female founder, climate impact, and tech growth potential.
  • Women’s health investments include Hey Jane (telehealth abortion care), Stardust (period tracking app designed by women), and Zella Health (AI-powered reproductive health diagnostics).
  • For those seeking venture capital careers, Dawn recommends building a track record through shadow portfolios or small angel investments and developing deal flow by networking with founders.
  • Studies show boys raised by working mothers are more likely to succeed professionally, and representation matters for broadening opportunities for future generations.
  • Dawn believes wealthy women use their resources differently than men, focusing more on systemic impact rather than luxury purchases, making wealth distribution to women particularly powerful.

Quotes

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Links Mentioned in Today’s Episode

Capital F Fund
The Council
Archive Resale
Forerunner Ventures

Transcription

Dawn: [00:00:00] I’m a capitalist and I am investing in women and around women and around female experience and bringing female investors into our fund because I believe that wealth in the hands of women is great.

Georgi: Did you know the average person will work 90,000 hours in their lifetime? What if you could use those hours to find fulfillment and become a disruptor for good?

Georgi: Welcome to the work That’s Worth It. Podcast. I’m Georgi Enthoven, and I’m here to demonstrate that an ambitious, meaningful, and rewarding career is not just a dream. It’s achievable. Each episode will dive into conversations with global change makers who crack the code on combining income and impact. If you’ve ever felt like you were torn between a paycheck and your purpose, or maybe you simply yearn for more purpose, you’re going to be exposed.

Georgi: To the ambitious humans who have done it themselves, ready to make your work worth it. Let’s get started[00:01:00]

Georgi: Today. I am excited to have Dawn Dobras on the show, and her story is exactly what work that’s worth. It is all about building a career that combines meaningful impact with an income to make it worth your time and energy. Dawn shares with us that even as a young kid, she wanted to be a CEO, and she meant it early on in her career.

Georgi: She was one of the early employees at Old Navy when it was just a tiny startup with less than a million in sales. By the time she left, she helped build it into an $8 billion company. Talk about being able to pick winners. No wonder she’s now in venture capital. After 30 years as a C-level executive and CEO, most recently leading Credo Beauty, which fast company named the world’s most innovative beauty company, Dawn Co-founded Capital F, where she’s flipping the script on who gets funded in venture capital.

Georgi: If you have been following [00:02:00] along on my weekly podcast episodes, you will have noticed that I like talking to venture capitalists and here’s why. First, they bring a unique specialty and perspective on where the future is headed, especially in their knowledge. Area of interest, whether it’s Latin America, ed tech, climate solutions, or woman-led businesses.

Georgi: Second, often the closer you get to the source of capital, the more money you get to make. And on this show, I want you to see opportunities that include both income and impact, not just one or the other. And third, if you look at their portfolio companies, it’s actually a fast way to discover interesting entrepreneurial environments where you might want to work to gain startup experience.

Georgi: Dawn’s fund is 70% female investors and invests 90% in female founders. She’s literally changing who has access to capital while generating serious returns. And stick around to the end because she shares some [00:03:00] brilliant unconventional tactics that students are using right now to break into the VC world, plus a secret weapon for finding job opportunities that most people completely overlook.

Georgi: I. Hi, Dawn. It’s really great to have you on the work that’s worth the podcast. Georgi, thank you so much for having me. I’m excited to be

Dawn: here.

Georgi: Yeah. Well, I am really excited to hear more about what you have been doing for work, and I wanted just to jump into what originally drew you to venture capital and specifically investing

Dawn: So if you had asked me 10 years ago, or even at the beginning of my career path, I would’ve never guessed that I would be here now. So I feel quite grateful that I’m here and it’s only the summation of many twists and turns of my life that let me be here. Now

Georgi: let’s talk about some

Dawn: of those. Yeah. Yeah. So by way of introduction, I spent the last 30 years running companies, and I was the fourth grade kid that told her parents that she wanted to be a CEO, which is kind of nerdy, and they were kind of like, [00:04:00] okay.

Dawn: And when I went to business school, I was very much interested, which was very out of favor in going into operating and running companies. So the majority of my classmates, I went to Harvard Business School, wanted to go straight into consulting. That’s where the money was, or into iBanking. And I was very much, I wanna go into startups, I wanna go into companies that make things.

Dawn: And I was particularly interested in fashion design, beauty, again, not your traditional MBA path. When I rolled outta business school, I started at a company that was a very small startup. There were, it was less than a million in sales, maybe, I don’t know, 10, 15 of us there. And that company ended up being Old Navy, and by the time I left, it was an $8 billion company and I’d had tons and tons of roles.

Dawn: I share this ’cause that’s part of my story of getting into venture. Really early in my career, I got to be in a high growth startup that turned into a huge company, obviously more than a unicorn. I got my hands on lots of stuff in kind of crazy [00:05:00] times. I look back and I’m like, I can’t believe they let me do that.

Dawn: That launched me into a series of roles, increasing importance of kind of C-level roles in private equity turnarounds. I did startups. I was in a startup that got sold in four years to a publicly traded company. I most recently was the CEO of Credo Beauty, which is. The largest clean beauty retailer in the US and has lots of fans out there, and if you’re one of ’em, go shop there.

Dawn: We love that store and through those series of experiences and increasing responsibility, I think somewhat naively, I assumed that there were just gonna be more women at the top. And I don’t know why I thought that, and I just was too busy raising my family and being an operator and running companies that I didn’t spend a ton of time thinking about it.

Dawn: And increasingly, when I got to the top, I would be the only other female, CEO in the portfolio, or my board would be all male or increasingly, [00:06:00] my investor table would be all male and. It didn’t feel right, to be honest. And when I rolled outta my last CEO role, I had been angel investing and continued to see this gap in the market.

Dawn: And there’s lots of stats and I can go through it, but 93% of check writers in the venture industry are mail. Um, when you look at total funding to healthcare, only 2% goes to women’s healthcare. There are different stats around funding to female founders. All female teams, less than 3%. Mixed teams are around 21 to 25%.

Dawn: That means one male founder or with one female founder. Saying it in the reverse feels kind of shocking though, that 98% of founding teams are all male. 70% of founding teams do not have a female on there, so pretty shocking where 51% of the population, 85% of consumer spend. And so I’m circling back [00:07:00] to like what drew me to all this.

Dawn: Yeah. It was a lifelong journey of experiences of being in the hot seat, of seeing where funding came and also seeing a lot of opportunity. Yeah, great way to make money about investing in and around the female experience, and that’s what led me to capital F.

Georgi: That’s such an interesting story and it sounds like you had some really interesting and early successes and that almost has allowed you to take on a bigger mission in this stage of your career where it’s not necessarily the easiest or the most glamorous role, but it’s something that you can do, which really changes an ecosystem.

Dawn: Yeah, I mean, to be clear, I’m a capitalist and I am investing in women and around women and around female experience and bringing female investors into our fund because I believe that wealth in the hands of women is great and by and [00:08:00] large when you look at. I’ll just say super wealthy women, whether that’s self-made or inherited, they do different things with their money than the men do, and they don’t buy rockets or big boats or trophy wives.

Dawn: They actually do a lot with impact and you know, I’m really inspired and moved by folks like. Melinda French Gates and McKenzie Scott and Lauren Powell jobs. These are women that are like making systemic change with their wealth. So

Georgi: you’re motivated to get more women? Yeah, I’m

Dawn: motivated to get more wealth into women’s hands.

Dawn: Yeah, and I think that they can do really interesting things with that.

Georgi: Well, let me ask you a question. Obviously we know systemically women are held back, but are women holding themselves back as well? So my

Dawn: answer is no. I do think that there are examples where, by the way, we were raised by the patriarchy that we are less likely to pursue experiences.

Dawn: And so all you just use [00:09:00] an example of venture capital men invest in the venture capital asset class at twice the rate that women do. Now, why is that? And I think about my own self, like I went to Harvard Business School, I was A CEO, I’m quite successful. And I had never invested in venture. I didn’t even think I didn’t know about it, but so interesting.

Dawn: Now that I’m on the other side. Number one, the guys are all doing it. And as an asset class, it doesn’t mean it’s appropriate for everybody, but if you do have a portfolio construction, you are likely to wanna consider high risk, high reward asset class as part of your portfolio. And women for a variety of reasons, both structural and also confidence level are not.

Dawn: So I’ll talk, they’re, they’re not high risk, high reward. There’s a couple things. One is structural. So the way that, and I didn’t know any of this, so I’m just gonna share my own learning experience. Yeah. The way that venture funds are structured is that they’re limited to 99 investors. And so when you think about a hundred million dollars [00:10:00] fund and you divide that by 99.

Dawn: You get a million dollars, so I’ll just use that as rough money. So the minimum ticket size to get in most venture funds is around a million dollars, sometimes 2 million, sometimes 500,000. Well, most women, number one, even if they do have a million dollars, they have not been introduced to the asset class and they may not have the knowledge or confidence to engage at that level.

Dawn: So simply by the ticket size you are. Less likely to engage. So I don’t know that I’m calling that women holding themselves back. I think there’s an information gap and perhaps an access gap. The second piece of it is that venture funds are historically hard to access and very, like I was playing golf, I.

Dawn: And that you are accessed that way. And so it is not a very democratic process about how you even get into a fund. So it is not surprising that women are underrepresented as investors in this asset class. Now we can change that. You [00:11:00] can ask questions, and actually, as part of our fund, we have done a series of salons across the United States just encouraging women to learn more about venture.

Dawn: We are not the only ones. There are many great funds out there. However, what’s a capital call? How is capital called? What does that mean? What should you expect in terms of your liquidity? What should you expect as terms of returns? How do you access this information? Just like the basics so that you can actually even make a decision whether that’s.

Dawn: An appropriate asset class.

Georgi: Yeah, so interesting ’cause thinking about your role is when you normally think of venture capital, you’re thinking of you raising funds and investing in companies, but you’re actually trying to change a system behind it. And that probably taking a good portion of your time and energy is to introduce people even to what investing would be.

Dawn: Yes and no. It is part of what we consider important to our fund. So we are proud to say that over 70% of our fund [00:12:00] is from female investors. That is unheard of in venture, unheard of. There are a handful of other funds that can make that claim, but hardly any. Um, we feel really proud about that. I will also say there is a method to our madness in that we have found that the cohort of women that are interested in venture capital around what we’re investing are former operators or folks that have worked in industry and have not had this opportunity or didn’t understand the opportunity.

Dawn: They’re great mentors and coaches for all of our founders, and as they get involved, as either advisors, board members, or just sounding boards, our founders’ lives are enriched mentors, whatever it is. And so we have this really awesome loop of bringing women in and then having them actually enrich grow, help our founders.

Dawn: Be more successful. Yeah. So to us it’s the secret sauce. But yeah, it is definitely a different approach. And it’s not on the golf course.

Georgi: Yeah. Okay. [00:13:00] So let’s switch gears to you looking for your investments in these women-led companies. What are some key signals you look for beyond the pitch deck, or who are the types of women and the companies that you are looking and interested in?

Dawn: Yeah, so I will back up a little bit and just give some of the math around venture. I didn’t understand this when I was raising money from venture capitalists. Just on average, we look at about a thousand deals a year. So on any given quarter, that’s two 50 deals. We go into due diligence on roughly 10 of them with the intention of investing in one to three.

Dawn: I share that because that’s a pretty extreme pipeline, and I. It means that there are lots of worthy people out there that we are not funding. And so I think I didn’t fully understand the math and when I would get ghosted or not, I would be like, my pitch must have been bad or This business isn’t valid.

Dawn: And that is not the point. The point is it’s [00:14:00] very extreme and narrow funding, and I often counsel first time founders to build a friends and family round before you seek venture because it’s such an extreme path. So I share that by like the numbers are quite, everything needs to line up. I did not understand that.

Dawn: We look in three big buckets. We look at where technology shapes women’s lives. So we look in women’s health, we look in digital commerce, and we look in AI enablement. We are curious about where women spend time, money, and energy. So the broadest level is. Are you in one of those buckets? The second piece, and again I will reiterate this ’cause I don’t think I understood this when I was raising money, is we invest at a very specific stage with a very certain criteria.

Dawn: So for us it’s valuations under 12 million and we’re looking at. Five to 7% ownership. So there’s some math behind it, but that is a very, if you’re outside of that, we’re not gonna consider you. Okay. And that’s just because that’s our [00:15:00] model.

Georgi: And do most funds, like if you were trying to raise money, do most funds make that information transparent?

Dawn: It’s pretty opaque. It’s pretty opaque. And so I think hard think if you are a female founder and you’re not raising, remember, the venture capitalist job is to meet as many founders as they can because they’re collecting data. Maybe that’ll lead to something. It does not mean that they’re. Think that you’re appropriate for their fund.

Dawn: I did not understand that. I’m like, I got a meeting. Look at me. Yeah. And like that has no correlation. And so you can ask, and I didn’t understand that power dynamic. Yeah. I should have asked and I now understand, Hey, are we even in your buy box? I. Are we even a fit for what you do? Like you need to ask that.

Dawn: Are you deploying capital? Lots of people take meetings when they don’t even have money to deploy. You deserve to know do they have money and are you even in the realm of possibility? Yeah, I didn’t know that

Georgi: because they have to fill their pipeline and are gonna fill it. Anyway, but it’s more noise than actual being serious about

Dawn: making a adjustment.

Dawn: It’s a lot. You’re running a company and you’re learning, and [00:16:00] so I think these are things that get passed on from founders, and if the majority of founders are in one cohort and Europe, we’re not part of that, some of this informal knowledge doesn’t get passed on. There are other people out there, great podcasts out there that you can learn this, but I didn’t know that, so I’m just sharing what I learned.

Dawn: So, broad bucket, are you in the right stage? And then we really start to like competitive. Do we believe in this? What does the team look like? You know, I would say kind of traditional paths. I think there is a false understanding that you need a perfect deck. We’ve invested in companies that have been free revenue with bad decks, and.

Dawn: It’s the idea and it’s the team. So we do that. And then for us, we’re former operators. We are less of the type of investors that are looking for, I don’t know, spaceships on Mars or underwater, or kind of like deep science. We’re pretty practical. We wanna know how you make money, what your margins are, how you’re gonna exit the [00:17:00] practicalities of a real business.

Dawn: And then I would say the last stage for us is really about emotional resiliency and ability to take feedback. Tell us more about that. Yeah, so one thing that we’ve both learned, my partner’s also an operator, is that I. Startups, you’re gonna have a bunch of things go wrong. Like most things go wrong, hardly anything goes right.

Dawn: Actually, you might break up with your co-founders, you might run outta money. Your biggest client, like there’s a lot of stuff ahead of you. And the folks that we see thrive in that are the ones that are I. Open to new ideas along the way, and so we push quite hard on that. So we might push you on an idea.

Dawn: And our goal of that is not to have you agree with us. We’re not always right. We could be totally wrong to be honest, but we’re interested in your reaction. What we’d love to hear you say is, wow, we’ve never considered that. Let me dig into it and see if that makes sense. Or, my gut reaction is, I don’t agree with that, but I’d like to dig in [00:18:00] or, that seems really interesting.

Dawn: Let me take it back to the team and engage. We’re looking for the ability to engage. And not always be right because that will serve you well on this long journey. Okay. And when we encounter someone who’s super rigid or like I have to be, right? We know that that’s not gonna go very well.

Georgi: Yeah. So when you give feedback, you want it to actually be able to go deeper and sink in versus just bounce back a response immediately.

Dawn: Mm-hmm.

Georgi: Yeah. Yeah.

Dawn: And that does not mean that we’re right. And yeah, it’s more about you just have questions. It’s more about we’re testing for like, can you listen? Will you seek counsel? Are you gonna go it alone or are there other people that are gonna help you? We’re kind of testing for that and then we always meet in person.

Dawn: We will invest unless we spend time with you.

Georgi: Can you give us some examples of the companies that you’ve invested in and that you think are great opportunities for young people looking for entrepreneurial environments?

Dawn: So I’m gonna highlight one that’s called [00:19:00] Archive Resale. You probably have already encountered it, so if you go to any major brand and you see a secondhand or a pre loved or a resale portion of it, so you could see that on Lululemon, on North Face, on ikea.

Dawn: You know, hundreds of brands have that. This is the technology layer that allows brands to host resale on their website. Female Founder out of Stanford Business School, Emily’s amazing. And her co-founder Ryan, my partner Margaret, wrote their very first check into there. And so, um, they just went through their series B at a very high valuation.

Dawn: And, you know, venture works when you get in early, like it’s quite extraordinary about the returns you can get. There’s some other things that I love about this. Number one, having run retail companies, the way you acquire customers is increasingly expensive. So I love the fact that through resale you can open up access to different customers.

Dawn: For instance, my kids love North Face. I. On their very early [00:20:00] right out of school salaries. That’s probably not in their budget all the time, but they can buy resale, so they bring new customers in. Secondly, it engages existing customers. So there’s a brand that I love called ULA Johnson, very bold, interesting prints.

Dawn: I kind of like to get a dress every year, but they’re really, you know. Expensive. So I just resale ’em. So every year I buy a dress, a new summer dress, and then I resale it on the other side. So it keeps me engaged as a customer. And then lastly, like obviously a landfill is a huge problem. Apparel, shoes, footwear are the leading contributor to most landfill.

Dawn: And the idea that we could take a portion of that and keep it engaged in our ecosystem more is just an incredible one.

Georgi: Yeah, it’s win all the way round. Yeah,

Dawn: so we always say that they’re a triple threat because female founder, global, like climate impact as well as tech rocket ship, we’re like, wow, we hit the big time with them.

Georgi: I know you are also interested in some health tech [00:21:00] ventures. Can you share some information about what’s interesting in that sector and also maybe highlight a company or two.

Dawn: Yeah, so health right now is incredibly interesting and I would say women’s health is even more interesting. We have a number of women’s health companies in our portfolio, so I’ll highlight, Hey Jane, which is the leading telehealth provider of abortion care.

Dawn: Incredible founder. I could talk this entire podcast about how much. I appreciate Kiki and her ability to run a plus $10 million business under extreme governmental pressure like rocket ship under the tough circumstances. Another one is called Stardust. Stardust is a women’s health tracking app. Um, start as a period app.

Dawn: If you haven’t tried it, you. It is the first women’s health period tracker that was designed by a woman, and you will immediately know once you log on. And my hunch is that there’s a a lot of amazing, maybe some of your listeners have already signed on. ’cause [00:22:00] when I say that many people light up, we’re also investors in a company called Zilla Health, which is a diagnostic platform for women’s reproductive health.

Dawn: So it’s leveraging menstrual fluid. And ai. So to analyze that, to provide one of the first diagnostic for endometriosis, PCOS, and more broadly, giving you a sense about your biological age versus your reproductive age, which are very different. And you could be a healthy 3-year-old, but have an aged reproductive system that might cause you to make different life decisions, freezing eggs, in vitro, whatever it is.

Dawn: And we’re pretty excited about what that unlocks for women.

Georgi: I love these examples and how they touch women at different cycles, but I think most women would relate to them. And I want to just highlight that if you are a young professional and women is something that you want to focus on in your career, one of the interesting ways to find [00:23:00] companies that match your value system.

Georgi: Or you know, the contribution you want to make in the world and partner with a company to do that is to look at a venture fund like yours, yours, which has the focus on women, and then look at the portfolio companies and see who they’re investing in. And those are really interesting opportunities for that startup world.

Georgi: George,

Dawn: I couldn’t agree more, and I’ll just take it one step further. Yeah. Most all of them have newsletters, sign up for their newsletters and just about everybody publishes open roles. So if it is something interesting, go to those VC sites that you’re interested in, look at their portfolio companies, sign up for their newsletters, and then once the VC

Georgi: newsletter,

Dawn: DC newsletter.

Georgi: Okay. Okay. Yeah. So

Dawn: for instance, I’m a huge fan of forerunner. Big VC firm out in the market started by women and they have a great newsletter and they always publish their open roles like they’re the backers behind Aura Among a gazillion. Other things, [00:24:00] like hugely successful female venture firm. They always have maybe 40 open roles every week on there, so there’s, it’s a great way to look for jobs.

Georgi: Okay. Really interesting way, instead of looking at a job board, then searching through and having to figure out, yeah, look at

Dawn: job boards and don’t think LinkedIn is gonna help you.

Georgi: Yeah. Now, I’d love to hear any advice you have for young people interested in the startup world, and it sounds like you, you know, definitely were able to do that at Old Navy and what kind of companies or what should they look be looking for in companies and founders?

Dawn: I always say to look for two things. Put yourself in a growth area, like very difficult to get ahead if the company is shrinking or staying flat. So if you’re young, you wanna move fast, you wanna get promoted, like you don’t wanna be in a slow growth company. So I always look for growth and then when you can.

Dawn: So growth would be my first criteria. The second criteria would be align yourself with someone that you respect, and that doesn’t necessarily [00:25:00] be mean. Your boss. I’ve had a lot of shitty bosses along the way, but to the best of your ability, align yourself with people that you respect in the industry or in the company.

Dawn: And that could be as simple as asking them out for a coffee. That could be, this does not have to be formal mentorship. This just has to be someone who likes you or that you can get to know and ask them questions and be a sounding board. And those two things I think can really help pull you through.

Georgi: Yeah, I love that advice. When I was at Harvard Business School, I had a professor in the entrepreneurship class that said, you wanna make sure that you are riding the horse worth riding and a race worth winning. And it sounds like that is sort of what you’re saying. I think that’s

Dawn: a much better way of saying it, which is probably why she or he is a Harvard school professor.

Dawn: Yes, yes. I do wanna say that I, I get approached a lot about like, can I be either your mentor or things like that. And I know there is a formal mentorship. I would say that the, [00:26:00] everyone in my life that has been impactful has been informal. And so I would not over index that. You need like a formal mentor.

Dawn: Formal mentor,

Georgi: yeah. Yeah.

Dawn: It’s just people that are in your ecosystem that you can, and they can be sounding boards along your journey.

Georgi: I in my bookwork, that’s worth it. I have a chapter on connections and I talk about the safety net and the trampoline and how important those are for people like yourself who have been able to excel in the work that you do.

Georgi: And the trampoline could even be somebody you read about. It’s like somebody who you can stand on their shoulders and take something further because of what they have done. But it definitely, like you said, it doesn’t need to be a formal relationship. Georgi, I

Dawn: like that trampoline and safety net. I’m gonna pick up all these phrases and start using them, but I’ll credit you, don’t you worry.

Dawn: Yeah.

Georgi: Thank you. Well, I also want your advice or opinion on people who want to get into venture capital and what stage in the career you think it’s the right time to do that. Because I talk [00:27:00] to a lot of young people and they want to go straight into venture capital out of college, and I would love your thoughts on what you would think would be the best path for setting up for success for a venture capital career.

Dawn: That’s a great question, and obviously I did it at the end of my career, but I see a lot of people at the beginnings of their career too. I would just say, look, it’s hard to get into, so just know that there’s not that many jobs out there, and so I wouldn’t say be super discouraged. The first thing, build up your own portfolio.

Dawn: So not everybody has the capital or the equity to do that, so it can even be a shadow portfolio.

Georgi: Can you tell us what the shadow portfolio is? Yeah.

Dawn: So you could say, you know, I know that this deal is happening. I am going to track this company and put in 10 K and see where it goes and I’m gonna track it over five years.

Dawn: So just think from the VC side, I’m looking for someone that has good investing sense. I, the best way to show me that is a track record. So the first [00:28:00] thing is show me that you can pick things. Now, I don’t care how much money it’s, I. What I care about is that you can pick so shadow, or if you have $10,000 and you can put $500 in different companies, like I am looking for the ability that you have the, that you know how to pick things.

Dawn: So there’s lots of ways to create that, and there’s lots of angel groups. I can recommend a lot of ’em. But get involved with an angel group, start to learn how to do diligence, and most importantly, start your track Record venture is a 10 year horizon, and so don’t wait until you have my, you know.

Dawn: Significant money to do it. Start now. Second thing, I’m looking for deal flow. I wanna know that you’re friends with lots of founders and I can, I actually am working with somebody at HBS right now who’s trying to get into venture, and he sends me a quarterly update of all of his classmates and what ventures they’re doing and that he’s interviewed them.

Dawn: And here are the two that he thinks I should meet. [00:29:00] Well, I’m telling you, he’s already doing kind of the job of a venture associate and so. He’s gonna get a job because he has, I’ll just say deal flow or pipeline.

Georgi: Yeah. He’s showing you that he has the skills versus telling you.

Dawn: Right. And I, I’ll just say for the record, he’s diverse.

Dawn: He is not part of the establishment and he’s like making his own way. So he’s making some small angel investments. So he is demonstrating that he can pick and he is demonstrating that he has deal flow. Those things you can do in college, you can do them in business school. It’s just being part of the thing.

Dawn: And you can do that by signing up for conferences or going to mixers, talking to your classmates like this is not hard to do. You just need to be in the flow. I. I’m not gonna hire somebody that’s not in the flow on those two things. I have another, she’s a TI Stanford undergrad who wants to be in venture.

Dawn: She started her own podcast and she started reaching out to female founders and just interviews them. And you know what? That’s another way of deal flow. The female founders are talking to her and she’s always [00:30:00] sending me new ones. She’s a junior at Stanford, like. I have another, I would say, recent graduate from UCLA who kind of blew up on social media and she’s just making commentary out there on Instagram and TikTok about female founders and venture.

Dawn: There’s a lot of ways to get in there, but you’re not gonna just like roll in.

Georgi: Yeah, so I love what you’ve just shared ’cause really practical ways that people can authentically show that they’re interested in what they’re doing and it’s not for the accolades or that you’ve reached this place, but they’re actually genuinely interested and can be of value right from the start.

Dawn: I. Yeah, I mean like look, if your dad is a big venture guy and you grew up knowing all those people, my hunch is it’s gonna be easy for you. I’m trying to talk to everybody else.

Georgi: Yeah. Yeah. Now, I wonder if we can just have a personal question, but when we talked offline before, you said you are raising boys and investing in women, and [00:31:00] obviously there’s a lot of talk about boys getting left behind and struggling right now, and just want your thoughts on.

Georgi: How you settle that within yourself and how you keep your focus on women?

Dawn: Such a great question. I mean, I just listened to the podcast with Scott Galloway and Gavin Newsom, if you hadn’t heard it, it goes into really this generation of 20 year olds and like the gender divide. And I actually had my kids listen to it too.

Dawn: It resonated deeply with what I’m seeing, and it resonated with them too. I, I particularly like that podcast because there are a lot of specific policy changes that I think are important. It is a very interesting time for raising boys. What the studies would show is that boys raised by a working mom in a professional sense are much more likely to be successful in professional careers.

Dawn: And so I share that just because if you are raising boys or if you’re raising kids right now, there’s a lot of mom guilt associated with [00:32:00] working and being outside the home. And I would suggest, and I can’t say this for everyone, but from my own personal experience, what I’ve seen, you’re actually building really resilient kids.

Dawn: Regardless of gender. So working successfully outside the home demonstrating that, you know, value worth and productivity are important to you as a value and as a family value are soaking in regardless of whether those little plants are respectful or nice or acknowledgement to you. So I think that’s particularly important.

Dawn: And I can point out that all of our kids always had summer jobs that they always had to pay for things. You know, we really believe in that. I do believe that there is a gender gap right now with boys in particular, and we talk about in our family a lot of the harmful, like the video game playing, the zis, the lack of socialization.

Dawn: And I don’t necessarily have all the answers. I can only say what we try and do in our home is like, you need to ask her out on [00:33:00] a date, you know, in our, in our case or you need to be out there and being social and you know, pretty taking initiative. Yeah, taking an initiative and being very social. I think we, we really emphasize on the social side

Georgi: side.

Georgi: Yeah. We’re almost outta time and I want to lo you one lofty question. What makes your work worth it for you at this stage in your career?

Dawn: I’ll circle back to Emily, who is the founder of Archive Resale, which we spoke about earlier. And like I said, she’s a triple threat or that company’s a triple threat and I can’t tell you how proud I was that we were investors in her and I.

Dawn: Part of New York Climate Week, they actually put her on a billboard in Times Square and to see her standing below that and see her picture in Times Square and think that we were part of that journey was just so immensely satisfying and that we’re returning capital. God, I don’t know. It felt so powerful.

Georgi: Yeah. So the income and the impact is combined [00:34:00] and you really do have, be able to benefit from both.

Dawn: Yeah, and also just to see a female CEO at that age, just crushing it. Each of those moments make the path wider for everybody else behind it. So you need to see something. I believe in representation is a big deal.

Dawn: I needed to see female CEOs ahead of me. I need to see female venture capitalists ahead of me, and to see Emily just crushing it in the climate space, like she’s broadening the road behind her. So like that’s how change gets made.

Georgi: Yeah. What a beautiful way to end. Thank you so much for sharing everything that you have shared with us on the podcast, and it’s just really lovely to have you as somebody in my network.

Georgi: I really appreciate it. Right back at you trampoline. Back to you trampoline. Yeah. Thank you so much and we’ll be in touch. Thank you. This episode was jam packed with so many nuggets, but for now, I want to highlight a couple points. First, for the entrepreneurs out there looking for funding, Dawn shared with [00:35:00] us many stats to give us more insight into the world of vc.

Georgi: As she shared, she looks at a thousand deals a year and only invests in one to three. Most VCs take meetings even when they have no money to deploy or you’re completely outside their criteria. Before you waste months of perfecting your pitch deck, ask the hard questions. Do they have capital to deploy right now?

Georgi: And are we even in your investment criteria? You should ask. Otherwise, they’re collecting data on your time. Second, for those who want to break into vc, this is a particularly interesting episode. I really appreciated how Dawn gave so many detailed examples that make VC seem more tangible. Dawn wants to see two things.

Georgi: Proof that you can pick winners and evidence that you can get deal flow. Therefore, if VC or impact investing is of interest to you, start a [00:36:00] shadow portfolio tracking companies. Join Angel groups with small amounts and interview founders for a podcast or just to build your network. You can demonstrate VC skills from your dorm room, but only if you start building your track record now.

Georgi: Not after you graduate. And that’s a wrap for today’s episode of Work That’s Worth it. Remember, every conversation we share is designed to empower you to build a career that’s truly worth your time and energy. There are future disruptors out there just like you, who would appreciate the conversations in this podcast.

Georgi: Please support me by spreading the word and sharing this episode with a friend or two, or visit my website@georgienthoven.com. That’s spelled. G-E-O-R-G-I-E-N-T-H-O-V-E_N.com. Until next time, ask yourself, what problems am I solving and are they worth my valuable time? Your intentional choices today can lead to exponential impact tomorrow.[00:37:00]

Georgi: Thanks for listening.

Meet Georgi Enthoven

As the visionary founder of Work That’s Worth It, Georgi specializes in unearthing the unique inspiration and career desires of those seeking significance both for themselves and for the world.