Investor at Red Beard Ventures Elana Dickman on her Path into Venture | Seed To Harvest Ep38

Welcome back to Seed to Harvest, a podcast with founders, creators, and investors about their stories, frameworks, and tactics. My name's Paige Finn Doherty, and I'm a founding partner behind Genius Ventures, as well as author of an illustrated children's book about venture, Seed to Harvest. Today I'm joined by my good friend Ilana Dickman, who's an investor at Redbeard Ventures. She started her career at top consulting firms such as KPMG and Deloitte. She's built a reputation for herself as a content creator with her podcast, The Girls' Table, as well as an angel and NFT investor. Alana, welcome to the pod. I'm so excited to have you on.

I am so excited to be on, Paige. Thanks so much for having me.

Of course. Okay, so we were chatting like a bit before the show, but we both run our podcasts, and I wanted to start with some fun questions. The first would be, what book What book do you think impacted your trajectory most as a young adult? And it can be a fiction book, it doesn't have to be a business book. It can be, that's pretty common.

Yeah. I'll let you take it away. I'll do 2 books. So the first one was Power of Habit. I was actually living in Australia during COVID and I was really on kind of my personal growth journey. And I think it really helped me look at my life and be like, what habits do I currently have in my life that are both good good and bad, and it made me question my surroundings and what I was doing. So that really just affected me, and I think I still utilize it today, like working out in the morning. Like, that's a habit. And I think in the beginning it's so hard. Like, I hate waking up early, and then you kind of get used to it and it helps you grow. So that's one. And then the other one is going to be Ready Player One. I'm not sure if you've read the book or watched the movie. No, I haven't.

I've been recommended to. Yeah, tell me more about it.

I think it's just one of the best sci-fi books, and I'm like not the biggest sci-fi reader. I think I've been lately, and I think that one just really helped me see kind of a different perspective in terms of gaming and just the future, and I would highly recommend it to anybody.

I love that. I too have been getting into science fiction recently. I read The Name of the Wind, and if you're into gaming books specifically, I really enjoyed The Culture Series by Iain Banks. It's really interesting about a post-scarcity society and where they just follow their deepest passions as, as far as possible, cuz they don't have to like worry about success or money or whatever. And it's all about this guy who's just like incredible at games. So if you enjoyed Ready Player One, I feel like that would be— Player of Games would be a good one to check out. Also, what I wanna hear more about Australia. That sounds awesome. What, how long were you there for? And you're based in LA now, right?

Yes. So I was living in New York working at KPMG Consulting, and basically I always wanted to go to Australia. My client was Avis Car Rentals and we were doing an engagement in Australia and I was an associate at the time. I wrote a 26-page proposal deck for why they should send an associate to Australia with no supervision. I should just be there. And they approved it and they were gonna send me. And, uh, about 2 weeks before I was supposed to go, all these tax implications came up and they were like, we can't send you. You could wait around, see what happens.

No.

Or like take a sabbatical or quit. And I was like, you know what? I am, I think at the time I was 22, 23. I was like, I'm quitting. I'm moving to Australia without a job. And so I quit, I moved there with my best friend, and I had no job. And I messaged everybody in the world to get a job, like LinkedIn. You probably got a message from me. Like, I really messaged every person who basically lived in Australia. And then finally I messaged the CFO of Deloitte Australia being like, I just moved here, I'm looking for a job. And he introduced me to a partner and I ended up working for Deloitte Australia, like right before COVID to after COVID for a year.

Mm-hmm.

It was an awesome experience. If you've never been to Australia, it is one of my favorite places in the world. But my work-life balance was the best and it really just helped me focus on other aspects of my life. Like I did dropshipping on the side, I was investing on the side. It was a lot better than what New York was where I was working crazy hours. Like I had way too much time and it was the best experience for my personal growth.

That's so fun. It's funny as well that you continued in your Like a similar career trajectory, but just changing the context that you were conducting it in radically changed like your life and your habits and like enabled you to build a, a better work-life balance. That's super cool. I would, I would love to talk more about your transition from consulting to venture as well. So if you could walk me through if there was any key decisions or Kind of like, oh shoot moments. Would love to hear more about that.

Yeah, so I've been investing in the public stock market and crypto for a couple years. At the time of working in consulting, I would always talk to my colleagues about it, what they were investing in. It was kind of always a side passion. And then I switched to a startup after Australia in LA. So I worked for this company called Flowcast, actually completely did career switch to tech sales, but on the side I was looking and subscribing to different syndicates. So the syndicates would send me different startups. I'd look at what they were building, and I started just investing in different companies. One specifically I always followed, their name's HyperGwap. And so I invested in SpaceX and Rainbow and Alt and Atoms, and I started just getting a startup portfolio. And then I got really deep down just the Web3 crypto rabbit hole. So got my first NFT, then started investing, started becoming a content creator and kind of an advocate for women in the space. And then I went to NFT New York City last year and met Drew Austin and started sourcing deals for him specifically in the Web3 crypto space. So then he brought me on full-time to help run the fund and syndicate as well.

That's awesome. And then to give our listeners some context, who is Drew Austin and can you speak more about Red Beard Ventures as a, as a whole as well?

Yeah, for sure. So Drew is the managing and founding partner of Red Beard Ventures. It started about 2 years ago. The first investment was SuperRare. Since then, we've done now almost 200 investments through a syndicate. So we've invested in Sandbox, Dapper Labs, Wilder World, Unstoppable Domains, and yeah, as I mentioned, about 150, 200 others. And then earlier this year, we started raising a fund. So we're raising a specific to Web3 crypto fund right now, pre-seed to Series A. But yeah, Drew comes from just a founding background. He started an HR recruiting platform. He's a really big advocate in the Web3 crypto space, started an NFT project, and has been investing in the top Web3 crypto companies.

Hmm. I'm, I'm curious, when you, when you look at a Web3 company or any company in specific, what are the key characteristics that you're looking for in a company that you'd consider adding to your portfolio?

Yeah, so the first, as most people would say, is always gonna be the founders. So what was their background? What have they done? Why are they kind of the perfect fit to actually make this company successful. A lot of times we're pre-seed to Series A, but kind of the sweet spot that I look for is more that seed. So what's their traction right now? Do they have a product market fit? Who are their competitors in the space? How are they differentiating themselves? And then I'm looking for the companies that are the infrastructure behind Web3. So one of our biggest investments right now has been Zero Tech. It's the founders of Wilder World. They're absolutely insanely smart and they're doing end-to-end DAO infrastructure and that to me, 'cause I feel like what's gonna help really build the next generation of Web3. I think a lot of times people ask me, they're like, what NFT project are you investing in? What are you doing? I'm like, no, I truly believe in the infrastructure. What's gonna help the next 100 million people join crypto and Web3, but not necessarily, oh, what animal NFT project is gonna be successful in this space.

That's awesome. And, and you mentioned earlier that you like becoming a content creator has also been a big part of your path into venture. I would love For you to talk about more, like what mediums do you create content in and then how has that supplemented your investing practice?

Yeah, so I'm under Trading Female on Twitter and The Trading Female on Instagram, and that's where I started. I started actually posting pictures with my NFT in real life, and that's how I at first got my following. And then from there, I just really just started being an advocate for women, trying to bring more women into the space. So I started The Girls Table, which is to have meaningful conversations both virtually through a podcast and then IRL at different conferences. I've hosted different brunches and dinners. But the main platform that's helped me the most in terms of venture is Trading Female, because if I reach out to founders, at least now I have like 24,000 followers. So it makes me have like a step up to people responding. Like if I only had 5 followers, people are like, oh, this person's fake. They're not real. And it just has like that one step up where if I reach out to founders, there's just that bigger of a chance of them actually answering me.

Mm-hmm. That's so funny. I feel like, have there been any cases where you've been really like surprised or have met someone in person that's recognized you?

I have actually, and it's more obviously at the NFT crypto events or like I've been around LA a little bit, but mostly when I first started out and was just starting to get following, it was at the crypto events. I was with my friends who are not in Web3 crypto at all. And they still would be like, oh, you're Trading Female. Or they were like, oh, you're Crypto Venetian 101. And I was like, okay, this is a little awkward. What about yourself? I mean, you have a following too.

Yeah, I think— well, I think my favorite ones, I write a lot about how to get into angel investing or leading syndicates or raising a fund. So I think some of my favorite encounters, like there's one where a woman came up to me at the All-In Summit And was like, hey, I read your article on how to angel invest and I made my first angel investment and I started listening to All In and like, that's why I'm at this summit and it's so cool to meet you. And it was so funny cuz we were literally like standing in the bathroom, like washing our hands.

Oh, that's amazing.

Yeah, it was so sweet. So I, I find that, and then I had like a reverse opportunity like that. There's this writer, Tim Urban, who writes the blog Wait But Why, which I adore. And he was at the All-In Summit and he wrote this really great piece called The Tail End, and it had a big impact in my life. And I saw him at the All-In Summit and I got to have like a similar moment with him where I was like, hey, like, I love this piece and you have no context for who I am, but it had like a massive impact in my trajectory. So I think that creating content, especially written content that's educational, has had a massive impact in my life. And those stories are always so heartwarming. So I always really like those. I'm sure that you've had similar experiences since you focus a lot heavily on educational content as well, right?

Oh, 100%. I think when you meet those people, you realize like what an impact they had and it feels surreal. Like you go outside and you're like, wait, you're actually a real person, but you impacted me so much. And so yeah, it's an amazing feeling though.

Yeah. Like you're not just a profile picture on Twitter, you're a real person. It's pretty crazy.

And now it makes it so much easier with kind of virt— being able to meet people virtually. Like I've reached out to some of my favorite people and they've agreed to meet with me.

Yeah.

So that's just been pretty cool.

And okay, so you talked about how you've traveled from these different cities. You lived in New York, you went to Australia without a plan, which is awesome. And then you moved to LA. I'm curious, how do you go about Exploring or getting your bearings in a new city when you are either traveling or living there? I would love to hear more about your process for that.

Yeah, so I actually only moved to Australia with my best friend, and when I moved to LA, I really didn't know anybody, like new friends of friends, but nobody. And I'd say like, especially for girls, cuz it's really a platform that only girls are on. I actually use Bumble with friends. Oh, and it sounds weird and it sounds crazy, but like so many people do it abroad. So I did it in Australia. I met some of my closest friends through it. And it's like, you know what, you're in a new place. Like, it's really a way to meet people. And I would recommend it to anybody, either if they wanna expand their network of friends and people, or if they just wanna try something new. So that's what I did. I also tried to just create a network around like-minded people. So I looked up Web3 crypto events in LA.

Yeah.

And I was able to really build this network. of individuals pretty quickly. I think at first it was hard for me to find the events. Like I was going to random events, talking to people, then slowly you build this network. And now I feel like there's an event every night in LA that I could potentially go to that's really revolved around interests that I have. So it took a little bit. And then the last thing, I love working out. And so I do tennis lessons weekly with some friends that just helps kind of meet and just get out of the normal, oh, let's grab dinner and a drink, but actually doing stuff together.

I love that. I love a good Tennis. Oh yeah, next time I come into LA, we'll have to get a tennis game in. I love, I love tennis.

Oh, 100%. Now I'm trying to get into pickleball.

Ooh, why pickleball?

It's actually the top growing sport in the US, but I'm not the biggest runner, so it's actually like a lot better and just quick. And yeah, I'm obsessed. You have to play.

Wait, so did you like find it? And why do you know that it's the top growing sport in the US?

Oh my God, there are like These courts in LA and people go like every morning, every night, and it's specifically blocked off. There's like 100 people there just playing pickleball.

Whoa.

There's also Pickleball Dow, but my parents have a place in Florida and their community has a pickleball court. So that's where I learned. And it seems like a really like grandma, grandpa sport. And now you're gonna be seeing it all around now that I said it.

I love that. I feel like it's not just a grandma and grandpa sport, it's just a sport that they picked up when they were younger that they genuinely enjoyed. And then it kind of Kipta generation. But now that I feel like the coastal grandma or grand millennial theme is popping up, I feel like a lot more people are picking up like tennis and quilting and golf and, you know, just—

And pickleball.

Yeah. And pickleball. That's so fun. So I'm, I'm curious, like when, what led to you diving into the world of Web3 specifically?

Yeah. So I first got my NFT out in LA. It's something called Bright Moments.

Mm-hmm.

And you would go in, you'd mint an NFT IRL, you pay for gas, and then you get this NFT. And my friend worked for the gallery, so he recommended I went. And I remember I spent $40 on gas and I'm like, why did I just spend $40 to get this stupid picture? Like, I really don't care. So I got that in June of last year. And then in August, my boyfriend kept telling me like, go on Twitter, it's so important. Like it's all investing, crypto finance. And so finally I looked at my NFT and it has like a white dress on, it has tie-dye hair, and I'm like, you know what? And it has rollerblades on.

Yeah.

And I have rollerblades too. I'm not a good rollerblader though, but I'm like, you know what? It kind of looks like me, like white dress, rollerblades. I'm gonna become the first IRL NFT. So I started on Twitter. I said I was the first in real life NFT. I posted pictures of my NFT and that just helped me get a following. So then I started having the conversations of being like, okay, what actually is the blockchain? Why do we care about the blockchain? I was already investing in crypto, but I don't think I fully understood the value behind digital ownership, behind the communities, behind the NFTs. And so I think I spent every single waking minute In the crypto space, NFT, Twitter Spaces. And then I went to NFT New York City when I met Drew, and I came back and that Monday I was doing tech sales still, and I had Twitter Spaces. I was working East Coast hours, so it was 2:00 PM Pacific, which is 5:00 PM East Coast. And after, my manager messaged me being like, that was completely unacceptable. And I was like, okay, but that's 5:00 PM my hours. Like, I'm hit my quota, everything's fine. And At that point, like my parents were already like, Alana, you're obsessed with crypto, NFTs, you're obsessed with investing. You need to take a chance on yourself. And so I ended up talking to Drew and started really spending all my free time sourcing deals. So eventually when he was looking for somebody, he brought me on.

Whoa, that's awesome. Okay, so I feel like when you're in crypto, I feel like your badge of honor is The losses that you sustained and like continued with crypto. So I'd love to hear about what one of your, like, either your first or your like biggest like crypto loss was. I've had some good ones.

So I don't know if you've heard of the Odd1sOut or Onis. People say them a different way.

No, no, no.

But they're basically this NFT where if you look, they're from like the side view. So they're the first like NFTs that are face to side. Mm-hmm. They were getting so much hype and at the time they were at 3.5 Ethereum, which Ethereum was at like $4,000.

Like 12 grand.

Uh, yes, 12 grand. And of course I go to my boyfriend and I'm like, hey, we should split this. Like, this is gonna be the next big thing.

We should get it.

He's like, Alana, do you even know what you're doing? I'm like, yeah, yeah, we'll be fine. Let's split it. Until he sends me it, we buy it. I don't even wanna look at what it's at right now. Like it's Probably at like point two, like on a good day. It was at one each for a while, but like regardless, it wasn't just my money. Like I was telling my boyfriend, like this is great. I know what I'm doing. So that one wasn't one of my proudest moments. If you look at the chart, it's at really the tip, and I lost his. I still need to like came back. Like at this point, I've gotten my Ethereum stack up where I'm like, all right, it's a tax. Give them a little.

It's a tax.

Oh, 100%. Except you have to sell it and I haven't sold it yet. I'm like, why am I holding this? The other one was El Cabones. If you, you probably haven't heard of that one because it was like, I think I learned very quickly that FOMO is real in this space and I should not be acting on the FOMO, like trying to do a quick win like a lot of people do. So bought that one at like 0.8, went to like Basically zero. It's in my hidden folder because I'm just— I can't even look at it in my wallet anymore. But I would tell anybody— oh, I'm like, I can't look at this, this is awful. But I tell anybody, like, if I stopped there, I wouldn't be where I am today. I was saying, really easy at one point.

You can't— I just, like, I don't think you can be in this industry for a while and, like, not sustain a pretty massive hit. But I, I think, like, It's similar in venture too, where your, a lot of your outcomes can be pretty binary. It either goes way up or it doesn't go anywhere. And it's just kind of like what you're used to when you're building a portfolio. So I'm sure you were investing in like a bunch of NFTs and some of them did really well, some of 'em didn't. But I always like to hear about the, I think you get the losses first a lot of times.

Oh, I don't think people, I think I've tweeted that, like, I don't think people Talk about their losses enough.

No, never. Because I, I have friends that have lost like, like millions in like liquid, especially, oh, like the OHM and Beans. That was like interesting.

Anyways, I've definitely had other ones too, like not including the Bitcoin that I have a cost basis of $55,000. Like that's down so much. Like there's so many in my list.

Yeah.

But at the end of the day, it's like my wins have outrun my losses.

Mm-hmm.

Which is, I feel like all I could ask for in this space. Mm-hmm.

Absolutely. So I'm curious on the, on the fundraising side, from a founder perspective, what are 3 common mistakes you see founders making and what are some of the tips you have to avoid them?

Yeah, I'd say one is cold outreach.

Mm-hmm.

Like you could really look on any VCs on LinkedIn, look at mutual connections and ask somebody to make the introduction. Yeah. And that That one step and that tailored approach goes such a long way. Like, I'm so tapped into the venture space. I think you are too. If founders take that extra step to try to get an introduction, like, I'll take the meeting and you never know what could happen. But if they're not even, if I'm just getting a cold message similar to everybody else, like, I probably 99.9% of the time I won't answer because I do feel like there's so many ways to get in touch with me and do a tailored approach where I would just Like, tell people, like, try to be more tailored, try to find a person who can make a connection because there's so many ways to do that.

Yeah.

So that's the first thing I see with fundraising. Some I feel like are fundraising too early, like they haven't even made an MVP yet. They really just have spent all this time on a deck and then they're gonna spend 6 months trying to raise a round of funding. Like, if they spent that time actually trying to build something, I think they'd be so much more likely to close a round than if they just go, Here's a deck straight to fundraising. Here's an idea, but I put in none of my time and I want your money. And we see that sometimes. And then the last thing is finding a product market fit. I think a lot of times in this space, people are just throwing out ideas and hoping that one sticks with some VCs where it's like, really test out your product, see if there's a product market fit, and then go from there.

What are some of the current trends that you're excited about in the venture ecosystem?

We look a lot at play-to-earn.

Mm-hmm.

I think there will be so many bad play-to-earns coming out in the next 12 to 18 months, but I also feel like after that there's gonna be a lot that succeed. I think STEPN was a good idea, but maybe if Nike, who just acquired obviously RTFKT, like came out with a STEPN where you're actually walking and then could use those tokens to buy shoes, that would create utility behind the token.

Mm-hmm.

So I'm trying to find play-to-earn games that really excite me. And then also we've been looking Looking a lot at just the infrastructure behind Web3.

Yeah.

So DAOs, different tokens, different DeFi protocols. So we're generalists in terms of what we look at, but that's where I've kind of been focusing a lot of my time.

I like the theme that you mentioned, having the utility behind the token. When I was having conversations with a couple of my friends who are focused around the celebrity-founded space specifically, a lot of them have mentioned, actually, I think it was Nik Sharma who I had on the podcast. A couple weeks ago, but he was like, if there's not a reason for the brand to exist in the context of that celebrity, it won't succeed. And I feel like it's similar if there's a token without utility, it's really challenging to have like a successful launch. I'm curious for your thoughts on that, if there's like differences in that.

No, I completely agree with that. I think right now it's hard because you have this token, everybody has it. It's usually a saturated market. It's inflationary, not deflationary, and then you can't utilize it in the real world. And so at least we're seeing Ape Token and Gucci just do a collab where now you could use your Ape Token for something and actually spend it in real life. And in order for this to succeed with the tokens, we're actually gonna have to see that more and more, or else most of these tokens will just go to zero. Yeah. Because there's no way for it to burn. There's no way to actually utilize the tokens.

That makes sense. And, and thinking about the broader venture ecosystem, who inspires you both as an investor Yeah, I mean, I'm first gonna say Drew Austin.

I know that that sounds cheesy, but he is probably one of the smartest people I know, and I think he's just helped me so much grow in VC as an investor, find different companies, and really hear his thoughts in the space. I think he's so tapped into it. So that's probably been my biggest one. And then also as an investor, my boyfriend is a VC. He's actually the one who started HyperGwap with Gali. Oh, that's so cool. They both started this fund, and I think they've just allowed me to, in the beginning, really understand venture and then really dive into the space. So both those are pretty cheesy, but I'd say those are 2 who obviously have had the biggest impact on me.

No, that's awesome. And then going back to some of my fun questions that I have on deck, uh, I would love for you to talk about what your favorite concert has been, if you have a top one.

Ooh, I love festivals, but I'd say I've been to Vegas a lot recently, so I'm more into like the DJs. So I'd probably say I love Kygo and Zedd.

Love Kygo.

Are like my 2 favorite concerts that I've been to.

I think Zedd. I think Kygo's playing at the, the Under 30 conference this year, if I'm not mistaken. But I feel like no trip to Vegas is complete without Diplo.

Oh, love that. I agree with that too.

That's awesome. What festivals do you Or yeah, what festival have you really enjoyed going to?

I went to Ultra Japan with my best friend. We kind of traveled to Japan and that one was definitely a highlight.

Dang. Did you plan like your Japan trip, like around Ultra Japan specifically? Were you like, let's just send it?

No, I think we were deciding to go to Japan and then we saw that and I think maybe we extended it a day or two, but we were like, yeah, we're for sure going.

That's super cool. Dang.

Yeah.

I've always wanted, I feel like I wanna go to Burning Man. Yeah, I know all the posts are. This week. Well, this, this podcast will come out later, but all the posts you've done this week looks insane. Yeah. It was funny, like I sent out one of our investor updates and I was getting back some like out-of-office responses. I'm like, mm-hmm.

Oh, you have a good setup, investors. Yeah, yeah, yeah.

They're awesome. Okay. And then my last question would be, if you had to pick, what color would you classify this season of your life as and why?

Honestly, life's been pretty good. Like this past year I've done, from this time last year, this year I've gotten a following on Twitter. I've been able to jump into VC. I love my job. Like I think it's the most exciting job out there. So I'd probably say yellow, like things have just been so great. I'll do between yellow and green. Like it's been go, go, go nonstop, but it's also been like absolutely amazing. So those are 2 colors I'm going to select.

I love that. Well, Alana, thank you so much for joining us today on Seed to Harvest. If you would like To connect with Lana, please visit her Twitter @TradingFemale, and I'll leave that in the show notes. But thank you so much for coming on.

Thanks so much for having me, Paige.

Thanks so much for tuning in today to Seed to Harvest. If you enjoyed this episode, be sure to subscribe wherever your favorite podcast listening platform is. I'll be releasing new episodes weekly, and if you have any questions or comments, feel free to let me know. That's Paige Finn. Paige and then Finn with 3 N's. Thanks and see you again next week.