Impressionism Capital Founding Partner Sydney Thomas on Fund Construction | Seed To Harvest Ep46

Welcome back to Seed to Harvest, everyone, a podcast with founders, creators, and investors about their stories, frameworks, and tactics. Today I'm joined by Sydney Paige Thomas, founding partner of Impressionism Capital. She invests in early-stage startups, specifically focusing on investing in real people. We'll get more into that in this episode. Since becoming the first hire of Precursor VC, we did an episode with Charles a while back, which is on our YouTube, over 6 years ago. She's built a community of over 400 co-investors along with intuitive systems that scale small to mid-sized teams. She's a proud Beyoncé stan and dedicated writer, and she writes about her experience building her first fund on her blog. Okay, so we were chatting before the show. Something's in the water this year. Big reset energy. What's on your in-out list for 2023?

Yes. So in is abundance. just claiming all the abundance.

Wow.

I'm really, really excited for the big things that we're planning at Impressionism Capital, but also just for life in general. And out then, I think, is just holding on to things that don't serve me anymore. I think that last year also was a big year of change for me, and I think that I'm just really excited to have the Like just freedom, like, I guess, like bandwidth, space to not be like clinging to things that don't serve me. The big one is this house. I'm actually, and we were chatting about that.

Wow.

I'm actually going to San Diego, my hometown, which is also where Paige is from. Yay. I'm so really excited to just like not be so obsessed with keeping things the way they were just for, just because they were the way they were.

I love that word abundance. What is one thing about you that you don't get to share as often, but you wish other people knew?

Ooh. So I have had 5 career changes. It's, it's been a lot. And so I think like going from the, when I was in the public sector on the government side to then the nonprofit side, to then the startup world, to then the VC world. Has been such a life of learning. And so just really grateful for all of the switches because I think they turned me into who I am today. And a big part of managing the switches was actually being able to have a certain amount of capacity for uncertainty.

Mm-hmm.

And so also really grateful for all of that navigation of those uncertain waters because I think that is how I was able to build the courage to, to I love that.

I was reading through, I don't remember if it was your Twitter or your blog, and you had a really great book list somewhere. And I feel like you're, I'm getting the sense that you're a big reader. So I'd love to hear if there's any like books that have helped you through periods of change that you'd recommend for other people. 'Cause I feel like this is a big year of change.

That's a big year. Hmm. Oh, that's such a good question. I mean, there's so many, there's so many good books. Like it's actually impossible to like have an actual list. But I'd say that one of the people that I really loved reading about, it's called Looking for Lorraine. It's about Lorraine Hansberry, who is the writer behind A Raisin in the Sun, which is an amazing play. And the cool thing that I have a lot of— that I get a lot out of from reading books like that or biographies like that is you're reminded about like how hard it was for anyone to do anything really interesting. but also like how amazing these people are who existed. And so you almost feel like you're in their presence when you're reading these books. And so I'd say for anyone who's going through change, reading a book about someone else who went through significant change, I think can give you a lot of solace.

I love that. And also on the media track, I noticed your playlist linked on Twitter. So if you could choose one Beyoncé song to be your anthem in this season of your life, what would it be?

Oh my God, I have so many. It's so hard. And they're like all—

I was like, I have just hard questions before I start talking about Venture.

Seriously, this is the toughest one. Oh my gosh, Cozy. Probably Cozy from Renaissance, where she talks about how cozy she is in her skin and how comfortable she is with who she is. And I just think it's a beautiful anthem that's reflective of how I feel. Like we're here.

We're cozy. I love that. I always think of like ASAP Yams when I think about like cozy.

That's so real.

Yeah. Okay. So to talk more about venture, you recently made the decision to start building your own firm. I'm curious, at what moment did you realize, or let me, let me ask you this. What were, what were the hours and days like after you made the decision to go your own?

path?

What, how did that feel like? What kind of emotional journey were you going on and kind of what were your like key decision factors in starting your own thing?

I was in my head a lot. And so I think a lot of the hours, I don't even know if I can recount what one hour felt like versus the other. It just felt like this whole glob of time, like time did not exist. I was just constantly thinking about like, okay. Playing all of the potential iterations of what I wanted to do in my head out. So it was a lot of this, like, time with myself. Unclear how long I spent.

Unclear. Just floating in the Matrix.

Literally, that's how it felt. You're just like, wow, wait, what day is it? Oh, it's Wednesday. Oh, I haven't actually taken out the trash. Oh. Crap. I love that.

Well, fast forward, now you've had the opportunity to build your team at Impressionism Capital. How did you think about building your team? And for other emerging managers or perhaps founders that are out there, what are kind of like the frameworks that you went through in deciding to bring folks onto your team?

I tried to, um, put together some sort of templative, like expected agreement in my head before. And I just don't— I never got to a place where I was comfortable with what that template was. I remember actually I was like, I had it in my Asana tasks, like, must write out the expectations of a venture partner. Never existed. I never— that does not exist in anything that I own right now. And it was largely because I actually wanted people and partners who actually, like, could see my blind spots and fill them. And so that was actually a huge thing that both Shruti and Jen bring to the table that I'm so excited about. Shruti's background in COO, like, ninja world is just ridiculously phenomenal. She knows how to read legalese. She knows how to manage a 100-plus person company. She just knows a lot of things and a lot of things that I don't know. And so when we were jamming about impressionism, she was coming up with all these questions like, well, have you thought about this? What do you think about this? And I was just like, oh my gosh, one, this is so fun. Like, I love jamming with her. We've known each other for 5 years. And so we had been jamming on something in some way, shape, or form for the last 5 years. Actually, the first project that we did together was this group that we called Full-Timers Living. Yeah.

Wait, what is that? I wanna hear more about that.

So we created this little group and it was 4 friends of mine where we were going to buy houses together and rent them out and then live in Paris together.

Wait, that's so fun. Did it happen?

It's so fun. It didn't happen. We all realized we were too broke to do this.

Wait, that's a, that's an awesome goal. Do you think you guys are gonna jam on that in the future? Is that something that's in the cards?

100%.

I love that.

100%. It's, we're at full-time Paris living phase 2.

So very excited. Phase 2.

I love that.

Um, so going back to your previous experience at Precursor, I think one thing that's really interesting about Precursor, and in my conversation with Charles Hudson, who's the founding part, he talked a lot about how there wasn't really nomenclature or an established definition for pre-seed when you all started raising for Precursor Fund 1. So can you share a bit how the pre-seed ecosystem has evolved? And Precursor obviously is definitely at the forefront of the narrative as you talk about pre-seed as, as an institutional practice. So I would love to hear like how the ecosystem has evolved from your perspective.

Yeah, it's such a great question. I mean, back in those days it was Precursor, A4, Pear, YC, 500.

I think that was it. That was it. And like some angels, lots of angels.

And some angels. And so fast forward to now, there's hundreds of pre-seed, seed funds. And I think that what I'm really excited about is how all of those different funds that enable a whole different community of founders to exist and to build and to create. really interesting worlds that didn't get to exist when there's just, you know, a few people who make that kind of decision.

Was that the ecosystem that you described at the beginning? Was that like 2015, 2016?

Yeah, yeah, I joined venture in 2016.

So it's still pretty recent that there's been like such a massive shift in the pre-seed ecosystem, which I think is like interesting when you think about it in like the broader scope of people are like, oh, pre-seed capital is like going X amount of ways when it didn't really like exist until 6 years ago.

So real. So real. So much changes in such a short amount of time, which is something that I like to anchor on. I think when folks can get disillusioned or just sad, it's like that reminder of like, well, also though, look how much the world changed in 6 years.

Yeah. How did you, I guess like going back to your time there, you spent 6 years working with Charles. What were some of your biggest learnings and how did they shape your investing practice as it stands today?

Mm-hmm. I would say a big one is founders. We work for founders. I think that Charles really demonstrates that ethos, and that's something I learned from him, and it's something I take into my work today. And that I just came to this call from hopping off another call with a founder, and she was just like, thank you so much for taking the call, because it was a last-minute, you know, schedule thing. And I was like, that's my job. Like, this isn't— there's no need to thank me. That's literally my job. And I think that sometimes when you don't have that type of ethos in the firm, or that's not the same kind of like ethos that you're brought up with, with another firm, it's not as common to just expect that high bar for yourself.

Mm-hmm.

And so that's a big one that I took away. And so really grateful to have learned under him. And to be doing that with my founders.

And to go like a bit into the nitty-gritty, how did working at Precursor affect like how you think about fund construction now?

Mm-hmm. So I am so grateful I got to see so many different founders come through and learn from them while I was at Precursor. And I also realized that I think there's a way to do pre-seed investing by investing in fewer companies and do it, have a long-term view around investing in those fewer companies in a way that you can double down and support them, not just from pre-seed, but on and on and on. And so the fund construction of Impressionism Capital is that we have a small enough pre-seed portfolio that we have enough reserves capital to double down and lead those next rounds that they're raising. And that's because that's the type of relationship that I want with the founder. I want to work with them for 10-some-odd years. I think that when I invest in them at their pre-seed, I see it. I see the lights shining, you know, on the New York Stock Exchange and like in the bright lights. And so really excited to build a fund that's able to support those founders through that.

I love that. To take things to a little bit of a different subject, like earlier on in your career, one of my favorite writers, Ocean Vuong, who wrote On Earth We're Briefly Gorgeous.

Beautiful.

Yeah, that book, incredible. But he really sadly had one of his main mentors pass away, and I love the way that he described him as a patch of grass. Like, it can be really challenging if you're working in an industry where you like hear a no a lot, especially doing your own thing. And I love that he described his mentor as a patch of grass. So I'd love to hear like, who was that like patch of grass for you where you just felt like seen and accepted? And this can be like earlier on in your career, whether that was in politics or nonprofits. But yeah, who, who are those folks for you?

That's beautiful. So when I first started in venture, I started this group called Women of Color in VC. And so it was a community of us that would order in pizza and hang out at a coworking space at night and just talk. And a few of the women in it were Maria, who's now at Hulu Ventures, and Jamyra, who is now at Reach. And we— one of our first events was actually with Miriam Rivera. And we asked her— I sent her a note saying like, hey, I have this group of women, would love to, you know, organize like a coffee chat or one of a pick your brain opportunity. She invited us to her house. where she cooked us dinner herself and spent hours with us talking about her experience in venture, her growth, her learning.

Wait, yeah, for folks that might not be as familiar with who she is, can you explain a bit of her background? Yes.

So Miriam is— was one of the first lawyers at Google. And so that's where she got her start. Like, she's OG, OG Silicon Valley. And so it was amazing to have those stories from her time there. And after she left Google, then she started her own startup. And then after she started her own startup, then she started her own fund. I mean, she's just amazing. There's nothing she couldn't do. And to be invited in the presence of someone like that and for them to be that warm and to be that vulnerable with us and to be that kind was just a reminder that Oh, okay. I'll be okay. And I think like that exactly to your point of that patch of grass, it felt very much like, you know, okay, this is like a little nap. Can take a little nap on this little patch of grass and then get up and hustle tomorrow. Yeah.

Yeah. I love that. Oh, what a special time that must have been. I feel like it, those are like the moments where you like, I think especially like looking forward and like playing out your career and having like that abundance mindset of like, oh, there are people that are deeper into this career that have just like great intentions and are so warm and like, that's where I I really want to be in like 20, 40 years. You know, it's like cooking folks that are relatively newer to the industry dinner and telling them about the fun stories that you've shared with like folks. Like, I love that. So I would love to go back to— you have a deep history in legislation, which I think is unique in venture. So you served on the Bloomberg administration, various committees in Oakland. Can you share more about that experience and perhaps how it contributed to your multifaceted in this adventure.

Yeah, thank you. So I was— I first joined the Bloomberg administration in like 2010. And so this was right after, you know, Obama had got elected and the House was like super, super, super red because the ACA had just gotten passed. And so then, you know, all the Democrats got voted out after the ACA and it was just dramatic. And so I— it was very dramatic. And I really enjoyed the work of like drafting legislation and also trying to figure out a common ground between very different stakeholders. And I'm using so many of those tools now. It's how am I actually building relationships with different stakeholders who have different incentives and different interests and understanding what they're excited about and then telling them that story that also is aligned with what I'm excited about. So I think that politics is just an amazing training ground for any industry and really excited that I had that experience to prepare me for—

Yeah, I feel like you had some pretty incredible awards that I feel like you didn't talk about.

I didn't. It's been so many. And it's been— I think the cool thing is that like every year, because of all these different career changes, I feel like I'm also completely different.

Yeah.

And so that's also been really fun. So a lot of them I don't remember either. Yeah. Because I'm, I'm not there anymore. I'm someone— I'm different.

No, this was like— this is more recent. So in 2020, you received the Champion of Justice Award from Esquire Apprentice, which is an Oakland-based nonprofit that creates alternative pathways to legal careers. And then you're also appointed by the mayor to serve as a commissioner for the City of Oakland's Public Safety and Services Commission. So she's involved. Just want to brag on Sydney for a bit.

And you know who taught me this is my mom.

Really?

From— and so in San Diego, she has— she won the Lemon of Distinction Award this past year. And so came last year around April, the whole family came to San Diego to celebrate her. We were downtown in like Seaport Village, and it was really special. And they were just listing out all of her accomplishments. And it— I think she probably felt the same way that I'm feeling now. It's just like, Okay guys, like, please stop, please stop, please stop.

I was like, I just shared like a small sampling of the ones that I found. That's awesome. What, what else have you learned from your mom that you feel has like really impacted you as a person?

Hmm. Oh man. I mean, my mom is the, she is the hustler. Like, I'm all of the things that the schools I got into when I, especially in high school. and middle school, they were all because of these, like, strategies, strategizing, forward-thinking, hustling tendencies that my mom has.

Yeah.

She grew up on a farm in West Virginia and then figured out how to live a completely different life in San Diego. And she's just amazing. I mean, like, it's— I think so much of also my leadership style comes from her. She's extremely collaborative, wants to get the feedback from all the people and then makes the hard decisions. And so I learn a lot from her all the time. Still learning, thank goodness. Very grateful to be continuing to still have her in my life. And still—

I love that. I, my mom and I are really— I actually like just came from breakfast with her this morning and I feel like, oh yeah, yeah, she's awesome. She's an artist, so I feel like she's taught me a lot about like embracing my creative side and Yeah, I love that we have a close relationship as well.

Beautiful. And where's your mom from? Where are you from?

I'm from San Diego. Yeah. So both my parents are in San Diego. I was born in New Hampshire, and then I have 2 younger brothers, both of whom go to SDSU. And I also went there, as my mom likes to remind me, several years ago. I was like, whoa, it was 2020. Don't go using several of me. But I don't know. That's not how it works.

She's just reminding you. She's like, you know what? You can pay for breakfast now.

Yeah, yeah, exactly. But, but yeah, so on, I wanna go back to one of your quotes. So you said, in order to be an effective pre-seed fund, you must put your firm in a position to see 1,000+ companies a year. So how do you think about building systems that scale when you think about being like a solo GP with venture partners? How do you think about like scaling your sourcing? organization? I'm assuming very community-based, so I feel like we have a lot of similarities there, but let's hear more.

Very community-based. Also really love software. I think that software as a tool for your fund is just so valuable.

Wait, I want to hear the tech stack. We can't just be saying software.

Oh gosh, I know, right? Especially this day and age. I feel like there's so many new amazing software systems too that I'm constantly learning about, but I am an Airtable And so we'll build actually an open-sourced Airtable that shared how I built out a lot of the OS for Precursor. It's been downloaded almost 2,000 times, which is crazy.

I have— I am one of those 2,000. I have downloaded it. Nice!

Yay! So that was V1. Learned a lot through that and actually have 2 folks on the team who are amazing and engineers who are taking us to a really interesting place around how are we both integrating some of the screening tools that we're using into Airtable, into Airtable, and also the continued support of the founders into Airtable too. And so like this really following the founders and companies all the way from that initial meeting to investment, post-investment, all of those things.

I love that. What other, what others are like, all right, you have like $300 of software budget left. What's like non-negotiable?

Oh my God, what's left? I mean, I'm fundraising, so DocSend. I'm pay— I'm just like, I have to use DocSend. It's the best. And then for internal collaboration, we're heavy Slack users, unfortunately. I think that like Slack is—

I love that, unfortunately. Sorry everyone.

So fast and you can do so many things in there. It's just like, so I love the voice note functionality. I love everything. And so really fun and useful to use Slack, especially a remote team. Yeah. Because I'm here, Shruti's in North Carolina, Maria and Dustin are in Indiana. Jen's here too in Oakland. But you know, we're pretty spread out. And so it's really helpful to have that.

All right. As we wrap up, what Would you say is your blueprint for success as you continue to build your firm? What I actually— what's like the one metric of success you think about the most that'll carry you forward?

Interesting. I mean, the thing that I think a lot about is refinement and resilience. And so as you take in feedback, How are you refining your strategy, your story, your thesis based off of that feedback? And how are you also staying resilient enough so you know, like, when actually the refinement is necessary and when it's not, and when you just keep going with what you say or what you think is the best?

Well, thank you so much for joining me today, Sydney. I had a blast. I'm excited for people to listen to this. If they want to hear more from you, what's your blog address on the internet? I'll link it in the show notes as well. Don't worry, everyone. You don't have to remember this, but are you most active on LinkedIn, Twitter? What's your vibe?

I'm much more active on LinkedIn these days. I think it's been because I'm doing more long form. I also post a lot of the long form to LinkedIn. I saw the heavy sigh.

What are your thoughts? No, it's been interesting. I don't know. Twitter's been my home. Like I've like, you know, built up like 32,000. Folks and like used to be like million monthly impressions, but I've just I feel like I kind of got myself into like a professional, super professional educational resources only, and I kind of missed being like myself. Like I'm a 24-year-old fund manager. I live in San Diego. I like to surf. I like to be silly. So I've honestly been liking TikTok and like making funny videos. You know, I feel like imperfect content is in. I think I might. Yes, I might do some more on LinkedIn, but I feel like I love that. I love a podcast. Just like more nuanced content, and like that allows me to be silly and myself.

I love nuance. I support that 100%. I'm excited. I'm gonna have to look you up on TikTok. I don't have TikTok, but I do.

Okay, perfect. Writing it down in the task list. No, I love it. Okay, Sydney, thank you so much for spending time with us. I wish you all the success. And yeah, I'll link her LinkedIn and Twitter in the show notes for you all to follow her. Thanks so much for your time.

Of course.

Special thank you to producer Riley Jennings and podcast editor Tate Doherty for your help on this episode. If you're listening and you'd like to connect with me, follow me on Twitter or LinkedIn, Paige Finn with 3 N's. Thanks again for listening. I really appreciate it. You can look out for new episodes every Monday at 5 PM. PST, and if you'd like to learn more about the strategies and tactics of seasoned institutional investors and rising venture stars, check out our YouTube channel at Seed to Harvest. Also, my TikTok channel is Seed to Harvest, where I post a lot of behind the scenes. And if you like this episode, please rate and review this podcast wherever you get your podcasts. That's on Apple or Spotify. Anyways, thank you so much for listening. I hope you have awesome rest of your day.