Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.
Discussed: Meeting Yancey, Setting Kickstarter’s Tone Through Community Management, Choosing Projects to Feature, Learning How To Manage Up, Moving On, Book Recommendations.
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Craig: So how about we start with you talking about your background before Kickstarter.
Cassie: Yeah. There isn’t much of one to be honest. [Laughter]. I went to school in California at UC Santa Cruz. I worked at a radio station and studied literature. Then I pretty much threw a dart at a dartboard to decide where I was going to go after college and ended up in New York.
I started working for this music company managing a thing called White Label for them and selling records. And I worked for a concert company called Bowery Presents at night. So I’d go from daytime office to night time working the door at shows all over the city. It was really fun.
In my first month in New York in 2008 I was at a No Age and Health show at Market Hotel. I was with a guy I had worked with who quit and had gone to work at Emusic. Also at the show was his new boss, Yancey [Strickler]. Me and Yancey really got along. We stood in the back of the show and just talked the whole time. Then, two years later, Yancey wrote me an email and was like, “I’m starting this company. Let’s get meet up.” I was like a baby still. I had only worked at this music company and knew nothing about startups or tech… I had no developed sense of anything.
Craig: Had you guys stayed in touch at all?
Cassie: Not really.
Craig: So he emails you and you’re like, “Alright, let’s meet up.” And what’s that conversation?
Cassie: We got dinner at Sweetwater. I had no idea what I was looking for in my next job or what to expect from the conversation. He was laying out behind what they were trying to do, and it was clear that him and Perry[Chen], who I hadn’t yet met, believed really purely in the why of the idea behind Kickstarter. They cared deeply about enabling all types of people to make creative things and put them in the world. I remember being really moved by his sincerity. And I was like, no matter where this thing goes it’s important to me to be around this kind of energy.
Yancey believed in what they wanted to do so purely. A matter of days later I put in my two weeks at my job and started working for Kickstarter. They didn’t have funding yet, I don’t think.
Craig: Was the product the same thing in the beginning?
Cassie: I mean, the fundamentals were all there. You know, you set a goal and a timeframe. And it’s all or nothing. But there weren’t complex creator goals and engagement tools and resources in the beginning. We didn’t yet know what was going to happen or what was going to be needed.
Craig: So what was your function?
Cassie: I was hired as a customer service person, technically. When Kickstarter first launched, there was no clear indication of how you launched a project. You had to be smart enough or curious enough or ambitious enough to write into customer service and be like, “Hey, I want to get my idea up here. How do I do it?.” So I would field all those requests. Some projects we accepted, but some we didn’t.
Craig: Wild. What were the criteria in the beginning?
Cassie: I mean, I’m not gonna say that we had well-formulated criteria. It was intuitive and I want to say “warm,” because that’s the only word I can think of. There was a really supportive enthusiasm coming from us, we were just so into the things that people wanted to try and do. Personally, I really like people and I like interacting with them. So I loved having a job where the bulk of what I had to do was talk to people and help them coax their creative visions into life.
I think part of the early days was figuring out what we meant when we said Kickstarter was for “creative projects.” And, in the beginning, it was certainly easier to take certain kinds of risks. For example, we accepted this woman, Emily Richmond, who wanted to sail around the world. She promised to send backers photos from her journey and we were so into that. It was her creative pursuit.
Later on things evolved and we had to be a little bit more specific in our parameters to accommodate the influx of attention. With projects like that it became a challenge to figure out where they belonged on the spectrum of creative work.
Craig: And so how many projects were coming through a month?
Cassie: The product evolved and the process for applying for projects evolved as the influx got greater. It’s been such a long time it’s really hard to say, but I just remember that when it hit…it hit hard and there were not that many of us to deal with it all. Actually, my old coworker, Cindy Au, posted this old video of us way, way after hours in the Kickstarter office being so goofy and dancing to oldies in our chairs and rolling around the office. I know we were there because we were backed up approving projects and talking to project creators.
Craig: And so what was the point where it actually hit, where it started getting traction?
Cassie: I just remember a before and an after. I remember that Yancey and I did the Renegade Craft Fair, which is this really DIY Brooklyn event. We had a booth and Yancey was there and we were still so small I remember people being like, “What’s Kickstarter?” and I would take a deep breath and get ready to tell them all about it, and then suddenly at some point like a month later I just remember not having to ever explain to anyone what Kickstarter was ever again. I would be like, “I work for Kickstarter,” and they would already know about it.
Honestly, I think it was a combination of well-designed product and fortuitous timing. We were just coming out of a crazy financial crash, people were struggling to figure out how to make their art, and then Kickstarter came along and became a solution.
The traction kind of went project category by project category as these different communities picked up on and figured out how they could best put it to use.
Craig: Were you guys doing any marketing?
Cassie: Not really. We had a press guy who fielded requests, but he was part-time for a long time. Perry and Yancey played it pretty close to the vest. They were very deliberate about the interviews they did grant. They turned down a lot of stuff. I think that really helped contribute to the feeling that Kickstarter was a platform about its users. We did not feel like a “founder first” company.
Perry and Yancey weren’t running any circuits. They weren’t trying to show up at all the conferences. They weren’t trying to network, really. They were very deliberate about what opportunities for promotion they pursued.
Craig: When you met them did it strike you that this was going to work out? Or was it the idea that was just really compelling?
Cassie: You know, what’s embarrassing to admit is that I didn’t actually investigate the idea itself that much. People would tell me, “That’s so smart!” and “That’s so cool”, but it didn’t strike me as this genius thing. The idea itself was so secondary to the type of people I saw that I’d be working for. I was only like 23. I wasn’t looking for a big break. I was just looking for role models and mentorship and the thing that would help me get to the level where I could find “the thing” that I was supposed to be doing
Craig: And so at what point are you working there and you’re like, “Oh man, I work at a startup now?”
Cassie: I didn’t even know what a startup was when I started working there. I think probably when Fred [Benenson] started working there and we rented that loft on the Lower East Side and outfitted it with a whole kitchen and we would make handmade tortillas and stuff. That’s when, in retrospect, I “worked at a startup.”
Craig: And so how long was that before Fred joined?
Cassie: Not that long. Maybe a month or two. Fred didn’t start until we got an office. And I think it was a couple months until we got an office.
Craig: So they hired Fred to do what?
Cassie: I honestly don’t even remember. What I do remember is that Fred was a guy who knew cool people, was good at the internet, and it seemed like a good idea to have him around. That was my impression of his hire — I’m not even sure he got a specific job title right out the gate. I never really had a title in the entire time I worked there.
Craig: So without any title, how did your job shift along the way? Were you always that community person?
Cassie: The scope of the job changed a lot because I was also a good writer and I had good instincts for how communities online functioned, even though I didn’t know that was a thing at the time. I think the joy I took from interacting with people really helped that.
Initially, I was hired to do customer service, which meant accepting projects and doing basic troubleshooting. Then I started writing for our blog. Then the role of accepting projects and working with project creators became more formal. It quickly became a sprawling, unwieldy job that did not really have a title because it fell into so many different camps. Like most first employees at startups, I was just doing a little bit of everything.
Craig: What do you think it is about you that made you good at managing the community?
Cassie: I think I was good at listening to people. I think I genuinely cared about what people had to say, too, which makes people feel heard and — most importantly — it makes them feel understood. Even when you can’t tell somebody what they want to hear, if you make sure they feel understood, you can still make them feel happy and good.
If you give a community a tool to use, they will find their own ways and make their own rules with it. But I think there is always a line. I think rule one of community building is knowing how to respect a community’s right to invent itself, while still being able to quietly guide it from behind.
Craig: Yeah, I kind of wonder how much that role is about being a shepherd-type person. Did you ever have to say, “No, we’re not this or that.”
Cassie: Yeah. I would say a challenge with community — or really anything — is getting people to do something without making them feel like you’re telling them to do it. That’s the challenge I think all digital communities face – finding a way to set a precedent and make people feel empowered to make their own choices, while ensuring they’re making good choices, so everything doesn’t go haywire.
At Kickstarter we worked so closely with all the initial project creators and communicated with them so much and stayed so in touch with them, we had an initial batch of super high quality projects that really demonstrated the best use of the platform. Then the second generation creators coming in and used that initial community as a kind of guidebook and template for project building. And then, over time, the community began to internalize a set of rules and best practices.
The community became self-regulating very fast, but it was because we put that much effort into making sure that the initial projects were really good and really were the best possible use of the product, you know? It took the pressure off of us to tell every creator, “This is what you have to do and how you need to do it.” They were able to find their own way very easily.
Craig: It makes sense but how does it self-regulate when Kickstarter seems to mostly just be about viewing or posting a project?
Cassie: There’s a message box on every project. So you can always get in touch with creators, and what you get is a lot of second gen and third gen creators who are e-mailing people with successful projects and asking for tips. And then slowly creators saw that their experience was a valuable resource, so they started independently talking to people, writing blogs, posting how-to’s, running workshops, etc. The community started helping itself out, very fast.
And most creators have been backers at some point. And at this point, people are backing dozens and dozens of projects. Most people have a really strong sense for what feels good, as a backer, and they aren’t afraid to weigh in about it. Often, even in the early days, we would see project updates getting a lot of feedback from the backer community. And creators would be very responsive and receptive to that feedback. We’d see whole projects change course, you know?
Craig: Do you remember any instances where the community changed the course of the project?
Cassie: I remember there was a videogame where they were trying to make it and they blew through all their money in development and didn’t end up with a product they liked. They were like, “This is where we’re at. We are not happy with the product. We need to do this.” And people stepped out of the backer community and came on as developers and designers and gaming people, and they worked together to try to finish this game so there would be a final product.
A more common example is when somebody wants to self-publish a book and the project ends up being really successful. Then they end up with a book deal they weren’t expecting and all of a sudden the backer community is back-burnered while the author is like, “Now I have to release this book through this company first. They’re going to handle pre-sale and stuff like that.” And the backer community is like, “We should get first access because we supported you first. We are the reason you are so successful.” That can cause issues.
Craig: What did you as the voice of Kickstarter when someone got in too deep?
Cassie: Oh. Well, I think in the beginning the idea of a Kickstarter project exceeding its goal 10 times over and making a million bucks was like, “Ha! That will never happen.” But then once it did start to happen and once we saw the very real trouble that people would get into, that’s when we doubled down on creator resources. And that’s when things like reward caps began to appear in the product.
Craig: Gotcha. Let’s talk about the hardware product statement. Why did it happen?
Cassie: There were just a ton of product projects on the site all of a sudden and the site started getting a reputation in the press for being a place to launch a product, which was not our core mission at all. We were trying to figure out how to walk the line between not shutting down a thriving community and protecting the heart of a place that was supposed to be about little art projects and theater projects and music and all these creative things. We didn’t want everyone to just be flooding Kickstarter coming to launch their product. So, I think that’s what it was.
There was also, of course, a worry with these massive projects that make $1 million and promise a product–where’s the line of accountability for delivering?
On one hand, we were a platform connecting creators and backers and it’s on the backer to practice skepticism and look into something and not just click a button. On the other hand, there are lots of ways for us as people who are creating the product to enable and empower transparency and require creators to provide comprehensive information to their potential backers.
Craig: Especially when there was a sort of proliferation of Kickstarter-like sites. Was the product decision also about differentiation?
Cassie: I’m sure that came into the conversations, but I think the real driving goal was, “How do we maintain this potentially fragile artistic community? How do we not let these hardware products crowd ’em out, but also how do we respect those projects, too?” At the end of the day if a person is like “Me making this cool gadget is my creative endeavor,” is it really our job to say, “No, it’s not,” you know? That’s really hard.
Craig: Totally. Especially when you’re letting the community self-guide and it self-guides towards hardware.
Cassie: Yeah. I think anybody who’s running a digital platform will tell you it can be really hard to reconcile your original intentions with what your community uses your product for. When you make a thing and put it in the world, you do cede a little bit of control. But I also think, right now, the entire world is struggling to negotiate a new boundary line on accountability. It used to be considered very “cool” to let communities self-govern — but now people are (hopefully) starting to come around to the fact of that not working. Now, I think the new conversations starting to happen are about how to build morality, civility, and inclusiveness into a product. They’re about how and where to take a stand.
Craig: Were you part of the curation for the newsletter and front page of the site and that kind of stuff?
Cassie: I sent the newsletter for years, yeah.
Craig: How did you navigate picking projects when there are $10 million and $1,500 projects on the site?
Cassie: We always had to be really careful about selecting them. I think the most important thing that makes a good Kickstarter project is not how much money it raises or how much it’s trying to raise. It’s 100% about – and I know this is like a word as old as time in digital community circles – storytelling. Anyone who’s telling their story in a compelling way, no matter what they’re making or how much money they’re raising, if they’re speaking in a way that resonates, that is what matters. That was the intuition that guided me.
I didn’t want to send out a newsletter with four projects that were like $10 million each, because that’s insane. Then all the people getting that newsletter are going to be like, “If I want to make a project on Kickstarter I have to be able to raise $1 million and I can’t do that.” It was looking for the heart in things, really. There would be projects where a group of kids were making a record in their garage and raising like $5,000 and you’d watch their video and it would be technically “bad,” — but it would also be so charming and funny and reflective of the spirit of the project creators. And then maybe the rewards would be really tongue-in-cheek and you’d laugh out loud reading them and that is totally a project we’d put in the newsletter, because it’s about the people.
Craig: As you became bigger you were sort of hit makers, too, for the little guys.
Cassie: Yes, that’s true. We were turning a really powerful spotlight on these projects. We could certainly have the power to put somebody over the line on their funding goal.
Craig: Totally. So as you were at the company longer, were you involved in hiring people?
Cassie: I would say that at a very early stage, I’ll admit this, I was like, “I don’t want to be a manager responsible for people.” So I’d interview people, sure, but I’d never say that I felt like I was responsible for who’d be hired. I really dodged responsibility. I just wanted to hang out with the product and community. I wanted to spend all my time looking at projects, writing about them, getting into them, going to see them in real life, interviewing the people, curating, and I wanted to live and breathe that. I did not want to be thinking about office management.
Craig: So when you left, was your role similar to what it was in the beginning?
Cassie: When I left I was full-time managing projects, basically. My role had been so many things, that just happened to be what I was doing when I left. I went from customer service to being full-time project manager to being editorial manager back to managing projects because we were getting so many and we really needed people doing that. I was just like, “I’ll do it.” My role sort of did not follow the standard ascension that I think a lot of first employees might say. But there are a lot of reasons for that…
Craig: Full stop.
Cassie: I’m happy to talk about that, I just didn’t know if you wanted to.
Craig: [Laughter] Definitely! Go for it.
Cassie: I was not fiending for management and responsibility. In my head Kickstarter was not the thing I was trying to do with my life. I had all these ambitions like, “I’m doing Kickstarter until X time and then my life begins.” As much as I loved it, I was trying to just learn stuff, be immersed, do it. Afterward my life would really begin and it would be about me and the things that I’m meant to do. I did not reach for it there. But also I just hit a lot of roadblocks in terms of the functionality of the company itself.
Craig: What does that mean?
Cassie: I just don’t think there was an understanding of how to manage me. In other words, not having clearly defined goals, not getting feedback on things–all of those things that help somebody thrive in a workplace, I wasn’t getting and I didn’t know to ask for. I was too naïve to know what I needed.
It was kind of a negative feedback loop at one point where it was really frustrating, but I learned so much. Now I feel like every job I’m in I understand how to assess the environment and manage up instead of waiting for people to tell me what to do. I’m now very comfortable saying: “I’m not getting X in this environment” and then working for it. I can do that now and it’s fucking amazing. It opens so many doors. Wait, can I swear or should we cut that out?
Craig: [Laughter] Don’t worry about it, it’s allowed. I think if you did a text analysis I probably have like 90% of the swears and 10% of the words. I’m very efficient.
Cassie: [Laughter] My whole interview is just a series of swear words.
Craig: [Laughter] “I don’t know, she insisted on printing the eggplant emoji 100 times.”
Cassie: [Laughter] Exactly.
Craig: Anyway, if you were to be there again, would you change anything? How would you have applied those learnings?
Cassie: I think about this all the time. If I was to start over at Kickstarter knowing everything I do now, I’d just dominate. I know so much about how not to internalize external structural issues.. In the early days of Kickstarter, just because I didn’t know any better, anything going wrong around me, I internalized as: I’m doing something wrong, I’m a bad person. I think it’s a huge issue with people in the workplace, especially young people, especially young women. Learning not to do that, oh my god, I feel like I can enter work environments so fearlessly now because it’s not gonna destroy me if things are going wrong at the company.
I would come back with the exact same skill set, intuition, enthusiasm, drive, and dedication I had, which were all aspects that made me a really valuable person for the company in the first place, but I would just be able to separate my sense of self from my workplace and my sense of the workplace. I think I’d be able to get what I needed to succeed a lot better.
I think I would be able to better identify a path through the company. And I wouldn’t get tripped up by all the little things that tripped me up.
Craig: Like what?
Cassie: Like being so self-conscious and not knowing how to stand up for myself and not knowing how to identify structural issues. Not being able to identify what’s going wrong in the room and just fix it instead of taking it personally. I was too young, scared, and uncertain, and I would take a lot of things personally that I just didn’t have to.
Craig: Yeah, though a lot of that is unavoidable. Even if someone told you, like on your first day at Kickstarter, a list of things to think about and do, you’d still have to go through stuff to really learn. At least I have to to internalize things.
Cassie: You totally do. You have to live your experience. There are so many books and articles I’ve read that I thought I was understanding and then I just lived my life and I experienced some of the things that were addressed in it and I was like, “Oh my god, I now get this on a level that I did not get before.”
Craig: Yup. Though an active goal for me is to be sensitive enough to hear those ideas and try and make them click early, but it’s really difficult. I have yet to do it super well. Essentially like before you break your leg, listen to the person saying, “You’re gonna break your leg if you do that.”
Cassie: What I feel like I’ve kind of learned is that you can’t predict anything in life. You can only predict that life is unpredictable. All you can do is feel sure of your ability to deal with it. So my goal in life is not to go out and avoid breaking my leg. It’s just to be confident that my leg will heal itself and be okay. I’ve developed a faith in myself to get through things. So I’m less afraid of what might come that’s bad and I’m not avoiding that anymore. I’m just like, I’m going through this and if X or Y happens, I can deal with it because I have thick skin. Does that make sense?
Craig: Yeah. You’re also now just more mature and confident and you believe in yourself. When you said you were self-conscious, what were the things that were going wrong that you internalized? I’m asking because a lot of people that read these are in similar shoes as employees.
Cassie: Yeah. So, if I would write something and send it to somebody for feedback and they wouldn’t get back to me immediately or they would forget, instead of following up I would feel they thought it was bad. But the reality is everyone’s busy. Sometimes you just have to remind people.
Or when somebody’s in a meeting and they snap at me and I’m like, “Oh my god, it’s because they hate me and I’m doing a really bad job and I have to change everything about myself until I end up getting it right.” It’s like, no. Newsflash, no one is thinking about you. That is the truth of busy companies that are growing. No one is thinking about you. Who knows what is going on in someone’s life that they snapped at you? The best way to deal with everything is head-on and straightforward and just talk to people. If someone is consistently shitty with you for a week, for a month, you need to learn how to sit that person down and be like, “Hey, something is going on here. I want to get along with you. We both need to do it in order to do our jobs well. How can I make this better?”
Just be forward and offer to make change. Like 90% of people will respond to that with incredible gratitude because no one has those conversations with them. If you’re on the receiving end of it, it snaps you out of something, for sure. I’ve done that so many times where I’ve learned to get really good at sitting people down and being like, “Hey, what’s up with X?” People respond really well. I think everyone is used to getting in ruts of passive aggressive behavior, and if you address them in a kind, candid way, people want to come around and get along with you most of the time.
Craig: I have two questions then. One is, how does that effect you managing up, and also are there important nuances there for people to think about as a woman in the workplace? Especially in a tech workplace?
Cassie: So I know what I need to do well in a workplace–I need consistent feedback and I need excruciatingly honest feedback. I don’t want people to tell me things in a nice way. I just want them to be honest with me. So I feel like I have to be really forward about setting that precedent with new managers, where I coach them into not being afraid to tell the hard truths by reacting consistently positively when they have to give me hard feedback. People can be very afraid to tell you something they think you don’t want to hear, but what you’re telling somebody when you give them hard, honest feedback is: “I know you’re really good at this, so I know you can do better.” Which is actually very respectful. We’re just so conditioned to think that to be nice is the only way to be good to people.
With hard feedback from managers, my end of the bargain is that I can’t fall apart and take it personally and get emotional when someone says, “You can do better.” I take that as a sign of faith that they think I can do better, which is good.
In terms of being a woman in the workplace I will say that overwhelmingly more so than young men I talk to in workplaces, young women internalize the work environment and think there’s something wrong with them, and shrink and get stressed out. I just see them suffer from that. Every young woman I’ve ever talked to, I just try to break that cycle with them and show them how the issues they’re facing in the workplace aren’t their personal failures, but they’re actual structural issues. I teach them to build a wall between their sense of self and their idea of failure. Failure is such a constant and, like everyone says, you just have to roll with it. I wish there was a class called Failure where we just saw all the places in history where amazing, well-known people totally fucked up.
Craig: Totally. Ok, so then what inspired you to leave? What made the choice?
Cassie: I had hit a ceiling in terms of what I was learning and I got bored, to be totally honest. I felt like I had a lot of things I wanted to do in my life that I had shelved because Kickstarter had started to take off and became this really big thing. It was this whole crazy ride, but it was coming to an end for me, and I was ready to do other things. I just had stopped learning, and I was hungry for other things. I wrote an essay about it, actually.
I remember when I was making the decision it was really hard. I got off work on Rivington and walked all the way up to 87th street on the east side three nights in a row thinking about it before I was like, this is the right decision, and then I quit. It was like asking for a divorce. I’d just been through so much. I think every employee at a startup has been through that. There’s a golden age and then you bottom out a little and you hit the hard parts. I really struggled for a while with Kickstarter and I struggled through those hard parts and I got back on top again and got to a place where I was like, “I feel really good about my work again, I feel really good about my relationships here, I feel like it’s time to go,” and I wanted to go out on top. I didn’t want to quit because I was frustrated and struggling.
Craig: Then did you immediately leave New York?
Cassie: Yes. My mom works for an airline and I fly for free. The next day I was on a plane to Berlin for a job interview at Soundcloud, though it didn’t really make sense to take that gig, at the time. Then I went to Costa Rica and then I went to Europe and then Southeast Asia and I was just gone for about two years. I just left and didn’t come back. I worked remotely for myself.
Craig: What was it like leaving all of your friends?
Cassie: I wrote a lot of letters while I was traveling and I was really impressed and surprised by how in touch certain people were, like the people I would maybe least expect. I don’t know. I didn’t feel like I was really leaving anything behind. I would say it felt very good.
Craig: How do you feel now about Kickstarter as it currently stands?
Cassie: I don’t think about it anymore ever. I don’t know if there is some kind of filter on my computer that they’ve figured out, but I never see Kickstarter projects, I never get emails. It’s like it never existed in my digital universe at all. I never see it. Kickstarter is like my ex-boyfriend.
Craig: [Laughter] Unfollow.
Cassie: [Laughter] I’m totally over Kickstarter.
Craig: Did you ever see those UX of a Heartbreak gifs? Like the mutual friend count going up on your ex’s partner?
Cassie: I don’t think so…
Craig: They’re awesome. I’ll link them in the interview. Anyway, I’m sure there were tons of good moments at Kickstarter. Do you have any funny memories?
Cassie: Running the Shit Kickstarter Says Twitter before they made me delete it. I ran a Shit Kickstarter Says Twitter feed because we would say the most absurd things out loud when we’d be talking about projects, because it would be like, “We could build the Iron Man suit in the hamster farm,” but it was legitimately what we were talking about. It was just like pure gold.
The first year that we were a company we took a few long weekends together. One of those remains one of my top five memories ever. Yancey, Perry, and I went out early to check in to this house we had rented in Amagansett for all the employees to work from. I remember getting caught in a rainstorm, posting up in a pool hall, staying out late, crashing on deck chairs at a friends house, a million other things. Just beautiful wanderings and being so weird and silly. Things still felt very new then, like Christmas. The excitement and freshness was like that.
Then the first film festival, which was a real big achievement for us. The first time a project won an Oscar, and seeing the film in theaters. That was so exciting!
Then, there were all the times you’d meet somebody who you had helped with their Kickstarter project. Sometimes they would literally cry, because they would have connected you with this profound turning point in their creative career and you’re like, “I don’t deserve this at all. This is all about you. It’s absurd that you would give me any credit.” But knowing that there are thousands of people out there who have that association with you is really crazy!
Craig: I really enjoy doing these interviews because everyone is so completely different. It’s so cool.
Cassie: We’re all really the same.
Craig: [Laughter] Yeah, sorry. You’re all the same. Interview over. But actually, what’s next for you?
Cassie: I’m honestly not sure at the moment. My current job comes to an end in January and I’ve been really re-thinking how I want to spend my time. I’m looking forward to burying myself in new projects and it seems more important than ever to make sure I’m committing myself to civic-orientated work. There’s so much that needs to be done — and it’s really important that people my age are getting involved. So I’m pursuing any opportunity I can that puts me in touch with other young women who are out there trying to make it. I want to be a resource wherever I can. Right now, what we need is to be building support systems for each other — and I want to be actively working to help do that. That seems like the most important thing.
Claire Wasseman, who runs Ladies Get Paid, is really inspiring to me. So are people at companies like Nava and USDS who are using their technical skills to remake government services, like health care, for people. I also love the work of companies like Loyal (founder Sarah Judd Welch, runs an amazing newsletter, too), who are focused on building community in new and smart ways.
Craig: Anyway, the last question I have is are there any books or anything like that you would recommend people check out?
Cassie: One of the most educational books I’ve read about process has nothing to do with tech or startups or anything, but I read Robert Irwin’s biography.
Craig: [Laughter] It’s the book I recommended on the YC’s summer reading list.
Cassie: Wait, seriously? The Lawrence Wechsler biography, seriously?
Craig: Yeah, the conversations with Robert Irwin.
Cassie: Are you kidding?
Cassie: Really? I’m shocked. Reading that book is magnificent because you see his whole life, his whole creative process, everywhere he failed, everywhere he did everything right. The thing with Robert, is he just found his light — the thing he wanted to do — and he pursued it so deliberately, and with such devotion, and, often, without really understanding his own end goal. That was something that really resonated with me, the love of the thing, the process itself, matters most. Just get in there and do it.
Oliver Sachs has a memoir that I loved reading because he fucked up so much. So much. I remember one anecdote where he committed years to some early research — and in the final hour, he just messed up, I forget, but some tiny, seemingly insignificant detail of an experiment, and he completely fucked up the entire experiment. All of it had to go down the drain. But, you know, he still went on to become one of the most famous and renowned minds of his field. That failure was just incorporated into his life story, just like my failures — anybody’s failures — will be incorporated into theirs, if you just keep the right attitude.
Thanks to Fred Benenson for introducing us to Cassie.
Ryan was an early engineer at Salesforce and did Product/Partnerships at Twitter and Lyft. He now works at YC and helps people find jobs at YC companies — from 2-person startups to larger ones like Airbnb, Stripe & Instacart.
If you’re thinking about what’s next, Ryan’s here to help. Reach out at [email protected].