The Trailblazers Experience Podcast

EP79 Quinn Li O'Shea Founder & CEO BRAID; Building Connection in a Disconnected Workplace

• Ntola

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Summary

In this episode of the Trailblazers Experience Podcast, host Tola talks with Quinn Li O'Shea, founder and CEO of Braid, about the evolution of remote and hybrid work. They discuss the inspiration behind Braid, the importance of authentic connections in teams, and Quinn's journey through various tech companies. The conversation also touches on the challenges of fundraising, the dynamics of co-founding, and the significance of maintaining a work-life balance. Quinn shares valuable insights on communication skills, mentorship, and the future of work, including the role of AI in enhancing team connections.


Chapters
00:00 Intro
01:46 Building Braid  Start up journey
02:21 The Evolution of Remote and Hybrid Work
05:23 Braid: Enhancing Team Connections
07:53 Quinn's Entrepreneurial Journey
12:27 The Importance of Communication Skills
14:30 Navigating the Fundraising Landscape
21:30 The Dynamics of Co-Founding
24:48 Staying Motivated as a Founder
25:51 The Impact of Work on Customer Success
28:18 Celebrating Wins and Milestones
30:25 Finding Balance: Hobbies and Personal Growth
33:25 Pride in Personal Growth and Mentorship
36:49 The Future of Braid: Enhancing Team Connectivity
43:33 Trailblazer Takeaway Tips
48:41 Outro

Use code "TTEPODCAST  " for 15% off your first year with Braid.

Connect with Quinn Li

LinkedIn Quinn Li O'Shea | LinkedIn 

Braid Slack Games for Teams by Braid Social 

Watch on Youtube :https://youtu.be/tUsWohdn2A8




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Speaker 1:

Welcome to another episode of the Trailblazers Experience podcast, the podcast where we have candid conversations with women sharing their career journeys. Today, we're exploring innovation in remote and hybrid work. I mean, who thought I'd be talking about that even post-pandemic With someone who's not only a leader but a visionary in the tech space? Our guest is Quinn Lee, founder and CEO of Braid, a venture capital-backed company creating groundbreaking tools to help remote and hybrid teams connect, and she's had an amazing journey. I mean, if I look at her CV in terms of everything she's done, definitely one to watch A serial entrepreneur and looking forward to this conversation. So welcome to the podcast, Quinley.

Speaker 2:

Thank you so much, really excited to be here.

Speaker 1:

Isn't it interesting when someone is running down your accomplishments, you sort of have a moment where you say, oh my goodness, have I done all these things? Is this really me? You know literally who is she, who is she, but that's what makes you so brilliant. And the great thing is, I think, with podcasting is you get to inspire. There will be someone out there just going to say wow, Quinley, I never thought about this. This is an opportunity for me to start something.

Speaker 2:

Hopefully and I will I'll do my best to try to bring in some like unique perspectives, things that you can't just find if you Google or search them on Medium, because I feel like.

Speaker 1:

That's why everyone's here. So, quinley, let's start with braid For me. Obviously, I know braids in terms of braiding your hair and everything that has to do with some great hairstyles. What inspired you to create the platform, particularly focusing on remote and hybrid teams, especially when we well, the majority of companies are saying get back into the office, whereas actually there are more companies that are embracing, thankfully, this new way of working, this new way of connecting, this new way of, you know, increasing productivity and making people perform at their best. Where did this all start?

Speaker 2:

Yeah, absolutely so to your point.

Speaker 2:

There's a lot in the news right now about you know. Companies are mandating RTO. They want people in the office three, four, five days a week. But what's really interesting is, even though, while companies can say that, what has happened with most of their workforces is that they are more distributed. So even if they have offices in London, in New York, in Seattle, whatever the people who are in those offices still need to work with people who are not physically located in that office. So one of the things that we're seeing, even with the in-person companies, is that people go in to the office, they're on their computers and then they're spending most of their day on Zoom calls with people in other locations.

Speaker 2:

So I think the definition of in-person or even hybrid has changed a lot over the last five years. And then I think a lot of companies are, even if they have those policies, they're more like future-looking goals where the actuality the day to day because, again, teams are made up and companies are made up of people People have different circumstances and the companies still want them as employees. So what often happens is they would like people to come back to the offices, but most people are working from home two or three days a week they are calling it from a family trip or they are just, you know, traveling for that month after various circumstances, and the companies are still fine and pretty, I'd say, flexible when they're when there's some trust with their employees or there's different circumstances. So for us, like we do brand ourselves, as you know, this is for remote and hybrid companies, because I think the companies that are more zoom first, are more Slack first, are our main customers. That being said, kind of the inspiration behind Braid was and this is, I think, good advice for most startup founders take an existing problem or experience or something that you're already doing and see if you can enhance it. And so, across my entire career and again you mentioned some of the companies that I've worked at but startups, big companies, small companies, post IPO, pre IPO, etc.

Speaker 2:

Like all the companies where I've worked, teams have always struggled to find ways to connect that feel authentic and that aren't forced and that also don't take up a lot of time. I think this is an age old problem. There's a constant balance between we need to get our work done and you know, we have to hit our deadlines, we don't want to be too distracted, but also, I'm trying to collaborate with you and I'm trying to ask you questions, but we have absolutely no rapport and no trust, and so there's a very, I'd say productivity oriented purpose to let's find some time to connect, let's get to know each other, and I've teams that I've been on throughout my whole career have struggled with that, because it's hard to find that balance, and Braid is really trying to answer that initial problem in the market of how do you connect with your teammates in efficient ways that aren't too expensive or too distracting from the core work that teams need to do.

Speaker 1:

I mean that's brilliant, but for audience at a simplistic level. If they were to say, right, we are looking to utilize Braid, what would you do for them?

Speaker 2:

Yeah, absolutely so. Depending on how big the company is, either I would get on a call with somebody who maybe runs their HR function or people experience, or, if you're a smaller company and you guys are pretty self-serve, you could just go to Braid's website and install our Slack app and what that'll allow people to do is literally within any channel. Within Slack you can set up a game within a couple seconds. If you want to personalize it, make it customized to the team. So maybe you have a new teammate and you want to make some trivia about them to help everyone get to know them better as part of their onboarding.

Speaker 2:

Somebody can do that within maybe two minutes and then schedule that or play it immediately, and it's a really nice way to build these kind of connection rituals. That, again, it took a couple minutes max to set up and then everyone within the channel can play. And if you wanted to roll it out across multiple teams or you wanted to build kind of a longer term journey with experiences across, you know, the next 30, 60, 90 days, that's usually where, if you're at a bigger work like that, I would work with you to help set that up. But again, set up can be super quick and it's just a way to. How do you provide these? We call them like scalable connection experiences, where it only takes a few minutes, but if you do it for a month or you set a schedule for a couple of months, there can be really meaningful changes in terms of how teams interact and get to know each other.

Speaker 1:

I think it's such a brilliant idea because when I think of how sometimes some organizations just you know from studies and researches that I've seen as they've tried to instill that through using WhatsApp and you know we're not affiliated or promoting WhatsApp in any way but there's that blurred line because WhatsApp is actually more personal and actually, if you can then create those, you know, gamification or experiences to connect people within a work environment on a workspace work app, I think it's a good way to separate it as well. So you're doing it within the Braid environment and just, yeah, I feel like a separation of the two, but still connecting people in that way as well. Yeah, yeah, exactly. So let's go all the way back.

Speaker 1:

I mean, you've had an impressive career with roles at OpenStore. I mean you've had an impressive career with roles at OpenStore Squares, you know to name a few. How did those experiences shape your vision for Braid and, I guess, just your approach to building impactful products? And where did this even start? I mean, have you always had a knack for new businesses, new ideas? This must come from somewhere.

Speaker 2:

Yeah, I laugh a little at myself because I think when I look back at younger versions of me, I don't think I knew what I was doing. I think I was just intrigued by either working with specific people or just had passions that I wanted to explore. My first, I'd say, entrepreneurial endeavor was actually in high school, where I started a fashion blog with a friend and then it turned into kind of this fashion flipping business where we would sell the clothes we were wearing, and then it became an early affiliate kind of marketing influencer, and this is early days of Instagram. So before influencers grew into what they are today, I kind of just built this from the ground up in high school because I wanted a way to show off my style and show off my friend's style that also makes more money, so I could buy more clothes, and that grew decently for a few years before I sold it. But I think I have always had a passion and maybe an inclination for like, passion for building and then an inclination for doing so. It's like, oh, like, I want to try this. Let's, let's, let's set it up. And I think through the years there have been a lot of failed projects and initiatives as well. Not all of them were successful, not all of them scaled, but that's part of the learning process.

Speaker 2:

And then, more tied towards my professional kind of employment history, I think there are so many learnings. One of them was that you don't need to be technical to have a really large impact on software products. I think a lot of people, a lot of women, trying to break into the tech industry or trying to move more into, like, a decision-making position, doubt themselves because they don't have that technical background. Honestly, if you can communicate and translate and break down problems in a way that non-technical and technical people can understand Like as a product manager, that's 50% of my job is just communication and making sure everyone in the room can understand. Why are we building this? What do we want to build? No technical jargon needed.

Speaker 2:

I think another learning that I've had that has definitely helped Braid is the hard skills, or maybe medium hard skills, of building a product, of launching one, of marketing one, of doing retention and scaling an audience. A lot of those, once you learn them, are really applicable across different products. So I've worked, as you said, in gaming, in e-commerce, at FinTech and I worked at a coffee company for a year, I'd say the skills are really similar in terms of what you need to maintain and build a product. And then the different thing is the domain knowledge of, like, okay, what is unique to gaming or what is unique to coffee, but assuming you're not doing it totally solo, and even if you are, there should be connections that you have that you can reach out to, they can interview, they can shadow, and so I think if there is a space that you're really interested in and you don't have the domain knowledge, as long as you kind of know some of the steps of, okay, here's how I get started, here's how I launch something, here's how I'm going to engage them.

Speaker 2:

And, if I'm being honest, there's so many great founder blogs about this and ChatGPT is also really good to help summarize if you're just looking for a place to start.

Speaker 2:

So I think those were two learnings for myself that when I was evaluating, you know, should I start a company, I could kind of fall back on. Look like I know how to build a product, I know how to launch one and you know what the stuff that I don't know we're going to learn along the way. That, I think, gave me the confidence to embark on this founder journey and then in terms of, like, the specific domain of building for professional teams building on the platform, so Slack and Zoom that they already use I'd say my whole career using Slack and using Zoom and then using other tools really helped give me, I think, kind of that North Star sense of where should we start to help teams build connection, because every team that I've been on kind of helped influence the decisions that we made as we brought the products to market, as we formed the vision, as we designed the platform.

Speaker 1:

I mean, girl, what you've just summarized should be taught at universities, because you've just really distilled. It's interesting. A lot of businesses are always yeah, what problem are you trying to solve and you've nailed it on the head in terms of what are the transferable skills that are agnostic of whatever industry or sector, that can be applied wherever you go, and just having the confidence as well to distill that information for board level to understand, for non-technical people to understand, because you want, ultimately, everyone on the journey with you. And if you cannot explain it in the simplistic terms, then there is a problem even in terms of getting investment as well. So that's not something one learns easily. You know that's your secret sauce in a way, don't you think?

Speaker 2:

Maybe. I definitely think strong communication skills are really important, but what I can say is I'm an extrovert. I love talking with people. I know a lot of really effective people in business in my career who are not nearly as extroverted and they are really effective via slideshow presentations or just going to Google Docs and they have such clarity of thought and how they break things down. And so I think there's also a really important call out there where it's like if you're not, if you don't love chatting, or the idea of getting up in a boardroom or a big presentation or presenting to everyone freaks you out like hey, that's normal, it's not a natural way of communication.

Speaker 2:

You get a little less nervous with reps, but also there are many ways, I think, to be really effective. Again, even if you're just like really good at using Slack or Microsoft Teams whatever the internal communication tool is at work like, you can be really effective. But it's back to what you were saying, what I was saying earlier, anjola, just around, just make sure your audience is understanding you. It doesn't have to be a great speech. It doesn't have to be an impressive, like super impressive deck with lots of graphics and tons of images. It's just like make sure the audience that you're targeting understands you and use channels that you're comfortable with, that or that show kind of your strengths.

Speaker 1:

Let's talk about investment and, obviously, starting a business. You know having that idea is half the battle. Then obviously, the execution. What do you think are some decision points or things you can share that have been helpful in terms of A the challenges you've faced in securing funding and, you know, fueling your business, but steps that you've taken that have sort of helped you on this journey?

Speaker 2:

Yeah, yeah, okay, it's a great question. So I think one of the biggest unknowns for me going into founding was actually fundraising. Like I've built many products before, kind of at all different stages I've pivoted business models and helped turn around teams and businesses that are struggling. That's a little bit of my specialty historically, but fundraising was like a total black box to me, and so I think the first thing is like get as much advice and help as you can, and so look for or start following if you're thinking about fundraising on Twitter, honestly, and a little bit of LinkedIn, but mostly Twitter follow big name VCs, see what they're tweeting about. Look at some of the founders who have recently raised from companies that you might want to raise from. Follow them again on Twitter.

Speaker 2:

I'm not the biggest Twitter user, if I'm being honest, but I was on Twitter a lot more when I was learning how to fundraise, because there is a language, there is kind of like an osmosis learning that happens just by kind of being in the space where the people who are doing these deals are. And look, if you live in Silicon Valley, if you live somewhere like where there are a lot of VCs, maybe just go to the coffee shop and hang out and just listen to them. What they're talking about, the deals they're talking about, how they talk about valuations Podcasts are also great for that. But again, if you don't have proximity or maybe you don't have time to listen to a ton of podcasts, I think just getting online, seeing what the VCs are talking about, get on a few different newsletters, recent deals that have happened, so you can kind of have a sense of like, what's going on in the market, and then it comes down to like your actual pitch. So how are you pitching your company? And I think how you pitch it.

Speaker 2:

Usually if it's your first time pitching, it means that you're pretty early right. So if this is your first time getting investment for the company, maybe you have a couple customers, or maybe you have a proof of concept, or maybe you just have an idea and you need some funds to hire someone to go build the idea. So this advice is going to apply to that. If you are in this weird case of like I've built my business up solo and I have a couple million dollars of revenue and I've never taken outside funding, but now I need it, I'm not gonna lie, you're not gonna have a hard time pitching. So, like you, probably don't need my advice. So if you're in that early stage and you're just getting started and you're really trying to get investment, I think let's see.

Speaker 2:

The first thing that you should do is write down and ideally you have a co-founder or a friend who knows what you're working on that can help you with this. Have them ask you, like, what makes your idea special, what makes your quote-unquote company and I say quote because maybe it's not a company yet, maybe it's literally just you but what can you say that, in theory, very few other people can say? Do you have an incredible background in this field? Or do you have close proximity to a couple family members who are really impacted by this problem that you're trying to solve? And that's why you are more motivated than anybody else to solve it? In terms of the product, again, it might not be that out, but what's unique about how you're thinking about solving the problem or what unique skill set or insight do you have? Those are the things that you're going to craft your initial pitch around.

Speaker 2:

And then I think, very tactically, in terms of getting investment, your network is like the most important thing in terms of getting in front of people who might be in a decision-making position to give you money. So, if you don't have that network, start connecting with people on Twitter and LinkedIn. That's where these people are looking, or investors are potentially looking for connections or inbounds. If you do have people within the tech space who might be investors, grab coffee with them, ask them if you can chat, get some feedback on your pitch and then ask them who they would be willing to intro you to. You should have a blurb or like an email, with a couple bullets of willing to intro you too. You should have a blurb or like an email with a couple bullets of hi, my name is X. I'm building X, y and Z. Here's why it's amazing. One bullet, maybe two, and then last bullet should be what you're looking for.

Speaker 2:

So, exploring an early pre-seed raise, would love to chat or, you know, started kicking off our raise and expecting to close by August of this year. So this is a bit of a okay. When this gets forwarded to other people, they expect what to do. And then from there it's just and I say just, but it's once you are comfortable, you have your story, you start crafting your pitch. I like to pitch without a deck. Some people prefer a deck. Regardless, you should be crisp on again those things. What makes you special? Why should somebody give you the money? What is your vision for the company? And I think my overarching advice in terms of pitching and crafting this stuff is as the builder, as the maker, as the person who's like this is my baby. It's just a natural inclination to get way too in the weeds, where you're like it works like this and it does this thing, and in the future it'll do this cool thing.

Speaker 2:

Somebody who's an investor, think about it. They want to make money off of your idea, so you need to sell them on the opportunity, like financially. Why is this an exciting opportunity for them? Is the market huge? Is this technology wildly disruptive? Is this going to save businesses?

Speaker 2:

A need of $50,000 to $100,000 at some recurring cadence, because that's what gets investors' eyes to light up and be like oh, okay, so wait, you're qualified, you've got this cool idea. The market's really big, oh, and then here's all these potential dollar signs. Okay, yeah, this totally makes sense for me. So advice on the pitch is like focus. Put yourself in the role of an investor and again, if I'm being honest, chatgpt is great for this. You can prompt it or any of the other AI tools and just say, like, pretend to be an investor. You know, help me format this pitch, but yeah, just I think always think about who your audience is, and for investors it's they want to make money, they want to give you money and get a return on it, so how can you sell them on the opportunity?

Speaker 1:

I mean, you've given some amazing tips and nuggets there, and the one that stuck out that I had a conversation with someone about was go where they hang out. So like even here in the UK, if you're in London or Manchester or the different key areas, there are certain coffee shops where investors go to hang out, there are certain coffee shops where the tech crew hangs out, there are certain coffee shops where fashion music and it's getting in there, because that's where you spark those conversations as well, or you'll be listening while they're chatting and getting in that zone. It's half the battle, isn't it being in that area if you're not in Silicon Valley as well.

Speaker 2:

Yeah, totally Totally. And I think, if you're not sure, again look up where their offices are and then find the nearest coffee shop or the nearest like lunch spot and just hang out there and, worst case scenario, you bring your laptop, you spend an afternoon, you got a sandwich somewhere, but maybe you overhear a really good conversation. Or, if you're brave enough, you go up and say hi and introduce yourself and establish a connection.

Speaker 1:

Yeah, what's important to you. So I've just recently seen Forbes in Europe has released their 30 under 30. And you can see that some businesses are solo founders, so they're solo CEOs, solo founders, and some have co-founders. What's been your approach? What's worked for you, especially with Braid?

Speaker 2:

Yeah. So when I founded Braid I had a co-founder. I always said, at least for my, my first, like my own venture. I did not want to be a solo founder. I've seen how hard it is on people. It's really lonely. You don't have the strategic counterpart to bounce ideas off of. You don't have that person that you can acceptably paying at like midnight when something's not working and be like, oh my gosh, how do we fix this together?

Speaker 1:

as well, isn't it yeah?

Speaker 2:

yeah, um, the co-founder and I did part ways around a year ago, totally amicable. I think we had different creative directions in terms of where we wanted to go with the company. And then, if I'm being super honest and this is something to think about if you're thinking about founding, or maybe this resonates if you're already in a founding position uh, I think our skill sets were too overlapping.

Speaker 1:

And so what?

Speaker 2:

I mean is their background is in data science. I'm not a data scientist, but I did have to be my team's analyst and so I am pretty analytical. And again, when you're just getting started, you don't need a ton of data science-y work. You know, I wanted them to lean more into kind of an engineering role, but then, for various reasons, they kept leaning more into like a user researcher role, which, again, that's more of my background. And so I feel like we just kept overlapping.

Speaker 2:

And then it kind of was in this weird place where it's like oh, the co founder is doing some of these things, and then Quinley is doing some of these things, and then we're not, like, we're not meshing and there aren't clear lanes of ownership. And again, when you're only a two or three-person team, you need to have a lot of trust and also clear lanes of like I'm going to go here, you're going to go here, we're going to check in with each other, we're not going to just go in a silo, but we shouldn inefficient. And so, yeah, I think we both had a lot of respect for each other and really trying to find ways to collaborate, but when it came down to it, just our skill sets were so similar that we weren't able to carve out different parts of the company and I think that created a lot of tension. And he very graciously acknowledged that it wasn't working and was also interested in pursuing kind of more of the social route of tech and so stepped down and it was an intentional choice for me not to bring on somebody else.

Speaker 2:

The team was me plus two other people full time and a few different contractors and I just felt like you know, let's, let's see how things land and then if there's a need for somebody else I'll bring them in. But you know didn't want to. I wanted to kind of like stabilize and normalize how the team would work, with just me leading the company, and then it's been working well so far. So at least as of now I'm like you know what, no need to bring on anybody else, let's save that equity and let's save that headcount for when a clear need arises.

Speaker 1:

I mean, you know, it's brilliant, and thank you for being so honest in articulating that, because sometimes you just need to make decisions at the right time and if things aren't working, it's time to move on and get on to the next chapter. And it's, you know, it demonstrates leadership skills as well, isn't it? You just say right, it's time to also make a decision and move on in different directions. Staying motivated, and what inspires you? How do you fuel your own growth? Obviously, you're very passionate about the ideas and the businesses that you're in, especially Braid as well now with the direction it's going and a great problem you're solving. But how do you stay motivated? How do you? You know where's the? Gives you the fire in your belly to keep going.

Speaker 2:

Yeah, I will answer that and I'll preface it with like this is not unique, I think to me, and I think I've heard about this spoken about at least in one other blog or podcast. So preface it with that it's not unique. But when I heard this it really resonated and I think it sounds so cliche. But I think builders, founders, people who want to create something, it's like, yes, money can be a strong motivator, but the thing that keeps you motivated especially in between getting different deals or assigning big clients is really the being able to see the impact that what you're working on has. And I think that in a large company right, your impact might be more limited to your immediate team or another team that you're supporting. And that was definitely the case when I was at a big company like Square or Zynga, where it was like I'm working on a small piece of something and that's going to feed into another piece of something that's slightly larger and eventually it's going to get to the customer. But just being able to see the impact of like wow, I helped make the customer success teams experience much easier. I was able to help them be more efficient. I was able to support this really cool kind of technically intense project at Zynga that they weren't sure how they were going to get it out and I was able to help them do that and, like, I see their wins and successes as like, hey, that's impact that I had and that really motivates me and I think people in general they want to be helpful, they want to have impact. So at bigger companies, that was really motivating.

Speaker 2:

And then at smaller companies, it's pretty awesome because you can see your customers. As a founder, you have direct access to your support chats and they're experimenting with the product. And then they kind of just get distracted and they start having fun playing a game with each other and they're laughing and they're chatting and then they're like, yeah, this is going to be great for the team and you can see it in their eyes. You can see how excited they are to roll this out to more people within their company because they're like this is really going to help and benefit people and help bring everyone together. Just being able to see that and witness that is so motivating.

Speaker 2:

And yeah, if you're not getting that again, reach out to your customers, ask them, ask if you can shadow them, ask if they're willing to chat for 30 minutes and literally just having like being able to see the impact, I think is so motivating for many individuals. Obviously, the more the better, right. But like, if you're getting started, like you know, take each one for what it is. If someone's like this is really awesome and like I shared with four friends, like that's huge. So, yeah, I think it's seeing your impact. And even if you're not in a startup, if you're at a big company, it's finding ways to connect back to, like the impact you're having. And that's a tip for leaders too where it's like, oh, the team feels a little disconnected or they're not sure where they're going. If you have high conviction in the impact of what they're working on, help find ways to surface that, because that's a really great and like objectively free way to help motivate and connect your employees back to what you're working on.

Speaker 1:

It's a lot of it, isn't it? There are those you talked about non-cashable and then the cashable benefits. But your customer, whether it's your internal customer, so your team or external, the consumer, whoever's using the product, or your supplier, it's so important to have those conversations and I like your thing about taking each win, isn't it? You have to celebrate each step that you're making in the right direction, progress, each new customer you brought on, and just seeing those reactions, because sometimes you can be so fixated on the end goal that you actually forget to enjoy the journey and appreciate those milestones that you're making.

Speaker 2:

You know, I remember when I was in more of an operations role. It's sometimes not even that, you know, you get so lost in the vision or you get so stressed by something, but sometimes you're just so busy and at the end of a month or a quarter you're like God, I am exhausted and like, but then you don't remember to circle back and be like OK, but wow, like, look at everything that I helped enable, look at all the impact that I had.

Speaker 1:

I mean that that is so true and in a world where everything is supercharged and super fast and results now, and just taking that, that step back, how do you unwind outside of work? You know, obviously, you're very driven, you have a great skill set, you're great at you know businesses, and that entrepreneurial spirit really shines through. What are some things? Because what I want to make sure, as our audience appreciates, is you know your career, your business is one thing, but making sure you are able to find those nuggets outside of that to help you. Now you might say, girl, this is my personal and my professional, but what are the things that you think help you outside of that to give you that zest to keep going as a leader and entrepreneur?

Speaker 2:

Okay, I think the audio cut out for a second, but I believe you were asking about hobbies and what I will say and you acknowledge like I might, as a founder, be like I have no free time or whatever. That is absolutely not me. I have always been somebody with a lot of hobbies and side projects and I find it really energizing um, I know, not everybody unwinds by doing, but I actually find it really therapeutic and cathartic to uh, I play tennis a lot and I think physical health is really important, but then also like creative or just like having a mental reset, is also important. So I play tennis a lot. I do aerial arts. So if you've seen like the silks and stuff hanging from the ceiling, like it's a, it is a great way to physically get a good workout. That also mentally, just like totally clear your head, because when you're hanging upside down and trying not to fall from like your ankle or something, you don't think about anything else. It's great. So I do those every week, multiple times a week.

Speaker 2:

And then I've always been pretty artsy and so I like to watercolor paint. I sometimes oil paint when I have the space and the time to do the full setup. I do different crafting activities and I like floral arrangements, like there, that I have a lot of creative pursuits. And then also I really like people and communities. So I try to see at least one or two friends a week, even if it's just for a quick hey, let's go for a walk or let's both walk the dogs or something.

Speaker 2:

I think just being in touch with people that are outside of the immediate startup realm it's also really important just to like ground you and remind you that like, hey, the world exists, there's so many great things, so big, big fan of having just different creative pursuits and making time for them.

Speaker 2:

And I think I've learned the hard lesson several times over that if you don't invest in those and it's fine if there's like a week where you have a bad week or you're traveling and you're at a conference and you don't get to do workout or see your friends, like yeah, but just then catch up on it the next week, because I've definitely skipped out on that before and what it usually results in is you get burnt out and then you are really inefficient at work and then you have to do a hard reset and that's not productive for anyone. So I think you're, long term more productive if you carve out time for the resets, for the relaxation, for the hobbies that recharge you and if that hobby is literally staying at home drinking tea and like reading a book or hanging out with your pet or just taking naps, like that's also extremely restorative. It does not have to be super active.

Speaker 1:

Yeah, I was listening to a podcast by Trevor Noah called what Now, and he was talking about how sometimes just being like doing the most mundane things bring actually the most joy and allow you, just being like doing the most mundane things bring actually the most joy and allow you just to, you know, tap into those creatives, Because I'm sure while you're having those personal moments, that's probably even sparked the ideas for the games that are on Braid as well. Yeah, totally. So, reflecting on your journey, which I don't think has come to any, you know, pinnacle point, there is still a lot that's going to happen in your career and so on. What are you most proud of and what are some of the lessons that you've that you've learned so far that you're utilizing now with Braid?

Speaker 2:

It's a really good question. It feels cliche to be like here are all these milestones that I've hit that I'm really proud of. I was a straight A student. I love the external validation, the checkboxes, but what I can say is like they do the same way. Like if you got an A in your class I don't know freshman year of college you worked really hard for, and then you got a couple B's and you got another A sophomore year or whatever, A couple years out of undergrad you don't need, I don't want to say you don't think about those A's because you did work really hard for them, but like those might not be the things you're most proud of, and so I think that definitely resonates for me where it's like there there's so many accomplishments that I am extremely proud of and really grateful for.

Speaker 2:

But I think the biggest things are probably more about, like personal growth. It's like I do think like I have been burnt out. In the past I had a very I think, old school, millennial, I don't know outdated mindset around like work hard and like grind, grind, grind, grind, grind, and I'm actually really proud that I've been able to accomplish as much as I have been able to in the last couple years, but without embodying that, with being able to still have hobbies and being able to connect with my friends and have a social life and a romantic relationship and a successful company. I think the personal growth that it has taken to be like nope, and the self-restraint and the skill amassment of like we're going to work here, we're going to take breaks here, we're going to try to find a way to make it more connected and holistic, I think that's probably one of my biggest personal points of pride.

Speaker 2:

And then I think the other times that I've felt the most proud are when, again, it ties back to impact, and I won't mention their names, but there are a couple key individuals who I know I've had a very outsized impact on their careers in terms of mentorship I provided them in terms of referrals and helping them get their foot into specific jobs or industries, and I think those are the things where it's like I see the kind of life impact that I've had on them and I've definitely had mentors and past role models who've had that impact on me, and so I think those are the things that I'm the most proud of.

Speaker 2:

I'm like wow, like to your point, I'm still pretty early and I have a bunch of things that I still want to accomplish in my career, but to be able to have kind of a life changing impact on someone's career and trajectory, that's yeah, those are. Those are probably the moments where I'm like, wow, that's really cool and I'm really proud of that, and I don't know how to replicate it. It's not necessarily my goal, but it's really awesome to be able to have that kind of positive impact on someone.

Speaker 1:

Yeah, there's something about paying it forward. I always say my measure of success is when someone in my team is ready to go and spreads their wings and says, right, I'm now leaving to go do something else elsewhere. That's actually the best measure of success, because it means they've discovered who they are and they've discovered the next stage, that they need to go. So you know, and seeing them succeed outside of that is, for me, it's yeah. You can't even compare the joy and how proud you feel as well. Yeah, what's next for Braid? How do you see the platform evolving? What are you working on right now that you can share, and how do you think it will help the way teams work together, especially as the working environments are evolving?

Speaker 2:

Yeah, totally, it's a great question. So right now, most of our games and activities are just purely within Slack. I think we are probably going to try to stay embedded on existing work platforms. So, expanding to Zoom and Microsoft Teams maybe Google meets, but honestly, google isn't. If Google wants to change their platform restrictions, I would love to build more products on Google. But yeah, I think it's core to our mission is like we don't want to distract people. We don't want to add another tool that you have to roll out and then now you're on multiple different platforms. I think that's really distracting to connection.

Speaker 2:

So I think expanding the different platforms we're building on so it's easier for users who aren't just on Slack and Zoom, I think there have been as we've been growing. We were kind of like, hey, we just want to inject moments of daily connection, but there have been some very clear use cases that have come to light, onboarding being one point in employees' journey that's really important for connection. I think people leaving a company or having a transition is another one that we've been really looking at, and then I think also trainings, learning and development. All of those are kind of key moments where there is an initial goal like get set up to work or make sure your transition off of the team is really smooth, or hey, we legally need you to ingest this material. But if you can add a layer of connection and make those kind of socially connective times where you also achieve the goal, I think it's just a net positive for kind of everyone the company, everyone involved. And so thinking about how do we enhance connection in these specific use cases is probably what we're going to be spending a lot of our time on this year.

Speaker 2:

And then I think you kind of hinted at like oh, especially with like different things happening. Obviously, like we're pretty late to the podcast, but I have a tech founder, so I have to mention AI. I do think AI in the workplace, especially with something like HR and people and connection, I think it's an interesting use case that we are exploring. And I think the ability for AI to kind of for you to tell it what to do and then you can set it and not forget it, but you can kind of monitor it and just watch it I think there are some really interesting use cases and applications here in terms of helping connect people, maybe with things in common, or hey, there's a need that I have. Who can help me with this at the company? I think ai has some really interesting implications there of how it can help better facilitate connections within companies, and so that is something we are exploring, and I think the last thing I'll say on that is the other thing that has been very topical of late is kind of the next generation of labor, so you know, millennials.

Speaker 2:

When I was starting my career, everyone was kind of dumping on us and saying we were really different.

Speaker 2:

And now Gen Z is coming into the workforce and we also still have boomers in the workforce, and so now we have three, maybe even four generations in the workforce right now and there are very different cultural and kind of like ideological differences. And so I think we do need to think about, when we think about connection, it's not just how do we connect with people who are our age group or, like all of us, who all work in tech or have been in this specific demographic our whole lives. It's how do you help connect these different generations at work and how do you help them be the most cohesive, high-functioning teams versus like, oh, management is older and they're stuffy and they don't know anything, and then the younger generations are like rude and they're lazy, or whatever the normal dichotomy and discourse is. It's like how do you break that down and actually make a really productive unit out of it where you get the best of all the generations and all the people that you're working with?

Speaker 1:

Yeah, there's a lot about the intersection of AI and connectivity and automating and making life easier. But yeah, to your last point about you know having all the in the same way, that there is neurodivergence and everyone has a different way of thinking, working, processing data, information, communicating it's how do you bring those different groups together as well, whether it's through technology, whether it's through practices in the workplaces. There's a lot going on and I love the fact that there's that awareness that not everyone is the same, but we can find common grounds or ways to make life easier to be more productive in the workplace as well.

Speaker 2:

Totally, or even just translating yeah, I don't know. There was a funny HR discussion recently about somebody, I think, in a workplace had like someone younger had said like she ate, and it's a Gen Z slang to be like oh my god, they killed it. They did a great job. Like, oh, like no, yes, yeah, yeah, literally. And somebody else was like they what? And this was like, I think at a google doc.

Speaker 2:

People were going back and forth like no, no, no, like the presentation, and they're like wait, like, so, she like, and I think the millennial phrase like you ate shit, which means like you did not do a good job, you crashed and burned, uh. So they're like what do you like? Sorry, like do we need to have a conversation about this? So there's just like a really funny just like, no, like wait. There's just like a young employee trying to say that so-and-so did a really good job, exactly, but that's like collectively, 15-20 minutes of the team's time was taken up on explaining this and someone was like wait, like, are you insulting someone openly? Like you know, this doesn't need to be escalated. Yeah, yeah, exactly. And I heard about this and I was like man, yeah, I could totally see this happening at certain organizations, if we can help build tools to help prevent that and help save people time. So there isn't 10 people suddenly being like what's going on? Like wait, whoa yeah.

Speaker 1:

And also, you know cultural gaps as well, isn't it? If you've been raised in different cultures and ethnicities, there's certain things that you might find hilarious or interesting, that another group would be like well, what do you want about? What are you talking about? So, it's, yeah. How can we, especially in a remote, hybrid way, bridge the gap with the tools to help us and not escalate what does not need escalating? Yes, we're coming to the end of the podcast. Quinley and I always end the podcast by asking our guest to tell us three trailblazer takeaway tips that they'd love to share with the audience to help them along the way.

Speaker 2:

Yeah, I should have prepped. I read them and I was like, oh okay. I think the top one is trust your gut always. This doesn't mean just in business, I think it's also like in life, but especially in business. Like if you feel like it's a great opportunity and you're really excited about it, and like you've done your research, like go for it, why not? Like you can always switch jobs you could like professionally, there aren't that many things that you can't roll back. And if you can't roll back like a big launch or something, presumably you're working with other people who can kind of counter you. But for the most part, like, trust your gut. There's so many times where I'm like this feels risky, but it feels like the right move to make, and then a few months later I'm like, yeah, that was the right move. So definitely trust your gut.

Speaker 2:

I think the second one is leverage your network. Like even if you're like I didn't go to college and I have no network, that's not true. I'm sure you have tons of people around you who have worked on really cool things, who might know somebody who's working on something that you want to get involved in, who can help refer you literally, especially right now where applying to jobs is really hard and AI has kind of clogged all the normal channels of outbound and emailing and applications and stuff like your network and who you can trust or who you can rely on to just give you a referral. Probably your most valuable asset right now I think it's definitely one of my probably my most valuable asset it's just who can I reach out to to get a referral, to get have a sounding board, to ask them for advice or to get I don't know, just a different perspective on things. So network, network, network, but do it authentically, you know, like don't, don't be like, hey, this random person who I've never talked to. I want to be your friend and I need your help, like, no, like, get to know them a little bit, ask about them or leverage the people where you do have some underlying rapport and connection. And then the third one is learn from the mistakes and failures. Successes are really fun too. It's awesome to be doing well and you're like this is amazing. But I actually think some of the best learnings come from when things didn't go well, and it does take.

Speaker 2:

Usually you need a little bit of time after something doesn't go well to process the emotions, but then sit down and kind of ask yourself there are a lot of frameworks for this. You can do five whys or you could just say kind of like what happened, what were the key events, what were the timelines, and then start asking yourself like what could we do differently or what could have gone differently, what would have helped? But I mean, our brains are literally biologically programmed to remember painful things and negative things more than they are to remember positive things. And that's because we want to protect ourselves, right. We don't want the painful thing to happen again, we don't want the negative thing to happen again.

Speaker 2:

But for most of us we're not, you know, we're not physically at risk most of the time. It's so the things that we're going to latch on to are like the painful things that work, the painful things that happened with our projects and I don't know. I think the most learnings are there to be harvested and really like help you cement, kind of how you do better next time and don't let them get you down, don't let them drag you and be like crap, that didn't go well, like I'm done, I'm just done, like there's nothing left for me, like look at it as a learning opportunity and be like how can I improve for the next time?

Speaker 1:

Winley, you have such a high level of self-awareness and wise beyond your ears. With that last point, I mean that's just even a mantra for life in general. It's been a pleasure learning about your journey and hearing your vision for the future, and I'll definitely be watching Braid and hopefully it'll be one of those companies that will be, you know, ipo-ing and hearing all those great things about it. But before you wrap up, can you let our listeners know how they can learn more about Braid and stay connected with you?

Speaker 2:

Yeah, absolutely so. Quinley O'Shea is my full name. I think I'm the only one on LinkedIn. Feel free to reach out to me. If you mentioned that you listen to the podcast, I'll accept you. I'm always down to chat with people and LinkedIn is probably like my most active form of social media right now and then. If you want to learn more about Braid, you can go to our website, trybraidio and Tola. I'll actually help you get set up and we can do kind of a promo code for anyone who's listening. The Trailblazers can get you 15% off up to your first year. Yeah, I would love to see some of your audience check out Braid.

Speaker 1:

So to our listeners, as she said, be sure to check out Braid, but, as you know, we are always keen to hear from you about the podcast. You know where to find us we are on Spotify, apple, youtube, wherever you listen to your podcast. So until then, this has been the Trailblazer Experience podcast, and stay innovative, stay connected and tell another woman about the podcast. Thank you so much, quinley. Thank you.