Giant Robots Smashing Into Other Giant Robots

529: How AI Transforms Small Business Operations

June 13th, 2024

Host Victoria Guido chats with Jaclyn Siu, the co-founder of Starcycle, an AI platform designed as a COO for small businesses. First, Jaclyn describes her entrepreneurial journey and what led her to Starcycle, detailing her earlier ventures, such as helping to scale a men's styling app and a software platform for authenticating high-end art.

Her ultimate goal is to make the tools and experiences typically reserved for startup founders accessible to small business owners, who comprise most of the global business ecosystem. She outlines how Starcycle supports crucial phases in a business’s lifecycle—start-up, sale, or shutdown—by automating operations and documentation, easing burdens on business owners.

Jaclyn also touches on the importance of personal connections and genuine curiosity in conducting user research and developing products that genuinely meet the needs of small businesses. She believes we can achieve this by being deeply rooted in empathy and strategically using technology like Starcycle.


VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. And with me today is Jaclyn Siu, Co-Founder of Starcycle, the AI COO for small businesses. Jaclyn, thank you for joining me.

JACLYN: Thank you for having me. It's so fun to be here.

VICTORIA: Great to be here with you as well. Before we get into learning more about Starcycle, can you tell me what's going on in your life outside of work that's exciting for you?

JACLYN: This is a very big departure from what I do on a day-to-day basis, but I am a huge coffee fanatic. And so, I love sampling all different kinds of coffee beans from around the world. And this morning, actually, I just finished the last cup from this amazing roastery in Osaka, Japan. They're called Mel Coffee; shout out to Mel Coffee. That's what I spend a lot of my time outside of work doing is trying different coffee beans.

VICTORIA: No, I love it. I love coffee as well. Actually, I am currently out of espresso beans. We have a fancy espresso machine maker. It's like our one big luxury in the house, and I don't have any coffee beans for it. So, I might need some recommendations from you [laughs] on what to get.

JACLYN: My sympathies on the lack of coffee, but I have plenty of recommendations. We can absolutely jam on this afterwards.

VICTORIA: Okay. Because you've traveled quite a bit, of all the places that you've been, where is the best cup of coffee that you've had?

JACLYN: I mean, I definitely have my favorites. In New York where I am currently, I would say that honor belongs to The Coffee Project. Actually, it's a tie between The Coffee Project and Say Coffee.

In Berlin, where I was based for the last seven years or so, I would say that honor goes to Bonanza Coffee. I used to go there every single day. And I attribute a lot of my success in Berlin to all the beautiful cups of coffee that they served me.

In other places, I would say what comes to mind is for sure Mel Coffee in Osaka, Japan, also, Glitch Coffee in Tokyo. In Hong Kong, that would be Craft Coffee. Hong Kong is where I'm from originally, so I have a very big fondness for any local roasteries. And I am going to stop there because, otherwise, this would become a coffee podcast, and I don't think this is what we're here for [laughs].

VICTORIA: I think there's a pretty strong coffee interest in our listeners, but they can tell me if I'm wrong. No, I think that's great, and it tells us a little bit about yourself. So, you've lived in all these different places and all these backgrounds. Maybe you can tell us a little bit about how your background led you to starting Starcycle.

JACLYN: Starcycle is my third company. I'm a three-time founder, advisor, investor, and mentor. I built my very first startup in my senior year of college, which was a men's personal styling app that surfaced shoppable outfits based on your calendar, style preferences, weather, and other things. And decided quite quickly early on, about a year in, that I wanted some real-world experience before understanding what it's like to run and build a company. I realized, hey, I need to know what it's like to be in one before I can build one.

So, I spent the next decade-plus in the creative culture and tech spaces, everything from sales and partnerships to marketing growth and operations. I worked on really exciting things from album releases for Rihanna to closing brand deals with TikTok. So, that led me to New York, to Berlin, and now back to New York, which has been really fun.

My second startup was co-founded over the height of the pandemic, and we built software for blue chip art galleries and working with them to authenticate blue chip and high-end physical art pieces. We authenticated $63 million worth of art in the company's lifetime.

The even tide of that, so towards the end of my second venture, that kind of initially planted the seed for Starcycle because we had been facing some more difficult times, and we were facing some pretty difficult decisions. I just had this Eureka moment, so to speak, where I was like, hey, I know firsthand how difficult it is to found a business. I want to use my knowledge to help at least one person get over the finish line. And I explored so many different permutations of that. I spoke to startup founders to small business owners, spent hundreds of hours exploring different ways that I could use tech to empower founders, and eventually ended up with Starcycle, which, as you mentioned earlier, is the AI COO for small businesses.

And what we do is we are supporting business owners at the mission-critical stages of their business life cycle, so the startup phase, the selling phase, which is when they're hoping to sell or get acquired, and also the shutdown phase. And so, we review and parse through key documentation and automate key operational tasks such as licensing, identifying engagement terms, drafting disclosure statements, et cetera, et cetera. So, it's very much born out of my own experience as the COO and also as an operator for many different kinds of businesses.

I grew up in a very entrepreneurial family of restauranteurs. My dad runs his own practice as a doctor. And I have cousins and other extended family members who are accountants and have their own practices. Somehow, half of my generation in my family are all startup founders now, so that has been really cool just being immersed in that, and also, yeah, wanting to use tech to give back, essentially.

VICTORIA: I love that connection with your family and how that mindset is a part of your culture and who you are. It's really interesting to hear and replay a little bit back of what you said about, you know, you knew you were entrepreneurial, but you wanted more experience. And then, you got to go through starting your own company several times. And now you're trying to share the experience you got from that with other founders.

JACLYN: Exactly. And what drew me to small businesses, really, was that startups do have quite a lot of help. Of course, we can argue perhaps a separate episode on how this support is distributed and whether or not it's equitable, but startups do tend to hog a lot of the headlines and a lot of the glamour and the glitz of being a founder.

And where I was really drawn to was the day-to-day coffee shop owners; for example, that was a big one, or just the fact that 99% of businesses around the world are considered small businesses. And I said there has to be a way to take a lot of the great tools and services that we have enjoyed as startup founders and kind of make that a lot more accessible to the people who really need it. And so, that was really the big bow on top for me to start working on Starcycle.

VICTORIA: Yeah. It's interesting to think about accessibility and inclusivity, and not just access to funding, but access to tools, access to knowledge, and support, and getting your business up and off the ground.

JACLYN: Exactly. I think the knowledge piece is a big one. And with knowledge, of course, comes support, as you say, and both of those things require a lot of hands-on education but also guidance. And one thing that I've learned over my career as an operator but also as a serial founder is how much that initial touch point really matters for folks.

And so, when I say that, I mean, just think about the very first time you encountered a new piece of technology and the feeling that inspired in you and how you felt like that new piece of tech, for better or for worse, reinforced, or not, that feeling. I've been really lucky to be at the forefront of helping a lot of people navigate these experiences, from helping fashion brands at the very beginning of my career, helping fashion brands understand social media.

This was before sponsored content was a thing. We still called them bloggers back in the day. Yeah, teaching them that social media is going to be an asset for brand marketing, and kind of being on the first wave of tech partnerships, and embracing social media as a platform, to working with artists to get them onboarded and comfortable with streaming. So, I was at Roc Nation at the time when streaming was really just starting to take off. It was the same year that Jay acquired Tidal. And so, there was a seismic shift in how the music industry as a whole was grappling with this new tech.

Fast forward to working with art galleries, probably one of the most difficult technical nuts to crack, so to speak, and working with traditionally folks who reject new technology and are wary of software that doesn't offer the same level of discretion or convenience that they are used to, and working to get them excited about software solutions that are built just for them.

And so, the through line, for me, you know, as I look back, is how can I take something scary, and intimidating, and difficult to understand for your person who is chronically offline, so to speak, and translate that into an experience that they look forward to that makes them see, "Oh, this is not just some sci-fi hubbub; it's not just what the Yahoo's at Silicon Valley are up to; this is going to help me and what I care about"? And that particular thought process, that particular intersection, is what really gets me going every day.

VICTORIA: That's really interesting. And it reminds me of friends that I have who have really deep domain expertise in certain things like nutrition, and coaching, and early childhood intervention and development. And they're asking me, someone who has, like, a connection to founders and startups, about, like, "How do I get my thing going? Like, how do I take this knowledge and build a business around it?" So, maybe you can tell me a little more about what research you're doing with these groups of people, with these small businesses. And what kind of questions are you asking, and what kind of things are you finding?

JACLYN: Sure. So, I started with a hypothesis, which was this slightly more nebulous notion that everyone will have an AI copilot. And so, I started to workshop what that could look like for a business owner, specifically because 78% of small businesses are owned and operated by one person. And my expertise or experience as a founder is having had a co-founding team where we can fill each other's gaps, and lift each other up, and work on different things. And a lot of small business owners don't have that luxury.

So, I said, okay, this is a problem that I have noticed. I am going to explore this to every single nook and cranny I can possibly find. And that led me to experiment with different ways to apply AI to this particular problem. I started looking at the early stage founding stage, where business owners are identifying their next steps to get their next big thing off the ground. They're navigating bureaucracy and figuring out what licenses they need what paperwork they need to file to make certain things a reality. And that, to me, felt like an easy place to start because it is a very well-documented and well-accounted-for space. So, we quickly shipped an early beta feature just to gauge market sentiment and to see what people were really looking for.

There really is no shortcut here, in my opinion. It's really about putting in the time and the effort to talk to everyone that is interested in finding a new solution for something that has deeply plagued them in some way or another. In a way, putting on different hats as a psychologist almost, like, understanding where their pain points are really stemming from. Is it, like, an operational thing? Is it an emotional thing? All the way to introducing them to something new, which involves reimagining what that user experience could look like, all the way to just being open and having a clear line of communication.

I talk to our users almost every day. We're on calls; we're on emails. And I just love hearing from them, and they know that they can come to me and talk to me about things. I've consulted for some of our small business owners before who come to me with different questions like, "Hey, can you help me with this business plan?"

Anyway, so, through all of those conversations, I started to stitch together a few things. The first being that AI is changing so rapidly, and, of course, this is something that is challenging but also incredibly exciting because no one really knows where it's going. We're all kind of testing out our hypotheses in real-time. We're all building towards that reality we want to see. So, noticing that a lot of co-pilot promises we were still, or at least I feel like, we're still a little bit far away from that. And so, I started examining, okay, what is AI already currently really good at and will only get better at? And how can that be applied to something that all business owners have to face?

And so, I expanded my search into other life stages of a business, and I identified that over hundreds of hours of conversations as the M&A stage and the closure stage. The M&A space is very exciting. It is also very well accounted for. And, currently, I'm spending quite a lot of time looking into the bankruptcy aspect, the end of life, something that, unfortunately, a lot of businesses will have to go through.

And yeah, really studying that space, deeply realizing that we can probably find a, if I may use this as a verb, a "turbo tax" for all of these different key operational moments for every small business, right? So, we can, quote, unquote, "turbo tax" starting a business. We can, quote, unquote, "turbo tax" trying to sell your business. We can turbo tax, closing down your life's work and trying to find a good place to put it to rest.

VICTORIA: How do you find people to be a part of the research? And how do you make sure that you're being inclusive or, you know, going after the right groups?

JACLYN: To the best of my ability. I start within my own networks. Luckily, since at this point, I have built quite a lot of friendships and relationships just within founders of all different kinds, I started by reaching out to different founders and just approached it with a lot of curiosity. I was like, "Hey, what are you working on? What is troubling you? How could I help?" And approaching it from a place of "How can I help?" as opposed to "How can you help me?" You being, of course, the founder I was speaking to. Yeah, really just being in the position of I want to learn from you, I would say, in hindsight, has been the key to a lot of folks being willing to speak with me.

And then, of course, on the call itself, when I do manage to get that scheduled, when I speak to them, and doing everything to make them feel heard, to make them feel welcomed. I show up to every single call prepared about this person. I have my questions prepared. Usually, within Calendly, for example, people should fill out what their profile kind of is. So, we do a lot of that pre-work and get that out of the way. And it also helps me prepare for the call. Weirdly enough, it's almost like preparing for a podcast interview.

And then, from those calls, I always ask like, "Hey, I really appreciate you spending time talking to me. Do you know one person who would be willing to do the same thing?" And I would say, nine times out of 10, the answer is "Yes." And then, I get a follow-up email being like, "I loved talking to you. Here's my friend who is also facing a similar thing. I already told them about our conversation. They would love to speak with you." And it just kind of flows from there.

And so, I guess to sum it all up, it really is being thoughtful with your relationships and letting that compounding effect work itself. And at this stage, like, as an early-stage founder, you and your...I don't like the word reputation, but I can't think of a better one right now. Your reputation is really what the currency is, and people typically want to help. And they also want to feel helpful, and they want you to show that they were helpful. And yeah, that has been something that I've seen a lot of success with personally, whether it's through user interviews or approaching it from, like, a sales and partnerships perspective.

VICTORIA: I agree. I think I found the same thing where, what you want to call it, and it's your reputation or your authenticity and your genuine interest in solving the problem that you're going after. I think a lot of people are, you know, of course, they want to talk about things that are bothering them, and they want to see other founders succeed, and it's part of a community. So, it's really nice to hear that's been working for you.

JACLYN: I'm so lucky that this particular thing is what really excites me about being a founder is: having that opportunity to have these conversations. Also, at this point, probably my superpower that I feel like I can draw from so many different experiences to be a good sounding board for whoever it is that I'm talking to.

And I remember this so clearly from my previous venture where we were building software for art galleries, and we had some of the most commercially successful artists and art galleries of modern times. And they went on record saying that, you know, they're switching their solutions, or they're coming on board for the first time. And they're not considering any other potential incumbents or competitors simply due to our ability or my ability to talk to them like equals, talk to them like people.

They were like, "We spoke to so many founders who were building different kinds of tech solutions for the art industry or the art world. And we always really felt kind of small talking to them because they were throwing a lot of jargon at us. They essentially wanted us to operate under a cloud of confusion so that, hopefully, we would just go along with whatever they say. And you were really the only one who would sit down, take the time to explain, take the time to hear us out, and kind of meet us where we are and see us people."

And I was really kind of taken aback by that. And I do think that advice applies generally, but especially when it comes to speaking to folks who identify so deeply with what they do, like small business owners, it is so key to really just treat them with respect. I mean, ultimately, that's really what it's about. Like, you respect that they know things that you don't, and you don't lord anything you know that they don't over them.

VICTORIA: I really appreciate that perspective. And I'm curious if maybe there are some core values from your educational background in journalism that flows through into your being a founder and how you have these conversations with people. Are there any core values that translate from that?

JACLYN: I love to listen. I'm just such a curious person. Yeah, I guess you could say that it is a journalistic approach to, you know, ask open questions and let the person feel like they are steering the conversation, and, you know, being that safe space that they know whatever it is they're saying is being taken seriously.

One of my personal philosophies when it comes to founding is that I let the problem tell me how it wants to be solved. I have a general direction, right? Like, my North Star is that I want to use tech to empower founders; in the same way, you could say that you might start writing a piece with the general idea of like, hey, this is what I want to write about. And I'm open to letting my subjects kind of steer where they really care about so that, like, I end up writing something that is compelling for everybody.

And so, yeah, I'm always open to finding the best way. This openness and curiosity, really, has led me to meet some really interesting people and dive through some very fascinating rabbit holes that I might not have done so otherwise.

VICTORIA: Oh, that's really cool. No, I like that a lot. That's super interesting.


Are your engineers spending too much time on DevOps and maintenance issues when you need them on new features?

We know maintaining your own servers can be costly and that it’s easy for spending creep to sneak in when your team isn’t looking.

By delegating server management, maintenance, and security to thoughtbot and our network of service partners, you can get 24x7 support from our team of experts, all for less than the cost of one in-house engineer.

Save time and money with our DevOps and Maintenance service. Find out more at:

VICTORIA: So, in these conversations, you're having in your early discovery process, were there any points where you decided to pivot your strategy based on what you learned?

JACLYN: I would say that the most interesting point was...I think this is probably, like, the clearest example of...whether it's a pivot, or, like, a redirection, whatever you want to call it. This was before I kind of arrived at the stage of bankruptcy or the idea of bankruptcy, which is where I'm really diving deep to at the moment. I had already spoken to a lot of founders in kind of the early stage of starting the business when I was talking to them about, like, "How can a tool like Starcycle help you on your journey?"

And a lot of them were like, the ultimate milestone was, of course, to sell the business, that they want that ROI, that they want to know that, you know, something that they've worked so hard on was going to end up in great hands. And so, I started examining that side of the spectrum. So, that was, I guess, refocusing number one, which was, okay, I want to understand the buy-sell space, kind of the M&A space, to hear what success factors led people there.

I spoke to everyone I could think of on that end of the spectrum, you know, people who had sold a business, people who tried to sell but didn't sell, people who acquired a business, people in private equity who are looking to buy and operate a business, you know, different buy and sell marketplaces, so on and so forth.

And this one conversation with the head of M&A at a language company it was a nice chat. And he kind of mentioned as a throwaway, "Oh, by the way, like, one thing we also look at are distressed assets." That was it. And I said, "Okay, let's unpack that a bit," and just kind of left the rest of my questions. And we started going in that direction. And then, I realized it's a different side of the same coin, exploring M&A and closure, because they are, unfortunately, very closely related to one another. They are both on the ends, like, end of the life cycle.

And so, that one comment which might not have occurred, you know, let's say if the person didn't feel like he had a safe space to kind of open up about his process, that has sent me on another journey to really, really dig deep into this very opaque and difficult area, where I'm actually, again, really, really excited to really unpack: How can we help people at the time of need, and how can we use tech to do a lot of the heavy lifting to free them up for very emotionally taxing tasks? Which, of course does happen at that end of the life cycle.

I still very much believe in the overall idea of using AI to help small business owners end to end, but really, I found this particular wedge because I guess I was open to that. And someone dropped the crumb, and I was like, "Let's take that path. Let's talk about it. "

VICTORIA: So, it had a high emotional element there, and there's a lot of tasks associated with it that would make it a good use case for AI to support that particular phase of the life cycle?

JACLYN: Yeah, that's absolutely my hypothesis right now. I've been validating this with different small business owners who have, unfortunately, had to close their business. I'm also talking to bankruptcy attorneys. And so, yeah, I guess we'll see what that process looks like. By the time this episode is up and running, I might have found the right angle to tackle this problem, or I might have just found some other opening to look at. So, I guess it really is up for grabs at the moment, which is a very exciting part of being at the early stage, but, of course, also slightly terrifying [laughs].

VICTORIA: Well, we'll have to have you back on in a year to check in and see how things have progressed. But it makes sense to me. And in all of my recent experience just hearing from founders around San Diego, it sounds like if you're going to be a founder, you are going to have to shut down a business at least once [laughs]. Like, usually, you found multiple businesses and that means that you do have to close or, you know, go through this final action at least one time. You will be very lonely being a founder, and I can see having support through that time and having it be easy could be really helpful and make it seem, you know, easy and maybe even just, like, make it easier to start things up again, too.

JACLYN: For sure. And I love that you touched on the starting again because founders, typically, more often than not, have this very stubborn optimism that we're like, we're going to figure it out one day, and we're going to do it. And at the risk of sounding a bit hokey, bankruptcy can be a beautiful thing. It is, of course, incredibly emotionally difficult.

But what I find really incredible is the notion of bankruptcy was really born out of this idea of we recognize that you took a huge risk. And even though the risk didn't pan out in the way that we all hoped that it would, we don't want to penalize you further for having taken that risk. So, here is some protection so that when you are ready again, you can start again. And I just find that sentiment very, very powerful. And I've certainly seen that to be true in my own experience.

So, this really is, like, I feel like my heart and soul problem, you know what I mean? Again, of course, I'm back to my core value I mentioned earlier. I'm open to letting the problem tell me how it wants to be solved. And so, I'm going through that process again to find, okay, what is it in this journey that I can solve with AI? And so, yeah, we can check back in however long, maybe six months, a year or so, and then see where. I would love for you to hold me to that.

VICTORIA: Absolutely. I will. I'd love that. Yeah. And, well, on that note, then, what are the biggest challenges you see on the horizon in the next six months?

JACLYN: I would say the biggest challenge that's coming on the horizon really is, to me, what is very exciting. I alluded to this earlier, but it really is this notion that, of course, we all recognize that AI is disrupting. It has already disrupted a lot of what we know to be true. We're all just testing out our hypotheses in real-time. No one really knows in what direction this wind is blowing. I don't think people could even agree on what AGI means, right? Like, AGI, is it, like, a very, very general thing, or is it AGI for X, AGI for Y? Like, what does that look like? And I don't think there's, like, a consensus on what this looks like, right?

So, in a way, every founder building in this space, including myself, we're all just working towards what we think that reality is and what reality it is that we want to see. It's a huge challenge because we're quite literally building what has never really existed before. And it is a feeling that I'm personally, luckily, very familiar with, I get super energized by. We're in the beginning. Everyone says this, right? "We're so early," but we really, really are so early in this new wave. And I'm really looking forward to drawing on all of my experiences being at the forefront of various other big changes and applying them to this very particular change.

And then, of course, I'm also a little bit nervous about this. I think anyone would be nervous knowing that the tide could change at any moment. I'm also not delusional about this per se, but I'm definitely optimistic. I think we're going to see a lot of generational companies built at every single possible intersection of AI and something. So, it's like AI for small businesses, right? Or you could even go even more granular. There's going to be an AI for hair salons. There's going to be AI for coffee roasters. There's going to be just so many ways to capture this new energy and this revolution that I am very intimidated, but I'm really excited about this.

VICTORIA: So, the gravity and the size and scope of the change, and that being unknown, and also what you mentioned on the tech stack, having that variability and just knowing you might have to pivot or change very quickly, is an exciting challenge as well.

JACLYN: It is. It definitely is. And, of course, it's a tough one to solve for sure. Any founder who wants to build something, really now is the time to just give it a shot because there are so many intersections up for grabs, and that doesn't come around very often.

VICTORIA: That's really great. And I love your approach to that by just trying to see how can you use your expertise and follow the problem and see what solution comes up that is worth focusing on? So, I really appreciate you sharing that. I'm curious if you know what success looks like six months from now or even five years from now for Starcycle.

JACLYN: I would say in six months, I would envision, at this stage, having maybe a small suite, but a suite nonetheless, of different aspects of the small business life cycle, the mission-critical stages I spoke about, having the, quote, unquote, "different turbo taxable features" live. And so, we're already able to start really moving the needle for these folks. We have our first test feature live in beta. We're already helping close to 1,200 business owners. So, I'm really looking forward to just increasing that number.

In five years, I would really love for us to be at that stage where we are helping small business owners end to end. And so, I do see AI growing at a rate or the capabilities of AI growing at a rate way faster than any of us can imagine.

So, I'm going to just throw this out there and say, in five years, I would love for Starcycle to be, like, a true AI COO on every single step of the way, like, a real strategic thought partner, executional partner for your small business that you otherwise wouldn't have. And you're in the trenches with your AI COO, and we're going to help you build the best business you possibly can. And we'll take care of your end to end. And that, I would say, is my ultimate grand vision. So, I guess let's check back and see what happens.

VICTORIA: I like that. And, you know, that's a really awesome future vision to build towards. And in the immediate term, I'm curious to ask you more about Starcycle and how AI and people work together to give leaders confidence that the COO is giving them good answers and all that.

JACLYN: One thing that we noticed while we were developing our beta and continuing to improve on our current offering is coming to the realization that we want to focus on what AI is currently already really good at and will only get better over time and, to us, that was data parsing, data optimization, formatting, data extraction. And so, that's where the next immediate stage of product development is going to go is really leaning into this data extraction aspect.

And we feel like this true thought partner; strategic partner thing will happen over time once we have, like, a lot bigger pool of data of your business to work with, where we can connect dots that you might not have otherwise been able to connect, whether it's because you physically do not have the time, or you may not have the knowledge to, let's say, comb through your monthly P&Ls to draw out certain trends in the way that AI can really do for you.

So, we're acknowledging the current limitations of AI while maintaining optimism on kind of the long run of what we think AI is going to do. And so, I think for the small business owners that we're currently supporting, we are very much on deck as humans to help them with some of the more strategic moments. And our users know that they can find us anytime. And for a lot of the more data operational action item-driven tasks that they need help with, then AI can step in fairly comfortably and help them in the majority of the cases.

VICTORIA: That sounds really cool. I like how you broke that up. Do you have anything else you'd like to promote?

JACLYN: I'm open to so many different kinds of conversations. And every single conversation is helpful. So, please reach out or sign up, try the product.

We look at every single survey. I respond to every single survey personally with follow-up questions if you'll allow them. So, I really just want to help anyone who's listening. Whatever problem it is that you're dealing with on your founding journey, I'm here to help. So, in whatever way that I can help you, please let me know. I would love to hear from you.

VICTORIA: I read in your background that also includes asking you questions about your time working with Rihanna. Is that right? You're open?

JACLYN: [laughs] Correct. I suppose. Yes. If that is of interest, we can certainly talk about it [laughs].

VICTORIA: Oh, that's great. No, I love that, the detail on that. And then, also, we didn't get to talk everything else about your background. You also have that you're an angel investor, and you also are just a general incredible mentor and coach. So, I don't know if there's anything else you wanted to share about that.

JACLYN: I think part of it is also really driven by my passion to empower folks with technology. And a lot of that component, as we've alluded to multiple times over this podcast, is the educational component. And I think I've been really lucky to be exposed to a lot of new things throughout my life. And I want to play even some small part in helping other people encounter tech in what they perceive to be a safe and gentle way. And so, that's what I'm really excited about.

I do occasionally write small checks to companies and founders that I believe in. I spend time guest lecturing at colleges and also mentoring young girls and young women. And, generally, I'm an open book if you want to ask me about how I taught myself stop motion video editing to do something for Rihanna, all the way to how on earth did you find it in yourself to do a third company. I just want to help anyone and everyone who wants to make that difference in the world to be that difference that they're looking for.

VICTORIA: Yeah, you know what always gets me excited about tech? Is when people use tech to solve simple problems that helps everyday people. You know, I'm from Washington D.C. I spend time on the side from doing consulting with big federal agencies. I was helping startup nonprofits that were working to end homelessness and solve communication problems with nonprofit organizations sharing their services to people who needed them and that type of tech.

And I've been in California now for three years, and I've started rebuilding my networking here. And I'm starting to find those people who are working on those kinds of projects. So, I'm really excited to build a little community here in San Diego and to start giving back to some of those groups again.

JACLYN: Yeah, that's really, really awesome. And that really is what keeps drawing me back to founding is knowing that whether it's founding a non-profit initiative, or a startup, or opening up a coffee shop, like, I keep coming to coffee shops because, of course, I have a deep appreciation for them. But, ultimately, it really is such a tangible way to provide and to give back. And I can't quit.

VICTORIA: I mean, I could quit. I could quit and just, like, rock climb and be bad at surfing for the rest of my life, but I won't. But yes, thank you so much for taking the time to be with us here today, Jaclyn.

You can subscribe to the show and find notes along with a complete transcript for this episode at If you have questions or comments, email us at And you can find me on thoughtbotsocial@vguido.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore.

Thanks for listening. See you next time.


Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us.

More info on our website at: Or you can email us at: with any questions.

Support Giant Robots Smashing Into Other Giant Robots