Building AI Boston

Powered by Community with Stephanie Roulic

29 min
Jul 28, 20259 months ago
Listen to Episode
Summary

Stephanie Roulic, founder and CEO of Startup Boston, discusses how she built a community-driven ecosystem connecting New England entrepreneurs since 2016. The episode explores why now is an ideal time to launch startups, particularly for non-technical founders leveraging AI tools, and highlights Startup Boston Week as the region's largest startup conference featuring 100 sessions across all founder stages.

Insights
  • AI democratizes entrepreneurship by enabling non-technical founders to build scalable products without coding skills, shifting from founder scarcity to idea scarcity
  • Community-driven ecosystems thrive when leaders model the behavior they expect, practice radical transparency with competitors, and make participation accessible and free
  • Mental toughness and self-awareness about personal strengths/weaknesses are more critical to startup success than technical skills or capital
  • Regional startup hubs benefit from deliberate aggregation of resources (event calendars, directories) and cross-industry collaboration rather than gatekeeping
  • Volunteer engagement and community pride stem from making participants feel like co-creators solving problems, not just task executors
Trends
No-code and low-code tools enabling solo founders to build beyond MVP stage within 2-3 yearsShift from proprietary/competitive startup culture toward open-sharing ecosystems that strengthen entire marketsRegional startup communities becoming more inclusive and accessible through free events and aggregated resourcesNon-technical founders increasingly viable as AI handles technical execution, shifting founder bottleneck from coding to business acumenUniversities (e.g., Suffolk University) positioning as startup hubs and community infrastructure partnersFounder matching and co-founder discovery becoming formalized through dedicated programming (7+ years of co-founder matching events)Mental health and founder wellness emerging as critical success factors alongside business metricsAI-driven content creation and marketing enabling bootstrapped founders to compete with well-funded teams
Topics
Startup ecosystem building and community developmentNon-technical founder enablement through AI and no-code toolsCo-founder matching and founder discoveryStartup funding stages (pre-seed, seed, Series A)Founder mental health and resilienceRegional startup conference strategy and programmingFree and accessible startup educationVolunteer engagement and community leadershipCompetitive collaboration in startup ecosystemsFounder skill assessment and gap identificationBoston startup market positioning and reputationEvent aggregation and resource discovery platformsStartup operator and investor educationMVP to scalable product developmentInclusive startup community design
Companies
Startup Boston
Community organization founded by Stephanie Roulic in 2017 to connect New England entrepreneurs through free events, ...
Suffolk University Law School
Host venue for Startup Boston Week for third consecutive year; emerging hub for startup events and community partners...
Loveable
No-code platform mentioned as example of tools enabling non-technical founders to build products without coding skills
People
Stephanie Roulic
Founder and CEO of Startup Boston; first-time founder at 24 who identified gap in Boston startup community resources ...
Cara
Accidental entrepreneur and early participant in Startup Boston; volunteer and community advocate who speaks on panel...
Karen Kelly
Founder of Help Purposely Social and Launched by Lunch; speaker at Startup Boston Week focused on no-code/low-code to...
Quotes
"I had absolutely no idea of where to go to even figure out how to build a startup company. I was buying those books like, you know, the art of the print dummies and like sales department."
Stephanie RoulicEarly in episode
"If you're paying attention to anything at all, you are going to come across Stephanie very quickly. Like if you're paying attention to anything at all, you are going to come across Stephanie very quickly."
CaraMid-episode
"There is so much power in a solo founder's hands now because of AI. I am not the technical founder persona when building a tech startup."
Stephanie RoulicMid-episode
"99% of good ideas are locked up in people who can't code. And so it was just the idea of, you know, that this kind of vibe coding or AI or the ability to like get those ideas out of your head and into a working product is just so transformational."
HostMid-episode
"I truly cannot remember a time in my life in the past decade that I've had both days off on a weekend. You just have to kind of figure out what type of founder you want to be and also what your goals are."
Stephanie RoulicLate in episode
Full Transcript
At the heart of an industrial revolution is an innovation that changes everything. Building AI Boston sees artificial intelligence as a renaissance. From the heart of innovation and the mecca of tech learning, we bring you AI for real people to a conversation for everyone. Stephanie Rulick is dedicated to strengthening and connecting the New England startup community. As the founder and CEO of startup Boston, she helps founders, startup operators, and startup curious individuals find the resources, opportunities, and connections they need to succeed. Start up Boston hosts events and creates content designed to educate, support, and celebrate the region's startup ecosystem. And today we're going to dive into why it's a great time to be an entrepreneur in this mix. Welcome to the show, Stephanie. Thanks for having me. I'm so excited to be here. Oh my gosh, we could not get over it. I want to tell you flat out like my one of my favorite things is startup startups are my heart and soul. And I want to just really get into this right away and ask you in the beginning, right? You had what $300 in your pocket and a great idea. And you're in this rigigo system. There's no doubt it's a great place to be. But can you give us a little bit of the origins of why what did you see that was missing? Yeah, for sure. I mean, really from this end of things back in 2016, the summer 2016, I had co-founded a MarTech company and I was a first time founder. I was not even 25 yet. I was still 24 at that time. And I mean, as a 24 year old founder in Boston, at that time, I had absolutely no idea of where to go to even figure out how to build a startup company. I was buying those books like, you know, the art of the print dummies and like sales department. Literally those books. So I was like, what do I even do? I have no idea what I'm doing, but I just want to build this startup. I was just excited. I was excited about building something from scratch. So really kind of like the urgency for me to create something, such as startup Austin was really being in that position as a first time founder. And being like, I don't know where anyone is in Boston that's also in the startup community. I don't know how to start a company. I don't even know where I'm supposed to begin. And also I keep painting people online, didn't they ignore me? And my request was, I was right out, right? So that was really kind of why startup Austin was first created in 2017. Well, thanks for sharing the pain point because I think that a lot of people will relate to maybe even scratching their head and asking, why would I even try to put myself out there? But I want to know, you know, you two know each other. You're a product of that rich ecosystem. So why don't you just talk about how you two met? Carried chicken was worse, Stephanie. Yeah. So I'm having a problem. I love it. So when I started, I was an accidental entrepreneur myself. And, you know, one of the very first people that I came across, is when you start to enter that ecosystem here, you cannot help but meet Stephanie very quickly. Like if you're paying attention to anything at all, you are going to come across Stephanie. And she's going to welcome you right into the community, which is pretty amazing. And so this was early on in our journey. And I actually got an invitation from her. And I don't remember if she pinged me or I pinged her or whatever, but it all worked out. And so I was able to do one of my very first actual panel discussion that I ever did about our company at startup Austin. And it was so great. And I remember just being very, very appreciative of her because I think the origin story is exactly right. Like she's been there. She's done that. She knows how hard it is. So she's here to like help other people along their journey. Well, that's one of the really fascinating things. And I think in an age of AI, what's most impressive car appointed this out to me, because you two know each other. But she said that you have a certain knack for getting that volunteer spirit ignited. And I want to give my hats off to you. This is the huge dilemma in this day and age where people are literally freaking out that an algorithm could solve all the problems out in the world. What do we need humans for? You figured out how to ignite human behavior. Why are you so good at that? Do you have a guess? No, I'm sorry. I don't mean to put you in the place of a shameless plug. Or either one of you chime in about what that ecosystem does best, which I see is like just picking up the shovel. Why does that happen for you? I mean, I would say that for me personally, the leaders that I admire the most are the leaders that are willing to go and pick up the shovel with the other folks that they're working alongside with. I'm a huge believer in leading by example and also not asking anyone on your team to do something that you would not do. I think that as a leader, you have to, you know, be about five steps ahead of schedule in terms of what needs to be done. You have to have a solid plan. You need to be able to you take that big plan and distill it into bite size information so that you can really accomplish great things together as a team. And honestly, it just comes back to that leading by example and being excited about what you're leading everyone towards. So I think perhaps me, you know, trying to lead by that example, I've seen others do may have played a role in other folks also being passionate about wanting to give that the startup ecosystem and play a role in building up star Boston as well. But you would definitely have to ask one of them because I don't want to speak for them either, but that's my hypothesis and I think and I know for me personally that that is how I lead. You know, I've got some theories to you, Cara, I'll let you answer the question to you. Yeah, makes her so successful in getting people galvanized. Yeah, because I am one of them and I have to say, you know, it's cool whenever you go to her events because the people who wear the startup Boston shirts. I know walk around and it's kind of same color as this, right? The one which I did not do on purpose. But you see these people walking around the events and they have this sense of kind of pride, like you can tell that they feel really good that they're in this role and they're being associated with this with this group. And again, these are volunteers and I think, you know, I think what it has to do with this part of what makes the Boston ecosystem so special to like we have a little bit of once an underdog kind of thing, but a little bit of like, hey, you know, we're special too and we have our own special way of doing things and I think there's like just a huge commitment here to like, letting the world know how special Boston is and the ecosystem and obviously the real reason Stephanie is so good at is because she knows a lot about marketing and communications and our own personal relationships because we know everything about everything right Stephanie, but you just have this way of igniting. But I think it's because the people feel like they're part of it, they're part of the solution that you're bringing in not just you know being asked to move tables around, but that's just my observation. I mean, they are part of it like I will just chime in quickly like they are definitely part of it. I mean, I do believe that it does take a whole community to really create that community that you want to see and for folks to want to constantly contribute and give back whether that's speaking out event or you know, being with me at the end of the event and picking up trash and be like, okay, let's go and make sure that we found it like all of those jobs like they have to get done and they're all equally important in terms of, you know, respecting each other. And also really building a start of ecosystem here. So I mean, all of them are playing a huge role in terms of really creating what the start of seeing here is in Boston. So I'm in a wager a guest because I don't have the pleasure yet. We're going to talk about the what comes next next, but I will win wager a guest based on how you scouted Kara that your mad skill is in valuing people and valuing people will always ignite their heart. So that's just my nickel at chime in on it, but I want to talk a little bit about what so yeah, we're all we're filling the love and we're showing the hearts right now. And then we're in the this we're at a real intersection and I'm happy that you know your season at you know you started at 24 and now you're a seasoned veteran, but I want to talk about it. You've seen a lot of inventions come and go a lot of disruptions. I think the hardest part about AI if we're going to speak honestly is that it sort of feels like it's devaluing that human element. So knowing that it's a scary time, I want you to make a little pitched not speaking for AI or any other thing that you don't want to speak on, but why do you think now is actually a great time to be an entrepreneur. What's the upside of the environment right now. I mean, there is so much power in a solar pranumer's hands now because of AI. I am not the technical founder persona when building a tech startup. I am more of the leds do sales, let's share the concept of what that start is, let's go and you know deliver value to the customers, let's create the business plan, let's figure out where we're going to be in 10 years from now, like that's more of the hat that I play in the start world. But if you ask me to code, just don't please do never. It will I won't even know where to start. I'll just look at you and be like, I got nothing like what program J.E.V.E. is like I can't see that. But that's really important to say it because if everybody can just everybody listening right now, if you can just really understand what, let's break down what you said. It's a great time for solar pranours because there are more tools possible. What's so great about what you're doing to democratize the scene is that the things that really matter are for free. For most of your events are free. Is that right? That is correct. They are all currently free. We just really want to make it easy to enter the start of ecosystem. We want to make becoming an entrepreneur or a startup operator or an investor in the making like a very accessible avenue, an accessible career path for throughout New England. For us, that part is very, very important to us. But yeah, to go back to your initial question, I mean, I do think AI really gives those folks across those three personas, right? Like the founder, the operator and the investor in the making it really gives people the ability to kind of fulfill their dreams and to really, you know, you still have to work very hard. You'll still have to learn new tools, but I think because of AI, it really kind of puts your career path and your career goals more in your grasp. If you take the time to, you know, double down and learn what's available to you now. And just in developing prompts that make sense to learn the things what you don't know. But, but really coming to your events and learning, you know, the lingo of the startup culture, that's really important. I mean, have you ever heard of the book one minute manager that talks about why one person can't be all three of those things you just said, the operations person, the marketing person. I think we're leveling that playing field a little bit, right? But anyway, yeah. So we definitely are it becomes it's becoming. I don't want to use the word easier because start up like this anything but easy, but it, but it definitely becomes more, I guess, achievable for one person to really scale up an entire business. And then I think we're going to have a chat or on social about how in a couple years from now there, you know, has the potential to have a unicorn company that's really just owned and operated by one single person. And I don't think we're there yet, but I do find it fascinating with where we're going and how that could become achievable where you don't even have to have that coding background in order to make that happen. And I don't think that's going to happen in 2025 personally. I still think some of those, you know, vibe coding, no code tools, all of that will still, it still needs a little bit more work in order to make a scalable product and not just the MVP, but it's, it's exciting how that is a potential new world out there in a few years for for non coding founders that want to create their own, their own company. Yeah, I love that. And yesterday Karen Kelly, who is another friend of ours, who was on the show and she's a speaker coming up at startup awesome. I admire what she's doing. I launched by lunch. I love it. She's amazing. So she, she, she, she was on an episode a little while ago. And so she's like my name, I'm pretty much, she wears multiple hats. So she has a company help purposely social and she has launched by lunch, which is all about vibe coding. And she reposted something on LinkedIn. So this is all again, like the community. We all, you know, hear what each other's doing, but she reposted something yesterday on LinkedIn from I think it was loveable where they were saying that 99% of good ideas are locked up in people who can't code. And so it was just the idea of, you know, that this kind of vibe coding or AI or the ability to like get those ideas out of your head and into a working product is just so transformational. And I don't just really struck me that like, yeah, just think of all those good ideas that would just die on the vine because someone doesn't have access to the capital or the right kind of programming programming. Now they can just build it. Maybe not scalable yet, Stephanie, but. Yeah, no, it's very exciting. Start Boston's been hosting a co founder matching series since 2018. And in that co founder matching series, I'm going to post it, I don't know, dozens upon dozens of events, right? It's been happening for about seven years now. But it's it's been intriguing because there's a lot of great ideas that non technical founders have when they arrive at that event and they're looking for someone with more of that coding background to bring that company to reality. And I mean, to your point, I'm excited about, you know, how in a couple of years that that technology might be at a place where it can get beyond that MVP, you know, initial product. So I'm very excited for this future generation of entrepreneurs. Okay, so I'm going to say I don't even live in Boston, but when I saw Karen Kelly's post, I went, I got to be at startup Boston week. So let's just talk about it. Why are we so excited about it? Go ahead and tell us what we're going to see there, what people can expect. And let's highlight again. This is a free event like, oh my gosh, if you want to feel good about asking dumb questions or feel good about having an idea and just bumping elbows with these women and gentlemen. Talk about what they can expect at your Boston startup Boston week. Yeah, definitely. So start a Boston week. It is the largest startup conference in New England. We do a really wonderful job at highlighting only New England speakers at our event as well. So we do a very good job at really highlighting folks from New Hampshire, Maine, Rhode Island, and of course Massachusetts and also Vermont. Let's not forget Vermont in that statement in terms of what they're building here in the startup community. We really want to make this more of a community driven event where we're highlighting what is what is incredible about our local startup ecosystem and really amplifying that and celebrating that right. At the week itself, there are about a hundred sessions. They consist of about panels, workshops, of course, networking events. And those 100 sessions are really created for everyone. Everyone from an idea stage to traction stage to scale stage. We bring in folks from series A and before. And there's content for founders, operators, and again, investors in the making. So for people who are interested in what is the startup community here in Boston all about. Is startup life for me, but also for folks that are currently already working on a company, having MVP, perhaps already landed their seed round of funding. There's content for all of those stages. And we get into very, very nitty gritty topics and workshops. This is not a fluff, you know, a fluff conference. This is a please bring your notebook or laptop, whatever, whatever works for you. Take notes and come with all of your questions because people will come armed with all of the questions they have in order to start or scale a company. And that's what makes it so exciting and that's, you know, really why I create the conference to begin with is because I wanted everyone to get this questions answered. So I'm very excited. I could literally talk about this conference for days, but I will, you know, I will pause. I'll let the other two wonderful ladies. Okay, go ahead, Carl. Why are you excited? Okay, so this is like so from my own perspective. So forgive me. One of the reasons why I love this conference is because it's at Suffolk University Law School. And yeah, and just out of the randomness that is Boston, like we think we're this gigantic city and this, you know, it's, it's a small city. Everybody knows each other. So back in the day, I actually used to work at Suffolk at Suffolk University Law School. And they're just suffocates just a great school right in the heart of the city and very, I would say, like, I don't know very, I'm what would you say, Stephanie, like they're just there. They're showing up. They're just showing up for stuff and just definitely throwing up. They want to play a huge role in helping, you know, build and connect the startup ecosystem. And they are fulfilling that role as well. They, of course, host our boss make the start third year hosting at Suffolk University. They are incredible partners, but they're hosting more and more startup events as well that are accessible to the public. So I have nothing but nice things to say about that. You have nothing but nice things. They are just an incredible resource for the community. They and they are really becoming a hub for some startup events that are really spinning up in the city. This is what's great. And you guys have your local, you know, digs, but I honestly love the intersection of history and then, of course, AI. And I feel like, no, where else do I feel that sense of why history is important, why those institutions are important. Why the individual neighborhoods are important or the, you know, the feel of a particular community. So I want to, I want to give some love to to the fact that it seems antithetical to say, oh, we're so open because it feels like it typically businesses so closed and that there's all this sort of tight fisted, you know, I've got to be proprietary. And I think we're moving into an age of sharing. And so you've done this so successfully years on years on years. I think you're leading us into a generation that AI naturally just dissolves the boundaries, if you will, of, okay, I've got to keep it a secret to an open and sharing environment. Did you foresee that? Is that something that you, that's important to you or is it just a nice happy surprise? I would say it's definitely more of a nice happy surprise. I'm not going to go and pretend to be something I'm not. I will say that the way I've always tackled start a Boston week or any event start a Boston does is that I do want to create an open sharing environment. I really create those rooms where there aren't barriers to entry people want to share what they're working on what they're struggling with. I want folks to, you know, honestly have those open conversations. Even if you're talking with your competitor, there's nothing but good things that can become of those conversations that makes both you and your competitor stronger, which is good for the market. And honestly, really good for both of your companies because then there's a larger like customer base, right? But it turns their first seeing AI, I am, I, that was not, yeah, that's not my, that was not intentional. But I love it. And I'm happy about it. Okay. Yeah, you're, because you're an navigator, you're a person that's an navigator and that's a super valuable skill. So you're, you're mirroring what I want everybody to understand listening to this conversation that you're very human superpowers matter in this moment. No one can predict where AI is going to take us. Yeah, right. No, I definitely agree. And I mean, for start of Boston, what I'll do is I do pay attention to what's happening around us, even if I can't see whatever trend is happening in the future. I do pay attention to what the needs are of our own community, what the founders, what the operators need within our own backyard and really create either those opportunities for folks that have trouble connecting. I want to make sure they have ease of connecting or also just gaps and content, you know, that maybe we just don't have available in our own start ecosystem will start creating content that helps fill those educational gaps, right, until someone else that torch. And I do think that that that can translate to a lot of different companies as well to your point, right, is just kind of you know, read the room of, you know, what's happening in your own industry and being that voice that can help educate your own customer base and really making you that that beacon of light where they can go and connect with one another. Yeah, everybody talks about connection, but you are an OG connector like literally you've been here doing this now since 2016 very long, I know it makes me it's weird to think about. OG your OG and it's like you know, in a funny part about it is like Boston like i'm not originally from Boston. I'm been here 20 years or whatever, but it's it's like when people think about Boston they probably don't think oh, oh, welcome inclusive like it's maybe not like our reputation that we're a little more like you know. I don't know East coast and whatever not as friendly, but so what do you think Stephanie like what is it about Boston maybe that makes this sharing happen maybe differently here or like our what do you want people to know that maybe they think Boston isn't like that, so what would you tell people that aren't sure about like are you really open and welcoming in Boston are you sure. I think you definitely need to take some time to find your group of folks i'm not going to say that every single group is open and welcoming, but I do think that we've come a long way since I first started Boston you know if we go back to 2016 2017 apologies when I first started started Boston. It was not that welcoming of a space it was very difficult to find events in my personal opinion to attend they were all hidden you had to know someone who knew someone in order to figure out where to go it became like this whole like little game of like how how do I get on in the in crowd right put on hold. Yeah yeah and I will say with that stated Boston still has more work to do but has changed over the past you know nine years is that there are more ecosystem leaders from different backgrounds really placing or creating opportunities for folks to connect and really creating creating the Boston start the ecosystem that they want to see. And I think the more and more folks that really you know create events for different industries for different personas, the more that you know share kind of what they're learning along their own start of journey. You can never have enough of that in terms of founders and operators sharing and I think more and more people doing that in Boston which has started happening over the past nine years can only just make our ecosystem better. So I will say it is a little bit easier to figure out where to go now in the Boston start of ecosystem I mean start Boston itself we have an event calendar where we aggregate like I don't know about 70 different calendars into one view so that is your one stop shop to figure out where to go based on your industry and you know what you're doing and we also have a directory as well on our website so you can really easily filter by networking groups that you might want to go check out. So I think that's a great way to start seeing and start to find your people that you can go learn from. Wow well thank you for highlighting a little bit of like what needs to be what what the work is without throwing anybody under the bus here you're very diplomatic I love that. Knees work that means you know people out there listening to this show up. What do you think what do you think it takes to just succeed in business and what does it take to stay the course because you've obviously done that and I think this will speak to you know what is the human side of. You know lasting in this in this new environment. You have to have some mental toughness I would say it definitely is a lot of mental toughness and that mental toughness comes from of course the folks that you surround yourself with really find those people either at those networking groups events through star Boston week. So I think that's a great way to do that is to make sure that you know you can go and build relationships with and really mind share with as you build your company. But it also is a lot of different self work like self work in terms of you know really drilling into figuring out what makes you tick what you need to bring your best self to work to build your company. You know building a startup like it's a grind I mean I can't remember the last time in the past you know 10 years they've ever had both days off on a weekend. And I'm it's just been a moment like I truly cannot remember a time in my life in the past decade that that has happened. I'm not saying that that's going to be a good fit for everyone by any means. You just have to kind of figure out you know what type of founder you want to be and also what your goals are. And you know match up your lifestyle to where you want to take your startup and I think that that understanding of you know what fulfillment is and what success is to you. Well really trickle down in terms of like your whole lifestyle and what you need to accomplish that does that make sense. Oh yeah did you coin that phrase self work I'm going to start saying that all the time you know that's okay so for anybody listening again the not take away from that statement is yeah it's not easy and there is no get rich quick but the self work is so lightened when you come together with like minded people. I think the weight of of saying even the words I want to be a startup I want to have my idea come to fruition is just understanding you don't know what you don't know I think that's crushing for most people so we're going to eliminate that right now say show up at startup Boston week. And eliminate that part of the self work because you're handing out all these tools and you're and and I think there's nothing more powerful than standing shoulder to shoulder. Yeah with people that are in it like that you know that have the stories of survival. And I definitely want to double down a bit you said to you in terms of just understanding you know what you're strong at and what your weaknesses are as a founder I think you know once you understand okay I excel at this skill. Not so much at that skill it really helps you take your start to the next level right because then you also know what types of mentors you need to seek out you know what types of folks you should be purchasing so you can go read up on it and learn it. I was terrible at marketing I which I find ironic because now star Boston has become a marketing engine for you know a lot of what's happening throughout the start of scene but I googled so much. And that's really weird to cut if you're out like now how do you post on my tip like what what is this like how do people engage with one another like how do you set up your website and that's constantly changing right it's not a one deal by any means. But I think you know definitely by identifying and honestly like just take a minute right a list right down right I'm really good at XYZ and I need to you know improve one two and three. That will be immensely helpful to you and then at some point once you get more funding or revenue revenues always a good thing then you can go and hire someone to fill those gaps of what you don't know. Any final words ladies this has been fun this has been so fun ladies any final words on what's what's next and what you're excited about. I've absolutely enjoyed this conversation I'm excited to see everyone in September at star Boston week and also folks are just looking to learn more about the star Boston community. You can just type and start Boston out pop up on page one dive into our website with all the resources. I absolutely love the Boston start of scene I got to meet amazing incredible folks like these two ladies as a result so I hope to meet more incredible folks soon. Thank you for joining us on building AI Boston stay tuned for more enlightening episodes that put you at the forefront of the conversations shaping our future.