5 December, 2023

PowerUp Podcast | Episode 3 – Steph Roulic, Startup Boston

Steph Roulic of Startup Boston on her own journey!

Special Guest: Steph Roulic

In this episode, we had the incredible opportunity to connect with Stephanie Roulic, the visionary founder of Startup Boston and a force in her own right in the Boston Startup community. Following our own talk at Startup Boston Week and witnessing the vibrant community they’ve cultivated, we just had to bring Stephanie onto the podcast.

Join us as we dive in Startup Boston’s roots, the value of hybrid events, the significance of community research in your startup adventure, and so much more!

Find Steph and everything they’re up to at startupbos.org & linkedin.com/in/stephroulic. Also, for the latest in Boston events, check out their Community Events calendar here!


Adam: What’s up, everyone. Welcome to another episode of Power Up Boston, brought to you by Tech Superpowers, where we connect with folks from the Boston startup and tech community to discuss the scale-up journey. My name is Adam Fisk, and we are joined today by Michael Oh and Stephanie Roulic. All right. So we have had the pleasure of working with Stephanie and her organization now for a couple of months, and I think this came about from a very nefarious way of TSP wanting to sponsor and work with the local Boston community. But Stephanie, why don’t you give us a little picture of Startup Boston?

[00:00:52] Stephanie: Yeah. So, I am the founder of Startup Boston. Essentially StartUp Boston is on a mission to connect, educate, and celebrate the startup community. Of course here in Boston, but also the broader New England startup community. Um, so really for us, we’re creating a lot of different events and types of content throughout the year to really help different types of folks that are really part of not just starting, but also scaling a startup.

So, of course, that means the founders and investors, but also the startup employees, students, and also educating perhaps, you know, startup curious folks, folks that are interested in maybe becoming more involved in this community or starting their own venture. I love that startup curious. 

Michael: Yeah, 

Adam: Startup curious is probably the first time I’ve heard about that.

Stephanie: I think we coined the term. I’m not gonna lie. I’m pretty sure I take credit for that back in 2017. We’re like, how do you describe those people? And we’re like, curious, you’re startup curious. So I take full credit at this moment. 

Adam: Please do. Kind of turning back the clock, the initial Startup Boston Week was in 2017. I was able to read like a really excellent post by a friend of the podcast, Matt Crane of MGMT Boston. And in that write-up, Matt mentioned that the idea or the origin story for Startup Boston Week potentially actually came from a different conference that you were at. 

Stephanie: It did, actually. It kind of was a weird journey to the creation of Startup Boston, but I think that’s kind of how a lot of founder stories are shaped. You know, something happens that inspires you along the way. It’s not like you wake up one day with Yeah. I have the perfect idea. Typically what happens is you wake up one day and you’re like, wow, like why doesn’t this exist? And then that is where like the best startups are of course created. So the journey of Startup Boston is no different.

Essentially what happened was is. It was back in 2016, I was volunteering with an organization called Geek Girl, which no longer exists, but I volunteered with them for about two years. I was planning their conferences called Geek Girl TechCon, which took place throughout the United States, including Boston and then San Diego.

And essentially during the time of planning Geek Girl TechCon in San Diego, it happened at the same time that a San Diego Startup Week was happening. And… I ended up attending that conference because the founder of GeekGirl was also speaking at that conference. So, it was really just like the right place at the right time.

And I attended the conference and I absolutely loved the energy that it brought. And then when I got home, I started Googling and I found out that Startup Weeks, honestly, were happening across the globe. And they’re happening everywhere. But Boston, Boston had not ever had one, which I just found shocking because it’s Boston.

And Boston is one of the most entrepreneurial cities, honestly, in the United States. So I was just like, How is this not a thing? So that really started like the part of creating Startup Boston. And I, of course, created the first-ever Startup Boston Week back in 2017. And then when that went really, really well, I was like, “Great, now I can build a company on top of this.” And that was like a really exciting and new way of doing it and kind of something that became more of our own in terms of creating that community. So it wasn’t just the conference anymore that was loved by everyone here. It also became more of a community that supported folks year-round. 

Adam: I would say again, credit where credit’s due, not only coining phrases, but in the first Startup Boston Week in 2017. For that first year, brand new thing that Boston hadn’t seen. Y’all saw 200-300 registered attendees for that first, which is nuts. 

Michael: And I guess to a certain degree, it sort of talks about that sort of pent-up demand for something like Startup Boston in Boston, right? 

[00:04:45] Stephanie: I definitely think that Startup Boston Week is super unique here in the Boston and of course New England area because it really brings people together across different industries, across different company stages, across different departments. There’s a place at the table for you here at Startup Boston Week and also what we do year round at Startup Boston, of course. I mean, that first year of creating Startup Boston Week back in 2017, there were a lot of people that signed up. Most of them didn’t sign up until the week before, which is, of course, gives a lot of people anxiety, which is me. It gave me anxiety. Me, I am people. I was like, oh my word, is anyone going to show up? And then, I mean, the night before the first ever Startup Week, I did not sleep a wink at all. I vividly remember that first morning, that Monday morning of Startup Boston Week. It was like an hour before go time and no one was there yet because why would anyone be there an hour early? Right, an hour early, yeah. But I’m like panicking. I’m full-blown panicking. Like, I am calling Um, one of the guys that was on my team at that time calling him being like, I don’t think anyone’s gonna show up.

I don’t know what to do. I think, like, the best piece of advice he gave me, he was like, “Steph, even if one person shows up, it’s really gonna impact their life and it’s gonna be okay.” People are speaking here because they want to give back to the community and they want to help folks, like, start and scale their company.

It’s gonna be fine. And somehow, like, that just really resonated with me and that also is really kind of how we plan all of our content now, you know, as we go seven years later. We, of course, want to bring a lot of people together, but I think, like, the core of that with all of our content is, even if it’s just a small group of folks, as long as we’re giving it 110 percent and we are really impacting that person’s life, we did our job.

Like, our job is to go connect those folks and really give them the tools they need and answer the questions they have and I really think that that is still an important part seven years later and really something we strive to bake into all of the content we’re creating during startup week and also year-round.

Michael: When I look at it, and of course it was the first time I went this year. It was so vibrant and so energetic and I think it was exactly what you’re talking about. You have people across the entire spectrum of startup stages, right? I mean, people with literally just with ideas, people that don’t even have ideas. They just have some, some technology they’re playing around with, and then people that have fully banked businesses that have funding and the whole thing. And it was really interesting to just see that sort of mix of people, that energy. And I think it, in a way, because it has that variety, it created a, a real sort of snapshot of, of that Boston ecosystem in a way that I hadn’t seen in other events. Like, because if you go to something that’s more maybe VC oriented and everyone’s at the same stage. You know, yeah, there’s a lot of like, oh, let me learn from each other. But there’s not this sort of appreciation for the Boston community as much as it is for Startup Boston Week. I mean, maybe some of it’s by luck and a lot of by judgment. But whatever you created over the seven years is really incredible. And even as, I mean, I call myself sort of an entrepreneur in my 30th year of running a business. I felt that energy and was like, hey, this is this is a great community to be a part of. 

Stephanie: Thank you. I really appreciate it. And I do think a lot of it to your point is also there’s a lot of intentionality that goes into building a community and also just creating what the persona of that conference is, like what is going to be the atmosphere when you walk into it, right?

For us, we didn’t have a lot of money, especially in those beginning years of planning a conference. You have to figure the first two, or three years. We weren’t getting a lot of sponsorship money. The first year, we, we basically had none. The second, third year, maybe a little bit. Enough to pay, pay like website fees, but nothing crazy.

So, when we approached planning the conference, we had to think about it on, Okay, we can not have an open bar. We can not have anything to razzle and dazzle, folks. Let’s go back to the core as to why this exists. And I think it really forced us to get so intentional about let’s make sure these attendees are having a great experience in terms of what they’re learning, but also how they’re engaging with one another.

And let’s really make sure that when folks show up that they immediately feel at home. I think a lot of that, too, just kind of comes up from, like, my upbringing as well. Like, when I was younger, I would just move around a ton. So, like, I moved, like, eight times in the first seven years of my life. you know, uh, beginning of elementary school, like, I didn’t really have, like, a good friend group so I also kind of, like, knew what it felt like to go into a place you just don’t know anyone and, like, you just want to feel like you belong, right?

And I think just kind of taking that mentality and being like, okay, how do you approach this as an adult when you’re, like, forcing other adults to really open up and talk to one another? It’s a unique way to, like, think about it but I think it played a huge role because I was like, well, We have no money and we have a lot of people that want to go and mingle with one another, so how do we go and make that magic happen?

So, I think in a weird way, because, like, we didn’t have any money to go plan the conference, like, it also was our greatest strength because it really forced us to make it so that the content and the networking experience was excellent. Because we couldn’t mask it behind buttloads of money and free booze and free food. We had to make it good. 

Michael: Yeah, the open bar is the tool that almost everybody else uses to sort of get people to talk to each other. But then you don’t remember who you talked to and what you were talking about. Yeah, yeah. You created a great event that does create those connections. And I mean, I’m still sort of emailing and on LinkedIn with some of the people that I met months ago.

Stephanie: I love hearing that. I love knowing that you’re still chatting with folks. This makes me so happy. And I also love it, too, to that point. Like, I love knowing that folks, like, come back year over year, right, and that those folks that you met at the conference, you’ll probably then bump into them in 2024 and see them again or maybe grab a coffee intentionally.

This time, maybe those folks can introduce you to other folks that they’ve met over the past year as well. And I just love how it grows like it makes me so excited. That’s why we do this. And I really do. I think that was potentially the greatest strength that I saw kind of coming in, which was it. In this case, the opening party.

Adam: It was my first entrance into startup Boston Week, but also really I think maybe one of the first community events of that style that I had attended in not a, hey, I’m fresh out of college and I’m seeing what’s going on way, but 

Michael: What, five years ago, right? 

Adam: Oh, yeah. Yeah, yeah. Five years ago. Right. As I round out 12 years with TSP, but, uh, exactly. It was really Heartening to see how like open people were that there wasn’t like a shyness. Nobody was kind of that like middle school dance people waiting to be like you had camps of people. It was a lot of folks just kind of coming up being like, Hey, what do you do? Hey, this is what I do. And I feel like that. Is a very intentional culture that you spent the last seven years creating, and I think with some of our previous conversations, you mentioned that in the beginning, it was not only intentional, but it was a forced event as part of this. What did that look like? How was that process and Because I really do think that informed how the event grew over the last number of years.

Stephanie: Yeah. Yeah. So, the first three years of the conference, we actually did this 2017, 18 and 19 and then 2020 was virtual. And, but those first three years, what we did was the agenda was a bit different. So we actually blocked an hour and a half for each session. With 15 minutes in between and we knew each session was only going to be an hour long.

So what you did was, let’s say, you know, you had one session. It ended at 9 a.m. The next session started at 9:15, right? So you would go at 9:05 a.m. And you would go to the front of the room, and it would be, oh my god, it would be so quiet, like you could just hear a pin drop. And you’d be like, hey everyone, I’m Steph, how’s it going?

And I’d be like, “you know, I’m like, I’m, I’m alright.” Like, what is this girl doing here, like, who is she? And then you’d be like, great, like, alright everyone, now I’m gonna wait for you to all stand up, and you were just like, Kind of like do this dip and like raise your hands up to the ceiling and they would all look at you and you’d be like Yeah, so stand up and you would just wait because I can win at a staring contest you like awkward I will win and they would stand up eventually and you’d be like great turn to something You don’t know and introduce yourself and like that’s all it took.

It was like someone going in the front of the room, breaking the silence, forcing them to talk to someone they didn’t know. And then, all of a sudden, the room would get really loud. And we would just do that in like every single room. And at that time, we didn’t have a lot of volunteers helping us stay up.

Now we’re blessed with so many incredible people helping us at the conference. So I’d go to one room. Then I’d go to the next room. And by the time, by the time you’d get to the Thursday, so day four, you go to the beginning and you would do it. And you’d have like a couple guys in the front being like, Oh, she’s gonna do it again.

I’m like, oh, you bet I’m gonna do it again. And then essentially, like, we, we made the session hour and a half because, you know, as I mentioned, like, end at 9, going at 9. 05. Technically, the session would start at 9. 15, but we actually never kicked it off until 9. 30. So they had 25 minutes to chat with one another.

And we did that for every single Session every single day. And we did that for the first three years. You know, there are some people that definitely didn’t like it. You know, there’s some people that would just ignore you and just sit and that’s fine. It’s their prerogative. You can’t go and like force people.

Right. But the majority of people did do it. And I think those are the people that got the most value out of it. And I also think that there is like a blessing for, for a lot of folks. When they’re given permission to go and talk to someone they don’t know Because then they don’t have to feel awkward going up to someone I think because that was instilled the first couple years That just kind of started becoming part of like the conferences persona.

Michael: It’s interesting. I mean, a lot of the dynamic it’s almost like the first week orientation at MIT. There was a lot of like a lot of those things like get to know each other find your roommate all this kind of crazy stuff Right, but actually in the adult world in the working world. It’s not like you go into a company and they’re like Here’s your onboarding day like get to meet everybody like it’s like here’s your computer.

Here’s your desk I think it’s in a way like what you’re doing is kind of seeding this energy as part of that community Like you you have to get the ball rolling who better to do it than you that sort of energy, you know It is is contagious but I think what we find as we talk to more people in this startup community is If everyone’s sort of left to their own devices, they don’t really talk to each other. They don’t sort of Engage about the really deep conversation and that’s, you know, when we have Kylie and Matt on previous episodes. You know, it’s really interesting because you have to have these people that are kind of the center and bring people together, kind of infuse that energy. But once it’s there, it becomes like this little ball of like, it just kind of propagates on its own. It starts to kind of create its own community, which is really neat. 

Stephanie: Yep, I think there is definitely something in terms of like what Kylie and Matt are doing. It’s incredible. Like Kylie, she does, I think, that potluck, right, where it’s, you know, invite only, but she’s bringing the right folks into that room. And I think because they’re into that room with the same mentality of the founders that want to help one another, so many incredible conversations will naturally happen there because It’s the right people at the right time invited by a common person. I think the best startup communities are really built by folks like that, like through what Kylie and Matt are doing.

And there’s so many other incredible leaders in the greater Boston area too that are really playing their part in supporting it. And it’s been awesome just to watch Boston, honestly, throughout the years and how it’s really grown because it wasn’t exactly like that when I first entered it back in 2017.

It was a different type of Boston startup community. So it’s been really exciting. Um, just to kind of see how it’s changed and evolved and how it’s become more of a city that’s open to sharing with one another. And I think that’s what’s really played such a dramatic And I think that’s a really important role in terms of shaping us as a startup hub and also why so many incredible startup events are now happening here, like every single day.

Adam: It’s great. Pivoting off of that, I was introduced to Startup Boston as part of Startup Boston Week, which is five days in September. But it is now beyond that. It is year-round. So, how is Startup Boston available for the community outside of the big conference, which is the easy thing to look at? 

Stephanie: So, really from our end, we connect our community a few different ways currently. So we of course have our newsletter, which goes out every other week. And that really is highlighting the resources and events that are happening throughout the startup community. Um, about 20,000 folks are subscribed to that. And that’s currently how we measure what our community is at this moment.

We also do a lot of different types of events throughout the year. Everything from our deal flow mixer, which matches founders and investors. It is so really great for growth stage startups to our co-founder matching events, which are great for idea stage, early stage founders that want to, you know, really grow their startup more.

But we also have a lot more coming 2024, which I can’t share yet, but I’m so excited for what I can share with you. You can subscribe to our newsletter and stay in the loop once those are public. Hey, there we go. We just want to connect everyone year-round. And that’s kind of like where a lot of like those initiatives are coming, coming through is how can we connect folks more? How can we really help broker that access throughout the startup community? So folks are chatting with the right people, whether it’s potential employees for the team, potential investors. Potential partnerships for their startup. Like that’s really kind of where all of those programs, um, are being inspired.

Michael: And I see you a lot on, on social media, on Instagram, sort of talking about like this, this is what’s going on this week, you know, in the startup community, which I think is great. Is that something that’s relatively new? Have you kind of increased that recently? Maybe it’s just my Instagram feed. I’m like, you know, there’s more stuff, but I think it’s like that heartbeat, right? Which the community needs to sort of. See what’s going on week by week and know what to go to or… 

Stephanie: you know, Mike, I love that. There’s more stuff in my Instagram feed. Thank you. I love you. Yeah, we’re doing something right. The algorithm is working. 

[00:19:46] Michael: Yeah, right. Exactly. 

[00:19:48] Stephanie: Essentially, what’s happening from this and as we have been maintaining our event calendar for about a year now, the event calendar has really been a labor of love from the Startup Boston team’s end in terms of aggregating all of the events happening across the Starb ecosystem. Some of it folks submit some of it we just go through manually all the Starb calendars and kind of pull it together. We’re human, we of course miss some of it, but we, we try our best, like we try to really put it all together in one hub.

And, essentially after Starboston Week, um, one of the initiatives that I really have wanted to double down on was making it clear This is the source of truth. Like everyone, please be a part of it. Submit your events because it’s really tedious as a founder or anyone. To go through calendar after calendar after calendar to figure out where to go to find these events, right? So that is really kind of what, where that effort in terms of there’s been a lot of stuff on my feed has really come from. It’s more so just wanting us to kind of really highlight, hey, we take hours every single week to do this. If your event is missing, please submit it to our calendar, we will add it, and that way more folks can go find your event and register it.

We just want to make it easy, because that way folks just know, hey, these events are happening in the Starb ecosystem, maybe it’s a good fit for me. So, If anyone’s listening to this, go to startupboss. org slash events and submit your event. 

Michael: And we’ve talked to people over the years that talk about this, the startup community and the concept of this sort of one calendar that rules it all and it’s almost never been able to sort of crystallize so great that you and the team there are sort of taking that charge and making it happen because I’m sure that’s a very valuable resource.

Stephanie: Yeah, basically after Startup Boston Week, I was like, you know what, we’ve already started doing this, like, let’s just double down on it, let’s make it known, and so we’re really just kind of promoting it more and more, but at the end of the day, like, that’s really just the focus of that calendar, it’s just to help bring it all together, um, and then of course, like, we’re chatting with the community as well to kind of figure out, hey, what else do you need, like, what else needs to be highlighted, so, We started highlighting like what accelerator drives are currently active and live.

That’s been like a new series that we started both on Instagram and then also on our blog to kind of highlight, hey, these are the accelerators that are currently accepting applications. These are the dates that they stop because that’s also been a huge pain point for founders that we also heard was, well, how am I supposed to know what is open then when unless you have Google alerts, it’s really difficult.

So we started doing that, and that has gotten a lot of traction as well in terms of other accelerators reaching out to us, being like, Hey, you missed ours! And we’re like, thank you for telling us, like, that is what we want to know. Now we can add it, we can go do a video on Instagram, we can really make sure, like, folks know, um, that that accelerator is approaching.

I strongly encourage, like, everyone, if there’s other things that they wish were easier to find, like, we really want to make sure that we’re creating that for the community, like, Our job at Startup Boston is to really bring it all together and to really make it easy and that way you don’t have to go and Set up dozens upon dozens of Google alerts and hours researching, you know, 15 subscribe exactly, exactly like there’s a team on our side of about 50 volunteers that volunteered their time year round because they want to support this community that’s currently in their backyard. Those are just kind of two examples of what else we’re doing to help support.

Michael: We always come around to this topic eventually on our own podcast, which is which social accounts do you see as being kind of the thing that happens, right? Previously known as Twitter, which everybody says and will continue to say for the next year. Threads, IG, like, do you think, I mean, Instagram is where, you know, I see, see you, but is that sort of where you think that most of the startup community is sort of finding these things?

Stephanie: Yeah, so I will definitely say the medium I find the most valuable is LinkedIn. Out of social traffic, a lot of traffic is actually organic for us. If you type in Boston startups, we show up as number one on Google, but afterward it is through LinkedIn. Instagram is really the next medium that I want us to focus more on.

So over the past, I want to say three, four weeks, that’s been the one we’ve been doubling down on because I see it as the medium that we really can do so much more with. And I really see that as kind of being what could become our water cooler for like the startup community in terms of really highlighting what’s happening. And also we have a Twitter, but I’m not a big fan of that one. 

Michael: I don’t know anyone that is, to be honest. 

Stephanie: Twitter has just kind of stalled. It hasn’t really done much for us. Honestly, Twitter used to really help us with signups, especially for Startup Boston Week this year. It did not, it was all through organic search, um, or LinkedIn. I absolutely love LinkedIn. I definitely need to get a bit better with my personal LinkedIn account. I used to be really great at it. And then I think after a startup week, I started to take more of a hiatus. I was like, I’m so tired. 

Michael: Yeah, there’s only so much we can do. 

Stephanie: So I’m going to get back into it. But I do think that concentrating on Instagram is another great thing for all startups to do. Not just ours, but I really think that there’s a lot of value in that. I think, uh, great examples, honestly, to me are like the B side. Um, which is like the Boston Globes version of their Instagram handle, but I think what they do is like very well done. Same thing with Morning Brew, um, in terms of how they wrap up, like what the stories of the day are. Another one is Hello Prenup, which is a Boston-based startup that was on Shark Tank, but their Instagram and also their TikTok stories are very good. So, if you’re looking for inspiration, I would definitely recommend checking them out as you think about how to, how to do those.

Michael: Hello, prenup. That’s a new one for me. 

Adam: And if you are a Twitter expert and you’re listening and you have some thoughts, powerup@tsp.me, drop me a line. I got some questions. That’s right. Please help us. Tell us. The community has some questions. But as you’ve been going through building the calendar, looking at all the events going on, for those who maybe are looking to create an event or wanting to attend, I guess. One question that I would have is, with what you’ve been seeing, have you been seeing an increase in more in-person events and a decrease from virtual? Is it keeping in parity? What do you see as the most, maybe like, effective for people? 

Stephanie: You know, what was so intriguing, I’m going to use Startup Boston Week as an example, because that one we give folks the choice. It was really down the middle. What was intriguing is for speakers, we had 294 speakers during Startup Boston Week, only 40 of them were virtual, so the majority of speakers were in person. But then if we look at the attendee breakdown, it was very, very like kind of down the middle in terms of who is virtual and who was in person.

Some of it was, of course, based on hours, right? If it was like 8 a. m., they were primarily virtual, which was a learning moment for us because the year before it was a little different. Again, like sometimes later in the day, if there wasn’t a networking event, for example, it was also primarily virtual, right?

So I think if you want to drive that in person attendance over virtual attendance, you really need to be thoughtful in terms of what opportunities are you giving those folks to really network and engage with one another in person. I don’t think that’s groundbreaking news, but Honestly, it wasn’t really something that we were very thoughtful of when we were planning some of the events We were thinking of networking throughout the week, but I wasn’t approaching it with the mindset of how do I get in person?

High every single day at all hours of the day, right? And I do think that that planning is different than how do I go and help folks network? So 2024, which you already know we’re planning We’re just approaching it with a different thought now in terms of how do we go and get more folks to attend in person throughout the day, every day, but otherwise, the virtual and in person attendance… Were both high. It ebbed and flowed. And likewise, we have done webinars throughout the year that also have reached somewhere between 100 to 200 people online, depending on what the topic is. We’ve also done in person only events throughout the year, which, again, have also reached 100 to 200 people in person, depending on the topic.

So, I do think that there is a need for both. Depending on what you end up planning, my two cents are this, if you are going to do something in person, you really need to think about how can you go and make it special for in person folks, like how are you going to go and help them create, uh, those in person connections so that it’s not like, uh, I just showed up for a presentation and that’s it, because commuting in Boston’s a pain.

I don’t know if anyone’s taken the T lately, but it’s really not that great. So, I would definitely think about that. Um, and then also, of course, the timing of your event. If you want to do it at noon or 1 p.m., unless you’re inviting a really well-known investor or CEO, do it virtual at noon or 1 p.m. If you’re going to do it in person, do it at like 9 a.m.

  1. or 5 p. m. You just have to think about the commuting time that’s going to work out best. For someone’s schedule picking up their kids their work anything like that in my personal opinion though I also do think that anything at noon and 1 p.m. People will forget about more often 

Adam: Yeah, or something will happen and you’re like, oops, not anymore. 

Stephanie: Exactly. Like I think at that hour, it’s just so weird. It’s like if you’re on the East Coast, that’s also like the West Coast morning And also you’re like do I want to sit at a computer during this hour? Do I want to go outside before the sun sets at four? That’s just my two cents But again, like I think it depends on the topic the person and the structure of the event You got to make it worth their time and respect their time and also respect their attention Like what are they going to be sacrificing to attend your event? Like what are they going to get in return? Right? And I think as long as you’re thinking of it through that mindset You’re already going to be set up for success. 

Adam: That’s really good feedback of like, especially for the in person make the value, not only the content, but what the, Hey, you’re around a whole bunch of people be a, also an additional focus kind of going back to the give places for people to create that innate community to talk to each other, I think, is really, really valuable. 

Michael: The other thing, which, which is really fascinating as you talk through seven years and, of course, COVID in the middle of it, and I think we’ve seen this with anyone that’s been doing events, you know, it’s almost like the agile process of having to iterate, right? And so Startup Boston is a business and in a way its own startup, right? I mean, it’s, yeah, it’s a seven-year-old startup, but at the same time, like you’re having to Do this huge events having to change it as you know, all of this data sort of comes and I’m just really fascinated whether or not you sort of almost look at startups that are going through their journey as almost like a mirror of the types of things that you’re having to do, you know, within your business and and as you’re running it.

Stephanie: We do, I think. There’s something to be said about our business model, of course, versus tech startups model. So my background prior to StartUp Boston was in the tech startup world. So I do see quite a few differences in terms of how that tech can scale a little bit faster. Whereas right now where StartUp Boston currently is in, it’s all very services based. Do we have the manpower to do it? And to your point, Mike, I would definitely love to figure out. With some of our initiatives in 2024, other ways that we can scale that don’t necessarily equate to additional manpower. And that way our organization can become more sustainable, can ideally pay a few folks on the team full time, and that way this can live on indefinitely, right? Like, that is the ultimate goal of what I would love to do at Startup Boston. I’ve learned a lot of stuff at my previous tech startup companies that I’ve definitely taken over to Startup Boston. Some of it is, you know, Oh, that worked out really well. Like, I should definitely remember that as we start to grow Startup Boston even more.

And some of it, of course, is what to not do. What is unique about my journey is just from working at two different tech startups, both NDash and Goldcast. Is that I saw both of those from a very early stage, right? I saw n dash as a co founder I joined gold cast and was just a mere few months old as employee number 11 And to watch both of those startup journeys were incredibly different and dash we were bootstrapped Gold cast I joined right after their seed series and was there through their series a and it was incredibly Intriguing to watch both of those companies grow, ebb and flow.

And again, to your point, Mike, there were a lot of learnings in terms of what those startups did. That I have definitely carried over to what Startup Austin has done and also just chatting with different founders throughout all of the startup weeks that we’ve done all of the events we’ve done a lot of the pain points that those founders have gone through that attend Startup Austin events.

I can definitely relate to just from my own journey and it definitely helps me. Either give them my two cents or at least just be a listening ear and being able to empathize right with them. Even if I don’t have a solution, I can understand what they’re going through. 

Adam: Last question for you, and I have some thoughts on what you may say. What is the best piece of advice that you can give to a founder and someone, an operator, the startup curious to try and find community in Boston? To make sure so they don’t feel alone and like. bashing their head at all these things that some of us have already seen and felt and may have some two cents to to part with.

Stephanie: So what I would personally do is I would first independently write a list of kind of what you want out of a community. I think it’s really important when you go into quote unquote community research of knowing what you want, right? Is it someone to bounce ideas off of? Is it someone just to hit up for a lunch every now and then?

Is it someone who is more senior than you, who has been through more than you, like? What do you want out of it? I think it’s really important first and foremost to write that down and to identify that. Then the second thing is I would research kind of what communities are out there based off of that list.

Of course, if you’re in the Boston area, you can go to start Boston, but if you’re, you know, West coast, you’re going to find different websites out there, of course. So then I’d go research it and then I would just go attend different events. And after each event, start journaling. What do you like about it?

What did you not like about it? And kind of honestly start grading your experience in that way to know, hey, matched off of your original expectations. What did you get out of it? I don’t think that every community is gonna be the perfect fit for all of the things you want. Mm-Hmm. So I think it’s really important to find like those two communities that can potentially check the most boxes, right.

You’re probably going to find one community that’s your learning community and one community that’s like your networking. I have my camaraderie community. I would personally approach it in that way. It’s a very methodical way, but that way you’re not necessarily wasting any of your time because as a new person in the startup world, regardless as to what your position is, time is valuable. You cannot get it back. So I would definitely take that approach in terms of first knowing what you want, figuring that out, researching, and then finding the two that can check those boxes the most. And then of course, sometimes you might pick wrong, in which case just understanding Why you picked run being able to identify it quickly because that way you can always go find a new one if it’s not delivering what you need and additionally, as you grow in the startup world, your community will most likely change as well.

The community that you have the first three years. In startup world will most likely not be the same community that you’ll have in your year seven and eight So I think just also identifying And knowing when you stayed at some place too long is important because if it’s not challenging you and if you’re not learning Then you’re also not going to grow.

I think that’s also equally important 

Michael: I love sort of concept of visioning the community that you want. It’s such a key concept in entrepreneurship You know, which I mean it’s taken me probably 20-plus years to learn. Like, I think a lot of people in the entrepreneurial, entrepreneurial world, like have a great idea and then sort of wander this sort of meandering path, thinking that the idea will take you places, but not necessarily have a specific destination in mind.

I think that’s really insightful to say, well, look, you know, this is part of your startup journey. You need to understand really what you need out of it. Because as you said, it’s not just one big community, just a melting pot. It’s made up of all of these sort of subgroups, which have different purposes, different stages, different connections.

That’s really fascinating. 

Stephanie: Thank you. Hopefully, this helps someone. 

Adam: Definitely. Well thank you again, and that is the time we have for this episode of PowerUp. Uh, I want to thank everybody for listening, and we will be back at it again next time with another fantastic guest. In the meantime, you can find everything that TSP is up to over at our Instagram, which is probably our platform of choice right now at Tech Superpowers or on our website at www.tsp.me. Where can we find you and everything that Startup Boston is up to? 

Stephanie: Definitely go to startupbos.org to check out everything that the organization is up to, to check out our newsletter, or you can follow me on LinkedIn. My last name’s Roulic, R O U L I C. 

Adam: And maybe you, too can get a little bit more stuff in your feeds, letting you know of everything that’s going on. Until then, from everybody over here at Tech Superpowers, we’ll talk to you soon.

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