How This 25-Year-Old Entrepreneur Launched One Of The Biggest Startup Events In Boston

Stephanie Roulic had many questions when she first launched her company. So, she created an event to answer them

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A new startup founder at the age of 25, Stephanie Roulic had many questions.

How do you build a team? How do you get users? How do you gain traction without any funding? How do you pitch an investor?

The list went on and on.

She read many blog posts, some of which were helpful. But the problem with blog posts is they don’t talk back. You can’t ask them follow up questions or have a back-and-forth dialogue.

So, Roulic started attending some startup-oriented events in Boston. Again, some of them were good, but they were a bit too niche and still not answering her questions.

Tired of looking, Roulic decided she would find the answers she — and undoubtedly many other startup founders — were looking for by creating her own event.

“I was new to the startup world and had no idea what I was doing,” Roulic, the co-founder of the content software platform nDash, told me during an interview. “I was looking to network with other people going through similar situations and trying to figure out how to build a company, and then figure out what their job was because I had no experience doing my job. Basically, I made the conference to bring together people that were new.”

Curiosity is an amazing thing.

In its first year of existence in 2017, Roulic’s homemade event Startup Boston stretched five days, featured 50 different sessions and brought a whopping 2,300 people to the event.

Now, Startup Boston has grown into a household name in the startup ecosystem.

In its third year running, the event featured 64 events and almost 200 speakers over five days, with around 3,000 people in attendance.

The organization has begun producing more events year round and could one day launch into other cities as well.

The thing is, when Roulic, who is now 28, first created Startup Boston only a few years ago, she didn’t have thousands of dollars at her disposal, a huge network or a whole team to back her up.

Roulic was on her own in the beginning, but with a strong work ethic and smart strategy, she was able to produce an event that has cut through the noise and turned into something special.

Here is how she did it.

Finding Speakers and Venues

Events can’t happen without speakers and venues, and Roulic had set a lofty goal.

She had seen a friend of hers run San Diego Startup week with many events over several days, and decided she would try and do a similar format for Startup Boston.

That means she needed many speakers and multiple venues.

Although she had a lot to do, Roulic didn’t panic. She remembered why she wanted to launch Startup Boston in the first place — to answer the questions she and numerous other startup founders had, and to help people solve problems.

“Those are the questions I created the events around and got speakers for,” she said. “If I was going to talk to anyone in Boston, who would it be to answer these questions? And thats how I started scouting speakers.”

Amazingly enough, Roulic found people were more than willing to pitch in.

“The speakers wanted to help because they cared about the Boston startup community,” she said. “People volunteered their time because they wanted to help other entrepreneurs succeed.”

It was a similar tale on the venue side.

Roulic, with practically no budget, had to find places that were willing to give her space for free.

So, she positioned the event as an opportunity.

Roulic told venues that she wanted the event to serve as a place where entrepreneurs and others in the ecosystem could come together, and that she would be trying to bring a lot of entrepreneurs to their doors.

Venues liked the idea and took a chance on her. Some like the Cambridge Innovation Center, one of her first partners, are still huge supporters of Startup Boston today.

Building A Team

For the first four or five months of planning, Roulic was on her own. She accomplished a lot, but she knew she would inevitably need support to put on such a large event.

This, however, was no easy task.

After all, she had launched the event in order to meet more people in the startup world.

Roulic took the natural first step and reached out to her existing network. There, she found a past contact to help her with some graphic design work.

Roulic also launched a website for the event even before she knew it was a sure thing.

As word spread and the website got around, there were more people in similar situations as her that loved the mission behind the event and wanted to see it succeed.

They agreed to help and some of those early team members are still part of the team, which today has grown to 20 people strong including marketers, designers, content writers, social media people and advisers, as well as a full programming department and partnership and outreach department.

Marketing The Event

Marketing is another huge part of putting on an event because you need attendees.

Roulic had to figure out how to get the word out in a congested event market like Boston, where events are held frequently. She only had a $300 marketing budget, which wasn’t going to get her very far with things like paid ads.

It was time for marketing 101.

Roulic found everyone who had a mailing list that she wanted to reach and asked the organizations or lists to be event partners. If they told their audiences about Startup Boston, they would be part of the event and have their logos featured at the venues and sessions.

Roulic looked for other potential stakeholders like colleges and universities that might be interested as well.

“It was finding people who were also excited about Startup Boston and asking them to share,” she said.

Building The Event Bigger And Better

In the first year of the event, Roulic said she had no expectations — it was a matter of could she make it happen and could she get people to show up.

But after 2,300 people showed up the first year, Startup Boston had serious momentum.

As most startup founders will tell you, the first sign of success is not the time to pump the brakes.

As the event has grown, Roulic and her team have not stopped trying to make it better.

In year two, Roulic put one of her first organizers in charge of programming to solely focus on what type of speakers and sessions Startup Boston should offer.

“The main focus after the first year was the quality of content and how to structure the event,” she said. “We decided that if you can read about something in a blog post or if someone else is already putting on this event and it’s amazing, then we are not doing it. We need to put on events that attendees are, for one, going to build an incredible network from because we are getting awesome people in same room, and two, it’s worth their time because they are learning something they couldn’t learn in some other place.”

This year, Roulic said the team intentionally focused on making the event easier to navigate.

Startup Boston divided its events and venues by different startup job categories and lifecycles of a startup.

Now, the event is not just catering to first-time founders, but also to employees in various positions at startups and mentors and serial entrepreneurs looking for something new.

In 2020, Startup Boston will focus on launching new events throughout the year in addition to its flagship startup week.

Roulic said she also wants to focus on ramping up the buzz around Startup Boston so people all over New England and New York City will want to attend.

She is also thinking about how Startup Boston could expand geographically.

Roulic definitely sees the organization moving outside Boston and into places like Lowell or Western Massachusetts. As for further expansion into other cities outside Massachusetts, she didn’t rule that out either.

How To Create A Great Event

A lot goes into creating an event — the venues, the team, the speakers and the attendees, just to name a few.

But as Roulic has shown, it’s not impossible for a 25-year-old newcomer to the startup scene to make a big dent. For others inspired on creating or running events of their own, Roulic has some advice:

  • A lot of people focus on how many people they can bring to an event. That’s just the wrong way to do it. The minute you play for the numbers game, you are going to diminish quality. Before Roulic started setting up the sessions at the event she asked herself these questions: What questions do I have? Do other people in the startup space have those questions too? And is there anyone else already doing this kind of event, and doing it well? If so, there is no need to do it again.
  • Find speakers with different perspectives that are really engaging and going to speak well.
  • Find a kick-ass moderator. A moderator can make or break a panel. A lot of people underestimate the importance of a good moderator, but they can make your event shine or take it off course.
  • Find people that value what you are doing, and partner with them. That was the key behind getting venues and speakers to volunteer and help make the event happen.

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Full-time journalist and Content Strategy Lead at GoingVC writing about business, the economy, startup culture movies, sports and much more.

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