Stephanie Roulic grew up in Massachusetts before her career as a Founder, startup event organizer, and early startup employee. It’s easier to just leave it there for a new audience than to detail the first three years of her childhood growing up in Moscow after the collapse of the Soviet Union. Or the chapter in Malaysia where she attended preschool & part of kindergarten before moving to Thailand to finish kindergarten and attend first grade. After all that she boomeranged back to the Bay State where she was born to settle in Billerica. Whew.
But to skip over those first 8 formative years is to miss some important aspects of what made Stephanie into the self-sufficient, initiative taking, hyper organized powerhouse she is today. She got used to being alone. She read. She wrote stories and screenplays. She created fake summer camps with storylines and agendas. She was planning conferences long before she knew what they even were. She visualized, pondered, and practiced which fostered a strong imagination. She dreamed of making movies. Because there’s no business like show business.
She also learned some really valuable skills that would help her later in a scrappy startup career. Her parents instilled a culture of saving in Stephanie and knowing the value of a dollar. When she received her $0.25 weekly allowance for folding clothes or other household chores, she decided she wanted to save up for a toy Barbie house. It didn’t take long to do the math and figure out she would be saving for quite some time before she could afford it. And it would cost all of those savings. An early lesson in opportunity costs! So she chose to keep her runway intact and…kept saving instead.
Stephanie was worlds wiser than most when she set off for UMass Amherst where she majored in Communications and minored in Spanish and Film Studies. She graduated in 2013 looking to launch a career in Marketing. She was open to a variety of marketing responsibilities like social media, blogging, etc. Except it took her almost 8 months to find a role as a lot of the companies she interviewed for were looking for someone with “experience”. Isn’t it funny how that works?
She landed a part time job at nDash, a new marketing agency, which she found through one of the best peer to peer marketplaces of the 2010s: Craigslist. I want to say for the record that I know numerous people who found jobs on Craigslist in that period. It wasn’t weird! The record must be set straight for Stephanie before any of you youngsters pass judgment.
The nDash opportunity came about by chance but it was one of the best decisions she could have made. Over the next two years she put her head down and worked really hard. She got along really well with the team, including Founder Mike Brown, who had an idea for a marketing tech startup he wanted to launch. The nDash agency team – Mike, Stephanie, and Andre Wehe – launched the nDash software company in August of 2016. They shed the agency in the process.
Stephanie became a 25 year startup co-founder because, in her own words, “why not”. She lived in a small apartment in Quincy. She hunted her own food from the Blue Hills Reservation and caught fish from the Boston Harbor for sustenance. Ok, I’m exaggerating a bit. Life as an early stage Founder had some lean days though! It was the beans & rice phase.
She went on to share that a lot of her best decisions in life were “why not” decisions. The same year (!) she co-founded nDash, Stephanie volunteered to help host a conference in San Diego called “Geek Girl Tech Con”. It’s lost to the ashes of conference history but it happened during San Diego’s Startup Week. She thought to herself: “why doesn’t Boston have a startup week?”
There’s a bigger startup scene in Boston. She was always wondering where to go to meet other startup founders & members of Boston’s tech community. A lot of the events she attended in the Boston area didn’t always seem to have the right audience. She knew from first hand experience there was a knowledge gap for a lot of first time Founders on seemingly mundane topics that more experienced startup folks just assumed others knew. For example, how do you talk to customers? “We all have to start somewhere and people forget that” Stephanie told me. She learned to talk to customers herself without anyone really guiding her. There were countless other 101 topics to be covered.
So in September of 2016, the same year she co-founded nDash, she started working on Startup Boston Week. Because, why not? She found a couple other people interested in helping and started working on a full 5 day conference for the following September. She told me “it had to be 5 days” and “it had to be in September”. Two mandatory requirements that she can’t even recollect why she felt so strongly about. It was a huge part of her life for almost 9 months alongside 3 other volunteers, and Startup Boston Week came to be. Oh and nDash was admitted to Mass Challenge during the same year.
You’re probably wondering how it went. Stephanie was hoping to get 500 people there covering topics like – how do you scale for minimal costs? What’s Marketing for Dummies? How do you start? How do you scale? How do you break up with a co-founder? How do you fire someone?
2,300 people registered! For the first year! After a launch like that it had to be done next year. And the year after. Fast forward to 2023 and Startup Boston has 34 volunteers, 18,000 attendees, and 900 speakers who have shared their knowledge over its 6 years. They operate events monthly 10 months out of the year and still have a 5 day flagship conference in September. That’s a scaled startup unto itself right there!
Stephanie really enjoyed her experience at nDash too. A 100% bootstrapped company, it was a great crash course on everything startups – how to onboard customers, how to teach technology product to customers, how to build a help center, and how to sell. She owned Customer Success & Customer Support. Some marketing too. She was the only customer facing person on the team! Stephanie describes herself as a person who loves starting things and, after a period where projects and functions are built out, looks for something new. Her old habits from childhood made her a perfect fit for scrappy startup life.
After almost 7 years Stephanie began to look for a new challenge. With the experience and exposure that Startup Boston had given her, she had options this time! After all the energy it took to balance a full time job at nDash and organize Startup Boston, Stephanie needed to take some time off to recharge before her next challenge. She described it as a moment of panic to be without a job but she needed the break.
She was definitely staying in Boston though. Stephanie really liked running the Esplanade whenever she could. I told her this has come up a couple times previously and she replied “It’s a vibe, it’s the best place to run.” No argument there! Living outside the city, she loves coming into town to go for a run and grab some pizza and a beer. Not with the weather this past weekend though I’m sure..
She loves how the startup community in Boston has evolved over the past 7 years. People have come together to support one another, make introductions, and help break up Boston’s reputation as a closed community. She’s found amazing advocates in the local ecosystem. People like David Chang – a local angel investor and “celebrity in his own right” she tells me. Senofer Mendoza is an investor committed to supporting women & BIPOC founders. She’ll grab coffee, hop on calls, or give people feedback at the drop of a hat. Allison Byers at Scroobious too has made a huge impact over the past couple years as an advocate for women & BIPOC Founders. Stephanie feels strongly about her program. And so many more. Too many to name!
As Stephanie figured out what to do next, she came across recently launched virtual and hybrid events startup Goldcast. She knew she loved tech companies. She knew she had the energy to do another startup. And she was fortunate that Startup Boston had helped her build her network out. She had enough confidence and support that it was “ok” to not have another job. Besides she was running a year round program involving thousands of people so…she still kind of did!
They needed someone to help them in marketing with event launches. She heard back almost immediately and interviewed that week.. Like any startup, needs rapidly shifted. They had just signed their first customer and actually needed someone to help with Customer Success instead. How did she feel about that? Sure, “why not”.
She was up front with the Goldcast team that she would help build out the Customer Success function but at some point aspired to be able to touch more areas of the business. At nDash and Startup Boston she learned that she loves building things from scratch and then, when they get built, a little bit of boredom sets in and there are more qualified specialists who would be better served to fill the role. It was a thrill to help Goldcast build out that initial Customer Success team before she moved over to a Head of Operations role.
As Goldcast’s Head of Operations, Stephanie is helping them build their hybrid events product and gets to contribute to a lot of different processes between departments. She’s excited about this role because it allows her to help build out multiple departments across the business.
Here are three insights Stephanie shared with me that has informed her work and career:
Taking Risk: reflecting back on her career, “if you can afford to take a risk, you should just go for it.” If life allows it, taking those risks has really allowed Stephanie to grow. There’s obviously some privilege to being in that type of position she admits, but a big theme of her career is taking leaps and risks that have helped accelerate her career.
Intentional Prioritization: Nothing is owed to you. You have to put in the time and the effort to manifest an outcome that you want. You might see your friends on social media going to fun places and doing fun things and think to yourself “I can go build something cool and do all these fun excursions too.” She hasn’t found that to be true. You can obviously have some fun but you have to make sacrifices too. “What do you want to prioritize? Building a company or traveling the world?” Neither are the wrong decisions but being intentional about your priorities helps keep your career (and life) organized around those goals. That shouldn’t come at the expense of your mental health, family, friends, etc. but you should be intentional about what you’re looking to achieve.
You Will Never Know Everything: you have to identify what you’re excited about and good at as early as you can. You’ll need to find (or hire) a partner in crime to do the rest. A good example is Startup Boston’s new Head of Operations – Dan Newman – a very talented builder who helps elevate their team’s culture. Stephanie’s more inclined to rifle through “to-do” lists while Dan has taken the time to explain what everyone’s working on and create opportunities for the team to connect. That’s just not her and that’s ok! That was a missing piece that she didn’t always realize was lacking.
Stephanie is really excited about her future at Goldcast and Startup Boston. At some point in the distant future she could see herself being drawn back to being a Founder. Time will tell. This year is all about helping Goldcast scale and taking Startup Boston to the next level. She feels really fortunate to keep building alongside those two awesome teams and loves the stage that both of those organizations are in. Maybe something film related in the future? There’s always time for a third act!
For more on Stephanie, check her out on LinkedIn and Startup Boston. Thanks for sharing Stephanie, I can’t wait to see what you build next!