Career Contessa - This Serial Entrepreneur's Motivation Is Completely Rooted in One Virtue—Empathy
BYJACQUELINE MCELHONE
Charlie Grosso, a true renaissance woman, has the unique ability to find a niche in the market that isn't being met—and to fill that void. Cultural competency, optimism, and a vision for facilitating human connection combine to guide Grosso to dream big, but also to execute that dream. Grosso isn't just a dreamer, she's a doer. And when she commits to a project—to a vision—she follows through. Her empathy instinctively drives her to empower other people, through any entrepreneurial venture she embarks on. No one can give better insight than Grosso herself—so here she is:
I wanted to be an artist when I was young, but my mom would always tell me “no.” Children of Asian parents are expected to be doctors, lawyers, or bankers—especially children of my generation; I’m not sure if that has changed much. I didn’t understand the “no” in my mother’s reply, so I would go back every so often with different variations on being an artist: painter, fashion designer, writer. The answer was always “no.”
Now when people ask me what I do, my answer depends on who's asking. Founder of Hello Future, writer, photographer, consultant—it just depends. Our world still has a very binary view of careers, [offering] little room for someone who has more than one passion. But an entrepreneur is responsible for juggling multiple professional titles. We’ve dubbed the entrepreneur as a “jack-of-all-trades,” but truly they are a “renaissance” person.
I’ve always been a storyteller. How I’ve been able to express that has ebbed and flowed over time, but picking out stories and working to tell them with the end goal of bettering the lives of others has remained a constant throughout my career. Being a storyteller wasn’t the initial intent, but it has been the throughline of my career. It is the core of what I do and what I love.
On Her Transition to Entrepreneurship
The plan was to go straight from undergrad to grad school. I was in the middle of interviewing for an MFA program in Theatrical Design when I had a "come to Jesus moment"...I thought, what more would I have at the end of an MFA other than more debt and the qualifications to teach (and I had no interest in teaching at the time)? Continuing down [that] path didn’t seem interesting at all. So I pivoted and started my own photography business—something I was truly passionate about.
Fortunately, I didn’t find the [entrepreneurial] learning curve to be steep. I had some great friends and mentors who were already established career photographers. They were there to help with any business questions, and I really took to the business aspect of the work. That path—the path of running a business and overseeing the success of a company—has been a foundational part of my career journey ever since.
On Why Photography Came First
I’ve been a professional photographer for nearly 20 years. Photography demands a fluency of the left brain and the right, the technical and the artistic. I love that aspect of the medium. It is inherently a paradox: the truth and a lie.
The work that I’m drawn to and [that I] create is about a moment—either a flex point in an imagined story, or the beginning/end of a story. It is a pictorial equivalent of that perfect opening sentence in a short story, the turning point in the action, that last moment before the screen fades to black and flashes “to be continued.” Photography is the last modern medium. It is one that everyone gets—especially now with the lowest barrier to entry—and I think that's pretty cool.
On Taking Risks
I often feel bad when young, aspiring entrepreneurs come to me for advice. I tell them that [entrepreneurship] is not for them if they are risk-averse. Being an entrepreneur or a freelancer is hard and full of risks. There are no road maps or safety net[s].
Doubt and I are friends, especially after 20 years on my own. I think it would be weird if doubt didn’t show up from time to time. What I think is important to clarify in the conversation about doubt is the core of that feeling and what triggers it. Are you doubting the bigger vision? The path for growth? A particular strategy or tactic that is being implemented? What is it? Is it that you looked around and saw other’s success and wonder why you have not achieved the same?
Sometimes, the idea is just ahead of its time. That doesn’t mean it was a bad idea. The market just wasn’t ready for it yet. Sometimes, the idea is great and the timing is right, but you are not capitalized enough to give it the necessary runway to “make it.”
On Pitching Yourself, And How She Pitches Herself
When you’re talking about something that you’re truly passionate about, I think it resonates with others and helps pique their interest. It may not always pan out in a grant or media hit, but it at least gets the name out there and gets the wheels turning on how we can rethink a long-standing problem that has yet to be solved.
Connecting with people on a level they can relate to is at the heart of any persuasion. Everyone has an understanding of home—even those without one, their lack of a home is their baseline understanding of this universal concept. By talking about Hello Future as a way not only for teens to land a job, but, beyond that, as a way for them to put down roots, that’s a really strong message that a lot of people can buy into.
On How Her Latest Endeavor Came About
I knew I was ready for another career shift and I wanted the next big thing to include: working internationally; using my diverse portfolio from two decades of professional experience for the benefit of someone else, a cause, something that is beyond a corporate bottom line.
I’ve been really drawn to the Middle East and have been watching the region closely since the Arab Spring. When the refugee crisis hit its peak in 2015, I felt it in my core. Home and identity are ideas I wrestle with personally, especially as someone who was sent to the U.S. by her parents at 11 years old. It informs my work at every turn. And I knew I could contribute to the crisis in some way. This lead to a move to Istanbul in 2016 and a lot of in-person conversations with refugee families in both Turkey and Iraqi Kurdistan. Hello Future was founded on what I learned first-hand in the field with refugee families.
Hello Future hits multiple notes on refugee response and development in innovative ways. First, in who we’re working with: refugee youths. Youth are the most underserved and, yet they are at the most critical juncture. Second, in what we’re actually providing: digital skills, yes, but also a platform for them to tell their own story, first-hand. The refugees’ needs extend beyond the tangible, such as education, to include the psychosocial: to be seen and heard, and have an opportunity to self-represent. To provide that outlet for refugees and add different color and tonality to the overall refugee narrative is very important to me.
...And What They Do
We aim to create lifelong learners and prevent a lost generation of youth in a region that is ripe for radicalization and the other trappings that come with feelings of hopelessness. Hello Future is a holistic program, one that has been designed to scale as a plug-n-play companion to larger NGO development efforts and via our own expansion efforts with local, accredited teachers.
We provide teens living in refugee camps (currently, Syrian refugees in Iraq) with mobile phones, connectivity and the training on how to properly use the technology and the Internet, the framework for how to engage online, and the essential tools that govern a digital life.
In the refugee context, where resources for education, communication, and self-expression are severely limited, the benefits of technology and the Internet can really amplify opportunities. We start there, in digital literacy and digital citizenship. Building on this foundation, we hope the teens will find positive ways for self-expression, add to the narrative complexity of the refugee/displaced dialogue, continue their education be it in a formal or informal setting, and have the necessary skills to compete in the 21st-century economy.
On The Present—And The Future
Fostering connections, empowering others, and actively contributing to a more diverse narrative are core to what I’ve dedicated my life to. The topics change as do the strategies, but the goal is the same. It was challenging to break through the noise and get people to pay attention before 2016 and now, 570+ days into this administration, the challenge of getting attention—be it from a media perspective or from donors,—is even harder. The work is important, maybe more now than ever, but the environment feels ever more difficult.
It’s hard to know what the long-tail effect of your work will be. This morning I read a review of Crazy, Rich Asians and it talked a lot about how it will change the film industry and the way Asians/Asian-Americans are represented. Not all that dissimilar to the discussion around Black Panther. A new narrative has been introduced to the collective unconsciousness. I hope it’s true. I hope it does all it promises and more. But we won’t know for a while; 5, 10 maybe even 20 years.
In this highly volatile and reactionary atmosphere, it can be really hard to think long-term and work on issue areas that are put on the back-burner in the public conversation. Yet the time to act and effect change is now.
What does your typical week look like?
Monday: I work through the weekend on private client work, so by the time Monday rolls around, I’m ready for a break. In general, Mondays are when I work toward “inbox zero” (that’s the goal, at least...ha!) and do donor outreach and press.
Tuesday: I spin/swim/yoga 3-4 times a week and today is one of those days. Ultimately, my inbox drives the agenda for the day—so it’s hours of e-mails and research. Plus, some evening networking at an event.
Wednesday: Since I work all weekend, my husband and I take one full day off during the week to play hooky. Today is that day, so we linger in bed for as long as we can. My husband spoils me with breakfast in bed every day, and today is no different. I spend the morning reading, mostly refugee-related literature or articles. The afternoon is when we venture out for something fun. On this day, it was a trip to the Central Park Zoo, followed by dinner and more reading to end the night. Can you tell I love to read? You should see all the packed bookshelves in our home, nevermind my Kindle!
Thursday: E-mails and conference calls dominate the day again, but I also have a standing check-in with our team. We do a general progress report and a review of what’s next. Another workout and checking in with our previous students on Facebook and Instagram. A bit of chatting with them to catch up and see how they are.
Friday: I carve out some time to write in the morning and start scheduling some coffees with friends for the next couple of weeks. E-mails and conference calls continue to dominate, but for far fewer hours than earlier in the week. Being an entrepreneur really is quite glamorous!
Saturday/Sunday: These two days are a combination of client work, writing, reading, and researching. I draft e-mails, but schedule them to go out on Mon/Tue. It’s a way to catch up/get a jump on the week and the multiple projects, Hello Future, and more, that are happening concurrently. I particularly love Sat/Sun as they are quieter inbox-wise. It gives me the chance to think through next steps and carve out significant time to work on the curriculum or grant applications or research for new funding opportunities and not simply be reactive to e-mail.
Favorite place you’ve ever been (and why)?
That’s a tough one. I’ve been to over 80 countries and each of them are special in their own way. Nepal, Colombia, Istanbul, Mongolia, Tibet and Pakistan stand out in my mind, all for different reasons. We remember a place for the story that took place, sometimes it is about the place, but other times it’s the company, the adventure or a single sublime moment.
Best advice anyone ever gave you?
Invest your money in marketing and not in equipment.
Favorite place to see art in NYC?
The city itself is a work of art.
If you could have lunch with any human, who would you choose?
Bill Gates or President Obama. I want to know how they would evaluate the work they’ve done to date, what is next now that they’ve had time and accomplishments in the rearview mirror, and what they hope their legacy will be. What they’ve learned.
If you had to choose a song as your walk-up song before big moments, what would it be?
Either something by Pearl Jam or Frank Turner.
Best way to chill out after a long week?
Snuggle with my husband and make him laugh. His laughter makes me laugh and the week just melts away.
