Female Founders Series Part 2: Leaping Into the Challenges and Rewards of Entrepreneurship

To foster the spirit of entrepreneurship and build connections among female entrepreneurs, Block Advisors recently partnered with Selfmade, a 10-week (virtual) business course offered through Brit+Co, helping female founders create and grow their businesses. Our sponsorship provided 200 scholarships for women to take the course at no cost. This is the second in a series telling the stories of select Block Advisors scholars.

Stephanie Smith is an online media rockstar who marches to the beat of her own drum. Her Atlanta-based consulting firm, Social by Steph (previously known as Digital Insomnia) specializes in paid social advertising, primarily for small and medium-sized businesses that don’t have “deep pockets.”

Stephanie began her career in 2010 with digital start-up BLiNQ Media, one of Facebook’s original preferred partners. There, she was deeply involved in media buying, developing media practices, growing the media team, and providing strategy to clients, while working with some of the digital industry’s top agencies and managing multi-million dollar accounts for national and global brands.

Working for a start-up early on planted the entrepreneurial seed, but several years of moving between unsatisfying jobs in the years that followed watered that seed and made it grow. She fell into (in her own words) “the millennial job hopper” trap, averaging two jobs per year for a while—always chasing something she couldn’t find anywhere else. Disenchanted by the chase, she decided to take her media campaign experience and set out on her own.

Taking the leap into entrepreneurship

Stephanie leapt into entrepreneurship with the creation of Digital Insomnia, which she since rebranded to Social by Steph.

“I created Social by Steph to help brands and entrepreneurs that may not want the traditional agency partnership or better yet, the agency fees,” said Stephanie. “With me, you get years of agency experience working with some of the world’s largest brands packaged up into a budget that your pockets can handle.”

Since then, Stephanie has worked with an impressive range of clients, including the Biden/Harris presidential campaign, Chick fil-A, and Facebook. She also earned top honors and a cash grant of $5,000 at the end of the (Block Advisors-funded) Selfmade course for her prototype of a digital ad simulator, SiMMY, that teaches users how to create and manage digital ads without spending real money.

No regrets, just money earned, lessons learned, and connections made

That isn’t to say it’s always been smooth sailing. After becoming a mother at a young age, giving birth after her third year at Georgia Tech, Stephanie was determined to show her son that setbacks don’t have to determine your future. She graduated on time and never looked back—working tirelessly ever since to achieve her goals. From buying her first home as a single mom to launching her own company, her son is her main source of motivation.

Launching SiMMY has also had its setbacks. For various reasons, her first developer didn’t work out, but instead of giving up on her vision, Stephanie soldiered on to create – and fund – a new development team to keep the project on track. In the true spirit of entrepreneurship, she is also self-funding SiMMY’s development by entering (and winning) as many pitch competitions as she can. Block Advisors’ scholarship and Selfmade’s grant were just one piece of the puzzle.

Along with hard work and determination, Stephanie credits networking for getting her to where she is today, and she relies on word-of-mouth recommendations from her entrepreneur friends when looking for business partners she can trust. This type of social capital is a key component of small business success, but often harder for female entrepreneurs to build and sustain than their male counterparts.

“My network has been so strong that I’ve never had to be in ‘sales’ mode with my business. That has allowed me the flexibility to work with and help other female and minority business owners,” said Stephanie.

Despite the ups and downs, she wouldn’t change a thing. “I look back and, while my friends and family will never understand my moves, every one of them helped shape what I’m doing today. No regrets, just money earned, lessons learned, and connections made,” said Stephanie.

Facing the unique challenges of female entrepreneurship

While entrepreneurship is challenging for everyone, the issues facing female entrepreneurs are often very different from those experienced by men, adding to the difficulty. From lack of funding, to loneliness and a lack of support, to fear of failure and low self-confidence, to balancing family and other personal responsibilities—the list is long. And for Black female entrepreneurs, these issues can be compounded by racial discrimination. 

Stephanie isn’t immune to these hardships, especially as a single mom trying to juggle the various new business opportunities coming her way, serving her current clients, and building new technology that she’s passionate about—all while being an active participant in her son’s busy life.

Being a woman of color has also impacted her business.

“I’ve had some doors opened for me because I was vouched for by a white man first, and it shouldn’t have to be like that.”

Still, she feels fortunate to have influential people in her corner who believe in her. And she intends to pay that forward.

Paying it forward with Black-owned businesses

“With the opportunities I get, I make sure to pay it forward by being influential for others when I can.”

Most recently, this included hosting a program for Black-owned businesses that were negatively and disproportionately affected by the pandemic.

“So many businesses had to focus on going digital just to survive, and I wanted to help them by sharing my knowledge about advertising on Facebook and Instagram.”

Stephanie’s observation is backed up by Block Advisors’ ongoing “Small Business Recovery Series” study about the effects of the pandemic on small business owners, which showed Black and Latinx business owners were more likely than their white counterparts (62% vs. 43%) to increase their digital/online presence to meet new needs, while also reporting more trouble doing so (46% vs. 26%).

Continuing to pay it forward, Stephanie shares another “lesson learned” with other entrepreneurs:

“It’s important to outsource when you can afford it. A lot of entrepreneurs want to hold onto every dollar that comes in and, consequently, handle every task of owning a small business. However, I’ve learned that I can make more money by focusing on what I’m good at and paying someone else to focus on what they’re good at.”

Connect with a Block Advisors tax pro today to learn how they can help your small business with taxes, bookkeeping, or payroll. Make an appointment now.