10 women, 10 different paths to starting a business

Kt McBratney
OwnTrail Blog
Published in
4 min readSep 1, 2020
Lizzy, Shalini and Naimeesha all started companies, but it’s clear their journeys look very different.

Women are answering the call of entrepreneurship — in the U.S., women started an average of 1,817 businesses per day in 2019. But what does that look like, really, to a woman aspiring to found a company? Current research like this is helpful in proving that she’s not alone in pursuing this goal, but it doesn’t tell her anything about the how or the why of the women entrepreneurs that have come before her. Fortunately, they’re sharing their journeys on OwnTrail as micro acts of mentorship. Here’s a glimpse at 10 of these stories:

Lizzy Karp

Our purpose can guide us on our paths, like Lizzy’s commitment to support storytellers and connect communities through storytelling. In 2013, that led her to co-found Here There, a studio producing experiences for the community and brands while creating gigs for creative folks in film, food, art, dance and more. Two years later, she transitioned out of the company to a role at Storyhive that she says “truly changed her life”.

Shalini Tripathi

Sometimes the path to founding an organization comes from personal history. After a particularly memorable night of triggering memories of bullying and racism, Shalini made the decision to do everything she could to help any young womxn in need of a guiding light. That’s when Embrace Her Lead was born — a non-profit that connects ambitious young womxn with peers and mentors passionate about empowerment through empathy and experience.

Naimeesha Murthy

Naimeesha’s journey includes starting two companies — so far! During and despite the pandemic, she’s grown Products By Women (a diverse community for women in innovation and tech) from a New York focus to a global community spanning the U.S., India, Singapore, the UK and the Netherlands. We love how transparent she is about the fact that some times ventures don’t work out and that it’s okay to move on to focus on something new!

Vix Reitano

There’s plenty of buzz about side hustles, but Vix’s story is the real deal — after working with brands including AOL and Time, Inc, she built her own company — 6boro Social + Studios — to six figures in just six weeks. As founder and CEO of this creative digital agency, she then grew 10x during the pandemic and continues to pay it forward by hosting #CocktailsAndConversations to help small businesses and marketers navigate the twists and turns of their businesses.

Anatasia Ellis-Tarpeh

Your starting point does not define where you might go. Need proof? Check out Anastasia’s trail, where 2 years of undergrad studies in mechanical engineering led to a change of schools and majors, graduating with a degree in international affairs, Arabic language + culture and then a masters in public policy. But it was after she left her job in special projects due to the COVID-19 economic downturn that she put herself in the founder seat as the co-founder of Bosa, a wellness and productivity app simplifying tasks for busy professionals.

Courtney Blodgett

If you expect the road to founding Yield Positive, a company to help people learn about sustainable investing to have a direct path, you need to see Courtney’s trail. From multiple international moves, experiencing misogyny at work, overcoming a layoff with a hike to Everest Base Camp sans guide, her journey is one of perseverance, opportunity and purposeful pivots.

Miracle Olatunji

Starting a company doesn’t have to come after graduating from college or even high school. Miracle founded OpportuniME while in high school to empower the next generation of leaders to realize and reach their full potential. From this founder milestone, she’s become a paid public speaker, moved to Boston and received an Extraordinary Woman Award.

Amanda Munday

Part of starting a company is deciding to take the plunge, and part is figuring out how to fund it. Amanda left a career leading marketing at a growing startup to open the Workaround, a 13,000 square foot coworking and childcare space in Toronto, on her by bootstrapping the business and debt financing. That’s a total trailblazer move.

Ashley Connell

Ashley built a career in marketing for software and hardware companies before founding her second company in a wholly different space — using tech to help employers find expert talent by vetting and certifying women who want flexible, empowering work. It’s been a powerful pivot, as she’s taken Prowess to profitability in its first year.

Kayla Kuboyama

Can you start a company after taking time off for family? What about if a few of your previous ideas didn’t take off? Or if you’re a first-generation college grad? Absolutely. Take a look at the trail Kayla is blazing as the founder of Price of Paradise 808, a company promoting Native Hawaiian excellence by engaging tourists, businesses and settlers of Hawai’i in reparative, decolonial relationship building.



Kt McBratney
OwnTrail Blog

co-founder & chief brand officer @OwnTrail. aspiring jungle cruise skipper. @k_to_the_t.