What is it about entrepreneurial success that’s so inspiring? Is it the entrepreneur’s determination, vision, and grit to persevere through tough times? Is it the ingenuity of noticing a market opportunity and acting on it? Is it the leap of faith into risky territory, betting on an idea against the odds?
Or is it knowing that the person didn’t start off as an entrepreneur? They had an idea, the drive to pursue it, and the entrepreneurial skills to make it a reality. Maybe their success means you can do it, too—with the right skills and mindset.
Whether you’re an entrepreneur searching for inspiration or someone with the beginnings of an innovative idea, here are three success stories from the tech startup world to learn from.
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1. Songe LaRon and Dave Salvant of Squire
Songe LaRon and Dave Salvant are no strangers to the barbershop experience. Both New York City natives, they remember going to barbershops nearly weekly since the age of six, watching the men in their lives get haircuts. After working in banking and law, they found themselves drawn to entrepreneurship, and the lack of change in the barbershop experience caught their attention.
“The process hasn’t changed since I was a little boy,” Salvant says in the online course Launching Tech Ventures. “You go to the barbershop, call or text your barber, sit down in the barbershop for hours waiting for your name to be called, and then have to pay with cash. And this is the same time where you can get rideshare from your phone. I was like, ‘Why hasn't this changed?’”
So began the building of Squire, a barbershop point-of-sales and management system. LaRon and Salvant’s initial idea was a customer-facing app for booking barber appointments—what LaRon calls “the Uber of barbers.”
“There's an opportunity here that everyone else is missing for whatever reason,” LaRon says in Launching Tech Ventures. “I personally think there were some blind spots that investors and entrepreneurs had with this area and didn't see the potential. But we saw it, so we figured we had an advantage relative to everybody else because we knew this industry so well, so intimately.”
Eager to validate their hunch, the pair went door to door gathering feedback from barbers—or trying to, anyway. Most didn’t look at the product closely or have time to stop working to chat in depth.
Related: How to Conduct Market Research for a Startup
While at a WeWork, LaRon and Salvant encountered a group of executives and pitched their idea for Squire. One executive took a chance on them and provided seed funding, which they used to hire a developer and build the app’s first iteration.
To spread the word about Squire and get immediate feedback, LaRon and Salvant set up a pop-up barbershop in their WeWork space. They discovered it effectively solved the issues they’d experienced as customers: scheduling and payment. The problem was that the app didn’t address barbers’ needs.
In 2016, LaRon and Salvant purchased a barbershop to learn how to adapt their product firsthand. Salvant calls this a “bet-the-company” move because they used over half their funds.
The risk paid off. They learned the intimate challenges of running a barbershop—from managing bookings to paying individual barbers.
“They decided to pivot from targeting end consumers, a model known as B2C, to targeting barbershop owners, a model known as B2B,” says Harvard Business School Senior Lecturer Jeffrey Bussgang, who teaches Launching Tech Ventures, “focusing on the owners as the primary customer and building a software as a service, or SaaS, platform to meet their needs. While their initial focus on end consumers might be considered a failure, it proved to be an important lesson for their customer value proposition.”
The new platform took off. Squire is now available in three countries and has raised $165 million in funding, driving home the message that taking the time to understand your customers pays off.
2. Leah Busque Solivan of TaskRabbit
Late one night in 2008, Leah Busque Solivan ran out of food for her yellow lab, Kobe. Little did she know that would plant the seed for what would become her $50 million company, TaskRabbit.
“When I realized I was out of dog food that night, I immediately thought, ‘There's got to be a way to use my phone to pinpoint someone at the grocery store and connect with them and have them grab dog food for me, and I'm willing to pay them to do it,’” Busque Solivan says in an ABC News interview. “And that was the moment where I realized I could get really passionate about this idea. I know that I can build it, and it's something that I felt could help people all over the world.”
The idea blossomed into a website called RunMyErrand, which had 100 “runners” to complete errands for users in Boston, Massachusetts.
At the time, the “sharing economy”—an umbrella term for business models that facilitate peer-to-peer exchange of goods or services—wasn’t yet popular. Ride-hailing app Uber and home-sharing app AirBnB were mere ideas, and delivery service DoorDash wouldn’t be founded for another five years.
Car-sharing company Zipcar was one of the first major players in the yet-to-be-named economy in the Boston area. When Busque Solivan’s friend connected her to its CEO, Scott Griffith, he liked her idea and offered support in the form of workspace and guidance.
One piece of advice he shared was to apply for Facebook’s startup incubator, fbFund. Busque Solivan took the chance and was accepted, and she moved to the West Coast to grow her business.
During her time in the incubator, Busque Solivan raised $1.8 million in seed funding and met entrepreneur and author Tim Ferriss, who became a valued mentor and advisor. Ferriss also introduced her to her first investor, Ann Miura-Ko of Floodgate Venture Capital.
Related: Startup Incubator vs. Accelerator: Which Is Right for You?
The next several years marked a period of extreme growth. Busque Solivan changed RunMyErrand to TaskRabbit. A year later, she closed a $5 million Series A funding round. The company grew from 100 “runners” in one city to 2,000 “taskers” in five.
After closing a $17.8 million Series B round, Busque Solivan faced a new challenge: Apple’s App Store launch. She hired a developer and created an app version of TaskRabbit’s previously web-exclusive service.
To test the app, Busque Solivan launched it in London—an entirely new market—before TaskRabbit’s existing U.S. market.
“This was very controversial,” Busque Solivan says in an interview with the Computer History Museum. “I’m so glad we did it, in hindsight, because the product in London worked great. When we decided to transition it back to the U.S.—millions of customers and 50,000 taskers—it was a complete disaster.”
Pivoting from a web platform to mobile-first app upset and confused TaskRabbit’s U.S. customer base, but Busque Solivan leaned on the app’s successful London launch to justify pushing through. The company retrained taskers on the user interface, gained new customers and taskers, and recovered from the initial drop in customer satisfaction.
TaskRabbit has since expanded to nine countries and more than 75 cities. It was acquired by furniture provider IKEA in September 2017 and began offering furniture assembly in addition to its original services. Busque Solivan is now a venture capitalist at Fuel Capital, dedicated to uplifting other industry-disrupting entrepreneurs like Griffith, Ferriss, and Miura-Ko did for her.
Related: How to Find Product-Market Fit in the Tech Industry
3. Tanya Menendez of Maker’s Row and Snowball Wealth
Growing up, Tanya Menendez’s parents told her that her past didn’t define her future—and she took that to heart.
As a first-generation college student and daughter of immigrants, Menendez became aware of structural and economic inequality early on, leading her to study economic sociology in college.
After exploring law, policy research, and roles at Google and Goldman Sachs, Menendez decided entrepreneurship was her way to make a change post-graduation.
“I knew that I wanted to make a positive impact on society,” Menendez says in the interactive online experience Pathways to Business. “I knew I wanted to make it easier for people who came from any socioeconomic background to be able to have upward economic mobility. Business really attracted me because I could come up with ideas and make them a reality.”
Menendez’s first foray into entrepreneurship was when a friend asked her to join his leather goods company, Brooklyn Bakery. After working there for a year and a half, she noticed it was difficult to find U.S. factories to make leather goods.
To solve that problem, Menendez created Maker’s Row, an online platform that connects U.S. factories with designers and business owners who need American-made products.
As the company’s co-founder and COO, Menendez wore many hats and immersed herself in the fast-paced life of a tech entrepreneur. The experience also led her to start her second business in 2019: Snowball Wealth, a mobile-first platform that provides community and tools to help pay down debt and build generational wealth.
“I started Snowball because of a problem I experienced personally,” Menendez says in Pathways to Business. “I had student loans. I noticed that it was especially complex because of all of the different payment plans and federal forgiveness programs on top of policy changes. It was just incredibly confusing and overwhelming. No one really tells you how to pay down your debt. I saw that as an opportunity to make it much easier for people to understand what their options are.”
To date, Snowball Wealth has raised over $1 million in funding and continues to support users in their wealth-building journeys.
If you’re interested in learning from Black, Latinx, and underrepresented minority (URM) founders and business professionals about their journeys, explore HBS Online’s free interactive experience, Pathways to Business.
The Power of Learning from Real-World Examples
These startup success stories shed light on the importance of building a strong network, knowing when to pivot, and using personal experiences to identify opportunities.
Whether on the edge of entrepreneurship or in the thick of it, learning from real-world examples can be invaluable and provide insights that inform your trajectory.
If you’re interested in examining the ups and downs of other tech founders’ journeys, explore Launching Tech Ventures, which prompts you to consider what you’d do in real-world business scenarios. Through a combination of video content and interactive exercises, industry experts—including LaRon and Salvant of Squire—guide you through their thought processes, which risks paid off, and what they’d do differently if given the chance.
Entrepreneurship can be challenging, but with other founders to learn from, your startup can be another success story.
Are you ready to launch a successful startup? Explore Launching Tech Ventures—one of our online entrepreneurship and innovation courses—and download our free guide to starting your entrepreneurial journey.
