Updated in October 2024
One of the most commonly touted “selling points” of entrepreneurship is the ability to be your own boss. While many individuals do become entrepreneurs for this reason, it’s not always necessarily their motivation: People start their own businesses for a variety of complex reasons, and sometimes it’s a surprising, unexpected event that drives them to take the leap into startup life. Sixteen successful entrepreneurs told Business News Daily about the unique experiences that inspired them to start their businesses, and the most important lessons they learned along the way.
A lack of mentorship and support resources
Katelyn Bourgoin, founder of Vendeve, a network for female entrepreneurs
“I created Vendeve because it was the community I wish had existed when I started my freelance business five years earlier. I learned pretty quickly that starting a business was the easy part. Scaling that business is downright hard. I needed help, but I didn’t know where to get it. I started Vendeve so that women entrepreneurs could support each other in the journey. They’re network-driven [and] collaborative, and they ‘sell’ by helping each other. They needed a business network that worked the way they do.”
Katelyn’s lesson: “Surviving the first few years [of a startup] requires enormous sacrifice and a sort of obsessive drive to keep growing. You need to wake up each morning and ask yourself, ‘How can I be better today than I was yesterday?’ You need to push yourself beyond your comfort zone on a daily basis.”
Falling in love with the startup scene
Renée Warren, co-founder and CEO of Onboardly
“In 2006, I got an opportunity to manage one of Toronto’s co-working office spaces, where I was exposed to the tiny startup community that existed at the time. I housed a couple startups and some other organizations there and held relevant events. It grew, and so did my network. About nine months later, I was consulting startups on their social media and marketing strategies, which eventually turned into a full-time gig. I sold that company in 2011 and have been growing Onboardly ever since.”
Renée’s lesson: “Always be learning. The most successful businesses are led by those that are consistently expanding their mindset, beliefs, experiences and knowledge.”
Fulfilling his American dream
Joseph Ram, CEO and founder of wireless solutions provider InfoSonics and verykool
“As an immigrant, I [dreamed] of moving to the U.S. and starting my own business. In 1989, I left a very stable business in Israel and was able to use my knowledge of the [telecommunications] industry to [pursue] my own dream. In every job I ever had before moving to the U.S., I strived to understand each department’s function to the core. To master the knowledge, responsibilities and functionality of each major department provided me the foundation to start my own business and grow successfully.”
Joseph’s lesson: “You need guts, but you can’t always just act on them. You need evidence to back it up. You need to use your resources, as many as you can, to get validation.”
A toxic corporate environment
Shannon Miles, COO and co-founder of virtual assistant service eaHELP.com
“For the first time in my decade-long career at a Fortune 15 company, my client was out to get me. I had been working with this particular client for over five years. They had a change in leadership, and the new person in charge made it her personal mission to beat up every vendor that didn’t do what she wanted. I knew I needed to make a change out of that toxic environment. I began looking for other opportunities, [but] none panned out. It was at this crossroads that intersected with my husband’s desire to leave his job and pursue our business. We decided to join forces and quit our jobs on the same day, which was the start of our lifelong dream of being business owners.”
Shannon’s lesson: “Try not to do everything on your own. Asking for help and outsourcing various business functions enables [you] to go further.”
The search for a greater balance
Chantal “Taly” Russell, CEO and founder of senior recruitment agency SilverChair Partners
“I had been working basically 24/7, right through having two babies, never missing a single day of work. I realized that there had to be a better way. I was so mired in the ‘hamster wheel’ that I had stopped growing and creating. I wanted a more balanced life for my colleagues and myself that would support personal, ongoing life changes, and a working culture that welcomes and acknowledges each individual’s professional and personal needs.”
Taly’s lesson: “Put down the mobile phone, step away from the computer. Close your eyes and just breathe. Many of my favorite epiphanies have come when I had cleared my mind, even if only for 10 precious daytime minutes.”
The love of (wo)man’s best friend
Kristina Guerrero, CEO and founder of TurboPUP, a provider of on-the-go dog meals
“I was at the top of a mountain, miles away from my car, with my very hungry rescue dog, Dunkan, and no dog food. All I had in my pack was a burrito and a power bar. He ate the burrito, [and] I thought, ‘Why don’t they have portable meals like this for dogs?’ I went home and tried to find one, but couldn’t. That’s when I came up with TurboPUP. I never know when I’m going to be out longer than planned, and it’s not fair to let my dogs go hungry.”
Kristina’s lesson: “A majority of entrepreneurs have emotional attachments to their companies and products. Don’t let your pride get in the way of progress.”
Layoff turned business opportunity
Nellie Torres, president and CEO of construction services firm ProjectSpan Services
“I was laid off from a contractor who decided not to pursue transit [infrastructure construction] work. I realized what specialized knowledge [I had], and that maybe I could leverage it into specialized business offerings. I didn’t want to be laid off on a whim anymore.”
Nellie’s lesson: “Sometimes ‘no,’ though the hardest answer, may be the best answer for your business.”
The complex, creative spirit of a festival
Lior Rachmany, CEO and founder of Dumbo Moving and Storage
“In the summer of 2006, I had the opportunity to attend the Burning Man festival. After having such a complex, edgy, positive and creative experience, I was inspired to approach the next steps in my life confidently and with that same creative, positive, edgy and complex attitude I experienced at the festival. That is what shaped the spirit of Dumbo Moving.”
Lior’s lesson: “The best way to build the perfect product is by not wasting time with perfectionism and by not losing momentum. You need to get the ball rolling.”
The desire to make a real difference
Kevin Sherman, founder of AquaBall flavored-water company
“I took a job as a teacher, [and] it did not take long to see firsthand the effects of childhood diabetes and obesity. The reality became evident that there were simply no healthy beverages for children on the market. All the beverages marketed for children were loaded with sugar, calories, artificial colors and flavors, and were contributing to childhood obesity and diabetes at an alarming rate. I made the decision to leave education and go back to the business world. I decided to formulate a zero-sugar, diabetic-safe beverage for children [using the sugar substitute] stevia.”
Kevin’s lesson: “Spend a lot of time on training the will [and] do not make decisions based on emotion. Once your will is strong, you become immune to the noise and ‘false audience’ we ourselves often create.”
A new insider perspective
Sarah Nahm, CEO and co-founder of applicant-tracking system Lever
“I spent six months with a team of recruiters [at] a well-known Silicon Valley tech company, understanding firsthand just how tough their lives could be. [My co-founders and I] shared in every pain point, and every win. Not only did we gain crucial insights that would be at the core of our product, we also took away a very human, very real picture of who we would be helping.”
Sarah’s lesson: “Since our very early days, we’ve made diversity a company priority. Many of Lever’s customers and job applicants are interested in learning more about us because of what we stand for, thus helping us sell our product more consultatively and attract new talent pools.”
Controlling his own destiny
James Ontra, co-founder and CEO of Shufflrr
“When I was a kid, my family had to file for bankruptcy, and for a period of time, we depended on the generosity of friends and other family members. I hated that feeling of being a victim, with no control over my situation. In my teens and 20s, I had several entrepreneurial successes, but I still felt that each endeavor was fleeting. It could all be gone in a minute. Twenty-five years later, after building several businesses along with my reputation, I have confidence knowing that my current company, Shufflrr, is built on a solid foundation. At times, we’ve been razor-thin on cash, but we’ve persevered. It caused me to understand that hard work and knowledge is the path to my success.”
James’s lesson: “Learn to understand yourself and what motivates you, then use your own motivation to motivate your team. The sincerity will show.”
A simple solution to a common fashion problem
Holly-Dale Shapiro, founder and designer of Go Go Golosh
“On my way to a formal wedding, I stepped into a slush puddle up to my ankle [and] ruined my expensive pair of party shoes. At the dinner table, I was complaining about my wet shoes, saying that someone should come up with a good-looking fashion overshoe that can be worn over dress shoes. [Another guest] said, ‘Why don’t you do something about it?’ That did it!”
Holly-Dale’s lesson: “‘No’ [often] means ‘not now.’ Always ask questions and find out why. It will only help your business so that you can get to ‘yes.’”
A simple surgery gone wrong
David Norris, CEO of MD Insider
“About 10 years ago, I had knee surgery that was supposed to be outpatient. Three days later, I found out I had a staph infection, and went back into the hospital for two weeks for surgery and serious treatment — I could have died from it. This led me to seriously consider how I had chosen my doctor and the treatment, and I noticed that there was no real data on physician performances. I created MD Insider to provide factual physician-performance data to help others avoid what I went through.”
David’s lesson: “Be much quicker to act when you know someone is not going to succeed [at the company], rather than to keep trying, [even] for the right reasons.”
Frustration with slow development speeds
Nancy Hua, CEO of mobile optimization solution Apptimize
“When I was working on my own apps, I was always impatient to figure out what was going to work. I could see that everything moved way too slowly, especially given how fast everything changes on mobile. I could see it would easily take years before we started to succeed, and I didn’t have that kind of time. The first version of Apptimize was a mobile framework we made to get around the barriers that slow down the whole process when you’re trying to build something in mobile.”
Nancy’s lesson: “Good business is about playing a long-term game. If your product is the best, then the customers will eventually figure it out.”
Democratizing educational opportunities with technology
Mark Yosowitz, president of Mentored.com
“As a college student, I tutored students at a school in a high-poverty area of West Philadelphia. The teacher was incredibly talented, but it was nearly impossible to provide individualized attention to her class of 25 students. Personalized instruction is the most effective way to learn, but has historically been too expensive for most families and schools to afford. Teacher-to-student ratios [in these areas] have not improved, but access to smartphones, tablets and laptops has dramatically increased, and technology has created new opportunities to improve educational outcomes for all students. This exciting new reality inspired us in our mission at Mentored.com to democratize access to quality tutoring for all students regardless of socioeconomic status.”
Mark’s lesson: “Focus on your vision, prioritize effectively and don’t get too distracted.”
Changing the mortgage problems that led to the recession
Jason van den Brand, CEO of mortgage borrowing solution Lenda
“The 2008 crash was the impetus to start Lenda. Having been in mortgage [during the time] leading up to the crisis, I learned firsthand that if modern technology existed to provide a radically transparent, educational, online experience, you could help consumers remove the moral hazard, high commissions and telemarketing [of] loan officers, and eliminate the slowness and error-prone compliance risk [of paper-based processes]. This ultimately leads to lower costs for consumers and lower risk for lenders.”
Jason’s lesson: “You can spend all the time and money in the world marketing and selling, but if you do that for a bad product, you’re wasting your time.”
