8 Characteristics Every Entrepreneur Needs
When she was a child, Lori Most hopped on jet skis and rode her bike to extremes. One journey through a patch of sand resulted in a universe of scratches on Most’s face. “I walked home dripping blood all over the place,” said Most, founder of Backpack EMR, which provides software solutions for medical clinics in remote locations. Most also played rugby, a sport not known for its gentleness, for 15 years.
“I definitely jump into things with both feet, not knowing necessarily what the outcome will be, but just hoping things will just turn out,” said Most, who’s based in Minneapolis. In 2016, she quit her day job to launch BackpackEMR, figuring she’d learn what she didn’t know along the way. “I just said, ‘I’m going to do this thing,’” she said.
What characteristics are in an entrepreneur’s toolbox?
- A high tolerance for risk, especially during low points
- A love of learning all types of things
- An obsession with excellence — and the self awareness to control it
- Adaptability when ideas need adjusting
- Optimism even in the face of setbacks
- Great mentors
- The ability to collaborate and say “yes and” to teammates
- Grit and the resilience to snap back from failures
A high risk tolerance helped her take that first step, as well as persevere through maxing out credit cards, being broke, borrowing money from her parents and other low points. “But I just kept thinking it would be fine in the end, and that we should keep moving forward,” Most said. The tolerance for risk “let me teeter on the edge for a while.” The flip side of that coin is that risk tolerance can be, well, risky. “I worry a little that I will be too tolerant of debt,” she said. “That might hurt us on the financial side.”
Entrepreneurs have fresh ideas and can tap a market for those ideas. Yet there’s much more to entrepreneurship. Like Most, entrepreneurs can handle more risk than the average person. They persevere through hardships, tap the talent of others to thrive and demand high performance from colleagues. Here, five tech entrepreneurs reveal the traits that have helped them succeed.
A Love of Learning
Most also said that a love of learning has helped her succeed as an entrepreneur. “It’s constant learning” to develop Backpack EMR for the different locations and medical specialties using the product, she said. “I need to be excited about learning to understand how to build a product for those different regions,” she said.
Most had multiple majors in school, starting off in aerospace engineering, switching to premed, and then landing on physiology and math, earning degrees in both disciplines. She also earned a master’s degree to teach math, then went to bootcamp to learn how to code. “I kept wanting to learn more things,” Most said. “That’s been really helpful with the entrepreneur piece, because you’re constantly having to learn in lots of different areas in order to stay ahead.”
As an entrepreneur, she’s taught herself about accounting, financials, the world of investors, capitalization “and all this stuff on the product side and sales,” she said. “It’s so many things that I’ve never had to know before.”
An Obsession With Excellence
When Anne Cheng would score 98 on a high-school math test, she’d beat herself up for not reading the missed questions more carefully or reviewing her work. Cheng’s longtime obsession with excellence “helped me build my business from basically nothing to a little bit of something,” she said.
That business is Delaware-incorporated Supercharge Lab, which makes software that automates and optimizes sales and marketing functions for companies. The company has 13 employees, 110 clients, $80 million in gross revenue, and is in the process of raising its first fund. “Excellence cascades through everything we do,” Cheng said. The concept is written in the mission and vision statement, ensconced in core values, and discussed frequently at team meetings.
Chasing excellence — perfection, even — helps Cheng and her team attract and keep clients who can expect a certain level of quality from the company. It also enables her to turn down clients who aren’t a good fit, and who could potentially cost the company money in the form of wasted time. “I do get impatient with clients who expect the world but refuse to accept the guidance we offer,” Cheng said.
Cheng began her career in financial services, exiting after the financial crisis of 2008 and 2009 and eventually starting an angel investing fund. Noticing that a lot of the startups didn’t understand operational efficiencies and organizational infrastructure, she launched into consulting for Fortune 500 companies. Surprise: “They had significant inefficiencies, too,” Cheng said, and that led her to found Supercharge Lab.
Being a perfectionist has drawbacks, one of which can be an occasional impatience with people. “I expect so much out of both myself and the people around me,” she said. Realizing that, Cheng created a structure in which only the CFO and chief of staff report to her, with everyone else reporting to the chief of staff. With this structure, Cheng doesn’t have to manage people and she can focus on the business of growing the company.
Adaptability and Optimism
“You have to be very optimistic to start anything new, and you have to constantly adapt your internal model of things to identify new opportunities that are worth pursuing,” said Mike Dickey, founder of three successful startups, most recently Palo Alto, California-based JackTrip Labs, an open-source software app that enables musicians to play live together over the internet.
Dickey, co-founder and CEO of JackTrip, taught himself how to code in high school and dropped out of Carnegie Mellon University to pursue entrepreneurship full time. Despite early success, he didn’t recognize these as traits until later in his career. “It could be that it took time and experience for me to develop them, or just more interactions to recognize how I seemed to be different from others,” he said.
The optimism fuels creativity and innovation — he’s always open to trying new things — and that allows him to move forward with ideas. For instance, as soon as he understood that the physics involved with JackTrip would work, he believed wholeheartedly that he could solve the delay and quality problems with live performances over the internet. As for adaptability, “things are changing all the time, especially in technology,” Dickey said.
He credits his adaptability for recognizing that two major changes would fuel JackTrip. One is the massive improvements in home internet connectivity, and the other is massive improvements in digital signal processing. “It takes a lot of adaptability to fully appreciate how disruptive these changes will likely be,” he said.
The one drawback to optimism? “It can start out as being irrational and therefore be a blind spot,” he said. “It’s important to look and aim for validation points and iterate quickly when you discover that you were wrong.”
As a kid, Scott Silberstein was big on teams. “I was always trying to get a band together, and put people together,” said Silberstein, co-founder and executive producer at Chicago-based HMS Media, a tech-driven production company that creates broadcast and digital content for Broadway, national tours, and Chicago dance, theater and music companies.
Silberstein and his cofounder, Matt Hoffman, met when they were teens at Camp Nebagamon in northern Wisconsin. Trained musicians, they formed a band, wrote for Camp Follies, Nebagamon’s annual musical, and planned to make a living as a songwriting trio. They dreamed of being the next Kander and Ebb — the songwriting team of John Kander and Fred Ebb, who wrote “Cabaret,” “Chicago,” and “New York New York,” made famous by Frank Sinatra. Silberstein and Hoffman founded HMS in 1988, right after graduation, and Kander mentored them along the way.
Through a connection at the camp, Silberstein and Hoffman met Kander. “That was my first professional mentorship,” Silberstein said. One memorable lesson came when the two were working on shows, separately. Kander, the acclaimed songwriter, confessed to being “scared to death” about going into rehearsals, explaining that he was convinced that on the next show, the world would figure out that Kander really didn’t know what he was doing.
The lesson for Silberstein: “Not knowing what I’m doing” doesn’t mean “I’ll never get it done.” Instead, “it describes that vulnerable moment when you’ve come up with an idea and gathered the people you think you need to make that idea come true, without actually knowing how it’s going to get done,” he said. Silberstein regularly talks to Kander, who’s 94 and still active in the world of musical theater.
A ‘Yes and’ Attitude
Silberstein’s time in musical theater — he is an artistic associate at Lookingglass Theatre Company in Chicago — also taught him the power of “yes and,” the guiding principle of improvisation. “To make great things happen, you can’t say no, and it’s not enough to say yes,’ Silberstein said. “You have to say ‘yes and’ so you can contribute.” The phrase gets the best ideas in the room on the table and gives everyone the chance to make the idea better. Egos are set aside, “and you’re always in service to the idea,” he said.
The team realized the power of “yes and” during the pandemic, which challenged HMS to use every piece of video technology it had to help companies livestream performances for home audiences. When the country shut down, they worked with Broadway, TV and film stars to create benefit fundraisers and an original murder mystery musical that the actors shot by themselves at home.
Soon after, HMS developed new approaches to camera and editing technology to create original shows for streaming audiences, including concerts, plays and gala performances for Lyric Opera of Chicago, Chicago Shakespeare Theatre, Goodman Theatre and Lookingglass.
Grit and Resilience
Shariq Siddiqui, CEO and co-founder of contactless grocery shopping app Veeve, thrives on risk. “I have a fear of complacency, which drives me to take on that risk and seek innovative solutions for customers,” said Shariq, who is based in Seattle. Handling risk requires “an enormous amount of grit and conviction that you are up to the task,” he said. “The combination of grit and resilience is key for success as an entrepreneur.”
Veeve isn’t his first startup. In middle school, Siddiqui sold custom-printed T-shirts to friends, and in college, started a subscription-based barbershop in his dorm room. After college, he built a hyper-local wayfinding app, NYCWay, funded by then-Mayor Michael Bloomberg. The app, which was acquired by BMW Interactive, boasted two million users. “While these experiences are different from Veeve in terms of size and scope, there are still lessons and learnings that I carry with me to this day on building something from scratch, promoting my ideas, and persevering through obstacles to drive results,” he said.
He also gained a few insights during his decade at Amazon. Exposure to Jeff Bezos’ Regret Minimization Framework played a key role in his decision to launch Veeve. “Using this mental model helped me realize that when I was older I would regret not embarking on this path,” he said. He also realized that Amazon was a gathering of bright minds tasked with disrupting existing businesses, not just a giant corporation. “Once you understand that, you start using competitors’ massive size to your advantage by moving faster as a smaller, more nimble company who can aspire to be as big as they are,” he said.
Even the grittiest, most resilient entrepreneur, however, will face setbacks. “Embrace failure,” he said. “Your grit and energy are finite, so make sure you use them in the right places.”