Qualities of successful entrepreneurs

byJeremy CaplanAug 26, 2019 in Media Sustainability

Stellar journalists have a lot in common with outstanding entrepreneurs. Both spin information into stories to inform and persuade audiences. Both work unpredictable hours and spend months chasing ideas that may not work out. And both rely on sharp questions to get the information they need. Here are some other qualities that tend to characterize successful entrepreneurs.    

Tolerance for uncertainty 

You may not be able to draw a salary in the early days of developing a new venture. People might ridicule your idea. Some may try to persuade you that it won’t work. (They might be right). To be successful as an entrepreneur you have to persist through the difficult initial period of uncertainty, when it’s far from clear that you’re creating something that’s valuable. You have to have thick skin to handle all the rejections you will face when putting your product out into the world. 

The question is not whether there will be a period of uncertainty. There will be. And there will be doubters. The question is whether you can tolerate ambiguity and still manage to sleep well at night. Having a nest egg for financial security may help. Even if you don’t have that, supportive family members and friends can be a huge help in weathering the early uncertainty. 


As an entrepreneur, you have to bring talented people on board even before you have a big audience or substantial revenue. Entrepreneurs need help with product development, design, marketing, sales and much more. To convince smart, capable people to buy into your vision, you have to be able to excite them about what you’re doing. That takes charisma. 

When people join a startup team, they do so because they believe in the founder. The startups that attract the strongest support often have a captivating founder. In the journalism realm, founders like Jonah Peretti of Buzzfeed, Jessica Lessin of The Information, Nate Silver of FiveThirtyEight, Carly Zakin and Danielle Weisberg of The Skimm, Jim VandeHei of Politico and Axios, and Rafat Ali of Skift all exhibited charisma in building strong teams even before they had full clarity on the viability of their ventures. 

Empathy and strong listening skills

Being able to understand the needs of your customers and partners is a huge part of being able to develop a successful venture. If you have empathy for the people you’re serving, you’re well-positioned to create something that will hit a nerve, rather than something that just interests you.  

Willingness to ask for money 

Journalists don’t often have to ask for money. We do persuade colleagues of the value of our story ideas, so sales is not entirely foreign to us. We pitch ideas, so we’re used to packaging key ideas and evidence into short presentations, as entrepreneurs often do. But as a startup founder, you have to go further. You have to explain why an investor or funder or client or advertiser should pay you for the value you’re creating. You have to get comfortable not just talking about money, but asking for it. 

Willingness to make mistakes

When you’re publishing an article, you work hard to avoid mistakes. You check every fact. You comb through each sentence looking for errors. But in entrepreneurship, mistakes are inevitable. Some of what you create to put in the market won’t turn out to have the characteristics customers need, because you won’t be able to predict those needs until you see how they use the product. 

In journalism we’re generally looking backward and trying to create an accurate record of what has already happened. Successful entrepreneurs, though, are trying to look forward and anticipate what people will need in the future. That means some mistakes are unavoidable. The successful entrepreneurs are the ones who make a lot of informed guesses and then learn and adapt to how people behave with their imperfect early product. 


Great entrepreneurs know they can’t do everything themselves. So they learn from others and they ask for help. Being able to distinguish between what you can do yourself and what you need others’ help with is crucial.   

Jeremy Caplan is Director of Teaching and Learning at CUNY's Newmark Graduate School of Journalism in NYC. Visit Journalism2030.com for a free collection of his entrepreneurial journalism resources. Follow Jeremy on Twitter @jeremycaplan or at jeremycaplan.com.

Main image CC-licensed by Unsplash via Adam Muise.