12 Questions Entrepreneurs Wish They Would Be Asked

September 28, 2016

As everyone in the startup world knows, there’s no shortage of questions surrounding your day-to-day activities: How much funding are you looking to raise next round? What are your relationships like with your investors? What’s your staff size? What platforms are you using for marketing (with no budget)? What does your target customer look like? And the list goes on.


As an entrepreneur and the founder of Scribendi.com, an award-winning online editing and proofreading company with clients around the world, I’ve had my fair share of over-asked questions thrown at me. I started to think that there had to be other, more interesting questions entrepreneurs were hoping to be asked.


So I reached out to 13 entrepreneurs who had launched their products on Product Hunt within the past couple of months and that made it to the front page. These successful entrepreneurs all had questions they were dying to be asked. Maybe these will spark some great conversations the next time you’re in a room full of entrepreneurs!


1. “Why are you working on your startup?”


“I think a lot of times we get so caught up in what we’re doing—building product, talking to customers, meeting with candidates and investors—that we don’t often step back to think about why we’re doing it. Startups are amazing because they allow people to create something out of nothing, have a tangible impact on others, and have control over their own destinies. I wish people asked me about the why more and the what less, since it really helps you recenter and feel grateful to be doing what you’re doing.”


Jack Altman, Co-Founder and CEO of Lattice – “Lattice weaves goals into your workflow.”


2. “How would you go about starting a company with $ 500?”


“I’d love to get asked this question because too many people think that you need to raise money to start a company. It’s getting cheaper and cheaper to start a company, and I don’t think aspiring entrepreneurs should even think about fundraising until they absolutely need it (if ever). This is especially true for entrepreneurs that don’t have a previous success under their belt.”


Christopher Gimmer, Co-Founder and CEO of Snappa.io – “The easiest graphic design tool you’ll ever use.”


3. “What are your hobbies outside of work?”


“When I’m busy, I sometimes tend to neglect personal hobbies, so it’s very refreshing to switch gears and talk about something else I enjoy. Plus, if we share a hobby, it’s a great way to start a conversation!”


Lenny Hu, Designer and Product Guy of YesInsights – “Get customer feedback with simple one-click surveys.”


4. “If you had to change roles within your own company to something other than being the CEO, what would it be?”


“As the CEO of an early-stage startup, I wear a lot of hats. There are obviously some that I like more than others, and even some that I wish I could wear due to personal interest but can’t because of bandwidth or lack of skill set (i.e., some technical CEOs might wish they could spend more time learning how to do marketing vs. some non-technical CEOs might wish they could learn how to code). I think this would be a great question to be asked so people can find out more about me and the areas of expertise I bring to the company.”


Diego Villarreal, CEO and Co-Founder of Banter! – “Waze for nightlife.”


5. “How do you learn to become a co-founder?”


“I’m fascinated by the level of emotional intelligence that successful entrepreneurs are required to have. Thirty-three percent of all startups fail because of founder conflict, which makes me surprised at how little attention is given to how to develop a healthy and successful relationship with your co-founders. These are people you are likely going to see more than your SO during the early days. With my co-founders, Sam and Lianne, developing a successful way of agreeing, disagreeing, and growing together wasn’t easy—we had plenty of rough patches—but the level of candor and care we operate with today is probably what I am most proud of as a founder.”


Devon Tivona, CEO and Founder of Pana – “An on-demand travel concierge.”


6. “What change would you like to affect in the world?”


“I would love to be asked this question because I think it is incredibly important for all founders to be thinking about this as they launch their next venture. Creating change is powerful and invaluable for our society to continue growing and pushing the envelope of innovation. I also think the answer to this question gives a raw insight into who the person is and shows the true passion behind what they are doing and what they want to accomplish in their lifetime.”


Diego Saez-Gil, CEO and Co-Founder of BlueSmart – “The world’s first smart, connected carry-on.”


7. “What Game of Thrones house do you see your company being part of: the Lannisters, Targaryens, or Starks?”


“Definitely House Stark! I’m a fighter and will always get back on my feet after I’m knocked down. Plus, I always tell the rest of the team that ‘Winter is coming.’ But that’s just because I’m a total snowboarding geek and get super excited when winter comes!”


Christoph Wagner, CEO of Unfade – “Scan your old printed photos and bring them back to life!”


8. “What opportunities does your startup have to affect positive social change?”


“I would want to be asked that because I think all entrepreneurs should consider it and have a good answer to it. We live in an amazing time when issues of social and economic justice occupy all levels of discourse. Entrepreneurs are uniquely poised to embrace new ways of doing business, new markets and new participants in the market, and new ways of relating to society at large. This fact is always front of mind for us at Winnie because children quite literally are the future. We have to go above and beyond building products for moms of a certain income level. Child rearing isn’t just a mom problem; it’s a social responsibility we all share.”


Anne Halsall, Co-Founder of Winnie – “The inside scoop on great activities and destinations for families.”


9. “Why are you passionate about this project?”


“I feel like, especially when it comes to tech startups, many founders start companies because they see a market gap, or because a VC told them about an idea, or something like that. When I meet founders, I’m always most concerned about why they care about something, intimately, personally. You can often learn a lot more about a person by asking about their passions than asking about their market research.


“Lacona has been a huge passion project for me—a need that I felt over 10 years ago, which still hasn’t been met all those years. It’s just a nerdy NLP app at its core, but talking with people who get pumped about this sort of thing is incredibly fun.”


Brandon Horst, Founder of Lacona – “Control your Mac using natural language.”


10. “What’s your favorite cartoon character?”


“Snoopy! My dad used to bring me books from his trips to the U.S. when I was a child. Also, here’s an obligatory ChalkMotion-style drawing for your viewing pleasure:”


12 Questions Entrepreneurs Wish They Would Be Asked


Adi Ben-Hur, Creator of ChalkMotion – “An online service designed to help visualize and share ideas with animated doodles.”


11. “How come your second Kickstarter campaign was so much more successful, even though it was for almost the same product?”


“I love this question, because unlike the generic “How’s your business going?”, it gives me a chance to tell you about all the things that I’ve learned from doing two Kickstarter campaigns. When I launched my first campaign back in 2013, I was sailing blindly. Seemingly benign decisions like the length and goal of the campaign cost me a lot of backers. I also spent a lot of my time and energy on tasks that had poor ROIs. So after making improvements to the Pocket Tripod, I returned to Kickstarter, but this time with a lot more experience on what works and what doesn’t.”


Rambod Radmard, Creator of Pocket Tripod – “A card-sized phone tripod that adjusts to any angle on demand.”


12. “Are you open to the possibility of us acquiring your app for $ 1 billion?”


“My answer would likely be yes. Please ask me this.”


Lucas Gordon, Creator/UI Engineer of Babel – “Import your Spotify playlists to Apple Music.”

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Author: Chandra Clarke


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