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Ryan Connolly, CEO,

YEC Member Spotlight: Ryan Connolly, CEO,



Ryan Connolly is working on, a tool for sharing mobile videos. Teams use as an operational tool for validation and troubleshooting, and externally with clients for sales, progress updates and customer service. Prior to, Ryan worked at the White House and received an MBA from Stanford. Cooking, reading and running have claims on Ryan’s free time, and Travis McGee is his favorite fiction hero. Follow him @dispatchtv.


Who is your hero?

Ernest Shackleton is up there. “Endurance” by Alfred Lansing is a book worth re-reading every few years. I love Shackleton’s original newspaper ad for the expedition, which hews to the experience of starting a new venture of any kind: “Men wanted for hazardous journey. Low wages, bitter cold, long hours of complete darkness. Safe return doubtful. Honour and recognition in event of success.”


What’s the single best piece of business advice that helped shape who you are as an entrepreneur today, and why?

“We spend so much time planning our hours and days that we forget to plan our months and years.” This is a piece of advice from one of my favorite professors. I have always taken it to mean that it’s never too early to start carving out the life you want for yourself. Each year you stay in a staff job in a larger organization, you diverge farther from the entrepreneurial path. And each year the perceived risks of making the jump increase. Lots of life events, from starting a family to buying a home, narrow your focus and it can be tough to even remember to make dedicated time for reflection and think about where you want to be in the future.


What’s the biggest mistake you ever made in your business, and what did you learn from it that others can learn from too?

Hiring poorly and keeping that person on the team longer than I should have. You hire someone and give them the support they need to successful. It can be difficult to remain objective about the results — either because they were your choice, you advocated for them, or because you want it to work out. Especially on a small team, when you have limited resources and need help, there can be a bias towards wanting a hire to work out or making do and working around someone you know is not an A player. I think it comes from feeling that having to replace someone would be a huge hindrance.


In fact, the long-term consequences of keeping a B player around can be disastrous. It’s even more important on a small team to make quick decisions when it’s clear someone is not the right fit.


What do you do during the first hour of your business day and why?

I write down the three things that I want to get done that day. I think a longer or more complicated list blurs your focus. I try to give myself plenty of time to go through the exercise and plan out the day, trying to adhere to the “measure twice, cut once” philosophy.


What’s your best financial or cash-flow related tip for entrepreneurs just getting started?

Models are great fundraising and forecasting tools when used to make forward looking projections based on current traction. The fewer rows in your “Assumptions” tab the better. I think it’s better to present an honest snapshot of what is going on today, rather than a model that shows how you could be doing $50 million in revenue five years from now.


Quick: What’s ONE thing you recommend ALL aspiring or current entrepreneurs do right now to take their biz to the next level?

Focus on the work in front of you. What is the next step? No need to waste any time thinking about the challenges of managing hyper-growth or who should design your offices.


What’s your definition of success? How will you know when you’ve finally “succeeded” in your business?

Increasing profitability and having no need for outside cash would feel like we were on a path to real success. We would be free to work against our own timelines and not be influenced in any way by the pressures that come along with the needs and responsibilities of outside investors. It would also give us complete freedom to pick and choose investors with a long term view. This would be a solid first step in our advance towards the larger vision.



Originally published by StartupCollective.


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Author : Young Entrepreneur Council

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

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