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Andy Tryba, CEO x3, on how to achieve entrepreneurial success (Part I)

Irina MarcianoIrina Marciano
August 30, 2017

Andy Tryba has spent the last 15 years as CEO of multiple successful startups, including Crossover, EngineYard and RideAustin. Prior to starting his journey as an entrepreneur, Andy was the Director of Strategy at Intel Corporation, where he ran a group focused on analyzing and predicting the trends surrounding technology and work. He was also advisor to the US White House, studying the future of engineering talent.

We sat down with him to learn more about what it takes to be a successful entrepreneur, how he manages to run three companies at once, and what he’s learned along the way. Andy’s incredible insights couldn’t be constrained to one blog post, so we’re bringing you this interview in installments.

Here’s Part I of our chat with Andy Tryba on entrepreneurship.

Hi, Andy! Thanks for taking the time to chat with us. How did your journey as a start-up founder begin?

My first startup was a medical company called ExtendMD, which focused on chronic disease management. I then started a location-based fuel company called FuelMe, which was the first on-demand gas delivery service. I’ve always been interested in businesses that disrupt the industry model, and that apply technological solutions to the world’s challenges.

Today, I run three companies. The first is Crossover, which is an online talent marketplace. We aim to redefine the way people work by connecting companies with the best, high-skilled talent from around the world. The second is EngineYard, which enables Ruby developers a full stack capability to easily deploy and manage their apps on AWS.  Finally, there’s RideAustin, the first non-profit rideshare app built for the Austin community.

Wow, that’s ambitious! How do you balance 3 projects at the same time?

I find it incredibly fun to run multiple companies at once!

It certainly is a challenge when it comes to time management, but I fundamentally believe that people have more time in their day than they realize.  There are 168 hours in a week. If you sleep 8 hours a day everyday – that’s 56 hours.  So you have 112 hours left over in your week where you’ve had a good night’s sleep, you’re awake and you can be doing something. Even if you were to spend 50 hours working on one company, you still have 62 hours left over to focus on other priorities. Of course, you have to eat, and spend time with your kids, and balance all of that. But in my mind, as long as you remove all the time that you waste, you can get a lot more done than you think.

I recommend people measure their days in 10-minute increments. You’ll realize there’s tons of time that you just waste. You should look at each time block and think that if I knew I only had a day to live – would I spend those 10 minutes that way. I think people don’t prioritize their time well, and don’t realize where they lose time. Measure your time, and eliminate anything you don’t get pleasure out of. You’ll find you have a lot more time than you realize.

What would you say are the top skills needed to be a successful entrepreneur?

It comes down to 3 things:

  1. Execute. People always talk about the importance of being willing to take risks. But I think it goes much further than that – you can’t just take risks, you have to be super execution-focused.I meet people all day that have a ton of ideas, but they don’t do anything with the ideas. They sit back and talk about those ideas they had, that could have been big, but someone else did it first. You have to take the risk to go do it, but more importantly, you actually have to put pen to paper and do something about it. There’s plenty of people who talk about wanting to change the world, but they’re very comfortable with their current job, and they’re not willing to actually take the steps to execute. If you’re not willing to work those extra hours to make it happen, you’re not going to succeed as an entrepreneur. And that’s fine. There’s plenty of people who shouldn’t be entrepreneurs.
  2. Be a student of history. When you look at the history of modern business, people have tried different ways to solve problems, tried out different business models, and been impacted by various trends. You have to be able to look at those trends in the light of things that have occurred throughout time.I know a guy that basically looked at all of the major internet trends that occurred in the US, and then said, “Okay, which of these are highly localized, that emerging market countries will need to replicate on their own?” Search engines, for example, or dating sites, are examples of crucial internet trends which are typically country-specific. So he isolated those trends, and then invested in the companies that he saw as the future of the internet in each country. He was wildly successful. By being a student of history and studying how society has evolved, you’ll see where you should spend your time. Read the books, study your history.
  1. Time-balance. Whether you’re starting a company or running multiple companies, if you don’t realize your time is your most precious asset, it’s going to be really hard to succeed. You have to know how to drive productivity within yourself and others.I map out not only my calendar, but also my staff’s calendars, and their team’s calendars. You have to think very deliberately about this – where do you want your people spending their time? Everyone agrees that it’s a leader’s job to set priorities, but most people stop there. I think it’s important to translate those priorities into numbers of hours. I tell the team, “Your priorities are A, B, and C. I want you to spend 60% of your time doing A, 30% of your time doing B, and 10% of your time doing C”, and then I have them measure it. It’s important to have that discipline and to go into that next level of guidance. It’s your job to make sure there’s not a priority D, E, F that distracts your team from A, B, C.The goal is to provide relief from overload. I don’t believe people should work 100 hours a week. For most people, 40-45 hours is the right number. But most of us waste a bunch of time that extends us past our hours. If you don’t give your team the right guidance on how much time to spend on each priority, they’re likely to focus on the wrong tasks and lose a lot of time.

It seems like the issue of time plays an incredibly important role in your life.

Definitely! There’s a great book by Cal Newport called Deep Work. You have to spend long stretches of time thinking about things to come to right solutions. If you get interrupted, you never get to that higher level of thinking. It’s like sleep; only REM sleep really matters, and if you’re woken up every 10 minutes, you never get there.

There’s something called cognitive residue. Basically, if you switch tasks, it takes you a while to get up to speed to a new task. The lesson is, don’t task-switch. Block your calendar. If you look at my calendar, it’s divided into these big chunks. I’m working on Engine Yard at these particular times, Crossover at these times, and so on. I don’t interweave.

I tell my team members, how you want to work is up to you. But block your calendar so you have a preset amount of time a week that you’re working on priority A, priority B, and priority C. It’s up to you how you fill that time. But work this amount of time on it, and reach that high level solution.

That’s all for now! Check back next week for part 2 of this interview, where Andy talks about his inspiration for his business ventures, the mistakes he’s made and what he’s learned, and what the future has in store.


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