Ep 29 Brenna Loury, Working Remotely Across Borders

In this episode, I reconnected with my friend Brenna Loury, one of the original founding team members of Start-Up Chile, and the current head of marketing and PR at Doist to talk about her experience of learning a new job in a new country, the challenges and rewards of working across borders, and how she helped bootstrap a tech startup that now has more than 13,000,000 users worldwide.   

Brenna shares how her company now manages more than 50 employees in 20 countries, all of them working 100% remotely. She offers tips on how to best position your company to start working remotely, mistakes startups should avoid when pitching ideas or raising funds and a formula for hiring top-notch employees. The conversation is packed with useful information and inspiring stories you don’t want to miss!

How to have a startup mindset

Most people are timid when it comes to learning a new language, moving to a new country or starting a new job. Entrepreneur Brenna Loury is not most people though. These were just a few of the challenges she overcame after moving from Colorado to Chile for a new job.

Brenna shared several great tips on adjusting to a new culture, including best practices for learning a new language, how to overcome the discomfort felt in a new culture and how to position yourself to accelerate your learning. If you are working across borders, you should absolutely tune in.  

Startup culture or stable career?

Entrepreneurs are often faced with the decision of moving away from startups into careers that seem more stable or well established. Brenna also faced this decision, here’s what she had to say.

After Startup Chile, you can’t go back to a normal job, she said. Every day is transformative, for the businesses and the entrepreneurs, as well as the clients or users who benefit from the services. At the time that Brenna was in Chile, the idea of a “Startup” was virtually unknown and there was a serious need for effective PR in the tech space. Not one to shy away from a challenge, Brenna decided to stay in tech, a decision that helped lead her her to success today. Hear the rest of the conversation below.    

Mistakes, mergers and measuring success

Every startup hopes to be successful, but how do you know when you have reached that point? For some, it’s a buyout offer from a larger company…for others, it’s remaining small or privately owned.

Brenna has had the unique experience of seeing both sides of startup success, from bootstrapping a company that has had several offers from larger corporations to pitching capital investors on behalf of Startup Chile. During our conversation, she shares several mistakes that startups can avoid, including the right way to pitch an idea and the importance of groundwork. She also shares tips and tricks to look for if a merger in on the table.         

How to hire the best employees to work remotely

The people you hire will largely determine the success of your company. Doist, the company that Brenna works for has successfully grown to over 50 employees, in 20 countries. All of the Doist employees work remotely. Here’s how they do it.

We look for self-starters, yes, but more importantly people who are a good cultural fit, she says. As your business crosses borders, look for people who can adapt to the new culture. She also points out the potential downfalls if only some of your employees are working remotely. If working remotely is an option, she thinks it needs to be 100%. She shares the logic of this approach and more on this episode of Crossing Borders.  


Outline of This Episode

  • [3:30] How Brenna started working remotely
  • [10:45] Brenna on how to position yourself in environment where you are forced to learn
  • [18:15] Hurdles Brenna had to overcome with Start-Up Chile
  • [21:15] The mindset behind accepting a challenge
  • [28:30] Common challenges when expanding across borders  
  • [30:00] Brenna shares her motivation to stay in startups career vs other types of jobs
  • [35:00] Tips for running a successful PR startup campaign and mistakes to avoid
  • [40:00] How Brenna started with Todoist App
  • [46:00] Mistakes to avoid regarding valuations, acquisitions and mergers with large companies   
  • [50:00} How to hire remote workers across borders: best practices
  • [58:15] The best of what Brenna has learned so far, regarding startups and working remotely.

Resources & People Mentioned

Connect With Nathan

If you enjoyed this episode – would you mind subscribing and leaving a rating and review?

SUBSCRIBE, RATE, AND REVIEW ON iTunes

SUBSCRIBE, RATE AND REVIEW ON Stitcher