Jaspar Weir – Co-founder and President of TaskUs

I believe failure is constant, and if you’re not failing, you’re probably not taking big enough risks.

Jaspar Weir is the co-founder and president of TaskUs, the leading provider of customer care and back-office outsourcing to evolving businesses around the world. A transformational rather than transactional partner, TaskUs provides its clients with access to the people, processes, and technology required to scale quickly, excel operationally, and increase the bottom line. Jaspar doesn’t think small — he wants to help change how the business world works.

Before TaskUs, Jaspar co-founded two other companies with TaskUs CEO Bryce Maddock, including a social media marketing agency and an events production business that produced the largest all-age nightclub in Los Angeles for three years.

Jaspar shares his entrepreneurial learnings with students in the Network for Teaching Entrepreneurship and guest lectures at the University of Southern California. He has been named to Inc.’s 30 under 30 list and is a two-time finalist for Ernst & Young’s Entrepreneur of the Year Award. He holds a Bachelor of Science degree in communication from the University of Southern California. In his free time, you can find Jaspar pretending to be an avid surfer, snowboarder, and mountain biker.

Where did the idea for TaskUs come from?

TaskUs started as a virtual assistant company. We were inspired by Tim Ferriss’ “4-Hour Workweek ” and thought every busy professional should be able to outsource his or her tasks. So we built that service. We scoured the globe and tested a dozen different locations before deciding to open a small office in the Philippines. After some serious struggling with the task-by-task business model for individuals, we started helping companies outsource various functions of their work. The rest is history.

What does your typical day look like, and how do you make it productive?

The only constant in my day is change. Generally, I’m on a plane twice a week visiting clients and prospects, which makes getting into a rhythm challenging.

When I am home, I have my morning ritual. I wake up and consciously do not check my phone so I can stay calm and present. I go to the kitchen to boil water and grind coffee beans. I put MCT oil, grass-fed butter, cacao, and almond milk into my blender and pour hot water into the French press. While I wait for the coffee, I meditate for 10-15 minutes, starting with an activity called GROW. I reflect on one thing I’m grateful for, one regret I have from the previous day, one opportunity for the day, and one thing that gives me a sense of wonder. When I’m done with my meditation, I pour the coffee into the blender, put it on low for seven seconds, and enjoy my deliciously hot and buttery bulletproof coffee. While I don’t get to do this routine often, when I do, I am more grounded, happier, and more focused.

To maximize productivity, I use Asana to track my progress with my quarterly and annual goals and proactively schedule time blocks on my calendar to work on my quarterly goals. This is called “Prime Time,” and it happens for at least 90 minutes a day.

I also take notes on every client or prospect meeting. I include details about where we met, what we ate, and any pieces of personal information that may come up. I always input this information into Salesforce, but I prefer to use Evernote, either on my computer or phone. If I’m at an event or a conference, I will try to find time throughout the day to take notes. I even excuse myself at dinners and quickly jot down notes on my phone in the bathroom so I don’t forget. This information is gold.

How do you bring ideas to life?

What’s more important than bringing ideas to life is figuring out which ideas to kill. One weakness I’ve received feedback on from my team is that I tend to get really excited about an idea and drag resources and people along with me. When the idea is good, this leads to speedy execution and has a positive impact on the company. However, when the idea isn’t fully thought through, or when I’m not ready to fully commit, it can waste time and resources and have a negative impact on morale from all of the starting and stopping.

To deal with this, I’ve instituted a 24-hour waiting period on sharing any new idea — similar to buying a firearm. When I have a new idea, I really think it through for the day and sleep on it. If I still think it’s a great idea after the restriction is up, I share it with Bryce or someone else on my team who tends to be a bit more grounded and critical and can help bring me down to reality. If it passes through both of these filters, I seek the buy-in of any key stakeholders to gather feedback. Once everyone is on board, I develop a project plan with action items.

What’s one trend that really excites you?

AI and the future of customer service. AI is getting a lot of buzz right now, but we still haven’t seen many good enterprise use cases in customer support, and that’s because creating seamless AI experiences is tough. I think the space is moving more slowly than reported. Customer expectations are high, so putting any form of AI that isn’t nearly perfect in front of customers will blow up in a brand’s face.

With that said, I think the future of support for many brands is a messaging-type experience, using AI and self-service prompts and a seamless handoff to a customer service rep for higher touch challenges beyond what a computer can solve.

What is one habit of yours that makes you more productive as an entrepreneur?

Meditation. I took a class along with some early TaskUs employees, and to this day, it’s still one of the most important things I started doing professionally. It’s frustrating, it’s challenging, and it sometimes makes me restless or even angry, but I almost always sit for at least 10 minutes of meditation before checking my phone or rushing to start my day.

What advice would you give your younger self?

It’s going to be all right. Stay focused, and trust your instincts. Also, stretch more, and buy Apple stock.

Tell us something that’s true that almost nobody agrees with you on?

Most professionals don’t value their time logically. For instance, mid-level and higher-ranking professionals shouldn’t drive — they should take Uber. If you’re making a decent salary, your time is more valuable than the way you treat it. You should outsource your driving so you can be a passenger and take phone calls, answer emails, or spend the time relaxing and recuperating from work. I think people should apply this to any other time-consuming aspect of their lives they don’t enjoy, whether it’s doing laundry, cleaning, driving, or even shopping for groceries or cooking. If you truly value your time, there are ways to get back hours in your day if you’re willing to go against some social norms.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Keep learning. One of the most important jobs of an entrepreneur is to spend time learning. I think every entrepreneur should understand current events within and outside their business, seek to learn about other business models, and expand their frame of reference. Doing so allows entrepreneurs to see the big picture and navigate their companies in the proper direction.

What is one strategy that has helped you grow your business?

Dinners. Everyone eats dinner, and we’ve had great success hosting intimate events that bring together prospects, clients, and other interesting, influential people. We call them “Ridiculously Good Dinners.” Instead of reaching out cold to prospects to pitch them an idea, we invite them to an enticing dinner and build a relationship. We don’t pitch TaskUs; we focus on creating a great experience with the right attendees and let relationships form naturally. These events don’t need to be particularly fancy, expensive, or filled with only CEOs. Anyone can do this and take advantage of what happens when you break bread and get to know people.

What is one failure you had as an entrepreneur, and how did you overcome it?

I believe failure is constant, and if you’re not failing, you’re probably not taking big enough risks.

My biggest failure was not initially hiring people who feel a deep responsibility and sense of pride in the business. I assumed that as the business owner, it was normal that I would always work harder and longer than any of our employees. This created tension among our early team — it bred distrust and an “us versus them” mentality. I ultimately realized that we simply hadn’t hired the right people. Once we had one person on board who believed in our business, bought into our vision, and worked as if they were an owner, I realized that I had made a terrible assumption. To overcome this mistake, we overhauled our hiring process (or lack thereof) to ensure we took every possible action to attract and hire the right people.

What is the best $100 you recently spent?

A subscription to Audible . I love reading, but it generally takes me a long time to get through a book because I don’t have much time or end up falling asleep after two pages. I’ve been demolishing books on Audible so much faster than I could ever read.

What is one piece of software or a web service that helps you be productive?

I use Asana to track my tasks and goals. I have running agenda items with people on my team, personal and professional tasks, and projects. I love the Chrome plugin that allows me to add a task from my webpage in seconds.

What is the one book that you recommend our community should read?

It really depends on the stage of your business, and choosing one book is hard, so I’ll choose two. The first is for everyone at any stage: “How to Win Friends and Influence People” by Dale Carnegie. It’s a classic that everyone should read.

Recently, I read Marshall Goldsmith’s “What Got You Here Won’t Get You There,” which is fantastic for anyone running a company at a later stage. It helps identify common challenges entrepreneurs have when scaling a business and empowering an executive team and what sort of adaptation is necessary for ongoing success.

What is your favorite quote?

“I find the harder I work, the more luck I seem to have.” — Thomas Jefferson


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Key Learnings

  • Having a morning ritual that incorporates meditation can help you feel grounded, happier, and more focused.
  • Take detailed notes on every client or prospect meeting — even include details on where you met, what was eaten, and any pieces of personal information that come up. You never know what information will be useful in the future.
  • Figuring out what ideas to kill is sometimes even more important than deciding what ideas to bring to life. Instituting a 24-hour waiting period on any new idea and looping in others you trust to give you grounded, critical feedback can help you kill the bad ideas and move forward with the good.
  • If you’re making a decent salary, your time is more valuable than you think. Consider outsourcing any time-consuming aspect of your life you don’t enjoy, such as driving, laundry, cleaning, or even shopping for groceries and cooking.
  • Entrepreneurs should always be learning. This ensures you’re able to see the big picture and navigate your company in the proper direction.
  • Amazing things can happen when you bring people together, break bread, and get to know one another.
  • It’s essential to hire people who believe in your business and buy into your vision.
  • If you’re always lamenting your lack of time to read, consider getting a subscription to Audible.
  • Read “How to Win Friends and Influence People” and “What Got You Here Won’t Get You There.”