Get All Access for $5/mo

This Successful Serial Entrepreneur Shares How to Make Burnout a Thing of the Past Guideline and TaskRabbit co-founder Kevin Busque makes a 10-day vacation mandatory for every employee.

By Nina Zipkin

Courtesy of Kevin Busque

Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

Planning for your future is incredibly important, but all the paperwork and logistics can be tough to navigate.

Kevin Busque has built his career using technology to connect people with solutions to make their lives easier. In 2008, he co-founded TaskRabbit with his wife Leah Busque, a platform that let users outsource their day-to-day tasks like cleaning, moving and home repairs to a vetted "Tasker."

Three years ago, Busque stepped away from TaskRabbit to launch a brand new venture, Guideline, which streamlines the 401(k) process for growing companies.

"We're really trying to change retirement for the better, and I think 401(k) is the best tool that we have to do it," Busque told Entrepreneur. "It's just been poorly implemented for the last 30 years, so we're trying to make that fresh to get people excited about this vehicle.

Guideline doesn't have take management fees, its platform is user-friendly and employees can manage their retirement plan in one online location.

In three years, Busque and his team have raised $24 million, and they now work with more than 3,750 companies.

We caught up with Busque and asked him 20 Questions to find out what makes him tick.

This article was edited for brevity and clarity.

1. How do you start your day?
I'm typically up around 6:00 in the morning. I jump into our dashboard, look at our core metrics and then look for any anomalies, things that may be out of place or don't make make sense from the previous days transactions. Then I head into the office around 7:30 or 8:00 am. The first couple of hours in my morning are reserved for meetings with the team, as that time is the best for me to concentrate.

2. How do you end your day?
I'll check in with Jeff, who is our COO. We map out the biggest things we accomplished that day and what's on the plate for tomorrow. When I get home, I typically unplug for a few hours and hang out with my kids before they're off to bed around 6:00 to 7:00 pm, and then I'm back online.

3. What's a book that changed your mind, and why?
Extreme Ownership, by Jocko Willink and Leif Babin. It's about US Navy SEALs -- how they lead and win. I grew up in a military family, and my father instilled accountability in me at an early age. It's part of ruthlessly owning your actions and outcomes. This book is real-world albeit very very extreme examples of ownership, and it's powerful when you distill it down to actions and outcomes.

4. What's a book you always recommend, and why?
Give and Take, by Adam Grant, about [how success comes from collaboration]. I think it's important in life to understand your interactions with people. I think understanding that, what drives you and goes a long way towards [improving personal relationships].

Related: Use This Successful Entrepreneur's Scheduling Secret to Have Your Most Productive Day

5. What's a strategy you use to stay focused?
Every day I have hours in my calendar completely blocked off, where I just use it to think and write down my thoughts. It's a really good way for me to focus on the problems at hand.

6. When you were a kid, what did you want to be when you grew up?
I wanted to be a Green Beret in recon. I grew up in many different states in North America and in Europe. I was predisposed to the military and being adventurous. I think that's why I ended up being an entrepreneur. I love building things from scratch.

7. What did you learn from the worst boss you ever had?
Relentlessly applaud and support my team and never want to take credit for something that my team has done. I had a boss who always took credit for the team's work. It was very unfortunate, and we had a lot of turnover.

8. Who has influenced you most when it comes to how you approach your work?
My grandfather, who was a World War II soldier and a self-taught master carpenter. He taught me to understand everything from the bottom up. He had this saying: "Nothing to it when you thoroughly understand it."

9. What's a trip that changed you, and why?
Twenty years ago, I took a trip my freshman year in college. My friend and I went to South Africa, and we ended up at Kruger National Park. It's one of the largest game reserves on the planet and was like nothing I had ever seen before. It was a humbling experience to see how small we really are in the grand scheme of things.

Related: Shark Tank's Barbara Corcoran Explains Why You Must Make Time in Your Schedule For Fun

10. What inspires you?
My kids. I'm really striving to make the best life possible for them. My parents gave up a ton for me, and I'm doing my best to pay that forward.

11. What was your first business idea, and what did you do with it?
In the early '90s, I started a company called Crackerjack Custom Systems. I was building high-end computers for the school system, local colleges and real estate agents. It was sort of an escape for me; I had a tough time transitioning into high school. I went through some personal tragedies, and that business ended up making $45,000 a year as a sophomore. I put that toward paying for my college and travel to see my then girlfriend, now wife, Leah in Virginia.

12. What was an early job that taught you something important or useful?
Before I started my first computer company, I worked in a landscaping company building rock walls. I would come home with lots of banged-up fingers, a sore back and all that sort of stuff. I have a lot of respect for manual labor in this country, but it showed me that wasn't for me. I knew I didn't want to do that long term, and it really enabled me to focus on computers and software.

13. What's the best advice you ever took?
Focus on one obstacle at a time. I think it's nearly impossible to fix everything all at once. So wake up each day, focus on that one problem for that day and do your best to solve it.

14. What's the worst piece of advice you ever got?
At a previous startup we were recommended to follow the hype. At that company we were told to pivot and do what this company is doing. That company went out of business six months later. It was definitely bad advice at the time, and I'm glad we saw [our vision] through.

Related: Health and Beauty Mogul Bobbi Brown Shares The Biggest Time Sucker -- and What You Can Do About It

15. What's a productivity tip you swear by?
Block off time in your calendar that people understand is your time to focus, rather than falling into the email trap.

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I use an email client called Mailspring. It has a unique feature that has link tracking and email read receipts. I use the data as a way of marking things off as I've completed them. It keeps me going and progressing throughout the day when I'm not in my four-hour [block of focused time].

17. What does work-life balance mean to you?
I don't really subscribe to the work-life-balance mantra. When you do what you love as far as working, I think it just becomes life.

I do set aside time to be present with my family, but sometimes that may take a backseat, if there is a fire to put out -- and vice versa, too. When everything's well -- both family and in work -- that's when I take a vacation. So that's really what it means to me.

18. How do you prevent burnout?
This one is tough. I really love working. I focus on preventing burnout in my team. At Guideline we have a 10-consecutive-day vacation policy. It's a way to try and get them to reset, and it helps us identify any gaps in coverage in the company.

19. When you're faced with a creativity block, what's your strategy to get innovating?
I have two fantastic co-founders at Guideline. Jeremy, the head of design, has been a great friend for last six years, and we work incredibly well together. If I'm trying to think through a problem and I need a creative solution, I'll bring him in.

20. What are you learning now? Why is that important?
I'm learning how to make wine, and particularly, I'm learning how to make the tools that go into making wine -- drying racks and all of that stuff. It's sort of my meditation. I have the hardest time actually meditating. I need to be doing something, and I like to work with my hands. I love building things.

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business Solutions

Increase Productivity with This Microsoft 365 Subscription, Now $25 Off

It can make the entrepreneur life a lot easier.

Business News

Apple Pay Later Is Ending. Here's What's Taking Its Place.

The program was available for less than a year.


This Artist Answered a Businessman's 'Powerful' Question — Then His Work Became 'the Poster Child for Juneteenth': 'Your Network Really Becomes Your Net Worth'

Reginald Adams was the executive director of a Houston-based art museum for more than a decade before he decided to launch his own public art and design firm.


Harvard Business School Professor Says 65% of Startups Fail for One Reason. Here's How to Avoid It.

Team alignment isn't nice to have -- it's critical for running a successful business.

Business News

Here's What Companies Are Open and Closed on Juneteenth 2024

Since it became a holiday in 2021, Juneteenth has been recognized by some major corporations as a paid day off.

Growing a Business

I Hit $100 Million in Annual Revenue by Being More Transparent — Here Are the 3 Strategies That Helped Me Succeed

Three road-tested ways to be more transparent and build relationships that can transform your business — without leaving you feeling nightmarishly over-exposed.