#TaskerTuesday – Samantha B. & Craig D.

Consider this: You’re in a relationship, you love working together, and you both want the freedom, flexibility, and adventure of making a living on your own schedule. What’s the logical conclusion? Being a tasking couple, of course!


This is the story of Samantha B. and Craig D., a couple of 13 years (and counting) who both decided that tasking together is better than working apart. Samantha was a graphic designer working in a corporate cubicle, and Craig was a research analyst until a company merger resulted in a layoff. After doing some tandem soul searching and realizing they both wanted to work together, on their own terms, and help other people while they were at it, they found TaskRabbit. In the two years since, they haven’t looked back!

We chatted with Samantha and Craig about their transition into being a Tasker couple, and here’s what they had to say:

Screen Shot 2018-07-09 at 9.07.43 AMHow long did it take you to build your business?

Craig: After starting as Taskers, we started seeing repeat Clients and referrals almost right away—most likely due to Samantha’s clear communication and keen sense of time. We also created an Instagram account (@taskingpros) to showcase our work and handed out business cards and flyers wherever we could, which really helped!

Samantha: We found that knowing how long it will actually take to complete a task, communicating with the Client about what to expect, and then following through with attention to detail really went a long way toward building the trust it takes to build great Client relationships. We always focus on that!

Screen Shot 2018-07-09 at 9.07.33 AMWhat’s the best thing about working together as Taskers?

Samantha: The most obvious thing is that we get to spend a lot of time together that other couples don’t get. We happen to share that special bond where we don’t want to kill each other all the time, and we actually love spending time together. Even after 13+ years.

Craig: Working with someone you’re close to adds another level of silent communication that makes the jobs smoother and quicker. For us, it’s a simple dart of the eyes, and I know she needs the screwdriver. A silly word like “lock-nar,” and she knows I need a cam lock nut.

Screen Shot 2018-07-09 at 9.06.17 AMWorking as a team, how flexible are you able to keep your work lives?

Craig: Right now, we are saving up to take one of the biggest risks of our lives–to build a tiny home on wheels and take our tasking show on the road! So, honestly, we are always on the hustle. Since TaskRabbit operates all over, why can’t we?!

Samantha: We have been building up our handyman business and trusted TaskRabbit reviews so we can make this dream a reality. You want to talk about flexibility? Maybe we want to work in the Bay Area for a few months in the summer and head somewhere else in the winter. But that’s another story for another time. If you’d like, you can follow us on Instagram @life_with_pickle to see that story unfold!

Screen Shot 2018-07-09 at 9.06.50 AMAre there any challenges to working together as a team (and as a couple)?

Samantha: Composure and professionalism are key, no matter who you’re working with, and that includes knowing when to take a back seat or offer a different solution. I have lost count of how many times we’ve had Clients find out halfway through an IKEA build that we’re married. They marvel at how we haven’t yet divorced each other.

Craig: We just tell them we remodeled our first kitchen together in 2006 and that we’ve gotten most of the yelling out since then. When working as a team, it’s about playing to each other’s strengths, not weaknesses. If someone is better with painting clean, straight lines, let them!

Screen Shot 2018-07-09 at 9.06.37 AMWhat are some challenges TaskRabbit has allowed you to overcome?

Samantha: Confidence! TaskRabbit has given us both so much more confidence and enthusiasm in the jobs we take on. Two years ago, we would never try to mount a TV in someone else’s home, let alone resurface not one but two countertops with concrete!

Craig: This confidence has given us the ability to take on the next chapter of our lives—this time with us literally in the driver’s seat. It feels really empowering.

Screen Shot 2018-07-09 at 9.07.04 AMIs there any advice you’d like to share with other Taskers?

Craig: Be honest, be communicative, and pay attention to details. Always. Sometimes, we don’t have a particular skill to feel comfortable enough with a task. We always communicate that to the Client. It’s much better to set expectations at the beginning than to realize there’s been a miscommunication halfway through a job.

Samantha: And use the chat feature! It has helped us later on so many times. I use it not only to talk to Clients, but also to mark the time we start and finish a job, to confirm what we have spoken about in person or on the phone, and to save receipts and before/after pics. It’s like a helpful little file cabinet. You’ll be happy later if you take the time to document your tasks!

We had such a great time hearing Samantha and Craig’s story, and we wish them all the best as they embrace the adventure of becoming multi-metro, traveling Taskers! After all, TaskRabbit is all about giving people that type of freedom. All it takes is the courage to make the leap!

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