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Meet Sasha Prasad of Freedom Tail in South End, Back Bay, and Fenway

Today we’d like to introduce you to Sasha Prasad.

Sasha, can you briefly walk us through your story – how you started and how you got to where you are today.
I never intended to be a business owner. I always had a passion for animals, and when I moved to Boston, dog walking seemed like a fun way to earn some money until I found a “real job” or started graduate school. I quickly fell in love with all the dogs I worked with and really enjoyed building relationships with my clients. The freedom of being my own boss was exhilarating, too. Since that first summer, my client load has exploded, primarily through referrals. It’s more than I can handle myself, so over the years, I hired a team of amazing and highly qualified dog walkers helping me out. Freedom Tail celebrated its 3rd anniversary this July. I’m so proud of the work we do every day and am grateful that I have a job that I love.

We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
The biggest challenge I’ve had was learning how to run a proper business. I don’t have a business background or any previous business experience, so I’ve had to learn a LOT. Bookkeeping, accounting, contracts, email marketing, social media…It’s been a lot of learning on the fly. One of the best pieces of advice I received was if you don’t know how to do something, hire someone to do it for you. When I first started Freedom Tail, I was doing everything myself and I was drowning. Now, I have a team of people helping me, which allows me to focus on the areas of my business that I am most passionate about – our clients and their dogs!

So let’s switch gears a bit and go into the Freedom Tail story. Tell us more about the business.
Freedom Tail is a dog walking and pet sitting company in Boston. There are tons of similar companies in the city, and it can be difficult to determine what distinguishes them. At Freedom Tail, we pride ourselves on putting our clients first – the dogs AND the humans. Often, the humans get forgotten by dog walking companies, even though they’re the ones paying the bills. We try to go above and beyond to keep our human clients happy. Scheduling is a breeze through our client portal. We provide off-hour walks at no additional charge, offer same-day-services, and don’t charge a cancellation fee. Our clients receive real-time updates with pictures after every walk. We host meet-ups during the warmer months so our clients can meet and socialize with our team. We’re obviously a team of dog lovers, but I’m most proud of the relationships we’ve built with our clients.

Has luck played a meaningful role in your life and business?
I was VERY lucky that the luxury apartment boom hit Fenway when I first started Freedom Tail. Most of these buildings are dog-friendly and I was able to make connections with early residents and management companies. This helped me build my client list as I was first starting.


  • Walks start at $17/half hour.
  • We offer pay-in-advance discounts from 5-15% off.
  • Pet sitting starts at $12 for a check-in and $20 for an hour.

Contact Info:

Image Credit:

Miranda Prasad

Getting in touch: BostonVoyager is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

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