How to be a Side-Hustler: A Definitive Guide


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Having a job with great pay and solid benefits is rewarding, but there's one thing that's even more meaningful: working for yourself! But, we all have bills to pay and responsibilities we've made, so most of us don't have the luxury of immediately quitting our day jobs to pursue our own self-employed dream careers.

So, how do you make your aspirations of becoming your own boss come to life? Enter the side hustle. Come join our lineup of speakers as they delivers a highly tactical tips and tricks on the how (and why) behind starting a successful side hustle while keeping your day job.

Our speakers will cover:

  • How to identify lucrative market opportunities that align with your interests
  • Prioritization, time management and how to structure a daily routine that's optimized for success
  • Getting published and featured by top publications like Forbes, Entrepreneur and Inc
  • How to avoid getting fired and sued with your side business (from personal experience)
  • Why having a side hustle will create opportunities, rather than sitting around and waiting for big breaks
  • and much more...



  • 6:30-6:45pm: Check-in & Networking
  • 6:45-8:00pm: Panel Discussion & Q&A
  • 8:00-8:30pm: Networking


Hang about with fellow aspiring side-hustlers!

About the Speakers

Tom Feeley Photo

The Digital Squire

Tom is a digital strategist, designer, and writer who helps small businesses gain traction and visibility. He enjoys creating additional passive income streams, the most recent through Omni, a rental and storage service.

He is also the founder of The Digital Squire, a digital concierge service that’s combines the strategic approach of an agency with the tactical execution of a virtual assistant.

Click here to go to The Digital Squire.

Catherine Maldonado Photo

Web Developer,

Catherine is a full time web developer living in Somerville leveraging her communication and tech skills from her day job to navigate the promotion of her side projects. As an escape from being on the computer all day, Catherine created TeePearls, an accessories line constructed from recycled tshirts and selvedge fabric. TeePearls has been featured in the Boston Globe and was the crafting project in Boston for Etsy’s global Craft Party event in 2015. An inquisitive nature and genuine interest in the community have organically lead to unique opportunities to reach a wider audience as well as find fulfilling work. Catherine is an active member of the coding community which recently lead to the launch of her first Skillshare class. To Catherine, success means finding ways for her side projects to fund themselves as she finds creative ways to scale them such as moving from writing blog posts and selling products online to teaching classes and retail opportunities.

Rik Ganguly Photo


Rik works as an analyst in a healthcare consulting firm, where he uses health data to guide state governments in making data-driven policy decisions. He has provided analytic/statistical services to predict the impact of hospital mergers, offered technical assistance to Medicaid programs, and built powerful data tools to assess for parity in preventive and mental health services. Rik also co-founded Ridj-it ( with his friend, a travel tech company that provides coordinated carpooling, ticket bookings, and event planning to crowdsourced adventures throughout New England. The idea for Ridj-it was born out of an "aha" moment; Rik and his friend were hiking in the Whites and realized that there wasn't a consistent and reliable way to get to trailheads for those without a car. They realized this disconnect applied to other types of outings and adventures beyond city limits, and went to work to build the Ridj-it platform. When he is not juggling two jobs, Rik enjoys hiking, reading, receiving guilt-ridden text reminders from his mom on why he hasn't called, and a good game of soccer.

Sapna Tyagi Photo

P Lab

Sapna is currently the founder of P Lab, an independent Product Consulting firm offering Product management & marketing services to local startups. She serves as a Director at Founder Institute and on the leadership team for Women in Product, Boston chapter. Sapna is also a licensed REALTOR serving the Boston metro-west area for luxury home buying & selling.

Prior to her entrepreneurial ventures, Sapna served in Product leadership roles at, Invaluable and TripAdvisor where she managed product for multiple business lines, including B2C, B2B as well as B2B2C products. Sapna started her career at Microsoft where she spent a decade as a product and engineering leader launching successful products like Office 2007, Bing & Ads International, Bing on iPad, Bing on Xbox and Bing News. She holds a Masters in Information Technology from Massachusetts Institute of Technology, Masters in Operations and IT from Worcester Polytechnic Institute and a Bachelor of Civil Engineering from National Institute of Technology, Rourkela.

Rachel Cossar Photo

Choreography For Business, LLC

Rachel Cossar is an embodiment expert with a unique background in nonverbal performance. For 15 years, she trained and competed as a Rhythmic Gymnast on the Canadian National Team. From this career, she joined the Boston Ballet, performing lead roles in front of audiences at the Boston Opera House, and stages across the globe. While dancing professionally, Rachel side hustled as a prominent food blogger in the greater Boston area. On the tails of her career with Boston Ballet, Rachel founded Choreography For Business, LLC. a consulting practice that focuses on nonverbal communication in the workplace. In working with Rachel, clients receive focused and expert attention to details in common postures and body language.


Rachel has developed experiential programs tailored to meet the needs of the restaurant industry, hotel hospitality, sales teams, consultants and fundraisers among others. Rachel’s unique physical expertise enables an understanding of the importance body awareness both for ourselves and all social interactions.