Interested in starting your own entrepreneurial journey in mental health care but unsure what to expect? Then read up on our interview with Rob Pintwala, Founder of First Session, located in Toronto, ON, Canada.

What's your business, and who are your customers?

First Session connects people with the right therapist for them. Anyone struggling with their mental health or relationships, or those who simply want to improve their well-being, can use First Session to find and connect with a therapist.

Tell us about yourself

In 2018, my wife had a bad experience looking for a therapist. She sought out someone who could be caring and empathetic but was met with a sales pitch and was matched with someone who simply wasn't a good fit. She, unfortunately, gave up her search after this experience and ended up without a therapist during a time when she could have really benefited.

This motivated me to start First Session. I believe everyone should be able to choose their own therapist based on who feels like a good fit for them. To solve this, we've curated a group of high-quality mental health practitioners, produced professional videos for each of them, and added tools to help people search and connect with them. The research says success in therapy is all about having a therapist you can truly connect with—we optimize for this connection.

What's your biggest accomplishment as a business owner?

To date, having helped more than 5000 people find and connect with a therapist.

What's one of the hardest things that come with being a business owner?

For me, it's a lack of structure. When you're in a job or in school, you have deliverables. When you have your own business, you are your own boss and answer to no one. This has its perks but also can be very challenging at times.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Don't wait to find the best idea. Start by solving a problem. The key part is starting.
  2. Marketing and distribution are critical—if you have a great product, people won't just automatically find and buy it.
  3. You'll never feel ready to start a business. The best time to do it was yesterday. The second best time is today.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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