Interested in starting your own entrepreneurial journey in coaching but unsure what to expect? Then read up on our interview with Will Greenblatt, co-founder of OutLoud Speakers School Inc., a public speaking service that provides communication and performance skills to business professionals (in-person & online) in Toronto, Ontario, Canada.

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

Communication is essential for personal, professional, and organizational success, yet nobody gets taught HOW to communicate clearly, authentically, and passionately. OutLoud is a group of actors and coaches, helping entrepreneurs and teams develop powerful storytelling, presentation, and conversation skills.

Tell us about yourself

I got into acting at the age of seven, starring in a feature film after my very first audition. Although I loved it growing up, after a bad experience at theatre school, I quit the business and became first an English teacher in Spain, then a education startup founder in China, before coming back to Canada and co-founding OutLoud with my acting mentor to bring powerful speaking skills and confidence to the entrepreneur and corporate worlds.

What's your biggest accomplishment as a business owner?

I started as half of a two-person team with no capital investment, and have built our company to 12 part- and full-time employees, and have doubled our revenue each year except 2020 during COVID. Also, my clients have raised over $150 Million USD in investment capital after working with me.

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

The emotional swings between being incredibly excited and feeling successful and completely questioning your own abilities and self-worth, often multiple times in one day!

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

  1. Make sure you are PASSIONATE about the work your company does, and make sure people can HEAR, SEE and FEEL that when you talk about your business to anyone.
  2. Get good at researching and teaching yourself to do things online; there's almost always a solution to your problems that can be found FOR FREE on the internet.
  3. Figure out what you suck at that is essential for a successful growth company, like marketing, accounting, or HR, and hire, barter or otherwise convince people who are good at it to help you. EVERYONE needs help, and you must ask for it!

Is there anything else you'd like to share?

Being an entrepreneur is the most rewarding job I can imagine, partly because it's the most challenging. Embrace the constant highs and lows, and seek out support from other founders. Oh, and get a therapist - for real.

Where can people find you and your business?


Instagram: @willgreenblatt

Twitter: @outloudschool

Facebook: @outloudschool


If you like what you've read here and have your own story as a solopreneur that you'd like to share, then email; we'd love to feature your journey on these pages.

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