Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Devin Golets, Founder and CEO of Tailwind, located in Toronto, ON, Canada.

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

Tailwind is a student development organization focused on providing proactive support to set students up for success as they transition into post-secondary education. We believe in eliminating obstacles and barriers, or headwinds, for students by providing them with strategies and tips, or tailwinds, to help them thrive in a post-secondary environment. We serve high schools, colleges, universities, and organizations such as the YMCA to help their students make a successful transition into post-secondary. We also support students and families directly. Our products and services include a "Ready to Launch" online program, 1:1 counselling, and group support.

Tell us about yourself

My name is Devin Golets, and I'm from Toronto, Canada. I loved my undergraduate experience at Western University, and when I graduated, I started working for the school in Recruitment. For a few years, I helped hundreds of students manage the transition into the first year. I then transitioned to work in one of the faculties as the Career Services Officer, where I coached hundreds of students on managing their next major transition: life after university. Throughout this time, I co-founded an Education Consulting startup and that ignited my interest in entrepreneurship. I left Western University to work at Top Hat, a successful EdTech scale-up and learned the ropes about all things tech, sales, and startup life. I brought all of these experiences together to start Tailwind in the fall of 2019.

What motivates me each day is that I'm working on something that combines all of my interests and previous experiences. I'm also inspired to help thousands of students with many headwinds right in front of them. Covid-19 really messed up the student experience for almost every student, and there are still repercussions that students feel today from this. Every day, I see how stressed out students are with things like the war in Ukraine and the rising costs of housing and food. My goal at the end of the day is to help students have more fun, be excited about post-secondary, and feel less stressed and anxious. That's why everything we do to help students is co-inspired by them, and we keep this in mind: how can we help this student feel more excited and less stressed? Because we really want them to have as much fun as we did when we were students (speaking on behalf of the team).

What's your biggest accomplishment as a business owner?

There have been a lot of big accomplishments, so it's hard to pick just one. Getting that first customer, your first five customers, your first acknowledgment in the press, your first hire... they're all big accomplishments that I'm proud of.

But if I had to pick one, I'd say the biggest accomplishment may actually be just the fact I've gone all-in. Some of those other accomplishments, like revenue, can be called "vanity metrics." I think something I will never lose, no matter what happens to Tailwind, is that I have done literally everything I can to give this business the best chance possible at helping people and the best chance possible at being a startup that finds product market fit and captures a viable and sustainable business model. The commitment I've made, through ups and downs, is likely the biggest accomplishment because I will take it with me no matter where I go and no matter what happens with Tailwind.

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

One of the hardest things is that you're responsible for everything, especially if you are a solo founder. Even if you hire employees, you are still responsible for the hiring and recruiting process, communicating the values, mission, and vision for the company, and truly understanding your employees well so that you can put them in a position where they can succeed and feel fulfilled, while also fulfilling the company's mission. I have been reading the book "Extreme Ownership" by Jocko Willink and Leif Babin, two former US Navy SEALS. As the title suggests, it is a bit extreme, but I think that's what great leadership does look like. You must have extreme ownership over every aspect of your business, which is hard because, depending on the complexity of what you're building, there can be many aspects of your business, therefore, lots of responsibility.

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

  1. Combine "just get started" with some entrepreneurial education. It's important to just get started on a business, but I think it's silly to say that's the only real way you learn and develop as an entrepreneur. Yes, nothing will teach you as much as starting your own business, but you'll save yourself headaches, time, money, and energy if you complement the drive to start with an appetite to learn from other sources. Look out for books, articles, YouTube videos, incubators/accelerators you can join, clubs on campus, courses... anything that will teach you the ropes of entrepreneurship! I'm always learning something new every week, and the lessons come from both my experience building and also from digesting educational material.
  2. Search for some free tools and take advantage of them while you get started. If your business has any element of tech, which it likely does, then explore the free and low-cost tools the internet provides. There are lots of low-code options out there and other platforms that have free services. Regional innovation centres in Ontario, Canada, have free business advisory, as do many small business centres and college/university campuses. If you go looking for it, you may be surprised to find how many free tools and resources there are to help you get started.
  3. Join the community and entrepreneurial ecosystem. You'll meet so many amazing people; the more conversations you have, the more you learn, and your business will improve. If you're a student, join a club on campus. Or, search for entrepreneurial events, conferences, and mixers in your city. Reach out to your friends that you know are entrepreneurs. In the span of a year or two, you'll be amazed at how you are now a mover and shaker in the entrepreneurship ecosystem.

Where can people find you and your business?

Website: https://www.teamtailwind.ca/
Instagram: https://www.instagram.com/dev.o92/
Twitter: https://twitter.com/DevinGolets
LinkedIn: https://www.linkedin.com/in/devingolets/

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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