Jill is the founder of Hustler Sophisticate Speaker Series, Business Bootcamps and Head Start Mentoring. She's a sought after Keynote and TEDx Speaker that changes people's lives by challenging their limits. She
brings actionable takeaways to implement into your businesses and life right away for
In addition to her many facets, Jill is also a successful Realtor and business coach, focussed on helping people overcome their success blockers so they can achieve their goals!
In our interview with Jill, we explore her origin story and entrepreneurial journey.
Hello Jill. Thank you for participating in this Q&A session. Please give us an overview your career, and journey as a Keynote speaker and Executive coach?
Jill: I'm a collector of experiences! In fact I've had over 75 jobs/businesses. Now, that's neither cringe worthy nor applause worthy, simply a fact. I'm also such a curious human who loves to solve problems. I began my business coaching organically. I was a very successful Realtor and people kept on asking me how I achieved such success in sales, clients and obtaining media, so I quite earnestly began coaching others. This was a lightbulb moment for me. I realized that this was what I was made to do and this is what filled me with Joy. This was my JAM!
Today, my executive business coaching is the foundation of everything else I do. It's my job to help others see things differently, to see their possibility and to break down the obstacles to their success. I help people to ‘Uncover’, and then to ‘Overcome’ their success blockers so they can 'Crush' their goals!
Where did your passion for Keynote speaking and Executive coaching come from?
Jill: My childhood was filled with abandonment and abuse, so it's my mission to help others and to give them the support, love and accountability that I never had. I'm here to change lives and open people up to their brilliant possibilities!
I change lives! To serve others and to help them is as necessary as breathing for me. - Jill Sinclair
What do you attribute your success to as a Keynote speaker and Executive coach?
Jill: My ability to relate to people and stand wholly in my genius. I'm able to connect very quickly with clients and my audience, and give them what they need, not what they think they want.
It's in my ability to have people open up in their vulnerability so I can truly understand what message and help they need from me. I'm not afraid to be bold in my conversations for change.
It's my job to help others see things differently, to see their possibility and to break down the obstacles to their success. - Jill Sinclair
What key challenges have you faced in your career to date, and how have you navigated these?
Jill: Most recently, I would say Covid. I was going to begin my speaking tours across North America in March of 2020, beginning with Josh Altman, TV Star of Million Dollar Listing LA. Covid came in and said “Nope”. So, I not only had to pivot, I had to really look at how I was serving and who really needed support.
In those reflections, I found that it was our youth. I speak a lot at Universities and I had the opportunity to speak at the University of BC at the end of February 2020, and the young people came to me afterwards and said that no one speaks to them like I did. They said that no one listens to them like I did and how could they get more of me. So, knowing that they needed help, I decided that I would put on a free, non-profit contest in the middle of a worldwide pandemic, and give away over $100,000 worth of prizes! (rent for a year, a car, biz coaching, personal trainer, wardrobe, fitness equipment, etc).
I knew that I needed to step up and bring hope, help and opportunity to our young people, because I was given that calling.
Has your career been influenced by any past or present business leaders, and how?
Jill: I volunteer as a mentor for at-risk and underprivileged youth, with 1-1 and group sessions. I look to our young people for their resilience, their openness and their dreams.
They are who inspire me. Seeing the hardships they face and how they turn their lives around by simply having someone who believes in them and holds them accountable.
Let’s talk about your book Hustler Sophisticate. What’s your book about and who is its target audience?
Jill: Woooop! I wrote Hustler Sophisticate to coincide with my very first Hustler Sophisticate Speaker Series I produced, hosted and keynoted at. I brought in Ryan Serhant, TV Star from Million Dollar Listing NY to keynote beside me, because if I’m gonna do something, i’m gonna go big.
To me, a hustler is someone who can't stop, and won't stop. It's someone who is resilient and will get up again and again, because they believe so strongly that what they offer is so freakin' valuable, and that achieving their goals is as necessary as their breathing.
A sophisticate is someone who takes pride in who they are and how they carry themselves. Understanding how to communicate in such a way that their influence reaches those who they come in contact with. My book is for those who want more in life and need to hear it from a resiliently tenacious human who will never give up!
In the book, I give tactical advice and scenarios that people can relate to, so they can implement these changes in their lives to get the success they want out of it.
What’s your favourite chapter in the book and why?
Jill: My favourite chapter is Chapter 8 - Say yes and figure it out along the way.
Opportunities are all around us and what usually stops us is...us. Us and our insecurities. When we say YES, we also must metaphorically, jump in the deep end because that action commits us and it forces us to figure it out. See, once you jump in the water, you have to figure it out; beginning with treading water, to doing one small breath stroke at a time. Before you know it, you’ve just swam across the ocean and reached your goal!
I knew that I needed to step up and bring hope, help and opportunity to our young people, because I was given that calling. Jill Sinclair
Before concluding this interview, is there anything else you would like to add about yourself, services or your book?
Jill: I change lives! To serve others and to help them is as necessary as breathing for me. It truly brings such joy and purpose to my life to help others uncover their success blockers through deep diving conversations, and then to develop a strategic plan to help them overcome these blockers. That my friend, is where the magic is!
We’ve come to the end of this Q&A session. We would like to thank you Jill for participating in it and we wish you all the best.
Jill: Thank you.
Opportunities are all around us and what usually stops us is...us. Us and our insecurities. - Jill Sinclair
This article was originally published in Issue 13 of The Business Anecdote magazine.
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