Kemi Ajumobi 
Shelly-Ann Aqui is an award-winning mentor, strategist, and transformational business and life success coach from Trinidad & Tobago with over 25 years of entrepreneurial experience. Starting with just $40, she transformed her life creating a seven-figure enterprise, proving the power of resilience, vision, and strategy.
As Executive Director of the Positioned to Propel Success Academy, she helps women entrepreneurs scale with her Life by Design Framework, blending culturally tailored strategies, digital innovation, and personal development. Her clients have achieved remarkable results, doubling annual revenues and building lasting financial stability.
Beyond coaching, Shelly is the founder of the PRVM Performing Arts Academy, visionary behind the Picture of Possibility Tribe, and host of conferences and masterminds that empower women globally.
Most recently, Shelly-Ann received the 2025 Entrepreneur Excellence Award, solidifying her impact as a voice for women entrepreneurs everywhere.
Recognised in regional and international media, Shelly is passionate about helping women of colour reclaim their power, rewrite their stories, and create lasting legacies.
What type of childhood did you have and how has it influenced who you are today?
My childhood was filled with creativity, curiosity, and responsibility. I learnt early to lead, to nurture, and to serve. Those early experiences shaped my drive, discipline, resilience, community building skills and my passion for helping others grow.
Starting with just $40 to building a seven-figure enterprise, what were some key turning points in your career and how has your business evolved till date?
My journey began with nothing but faith, a borrowed laptop, and $40TT, money that wasn’t even earmarked for a business. It was grocery money. It was a need to stay financially stable and be present with my daughters as I felt I was visiting their lives because I was so busy with work and day to day responsibilities. But when you’re called to purpose, you feel it in your bones. I used that $40 to start my first business and from there, I built slowly, intentionally, with discipline, resilience and relentless consistency. The major turning point came when I shifted from hustling to strategising. Once I embraced systems, mindset work, and aligned my business with my purpose, everything accelerated. That’s when the Positioned to Propel Academy (PTPA) was born — and from there, the work expanded into 30+ countries across the Caribbean, the U.S., Canada the U.K., and Africa. Going from $40 to seven figures wasn’t luck, it was clarity, community, and courage… the trifecta that still shapes my work today.
Personal experiences shaping your coaching philosophy
Every part of my life, the struggles, disappointments, betrayals, triumphs, taught me that success without wellness is self-destruction in disguise. I learnt the hard way that hustle culture leads to burnout, not breakthrough. My coaching philosophy is rooted in wholeness. I don’t teach women to chase success; I teach them to build a life that sustains success. My experience as a mother, educator, entrepreneur, and woman rediscovering her own worth, guides every client interaction. My story is the blueprint for my philosophy: Heal first. Align next. Learn. Build always.
Core components of the “Life by Design Framework,” and how it is helping women entrepreneurs achieve success
The Life by Design Framework is built on four pillars:
1. Clarity: Knowing who you are, what you want, and why it matters.
2. Alignment: Making decisions that honour your purpose, not your pressure. We design lives we enjoy, not endure.
3. Systems: Creating structure so your business supports your life, not the other way around.
4. Embodiment: Becoming the woman you envision through mindset, habits, and self-trust.
This framework helps women shift from overwhelm to ownership. When you design your life intentionally, business growth becomes a natural extension of inner transformation.
When your business took a leap, how did changing your mindset set you up for greater success?
I realised the biggest battle in entrepreneurship isn’t financial, it’s internal. Once I stopped negotiating with my limitations and started partnering with my identity and capabilities, everything changed. I had to become the woman I promised myself to become. That mindset shift unlocked room for accelerated growth, expansion and abundance, and that’s when my quantum leap happened.
As a mentor for women entrepreneurs, what common challenges do you see, and how do you help them overcome these obstacles?
The four most common challenges are:
• Lack of clarity
• Imposter syndrome
• Fear of visibility
• Trying to do everything alone
I help women overcome these by teaching strategy, breaking belief barriers, community-building, and most importantly, self-belief. Women don’t need more hustle — they need support, direction, and structure.
The power of a confident woman
Women experience a lot of challenges in the business terrain. I will share an experience. I went to a business networking event. And like it is with such gatherings, opportunities always present themselves, and I got one, but I was openly questioned by a prospective client about my capability because I was the only woman at the table. That didn’t make me shrink, it boosted my confidence and I proved my value calmly and assuredly. Guess what? At the end of it all, his disbelief changed to respect. Experiences like these will always happen, especially to women. We must learn how to respond to skepticism under pressure. Such experiences just show that it is important to know your onions and always be prepared, embrace optimum composure and poise to deliver what you carry on the inside of you about your business, regardless of the circumstance.
What peculiar challenges have you observed with women who lead?
From my point of view, I have observed that, among other challenges, women who lead are burdened with expectations from society. This can be a distraction as it puts them in a position of the pressure of balancing being emphatic (as the situation demands) and being congenial. What happens as a result of this is that women are then positioned to consistently prove their capability. There is also the matter of work-life balance, which men aren’t asked. So, the challenges with women leaders are there but there is grace to go through each of those challenges. It doesn’t change the fact that they exist, it just means we need grace and grit to overcome them.
Business goals and family commitments, where is the meeting point?
At the beginning, balancing both was perplexing. It took a lot from me and was draining. I believe it took a great toll on me because I wanted to do all- be a great mother to my daughters, a good wife, be there for family and friends. However, I also had a great pull towards building a prosperous business. These expectations came heavy on my shoulders and it often led to feeling guilty, being tired and severe burnout became the order of the day because I wanted to be there for everybody.
The only thing that made me pause to do a rethink was a health scare and that came from severe exhaustion. That was my wakeup call. I realised that anything I do shouldn’t be at the detriment of my health. It was an eye opener and I started to prioritise my life and shared it with my husband and children, who also got involved in my business. This decision produced positive results. I was indeed excited when I started seeing my daughters involved at my live events.
What is the greatest lesson life has taught you?
That you can start over at any time. Redemption is real. Reinvention is powerful. And God always uses every chapter, even the painful ones, to prepare you for purpose and position you to propel.
Practical steps you recommend for women looking to reclaim their power and rewrite their professional narratives?
1. Get quiet; listen to your life.
2. Identify the story you’ve been living and the story you want to live.
3. Detach from roles and titles.
4. Build new habits that support the woman you’re becoming.
5. Invest in mentorship: Identity work requires guidance.
How do the PRVM Performing Arts Academy and the Picture of Possibility Tribe complement your work as a coach?
PRVM nurtures talent, creativity, community and confidence…the foundation of leadership. The Picture of Possibility Tribe is where women grow and thrive together, break generational patterns, and rewrite their futures with business to create time, location and financial freedom. Both platforms allow me to shape women holistically, mind, body, spirit, and purpose.
What role do community and collaboration play in the success of women entrepreneurs?
Community is currency. Collaboration is acceleration. Women succeed faster when they stop building alone. My greatest opportunities and success leaps came from aligned relationships, mentors, sisters, partners, clients. No woman rises by isolation.
How do you foresee the evolution of women entrepreneurs in the coming years, and what strategies will they need to stay ahead?
The future belongs to the aligned woman, not the exhausted one. Women will lead the next era of business, guided by intuition, innovation, wellness, culture and community.
Strategies they’ll need:
• Embrace technology
• Improved business ethics
• Strengthen personal branding
• Build global networks
• Prioritise wellness
• Focus on legacy, not just profits
What day will you never forget and why?
The day my husband told me he wasn’t going to continue to fund my award shows. I realised “NO” can be a huge blessing and the push I needed to become the woman I needed to be, and the beginning of the birth of a woman who would pursue a global mission of empowering women to embrace possibilities and step into their greatness. It wasn’t a setback, it was a divine intervention.
What makes Trinidad & Tobago tick?
Our rhythm. Our resilience. Our creativity. Trinidad & Tobago is a tapestry of culture, courage, and Caribbean excellence, and that spirit fuels everything I do.