What began with a fascination with human behaviour has grown into a business helping organisations develop stronger leaders at every level.
For Jackie Kennedy, the Cape Town-based founder and CEO of LeadMe Academy, the journey into entrepreneurship began with a fascination with human behaviour and what enables people to make meaningful changes in their lives.
Today, she is helping organisations develop stronger leaders through coaching, learning and behavioural change.
She discovered coaching in her early twenties, trained as a coach and spent several years working one-on-one with clients and developing bespoke leadership programmes.
But over time, she noticed a pattern. “The process I was taking people through could become a scalable offering,” she says.
That realisation led to LeadMe Academy, which aims to make coaching and leadership development more accessible. Its approach combines coaching, science-backed learning, practical workplace application and small, consistent behavioural changes.
From coach to entrepreneur
Turning that idea into a business came with its own learning curve.
For Kennedy, one of the biggest challenges was moving from being a practitioner to becoming an entrepreneur. Being good at coaching, she says, is very different from building the sales, systems, operations and team needed to grow a company.
Building trust with established organisations was another early hurdle.
As a young business, LeadMe needed clients willing to believe in the vision before it had an extensive track record.
The COVID-19 pandemic brought another period of uncertainty, but also demonstrated the value of LeadMe's digital approach. With programmes able to be delivered online, the business could continue supporting leaders and teams during a particularly challenging period.
Growing beyond the founder
One of Kennedy's biggest business decisions was to build a strong team rather than allow the company to remain dependent on her.
Surrounding herself with people who bring different strengths and perspectives has allowed LeadMe to grow beyond what she could have achieved alone.
Relationships have also played an important role.
“Many of our strongest opportunities have come from relationships that have developed over several years,” she says.
For Kennedy, navigating uncertainty means staying focused on the problem the business is solving, listening to clients and adapting without losing sight of its purpose.
What entrepreneurship has taught her
If she could go back and do something differently, Kennedy says she would establish a more deliberate sales strategy much earlier.
She shares that much of LeadMe's early growth came through relationships, referrals, and her own involvement. While those remain valuable, she believes clearer systems and processes would have allowed the business to scale sooner and reduced its dependence on her personally.
It's a lesson she believes many founders eventually learn: building a great business and building a business that can scale are two different things.
For Kennedy, successful entrepreneurship requires focus, resilience, adaptability and the courage to act without having all the answers.
It also requires self-awareness.
“You do not need to be the best at everything,” she says. Instead, entrepreneurs need to recognise their strengths, understand their gaps and build teams that complement them.
Her advice to women
For women thinking about starting or growing a business, Kennedy's advice is straightforward: don't wait for the perfect moment.
Entrepreneurship isn't necessarily an easier route to flexibility, particularly when you're balancing family and other responsibilities. There will be seasons when the business demands more and seasons when family does.
The goal, she says, isn't to do everything perfectly. It's to make conscious choices, build the right support around you and recognise that you don't have to do everything alone.
Most importantly, she encourages women to trust their ambition.
“Do not diminish your ambition or wait for someone else to give you permission. “If you believe you can create something of value, back yourself and begin.”
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