When you have built and sold a business, people tend to assume that you have reached the end of your entrepreneurial journey.
You have ultimately reached success, made the money and proved that you can do it.
And people have asked me why I would put myself through starting again.
For me, the answer was simple: ‘I wanted to.’
There was no pressure to start another business. There was a desire to go again, knowing what I know now, and to see what we could do differently.
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Building our last business, Natural HR, up to the point of acquisition taught me and my husband, Jason, an enormous amount.
Starting our new business, Learnient, has given us the opportunity to put those lessons into practice from the outset.
I was even told I had been badly advised to do it, that I had made enough money from my previous business to last me and should ‘enjoy it’.
There is an argument behind that. If you haven’t come from a background where financial security is guaranteed, you learn to make things last.
But there is another side to that thinking: ‘If I have already proved that I can build and exit a business, why shouldn’t I challenge myself to see what I can achieve next?’
Natural HR followed a venture capital route and I am incredibly proud of what we achieved, but the journey came with enormous pressure and a sense that the business had to keep moving towards a particular outcome, even if it meant making sacrifices.
This time, we have options and we’re deliberately building differently. We want to create a great business, enjoy the process with experience behind us and see where it leads.
That might still mean bringing in investment, or hiring senior leadership at some point in the future, but none of those things have to define the business from day one and that’s a huge luxury.
Of course, being a second-time founder does not make starting again any easier. You forget just how hard it is to start again.
You go from having an established structure and people around you to doing almost everything yourself.
Having gone through the process already, one of the biggest lessons from our first business was the importance of governance and structure.
When you are focused on growth, paperwork, processes and compliance can feel like administration that can wait.
But if you eventually reach due diligence, everything comes under scrutiny.
That is also so closely connected to founder dependency. Building a business that can operate without you is not just about preparing to sell. It’s about creating options, whether that be the option to step back, appoint leadership, or scale sustainably. This time, we are thinking about that much earlier.
Technology has also changed so rapidly since we built Natural HR, which became people-heavy as it grew.
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Today, automation and AI mean there are opportunities to build a leaner business without compromising the customer experience.
Being lean does not mean being small. It means being intentional with our time, resources and capital.
With the right experience behind us, our aim now is to create another great business and to enjoy seeing where it takes us next.
Ultimately, the biggest difference second time around is that the business is no longer running my life; I am running my life and my business with intention.
I still have the inevitable ‘what if?’ thoughts.
But there is something empowering about knowing you have done it before, knowing you can do it again, and being able to choose what you do differently.
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