Financial educator with over 25 years’ experience Andrew Woodward reveals the unexpected joy and benefits of sharing the load in a a business he had always assumed ‘didn’t have room for anyone else’ with his son
If you’d told me ten years ago that I’d be running a business with my son, I’d have smiled politely and kept walking.
Not because I didn’t think it was a good idea. Like many of us in the small-business space, I just never imagined I’d have a business that needed anyone else, let alone someone from my own family.
But as most business owners know… things change fast.
Let me tell you how it happened, and why it might just be the smartest move I’ve made.
The unexpected beginning
It all started with a meeting I had with my business coach.
This session with my business coach wasn’t just a casual catch-up. This was a deep-dive strategy session on where we would take the business in the next six months.
This is something we do twice per year, only this time, my son Blake joined the trip. He wasn’t coming to work, just to help behind the scenes and ‘hang out’ as he and my coach had become good mates over the years through their mutual love of running.
My coach had seen some of what Blake was doing to make money through a side-hustle outside his day job and asked me if he could have 90-minutes with him before we dived into our strategy session. So, while I went and had coffee with my wife at a nearby cafe, Blake got 90-minutes with my coach.
By the time he came out, something had shifted.
My son looked me square in the eye and said, “I want to be part of this. I want in.”
That wasn’t what I expected. But it was the start of something better than either of us had imagined.
Starting small while still in his job
Now, Blake was still working full-time in a corporate buying role at that point. He was good at it, too – organised, analytical and solid under pressure.
So, we agreed he’d start small. A few hours a week helping with lead generation. Some content filming. Admin here and there. No pressure, just test the waters.
But here’s the thing…when someone’s aligned with your mission, things move fast.
Within months, our business was growing rapidly. The systems got sharper, the client-flow smoother and our visibility online jumped.
He was helping me stay accountable, pushing me to evolve and I could see that this wasn’t just a ‘help dad’ project – he was taking ownership.
That momentum helped him make the decision to leave his job and go all in. That was a proud day for all of us.
Building for legacy – not just revenue
Right now, Blake’s leading our content creation and lead gen. He’s behind the voice you see on our social channels. And while we both still trip over our words on camera now and then, he’s developed real skill and confidence.
Next stop? Sales. And after that, service delivery. We’re working together on a phased plan that transitions him from the top of the funnel right through to client transformation.
Why? Because this isn’t just about growing a business, it’s about building longevity and legacy.
When you have someone in the business who’s committed for the long haul, you can think differently. You stop playing defence and start planning for scale.
More people helped. More lives changed. And, eventually, a business that doesn’t need you to run it.
What’s it like working with your son?
Honestly? It’s been one of the most rewarding decisions of my career.
We challenge each other in the best way. He spots gaps in the business I hadn’t noticed. And I get to teach him everything I’ve learned after 30+ years in money and mindset – not in theory, but through action.
Do we always agree? No. But we laugh a lot. Especially when the cameras are rolling and one of us can’t get the words out straight.
The only “tension” we have is keeping up with Blake’s ambition. He wants everything yesterday. It keeps me sharp.
So… should you bring family into the business?
Here’s the truth.
Family and business can mix – if you do it with clear intent AND there is alignment. Alignment is key in my view.
Start small. Set clear roles. Stay out of each other’s lanes. But more importantly, build with a vision that’s bigger than you. One that creates legacy, not just lifestyle. Because when you do that, you’re not just hiring help. You’re building a future that outlives your own efforts.
And that, in my view, is the real goal.
