Jack Henderson: building a brand through engaging content

When Jack Henderson left school, becoming a buyers‘ advocate wasn’t on his radar.

After being expelled from two high schools, the now founder and director of Henderson Advocacy initially went into the construction industry and later moved to the mining sector.

But the teenager from Wilberforce, about 60kms northwest of Sydney on the Hawkesbury River, didn’t have becoming a buyers advocate even remotely in mind.

“From a young age, I always wanted to be successful,” Jack explains.

“And naturally, when you’re young, success is a monetary thing you look at. I always wanted to earn money (but I) wasn’t very good in school.

“I was expelled from two high schools. I was just someone who never wanted to learn from people who weren’t in the position I wanted to be in.

“Naively, I looked at teachers and thought, ‘I don’t necessarily want to be a teacher and I’m not super inspired by the way you live your life’.

“I didn’t want to learn from them and, naturally, that didn’t go down too well.”

So, fresh out of school, Jack set his sights on earning as much money as possible, and as a 16-year-old, he joined the construction industry as a labourer.

He made between $80,000 and $100,000 a year and stayed in the profession until he was 21, when he became a machine operator in the mining industry.

At just 18, Jack secured his first investment property – a two-bedroom apartment in Coogee – and by 21, he had three homes to his name.

Today, he has an investment portfolio totalling $25 million, but he says those first seeds of becoming a buyers’ advocate started innocently when connections asked him for investment advice.

“It wasn’t conscious, it was just people asking me,” Jack notes.

“And obviously, I had a mentor in Chris Gray who was doing it as well. I understood the process, but I didn’t really think I would end up being a buyer’s advocate as such, but here we are.”

The beginning

Jack officially became a buyers advocate in October 2019, working for a Sydney firm for about a year before launching Henderson Advocacy in November 2020.

In his first nine months, he wrote about $700,000 in commission and immediately focused on creating a brand people recognised and trusted, complete with mascot Hender-ingo, the property flamingo.

Jack says the secret to creating public awareness started on day one, including hiring a videographer. 

“I’m a big Gary Vaynerchuk follower, and everything he said was about documenting your journey… and I essentially thought, ‘If I want people to know who I am, I need to be able to produce content’,” he recalls.

“I hired a videographer from day one, and I was producing content when no one knew who I was.

“I was doing weekly market wraps with local agents, I was interviewing people and I started my own podcast.

“When I first started, I’d get a few views on a video, but quickly, because a lot of people don’t produce content, that started to compound.”

Jack Henderson

Creating content

When he started Henderson Advocacy, Jack took the same approach and says having an in-house team to produce the content on your own terms is important.

It’s also critical to be yourself and ensure you’re posting often enough to gather attention.

“Content is a volume game,” Jack advises.

“Posting one bit of content every six months that no one cares about won’t work. You’ve got to build it up.”

Jack says the best content focuses on either education, entertainment or a combination of both. 

It’s also relevant and authentic.

“The majority of my content is education content,” Jack says.

“I’m talking about things we’re doing for our clients, successes, failures, what I’ve learned and what we’re seeing in the market.

“And you’ll notice none of my content is me wearing a flashy suit, walking through a property, which adds no value to anyone’s life.”

Jack says sometimes people focus too much on making a video “glossy” and forget that it’s consistency, being relevant and adding value to people’s lives that generate brand awareness.

He posts between 10 and 20 pieces of content a day across Instagram, TikTok and Facebook, and while there are tens of thousands of followers on those channels, Jack says posting is not just about getting comments and likes.

“People following you is one metric to thinking how well you’re doing… but in real life, there are a lot more people that know who I am than people who follow me,” Jack explains.

“It’s less about how many likes you get on a piece of content or how many comments you get and more about just knowing that the more you’re in people’s faces, and the more we’re adding value to people’s lives, the more that will spread.”

A unique selling proposition

Since opening its doors, Henderson Advocacy has grown to comprise a team of about 25 people at two physical offices and two satellite branches.

Jack notes that awareness of buyers’ advocates and what services they offer has increased a lot over the past few years, especially as Australia’s property market has become more expensive and more complex.

“I think people are really starting to grapple with the fact that you’re paying for professional advice, and you’re paying to achieve a better outcome than what you would have been able to achieve on your own,” he says.

Henderson Advocacy’s clients are pretty evenly split between investors and owner-occupiers, and Jack says the agency’s unique selling proposition is that their experts come from a place of personal experience as well as professional knowledge.

“I think that for the investment side, our point of difference is the fact that we practise what we preach,” he says.

“If you want to grow a multi-million-dollar portfolio and you want to buy the right assets in the right locations and be able to supercharge your growth, we’ve done it.

“My head of investment Frank Raiti has a $15 million portfolio and I’ve got a $25-ish million portfolio, so we’re people who are actually doing it as opposed to people who are just advising on it and then haven’t done it for ourselves.”

Jack says Henderson Advocacy’s Flamingo Investment Strategy, which is to buy properties that stand out from the crowd, is another key difference the agency offers.

“Then in our owner-occupier division, we’ve developed proprietary software, which we built in collaboration with JLL, which is our advantage sourcing software, which allows us to identify opportunities and source the right opportunities for our clients,” he says.

Working with agents

Jack hopes to see the number of transactions involving buyers advocates in Australia rise from about 2 per cent to 25 per cent in the coming years.

He notes there are several benefits for both buyers’ advocates and real estate agents of working together.

“Especially in the current market, where a lot of buyers are flaky and they’re not committing to transactions, agents know that if someone’s paid a retainer to work with us and they’re a paying client, then there’s a much higher chance that they’re going to transact that just a normal buyer out there in the marketplace that’s not being represented,” Jack says.

He says agents also often have buyers miss out on properties and being able to refer them to a trusted buyer’s advocate who can service them also reflects well on the agent giving the referral.

The rental crisis

Jack is often called upon to give industry commentary, and at the moment, the rental crisis is a very hot topic.

But he notes that it has always been tricky to find a rental property in Australia and the crisis is not new.

“It’s never been easy to find a rental,” Jack says.

“There’s always been a lot of competition and in every market cycle, when it becomes more expensive to buy, people then tend to rent and vice versa. 

“Over the last three years, everyone has been buying and now it’s become expensive to buy, and there’s negative media around buying, so everyone wants to rent.”

When looking at weekly rental rates, they have increased recently, but when you look longer term, those increases even out.

Jack advises tenants struggling to find a rental property to use the services of a renter’s advocate to make the process more straightforward and much less stressful.

The future

Looking forward, Jack has big plans to continue Henderson Advocacy’s growth trajectory, with new offices planned along the east coast.

“Our goal is for Henderson Advocacy to be the largest advocacy firm in Australia within the next five years,” he says.

“My goal is to improve the industry and bring buyer’s advocacy to the forefront of the majority of real estate transactions in Australia.”

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Kylie Dulhunty

Kylie Dulhunty is the Editor at Elite Agent.