Why Honesty is at the Centre of Harry Kalligeros Approach to Business Sales
Why Honesty is at the Centre of Harry Kalligeros Approach to Business Sales
When a business that had been listed but not sold for 18 months by a previous agency, was sold by Harry in just four weeks (and for more than its original appraisal), it marked a turning point for Perth broker Harry Kalligeros.
It wasn’t just a strong result. It was proof that a relationship-led, disciplined process could succeed in a crowded market. “Honesty sells,” Harry explained. “We go to market for a fair price and aim for a win-win.”
That deal, which has since generated further referrals, reflects a broader pattern that steady growth built on trust and consistency combined with a willingness to do things differently.
Early Career Foundations
Harry’s path into business broking began with a solid foundation in financial planning. He completed a double major in economics and finance at Curtin University before working for a Big 4 bank in the 1990’s. That experience, however, left him disillusioned.
“The bank was all about churn and not really looking after their customers,” Harry commented, reflecting on a culture that would later be the focus of a Royal Commission.
Seeking a more client-focused direction, he transitioned into investment consulting and property, particularly around self-managed super fund (SMSF) structures, following the 2009 legislative changes.
That period saw him working across project marketing and commercial property, including off-the-plan projects and expat clients.
Turning Point Moments
A serious health scare forced an unexpected pause as he nearly lost his life, before making a full recovery. This experience reshaped his outlook and career trajectory.
Returning to work, he joined a commercial real estate company, focusing exclusively on commercial rather than residential property. And then came a pivotal comment.
“My boss said, ‘You’re wasted in commercial. You should be doing business broking.’ And that’s how it all started,” Harry recalled. Seven years on, that was excellent advice.a
Building a Practice
Harry now operates as a business broker alongside his business partner, Trevor, supported by off-site assistants and a highly automated digital process. The practice has grown quickly, at one point accumulating 20 listings in a short period.
Much of that momentum is driven by strong referral networks, including mentorship connections that continue to provide opportunities. “I don’t have any issue generating new business,” Harry noted. “Between my contacts and referrals, it flows.”
Rather than specialising in a single sector, Harry describes himself as a generalist. This allows him to work across a wide range of industries, although he remains selective about the types of businesses he lists. That selectivity is part of his risk management, ensuring he can stand behind the businesses he represents.
He also regards managing vendor expectations early in the process as critical. By being upfront about pricing and timelines, he reduces misunderstandings later.
A Relationship-Led Model
Central to Harry’s approach is a deliberate emphasis on relationships over transactions. “I actually follow the typical financial planning process of appointments and meetings, with the emphasis on ‘know your client, know your product’,” Harry commented.
Unlike many brokers, he avoids leading with financial questions. “Most agents ask for turnover and profit straight away,” he explained. “I don’t do that. I meet them first, explain the process, and ask for financials later.”
This approach serves two purposes. It builds trust early and allows Harry to assist all clients (even if they aren’t sale-ready yet). In some cases, he has provided guidance without charging a fee, preferring to ask for referrals in return.
“I say, tell your accountant what I’ve done, and refer me if you know someone needing a broker,” he remarked.
This strategy has paid off, with even clients whose listings didn’t proceed continuing to refer new opportunities. Over time, this has created a network effect in which each interaction can generate future listings, regardless of the initial outcome.
Process and Technology
While relationships are central to Harry’s process, he has embraced technology to streamline delivery. Artificial intelligence plays a practical role in preparing information memorandums and marketing material.
“I get clients to send relevant dot points, I put that into AI, and it generates the whole document in seconds,” he explained. “Then I use that to generate a short version for the marketing.”
His CRM system further enhances efficiency, automating confidentiality agreements and providing buyers with secure access to business information via an online portal. The system also tracks engagement, offering insights into buyer behaviour.
This information allows him to respond strategically by identifying serious buyers earlier and tailoring follow-up. It also reduces administrative friction, allowing more time for client interaction.
Despite this, Harry is clear that technology cannot replace the human element. “Business broking is all about relationships,” he stated. “I don’t think we can be replaced by AI.”
Standout Deals and Discipline
The four-week sale that exceeded expectations is a standout example of Harry’s disciplined approach. Previously, the business had struggled to attract buyers, but a combination of realistic pricing and transparent communication led to a different outcome.
“I talk to my sellers about aiming for a win-win,” he emphasised. “We don’t want issues after settlement.”
This philosophy extends to valuation. While capable of calculating EBITDA himself, Harry supplements his analysis with data from a national valuation firm. This allows him to justify his appraisals with greater authority.
This disciplined approach extends beyond pricing to deal management. By setting clear expectations with both buyers and sellers, he reduces the risk of failed negotiations or settlements.
Market Realities in WA
Operating in Western Australia presents unique challenges, particularly at the smaller end of the market. The state’s strong Fly-in, Fly-out employment opportunities can make business ownership less attractive.
“If someone can earn $150,000 in a mine, why buy a business for $300,000 that makes the same?” Harry asked.
As a result, he looks for businesses with stronger earnings, typically requiring higher EBITDA levels to attract buyers. This situation underlies the advice he gives to potential vendors.
Buyer preferences are also changing. Many are now seeking businesses that can operate under management rather than requiring hands-on ownership. Harry recently worked with a buyer who owns 21 businesses, each operated by trusted managers.
This trend reflects a broader move to scalability and a portfolio-style approach in which systems and teams are as important as the underlying businesses.
Looking Ahead
For Harry, the future of business broking lies in refining service, not reinventing it. Professionalism and transparency remain critical differences in an industry where standards can vary.
“There are cowboys everywhere,” he candidly commented. “The whole service offering needs to be very professional.”
His own model, combining a structured process with personal engagement and the smart use of technology, positions Harry for continued growth. With a strong referral network and a reputation for delivering win-win outcomes, he is building a brokerage that reflects his background and values.
In a market shaped by economic cycles and changing buyer expectations, that balance may prove to be his defining asset.
About the author
