In an exclusive interview with APAC Entrepreneur, the distinguished entrepreneur shared his fascinating entrepreneurial journey.
Garry Winter, Co-founder, WRP Legal & Advisory
Law has long been associated with caution, with identifying gaps, weighing risk, and carefully explaining what could go wrong. Yet for businesses operating in real time, a carefully articulated problem is only the beginning. What they need is perspective. They need advisors who can cut through complexity, bring clarity to the table, and shape decisions with confidence. For Garry Winter, that responsibility has always been central to his practice.
He stepped into the legal world with one clear purpose: to solve problems. It is that very satisfaction—the ability to work through a client’s most complex issues and deliver resolutions that truly make a difference—that has kept him committed to the profession for more than three decades. He treats his clients’ challenges as his own, approaching each matter with urgency, accountability, and a determination to deliver outcomes that are not just legally sound but strategically and commercially significant.
Garry did not grow up intending to become a lawyer. With both his father and older brother established as chartered accountants, a career in accounting seemed the natural path. He began studying law to strengthen his qualifications and broaden his prospects within that field, but soon found himself drawn to the discipline. What appealed to him most was its focus on problem-solving for people. It required analytical discipline, but also judgement and creativity. Once he began practising, his background in accounting naturally complemented his legal work, leading him to specialise in taxation law.
The more complex the issue a client brings forward, the more motivated he becomes to find an acceptable and practical solution. “As markets globalize and technology reshapes industries, the role of legal advisers has become even more critical, and this is not something that will ever be replaced by technology such as AI. The ongoing challenges, combined with the ability to make a tangible impact, are what continue to drive my commitment to the profession,” shares Garry.
In 2014, Garry and his two founding partners launched WRP Legal & Advisory in Adelaide with one clear principle: never identify a client’s problem without committing to finding a solution. They wanted to create a firm that doesn’t just flag issues but actively helps clients navigate them with clarity, strategy, and confidence. “We consistently saw other lawyers in our industry who considered that their job was simply to identify problems or issues for their client without feeling a responsibility to find a solution,” Garry recalls. “It was our view at WRP that most clients already knew that they had a problem; otherwise, they wouldn’t be speaking with us in the first place.”
WRP Legal was built around a culture of partnership, where lawyers act as strategic allies, providing concise, practical advice supported by technology that enhances efficiency rather than slowing it down. Entrepreneurship has always been at the heart of WRP. The firm has a long history of supporting innovators and early-stage companies, often structuring fees to suit the formative stages of a business. This strategy has been a huge success for WRP, with many of its early clients who were once small startups now grown into global enterprises with revenues in the billions. In addition to investing in these clients, Garry often takes on independent board roles, guiding these companies through governance, strategic decision-making, and operational processes.
When Garry first started practising law 30 years ago, the profession was paper-driven. Lawyers dictated onto tapes, secretaries typed them up, and clients were content to wait a week or more for a response. Fast forward to today, and the pace has changed dramatically. “Now, if I haven’t responded to an email or call within a few hours, clients are calling my executive assistant or junior lawyers to check if I’m still alive!” Garry laughs.
This immediacy has reshaped the legal landscape, requiring not only talented teams but also the strategic use of technology. At WRP Legal, routine tasks are streamlined through digital tools, automation, and data-driven processes, freeing lawyers to focus on higher-value, strategic advice. The result is faster, more consistent, and value-driven outcomes without compromising quality. For Garry, having a deep understanding of his clients’ businesses and affairs is just as critical. He prioritizes proactive communication, ensuring clients are informed promptly about any changes in the law or legal interpretations that could affect them.
Garry believes that the culture of any organisation is difficult to confine to words. It is more of a feeling and a framework of how a firm operates. At WRP Legal & Advisory, that framework is grounded in trust, accountability, innovation, hard work, and continuous improvement. “We operate in an environment where people are encouraged to think commercially, challenge assumptions, and take ownership of outcomes,” he asserts. “Collaboration is central—both internally and with clients—because the best results come from shared understanding and aligned goals.”
Learning and development are pillars of the firm. All junior lawyers are encouraged to pursue postgraduate study, fully funded by WRP, and practitioners are supported to develop deep specialist expertise in their chosen area of law. WRP also values connection beyond day-to-day legal work. While regulatory changes have made social gatherings more challenging, WRP continues to host numerous events throughout the year, giving staff from directors to law clerks opportunities to build rapport in a relaxed and enjoyable environment. It ensures the team is well-compensated, offering above-market salaries and a structured bonus system that rewards high performers who exceed agreed targets.
For Garry, one of the most defining challenges at WRP Legal & Advisory has been scaling the firm without diluting the very culture and quality that fuelled its early success. “We started with just three people over ten years ago, and now we’re approaching 80 staff across Adelaide, Sydney, and Melbourne,” he reflects.
This journey helped him learn a simple truth: the right people make all the difference. Early in the firm’s development, WRP hired a CEO who was wearing multiple hats—CFO, CMO, HR, and even a handyman. Over time, the firm built a dedicated administrative team with specialists in each key role, allowing the CEO to focus solely on leadership, while still keeping the spirit of hands-on involvement alive.
As WRP continued to evolve, Garry and the founding partners faced another significant hurdle—opening up equity in the firm to leaders outside the founding trio. The process was more complex than Garry anticipated. Yet looking back, he considers it one of the healthiest and necessary steps for WRP’s evolution. Today, the firm boasts a team of exceptional directors who are not only capable leaders but are also set to become the next owners of WRP. “We have some fantastic directors at WRP, and I am very proud that they will be the next owners of the firm. I am confident of the future of the firm when I decide to ride off into the sunset,” he affirms with pride.
Garry’s influence extends far beyond the legal profession. He was instrumental in bringing Techstars to launch its first Southern Hemisphere accelerator in Adelaide, running defence-themed cohorts in 2017 and 2018. As co-founder of Splose, he helped build a platform that was recently valued at $172 million following a $46 million Series A raise led by Spectrum Private Equity and Athletic Ventures. He was also an initial shareholder and chairman of MEQ Probe, which recently secured $50 million from Insight Partners, and remains a significant shareholder and director of Litigation Lending Services, Australia’s largest privately owned litigation funder with a focus on ESG and First Nations claims.
His reach extends across sectors, from early-stage investment in Prezzee to serving on the board of the Adelaide International Equestrian Festival. He is also a co-founder, significant shareholder, and director of WSM and Pickstar. Most recently, he stepped into the music industry, launching a record label with internationally acclaimed singer Conrad Sewell.
Over the next decade, Garry sees WRP Legal & Advisory continuing to evolve as a technology-enabled, strategy-driven legal partner for its clients. The recent launch of the Sydney office marks an important step in that direction. Over the years, a number of high-calibre candidates based in Sydney had applied for roles at the firm but expressed a preference to remain in Sydney. Opening the Sydney office enables WRP to access that talent pool while preserving its collaborative culture. While Garry is mindful that maintaining culture across multiple offices will be one of the firm’s most important challenges in the decade ahead, he sees technology playing an important role in addressing this, particularly through collaborative online workspaces.“We have never set specific long-term growth rates for the firm, but I can see the firm continuing to grow rapidly over the next five to ten years in a manner that meets our clients’ needs and demands,” opines Garry.
To aspiring legal and business entrepreneurs, his advice is disarmingly simple: have a go. Do not be afraid to fail or take a calculated risk. Failure, he believes, is not the opposite of success but part of the process. The key is to analyse what went wrong, learn from it, and rise again with a stronger resolve. He knows there will always be voices explaining why something cannot be done, but he encourages emerging leaders to become the person who figures out how it can be done. “I am a big believer that every problem has a solution (and usually multiple solutions). Sometimes, you need to look at things from a different angle to see the solution, but don’t give up at first instance and keep trying,” he advises.
“Finally, remember that entrepreneurship is a long-term commitment,” he adds. “A failure simply offers an opportunity to learn and refine your approach.”