Hall of Fame New England Patriots NFL Quarterback Drew Bledsoe sits down with Simon in this episode of Hallers Playbook to discuss the dynamics of rugby and NFL, the challenges of franchise systems, player safety, and the transition from professional sports to the wine industry. They explore the importance of sustainability in wine production and the lessons learned from sports that can be applied to business, particularly the value of embracing adversity and maintaining authenticity in athlete-driven brands.

• (00:00:00) - Haller's playbook
• (00:00:51) - Wonders of London
• (00:05:59) - Adam Levine on His NFL Career
• (00:09:44) - Tom Brady on Life After Playing Football
• (00:17:10) - Drew Brees and Tom Brady in the Wine
• (00:22:05) - Tom Brady on Being the No. 1 Pick in the NFL
• (00:26:37) - Adversity in the Business
• (00:34:22) - Does NFL Franchise Stifle Competition?
• (00:39:18) - Rugby and head injuries
• (00:45:24) - Borrello CEO on Continuity

In this engaging conversation, Simon Halliday interviews Jill Douglas, a prominent sports broadcaster, about her experiences in the world of sports media, the evolution of women's roles in broadcasting, and the growth of women's sports. They discuss the challenges and opportunities in women's rugby, the dynamics of covering major sporting events, and the impact of charity work, particularly in relation to Doddie Weir and the My Name's Doddie Foundation. Jill shares her insights on bridging the gap between sports and business, emphasizing the importance of storytelling and the transferable skills gained from sports broadcasting.

• (00:00:00) - Haller's playbook
• (00:01:24) - Summer Sport Commentation
• (00:05:58) - The story of Lorraine Ferguson
• (00:10:43) - The Sunday Times Sportswoman of the Year interview
• (00:16:28) - Mismatches in the Women's Rugby
• (00:19:28) - Do You Have To Do Your Homework For the Olympics?
• (00:26:28) - The Big Moments on the BBC
• (00:30:40) - Simon Gallagher's role in the business of sport
• (00:37:39) - The Doddy Foundation
• (00:45:59) - A busy week for sport on the BBC

• (00:00:00) - Haller's Playbook
• (00:08:26) - The challenges of compliance in the financial services industry
• (00:14:00) - Challenges for Crypto and Tokenization
• (00:16:43) - The challenges of compliance at a small firm
• (00:19:39) - Small Businesses and Compliance
• (00:25:51) - Mass Financial Group's growth and compliance
• (00:33:32) - The core competence of a business

• (00:00:00) - Haller's Playbook
• (00:00:40) - Top Horse Trainer in Australia on Horse Races
• (00:01:53) - Tony Trainers first win in 1999
• (00:06:40) - England vs Australia
• (00:08:35) - Racehorse trainer and
• (00:15:24) - Racehorse finance, prize money
• (00:17:00) - Temple of Boom
• (00:18:31) - The secret to racing's riches
• (00:20:36) - Talking About Horse Racing's Future
• (00:23:01) - The Horse Training Team
• (00:24:49) - Queensland trainer Darren Ferguson on his ambitions

Rugby World Cup winner, trailblazing coach, and one of the most influential voices in the women’s game – Giselle Mather joins Simon on Hallers Playbook this week.

From the grassroots explosion of participation to the spotlight of the recent World Cup, Giselle reflects on the huge strides the women’s game has made – and the hurdles it still faces. She speaks openly about the structural and financial challenges, the ongoing fight for visibility and investment, and why developing the next generation of players is crucial to sustaining momentum.

Simon and Giselle also discuss the cultural shift rugby is undergoing, how women’s rugby is redefining the values of the sport, and what needs to be done to ensure that progress doesn’t stall.

One thing is clear: for women’s rugby to fulfil its potential, the game must embrace its pioneers, build pathways that match ambition with opportunity, and commit to making the sport truly global, inclusive, and sustainable.

In this episode of Hallers Playbook, Simon Halliday sits down with MAS Group Head of APAC Harry Fry and explore Harry's journey from playing rugby in England to working in financial markets in Australia. The conversation also touches on the rise of digital assets in finance and the growing recognition of women's rugby. Harry shares valuable advice for aspiring rugby players about having a backup plan and the significance of life after sports.

Some of the takeaways from the podcast:

• Australian rugby is experiencing a resurgence with recent wins.
• The Women's Rugby World Cup is a significant event for women's sports.
• Rugby union in Australia is still seen as an upper-class sport.
• Teamwork in sports translates well to the financial industry.
• Digital assets are becoming increasingly important in finance.
• Smaller financial institutions offer more personalized service.
• Moving to Australia provided new opportunities for Harry Fry.
• Aspiring rugby players should always have a plan B.
• The women's game is gaining recognition and support in Australia.
• The future of rugby looks promising with growing interest in women's competitions.

• (00:00:00) - Haller's Playbook
• (00:02:01) - What's the feeling towards Australian rugby?
• (00:05:05) - Harry Kane on playing for Blackheath Rugby Club
• (00:13:05) - Rugby is not for everyone
• (00:15:50) - MAS on the Future of Digital Assets
• (00:17:00) - What's the Risk of Digital Assets?
• (00:18:17) - Have We Reached a Smaller Brokerage?
• (00:19:56) - In the Elevator With Mass Group's Harry Blackledge
• (00:21:34) - Tom Farrell on the future of amateur rugby
• (00:26:23) - England vs Australia