They Say I Dream Too Big. I Say They Think Too Small!
Annah Stretton is one of New Zealand’s most enduring and unconventional business success stories. A fashion designer, social entrepreneur, podcast host, author, and three time Master’s graduate, Annah has spent nearly 35 years proving that reinvention is the key to staying relevant.
Starting her fashion business from rural Morrinsville in 1991, Annah built the Stretton Clothing Company brand into a nationally recognised label that, at its peak, operated 42 stores across New Zealand. Today, the business has successfully evolved into a modern digital first brand with a strong online presence and a growing focus on accessories, homeware, and lifestyle.
Known for combining creativity with commercial grit, Annah openly speaks about surviving the brutal realities of retail, adapting through economic downturns, and pivoting hard when others closed their doors. During COVID, her business famously reinvented itself through large scale mask production, helping stabilise the company during one of retail’s toughest periods.
But Annah’s story extends far beyond fashion.
Alongside business, she has become one of New Zealand’s most recognised voices in social impact and prison reform through RAW, the organisation she founded to support incarcerated and high risk women. Her work inside New Zealand women’s prisons, including the operational delivery of constructive activities at Rangiora Waikeria Prison, has helped reshape conversations around rehabilitation, education, identity, and reintegration.
Returning to university in her late 50s, Annah completed three Master’s degrees in Social Policy, Māori and Indigenous Studies, and Photography, using academia to strengthen the practical social change work she was already leading on the ground.
Annah was recognised as a New Zealander of the Year finalist in 2018, 2019, and again in 2026, adding to a long list of accolades that includes the New Zealand Order of Merit, EY Social Entrepreneur of the Year, and Veuve Clicquot Businesswoman of the Year.
She is also the founder of Olive's Kitchen, Fish Digital, and Hopefish, while continuing to lead the rapidly growing Sisterhood Social platform, designed to combat loneliness and create meaningful female connection for women over 40.
As co host of the Stretton Unfiltered podcast, Annah is known for her raw, intelligent, and often provocative conversations around business, ageing, relevance, prison reform, entrepreneurship, resilience, and social change.
What makes Annah such a compelling speaker is not just her success. It is her ability to constantly evolve. At an age where many people retreat professionally, Annah continues to launch businesses, complete degrees, build movements, challenge systems, and remain culturally relevant in industries where most brands disappear.
Talking Points
Leadership: The Secret to Surviving and Thriving in Business
Having survived 30 years in the fashion industry, Annah's leadership journey is a powerful narrative about disruption and continuous reinvention.Leadership: The Secret to Surviving and Thriving in Business
From her start-up days as a wholesaler to New Zealand fashion chain stores, to the successful designer, manufacturer and nation-wide retailer that she is today, Annah knows what it takes to survive and grow through all stages of the business cycle. But it didn't stop there. An entrepreneur well known for both her business acumen and her philanthropic heart, Annah set up her own foundation in 2013 as part of her succession plan. This enabled Annah to identify new challenges and look for new solutions for some of New Zealand's more pressing social and fiscal problems.
Annah's widely recognised achievements in the social ventures space once again showcase her ability to connect, lead and empower through new thinking and adaptive processes.
Heart: Generating profit with a purpose
Right from the beginning, Annah has been an active supporter and contributor to many of New Zealand's well-loved charities. Back in 2013, however, Annah took her philanthropy to a whole new level with the establishment of the Stretton Foundation as a vehicle to drive social change. It was time to take advantage of all that the fashion industry had taught her to generate real outcomes for some of New Zealand's largest challenges.Heart: Generating profit with a purpose
Her first social venture was RAW (Reclaim Another Woman) which is focused on breaking the cycle of intergenerational disadvantage by helping female offenders transition from a life of crime to a life of promise through education, employment and intensive peer support. Her second, Kia Puawai, is focused on redefining the road to better health and wellbeing in the workplace, and in the community, by introducing simple, seamless and sustainable edits to your lifestyle. Her third, Hope Fish, which focuses on building a solidarity structure that delivers real opportunity, inclusion, and support to socially disadvantaged wahine and their tamariki.
Annah's story is one of success and failure, trial and error and disruptive and adaptive leadership, as she challenges the status quo and embraces new normals to drive social change in this country.
Video
Annah Stretton Show Reel
Every so often you will find that someone' who - when asked to fulfil a showcase speaker opening slot, or an outstanding grand finale to your event - not only rises to the occasion, but ooze ... keep reading RISE EVENTS
Over my past ten years in New Zealand I have had the pleasure of working alongside some brilliant entrepreneurial minds, however, never I have met with someone who takes such a refreshing and untapped approach as Annah does. Her extraordinary zest and dedication are quite profound and infectious; once you've heard her speak, your mind will be on overload - your energy invigorated.
The best speakers are the ones who not only inspire but who empower us through their words - leading us with passion from whatever position we may currently hold in life. We all know that a charismatic speaker leaves an impression on the audience, large or small, that makes them want to come back for more: Giving nothing other than the 150% (as she does in all of her life and business endeavours), Annah does this by the bucket load!
Annah provided us with an outstanding key note address for our conference. Her sharp mind and her business acumen was strongly evident and very inspirational for our audience. It is not an exaggeration to say that everyone was hanging off her every word for the whole of her presentation. After she left, many people commented to me that they wanted more time to ask questions, further proving the extent to which she engaged the audience. Annah also did a fantastic job at crafting her presentation so that it paired perfectly with the topics we had asked her to talk to and which were relevant for our audience. Annah's story is fascinating and her presentation for us was top knotch.
Interest generated about RAW (Reclaim Another Woman) at the presentation given by Annah Stretton to Women on Boards New Zealand Waikato last night was overwhelming.
We were very impressed with Annah Stretton's enthusiasm, communication skills and presentation skills when she recently talked to students enrolled in Applied Fashion Design and Technology at the Fashion Industry training services department of TAFE in South Australia. During the presentation, Annah consistently demonstrated a thorough knowledge of fashion retail, fashion production and how to run a successful business. ANNAH'S DEDICATION TO HER CRAFT AND TO MENTORING OTHERS WAS INSPIRATIONAL TO BOTH LECTURERS AND STUDENTS. We look forward to a continued association with Annah and are sure that both students and staff will benefit from the relationship.
We had the absolute pleasure of Annah Stretton addressing the Newmarket Rotary Club earlier this year to educate our members about the RAW programme. She a confident and passionate speaker and what she and her team are achieving with vulnerable and abused women is nothing short of outstanding. A great nationwide support initiative is something that really resonates with Rotary
