Handpicked with Naomi Simson

Handpicked with Naomi Simson

Handpicked with Naomi Simson is a short podcast delivered each Monday which is just like having a mentoring session with one of Australia's most successful entrepreneurs. In this podcast Naomi takes questions from business owners that might need help growing starting or saving their business. Each guest is handpicked by Naomi as she shares stories, ideas and advice that might help them and anyone that has ever wanted to start a business. Naomi Simson is an entrepreneur who founded RedBalloon in 2001. She has been blogging for a decade at NaomiSimson.com, is a professional speaker, author of Live What You Love & Ready To Soar, and a “Shark” on business reality show Shark Tank Australia.

Episodes

February 22, 2026 16 mins

Every successful business starts with a problem worth solving. In this episode of Handpicked, Naomi Simson sits down with Mark Woodland, founder of Kismet, who's tackling one of Australia's biggest challenges: the administrative burden crushing families caring for aging parents. After successfully building and selling Explore, Mark is now automating healthcare admin for the "sandwich generation"—those caught between caring fo...

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Time is your most precious resource—so why are you spending it on admin at 11pm? Naomi Simson and Slavic Teplitsky from Deel reveal exactly how to get your time back. From consolidating 16 time-sucking vendors into one streamlined platform to giving employees instant access to their earned wages (saving everyone's time), this episode is a masterclass in reclaiming hours you didn't know you had. If you're time-poor, you're sys...

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February 8, 2026 18 mins

Every founder says yes too often—and it's killing their business growth. Naomi Simson sits down with serial entrepreneur Sheree Andersen (founder of Elephant and Trove corporate gifting platforms) to reveal the pivotal moment in RedBalloon maturing and learning what to say no to.  Discover why business success comes from what you refuse, not what you accept. Learn business focus strategies, the cost-to-serve analysis eve...

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November 23, 2025 15 mins

Six kids under six. C-suite roles at Australia's biggest retail brands. A law degree completed just to prove her brothers wrong.

Amy Louise doesn't do things halfway.

From shop floor to boardrooms. Amy's built her career scaling iconic Australian retailers while raising six children in what can only be described as controlled chaos.

But here's what she wants to know: Is burnout really a badge of honour? Or are we all deceiving to o...

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November 9, 2025 17 mins

Liam Forde ran a big business in London. His confession? "I turned into an asshole."

So he spent the next 26 years teaching people not to be like him—creating transformation experiences for leaders across 40 countries.

Now he's relocated to Australia for his grandkids—and he's starting completely fresh. No networks. No contacts. No idea where to begin in the Australian market.

His questions are brutally honest: Where do...

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January 2020. New CEO. Six-month-old baby. Seven weeks later? COVID hits.

That's how Cara McLeod stepped into the CEO role at Mahlab—and somehow that chaos became the launchpad for international growth.

But here's the problem: Mahlab does bespoke strategy work. Everything is custom. Every project needs people. More growth = more headcount. The classic service business trap.

So how do you scale what on paper looks hard to scal...

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What do you do when you've built a successful business in a niche that most people don't even know exists? Oliver Lonergan went from selling lollies in primary school to running Professional Picture Hanging—a 12-person operation spanning Australia's east coast and London, with major contracts including Crown Sydney and luxury hotels. At just years out of school, he's facing the classic scale-up challenge: how do you grow from...

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September 7, 2025 16 mins

Join Naomi Simson as she mentors Jash Fullinfaw from The Print Bar through the critical challenges of website re-platforming, scaling print-on-demand operations, and maintaining customer experience during rapid growth. From SEO migration strategies to revenue model prioritisation, this episode delivers actionable insights for any e-commerce business navigating technology transformation while preserving what makes them special.

The ...

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August 31, 2025 21 mins

Join Naomi Simson in conversation with Adriana Brusi, Managing Director of CrowdsNow, as they dive deep into the real challenges of startup life. From the three critical mistakes that derail new businesses to why authentic relationships trump expensive marketing campaigns, this episode reveals the uncomfortable truths about building a business that lasts. Discover why your customers should be your best ambassadors and how to create...

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August 24, 2025 12 mins

Drowning in property management systems, booking engines, and CRM platforms? Alicia Szerszyn from Paradise Resort gets answers on balancing high-tech with high-touch.

See omnystudio.com/listener for privacy information.

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August 17, 2025 16 mins

When tourism gets tough, do you pivot or persist? Mark Garey from Orange Trikes faces three critical decisions about SEO, pricing strategy and premium product marketing.

See omnystudio.com/listener for privacy information.

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August 10, 2025 15 mins

Jay Yip's 40-year tourism journey leads to one big question: as AI transforms travel booking, is it better to go everywhere or focus on fewer, better partners?

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August 3, 2025 16 mins

From tea towels to TV dreams: Live painter Sarah Rowan asks how sole traders can scale without losing their magic. Her energy is infectious and her questions apply to every creative entrepreneur.

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From Crohn's diagnosis to gut health empire: Rudi van der Vlies asks how to build authority, tackle taboo topics, and grow D2C brands in the AI era. Game-changing insights inside.

If this is for you - https://www.brand-hub.au/pages/tumme also use the code NAOMI10 to get a discount

 

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July 20, 2025 20 mins

When 91% of companies have recognition programmes but only 31% rate them as effective, something's clearly broken. In this episode, co-CEOs Belinda and Amie from Cos share how they're revitalising their "tired" recognition programme without falling into the favouritism trap.

Why Strategy Execution Unravels and What to do About It

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July 13, 2025 16 mins

OnDeck's Justin Brady asks the tough questions about sales incentives and customer relationships. Discover why memorable beats monetary and the three pillars that drive results.

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July 9, 2025 1 min

Hello, I'm Naomi Simson — and we’re back with a brand new season of Handpicked, my podcast where real business owners bring me their real questions.

Season five is here (can you believe it?), and wow — the entrepreneurs have really brought the big ones this time. We’re talking about everything from how t...

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August 22, 2023 2 mins

What is your brand promise? 

 

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August 15, 2023 3 mins

In this short extra I look stratergy made simple 

 

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August 13, 2023 18 mins

Venkatesh has been in business for almost a decade and he is really wanting to scale. I ask him to consider the constraints of the business and what is holding him back. He wants to know if being boutique is good and how to appeal to larger customers - as a twist at the end I ask him to dream about what his business will look like in five years time. Do you dream about what is possible?

Don't forget to rate, review and refer Handpi...

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