Handpicked with Naomi Simson

When you're creating an entirely new category, you can't just sell—you have to educate. Kate Abrahams, founder of TrafficAI (a platform that predicts reputational risk events using workforce behavioral data), sits down with Naomi Simson to discuss the exhausting gap between building groundbreaking technology and getting customers to understand why they need it. Drawing on her experience launching RedBalloon when "experience gifting" wasn't a thing, Naomi shares battle-tested strategies for market development: how to look bigger than you are, turn customers into your sales force through case studies, and build authority when nobody knows your category exists. Kate and Naomi explore keeping tech teams energized during years of customer education, what investors actually need to hear about new categories, and how to cut through the AI hype to demonstrate real value. If you're building something genuinely new and struggling to reach customers who don't yet know they need you, this conversation offers practical frameworks for building customer reach and turning an interesting idea into a must-have solution. Thank you to Deel.com for supporting Australian business owners through it's sponsorship of Handpicked Season 6 for more information about Anytime Pay click hereSee omnystudio.com/listener for privacy information.

What's slowing your business down could become your biggest competitive advantage. James Yang, founder of Kaizen Solutions (a productivity suite for remote teams), asks Naomi Simson the hard questions every Australian startup founder faces: why do our businesses fizzle while American companies scale globally? How do you shift from selling to individuals to landing corporate clients? When do you stop competing and start acquiring? Naomi delivers game-changing insights drawn from 20+ years scaling RedBalloon: stop buying customers one by one and build distribution partnerships instead, transition from throwing people at problems to building platforms that scale, and most powerfully—identify your biggest constraint and weaponize it. She shares how 1-800-GOT-JUNK cornered the market by pre-buying their truck supplier's entire production, preventing competitors from copying them, and how RedBalloon locked up Australia's best experiences before a billion-euro competitor could enter the market. If you're struggling to scale, burning cash on customer acquisition, or wondering whether to compete or consolidate your market, this conversation offers brutally practical frameworks for turning limitations into competitive moats. Thank you to Deel.com for supporting Australian business owners through it's sponsorship of Handpicked Season 6 for more information about Anytime Pay click hereSee omnystudio.com/listener for privacy information.

Strategy is easy. Execution is where most businesses fail. In this episode, Naomi Simson sits down with Mat Wilk, founder of Ballast Point Construction and creator of the Inner West Tech & Startup community, to tackle the challenges every entrepreneur faces: how to move from planning to doing, how to build partnerships that actually work, and whether being a polymath helps or hurts your business growth. Mat shares his belief that businesses spend too much time perfecting strategy when they should be building their execution muscle and creating feedback loops. Naomi counters with practical frameworks including the one-page strategic plan, how to work backwards from big goals to daily actions, and why focusing on one hard thing makes everything else easier.  If you're juggling multiple projects, struggling to get others committed to your vision, or wondering whether your diverse interests are diluting your personal brand, this conversation offers honest, actionable advice for finding focus and getting things done. Thank you to Deel.com for supporting Australian business owners through it's sponsorship of Handpicked Season 6 for more information about Anytime Pay click hereSee omnystudio.com/listener for privacy information.

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 for aging parents and dependent children. Discover why the biggest business opportunities lie in solving nation-building challenges in healthcare, education, and housing. Learn how to build thought leadership and authority in your industry, why celebrating customer wins matters more than self-promotion, and Mark's surprising next venture into solving housing affordability. Thank you to Deel.com for supporting Australian business owners through it's sponsorship of Handpicked Season 6 for more information about Anytime Pay click here  See omnystudio.com/listener for privacy information.

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 system-poor. Learn the triggers that signal it's time to invest in getting your time back—and discover the practical tools that make it possible. Thank you to Deel.com for supporting Australian business owners through it's sponsorship of Handpicked Season 6 for more information about Anytime Pay click here  See omnystudio.com/listener for privacy information.

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 every startup needs, how female founders can stop self-limiting, and the personal planning framework that prevents founder burnout. If you're struggling with business focus, work-life balance, or knowing which customers to turn away, this entrepreneur advice will transform how you think about scaling your Australian business. Thank you to Deel.com for supporting Australian business owners through it's sponsorship of Handpicked Season 6 for more information about Anytime Pay click here    See omnystudio.com/listener for privacy information.

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 ourselves? Amy asks the questions retail leaders are wrestling with right now—and the answers aren't what you'd expect. How do you move from corporate to founder to investor? What should you outsource when you're trying to do it all? And what does Naomi look for in leaders she backs? Naomi shares the conversation that made her realise she needed help, why she and her husband make a plan each year, and the moment she knew her angel investing days were over. Plus: the untapped opportunity in Australian retail over the next few years. It's not what most retailers think—and it can't be put in a box. This episode is for anyone juggling impossible loads, wondering if there's a smarter way to do it all, or questioning what the next chapter looks like when you've already achieved what you set out to do.See omnystudio.com/listener for privacy information.

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 I even start? What networks matter? How do I build trust when nobody knows who I am? And then the big one: What's keeping Australian leaders up at night right now? Naomi doesn't hold back. She shares the phone call that changed everything for RedBalloon ("How do I know you're real?"), why she wears red every single day, and the networking mistake most people make when building a business. Plus: the truth about burnout that went viral on LinkedIn, why leaders are struggling with a completely new set of pressures (AI, cybersecurity, remote teams), and the "tiger team" approach that's replacing traditional org structures. And when Liam asks how to get partners to work harder for you than anyone else? Naomi reveals what she has seen work successfully. This episode is for anyone who's ever felt like they're starting over—whether you're new to a market, rebuilding after a setback, or just trying to figure out where your people are.See omnystudio.com/listener for privacy information.

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 scale? Cara asks the questions keeping service business CEOs up at night: How do you stand out in a global marketplace when you're suddenly competing worldwide? Can you turn custom expertise into scalable products without losing your magic? And how do you test international markets—especially for their niche in member-based organisations—without taking your eye off the Australian ball? Naomi doesn't hold back. She reveals the partnership model that took a  Shark Tank investment global fast. Plus: the warm referral strategies that crack international markets (spoiler: ditch the cold calling) and why tapping into global associations through your existing clients is pure gold. If you're wrestling with taking custom work global, this episode is your playbook.See omnystudio.com/listener for privacy information.

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 1 million to 5 million without losing what makes you special? In this episode, Naomi tackles Oliver's tough questions: building a memorable brand in an "invisible" industry, navigating the leadership shifts required for multi-location growth, and whether to plan for acquisition now or later. From AI-powered scheduling to strategic partnerships and the power of a well-branded van, this conversation is packed with actionable advice for any service-based business looking to scale. Plus, discover why being someone's first customer sometimes comes back to you in the best way possible. NaomiSimson.comwww.professionalpicturehanging.com.au See omnystudio.com/listener for privacy information.

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 Print BarSee omnystudio.com/listener for privacy information.

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 genuine connections in an increasingly digital world.See omnystudio.com/listener for privacy information.

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.

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.

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?See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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  See omnystudio.com/listener for privacy information.

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 ItSee omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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 to motivate today’s sales teams  to how to build a culture of recognition that lifts everyone — not just the loudest voices. These are the kinds of questions that cut through the noise. No fluff — just real, actionable insights for anyone growing a business, leading a team, or simply trying to get the best out of their day. Each episode is short, sharp, and packed with ideas you can use immediately. Because sometimes, all it takes is a new perspective — and a little courage to ask. Join me every Monday for Handpicked. Naomi xSee omnystudio.com/listener for privacy information.