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 here

See 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 here

See 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 here

See omnystudio.com/listener for privacy information.