In this episode of Give It A Nudge, Steve sits down with Tom, co-founder and CMO of Lawpath. They talk about the reality of scaling a legal tech platform to over 600,000 small businesses. Tom shares a staggering statistic: up to 120,000 new companies are registered in Australia every single month. He explains exactly how Lawpath built a system to capture that massive audience.

Starting a business is hard. The standard three-year survival rate sits at a grim 51%. Most founders get completely crushed by the administrative burden of running a company. Tom explains why taking the legal and compliance work off their plates frees them up to actually build their products. This shift has pushed the survival rate of Lawpath users up to 65%. He also walks through their massive $10 million investment from Westpac, and why they doubled down on advertising during the COVID-19 lockdowns while their competitors froze.

We get into Tom's personal story, too. He traces his early career from Spritz—a startup that went through a wild $40 million acquisition by Yahoo7—to learning strict brand discipline at Tom Waterhouse. He opens up about the painful jump from being an individual contributor to a scale-up executive. He even admits that the sudden birth of his first child right before Black Friday finally forced him to stop micromanaging his team. Steve and Tom also trade stories about maintaining an 11-year co-founder relationship, and why loyalty always beats cheap pricing in the Australian market.

Timestamps:

00:00 – Intro: Surviving Spritz’s $40M Yahoo7 acquisition

05:47 – Learning strict brand discipline at Tom Waterhouse

08:31 – The origin of Lawpath: Fixing the headache of business setups

11:48 – Reaching 600,000 customers and the roadmap to 1 million

13:51 – How to secure a $10M strategic investment from Westpac

16:24 – Why 120,000 Aussies register new businesses every month

18:56 – Market quirks: Why Australian clients value loyalty over a cheap price

20:39 – The COVID pivot: Doubling ad spend while everyone else panicked

26:19 – Leadership realities: How a Black Friday baby cured his micromanaging

30:00 – Co-founder survival: 11 years together without imploding

37:01 – The 65% survival rate: Why automating the back-office keeps startups alive

Links:

Connect with Tom → https://www.linkedin.com/in/tomwillisweb/

Lawpath → https://lawpath.com.au/

Connect with Steve → https://www.linkedin.com/in/stevegrace/

The Nudge Group → https://thenudgegroup.com/

Give It A Nudge Podcast → https://www.youtube.com/@giveitanudge/

The Trouble With People → https://thetroublewithpeople.substack.com/

In this episode of Give It A Nudge, Steve sits down with Jacqui Clarke, ex-Deloitte Private Partner and author of Stop Worrying About Money, to talk about the single most important number 95% of people don't know: "What does it cost to open your front door?"

With the cost of living skyrocketing and "inheritance impatience" on the rise, financial stress is no longer just for those struggling to make ends meet. Jacqui explains why earning more money rarely solves a spending problem and why even high-net-worth individuals are terrified of their own bank accounts. She breaks down the "Toyota vs. Porsche" mindset trap and why smart women often find themselves financially vulnerable after a divorce.

Jacqui shares her background advising Australia’s wealthiest families and the brutal reality of the "ghosts" that come out of the woodwork when you leave a major firm. She also opens up about the "Orphan Club"—losing both parents in six months—and how it reshaped her view on legacy. Together, they prove that financial freedom isn't about how much you make, but about clarity, control, and honest conversations.

Timestamps:

00:00 – Intro: Steve’s 15-year history with Jacqui

02:00 – The "Orphan Club": Losing both parents in 6 months

08:00 – The secrecy of money & why families don't talk

12:15 – Divorce & financial literacy: Why smart women get stuck

17:45 – Leaving Deloitte: Bad leadership & the decision to jump

21:30 – The exit: Non-competes and the relief of walking away

24:40 – The "Ghosts": When former colleagues circle back

30:30 – The Big 4 Model: Why the "magic" is fading

36:00 – Writing a bestseller in 12 weeks (The 5am routine)

49:15 – The 95% Stat: Knowing the cost to open your front door

52:10 – The Toyota vs. Porsche mindset for young adults

56:30 – Longevity Risk: Can you afford to live to 100?

58:30 – Closing thoughts

LINKS

Connect with Jacqui → https://www.linkedin.com/in/jacquiclarke/

Stop Worrying about Money → https://www.jacquiclarke.me/stop-worrying-about-money

Connect with Steve → https://www.linkedin.com/in/stevegrace/

The Nudge Group → https://thenudgegroup.com/

Give It A Nudge Podcast → https://www.youtube.com/@giveitanudge/

The Trouble With People → https://thetroublewithpeople.substack.com/

In this episode of Give It A Nudge, Steve sits down with Jevon Le Roux (CEO) and Tahir Rauf (CTO), co-founders of Keeyu, to talk about the single most expensive question in e-commerce: "Where's my order?"

With 40% of all support tickets relating to delivery status and 56% of customers churning after just one bad post-purchase experience, the stakes have never been higher. Jevon and Tahir explain how they built a system to monitor 28 different failure points across fragmented software systems. This moves the industry from reactive resolution to proactive prevention.

The results? A massive 90% reduction in complaints and a 29% drop in workforce costs for their pilot customers.

Jevon shares his background in high-pressure retail ops where he saw teams spending half their day manually searching for orders. Tahir breaks down the technical challenge of connecting a "spaghetti stack" of legacy systems. Together, they are proving that while it takes 4 hours to fix a problem, it only takes 1 hour to prevent it.

Timestamps:

• 00:00 – Intro: The 56% Churn Stat & The Where’s My Order Nightmare
• 01:58 – Jevon & Tahir’s background: From Fintech & Retail to Founders
• 06:58 – The Problem: 28 failure points across 8 different systems
• 08:35 – How Keeyu Works: Moving from Reactive to Proactive
• 12:00 – The “4 Hours vs 1 Hour” Efficiency Rule
• 15:15 – It Can’t Be Done: Tackling the integration spaghetti
• 18:15 – The Pilot Results: 90% less complaints, 29% lower costs
• 21:00 – Raising Capital & The Plug-and-Play Architecture
• 34:00 – Steve’s horror story (and why manual support is dying)
• 38:15 – Services as Software: Redefining the industry standard
• 40:00 – The Founder Dynamic: Why Jevon said “I’m in” in one second
• 42:50 – Closing thoughts

Links:

Connect with Jevon → https://www.linkedin.com/in/jevonleroux/

Connect with Tahir → https://www.linkedin.com/in/tahirrauf/

Keeyu → https://www.keeyu.com/

Connect with Steve → https://www.linkedin.com/in/stevegrace/

The Nudge Group → https://thenudgegroup.com/

Give It A Nudge Podcast → https://www.youtube.com/@giveitanudge/

The Trouble With People → https://thetroublewithpeople.substack.com/