Brendan Malone, CEO of Raiz Invest, joins Dexter Cousins to mark 10 years since Raiz launched to Australian retail investors. From a joint venture with US micro-investing app Acorns in 2015, Raiz has grown to $2.1 billion in funds under management, over 330,000 active monthly users and over $5.5 billion invested for Australians.

What We Discuss

• How Raiz started as a joint venture with US app Acorns in March 2015 before listing on the ASX as Raiz in April 2018
• The roundup innovation that put $2.2 billion to work for 340,000 Australians through small amounts consistently over time.
• Why Raiz expanded into Southeast Asia, the 280 million person opportunity in Indonesia and what made it harder than expected
• The ASX listing as a capital strategy when VC appetite for fintech was thin in 2018
• Brendan's frustration with CDR after a decade of roundtables, policy submissions and no meaningful consumer outcome
• How a 42-person team manages $2.2 billion using AI and machine learning, and why Brendan would not start again from scratch even in the AI era
• Raiz's product roadmap including the Raiz Kids ecosystem and why Brendan expects consolidation among micro-investing platforms within the next few years
• The endurance principles shared by Australian fintechs that have survived a decade: stay close to customers, resist the bright shiny things, and stick to the strategy

Key Timestamps

01:00 Celebrating a Decade in Business
02:11 The Genesis of Raze and Early Challenges
05:13 Breaking Down Barriers to Investing
08:08 Innovative Wealth Management Solutions
10:49 Growth Plans and Market Strategies
13:18 Exploring Southeast Asia's Market Potential
15:50 The Scale Game: Financial Inclusion in Indonesia
18:28 Lessons from Early Adopters: The CDR Experience
19:51 Navigating Regulatory Challenges in FinTech
23:04 Customer-Centric Innovation: Listening to the Market
24:19 The Impact of AI on Business Transformation
28:21 Building an Ecosystem for Sustainable Growth

Links and Resources

• Raiz Invest: raizinvest.com.au
• Brendan Malone on LinkedIn
• Tier One People: tieronepeople.com

This show is brought to you by Tier One People, where we work with founders like Brendan to find the 1% who redefine what's possible. If you're scaling your leadership team, start at tieronepeople.com.

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David Hyman co-founded Lendi Group in 2013 and built it into Australia's largest non-bank mortgage platform with a $107 billion loan book, 5 million customers, and $350 million in annual revenue. He stepped down as CEO in January 2026 and within weeks was building his next company.

In his fourth appearance on Fintech Chatter, David joins Dexter to talk about Mono AI, a platform business that helps established companies become AI native before a leaner AI native competitor makes them irrelevant.

They cover the difference between human motion and agentic motion, why the CTO is often the biggest blocker to AI strategy, what ElevenLabs's $2 million revenue per employee tells you about the next three years, and the two traits (curiosity and high agency) that separate people who will thrive in this transition from those who won't.

David also explains the Mono AI wedge model, why he's building a global AI business from Sydney, and what roles the company is actively hiring for now.

This episode was recorded just before the major job losses at Block and Atlassian. It is one of the most practically important conversations on this show to date.

Find David on LinkedIn or visit monoai.co

Tier One People: tieronepeople.com

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Block Just Cut 4,000 Jobs. WiseTech Cut 2,000. Here's What To Do Next.

Last week was a wake-up call for anyone working in fintech and tech in Australia.

Block — the company behind Square, Cash App, and Afterpay — cut more than 4,000 employees. That's nearly half the company, down from over 10,000 to just under 6,000. The stock surged 24% on the same day. Afterpay is still headquartered in Sydney, and Australian staff have been directly affected.

The same week, WiseTech Global announced 2,000 job cuts over two years — 29% of their workforce. CBA quietly cut 300 roles, mostly in technology. All three cited AI as the driver.

In this video, Dexter Cousins breaks down what actually happened and gives you three practical steps to take today if you've been affected or think you might be next.

Chapters

• 00:00 Navigating Job Loss in FinTech
• 01:39 How Your Experience Is In Greater Demand Than Ever
• 03:02 Avoid Three BIG Mistakes
• 03:49 Career Balance Sheet
• 05:03 Identifying Opportunities
• 05:45 GTM Strategy — Quick Wins
• 07:09 Building Momentum and Networking

Career Balance Sheet - https://drive.google.com/file/d/1hLJJQl2B_h1u00G46sNxlhGNRXXZlCv6/view

Part 1 - https://tieronepeople.com/2025/11/14/find-fintech-jobs/

Part 2 -https://tieronepeople.com/2026/01/12/professional-networks-job-hunting/

Part 3 - https://tieronepeople.com/2026/02/16/professional-brand-first-principles/

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🔥 We find the 1% who redefine what's possible - Executive search for fintech → https://tieronepeople.com

Checkbox AI just raised $23M at $100M valuation serving enterprise customers SAP, PepsiCo, Telstra, and Woolworths. CEO Evan Wong shares the 9-year journey from bootstrapped startup to enterprise legal AI platform, competing against $5B+ valuation businesses like Harvey.

📊 KEY METRICS:

• US$23M Series A at $100M valuation (total of US$29m raised)

• 100+ enterprise customers including Fortune 500

• Capital Raise will be used to expand into the US market

• Named in Gartner's 2025 Hype Cycle for Legal Tech

• 9-year journey from founding to Series A

⏱️ CHAPTERS:

00:00 Introduction to Checkbox AI and Its Journey

02:26 Understanding Checkbox AI's Role in Legal Tech

06:27 The Evolution of No-Code and AI in Legal Solutions

10:50 Navigating the Competitive Landscape of Legal AI

12:58 The Importance of Customer-Centric Product Development

18:49 Building for Enterprise: Lessons Learned

25:58 Scaling Efficiently in the Age of AI

28:38 Embracing an AI-First Mindset

31:19 Navigating Fear and Shame in Entrepreneurship

35:09 Advice for Young Entrepreneurs

39:51 Finding Energy and Passion in Work

40:52 Building a Resilient Organization

44:23 Future Plans and Growth Strategies

🔗 EVAN WONG:

LinkedIn: https://www.linkedin.com/in/theevanwong

Checkbox AI: https://www.checkbox.ai

📰 EPISODE SOURCES:

Checkbox Series A Announcement: https://www.checkbox.ai/news/checkbox-raises-23-million-series-a-to-become-the-front-door-for-in-house-legal-teams

📺 ABOUT FINTECH CHATTER:

Australia's leading fintech podcast with 350+ episodes reaching 30,000+ fintech professionals in 40 countries monthly.

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Tier One People placed Matt Baxby as Revolut Australia's founding CEO. Six years later: 1M customers, profitable. The right leader changes everything. Looking for your next hire? Contact Dexter Cousins for a confidential discussion.

Welcome back to Fintech Chatter Podcast - In our first episode of 2026 Matt Baxby reveals how Revolut reached 1M customers and saved Australians $250M in FX fees while achieving profitability. Discover the hiring secrets, growth strategy, and vision to become Australia's #1 finance app.

Chapters
00:00 Introduction and Milestone Achievements
06:45 New Products
12:08 Banking License Update
14:06 Why Revolut has outlasted other Neobanks
16:37 6 Years at Revolut, One Million Customers.
20:09 What makes someone successful at Revolut?
24:46 Why Revolut's "work from anywhere" policy works.
28:04 What's next for Revolut?
31:33 Careers at Revolut

Links
Revolut Careers: revolut.com/careers

Revolut Australia: revolut.com/en-AU

Discuss Hiring: tieronepeople.com/contact

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Most people treat networking like fitness - they lie on the sofa for three years, then panic when they're out of shape. In this episode, Dexter Cousins breaks down the 95-5 principle: 95% of your job hunting success comes from 5% of your network. Learn how to identify the critical 5% of your network, activate them strategically, and turn two-minute conversations into warm introductions. This is networking done right.

KEY TAKEAWAYS

• The 95-5 Principle: Focus on your critical 5%, not broadcasting to thousands
• T1/T2/T3 Framework: How to filter your network strategically
• The Two-Minute Ask: Why small requests get bigger results
• Compounding: How one conversation generates 1-2 warm introductions
• The Trust Shortcut: Borrow credibility through warm introductions

FREE DOWNLOAD

Network Activation Worksheet - Get your T1/T2/T3 filter template, email scripts, and conversation guide. https://tieronepeople.com/wp-content/uploads/2026/01/Network_Activation_Worksheet-1.pdf

ABOUT THE HOST

Dexter Cousins is Managing Director of Tier One People, the executive search firm for Fintech. With 25+ years in recruitment, Dexter has an unmatched record helping fintech companies build exceptional leadership teams.

NEXT EPISODE

Episode 4: The Interview - How to interview like you're diagnosing their business, not begging for a job.

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🚀 Hire outstanding Fintech talent - https://tieronepeople.com
✅ Follow Dexter on Linkedin - https://www.linkedin.com/in/dextercousins/
⬇️ Download the worksheet - https://drive.google.com/file/d/1rkcgAsabfYtPrZw1owzg1BpsnUxvLCDR/view?usp=sharing

In this episode of FinTech Chatter, Dexter Cousins shares insights on how to find your next role in the fintech industry using the Lean Startup methodology. He emphasizes the importance of creating a career balance sheet, identifying problem customers, and positioning oneself as an expert before applying for jobs. Dexter provides practical steps to research and validate hypotheses about companies' needs, turning job hunting into a targeted and strategic process.

00:00 Creating Your Professional Brand
06:24 Leveraging Top Brands
07:42 Finding Target Companies
08:31 Organizing Your Research
10:42 Iterating Your Approach
12:02 The Importance of Precision in Job Applications

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Thinking about your next career move in 2026? Maybe you're actively hunting for your next role in Fintech?

This is Episode 1 of a 5-part series that completely flips the script on job hunting in fintech. Whether you're looking for a permanent role or exploring fractional opportunities, this approach will transform your entire career conversation.

Most job seekers approach their career transition completely backwards. They ask the wrong questions, compete on the wrong battlefield, and leave millions in untapped value on the table. This episode introduces the framework that transforms you from "Please hire me" to "Here's the problem I solve. Here's why you'd be crazy not to talk to me."

We break down:
- Why conventional job hunting is fundamentally broken
- The questions you should be asking instead
- How to identify the concrete problems you solve
- The Career Balance Sheet framework
- Real-world examples of value creation ($1.5M, $20M+, +40% revenue growth)
- Why this framework makes you remarkably hireable

Send us Fan Mail

Contact: info@tieronepeople.com

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