Fintech Chatter: Conversations with Fintech CEOs and Founders

If you're scaling your fintech leadership team, start at tieronepeople.com
Chris Brycki founded Stockspot in 2013 with no income, no office and no VC, and built it into Australia's largest automated investment service with $1.5 billion under management. In this episode, Chris and Dexter discuss what it actually takes to build an enduring fintech in Australia: staying lean, rejecting growth-at-all-costs capital, and never losing sight of the customer.

About Chris Brycki
Chris Brycki is the founder and CEO of Stockspot, Australia's first and largest automated investment service. He left a career on the institutional side of finance in 2013 to build a lower-cost, evidence-based alternative to traditional financial advice, and has since made money for 99.3% of clients who have invested with Stockspot for at least a year.

What We Discuss
How Chris validated Stockspot's concept with friends before writing a single line of code
Why he walked away from institutional finance to start a business with no income
The Fat Cat Funds Report: how naming and shaming underperforming super funds drove real industry change
Why paid marketing fails when you're competing against CBA's use-it-or-lose-it budget
How Stockspot has made money for 99.3% of clients invested for at least a year
Why Chris rejected VC and how that decision shaped everything that followed
The discipline required to avoid meme stock temptation during the 2021 trading frenzy
What nearly $500 million in client profits means in terms of real lives changed
Why the next generation of fintech will be built with smaller teams and less capital raised
Chapters
00:00 Introduction and Background of StockSpot
05:14 The Journey of Entrepreneurship
12:16 Growth Strategies and Media Influence
16:19 Regulatory Challenges in FinTech
20:03 Staying True to Core Values
25:57 The Future of FinTech and AI
30:11 The Evolution of Founders and Startups
35:07 Impact of FinTech on Society
39:10 Maintaining Innovation and Customer Focus

Links and resources
Chris Brycki on LinkedIn: https://www.linkedin.com/in/brycki/
Stockspot: stockspot.com.au
Fat Cat Funds Report: https://www.stockspot.com.au/fatcat/
Fintech Chatter: fintechchatter.com
Tier One People: https://tieronepeople.com/

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

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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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Contact: [email protected]
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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

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