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Join Cheryl and Maxine on an insightful journey into early-stage investing in this episode of First Cheque. The discussion covers the transition from basic checklists to more sophisticated decision diaries, emphasizing structured evaluation and the importance of capturing and analysing decision-making processes over time. Key topics include understanding founder commitment, market size evaluation, and the balance between intuition and quantitative analysis. The episode offers practical advice on refining investment strategies through critical thinking, timely decision-making, and mitigating biases. Additionally, it explores the qualitative nature of early-stage investments and the value of leveraging instincts effectively. Tune in to transform your investment decisions with proven frameworks and mental models.

00:00 Welcome to First Cheque: Your Guide to Early-Stage Investing

00:22 Diving into Decision-Making and Mental Models

02:05 From Checklists to Decision Diaries

07:20 Evaluating Founders and Market Size

16:28 The Importance of Timing in Investment Decisions

20:13 Understanding Mid to Late-Stage Investing

20:56 The Role of Intuition and Quantitative Measures

22:38 Challenges of Data-Driven Investment Matching

23:17 Personal Experience with Investment Matching

25:49 The Potential and Limitations of AI in Investing

28:35 Decision Diaries: A Tool for Better Investment Choices

35:03 Key Questions for Investment Decisions

37:14 Reflections on Decision-Making and Instincts

37:38 Conclusion and Call for Feedback

Maxine's Decision Diary Template

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Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman.

As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs.

The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business.

As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/peartree

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Mentioned in this episode:

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In this engaging episode of Fintech Fun, host Chris Titley sits down with Andrew Butt, co-founder and CEO of Enable, a leading B2B SaaS platform in the supply chain sector. Andrew shares his journey from the initial conceptualisation of Enable to becoming a globally recognised software solution, highlighting the company's unique approach to managing incentive agreements and rebates for retailers, distributors, and manufacturers. As Enable continues to expand its footprint in the Australian market, this episode delves into the company's history, growth, and future plans.

Enable has created a new software category through innovative rebate management solutions, capturing significant global market share. Andrew discusses how the company bootstrapped its way to securing initial clients and subsequently raised series A through D funding from prestigious venture capital firms like Menlo Ventures, Norwest Venture Partners, and Lightspeed. He explains the role of rebates in driving revenue and margin improvement within supply chains, emphasising the vast potential and ROI Enable provides to its clients. Andrew also touches on developing AI features to enhance the platform, ensuring Enable maintains its cutting-edge position in the industry.

• Emergence of Rebate Management as a Software Category: Enable is pioneering a relatively new software category focused on managing incentives and rebates within supply chains, demonstrating a significant global demand.

• Significant ROI for Clients: Enable’s platform offers substantial ROI for businesses by optimizing rebate agreements and uncovering previously untracked revenue.

• Global Expansion and Funding: Enable has successfully expanded internationally, supported by significant investment rounds from top-tier venture capital firms.

• AI Integration Plans: AI is a key focus for Enable, with plans to integrate it further into their platform to provide more substantial insights and optimization capabilities.

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Mark Frein, COO of Oyster HR, shares his insights on building transparent, fair, and scalable compensation frameworks for startups, emphasising the importance of clear communication and alignment with company values.

Ilkka Turunen is the CTO at Sonatype, a company that helps millions of software developers use open-source software while minimising security risk. In this conversation, Ilkka chats with Cole Cornford about the benefits and risk of using open-source software, how Maven helped standardise software development processes, the different approaches to AppSec regulation in Australia and Europe, and plenty more.

1:33 - Ilkka's career background

4:00 - Varying quality of open-source software

6:10 - How Maven helped standardise software development processes

13:00 - The balance between speed of delivery & quality

17:00 - Importance of environment parity in software dev

21:40 - Risk of using 3rd party code in software

25:10 - Regulation of AppSec in Australia vs Europe

32:10 - How new European software security regulations will be enforced

35:00 - Recommendations for compliance with European regulations

39:00 - Rapid fire questions

Mentioned in this episode:

Call for Feedback

Join Cheryl Mack and Maxine Minter for an engaging session as they delve into the world of early-stage investing with Matthew Browne from Black Nova Venture Capital. This episode offers an intimate look into Browne's journey from a founder's seat to a leading venture capitalist's role, with a focus on thematic investing in what he calls "boring B2B SaaS." Browne unravels the nuances of mission-critical software that businesses cannot operate without, discussing why such investment strategies are both conservative and highly lucrative.

The episode highlights Browne's investment philosophy—characterized by rigorous thematic focus, underscoring software's unturnoffable nature in various enterprise settings. He shares insights from his venture fund experiences, discussing the competitive dynamics of boring businesses and the journey of transitioning from an entrepreneur to a fund manager. Throughout the conversation, Browne also provides valuable advice to those considering venturing into fund management, emphasizing the importance of sticking to areas of known expertise and understanding the role's demands.

• Thematic Investment Strategy: Matthew Browne emphasizes investing in enterprise SaaS that is mission-critical to operations, underscoring the intrinsic value and longevity of such investments.
• Importance of Execution: His first investment’s failure taught the importance of knowing how to effectively acquire customers and sticking to one's domain expertise.
• Transition from Entrepreneur to Investor: Browne shares his journey into VC, stating the unique challenges of fund management compared to traditional business operations.
• B2B SaaS Success Factors: Long-lived customer relationships and LTV are key, with an enterprise focus often yielding higher customer loyalty and lower competitive pressures.

Deel: Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.

Ready to expand your business?

Build your global team with Deel at deel.com/dayone.

___

Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman.

As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs.

The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business.

As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/peartree

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Mentioned in this episode:

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Summary

Daisy Wong is the Head of Security Awareness at Medibank, as well as a disability advocate. Originally from a marketing background, Daisy gained experience in the cybersecurity industry working as part of penetration teams, before making her way into the security culture and awareness space. 

In her conversation with Cole Cornford, Daisy discusses using the tools of marketing to educate people on cybersecurity, what are the hallmarks of a good security culture and awareness program, and the importance of diversity in cybersecurity.

Timestamps

4:00 - Daisy's transition from marketing to cybersecurity

8:10 - The importance of security culture and awareness

11:00 - Building effective security awareness programs

14:15 - The role of diversity in cybersecurity

17:00 - Strategies for inclusive hiring practices

19:40 - The power of communication in security awareness

23:20 - Creative approaches to security awareness campaigns

31:45 - Daisy's personal perspective on the importance of diversity

43:40 - Rapid fire questions

Mentioned in this episode:

Call for Feedback

Listen/subscribe on 

* Apple podcasts

* Spotify 

He’s been Murray Hewitt, Psycho Sam, Norman from Yes Man, Guy Mann, Hypno-Potamus, a stand-up comedian, a sit-down band manager, a children’s book author, a soldier… and now Binkle-bonk the Tree Goblin in upcoming “Badjelly the Witch” 🤩

In this week’s Diaspora pod, legendary Kiwi comedian Rhys Darby joins us - live from L.A - to talk through his rise from Canterbury to Edinburgh to Hollywood in a career that’s seen him star in multiple comedy specials, voice over countless animated shows and co-star with everyone from Jim Carrey to Dwayne ‘The Rock’ Johnson. 

Rhys hasn’t made the journey alone: also joining us is his incredible wife & long-time manager, Rosie Carnahan Darby, who talks about her career in entertainment management, production, writing comedy, how comedians can get ahead, how entertainers can be devastated by changes in AI and tech… and shares the creative projects of their two sons in this very funny family. 

In today’s episode, we discuss

* Rosie and Rhys’s entwined journeys over 25 years in the global comedy industry, dating back to Rhys's "Dad's Army"-inspired entry into the NZ Army, and Rosie's rise as one of the most sought after comedy club managers in NZ.

* The business of comedy: how they think about new opportunities, structure and finance their ventures... and what the future holds.

* Tall poppy syndrome in NZ, and imposter syndrome in the U.S... how NZ's (over?) orientation towards equality and "fairness" actually holds back our highest achievers, and can drive them offshore.

* Raising a family in L.A. vs. NZ, finding balance and getting the best of both cultures.

* How some projects Rosie and Rhys write together don’t succeed, though the pair focus on creating future opportunities for other projects. 

* How Rhys found the next phase of his career after Flight of the Conchords finished.

* Why and how Rhys is now using Substack to build a direct connection with fans

* Advice on how to break out as a comedian and what managers like Rosie are looking for — comparing finding emerging creative talent with seeing talent in startups, from the POV of a talent manager/agent vs. venture capitalist.

* Whether AI might be able to help actors and voice actors, and whether AI is taking human jobs in a future in which screen entertainment might be created by robots

Make sure you head on over to Rhys’s substack and subscribe!

—

Also - quick shout-out from me: Blackbird’s Sunrise festival is coming up soon — November 26th in Wellington, NZ.

As we like to say, this is our love letter to startups and the people building them … a one-day festival that brings together ~500 tech founders, operators, policy people and ecosystem supporters to be inspired, challenged and entertained. 

Tickets are half gone and won’t be around for long… IF you’ve been looking for an excuse to get back to Wellington, this is it! Head over to thesunrise.live for more info + tickets!

Listen/Subscribe on:

* Apple Podcasts

* Spotify

Hint Health co-founder and CEO Zak Holdsworth retains a strong Kiwi accent - after all, he grew up on a farm near Gisborne. It was no ordinary farm, however, as Zak tells us.

Considering his mother was a diplomat and his father an inventor and pioneer of pultrusion, Zak developed a taste for innovation in the wider world, and eventually headed off to Stanford Graduate School of Business to achieve his MBA. Zak worked briefly as a VC prior to joining the founding team ofWellnessFX in 2011, a California company which diagnosed health conditions through blood analysis.

He then went on to co-found Hint Health in 2014 – a platform which has raised $64 in investment and today handles over a billion dollars worth of payments per year.

Based in San Francisco, Hint is a vertical SaaS platform powering Direct Primary Care practitioners allowing them to to focus on patients in an industry which has until recently been far too dependent on the insurance system to cover patient costs and which - as Zak tells us - wastes more money annually than NASA’s 60-year budget. Disrupting the $4 trillion US healthcare industry is a topic also shared by our previous guest Dr Zachary Tan.

Zak joins us to share his ideas about finding and investing in disruptive startups, the future of cryptocurrency, and how New Zealand might be a great place to run the next Xero from.

In today's episode, we discuss:

* Hint Health’s mission to step away from insurance, give everyone a transparent rate of costs and connect patients with unlimited access to primary care, telemedicine, urgent care and other services - the way Zak remembers it when he was a child in NZ

* Getting into Stanford business school, realising which paths weren’t ideal, before taking on US healthtech with Hint Health

* How Zak’s passion for startups included forays into venture capitalism as well as patenting a phone charger

* The staggering percentage of each dollar Zak feels is wasted when handled through health insurance.

* Reasons for lack of change in US healthcare

* Becoming respected in the healthtech community with the Hint Summit annual conference

* Whether the startup community's expectations of how quickly a startup should triple or 100x its revenue are fair expectations or not.

* DeFi Summer, and lessons learned while investing in crypto currency

* Faith in Bitcoin

* Zak's balance between being plugged into Silicon Valley but having peace and tranquility to focus on his family.

* …and whether New Zealand’s tech startup ecosystem is ready to host another Xero.

Referenced:

* Hint Health

https://www.hint.com/

* Stanford Graduate School of Business

https://www.gsb.stanford.edu/

* The Hint Summit

https://summit.hint.com/

Where to find Zak Holdsworth:

* LinkedIn https://www.linkedin.com/in/zakholdsworth/

X/Twitter https://x.com/zakholdsworth?lang=en

In this engaging episode, the hosts Cheryl Mack and Maxine Minter are joined by Georgie Turner, a partner at Tidal, to delve into the nuances of early-stage investing, cross-border strategies, and the evolving landscape of venture capital. The episode opens with a lively introduction to Georgie's background and her journey from Bailador to founding Tidal, a fund focused on B2B SaaS and AI. The hosts discuss the challenges and rewards of building a fund, the intricacies of capital management, and the importance of alignment between founders and investors.

Throughout the conversation, the trio explores the differences between the Australian and US venture capital ecosystems, touching on themes such as market size, customer sophistication, and the importance of domain expertise in founding teams. Georgie also shares insights on navigating the AI revolution and its impact on the tech stack and business models. The episode concludes with a reflective discussion on bravery in the venture capital space, emphasizing the optimistic and sometimes illogical nature of the industry.

• Cross-Border Investment: Georgie Turner discusses the importance of having a cross-border investment strategy, particularly focusing on the differences between the Australian and US venture capital ecosystems.
• Capital Management: Insightful exploration into how proactive capital management and accurate valuation alignment can significantly impact the success of early-stage investments.
• AI Investment: Detailed discussion on how AI is transforming the tech landscape and what investors should look for in AI-driven companies.
• Scaling Challenges: The episode highlights the challenges of scaling companies in different markets and the importance of market timing, product quality, and operational expertise.
• Bravery in Venture Capital: Reflections on the inherent bravery required in the venture capital profession, given its optimistic and sometimes illogical nature.

Thanks to our sponsors for helping to make this episode of First Cheque possible.

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Mentioned in this episode:

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In this week's episode of The Startup Retro, host Will Richards and guest host Cheryl Mack from Aussie Angels and The First Cheque podcast break down the latest in Australia's startup and venture capital ecosystem. They cover Square Peg's ambitious new funds, the 2023 financial results of Linktree, and a groundbreaking partnership that will see hypersonic rocket launches from South Australian spaceports in 2025. The duo also discuss SafetyCulture's latest $75M raise, Algenie’s mission to replace plastics with algae, and interview Emma Grife from Startmate about their latest cohort. The episode wraps up with a useful resource for B2B startups navigating their sales funnels.

00:00 Introduction and Welcome

05:00 Square Peg’s New Funds

09:00 Linktree’s 2023 Financials

12:30 Hypersonic rocket launches in South Australia

15:00 SafetyCulture’s Latest Raise

18:30 Algenie’s plastic replacements using Algae

25:00 Interview with Emma Grife from Startmate

30:00 Knowledge as a Service (KaaS) Recommendations

To get all the links to the stories we mentioned in this episode, you can read this week’s https://newsletter.overnightsuccess.vc/p/aussie-startup-vc-summary-14th-september

• Square Peg’s New Funds
• Square Peg is raising $840M for its sixth fund, focusing on seed and Series A investments, with a minority stake strategy. They are also raising $210M for their Opportunities Fund 3, highlighting strong returns from Canva and challenges in recent vintages.
• Linktree’s 2023 Financials
• Linktree revealed a $61.6M loss for 2023, spending $2 for every $1 earned. Despite generating $42.8M in revenue, the startup cut its workforce by nearly half. The founders took $21M off the table in secondary sales.
• South Australian Hypersonic Rocket Launches
• Hypersonix Launch Systems will partner with Southern Launch to enable Mach 7 hypersonic rocket launches from South Australian spaceports by 2025, dependent on environmental assessments.

• SafetyCulture
• Raised $75M in fresh capital with an additional $90M in secondaries at a $2.5B valuation. SafetyCulture plans to enhance its workplace solutions with AI-powered tools and IoT functionalities.
• Algenie
• Secured $1.1M in pre-seed funding to scale algae production as a sustainable alternative to fossil fuels and plastics. Algenie’s innovative photobioreactor system can produce 100 tonnes of algae annually, offering a scalable solution for carbon sequestration and renewable materials.

• Emma Grife from Startmate

Will speaks with Emma Grife from Startmate, discussing the latest cohort and how the accelerator is helping early-stage startups in Australia.

• Will’s Pick 💁🏻‍♂️
• GTM Funnel Stages, Metrics, and Goals for B2B Startups by Unusual VC – A comprehensive guide on navigating B2B sales motions from awareness to close.

1. Gemma on LinkedIn
2. Will on LinkedIn

Thanks to our sponsors for helping to make this episode of The Startup Retro possible.

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