Day One®

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Summary

Anabel Lippincott Paksoy, partner at 43, discusses the importance of building communities and their role in early-stage investing.

She shares her experience creating the council, a female-first investing group, and emphasises the need for a deep understanding of founders and their motivations.

Anabel also highlights the value of professionalising angel investing and finding founders with a strong sense of purpose and followership.

She concludes by discussing her investment preferences, focusing on niche communities and founders with a deep understanding of unsexy problems.

About The Guest

Anabel Lippincott Paksoy is a partner at 43, a pre-seed fund based in the Bay Area. She is also a partner at The Council, a female-first investing group. Anabel has a background in people operations and has a passion for building communities and supporting early-stage founders.

Key Takeaways

• Building a community is about creating a space for like-minded individuals to connect and share deal flow.
• Investing in early-stage startups is a high-risk asset class and should not be undertaken unless one is aware of the risks and willing to lose the money.
• Angel investing can be treated as a learning budget, focusing on maximising learning and gaining experience rather than making immediate financial gains.
• When evaluating founders, looking for a deep, authentic “why” behind their venture and a strong sense of purpose is essential.
• The ability to pivot and adapt is crucial for founders, as it demonstrates a willingness to learn and iterate based on feedback and market conditions.
• Successful founders' ability to attract top talent and inspire followership is a crucial trait.

Quotes

• “I think the thing that I needed, and again, it’s interesting how trends have shifted, too. Even in 2018, five years ago, it was a little new for operators. These female operators were not already super independently wealthy, to think about deploying capital as independent investors into startups.” - Anabel Lippincott Paksoy.
• “I think the thing that I know that I look for in people is some kind of deep, deep, deep, deep why that they’re doing what they’re doing.” - Anabel Lippincott Paksoy.
• “I want to feel that conviction, and there’s no way to vet that. That’s where it gets super personal. I want to ask, could I fall in love with this founder, and I don’t mean romantically? I mean, would I go work for them?” - Anabel Lippincott Paksoy

Resources

• Anabel Lippincott Paksoy
• 43
• The Council
• The Assembly

Timestamps

0:00:00 - Introduction to the podcast and guest.

0:01:57 - Discussion about Anabel’s first investment.

0:05:04 - Conversation about nostalgia and fashion trends.

0:06:12 - Exploring the concept of building communities.

0:09:48 - Challenges and principles of community design.

0:10:30 - Constructing a community for sharing investment deals.

0:11:55 - Creating a learning platform through a consortium of investors.

0:13:14 - Frustration with lack of conversation about deals in the peer group.

0:15:15 - Directing new angel investors to be aware of high risk.

0:17:31 - Treating angel investing as a learning budget.

0:18:48 - Normalising lower entry prices for angel investing in Australia.

0:19:24 - Contributing to the founder’s

Mentioned in this episode:

Deel x PX_Script 1

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Summary

Cheryl Mack and Maxine Minter reflect on the year 2023 and discuss the challenges and trends in the startup ecosystem. They talk about the tough environment for founders and investors, with many companies struggling to raise funds and facing down rounds. However, they also highlight the resilience and determination of founders who were able to survive and even thrive in the face of adversity.

The hosts discuss the increase in funding for female founders, although there is still a long way to go in achieving gender parity in the industry. They also touch on the growth of climate tech and AI as key areas of investment, with these sectors propping up the funding ecosystem.

Cheryl and Maxine express cautious optimism for the year 2024, noting the need for continued creativity and resilience in the face of challenges. They also highlight the importance of addressing issues of behaviour and inclusivity in the startup ecosystem.

Key Takeaways

• Challenges in the Startup Ecosystem (2023): The year was marked by difficulties for many companies in raising funds, with instances of down rounds reflecting a challenging environment for the startup ecosystem.
• Resilience of Founders: Success in these tough times was often attributed to the resilience and determination of founders, who demonstrated the ability to navigate through the demanding market conditions effectively.
• Funding for Female Founders: While there was a notable increase in funding for female founders, reaching a historical high, the conversation acknowledges that more efforts are necessary to achieve gender parity in funding.
• Growth of Climate Tech and AI: Both climate tech and AI emerged as standout sectors, drawing significant investments and spearheading innovation despite the broader economic challenges.
• Outlook for 2024: The year ahead is approached with cautious optimism. The emphasis is on the necessity for ongoing creativity and resilience to address and overcome upcoming challenges.

Quotes

- "I think ingenuity was a real theme. I'm excited to dive in today, obviously. Tis the season to be reflecting." - Cheryl Mack

- "The founders that survive this are the ones that we are so excited to back as investors." - Maxine Minter

- "I think optimism and holding on to a sense of optimism won this year. Pairing it with creativity, also really effective." - Maxine Minter

- "I think 2024 is looking cautiously optimistic. Cautiously optimistic." - Maxine Minter

Chapters

00:05 - Introduction to the podcast

00:25 - Reflecting on the year and the challenges faced

02:02 - Difficulty of raising funds and the resilience of founders

04:32 - Founders' determination to survive and adapt

05:08 - Employment Hero becoming a unicorn

06:31 - Tentative re-entry of international investors into the Australian ecosystem

07:38 - Gap between top founders and average deals narrowing

08:49 - Overpaying in the early stages of funding

09:05 - Australian tech facing criticism from the media

10:46 - Turning point in sentiment with SVB collapse and Milk Run

11:18 - Discussion about the impact of FTX and Sam Bankman-Fried's sentencing

12:13 - AI and climate tech propping up the funding industry in 2023

13:56 - AI adoption curve and its impact on the legal tech industry

15:01 - Tight capital environment in Q1 and Q2 of 2023

15:32 - Increase in interest and funding for climate tech

17:10 - Rise of climate tech-focused funds in Australia

18:19 - Lack of AI-focused funds in Australia

20:06 - Creativity in funding and rise of professionalized fund management

21:30 - Optimism about more fund raising in 2024

21:52 - Increase in funding for female founders, but still low overall

22:33 - Matching population demographics

22:48 - Lack of data on women-led...

Mentioned in this episode:

Deel x PX_Script 1

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The cybersecurity industry is made up of people from all sorts of different backgrounds, and Michael Collins is a perfect example. After spending 8 years in the Australian navy, Michael moved to Cairns and became a diving instructor. After 5 years, Michael decided it was time for a career change and enrolled in a course to become a Microsoft certified systems engineer.

Today, he’s Chief Information Security Officer at Judo Bank. In this episode we chat about how Michael has managed major transitions in his career, the importance of aligning cybersecurity strategies with business goals, systems thinking as a framework for approaching cybersecurity, and plenty more.

Systems Thinking Made Simple - by Derek Cabrera:

https://www.amazon.com.au/Systems-Thinking-Made-Simple-Problems/dp/1520740492

Secured by Galah Cyber with Cole Cornford website

2:20 - A good summary of Judo Bank

7:10 - How Michael became a CISO

9:00 - How Michael almost bailed on his cybersecurity training after day one

12:00 - The joys of scuba diving

14:30 - Advantages of systems thinking

16:30 - How someone can get started with systems thinking

17:40 - DSRP thinking (Distinctions, Systems, Relationships and Perspectives)

24:20 - Delivering AppSec by meeting the business where it is, not being idealistic

25:20 - “It’s not all about downsides”, businesses succeed by taking risks

27:10 - How we can promote more business-mindedness in cyber

32:50 - Michael’s transition from techie role to CISO

39:50 - Cole: “Leadership is a funny thing”

43:30 - Rapid fire questions

Mentioned in this episode:

Call for Feedback

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Summary:

Elaine Stead joins the podcast to discuss bravery and courage in the investing world, particularly as a woman in the Australian ecosystem. She shares her journey as an investor and highlights the importance of investing in education and building networks.

Elaine also challenges the notion of being a contrarian investor and emphasizes the need for a high tolerance for risk. She discusses portfolio construction and the importance of managing risk and diversification.

The conversation also touches on the challenges faced by women in the industry and the need for change in the ecosystem.

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About The Guest:

Elaine Stead is a General Partner at M8 Ventures and an experienced investor in the Australian ecosystem. With nearly 100 investments under her belt, she is known for her bravery and courage in making investment decisions. She has a background in science and innovation and has built a strong network in the industry.

Key Takeaways:

• Investing in education is a crucial investment that can change the trajectory of one's life.
• Building networks is essential for success in the investing world, particularly for women.
• Being a contrarian investor is about having a higher tolerance for risk and being able to see opportunities early.
• The Australian ecosystem needs more diversity in capital allocation and investment decisions.
• Wealth creation and equity allocation should be more inclusive to drive change in the industry.

Quotes:

• "Being brave is about being fearful of something, but doing it anyway." - Elaine Stead
• "Diversity in teams signals the ability to manage conflict and work with people who think differently." - Elaine Stead
• "Making room for others is a show of strength and confidence." - Elaine Stead

Resources:

• M8 Ventures: Elaine Stead, the guest on the podcast, is the General Partner at M8 Ventures, a venture capital firm. (Timestamp: [00:00:49])
• Day One Network: The podcast is part of the Day One network, dedicated to founders, operators, and investors. (Timestamp: [00:00:08])
• Elaine Stead: A prominent figure in the Australian investing ecosystem, recognized for her experience and insights into investing. (Various Timestamps)
• Alex Rampell: Mentioned by Maxine Minter in the context of investing perspectives. (Timestamp: [00:10:15])
• South by Southwest Sydney: Elaine Stead mentions she will be on a panel at this event. (Timestamp: [00:25:20])
• Aussie Angels: Discussed in the context of making investment...

Mentioned in this episode:

Deel x PX_Script 1

This podcast uses the following third-party services for analysis:

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Join us as we speak with Josh Weeks, founder and Director of Alpha Echo, an Australian cybersecurity company. Josh shares his journey from wanting to be a teacher to becoming an aerospace engineer for the Australian Defence Force.

After leaving the ADF, Josh struggled to find work but eventually launched his own contracting company in Canberra. He later moved his family back to Newcastle and slowly grew his business by expanding into new government contracts. Today Alpha Echo has 35 employees across cybersecurity, training, and classified facilities management. Josh discusses the challenges of starting a company and his focus on hiring good people and giving back to the Newcastle region. He explains how Alpha Echo aims to improve Australia's cybersecurity posture through education and leading by example. Tune in to hear more about the origins and growth of this homegrown cybersecurity firm.

Seth Law is Founder and Principal Consultant of Redpoint Security, an AppSec consulting firm that focuses on code security, as well as co-host of the fantastic Absolute AppSec podcast. Seth has plenty of experience with the nitty gritty details of software development, and Cole Cornford had a great time nerding out with him about static analysis tools and code reviews.

They chat about the potential for AI to improve AppSec, the unhelpful tendency to idolise big tech companies, the importance of good communication between developers and AppSec, and plenty more.

Secured by Galah Cyber with Cole Cornford website

Mentioned in this episode:

Call for Feedback

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Rayn Ong is the angel investor a startling number of Australian founders trace a key introduction back to — Cheryl Mack and Maxine Minter call him the "all-seeing eye" who somehow sees every deal in the ecosystem. On this First Cheque he breaks down how he actually built that, and how he backs the breakouts.

It starts at ground zero. Rayn's first money out of the trust account was Blackbird Fund 1, in 2014 — he was one of the last five in before the final close, and paid three capital calls in one go. The same year he backed Instaclustr (later acquired for US$500M). Eight investments in his first year.

The network edge wasn't luck. In 2014 the ecosystem was barren, so he simply met everyone — Sydney Angels taught him to run deals and syndicates, and he'd reach out to co-investors on every term sheet. His real entry ticket: as a nine-year software engineer he did the technical due diligence the finance-and-legal crowd couldn't — interviewing CTOs, mapping competitors — so they looped him into the best deals. Do that useful thing in one niche, repeatedly, and the network compounds and sources deals for you.

That's also how he invests across wildly different industries — microchip maker Morse Micro, alternative protein, even literal ginger — by trusting domain experts and asking "what if this works?" rather than "what if I lose?" The common thread, in his words, is anything that grows.

The real money is in the breakouts. Rayn writes small first cheques to learn, then goes heavy on the one obvious winner per cohort — Eucalyptus hit US$100M revenue in four years; the crypto game Stepn made US$20M profit in a single quarter. His 25k becomes 250k. Counterintuitive to public-market investors: he buys more when the price has tripled, because the context has changed.

He's also built a "plug and play" proposition for founders. They raise once a year; he raises every month and knows the active angels and funds for each round — so he offers a low-friction path to the next raise, doing 10–40 reps a year. And he de-risks new bets with the portfolio he already has: a company whose customers or investors are his other companies. Evaluate the system, not the deal.

Inside the Archangel Fund, his gut-feel, zero-to-one "YOLO" allocation became the thing LPs (Maxine among them) most wanted in. He's the early-stage instinct guy; partner Ben Armstrong runs the later-stage follow-ons. The cojones moment: personally bridging a whole round when almost nobody believed it would work — and the LPs who passed on his 2018 fund coming back for the 2022 one, one of them screenshotting his old pitch deck to mark every "I told you so."

**Rayn Ong** is an angel investor and connector across the Australian startup ecosystem, investing through Archangel.

**Links**

- Rayn Ong on LinkedIn: https://www.linkedin.com/in/raynong

- Archangel Ventures: https://www.archangel.vc

- First Cheque: https://dayone.fm/first-cheque

- Cheryl Mack on LinkedIn: https://www.linkedin.com/in/cherylmack

- Maxine Minter on LinkedIn: https://www.linkedin.com/in/maxineminter

Thanks for listening to First Cheque.

First Cheque is brought to you by the Day One Network. (Sponsor read — confirm the current sponsor copy from the most recent episode before publishing.)

Episode Summary

Angel investor Rayn Ong joins Cheryl Mack and Maxine Minter for a masterclass in early-stage investing — how he built a network that filters the best deals, why he backs "anything that grows," how he goes heavy on the one breakout per cohort, the "plug and play" model he offers founders, and how he de-risks new bets with the portfolio he already has.

Time Stamps

00:00 - Cold open
02:04 - Why Rayn was Maxine's first call when she started angel investing
04:30 - His first cheque: Blackbird Fund 1, 2014
06:55 - Building a network that filters the best deals
10:04 - Compounding for early-stage investors
11:54 - Investing across every industry — and "anything that grows"
20:05 - Long on ginger: a 29% yield
24:35 - Backing the one breakout per cohort
27:14 - The "plug and play" fundraiser model
34:01 - Portfolio synergy: de-risking with your own companies
39:29 - The YOLO portfolio and the 2018 fund he couldn't raise

About the host

First Cheque is hosted by Cheryl Mack and Maxine Minter — two angel investors talking to the people building and backing Australia's startup ecosystem.

About Day One Network

Day One is a podcast network for founders, operators and investors. Find more shows at https://dayone.fm.

This podcast uses the following third-party services for analysis:

Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
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Summary

Rayn Ong, an angel investor and founder of Archangel, shares his insights on early-stage investing in this episode of First Cheque. Rayn discusses his first investment in Blackbird Fund One and how he built his network in the Australian startup ecosystem.

He emphasises the importance of compounding value in both networks and investments. Rayn also talks about his investment strategy, including his focus on breakout companies and his approach to evaluating opportunities.

He shares his thoughts on portfolio synergy and competition within his portfolio. Overall, Rayn's entrepreneurial approach to investing has led to his success in the industry.

About The Guest(s)

Rayn has been an active angel investor since 2014. He has invested in the early rounds of Instaclustr, Propeller Aero, HappyCo, Morse Micro, Carbar, Eucalyptus, Vow Food and StepN which are all valued at over $100 million now.

Rayn is a partner at Archangel Ventures, an angel fund that backs founders at the earliest stage possible. Rayn made his debut on the AFR Young Rich List in 2022 as an angel investor.

Key Takeaways

• Cultivating a strong network and building relationships is crucial for sourcing high-quality deals in the startup ecosystem.
• Specialising in a certain vertical or industry can provide a competitive advantage in evaluating startups and making informed investment decisions.
• The ability to identify breakout companies and double down on successful investments is key to achieving high returns in early-stage investing.
• Investing in companies that have synergy with existing portfolio companies can help derisk investments and create value for the entire portfolio.
• Setting clear expectations with founders and providing guidance throughout the investment journey can lead to successful outcomes and future funding rounds.

Quotes

• "We want to align for a good founder experience. We disclose upfront if we have exposure to potential competitors and encourage sharing to benefit the entire ecosystem." - Rayn Ong
• "We minimise risk by starting with small checks and gathering information over time before making larger investments." - Rayn Ong
• "The ability to compound value in networks is as valuable for early-stage investors as it is for the assets we invest in." - Rayn Ong

First Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

Learn more by joining Day One's newsletter. We create content to help founders. https://dayone.fm

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Mentioned in this episode:

Deel x PX_Script 1

This podcast uses the following third-party services for analysis:

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In this episode, Carolyn Breeze shares her career journey through the world of tech and payments. Starting at eBay, she gained experience at large Silicon Valley companies before becoming Country Manager for Braintree in Australia. Her passion for payments grew as she helped expand GoCardless's services down under. After a stint as Chief Commercial Officer at Zepto, Carolyn took on the CEO role at Scalare Partners - an early stage investment firm with a unique model. 

Carolyn outlines how Scalare differs from traditional VC firms by taking an active role in helping their 26 portfolio companies. She also provides advice on taking on new challenges to expand skills, even if you feel underqualified. The conversation covers the sacrifices of being a startup founder, the importance of founder self-care and salaries, and why founders deserve the opportunity to benefit financially from secondary sales. Carolyn reflects on her learnings so far and the value of ongoing education and resources. Tune in for an insightful chat about thriving in tech, the payments space, and the world of startups and investing.

Jeanette Gill is Principal Customer Success Manager at Secure Code Warrior. Jeanette comes from a non-technical background, having worked in the aviation industry for over a decade. When she made the leap into AppSec, it was her communication skills and focus on providing a great experience for customers which proved invaluable.

Jeanette chats with Cole Cornford about some common misconceptions about AppSec, the sometimes uneasy relationship between developers and AppSec, the potential for AI to change our industry, and plenty more.

Secured by Galah Cyber with Cole Cornford website

7:30 - Jeanette’s career background in aviation

10:40 - Working for airline “best years of my life”

13:10 - Giving up career to move to Australia

15:20 - Jeanette’s current role at Secure Code Warrior

16:40 - Developers being wary of appsec

20:40 - Cole: I don’t think education issue, but incentive issue

24:00 - Using AI to improve appsec

24:40 - What is Secure Code Warrior

28:00 - What do teams struggle with in terms of Appsec?

36:00 - Management leading by example

38:40 - Often, devs don’t want to hear from appsec team

43:00 - How did Jeanette get involved with appsec after moving to Aus

46:50 - Value of webinars, podcasts, and people sharing knowledge online

47:30 - Developers, programmers or engineers, what’s the correct term?

51:50 - The importance of titles and job descriptions

52:30 - Rapid fire questions

59:30 - Jeanette: hug your appsec team

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