Avsnitt
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Side Stage Ventures and Dealroom have just released the 2026 edition of their landmark report on Australian venture. Grab your copy of the Australia Venture & Startup Report 2026 here: https://www.sidestage.vc/outliers-report-2026
Australia has created more unicorns per dollar of VC invested than anywhere else in the world — and Ben Grabiner has the data to prove it. In this replay, Cheryl and Maxine sit down with the Side Stage Ventures co-founder to unpack why the ecosystem punches so far above its weight, and why the next decade could belong to Aussie tech.
Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.
It's why more than 40,000 fast-growing companies trust Deel to move fast.
Visit https://www.deel.com/dayone
Episode Summary
Ben Grabiner is the co-founder and General Partner of Side Stage Ventures and the author of a landmark report, produced with Dealroom and AWS, on Australia's venture ecosystem. Cheryl and Maxine sit down with Ben to unpack the data behind Australia's rise as one of the most efficient and exciting venture ecosystems in the world.
They dig into why Australia produces more unicorns per dollar of VC invested than anywhere on earth, how the country quietly matches Israel and India on decacorn creation, and why roughly 40% of local seed capital now comes from overseas, a sign global funds see the opportunity more clearly than we do. Ben explains why capital constraints have bred a culture of doing more with less, why fewer than 30 Australian seed funds made more than five investments last year, and what has to change to close the early-stage funding gap.
You'll also hear why the next wave of second- and third-time founders could be the ecosystem's secret weapon, what global LPs still need to understand about Australian venture, and Ben's own Big Cojones moment: throwing it all in mid-COVID to move from London to Australia.
Time Stamps
00:00 - Cold open: more unicorns per dollar than anywhere
00:52 - Intro
04:48 - Ben's first investment: 250 pounds in Tottenham Hotspur
07:01 - The headline stat and what drives Australia's capital efficiency
09:24 - Why constraints breed efficiency, and why it's good for VCs
12:31 - Decacorn creation: Australia on par with Israel and India
14:35 - 40% of seed capital comes from overseas
16:24 - What needs to happen to close the capital gap
20:41 - Can startups scale globally from Australia?
26:14 - What global LPs need to understand about Australian venture
28:28 - The rise of second- and third-time founders
30:37 - Why pre-seed funds and angel investors matter more than ever
34:41 - Ben's Big Cojones moment: moving to Australia mid-COVID
Resources
Ben Grabiner on LinkedIn - https://www.linkedin.com/in/bengrabiner/
Side Stage Ventures - https://www.sidestage.vc/
Australia Venture & Startup Report 2026 - https://www.sidestage.vc/outliers-report-2026
Aussie Angels - https://www.aussieangels.com/
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Episode Summary
Alex Feldman is the founder of Tiger and Bear, an M&A advisory focused on tech and services businesses. Before that, he was Chief Strategy Officer and General Counsel at Amaysim, where he ran three acquisitions simultaneously during full lockdown in 2020 and 2021 to build a dominant player that was ultimately sold.
In this episode, Cheryl and Maxine unpack how to buy and sell businesses when the world is doing crazy stuff around you. Alex breaks down why today's volatility isn't actually that different from the GFC or COVID, why timing is the single most important variable in any deal, and what the SaaSpocalypse means for tech companies thinking about selling when their natural buyers are struggling.
You'll also hear why more than half of Tiger and Bear's recent deals involved European and Asian capital rather than American, why profitable venture-backed businesses are suddenly more attractive to strategics, and what happens when the IPO market disappears as an exit path. For founders who can't raise their next round, he offers blunt advice: never waste a crisis, cut costs to buy yourself runway, and remember that raising and selling are the same activity, you're just selling different amounts of shares.
Alex closes with his Big Cojones moment: putting every spare $500 into the stock market during the GFC with no idea where the bottom was, buying Macquarie Bank shares at $30 and riding them back up.
Time Stamps00:00 - Intro
02:25 – Alex's first investment: going all in on the BHP Rio Tinto merger that never happened
06:19 – How to do M&A in volatile markets and why this cycle isn't that different
11:50 – Timing for buyers vs sellers: why uncertainty kills deals, not direction
13:08 – The SaaSpocalypse: what happens when your natural buyer is struggling
18:10 – Why European and Asian capital is replacing American buyers in Australia
21:08 – What M&A looks like in the Australian tech ecosystem right now
24:01 – When is a company big enough to buy and too small to be acquired
28:30 – Mergers of equals: why similar-sized companies come together in downturns
38:39 – How to become a disciplined buyer: capital, internal muscle, and integration
43:08 – Why the hardest part of any deal is admitting the other side does it better
47:54 – What to do when you can't raise: never waste a crisis
55:01 – Big Cojones moment: investing every spare dollar during the GFC
Sponsors:First Cheque is supported by our wonderful sponsors:
Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.
It’s why more than 40,000 fast-growing companies trust Deel to move fast.
Visit https://www.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
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
Deel x PX_Script 2
Pear Tree
If you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost.Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business.As a Day One listener, 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.
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Saknas det avsnitt?
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Episode Summary
Alexey Mitko is a partner at Co-Ventures, the architect behind Eucalyptus' ESOP plan, and widely known in the Australian ecosystem as "ESOP Guy." He was around employee number twenty at Canva and one of the early employees at Koala, giving him a front-row seat to three of Australia's biggest consumer tech outcomes.
In this episode, Cheryl and Maxine unpack how Alexey designed the ESOP plan that led to roughly $300 million distributed back to Eucalyptus employees, the largest ESOP payout in Australian history. He walks through the three questions every founder faces but rarely verbalises: who gets equity, how much, and why you have an ESOP plan in the first place.
You'll also hear how he modelled allocation across multiple rounds and hundreds of hires to avoid giving too much away early, why he personally walked the first two hundred employees through their equity, and why Australia's lack of a secondary market keeps ESOP feeling like monopoly money. Alexey closes with his Big Cojones moment: proposing to his wife, the most nervous he's ever been despite having climbed Europe's highest mountain.
Time Stamps00:00 – Intro
03:01 – The three ESOP questions every founder needs to answer
05:58 – How to model equity allocation across rounds and hundreds of hires
09:10 – Using ESOP as your most powerful recruitment and retention tool
12:02 – How walking 200 employees through their equity built culture and trust
15:02 – Open financials, shrinking cash balances, and what went wrong along the way
17:55 – Why Australia's ESOP ecosystem is still behind Silicon Valley
26:48 – Teaching employees to understand equity: the Google Sheet that started at zero
29:20 – High salary vs heavy equity: giving employees a real choice
32:16 – Common ESOP mistakes founders make and how to avoid them
35:03 – Why Australians treat startup equity like monopoly money
39:11 – The secondary market problem: why liquidity changes everything for ESOP
43:25 – Why your startup career is a portfolio of equity bets
46:36 – What angel investors can do to help portfolio companies build better ESOP plans
Sponsors:First Cheque is supported by our wonderful sponsors:
Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.
It’s why more than 40,000 fast-growing companies trust Deel to move fast.
Visit https://www.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
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
Deel x PX_Script 2
Pear Tree
If you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost.Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business.As a Day One listener, 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.
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Episode Summary
In this 101 episode, Cheryl and Maxine go deep on the fundamentals of pre-seed investing, from how the stage came to exist to why the perceived risk gap between pre-seed and seed is much smaller than most investors think.
They break down the history of how venture stages evolved from single rounds to alphabetized series, how seed investors eventually got pushed up the stack, and why pre-seed emerged around 2017 to 2019 as a distinct category. They unpack why PitchBook's definition of pre-seed as "whatever the investor calls it" muddies the water, how seed preempts from larger funds are inflating average valuations, and why thinking in risk stages rather than round labels is a better framework for evaluating early companies.
You'll also hear why graduation rates from pre-seed to seed don't support the idea that pre-seed is two to three times riskier, why the Australian ecosystem is sitting on a talent surplus with a capital gap at pre-seed, and why this stage is particularly well suited for angels building diversified portfolios of 20 to 40 companies. Cheryl shares her framework for evaluating pre-seed opportunities through the lens of problem pain, frequency, and market size, and Maxine walks through how to think about return profiles, dilution, and valuation at a stage where there are no outputs to measure.
Time Stamps00:00 Intro
01:56 – A brief history of venture stages: how pre-seed became a thing
07:14 – Why round labels are broken and risk stages are a better framework
09:23 – Seed preempts: how big funds are blurring the line between pre-seed and seed
11:48 – Is pre-seed actually riskier than seed? The case that it's not
16:41 – Graduation rates: what the data says about pre-seed to seed conversion
22:59 – Valuation dynamics: what pre-seed rounds look like in Australia vs the US
28:36 – Why Australian founders are leaving for the US at pre-seed and what that means
31:29 – How to evaluate pre-seed companies: inputs over outputs
35:05 – Cheryl's pain framework: frequency, intensity, and willingness to pay
38:28 – Why pre-seed is the best stage for diversifying who gets funded
43:44 – The AI revenue problem: why getting in early matters more than ever
Sponsors:First Cheque is supported by our wonderful sponsors:
Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.
It’s why more than 40,000 fast-growing companies trust Deel to move fast.
Visit https://www.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
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Episode Summary
Noga Edelstein is the lead of the Equity Clear initiative, a not-for-profit effort to get Australian investors tracking pipeline diversity data with a common standard. She's also a former General Counsel at Yahoo, a multi-time founder, and has had her fingerprints across the Australian startup ecosystem for over a decade.
In this episode, Cheryl and Maxine unpack why pre-seed funding to women is at its lowest level ever and how Equity Clear is building the data infrastructure to finally see where diverse founders are falling out of the pipeline. Noga shares what the UK's five-year head start has revealed, including that angel groups with at least 15% women invest in 10X the number of women-led companies, and why the mere act of tracking your own pipeline drives better outcomes.
You'll also hear how a broken website form accidentally proved that women disproportionately use cold inbound to reach investors, why male founders and LPs should be asking their investors about diversity tracking, and what sport can teach us about leveling the playing field through systemic tweaks like funded childcare for founders. Noga closes with her Big Cojones moment: quitting her General Counsel role at Yahoo with a newborn to go all in on a startup.
Time Stamps00:00 Intro
02:27 – Noga's first investment: dollar-mite savings accounts in primary school
10:02 – What is Equity Clear and why pipeline data is the missing piece
14:40 – Why closing the gender gap matters now: productivity, economics, and AI bias
19:27 – Pre-seed funding to women is at its lowest ever despite lower barriers to building
24:44 – Why collecting diversity data feels hard but isn't
28:32 – Lessons from the UK: what five years of tracking has revealed
32:02 – Maxine's accidental experiment: when a broken form hid all the women founders
37:39 – How male founders and LPs can push for change by asking simple questions
48:16 – Why funds are missing a trick on sourcing diverse founders
51:32 – Breaking the archetype: leveling the playing field with systemic tweaks
57:15 – Big Cojones moment: quitting law with a newborn to start a company
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 2
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryElizabeth Yin is the co-founder and General Partner of Hustle Fund, a pre-seed venture fund now on its fourth fund that backs companies globally. Before Hustle Fund, she was a partner at 500 Global, founded adtech company LaunchBit, and was an early employee at Google.
In this episode, Cheryl and Maxine unpack how Hustle Fund sources deals across continents, why Elizabeth avoids noisy competitive markets in favor of "small waves" that will swell over five years, and why valuation discipline matters more than founder pedigree when product-market fit risk is the same at every stage.
You'll also hear how Hustle Fund runs a 30-person team with only four on investments, why Fund 2 was the hardest fund to raise, how the AI wave is creating companies that hit $10M ARR and lose it overnight, and why international valuations still offer significant arbitrage. Elizabeth closes with her Big Cojones moment: being called a "meek Asian woman" by an angel investor while pitching LaunchBit, and how building a platform changed the power dynamic entirely.
Time Stamps00:00 – Intro
01:54 - Elizabeth's first investment: three shares of Coca-Cola at age 10
06:50 – What Hustle Fund is investing in now and why vertical SaaS still matters in the AI era
09:31 – How Hustle Fund sources deals globally through co-investors and content
15:09 – Elizabeth's two-part framework: founder quality vs. idea quality
18:10 – Why competitive markets are a double whammy for small-check investors
22:57 – The surfing analogy: spotting small waves that grow big in five years
25:06 – Biggest investing lessons from Fund 1 to Fund 4: valuation and follow-on discipline
27:58 – Camp Hustle, content marketing, and running VC like a lead generation business
30:09 – Does valuation really matter at pre-seed? When it does and when it doesn't
37:39 – Growing AUM: why Fund 2 was the hardest and the "event ticket sales" fundraising pattern
44:15 – Which fund graduation was hardest and the DPI reality at pre-seed
46:21 – Big Cojones moment: confronting bias as a female founder and how platform changes power dynamics
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryIn this episode of First Cheque, Cheryl and Maxine sit down with Laura Chambers, CEO of @Mozilla to dive into the transformative power of open source technology and its role in shaping the future of the internet and artificial intelligence. Laura shares insights on Mozilla’s unique nonprofit structure, the importance of transparency and accessibility in technology, and the critical need for an open AI ecosystem to drive innovation and equity. From the historical impact of open source software like Firefox to the current challenges of balancing ethical AI development with business needs, this conversation is packed with lessons for early-stage investors and tech enthusiasts alike. Laura also provides an inside look at Mozilla Ventures and the Builders Program, which are supporting the next wave of open-source innovators. Whether you're an investor, founder, or just curious about the future of tech, this episode is a must-listen!
Time Stamps00:00 Intro & Guest Highlights
00:21 Why We're Excited About Laura Chambers
03:14 Interview Begins: Laura's First Investment at Age 10
05:20 Open Source 101: What It Is & Why It Matters
07:08 Firefox vs Internet Explorer: The Open Source Origin Story
09:58 How Healthy Is the Internet Today?
13:50 Can You Actually Make Money From Open Source?
15:45 What If the Internet Had Stayed Behind Paywalls?
17:33 Gen AI Is the New Model T: We're Missing the Seatbelts
19:37 The Case For & Against Closed Source AI
21:35 Why Researchers, Academics & Governments Need Open Access
22:17 Where Are We in the Gen AI Infrastructure Cycle?
24:18 AI in Education: What Skills Do Kids Actually Need?
26:36 Older Generations & the AI Learning Gap
29:16 Open vs Closed: Who's Winning Right Now?
33:49 Meta's Llama & the Strategic Logic of Going Open
35:21 Advice for Founders & Investors Building on Open vs Closed Models
39:21 Inside Mozilla Ventures: What They're Investing In
41:31 Prompt Engineering Tips From a CEO (Say Please!)
46:13 The Biggest Brave Moment: Moving Her Family & a 17-Year-Old Dog to Australia
49:20 The Weight of Being CEO & What That Feels Like
Resources1) Mozilla Ventures: Supporting startups focused on privacy, AI, and open source innovation. (https://mozilla.vc/)
2) Mozilla Builders Program: Investing in and mentoring early-stage entrepreneurs building ethical tech solutions. (https://builders.mozilla.org/)
3) Harvard University Study: Open Source Software’s $8 Trillion Economic Impact A study on the global economic value created by open source technology. (https://www.hbs.edu/ris/Publication%20Files/24-038_51f8444f-502c-4139-8bf2-56eb4b65c58a.pdf)
4) Anthropic Report on Bias in AI: Research highlighting the impact of bias and the importance of transparency in AI models. (https://www.anthropic.com/research/mapping-mind-language-model)
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryFrontline’s Brennan O’Donnell has spent two decades helping companies expand across borders, first as an operator at Google and later as a growth investor backing Series B to D businesses. In this episode, Cheryl and Maxine unpack what’s shifted at growth stage in the last 12 months, why the market is still a barbell of “hot or not” deals, and how AI is finally producing application layer companies mature enough for growth rounds.
They go deep on Frontline’s transatlantic model: seed investing across Europe to help founders raise a Series A and enter the US earlier, and growth investing in the US to help companies expand into Europe with a hands on, concentrated portfolio approach. Brennan breaks down the four pillars Frontline uses to drive international expansion timing, go to market, talent and org design, and location plus the biggest traps founders fall into, like trying to launch in too many markets at once or optimizing for revenue targets instead of learning.
You’ll also hear why the UK and Ireland are the default first step for 97 percent of US companies entering Europe, when Europe becomes a CEO level priority, how relationship driven sales cycles vary across countries, and why developer led community building can beat traditional sales led expansion for certain AI products. Brennan closes with his Big Cojones moment: moving to the Bay Area for a temporary Google job with everything in storage, then doing it again to help build Google’s European HQ in Dublin.
Time Stamps03:14 Brennan’s first investment: Mode Analytics and a lawn mowing business in Texas
06:49 What’s changed at growth stage and why “growth” is a different world
08:30 Why AI enablement came first and app layer is finally ready for Series B plus
10:10 The new risk: fast revenue that’s concentrated and not yet durable
14:22 Frontline’s model: Europe seed plus US growth and why it’s unique
15:58 What Frontline looks for: category leaders and a line of sight to a 5x outcome
16:20 The rough revenue range where growth starts paying attention
23:22 The four pillars of expansion: timing, go to market, talent, location
26:00 Timing: the 10 percent pull, exec maturity, and why waiting too long is risky
29:36 Why Europe expansion has to be a CEO level company priority
38:04 Build or buy: why most companies compete into new markets rather than acquire
39:10 Developer community expansion as a new go to market wedge
41:44 Market selection: why nearly everyone starts with London or Dublin
43:56 “Success amnesia” and why you must optimize for learning not quotas
48:28 Relationship driven sales cycles and how Europe varies market to market
52:43 Big Cojones moment: taking a temp Google job and betting on himself
54:26 Doing it again: moving to Dublin in three weeks to help build Google Europe
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Episode Summary
As 2026 kicks off, Cheryl and Maxine open the year with their annual First Cheque wrap, a grounded, opinionated take on what actually shifted in Australian tech and venture, and what that means for the year ahead.
They break down why 2025 marked a genuine inflection point for the ecosystem, from Canva’s secondary and a surge in M&A to fresh signals that long-awaited liquidity is finally starting to flow. Despite minimal government support, Australia quietly proved itself as one of the most capital-efficient venture markets globally, producing unicorns at roughly twice the rate of the US per dollar invested.
The conversation also tackles the harder truths investors and founders need to reckon with in 2026: early-stage funding compressing while late stage heats up, corporate venture capital retreating, and the gender funding gap sliding backwards. Looking forward, Cheryl and Maxine share their predictions for the year ahead, where funding volumes may land, why seed remains the toughest stage, how AI valuations could trigger a market correction, and why energy and infrastructure may emerge as the next premium asset class.
Time Stamps00:00 – Intro: End of year energy: why 2025 felt different to 2024
03:55 – Election fallout and the government’s “nothingburger” for startups
05:24 – Canva’s secondary and the first real signs of liquidity returning
09:49 – Aussie tech M&A heats up: Canva, Linktree, Jolt, and more
12:09 – The stat that changed the narrative: Australia’s unicorn efficiency
16:14 – The weirdest trend of the year: early stage down, late stage up
18:27 – Tech jobs, data centers, and the infrastructure bet Australia is making
22:52 – Why deep tech and climate are pulling venture dollars again
28:21 – The gender funding gap got worse (and why)
33:09 – Corporate VC is pulling out: what happened to strategic capital
37:02 – 2026 predictions: funding totals, seed pain, and where capital flows next
44:00 – AI bubble risk: tourism, ROI pressure, and the domino effect
47:42 – Hot take: electricity is the next valuation premium
49:00 – Will diversity bounce back in 2026? (vibes, but also logic)
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Episode Summary
Max Kausman is the founder and solo GP of Advance VC, Australia's first dedicated fund-of-funds with a focus on secondaries.
Advance VC buys existing positions in Australian and New Zealand VC funds—acquiring stakes from investors seeking liquidity and giving new LPs diversified access to mature, validated portfolios across multiple vintages dating back to 2012.In this conversation, they discuss why secondaries won't "save" all of venture (only the top performers), how discounts actually work (spoiler: the average is 30-35% but it's wildly bespoke) and why vintage diversification matters as much as portfolio diversification.
Time Stamps02:47 – Max's first investment: lessons as a 14-year-old basketball coach
07:08 – Defining secondaries and Advance VC's unique LP fund focus
09:44 – Why vintage diversification matters as much as company diversification
13:57 – How secondary transactions actually work: the three-way deal between buyer, seller, and fund
19:24 – What Max learned looking under the hood of Australian VCs firms across different funds and vintages
24:09 – Why Max decided on a secondary Fund of Funds (FoF) model
34:16 - Pricing secondaries
42:20 – What discounts actually look like in practice
47:40 – Will secondaries save venture? The truth about liquidity and why it's concentrated in top performers
50:16 – Building Advance VC and the founder journey of becoming a fund manager
ResourcesMax Kausman - https://www.linkedin.com/in/maxkausman
Advance VC - https://www.advancevc.com/
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryMatt Browne is the Co-founder and Managing Partner of Black Nova Venture Partners, one of Australia’s most active early-stage funds. Before becoming an investor, Matt founded multiple companies, including enterprise software firm Dunsafe, which sold to global corporates like Suncorp and Brickworks, and learned firsthand what it takes to turn “boring” B2B SaaS into beautiful business.
In this episode, Cheryl and Maxine sit down with Matt to unpack what “boring but mission-critical” really means, why operators often make the best early-stage investors, and what it’s actually like to co-found a venture fund. Matt shares his frameworks for identifying resilient software businesses, the economics behind long-LTV enterprise customers, and how his founder experience shapes the way Black Nova supports startups today.
They also dig into the differences between SMB and enterprise sales, why going from enterprise → small business is nearly impossible, and what it takes to build a fund that’s more startup than finance firm. And, in true Matt style, he caps it off with his Big Cojones moment, jumping off Auckland’s Sky Tower to win a customer.
Sponsors:First Cheque is supported by our wonderful sponsors:
Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.
It’s why more than 40,000 fast-growing companies trust Deel to move fast.
Visit https://www.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
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryWhat happens when hundreds of the world’s biggest capital allocators get together behind closed doors to talk about venture, private equity, and where the next $30B is going? Maxine found out firsthand at Super Returns Asia, where she chaired the LP–GP relations stage.
In this episode, Cheryl turns the tables and grills Maxine on everything she learned, from why India and Japan are suddenly hot, to why Southeast Asia is struggling, and why Australia didn’t even make the winners or losers list.
They break down how institutional investors really think about funds, what “look-through ownership” means for angels and VCs alike, and why co-investing has LPs hot under the collar. Maxine also shares how family offices are thriving in the current market, what mega-funds like a16z’s $30B raise mean for everyone else, and why building long-term LP relationships is the only real way to get “super returns.”
Time Stamps01:00 – What Super Returns is, and why it matters for VCs and angels
06:43 – The LP landscape explained: super funds, sovereign wealth funds, and family offices
10:40 – Winners and losers in APAC: India, China, Japan… but not Australia
18:00 – Why Australia needs a better “brand story” to attract capital
19:54 – Hot topic: co-investing and why LPs love it
23:39 – Look-through ownership: why everyone’s just trying to own the outliers
26:43 – Why emerging managers are struggling in today’s fundraising market
33:49 – Family offices having “the time of their lives” in this cycle
34:23 – Mega-funds, evergreen funds, and the $30B a16z raise
39:30 – Will Sequoia and a16z ever lose their dominance?
42:19 – Why APAC liquidity markets matter more than ever
45:30 – The question nobody asked at Super Returns
49:22 – How to actually build LP relationships that work
53:55 – Maxine’s big takeaway: putting Australia on the winners list
Sponsors:First Cheque is supported by our wonderful sponsors:
Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.
It’s why more than 40,000 fast-growing companies trust Deel to move fast.
Visit https://www.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
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummarySachin Bhanot leads Southeast Asia & ANZ investments at Prosus Ventures, a global fund with $100B+ in assets. Though based in Singapore, Sachin has become an “honorary Australian fund manager”, with nearly half of Prosus’s regional portfolio now in Australia and New Zealand.
In this episode, Cheryl and Maxine dive into why Prosus ramped up in Australia during a downturn, what paradoxical traits they see in winning founders, and how Singapore and Southeast Asia really compare as markets for expansion.
They unpack the playbook for Australian startups going regional, what Singaporean family offices are actually looking for, and why relationship-building is the real cheat code in Southeast Asia. Sachin also shares his biggest Big Chon moment, and how building coffee chains in the Philippines and Malaysia reshaped his view of what it takes to be an investor.
Time Stamps02:53 – Sachin’s first and most important investment (hint: not a startup)
07:31 – The paradoxical traits of winning founders
10:26 – Singapore vs Southeast Asia: the tale of two ecosystems
18:12 – Why Prosus doubled down on Australia in 2022
28:40 – Tips and traps for Aussie founders expanding regionally
34:44 – When is the “right” time to enter Southeast Asia?
42:11 – The rise of the Australia–India–Singapore innovation corridor
48:34 – Singapore family offices and the art of relationship-driven capital
51:59 – Sachin’s Big Chon moment: learning empathy by building businesses himself
ResourcesResources Mentioned
🙋🏻♂️ Sachin Bhanot - https://www.linkedin.com/in/sachin-bhanot-15551913a/
💰 Prosus Ventures - https://www.prosus.com/prosus-ventures
Sponsors:First Cheque is supported by our wonderful sponsors:
Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.
It’s why more than 40,000 fast-growing companies trust Deel to move fast.
Visit https://www.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
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryTom Humphrey, Partner at Blackbird and former operator, joins Cheryl and Maxine to reframe the conversation around Australia’s AI ecosystem. While headlines paint a picture of Australia falling behind, Tom argues we’re quietly sitting on world-class talent, global-first AI companies, and a capital-efficient edge that’s being overlooked.
They unpack Tom’s recent AFR opinion piece on the AI talent landscape, why Australia’s university-to-startup pipeline is broken (and slowly improving), and how “boomerang” PhDs are returning from Anthropic, Meta, and DeepMind to build ambitious companies onshore. Plus, Tom breaks down how product-led growth is evolving in the AI era, why enterprise motions are happening sooner, and what the new GTM playbook looks like when AI agents are selling to AI agents.
Time Stamps02:21 – Tom’s first investment: BHP shares via his parents, now passing on the habit to his son
05:19 – Robinhood, meme stocks, and the shift to founder-led brands
07:06 – Why Tom wrote the AFR piece: Australia’s culture of doubt vs the US lens of opportunity
08:08 – Australia’s untapped AI talent advantage: 8% of APAC experts, top-tier unis, and PhD immigration
12:18 – Six model releases, global leaderboard wins… that no one in Australia talks about
14:03 – The dangerous cost of silence: how lack of domestic celebration dampens ambition and capital
17:33 – Why Australia is absurdly capital-efficient (and how we squeeze every dollar)
19:23 – Commercialisation bottlenecks at Aussie unis, and what’s slowly changing
25:39 – How this affects investors: AI engineering vs AI research, the boomerang effect, and talent arbitrage
30:56 – Time zones, USD revenue, and Australia’s secret weapon: the 43% R&D tax credit
33:17 – Role gaps and brand new roles: the rise of AI architects and forward deployed engineers
34:27 – What PLG really means, and why it’s not just a freemium sign-up form
39:31 – Spammy AI agents, SEO collapse, and why brand and community are back
45:15 – Why enterprise motions are showing up earlier (and how that changes GTM)
48:32 – Single-player AI value unlocks a different sales motion: fast, bottom-up adoption
51:15 – AI fits into your workflow, not the other way around
54:14 – Picking your motion: don’t force PLG if it’s not a natural fit
55:05 – Capital-starved ecosystems and why enterprise is still harder to fund in Aus
56:15 – Tom’s Big Cojones moment: three boys under six and a startup-founder partner
Resources👤 Tom Humphrey LinkedIn – https://www.linkedin.com/in/tomhumphrey1/
🚀 Blackbird Ventures – https://blackbird.vc/
Sponsors:First Cheque is supported by our wonderful sponsors:
Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.
It’s why more than 40,000 fast-growing companies trust Deel to move fast.
Visit https://www.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
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
Aussie Angels - the preferred fund and syndicate admin platform for emerging managers in Australia
Show Notes: If you’re an investor or keen to write your first angel check, please check out some of the syndicate tickets on www.aussieangels.com
February 2025 - Aussie Angels
This podcast uses the following third-party services for analysis:
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Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryIn this crossover episode of First Cheque and In The Blink of AI, Cheryl Mack (Aussie Angels) and Maxine Minter (Co Ventures) team up with host Georgie Healy to unpack how investors are thinking about AI, beyond the hype. From pitch decks to product demos, they reveal the frameworks and gut checks they use to spot real value in AI startups, even when they’re not technical experts themselves.
You’ll also get a behind-the-scenes look at how Cheryl and Maxine are integrating AI into their own workflows, not just as investors, but as operators. From using ChatGPT to summarise founder meetings, to leveraging Prompt Cowboy and NotebookLM for due diligence and research prep, they walk through real examples of how AI is saving them time, sharpening decision-making, and helping them stay ahead in deal flow. And yes, we finally answer the question: what is an agent… and does anyone actually have one?
Time Stamps02:15 – Are Cheryl and Maxine AI skeptics or advocates?
06:00 – What's actually fueling the AI hype?
10:45 – Are we in a bubble—or just early in the cycle?
16:20 – Valuations, FOMO, and how investors are pricing AI
21:00 – What angel investors should look for in AI startups
27:30 – AI’s biggest red flag: When it all just sounds like magic
31:00 – Are agents real or is everyone faking it?
36:40 – AI in venture workflows: What Maxine actually automates
41:30 – The real power of personal brand in VC
44:50 – How Cheryl preps for founder calls with Google NotebookLM
49:00 – Weekly AI hacks: From flat lays to voice-mode strategy sessions
52:10 – Founder FOMO: Prompt Cowboy, Juno, and other hot startups
54:00 – The case for non-technical founders in AI
58:00 – Are one-person billion-dollar startups real?
Resources😇 Angel Academy: The most comprehensive angel investing course for Australia & NZ – www.venture.academy
🦘 Aussie Angels: Cheryl’s platform for angel investing – https://www.aussieangels.com/
💰 Co Ventures: Maxine’s venture capital firm – https://www.coventures.vc/
Sponsors:First Cheque is supported by our wonderful sponsors:
Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.
It’s why more than 40,000 fast-growing companies trust Deel to move fast.
Visit https://www.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
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
Angel Academy - Best online angel investing course in Australia and New Zealand
Don't forget to check out the best online angel investing course in Australia and New Zealand, Angel Academy. It's fun, engaging, and packed full of insights from experienced investors to help you get started or level up your angel investing, visit www.venture.academy
February 2025 - Angels Academy
This podcast uses the following third-party services for analysis:
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Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummarySome investor phrases sound helpful. Others feel like a riddle. In this episode, Cheryl and Maxine crack open the language investors use when talking to founders, and translate what’s actually being said behind phrases like “not a fit,” “too early,” or “let’s have one more meeting.”
They walk through the subtle (and not-so-subtle) cues that signal a pass, explain what “conviction” actually means in VC-speak, and share tactics founders can use to get clearer answers during fundraising. You’ll also hear the behind-the-scenes realities of ghosting, deal timelines, internal partner politics, and why “we’d love to stay close” usually means… they won’t.
Plus: a rapid-fire rundown of the weirdest (and most cringe) investor slang, from “due dilly” to “foundies.”
Whether you’re raising your first round or managing investor relationships post-close, this episode helps you spot the signals, ask better questions, and avoid wasting time.
Time Stamps01:45 – “Not a fit”: Why investors love this vague phrase
03:40 – What they mean when they say “you’re too early”
08:30 – “You’re too late”, how stage mismatches work both ways
15:30 – “We’ll circle back” and other signs of a slow no
17:10 – How long does VC diligence really take?
19:15 – Why June 30 is a terrible time to raise
24:10 – Optionality: The excuse behind “we love what you’re doing”
28:00 – “Let the lawyers sort it out”: A red flag or not?
30:15 – The weirdest investor slang (please don’t say “due dilly”)
33:30 – Term sheet vs. side letters: what’s actually worth negotiating
36:00 – Understanding info rights vs. investor updates
38:50 – How to share bad news without burning relationships
45:20 – The shifting goalposts of traction and growth metrics
47:00 – Spotting investor doubts through team questions
48:10 – Final thoughts for both founders and investors
Resources😇 Angel Academy: The most comprehensive angel investing course for Australia & NZ – www.venture.academy
🦘 Aussie Angels: Cheryl’s platform for angel investing – https://www.aussieangels.com/
💰 Co Ventures: Maxine’s venture capital firm – https://www.coventures.vc/
Sponsors:First Cheque is supported by our wonderful sponsors:
Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.
It’s why more than 40,000 fast-growing companies trust Deel to move fast.
Visit https://www.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
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryCharles Hudson is the Founder and Managing Partner at Precursor Ventures, a solo GP fund that has backed over 450 startups across five funds, including dozens of category-defining companies led by underrepresented founders. In this episode, Maxine and Cheryl sit down with Charles to explore how he built one of the most successful high-volume venture strategies in the world, all while staying a solo decision-maker.
They dive deep into what being a “solo GP” actually means, how Charles balances scale with intimacy across a massive portfolio, and why trust, not likability, is his north star when supporting founders. You’ll also hear his first-ever investment, the courage it took to leave a top-tier firm to start Precursor, and how he still handpicks every company Precursor backs, often long before they’re obvious.
Time Stamps03:20 – Charles’s first investment: ExxonMobil shares… mailed by cheque
06:50 – What is a solo GP fund, and how Precursor operates with one partner and 14 staff
10:28 – The pros and cons of solo decision-making in venture
12:50 – How Precursor supports 450+ companies (and avoids “orphaned” portfolios)
15:44 – Why Charles shifted from unlimited founder support to intentional check-ins
19:18 – Trust vs likability, and why real feedback matters more than being liked
24:25 – How Charles handles saying “no” to follow-ons, and still earns trust
29:31 – The case for “challenger” VCs over cap-table cheerleaders
32:11 – What Precursor looks for in a founder: not great employees, but great CEOs
36:39 – High volume investing: Why meeting 2000+ startups matters
39:00 – Global allocation: why Charles bet early on African and LatAm FinTech
42:30 – The return of themes (like AI & Women’s Health), and why they can kill judgment
47:52 – When Precursor steps in (and when they don’t): being the “surgeon, not the bandaid”
54:04 – Charles’s biggest Big Cojones moment: leaving Uncork to build Precursor from scratch
56:15 – Why most fund managers are “post-employment” and proud of it
Resources👤 Charles Hudson LinkedIn - https://www.linkedin.com/in/chudson/
🌎 Precursor Ventures – https://precursorvc.com/
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Grab your copy of the Dealroom and SideStage Ventures report we talked about on the show with Cheryl Mack and Maxine Minter here - https://www.sidestage.vc/outliers-report-2025
Episode SummaryBen Grabiner is the Co-founder and General Partner at Side Stage Ventures, and the author of a landmark new report in collaboration with Dealroom and AWS. In this episode, Cheryl and Maxine sit down with Ben to unpack the data behind Australia’s rapid rise as one of the most efficient and exciting venture ecosystems in the world.
They explore how Australia produces more unicorns per dollar invested than any other country, what makes the ecosystem so resilient and capital-efficient, and why the next decade might belong to Aussie tech. From funding gaps to founder grit, from global capital flows to angel investor opportunities, this is essential listening for allocators, founders, and emerging fund managers alike.
You’ll also hear Ben’s story, from buying Tottenham Hotspur shares as a teenager, to moving across the world mid-COVID, to becoming a key builder in Australia’s startup ecosystem.
Time Stamps04:49 – Ben’s first investment: £250 in Tottenham Hotspur
06:34 – What makes Australian unicorns so capital-efficient?
09:14 – Unicorn efficiency vs gross unicorn creation: what matters more
13:15 – How Australia quietly matches Israel and India on decacorn creation
14:35 – Why foreign investors see the opportunity more clearly than locals
18:41 – The power of local exits like Afterpay, and how they inspire allocation
21:19 – Can Aussie startups scale globally from home? Or must they go abroad?
23:40 – Why this next wave of operators will be our ecosystem’s secret weapon
25:54 – What global LPs need to understand about Australian venture
30:17 – Why pre-seed funds and angel investors matter more than ever
Resources🙋🏻♂️ Ben’s LinkedIn - https://www.linkedin.com/in/bengrabiner/
💳 Side Stage Ventures - https://www.sidestage.vc/
🦘 Aussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence.
https://www.aussieangels.com/
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/ -
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryNnamdi Okike is the Co-founder and Managing Partner at 645 Ventures, known for his early, contrarian bets on overlooked verticals and non-obvious industries. In this episode, Nnamdi shares how he leveraged a data-driven sourcing model to identify breakout companies like Squire and Goldbelly, and why seemingly small or niche markets often produce the biggest wins. Maxine and Cheryl dive deep into Nnamdi’s journey from Insight Partners analyst sourcing deals via cold calls, to launching his own fund and achieving a remarkable hit rate, landing him on the Midas Brink List. They explore how he evaluates founder insights, measures market inflection points, and strategically navigates the power law dynamics in venture capital. Packed with strategic insights and candid reflections, this episode is essential listening for emerging investors, fund managers, and founders curious about building defensible businesses in non-obvious spaces.
Time Stamps04:34 – Nnamdi’s first investment during the dotcom boom
06:52 – Defining “non-obvious industries” and spotting hidden TAM
10:40 – Squire: From barbershop bookings to vertical SaaS OS
13:20 – Goldbelly, marketplaces, and the power of founder insight
17:58 – Algorithmic sourcing meets founder conviction
21:30 – What 645 Ventures learned from missing Facebook
26:46 – Building a fund around risk profiles, not just stages
30:34 – Why the power law should shape every VC decision
35:16 – Does 2024 echo 2002? A macro take on the downturn
42:41 – The rise of zombie funds and quiet closures
45:20 – Bootstrapped AI startups and the future of defensibility
52:54 – When vertical AI gets sticky—and when it doesn’t
57:20 – Nnamdi’s Big Cojones moment: from Insight to starting fresh
Resources🙋♂️ Nnamdi Okike on LinkedIn – Follow Nnamdi’s updates and insights. https://www.linkedin.com/in/nnamdiokike
💰645 Ventures – A VC firm investing in early-stage, non-obvious software winners. https://645ventures.com/
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
This podcast uses the following third-party services for analysis:
Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
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Episode SummaryPocket Sun is the Founding Partner at SoGal Ventures, the first female-led, millennial VC firm investing in the future of living, working, and staying healthy. In this episode, she shares how she made her first angel investment at just 24, and how her early bets like Everly Health and Lovevery reflected a conviction in underrepresented founders well before it was a trend. Cheryl and Maxine explore how Pocket launched SoGal’s debut fund, built a deal pipeline through global pitch comps and community, and mastered the art of getting onto oversubscribed cap tables. They also unpack her consumer investing thesis, how she’s navigating fund two with more geographic focus, and what it means to lead recaps and board restructures when the power law turns brutal. For anyone curious about building a fund from scratch, going global with limited resources, or backing change-makers the market misses, this episode is packed with both tactics and courage.
Time Stamps00:00 – Pocket’s first angel check: $1K into an AI startup
05:30 – Angel investing isn’t just for the ultra-wealthy
09:45 – From building a global pitch comp to proving LP credibility
14:20 – Early wins: Everly Health, Lovevery, and chasing allocation
23:35 – “Land and expand”: getting on cap tables and earning super pro-rata
27:10 – Leading recaps and fighting for underestimated founders
35:00 – SoGal’s thesis: The future of living, working, and staying healthy
40:30 – Entering new verticals without prior expertise
46:00 – Pocket’s take on the Vancouver vs. Toronto startup ecosystems
53:00 – Betting on design-led, intentional consumer businesses
59:10 – Why consumer startups often graduate into enterprise giants
01:03:00 – Pocket’s Big Cojones moment: moving solo to the U.S. at 18
Resources🙋♀️Pocket Sun on LinkedIn – Connect with Pocket and follow her updates. https://www.linkedin.com/in/pocket
💰SoGal Ventures – A VC firm backing diverse founders in the future of living, working, and staying healthy. https://www.sogalventures.com/
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