Frontline’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.

03:14 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

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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.

00:00 – 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)

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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.

02:47 – 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

Max Kausman - https://www.linkedin.com/in/maxkausman

Advance VC - https://www.advancevc.com/