Episode Summary

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.

Time Stamps

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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