June 12, 2025

This One Hire Nearly Killed My Business | Pat Killoren - E60

This One Hire Nearly Killed My Business | Pat Killoren - E60

What happens when a startup sales pro burns out and decides to start a podcast? In this episode of Funds and Founders, we sit down with Pat Killoren — host of Lone Startups who shares his wild journey from scaling beer brands and influencer platforms to building community-led content in Austin.

🎙 We go deep into:

  • Building sales teams as a founder
  • The mistakes startups make in GTM strategy
  • Burnout, pivots, and personal reinvention
  • How to monetize podcasts through real partnerships (not just ads)

Whether you're a builder, creator, or investor, this episode will leave you with tangible lessons on growth, niche branding, and sustainable success.

TIMESTAMPS:

00:00 – Intro: Who is Pat Callaghan?

01:00 – Why he chose Austin and non-tech founders

03:30 – His journey from beer to blockchain

06:00 – What is Go-To-Market ?

08:00 – The Enterprise Trap: Why startups jump too soon

10:00 – How scrappy founders should build sales

14:30 – Why you shouldn’t send proposals too early

16:00 – How founders waste time chasing the wrong customers

18:00 – Picking the right channels: The Web3 sales story

21:00 – Cold outreach vs sniper sales: What works today

23:00 – How to hire your first sales hire (without getting burned)

25:00 – Why he quit sales and started a podcast

28:00 – The admin pain of podcasting no one talks about

30:00 – The monetization struggle: why brands hesitate

32:00 – Seasons vs weekly: how he’s structuring Lone Startups

36:00 – Format talk: from nature podcasts to 3D LED sets

40:00 – Roundtable format: a future idea for deep-dive episodes

44:00 – The mental blocks of podcast production quality

46:00 – Tools + Tech Stack for running the show

52:00 – Why video editing has become his new obsession

54:00 – Question for the next guest

56:00 – Where to follow Pat & closing thoughts