Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey

Episode Summary

Yotam Rosenbaum never planned to be a startup founder, let alone one of Australia’s most active investors in Y Combinator companies. He started out as a musician, marketing his own band in Los Angeles, until the frustration of promoting music online became the spark for building Earbits, a platform once described as “Google AdWords for music.” What began on a traffic-jammed freeway turned into a five-year journey through Y Combinator, product-market chaos, and a successful exit.

Since then, Yotam has backed over 400 YC startups, built one of the only Australian-led funds inside the program, and helped founders at home think far beyond local markets. He reflects on what actually matters at the earliest stages, why founder relationships trump early traction, and how to spot the quiet signals of a breakout team. There’s also a reality check for anyone raising capital: most investors won’t give you a clear no, and that’s the real cost.

From Craigslist drum lessons to portfolio unicorns, Yotam’s story is anything but typical. But it’s proof that trusting your sense of direction, without needing the whole map, can still get you somewhere remarkable.

Time Stamps

00:01:17 – Embracing Uncertainty: Yotam’s Philosophy on Direction Without a Map

00:06:41 – From Funk Band to Founder: The Origins of Earbits

00:11:05 – The Aha Moment: Building the Google AdWords for Music

00:14:58 – Joining Y Combinator: Early Traction & Getting In

00:20:04 – Life at YC: Feeling Out of Place, Finding Belonging

00:24:29 – Investing in 400+ YC Startups: How It Started Post-Exit

00:31:19 – Moving to Australia: The Hot DesQ Bet That Paid Off

00:36:35 – Comparing Ecosystems: SF vs Brisbane Startup Mindsets

00:41:09 – The Importance of Community: No Founder Builds Alone

00:45:39 – The 77 Partners Venture Challenge: Who It’s For

00:50:24 – What Investors Look For (It’s Not Just Revenue)

01:03:01 – How Founders Can (And Should) Think About AI

Resources Mentioned

🥇 First Peak Ventures - https://www.linkedin.com/company/first-peak-ventures/

🤝 77 Partners – http://www.77partners.vc/

🙋🏻‍♂️ Yotam Rosenbaum on LinkedIn – https://www.linkedin.com/in/yotamrosenbaum/

👂🏻 Earbits – https://www.earbits.com/

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

To learn more, join our newsletter to be notified of new Perspective X episodes and upcoming shows.

Mentioned in this episode:

Vanta_PX_May 2025

Mighty Partners_PX_May 2025

Deel x PX_Script 1