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.