Jacob Ross on Trusting Yourself and Building the Business You Can See

Jacob Ross is the CEO of PebblePost, a performance marketing company that pioneered programmatic direct mail. In this episode, Jacob shares the critical moment in 2021 when PebblePost tested the market for a sale and what he learned about investor signals, category perception, and the gap between a good business and a great opportunity. The decision not to sell turned into a major strategic pivot that would define the company’s next chapter: launching a CTV product and redefining their identity beyond direct mail.

🎯 Keywords: PebblePost, programmatic direct mail, CTV, performance marketing, investor relations, strategic pivots, founder transition, CEO coaching

⏱️ Timestamps:

00:00 – Jacob joins from the Upper West Side (and Orwashers)

03:10 – Life update: twins, camp, and nomadic futures

07:15 – PebblePost’s pitch and the “What kind of company is this?” question

10:45 – Going to market: the failed-but-successful sales process

14:25 – The realization: narrative isn’t enough, business reality matters

18:00 – Strategy shift: from direct mail to full-funnel performance marketing

23:45 – Launching CTV and realigning the team

31:10 – What it means for employees to feel the vision

36:20 – What CEOs can learn from this: trust yourself

38:10 – The impact and memory of founder Lewis Gersh