Isaiah pivoted mid-YC, landed in the bottom 10% of his batch, and watched 180 investors say no—their reason: phone calls won't exist a year from now. Voice AI was not yet a thing. With almost no money left, he and his co-founder bet everything on building AI phone calls from scratch. Bland went from pre-seed to a $40M Series B in a year.

In this episode, Isaiah breaks down how a $60K billboard and a strategic influencer campaign generated close to a billion impressions, why he fired 50% of his customers right after raising a Series A, and the enterprise sales playbook that lands six- and seven-figure contracts with companies most people have never heard of.

Why You Should Listen

Why 180 VCs saying your market won't exist is actually a bullish signal.
How two billboards and a wave of micro-influencers generated a billion impressions.
Why firing half your customers right after raising your Series A can save your roadmap.
How internal newsletters and org-chart mapping win six-figure enterprise deals.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, voice AI, AI phone calls, enterprise sales, Bland AI, YC pivot, billboard marketing, influencer marketing, call center automation, Isaiah Granet

Chapters

00:00:00 Intro
00:02:34 A Typhoon Replaces an Entire Call Center
00:11:52 The YC Pivot and 180 Rejections
00:19:05 Betting the Company on In-House AI
00:24:11 The Billion-Impression Billboard Campaign
00:34:49 Firing 50% of Customers After Raising $20M
00:38:43 The Enterprise Sales Playbook
00:50:52 The Moment of True Product Market Fit

Send me a message to let me know what you think!

The winners and losers in advisor recruitment

This Week in Wealth

Intro

The AI-powered Podcast Player