After raising money from VCs, Aleem Mawani (@aloo) chose a path that most VCs would consider a failure: to turn his company, Streak, into a large, profitable, and lasting software business. To do so, he'd have to pivot away from a failing idea, start charging customers who'd always been free, and bet everything on a risky platform controlled by another company. But today he's never been happier. In this episode, Aleem and I discuss when to work harder vs when to call it quits, how to pick the right community to surround yourself with, and how he chose a SaaS idea that scaled to millions in revenue.

• Streak, Aleem's CRM for Gmail: https://www.streak.com
• Follow Aleem on Twitter: https://twitter.com/aloo