The Official SaaStr Podcast: SaaS | Founders | Investors

The Official SaaStr Podcast: SaaS | Founders | Investors

SaaStr 172: Why It Is Easier To Start In SMB and Work Your Way Up, How To Encourage A Risk Mindset Into Your Culture & How To Separate Ego From Decision-Making with Jon Lee, Founder & CEO @ ProsperWorks

Apr 23, 2018 · 24:09

Listen to Episode

✨ AI Summary

Starting with SMB and scaling up is often easier.
Fostering a culture that embraces calculated risk-taking.
Separating personal ego from critical business decisions.

Guests on This Episode

JL

Jon Lee

1 podcast appearance

More from The Official SaaStr Podcast: SaaS | Founders | Investors

SaaStr 848: How AI Is Rewiring Sales: Quota, Retention & What's Actually Working with SaaStr, Salesforce and Mangomint

Apr 1, 2026 · 42:56

SaaStr 847: How MangoMint Increased Win Rates with an AI-Powered Stack

Mar 25, 2026 · 31:28

SaaStr 846: 10 Things to Know Before You Deploy Your First AI SDR with SaaStr's CEO and CAIO

Mar 18, 2026 · 01:05:48

SaaStr 845: How SaaStr Built a $5 million Pipeline Machine with 1.5 Humans and 20 AI Agents with SaaStr's Chief AI Officer and Momentum from Salesforce's VP of GTM

Mar 11, 2026 · 41:25

View all episodes →