Sales Secrets, Startup Wins & Leadership Fails — Kevin Gaither Gets Real episode artwork

EPISODE · Mar 28, 2025 · 39 MIN

Sales Secrets, Startup Wins & Leadership Fails — Kevin Gaither Gets Real

from Happiness by Habit · host Silvana Pimentel

In this Happiness by Habit episode, Silvana Pimentel dives deep with sales legend Kevin Gaither—a startup OG with 25+ years in the game, eight startups, and three successful exits.But this isn’t your average “sales tips” convo. Kevin pulls back the curtain on what actually works when building and scaling sales teams—and the mistakes that almost cost him everything. From trying to be friends with employees to why most founders fail at hiring salespeople (and how to avoid it), this episode is loaded with straight-talk, strategy, and surprising truths.We talk:The ONE mistake that nearly sank Kevin’s early leadershipWhy “urgency, respect, and transparency” scale better than KPIsHow to use AI in sales without sounding like a botThe sales advice every technical founder needs to hear (ASAP)The books that rewired Kevin’s mindset for growth🎧 Whether you're a founder, a sales lead, or just obsessed with personal growth—this one's for you.📘 Free Sales Leadership Guides by Kevin Gaither:👉 Download Now🔗 Kevin on LinkedIn:👉 https://www.linkedin.com/in/kevingaither💼 Connect with Host Silvana Pimentel:👉 www.linkedin.com/in/silvana-pimentel1🔗 Connect with Kevin & Silvana

In this Happiness by Habit episode, Silvana Pimentel dives deep with sales legend Kevin Gaither—a startup OG with 25+ years in the game, eight startups, and three successful exits.But this isn’t your average “sales tips” convo. Kevin pulls back the curtain on what actually works when building and scaling sales teams—and the mistakes that almost cost him everything. From trying to be friends with employees to why most founders fail at hiring salespeople (and how to avoid it), this episode is loaded with straight-talk, strategy, and surprising truths.We talk:The ONE mistake that nearly sank Kevin’s early leadershipWhy “urgency, respect, and transparency” scale better than KPIsHow to use AI in sales without sounding like a botThe sales advice every technical founder needs to hear (ASAP)The books that rewired Kevin’s mindset for growth🎧 Whether you're a founder, a sales lead, or just obsessed with personal growth—this one's for you.📘 Free Sales Leadership Guides by Kevin Gaither:👉 Download Now🔗 Kevin on LinkedIn:👉 https://www.linkedin.com/in/kevingaither💼 Connect with Host Silvana Pimentel:👉 www.linkedin.com/in/silvana-pimentel1🔗 Connect with Kevin & Silvana

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Sales Secrets, Startup Wins & Leadership Fails — Kevin Gaither Gets Real

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This episode was published on March 28, 2025.

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In this Happiness by Habit episode, Silvana Pimentel dives deep with sales legend Kevin Gaither—a startup OG with 25+ years in the game, eight startups, and three successful exits.But this isn’t your average “sales tips” convo. Kevin pulls back the...

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