#30: How Gusto’s CEO Built a Category-Defining Company - Leadership, Scaling & Long-Term Growth

Dec 31, 2025

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Josh Reeves, co-founder and CEO of Gusto, shares how he built one of the most trusted platforms for small businesses, and what it truly takes to scale a company with purpose.

In this episode, Josh breaks down the realities of building and leading a high-growth startup, navigating regulation, designing products for long-term impact, and maintaining culture as teams and responsibilities scale. He explains how focusing on customers, discipline, and long-term thinking has shaped Gusto’s journey and why sustainable growth matters more than chasing short-term wins.

This conversation is a deep dive into founder mindset, leadership, and building enduring companies, essential listening for entrepreneurs, operators, and anyone serious about building something that lasts.

Follow Josh - X (Twitter): https://x.com/joshuareeves
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Timestamps:
01:44 – Why Most Startups Fail Before They Even Begin
02:27 – The Hidden Cost of Regulation
03:48 – Why Payroll and Benefits Matter More Than You Think
05:39 – The Real Reason Running a Business Feels So Hard
07:44 – The Benefit That Completely Changed Employee Loyalty
09:31 – What Sustainable Growth Actually Looks Like
11:34 – The Three Metrics That Truly Matter in Business
13:58 – Why Chasing Hypergrowth Can Destroy Great Companies
15:48 – Building a Company Meant to Last for Decades
17:20 – The Leadership Mindset That Separates Great Founders
18:54 – Why Being “Busy” Is Not the Same as Making Progress
20:21 – How to Identify People Who Will Actually Succeed
22:46 – How AI Is Changing the Way Teams Work
24:06 – Why Helping Others Is the Ultimate Advantage
25:32 – The Life Lessons That Shape Great Leaders
27:20 – Gratitude, Perspective, and Staying Grounded
29:33 – What Success Really Means (And What It Doesn’t)
31:43 – The One Principle That Guides Every Decision
33:22 – A Simple Philosophy for a Meaningful Life

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