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

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Divot

Derek Andersen

32 episodes

5 days ago

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

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

Divot

35 minutes 38 seconds

1 week ago

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

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
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

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

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#DivotPodcast #Leadership #Entrepreneurship #BuildingInPublic #SmallBusiness #FounderJourney #PurposeDriven #LongTermThinking #StartupLife #Grit #MeaningfulWork