The Breakout CEO

About The Breakout CEO

The Breakout CEO is a CEO podcast for scaling CEOs and founders, hosted by Jeff Holman. In each episode, a growth-stage CEO shares the real decisions behind scaling a business, from hiring and leadership to pivots and revenue growth. These founder interviews focus on companies in the $5M to $50M range and the business growth strategies that moved them from startup to scale-up. Every conversation centers on an inflection point: the moment a company outgrew its old way of working and the CEO had to choose a new one. Guests explain what they decided and what they would do differently. Recent topics include panic hiring, AI adoption, hidden revenue leaks, and building trust before building demand. Jeff Holman is the founder of Intellectual Strategies, where he works as outside general counsel to scaling CEOs and founders on strategy, governance, and risk during rapid growth. He brings that operator-level view to each interview. Be a guest: We feature a limited number of CEOs and founders with first-hand breakout stories. Apply at https://go.intellectualstrategies.com/ Media and event partnerships: For press access, on-site recording, or event collaboration, contact us through intellectualstrategies.com/podcast.

Publisher

Jeff Holman, General Counsel for Scaling CEOs and Founders

Category

business · business · business

Language

en

Explicit

No

First episode

20 Aug 2025

Latest episode

29 Oct 2026

Latest episodes

106 episodes in the feed.

1. 

   29 Oct 2026

   106 - Hand Off Technology and Your Growth Stalls

   What do you do as a CEO when the supplier behind most of your inventory disappears overnight? Rupesh Sanghavi, founder of Ergode, faced exactly that when half.com shut down and took 80 to 90 percent of his inventory source with it. In this episode of The Breakout CEO, he walks through how each disruption, from a lost supplier to a ceiling on C2C margins, the COVID acquisition window, and tariff uncertainty, pushed his ecommerce company into its next business model. Rupesh started by buying a textbook on eBay and pre-selling it on Amazon, then wrote software to automate the buying while still working as an application engineer. He explains why he launched a second business to work directly with brands, how moving to brand ownership pushed margins past double digits, and the acquisition criteria that led him to walk away from deals that looked great on paper while others were reportedly paying 9 to 12 times EBITDA. He also gets candid about the two decisions he believes held the company’s growth back: closing his mind to outside investors, and the years he let someone else run technology, which he calls the least growth years. For founders weighing growth capital, team building, or how closely to stay involved in technology in the age of AI, this conversation shows what those choices can cost. Rupesh Sanghavi is the founder of Ergode, ergode.com. 00:00 Lessons From Scaling E-Commerce 01:59 From Engineering to Entrepreneurship 05:17 The $1,600 Textbook Sale 08:05 Building a Side Business 12:21 Creating a Brand Ecosystem 16:38 Losing Most Inventory Overnight 18:58 Acquiring Brands During COVID 22:41 Prioritizing Team and Technology 25:09 Becoming a Servant Leader 27:02 Choosing Will Over Skill 34:14 Evaluating Brand Acquisitions 47:51 Lessons That Limited Growth

2. 

   22 Oct 2026

   105 - The $2M Never Came. The CEO Fired Everyone

   Asaf Darash, CEO of Regpack, shares how he navigated a failed $2M investment by cutting his team and bootstrapping to achieve company survival and founder ownership.

3. 

   16 Oct 2026

   104 - The Real Reason Scaling CEOs Keep Panic Hiring

   Host [Host Name] interviews Darren Tompkins, founder of Vader-Rey Companies, about why CEOs panic hire and how to strategically delegate for sustainable growth.

Who has been a guest on The Breakout CEO

Names identified in recent episode analyses. Showing up to five guests.

• Asaf Darash
• Darren Tompkins
• Stacey Hylen
• Kevin Perlmutter
• Bryant Oberg

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

5 ratings

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Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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