Building to Sell: Scaling, Sacrifice, and Smart Exits with Joshua Gould

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: -- In this episode of The Exit, we sit down with Joshua Gould, CEO of thebigword, who shares his journey from joining a small family business to scaling it into a $100 million company and ultimately selling a majority stake. Joshua breaks down the realities of bootstrapped growth, the sacrifices required to reinvest every dollar back into the business, and the turning point where he shifted from chasing revenue at all costs to building a company that could actually be sold. We dive into what it really means to “run your business like a private equity firm,” including why most founders leave millions on the table by not preparing early enough, how to think about every expense as a multiple of your eventual exit value, and the critical importance of having the right financial leadership in place. Joshua also shares hard-earned lessons on timing your exit, avoiding common deal mistakes, and why selling when you don’t have to is often the smartest move. Whether you are scaling toward your first exit or optimizing for long term value, this episode is packed with practical insights on building a business that buyers actually want. -- Joshua Gould is a seasoned executive with over two decades of C-level leadership experience across the technology, defense, consumer packaged goods, and healthcare sectors. Currently as the CEO of thebigword, he has built a reputation for driving strategic growth, operational excellence, and innovation within complex organizations. Known for his ability to scale businesses and lead cross-functional teams, Gould brings a global perspective to leadership, combining commercial insight with a strong focus on delivering measurable results. LinkedIn - The Exec Craft Podcast - -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

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Building to Sell: Scaling, Sacrifice, and Smart Exits with Joshua Gould is an episode from The Exit - Presented By Flippa by The Exit - Presented By Flippa.

This episode is 00:34:29 long.

This episode was published on Apr 6, 2026.

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