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In this episode of The Exit, Steve McGarry sits down with Joshua Gould, CEO of thebigword, to discuss the grit and strategy required to scale a family business from $6 million in revenue to a $100 million powerhouse. Joshua’s journey is a masterclass in shifting from a “growth at all costs” entrepreneurial mindset to a sophisticated, private-equity-style operation that maximizes exit value.
Whether you are currently bootstrapping or eyeing an exit in the next few years, Joshua’s “real-world” insights provide a roadmap for building a business that buyers actually want to buy.
The 15-Year Journey: From Call Center to $100M Exit
Joshua didn’t start in the corner office. He began his career in the company’s call center, skipping college to avoid debt and learning the business from the ground up. After moving to New York at age 19 to establish the U.S. branch, he spent the next 15 years (2006–2021) bootstrapping the company’s growth.
During the early stages, the philosophy was simple: grow at all costs. Joshua admits that in the early days, they were so focused on winning contracts from giants like Google and various governments that they didn’t always know if the deals were profitable, they just wanted market share.
“It was a game of inches every single year… Every penny went back into hiring people.”
Thinking in Multiples: The PE Mindset
A turning point for the business came around 2017 when Joshua began viewing the company not just as a job, but as an asset. He highlights several shifts every founder should make to prepare for an eventual sale:
- Hire a “Real” CFO: Once a company passes $5 million in revenue, you need more than a financial controller. You need a CFO who can manage costs, build a “data room,” and understand the levers of valuation.
- The “Multiple” Filter: Joshua advises looking at every expense through the lens of your exit multiple. If you think your business will sell for 20x cash flow, a $7,000 business class flight effectively “costs” you $140,000 in exit value.
- Normalize Your EBITDA: Most owners leave money on the table by failing to track “ad-backs”, one-time costs (like lawsuits or office renovations) that shouldn’t count against your ongoing profitability.
Timing the Exit: Sell When You Don’t “Need” To
One of Joshua’s strongest pieces of advice is to sell your business when it is on the way up, not after it has peaked. Buyers are astute; they can sense when an owner is selling due to burnout, divorce, or medical necessity, which hurts the valuation.
To get the best price, potentially double or triple the average, Joshua suggests showing three consistent years of growing revenue, gross margin, and profitability.
Avoiding “Single Point of Failure” Mistakes
Joshua candidly shared mistakes he’s seen (and made), including:
- Being the “Face” of Every Client: If the business cannot run successfully without the founder for 90 days, it isn’t truly sellable.
- Carrying “Dead Weight”: Whether it’s an unprofitable client or a mediocre staff member kept out of loyalty, “weight” slows down your growth and harms your outcome.
- Ignoring Taxes: Joshua noted that failing to plan for taxes ahead of time cost him millions of dollars post-exit. He recommends hiring a top-tier tax accountant long before the deal closes.
What’s Next for Joshua Gould?
After selling 75% of thebigword in 2021 to Susquehanna Growth Equity, Joshua remained as CEO and became an active investor. Today, he is focused on:
- The ExecCraft Podcast: Providing “no-BS” advice for executives on YouTube.
- Audley Capital: Investing in and scaling single-doctor medical offices into multi-doctor practices.
- AI Innovation: Building AI tools through thebigword to eradicate communication barriers globally.
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