Many Bootstrappers Find It Hard to Change Their Frugal Habits

by | Nov 30, 2025

Bootstrappers are seriously frugal when they get going, since they are investing their own time and money.

If their business grows and profits increase, it’s often hard to break the habit of being so frugal all the time.

Most founders stay very practical even after selling their companies, but they deliberately find areas to spend more when they have extra money.

Raju Patel founded eShow Event Management Solutions over 25 years ago after building a speaker portal for a magazine company and realizing he had a repeatable software product.

What began as a one-man shop in suburban Chicago evolved into a robust event-management platform serving associations that needed complex, multi-module functionality.

His business grew steadily as he delivered registration, booth management, speaker portals, and onsite systems for demanding event teams.

Today, eShow has 125 employees, more than 14 integrated modules, and supports hundreds of events each year for 300+ customers, including large association conferences with tens of thousands of attendees.

The company has always been profitable, self-funded, and built through careful reinvestment, steady hiring, and deep product expansion.

Raju rebuilt the platform multiple times, including a shift to a modern stack.

Still independent with over $10 million in revenues, Raju is now building a VP-level leadership team, exploring practical growth capital, and planning a hybrid event model that blends in-person and virtual experiences.

Raju invested in the business and stayed frugal for many years, avoiding big bets that might not pay off.

But after COVID and even more growth, Raju is thinking differently, as he describes:

“Looking back after 20 years running this as a small business in software, think I would have figured out how to pull a little bit more money out. It would have given me a better peace of mind.

“I wouldn’t have even known how to spend if I pulled a million out back then, it would have been wasted. I was very frugal and invested in my business every year.

“But now I could figure out how to spend a million dollars, on savings and other personal spending that would be meaningful. It would be liberating. I deserve it, so I’m going to spend a little bit more, not be frugal. I can be frugal in my business and in my personal life, but not be so frugal!”

His business is worth a small fortune on paper, but he’s not trying to sell it.

Old habits of frugality can be hard to break.

Check out this practical interview with Raju Patel on the Practical Founders Podcast.

Greg Head posted this on LinkedIn on November 30, 2025.

Check out the comments and join the discussion on LinkedIn.

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