Scale, Raise, or Exit: The Lifecycle of a SaaS Business with James Benham

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About Our Guest

As the co-founder and CEO of JBKnowledge, James Benham and his team have led the development of technology for some of the largest insurance carriers, brokers and TPAs in the world, helping them build award-winning insurance ecosystems.

James is also the co-founder and CEO of two disruptive InsureTech companies: SmartCompliance—a top insurance certificate tracking and compliance management software; and TerraClaim—a cloud-based claims management software that improves claim outcomes for providers and consumers of Property and Casualty (P&C) insurance.

James started his journey as a tech entrepreneur in his Texas A&M dorm room in 2001 and has harnessed his passion for innovation to bootstrap multiple businesses to financial sustainability. James’ most successful bootstrapped exit occurred in 2018 when he and his team sold their construction bid management software, SmartBid, in a groundbreaking deal with ConstructConnect.

James is a sought after consultant and speaker at the forefront of innovation in the insurance industry. His no-nonsense style and love for “geeking out” on technology has landed him keynote opportunities on over 400 conference stages in the last 15 years. James is also the host of the growing 70+ episode show, The InsureTech Geek Podcast, where he interviews leading industry experts, including the Chairman & Co-Founder of InsureTech Connect, Caribou Honig, and AXA XL executive, Rose Hall.

When James isn’t working hard on improving companies—his own or his clients’—he keeps himself busy as a Regent at Texas Southern University or with his many hobbies as a pilot, musician, Star Trek fan, tech gadget aficionado, and Lean Methodology “life hacker”.

About this Episode

Scale, Raise, or Exit: The Lifecycle of a SaaS Business with James Benham

The basic rule of bootstrapping is build what you have to so you can later build what you want to.

This concept carried entrepreneur James Benham from his first software business to the next, and the next, and the next. He used all the profits from his service business to fuel the growth of SmartBid, a construction software.

Twelve years of extreme capital efficiency later, SmartBid had 1,143 customers, 250,000 companies bidding, 10,000 projects, and 3 million downloads a week across several dozen time zones.

It was then that James reached his inflection point: Scale, raise, or exit. He chose to exit and the deal was groundbreaking.

What you will learn in this episode

In this episode we’ll cover everything from:

  • Tips on how to increase product adoption for a SaaS company
  • How to monetise your screen real estate without plaguing users with ads
  • What it means to bootstrap and how to do it well
  • Taking calculated risks during the startup phase

Connect with James Benham

Show Notes

(3:33) James came from a long line of entrepreneurs, and after years of side hustles in college, approached his dad saying he “didn’t like this working for other people thing” and was ready to start a business. His dad lent him $5K and he started JBKnowledge on a hope and a dream.

(11:30) The biggest problem plaguing SaaS is underutilisation. Here are James’ recommendations for increasing not just market fit, but the more important metric of adoption.

(18:21) Bootstrapping is how James builds the bulk of his businesses. While there are definitive pros to outside capital, James makes a strong case to bootstrap.

(28:38) One of James’ general rules is to ensure no one thing generates more revenue than his profit margin. This diversification is a safeguard in bootstrapping.

(41:42) James was firmly convinced he would never sell, but after joining Entrepreneurs Organization, he realised there was a time for everything. And so when James reached his inflection point, he was able to recognise this and ended up exiting to a competitor in a groundbreaking deal.

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