Swift Expo Cofounder, Serial Entrepreneur is No Joke

Bob Gillespie treats startups as no laughing matter.  He’s an expert, too, as both a former stand-up comedian and a current serial entrepreneur with two successful exits already under his belt.

Bob and his cofounder, Matt Dabney, intend to disrupt the world of trade show and conference management with Swift Expo, a company offering a cloud-based SaaS solution that streamlines staff scheduling.  The idea is simple: most trade show organizers use less than advanced methods for scheduling the armies of workers who build, operate, and tear down large gatherings.  Swift Expo’s product makes scheduling much easier and more effective, and as a result, shows run smoothly.

Most importantly, the beta has proved that the product works.  In a recent test, Swift Expo’s software reduced a conference organizer’s time spent scheduling from 120 hours down to 8.  Better scheduling also improved staff morale, taking the no-show rate down from 25 percent to 8 percent.  In addition to scheduling, Swift Expo has plans for future offerings, which will make it even stickier among its customer base.

In addition to his own entrepreneurial success, Bob is a student of the startup world and has parlayed his learning into teaching other starters.  Bob regularly teaches (including at Chicago’s 1871 co-working space where Swift Expo is officed) about structures for raising capital and modeling financial data in a coherent way.

Bob also shares his criteria for evaluating his own involvement in a startup.  This determination is especially important for serial entrepreneurs like Bob who are in high demand, given their successful track records.  This litmus test includes the following:

  1. Internet/Cloud—Does the business deliver its product or service via the Internet/cloud, and is it easily scalable?
  2. B2B—Does the business sell to other businesses?
  3. Big and Defined Market—Is the market large, and does it have well-defined customers?
  4. Entrenched Competition—Is the market devoid of settled competition?
  5. Payoff—Do clear exit options exist from the start?

Swift Expo passed all of these tests with flying colors, making Bob’s decision to join with Matt an easy one.

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Written by:
Clint Costa is an attorney and CPA with the Chicago law firm of Harrison & Held, LLP, working with startups, entrepreneurs, and privately held companies on all manner of official-sounding legal and tax matters. Reach Clint at ccosta@harrisonheld.com or (312) 803-7104.
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