Episode 22: "50% of Corporate Payments are Still Paper Checks" | Payments Veteran Blair Jeffery on The Evolution of B2B Payments, Cross-Border Innovation, and Building Through Market Turbulence

The Diligent Observer Podcast

Today's episode explores three ideas that caught my attention:

* The persistence of paper checks reveals deeper truths about business incentives - It totally blew my mind that half of B2B payments are issued by check. Blair’s comments immediately brought to mind the classic Charlie Munger quote: “Show me the incentive and I’ll show you the outcome.”

* Regulatory shifts can derail even the best execution - Blair's story of how unexpectedly being forced into “regulated entity” status highlights how unexpected external forces can completely shove a company “off into a ditch,” regardless of how strong product-market fit might be.

* Risk-taking has different dimensions - I LOVED Blair’s interview questions about "what’s the biggest professional risk you’ve taken?” and “What’s the biggest disaster you’ve been a part of?” These are 100% going into my investing (and interviewing) toolbox.

I explore these ideas and more with Blair Jeffery, President & COO at ConnexPay.

Blair Jeffery brings 25 years of payments industry expertise as President & COO of ConnexPay, where he's pioneering virtual payment solutions for travel and B2B companies. His journey includes leading Noventis through its WEX acquisition and serving as CEO at Vertical, where he transformed construction payment processes. With executive roles at industry leaders like First Data and successful exits through Paymetric (WorldPay) and Textura (Oracle), Blair combines deep operational knowledge with financial acumen from his CFA background. Beyond his operational impact, he actively shapes the next generation of fintech entrepreneurs through his board role with the Aggie Angel Network, bringing both capital and industry wisdom to early-stage startups.

During our conversation, Blair shares:

* Why the seemingly simple goal of digitizing B2B payments remains elusive, including a discussion about float economics, relationship dynamics, and reconciliation challenges.

* A practical methodology for evaluating African fintech opportunities that focuses on team differentiation and product evolution potential beyond initial use cases.

* Insights into geographic expansion challenges demonstrated through ConnexPay's European market entry and the necessary pivots in operational approach.

What We Cover:

* 00:00 Introduction

* 03:10 Three Major Trends in Payments

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All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.