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
04:50 Why Businesses Still Love Paper Checks
08:00 Inside the Banking Ecosystem
13:10 Finding Your Way Into Payments
19:30 The African FinTech Revolution
24:00 When Regulation Changes Everything
29:30 The Investor Who Wanted Out
36:00 The Problem With Early Institutional Money
41:10 How ConnexPay Bridges Payment Gaps
43:40 Going Global: The European Expansion
Listen now on Spotify, Apple Podcasts, and YouTube.
Connect with Blair
Connect with Andrew
Newsletter: https://thediligentobserver.substack.com
Website: https://pitchfact.com/
Stuff We Reference
Bitcoin: https://bitcoin.org/en/
Jerry Seinfeld: https://jerryseinfeld.com/
Bill.com: https://www.bill.com/
HighRadius: https://www.highradius.com/
Ramp: https://ramp.com/
Divvy (acquired by BILL): https://www.bill.com/
Brex: https://www.brex.com/
Intuit QuickBooks: https://quickbooks.intuit.com/
ConnexPay: https://connexpay.com/
FTV Capital: https://ftvcapital.com/
VKTRY Insoles: https://vktry.com/
Houston Angel Network: https://www.houstonangelnetwork.org/
Aggie Angel Network: https://mcferrinrevventures.com/aggie-angel-network/
Know someone who would enjoy this episode? Share it with them!
All opinions expressed are personal and may not reflect the views of the individual’s organization or of The Diligent Observer. Not investment advice.
Share this post