Crossfin: The Quiet Force Behind African Fintech | Dean Sparrow & Anton Gaylard

Most people have never heard of Crossfin. But you have heard of what they built. iKhokha sold to Nedbank for R1.65 billion. Adumo sold to Lesaka for R1.6 billion. Dean Sparrow and Anton Gaylard join Colin Iles to unpack how two operators from a small-cap JSE-listed retail IT business became the most consistent fintech investors on the continent. They go deep on backing founders through fraud investigations and near-collapse, why they refuse to fund above-the-line marketing, how they actually price an early-stage deal, and why they would take patient capital over a five-year private equity clock every single time. Recorded live on 16 July 2026 as part of the AWS Founders Series, in partnership with Silicon Overdrive and Amazon Web Services. Chapters 00:00 Introduction 01:44 The portfolio, the exits and the co-investors 03:34 Two operators who never planned to be investors 04:05 Meeting at UCS Group and the move into payments 06:26 Delisting UCS and the birth of Capital I 08:40 Doubling down on fintech: Crossfin launches in 2017 08:53 Backing the jockey: why they stayed with Bevan 11:51 iKhokha: what they saw in an idea-stage team 14:43 Beaten to market by two banks, and why they carried on 16:16 The R60m to R70m hole that nearly broke wiGroup 18:44 Holding the trust of founders and investors through a crisis 20:56 Good news travels fast, bad news travels faster 23:24 Respecting the experts: Retail Capital through COVID 25:14 Why Retail Capital was worth the risk 28:06 What founders get wrong when they come asking for money 31:00 Chasing the valuation instead of building the business 34:31 Money is the easy part: why the right investor matters 35:56 When should a fintech founder raise? (audience question) 38:14 How do you value an early-stage business? (audience question) 42:33 Structuring the iKhokha deal 43:50 Where the science stops and the horse trading starts 45:15 Do advisors on your board actually earn their equity? 47:20 The most underserved payment problem of the next five years 49:15 Where Crossfin is investing now: Mercury, PATS and MyPinPad 52:00 Single founder or founding team? 52:43 Are exits on the continent really limited? 54:01 Exit timing and the case for patient capital 56:44 Closing thoughts and what is coming next More at https://colinilesmedia.com Thanks to our partners Amazon Web Services and Silicon Overdrive (https://www.overdrive.co.za/aws/) #Fintech #Payments #VentureCapital #PrivateEquity #SouthAfrica #Startups #AWS #Crossfin #iKhokha #Adumo