Fintech Takes x SOLO Presents Source of Truth Episode 3: Hard Lessons Learned from the Trenches

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Sep 11, 2025

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Join Luke Voiles, CEO of Pipe, Rob Frohwein, co-founder of Kabbage, Jill Sheckman, former Global Chief Credit Risk Officer at PayPal, and Brian Hamilton, president of Coastal, as they share gripping tales from the frontlines of fintech. They discuss the critical importance of accurate data in lending, the challenges of scaling businesses in a regulated environment, and the ongoing struggles with adverse selection and trust in data. Their hard-won lessons offer valuable insights into the future of lending and the vital need for innovation in financial services.

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INSIGHT

Data Quality Is The Core Constraint

Data quality and completeness are the core constraint in small business lending.
You need transaction-level, accurate money-in/money-out data to underwrite reliably.

ANECDOTE

QuickBooks Entries Didn’t Mean Invoices Were Sent

QuickBooks ledger entries looked like invoices but were often manually entered and inaccurate.
That mismatch forced a move from invoice factoring to DSCR underwriting.

INSIGHT

First-Party Data Reduces Friction But Lacks Breadth

Proprietary first-party transaction data can let you avoid bureau checks and reduce friction.
But that data usually covers only part of a business's revenue, limiting product scope.

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Hello, and welcome back to Source of Truth, a new miniseries sponsored by our friends at SOLO. This series is about information asymmetry; the enemy of financial services.

Until now, we’ve focused on theory: the broken data infrastructure we’ve inherited.

In Episode 3, we move from theory to reality. I ask four veteran founders and operators:

What are the most difficult challenges you face when building and scaling up a consumer or small business lending business?

What hard lessons can be learned from overcoming or in some cases failing to overcome those challenges?

And what do those hard lessons tell us about the future of lending and data infrastructure in the U.S.?

These conversations are short but illuminating: expect war stories from the early days of well-known fintechs, insights and creative ideas for scaling up in our heavily regulated industry, and candid admissions about the problems they still haven’t cracked (and why).

Guests (in order of appearance):

Luke Voiles: CEO of Pipe; longtime SMB lending operator & executive

Rob Frohwein: Co-founder and former CEO of Kabbage

Jill Sheckman: former Global Chief Credit Risk Officer at PayPal; longtime credit risk executive at AmEx

Brian Hamilton: Co-founder and former CEO of ONE; President at Coastal

Episode 3 is your field guide to the real constraints operators face — and the data standards and product choices that actually moved loss curves, conversion, and access.

Don’t forget to subscribe and catch more insights in upcoming episodes of Source of Truth!

This miniseries is brought to you by SOLO.

SOLO resolves and connects customer data across silos — so teams stop rekeying the same customer info for the hundredth time and finally move forward.

Break the cycle at SOLO.one - That’s SOLO dot o-n-e.

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