How I Invest with David Weisburd
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Why couldn't banks serve the lower middle market with flexibility in the early 2000s?

Banks were locked into rigid processes by regulatory requirements and could not customize deals for smaller companies. Only GE Capital and Heller Financial operated outside these constraints, leaving the lower middle market entirely unserved—a gap David Weisburd identified and filled by founding Monaro Capital in 2001.

Banks regulated, non-banks unconstrained

During his 14 years as a lawyer specializing in M&A and bank financing for private equity transactions, David Weisburd saw the limitation firsthand. Banks had no choice but to follow strict regulatory rules, which meant they could not bend their structures to fit unique deal requirements. They had one way to do things, and borrowers had to fit into that mold.

At the same time, a handful of non-bank lenders—GE Capital and Heller Financial—were operating in a completely different mode. Unregulated, they could structure deals creatively, customize terms for their clients, and take on deals with more flexibility. The catch: they focused exclusively on larger transactions. No one was building a non-bank platform for the thousands of smaller, mid-market companies across Main Street America.

This disconnect was the spark. As Weisburd explains in the episode, he realized he could apply everything he had learned about transaction finance while working with banks and private equity—but deliver it in a user-friendly, non-bank format designed for smaller companies who had been shut out of institutional credit markets.

Building Monaro from first principles

In 2001, Weisburd left his legal practice and founded Monaro Capital with three experienced bankers: a credit specialist, an origination expert, and an underwriter. Each was earning $100,000 annually with families to support, so convincing them to join a startup required absolute conviction. He promised them they were entering a new asset class—one that would reshape how transaction finance worked in America.

The market conditions aligned perfectly. The lower middle market—200,000 companies in the U.S. representing 50% of workforce employment and one-third of GDP—had no efficient way to access non-bank credit. There was no competitor model to copy, only a clear need and a regulatory moat that protected Monaro from entrenched banking players.

Today, that bet has paid off at scale. Monaro Capital now manages $24 billion in assets and deploys roughly $10 billion annually. More broadly, as discussed in this podcast, the private credit market has grown to $2 trillion and is projected to reach $5 trillion within five years—a complete inversion of the early 2000s, when 90% of transaction financing flowed through banks and only a handful of non-banks existed.

David Weisburd — Founder and CEO, Monaro Capital. After 14 years practicing law in M&A and bank financing for private equity transactions, Weisburd identified a structural gap in credit markets: banks lacked the flexibility to serve smaller deals, and no non-bank competitors had yet entered the lower middle market. He founded Monaro Capital in 2001 to fill this void with creative, customized transaction finance for Main Street companies, building it into a $24 billion asset manager deploying $10 billion annually.

To understand how this market has evolved further and what the future of private credit looks like, listen to the full conversation on Listenly.

See also

What common cognitive bias limits venture investors' deal sourcing and reduces returns?

Venture investors have historically relied on their networks to surface opportunities, creating a bias where they miss high-quality outsiders.

How do multi-stage venture firms expand beyond their core competency, and what is the historical precedent?

Private equity firms like KKR and Blackstone emerged with one core business and over time expanded into adjacent asset management.

What structural challenges prevent institutional LPs from participating in co-investment opportunities?

Most institutional LPs are not equipped for rapid decision-making. Co-investment opportunities often require decisions within less than five days.

Key takeaways

Listen to the episode on Listenly