At some point in your lending career, you will be tempted to grow just because you can. An unexpected deal lands in your lap, capital is available, and the logic seems airtight. More loans mean more revenue. But before you hire another underwriter or raise another round, consider the framework that Abbas Jessa, founder of Wentwood Capital, has built his entire business around. It challenges almost every conventional instinct about what a successful lending operation should look like.

Wentwood is an investment firm with a lending component.

That’s because everything the company does is engineered around lessons Jessa learned while managing over $500 million in defaulted paper across more than 3,000 loans. He saw “volume chasing” lead to businesses serving their own infrastructure and experiencing decreasing returns despite more loan count, more capital, and impressively structured operations. Each element fed the volume machine, but in the end, volume didn’t keep the ship afloat.

Rightsize Your Business Model

Jessa lost all appetite for that structure and redefined the business model into something sustainable for him. Framing his business as an investment firm that happens to earn returns through lending establishes the right constraints from the start.

Many business models genuinely benefit from larger volume when execution discipline remains intact, leading to improved pricing power, diversification, and operational leverage. Jessa’s model will not be right for everyone. The takeaway is to find, or create, the model that will fundamentally work for your goals.

To rightsize your model, ask questions about the following areas:

Now and later. What type of day-to-day business do you want to operate now? How about five years from now?

Your definition of success. Are you building for maximum volume, maximum margins, lifestyle flexibility, long-term durability, or something else?

Your role as a leader. Does your current growth strategy support your preferred role as a leader?

Your motivation for growth. Are you expanding because the economics justify it, or because the industry rewards visible scale?

Your energy. What parts of the business feel energizing versus operationally draining?

Goal achievement. Can I achieve “enough” with this business model to reach my business and personal goals?

Rightsize Your Products

Wentwood focuses on second liens, cross-collateralized structures, lower-credit-score borrowers, and loans with legal or asset management complexity. It targets 60-65% LTV in nonjudicial markets.

By concentrating on products that require additional judgment, Wentwood earns a premium and has less market competition. The trade-off is that complexity does not scale easily. Jessa cannot hire his way to expertise in second liens, so his staff are trained internally, and onboarding is much slower. Loans also require a more hands-on approach and limited (if any) automated judgment. The willing investor pool is smaller, and there are few securitization opportunities.

This still works for the company because that complexity and risk is priced accordingly, and the product line fits the goals of the business model.

To rightsize your products, consider where your team’s expertise and judgment are genuinely strong, and where your firm possess a competitive advantage others avoid. Be honest about how much operational complexity your infrastructure can realistically absorb, and whether additional scale would improve or dilute underwriting quality. Finally ensure your products align with your capital structure.

Rightsize Your Capital

Wentwood keeps its capital base long-term and closed, which means Jessa feels less deployment pressure and can focus on judgment calls between “good” deals and “great” ones, growing the book organically by reinvesting proceeds.

This capital strategy matches both the company’s business model and its product line. By avoiding additional leverage or equity partners with preferred returns, Jessa stays focused on finding the best deals for a closed group of investors. There are certainly liquidity constraints and growth ceilings, but he views those as acceptable trade-offs.

To rightsize your capital, consider whether your funding sources align with your investment horizon and risk tolerance, and whether additional capital would genuinely improve outcomes or simply increase expectations. Be clear about how much deployment pressure you are comfortable with and whether your current structure gives you the flexibility you need to pass on marginal deals.

Rightsize Your Operational Structure

One of the defining features of Wentwood’s business is how closely its origination, underwriting, servicing, and asset management functions are connected. That integration ensures the people originating loans understand what happens when those loans perform as expected—or when they don’t.

By refusing to separate these functions, Jessa ensures his origination team never gets too volume-hungry at the expense of the service team inheriting the consequences, or that underwriters get too picky and starve loan officers of solid deals. This low-silo environment serves as a structural guardrail to ensure everyone keeps the firm’s return a top priority.

To rightsize your operational structure, consider whether your teams are incentivized toward the same business outcome; where silos may be creating friction, misalignment, or unnecessary risk; and the checks and balances that must be added for safe growth.

Rightsize Your Infrastructure

Jessa makes an intentional decision to wait until a genuine bottleneck appears in his business before acting. This requires a willingness to feel real operational discomfort. Through trial and error, Jessa has discovered that many infrastructure issues remain hidden and the business gets bigger without getting better if he hires the moment things get slightly uncomfortable.

Going into any infrastructure decision, Jessa has a clearly defined threshold: He is willing to scale process, data management, and administrative coordination but not credit judgment or relationship management. And any optimization must optimize for net results.

That means tax planning matters as much as origination volume, and servicing efficiency is as important as deal flow. In most cases, infrastructure upgrades look like use of offshore professionals, structured processes, and AI-enabled workflows. Only when those won’t solve the issue will he look at a permanent hire.

To rightsize your infrastructure, distinguish between bottlenecks that are temporary versus structural. Before adding headcount, ask whether process improvements could eliminate the need entirely, and which functions genuinely require human judgment versus those that don’t. Finally, consider not just whether an infrastructure will increase profitability, but by how much—and whether that change will scale fixed costs faster than it delivers operational efficiency.

The Unconventional Conclusion

One final big-picture question will help ensure you’ve set the right parameters for your business: What is my risk tolerance for change or transition in uncertain markets?

A higher risk tolerance naturally creates more flexibility across these trade-offs. You’re more comfortable with needing to make big operational and model changes based on changes in your environment and likely have a greater willingness to fight through potential instability. These are lenders geared toward a fast-paced, volume-centric model.

If stability is the name of the game, slow growth and careful scale are likely to be your North Star. And to be clear, “rightsized” doesn’t necessarily mean small; it means strategically aligned.

By staying selective, keeping costs lean, integrating functions tightly, and measuring everything against net results, Jessa has built a business that performs, endures, and one he’s passionate about leading even as it grows.

The private lending industry rarely awards discipline with much more than a whisper, but it will punish overextension at earsplitting volume. Finding the “right size” growth goal for your business ensures that all elements are aligned with where you really want to be.