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The Chip Mahan Interview: CEO of Live Oak Bank | Ep. 190

Release Date: 10/30/2025

Final Episode: Revisiting My Roots (MCC Reunion) | Ep. 191

The Art of SBA Lending

This week marks the finale of The Art of SBA Lending podcast, and Ray Drew brings it home by reuniting with his original mentors and colleagues from the era that shaped his career: the Mercantile Capital team. Listen as they reminisce about the "good old days" of 2011–2013, an era defined by reinventing business after the 2008 crash. The panel discusses how Mercantile Capital was built around the niche business of 504 interim lending (an industry they essentially invented). They recall the unique office culture, characterized by healthy competition, daily in-person mentoring sessions,...

The Chip Mahan Interview: CEO of Live Oak Bank | Ep. 190

The Art of SBA Lending

This week on The Art of SBA Lending, we sit down with Live Oak Bank CEO and founder, Chip Mahan, to discuss the revolutionary ideas that transformed the SBA landscape. Chip Mahan, who started the bank in 2008, disrupted the existing SBA playbook by focusing on nationwide industry vertical lending. Chip details the bank's founding during the 2008 financial crisis , when he was told by the FDIC to liquidate the bank. He reveals the unique philosophy that led to the bank becoming a top SBA lender, including: rejecting the traditional commission-based compensation model to properly align interests...

Winding Down a Shop while Battling a Major Health Crisis feat. Heidi Whitesell | Ep. 189

The Art of SBA Lending

This week on The Art of SBA Lending, we go behind the scenes with Heidi Whitesell to unpack the leadership, culture, challenges, and ultimate wind-down of a successful SBA lending division. Ray Drew sits down with Heidi, who he calls one of the best leaders he's ever worked for, to discuss the philosophy that created a legendary, family-like culture in a fully virtual, non-bank setting. Heidi shares the vision for her former venture, Fund-Ex, which quickly climbed the national rankings without losing its unique team culture. She reveals her leadership principles, including the powerful belief...

USDA Lending: The Last Frontier? feat. Jason Hoerr, Steve Small, & Charles Conoley| Ep. 188

The Art of SBA Lending

This week on The Art of SBA Lending, we explore the world of USDA Business & Industry (B&I) lending, often considered the "last frontier" of government-guaranteed small business finance. Host Ray Drew, who admits to knowing very little about the program, is joined by a panel of USDA experts—Steve Small, Jason Hoerr, and Charles Conoley—to demystify this often misunderstood loan program. The panel provides a deep dive into the B&I program, which is designed to stimulate economic activity and job creation in rural areas (populations of 50,000 or less). They reveal key advantages...

Money Store Reunion feat. Joe Weiner, John Handmaker, Sam Renta, & Vince Calicchia | Ep. 187

The Art of SBA Lending

This week on The Art of SBA Lending, we're doing something special: a Money Store reunion episode. The Money Store pioneered the Business Development Officer (BDO) model and revolutionized the SBA lending industry, holding the top position for 16 consecutive years. Host Ray Drew brings together four Money Store alumni-John Handmaker, Vince Calicchia, Joe Weiner, and Sam Renta-to share stories and insights from the company that changed SBA lending forever. The panel reminisces about the legendary BDO boot camps, the company's aggressive marketing, and its commitment to a sales-driven culture....

The Loan Broker Panel | Ep. 186

The Art of SBA Lending

This week on The Art of SBA Lending, we're getting a unique look at the state of the SBA marketplace from the perspective of the loan broker. Host Ray Drew brings together a panel of top-producing SBA loan brokers whose combined volume would rank them among the top 1 or 2% of all SBA shops. Joining the conversation are Matthias Smith from Pioneer Capital Advisory, Jerry Freedman from Freedom Business Financing, and Zach Renta from SBA Loan HQ. The panel discusses why the traditional BDO model is becoming outdated as brokers build sophisticated operations and gain direct access to information...

The Untold Story of Lendistry's Rise in 7(a) Lending feat. Everett Sands | Ep. 185

The Art of SBA Lending

This week on The Art of SBA Lending, we sit down with Everett Sands, a leader who successfully propelled Lendistry into the top tier of the nation's SBA 7(a) lenders. Everett explains his approach to SBA lending, which involves applying lessons learned from other industries like residential and auto lending to an industry he feels is decades behind. As a fintech and a CDFI, Lendistry occupies a unique space in the market. Everett discusses how his company is leveraging technology and a mission-driven approach to win customers by offering a better, more user-friendly experience than...

Casca Has Arrived (and Will Drastically Change How We Make SBA Loans) feat. Lukas Haffer | Ep. 184

The Art of SBA Lending

This week on The Art of SBA Lending, we're joined by Lukas Haffer, co-founder of Casca, to discuss how AI is set to revolutionize small business lending. With a unique background that includes building software for major European banks and earning Standform MBA, Lukas brings a fresh, outside-the-box perspective to our industry. He shares how his company is taking on the "disaster" of small business financing by arming SBA lenders with cutting-edge technology to fight back against predatory online lenders. We dive deep into how new technology can solve the industry's biggest pain points,...

Quitting the Bank: Closing 100 Deals in 24 Months feat Heather Endresen | Ep. 183

The Art of SBA Lending

This week on The Art of SBA Lending, we're joined by Heather Endersen, a true veteran of the SBA world with a career spanning decades. Having managed SBA departments and pioneered business acquisition lending, Heather shares her journey and explains why she made the leap from a top-producing BDO at a bank to launching her own brokerage. Heather gets candid about the shift in the SBA landscape, from the rise of business acquisition loans to the changing dynamics between lenders and borrowers. She also pulls back the curtain on the brokerage model, explaining why it's a more efficient way to get...

Lending with Heart: Sharing 30 Years of Lessons Learned feat. Diane Heyden | Ep. 182

The Art of SBA Lending

This week on The Art of SBA Lending, I’m sitting down with Diane Heyden to get her take on leadership, career shifts, and the evolving landscape of small business lending. Diane, a seasoned veteran who has worked as a BDO, sales manager, and division manager, shares her unique perspective on what it takes to succeed in an industry where no two people are alike. From a memorable but short-lived move to a bank in Iowa to taking on a new role with a beloved team on the West Coast, Diane unpacks the lessons learned from her own career journey. We also dive into the state of the industry,...

More Episodes

Chip details the bank's founding during the 2008 financial crisis , when he was told by the FDIC to liquidate the bank. He reveals the unique philosophy that led to the bank becoming a top SBA lender, including: rejecting the traditional commission-based compensation model to properly align interests , developing a "theory of verticality" by targeting specialized industries like veterinarians and chicken farmers , and using data from the Freedom of Information Act to determine which industries pay back their loans. He argues that a floating rate 7(a) loan is the "best asset that anybody can put on any bank's books.”

The episode also covers the bank's commitment to technology, the importance of perfecting the "handoff" between the lender, underwriter, closer, and servicer , and the future of banking in the age of Artificial Intelligence. Chip explains how AI will dramatically affect determining SBA loan eligibility and create an "automatic credit memo".

🎯 In this episode:

Founding Under Fire: The story of getting a bank charter in May 2008 and being told to liquidate the bank in March 2009 by the head of the FDIC in Atlanta.
The Verticality Edge: Why Live Oak focused on niche industries and hired domain experts to create an "unbeatable" credit box.
No Commissions: Why a compensation model based on stock and growth is superior to commissions, citing Charlie Munger's famous quote on incentive plans.
The Future of SBA: Chip's prediction on the future of the 7(a) program and why he believes the loan size limit should be increased to $10 or $20 million.
AI & Banking: How artificial intelligence will automate the credit memo, cash flow analysis, and dramatically simplify SBA eligibility determination.

💬 Do you agree that the floating rate 7(a) loan is the best asset for any bank's books? Let us know in the comments!

🎙This episode is sponsored by:

Lumos

Lumos empowers your small business lending growth with cutting-edge analytics and streamlined applications that optimize your performance.

If you're ready to take your small business lending to the next level with cutting edge analytics visit https://lumosdata.com/

Shatterbox

Learn how Shatterbox can help you hire and invest in bright young talent without breaking the bank. Go to https://shatterbox.io/artofsba and set up a discovery call today.

Head to http://www.artofsba.com for more information and to sign up for our must-read monthly newsletter to stay up to date with The Art of SBA Lending.

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