Secrets of a Billion-Dollar Mortgage Team w/Anthony Contento and Michele Steko

Art of Mortgage Marketing

Businesses with strong team cultures crush the competition, outperforming by a jaw-dropping 200%. Yet in the relentless, high-pressure world of mortgages—where sales targets reign supreme—many leaders miss the mark on building the trust and collaboration that fuel sustainable success. Without a clear vision or a united team, scaling feels like trying to sprint through quicksand.

What if the secret to a billion-dollar business wasn’t grinding harder or chasing the next shiny object, but creating a culture so magnetic that top talent lines up to join your team, your clients can’t stop raving, and growth becomes almost effortless?

Most mortgage pros think hustle and rapid growth are the keys to the kingdom. But here’s the hard truth: chasing short-term wins might actually be blocking your path to long-term greatness. What if the real game-changer is doing less—but doing it better—anchored in culture, purpose, and servant leadership with a patient, long term approach?

In this episode, we sit down with Anthony Contento and Michele Steko of Sherwood Mortgage Group, who have cracked the code on building a billion-dollar team. They reveal how they fostered a family-like culture that inspires loyalty, strategically scaled by putting people before profits, and navigated tough markets with grace, grit, and innovation.

You’ll also learn:

• The power of building a “family culture” that attracts and retains top talent—because people don’t join companies, they join people.
• How to thrive in any market, even when the wind is in your face, by focusing on what you can control and staying intentional with your actions.
• Why servant leadership wins the long game, and how putting people first creates magnetic, lasting success.
• The timeless secret to building billion-dollar relationships: connecting with 2-3 COIs (centers of influence) a day and compounding those connections into massive results.
• How to master your mindset and self-image to overcome fear, imposter syndrome, and self-doubt—because you can’t outperform the belief you have in yourself.
• Why alignment matters more than chasing shiny objects, and how to find your lane for authentic, unstoppable growth.
• How to manage challenges with gratitude and grace, and turning adversity into your greatest asset.

Guest Bio

Anthony Contento is the co-founder and CEO of Sherwood Mortgage Group, a leading mortgage brokerage in Canada. With a career spanning over two decades in the financial industry, Anthony has been instrumental in the company’s rapid growth since its inception in 2008. Under his leadership, Sherwood Mortgage Group has expanded to over 100 agents across five provinces and has consistently surpassed the billion-dollar mark in mortgage originations. Anthony’s expertise in both banking and mortgage brokering allows him to offer a wide range of solutions to clients, ensuring personalized and effective financial strategies.

Michele Steko is the Vice President of National Broker Relations at Sherwood Mortgage Group. Michele joined the executive team with a wealth of experience in the mortgage industry, bringing a strong focus on fostering relationships and enhancing broker support. Her role involves ensuring smooth communication and collaboration among brokers spread across different provinces, contributing to the company’s cohesive and supportive culture. Michele’s dedication to professional excellence and her ability to navigate the complexities of the mortgage market make her a valuable asset to Sherwood Mortgage Group. To learn more visit https://sherwoodmortgagegroup.com/.

About Your Hosts

Considered by many to be the nation’s leading Mortgage Marketing Coach, Doren Aldana is the founder of several highly acclaimed training programs, including Autopilot Referral Systems, Client Acceleration Formula and the 7-Figure Lender Academy. He is a contributing author for Mortgage Professional America, CMP Magazine, The Mortgage Journal, and other mortgage industry publications. He is also the founder of the #1 mortgage marketing group on Facebook, The Art of Mortgage Marketing. Since 2005, Doren has trained thousands of mortgage professionals how to utilize his mortgage marketing secrets to close more deals with less effort, regardless of market conditions. In fact, due to his high-impact mortgage marketing solutions (and a whack-load of success stories), Doren was awarded the prestigious “Best Industry Service Provider” award three years in a row at the Canadian Mortgage Awards. Won the BEST INDUSTRY SERVICE award three times in a row.

Penny Wrightly is a seasoned mortgage professional and expert in creative lead generation. With years of experience in the industry, she has built a reputation for thinking outside the box to find opportunities where others don’t. Penny specializes in helping mortgage pros expand their networks, create valuable partnerships, and boost their business even in challenging markets. Her hands-on approach and innovative strategies have made her a sought-after speaker and coach for those looking to thrive in the competitive world of real estate and finance.

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