When former NFL player Walter Mendenhall founded the social enterprise Male Mogul Initiative in 2017, his goal was to positively transform the way young men live and lead in their communities and hopefully alter the trajectory of those from disadvantaged backgrounds.
Male Mogul has since continued to make an impact and expand its footprint with new business opportunities to not only help young men establish themselves but also help others in the process. The agency has helped thousands of young people in Chicago with professional opportunities and personal growth through mentorship, leadership, entrepreneurship and workforce development programming.
The latest expansion for Male Mogul is the acquisition of California-based financial technology company Helpwithmyloan, known for using AI to simplify and speed up the loan application process for small business owners as well as commercial and residential investments, Mendenhall said.
The Chicago office of Helpwithmyloan, which is operating from Male Mogul’s space at 29 E. Madison St., officially launched in February. Helpwithmyloan’s two founding partners have stayed on and continue to support the new branch by providing job training for young men through Male Mogul’s workforce development programming.
Jeremiah Swint, 25, of Chicago, has been with Male Mogul since June 2024 and offers his expertise in financial literacy through teaching and workshops. He has had a keen interest in all things related to the stock market, trading and economics since he was a child, he said.
Swint is now a loan officer for Helpwithmyloan and said his ability to build relationships and work with people, coupled with his financial savvy, helped him excel at this opportunity.
“I knew I wanted to take this role and be more involved,” Swint said. “It’s amazing being able to get financing to people in an innovative way, to be that first ear to hear them out and seek out people’s visions and stories and how they want to mold the financing, and ultimately be able to get it to them.”
He started training in January for the job and will continue to learn as he goes, he said.
A lending platform is “not a totally new invention,” but what sets Helpwithmyloan apart, Swint said, is that it’s a platform that offers innovative guidance with financing.
“Helpwithmyloan is for everyone,” Swint said. “It’s for impact. It’s for storytelling. It’s for assistance. It’s for collaboration.”
Swint said he is “excited for the success stories and the relationships that we’re building and going to build.”
“Relationships are everything to me,” Swint said. “Money is in relationships, it’s not just in work. You have to work and build relationships and then the money comes with the people you impact as well.”
Male Mogul acquired Helpwithmyloan in partnership with Chicago-based financial firm Loyd & Co., which is in charge of operations and the strategic vision for Helpwithmyloan. Male Mogul’s role is to help build out the Chicago office of Helpwithmyloan.
Male Mogul’s workforce development programming aims to give young men from the South and West sides of Chicago job opportunities by training and mentoring them for specific roles. Mendenhall said most recently they have trained men in their 20s in loan brokering, client management, lender analysis and more with the help of Loyd & Co. and the founding partners of Helpwithmyloan.
Mendenhall said there are about 10 people working for the local office, but the opportunities are “limitless.”
“We know that there’s always going to be the need for access to capital, so the job capabilities are endless and that’s what excites us,” Mendenhall said.
He said he hopes to employ over 50 young people over the next few years through Helpwithmyloan.
“We’re helping young people find their purpose, helping them identify their gifts and skills and talents while also teaching financial literacy and wealth building,” Mendenhall said.
With any merger and acquisition, there’s a “transition period,” said Mendenhall, a Chicago-area native and a former player for the Philadelphia Eagles, Indianapolis Colts, Buffalo Bills and Cincinnati Bengals who pivoted to entrepreneurship and nonprofit administration.
“There’s a learning curve, and we’ve been experiencing that, but we have learned a lot and we have made pivots and gained a lot of experience in a very short amount of time,” Mendenhall said.
Jarryd Loyd, managing partner of Loyd & Co., said he has known Mendenhall for about 20 years and started working with him through Male Mogul early on to help increase workforce development opportunities for Black and brown youth. He said that was done by figuring out the needs of the communities that Male Mogul serves, determining what skill sets are in demand and how to create jobs to meet those needs while employing young people.
Loyd said Helpwithmyloan caught the company’s attention because of its ability to provide access to capital efficiently to under-resourced groups not just in Chicago but around the country. The company already had over $850 million in loan deals.
“It’s extremely hard for small businesses that don’t have traditional collateral to get access to funds, specifically if you’re from a disadvantaged demographic,” Loyd said. “Helpwithmyloan has had a history of providing access to capital to small businesses and commercial real estate investors that usually get denied by banks, and so we saw it as an opportunity to provide additional resources to accelerate that access.”
While the loan process traditionally takes from 60 to 90 days, Loyd said the team behind Helpwithmyloan tries to get it done within 10 to 20 days by using the company’s technology to speed up the process, such as giving pre-approval and finding a lender.
Many loan deals are already in the pipeline, he said, and the young people working to get those deals across the finish line are “excited and earning and seeing the power of helping small business owners access capital,” Mendenhall said.
Male Mogul is also working toward expanding to a 50,000-square-foot warehouse in Englewood to house the Helpwithmyloan office as well as other divisions of Male Mogul, Mendenhall said, while retaining the current space in the Loop.
“What started as an entrepreneurship program has really blossomed into changing young people’s lives,” Mendenhall said. “It’s just truly amazing when you have good intentions, when you have a dream, when you want to solve a problem, a major problem, and what you are able to do when you stick with it and you think outside the box.”
