When Allstate bought the personal insurer National General last summer, the company needed funds from the bond market to support the acquisition.

Allstate, a well-known bond issuer, could have visited the capital markets with ease, but CFO Mario Rizzo wanted to try something different.

He approached CEO Thomas Wilson about appointing a minority-owned firm to lead the deal alongside Allstate's usual suite of Wall Street banks.

Wilson, Rizzo said, encouraged him to go further and do the bond deal solely with minority-led firms.

The discussion took place in July, while America underwent one of its greatest periods of social unrest — a time when the spotlight was on companies' efforts to tackle inequity, magnified by consumers and shareholders increasingly holding corporate citizens accountable for their actions.

"Minority-owned firms were always part of our syndicates, but they didn't play a prominent role," Rizzo said.

James Reynolds, Loop Capital's founder and CEO, met with Allstate's Wilson to determine whether minority-owned banks could pull off a deal without their deep-pocketed, bulge-bracket peers.

Rizzo said Allstate had some doubts over whether minority-owned firms like Loop and Siebert Williams Shank had the breadth of sales to distribute a $1 billion bond or the technology to facilitate such a hefty order book.

But to help erase concerns, Allstate and the lead banks conducted hefty investor meetings ahead of the bond sale to garner interest in the deal, and importantly, expose Loop, SWS, and other arrangers on the deal to top-tier investors.

In the end, the minority-led banks got more than enough demand for the bond. Allstate increased the sale to $1.2 billion from $1 billion, and the banks proved they could lead a corporate deal without a bulge-bracket lender anchoring the transaction.

"On the day, it looked and felt like every other debt deal I've been associated with," Rizzo said.

And going forward, Rizzo hopes this initiative becomes the norm not just at Allstate but also throughout corporate America's capital-raising efforts.

He also hopes minority-led firms will capitalize on this momentum to grow their share of the investment-banking pie.

"I hope it's emboldened them to say there is a level of dissatisfaction with playing a secondary role," Rizzo said. "These are firms with talented people and strong capabilities."

Last year, diverse firms participated in about 29% of investment-grade bond deals in 2020, according to Refinitiv data, up from about 22.5% in 2010.

While it's important to participate in dealmaking, these firms want to play lead roles on companies' fundraising requirements. But without the deep balance sheets of peers such as Citibank or JPMorgan, companies and big banks will need to help diverse firms get a greater share.

Lenders like Deutsche Bank and Citibank have already appointed minority-owned shops to conduct their own debt deals, and momentum is shifting as more companies look to diverse firms.

Insider spoke with key players about their journeys throughout Wall Street, the trials they've had to overcome, and what they're doing to ensure diverse communities can prosper in a post-pandemic America.

Eric Van Standifer, CEO of Blaylock Van. Eric Van Standifer is the CEO of Blaylock Van

After more than 30 years in banking, Standifer describes himself as one of the industry's "longbeards."

Before becoming a CEO and cofounder, he cut his teeth in retail brokerage at Merrill Lynch in the '80s before opening Robert Van Securities in 1991.

Standifer took out a second mortgage on his home to start the business. Based in California, he watched as fellow Black bankers plied their trade in Chicago and New York.

"I used the analogy of Kevin Costner in 'Dances with Wolves.' In Oakland, it was like being at an outpost," he told Insider. "But it was about running my own shop. I had this entrepreneurial monster inside of me."

He also saw both success and hardship for the few African Americans on the investment-banking floor.

Standifer said he was one of 55 African American retail brokers at Merrill. People would quiz him over how he could recite an exact figure so quickly for a team with thousands of traders.

"Because we all knew one another," he said. "There's a commonality of experiences among folks of color working on Wall Street."

Whether it's being overlooked for opportunities or feeling pressure to bring your best, knowing that the next opportunity might be far away, Standifer related to this tiny pocket of colleagues.

"I know what they can bring and can identify with the bulls--- they've been through," he said.

Standifer continues to mentor young, aspiring African Americans and others from minority communities who want to dip their toes in the financial-services pool.

His firm grew from an equity-research provider into municipal-bond deals and now has sights on the US corporate-bond space.

It led a $2.5 billion transaction for Citibank in January and participated in a $10 billion deal for the Google parent company Alphabet last summer.

In 2007, Standifer teamed up with Ronald Blaylock, another stalwart in the minority-owned world of capital markets, and the firm is known today as Blaylock Van.

While he acknowledges that there is a greater awareness of inequity than he's ever seen, Standifer's aware that a lot more can be done. Minority-owned firms are getting what amounts to a sliver of Wall Street's investment-banking fees.

"The amount of bond issuance in the US is staggering. And if you total all the minority-owned firms and the business we get, it's a fingernail," Standifer said. "But today, shareholders are demanding diversification and saying, 'Let's get something that looks a bit more like America.'"

Ronald Blaylock, partner at Blaylock Van. Mike Pont/Getty

It's rare that a conversation about the history of minority-owned firms ends without mention of Ron Blaylock.

Peers credit Blaylock as a pioneer for African Americans on Wall Street.

He completed stints at Citibank and UBS, and before partnering with Standifer's firm in 2007, he founded Blaylock & Company in 1993.

Today he's also the founder and managing partner at GenNx360 Capital Partners, a private-equity firm managing $1.7 billion in investments.

Blaylock has received countless awards, including being named one of Black Enterprise's "Most Powerful Blacks on Wall Street," and he has served on the boards of Pfizer and the New York University.

He also had a four-year stint, including a season with former New York Knick Patrick Ewing, on Georgetown University's famed college basketball team in the '80s while getting a degree in finance.

While Blaylock's now busy in private equity, Standifer said he remains a "rainmaker" for Blaylock Van.

"Ron's an active shareholder that is very well connected and a valuable partner in this business," Standifer said.

Those connections have proved integral. When Blaylock & Company was in its infancy in 1994, he got Bear Stearns to inject 25% equity in the business for $10 million.

And while Bear Stearns was a casualty of the financial crisis, firms like Blaylock Van have only grown.

When Jackie Robinson joined the Brooklyn Dodgers, he brought down the sport's color barrier that restricted Black players from joining Major League Baseball.

"Nobody knew how great baseball could be until everyone could play," Sidney Dillard, the head of corporate investment banking at Loop Capital, told Insider.

A similar case is playing out, she said, as more US blue-chip companies recognize experienced minority-owned firms and appoint them to manage their capital needs, rather than cycling through the US' top six investment banks.

Loop, a mainstay in the US municipal-bond market, tapped Dillard precisely to forge greater ties with corporate bond issuers.

Having built relationships with corporate clients and institutional investors during her 15 years with Northern Trust, she joined Loop in 2002. What started as passive assignments on bond deals has since morphed into leading roles for Loop with Allstate, Verizon, and Deutsche Bank, among others in the past year.

Dillard's also not shy about addressing Wall Street's failure to achieve greater diversity. She's determined to ensure today's conversation on racial and gender equity is more than a flash in the pan.

"Our job is to keep it front and center," she said. "These things are easy to respond to in a moment before going back to business as usual."

While almost two-thirds of Loop's staff consists of employees from minority communities, Dillard wants greater progress throughout the industry.

She laments that not enough people of color are recruited by the biggest firms in financial services, which then limits their chances of nabbing leadership positions elsewhere.

A wider search for talent, beyond the top Ivy League schools, might be a starting point, but firms must also assess how to retain that talent.

"You don't find Black and brown people because they're not getting early access to these opportunities," she said. "This is a role we want to play, but everybody has to do it for the tide to lift all the boats."

James Reynolds, CEO of Loop Capital. Ramin Talaie/Getty

Experienced bankers have credited James Reynolds as a trailblazer for minority-owned financial institutions.

Standifer, of Blaylock Van, said he watched admirably as Reynolds put together Loop Capital in Chicago. And Ron Quigley of the service-disabled and veteran-owned investment bank Mischler Financial said he couldn't thank Reynolds, among others, enough for sacrifices made to establish a footprint for minority-led banks.

Reynolds earned his stripes at Chicago-based Paine Webber and Merrill Lynch in the '80s and early '90s, where he focused on municipal-bond sales and trading.

He established Loop with six staff in 1997 on the back of his experience with municipal fundraising.

Today, Loop's founder and CEO has the ear of America's investment-grade C-suite, including Allstate's Wilson. He oversees a workforce of some 200 individuals, of which roughly two-thirds hail from diverse backgrounds.

And alongside Dillard, Reynolds has morphed Loop into both a corporate- and municipal-investment bank.

The deal for Allstate was complemented by a green bond for Verizon last year, and this year's transaction for Deutsche Bank.

Suzanne Shank, CEO of Siebert Williams Shank. Siebert Williams Shank

Suzanne Shank is adamant that diversity initiatives gain traction at the board level, an approach she personifies as CEO of Siebert Williams Shank.

Last year, her firm launched the Clear Vision Impact Fund in partnership with Microsoft. The fund seeks $250 million to invest in small- and medium-sized businesses, particularly those in underrepresented areas. In its first fundraising round in March, Clear Vision obtained more than $100 million in commitments.

SWS also committed at least $200,000 at the end of last year to support historically Black colleges and universities, such as Spelman College and Howard University.

As an advocate, there's no better voice than Shank.

Like Dillard, she wants to keep the conversation on race and gender at the forefront of corporate America.

"We're hopeful it's not just a moment in time but something institutionalized in companies' thinking," Shank said.

A former engineer, she pivoted to banking in the '80s at a time when few women saw a career path within Wall Street's notorious boys' club.

After about nine years in finance, at firms like the now-defunct Grigsby Brandford, Shank was tapped by Muriel Siebert — an equity trader and the first woman to own a seat on the New York Stock Exchange. Siebert envisioned an investment bank wholly owned by women, and Shank proved the ideal tonic for an industry in need of a shake-up.

In 1996, Siebert and Shank cofounded their investment bank, then known as Siebert Cisneros Shank.

The firm earned its keep in the municipal space, but since merging with Williams Capital in 2019, the firm has branched out to lead corporate bond deals for Verizon, Deutsche Bank, and Allstate in the past eight months.

Given the scarcity of corporate opportunities, however, Shank leaves little room for error. While Citibank can recover from a $900 million blunder, small, minority-owned shops can't afford to slip up when a blue-chip deal comes along. The spotlight is on them, and every deal is a chance to prove they have the chops to compete alongside the likes of Citibank or JPMorgan.

"We don't get second chances," she said. "If a deal doesn't go right, we might never get that chance again, and that could hurt our relationships with other clients."

Chris Williams, chairman of Siebert Williams Shank. Siebert Willliams Shank

One of Chris Williams' most significant transactions was a $100 million deal for Sallie Mae in 1994, then a government entity that provided education loans.

It was the first transaction for his shop, Williams Capital, after he left Lehman Brothers' debt capital markets arm.

During his time at Lehman, Williams turned Sallie Mae, a frequent bond issuer, into a key client for the firm. Now, under Williams Capital, he wanted to maintain that relationship.

He teamed up with Jefferies after his father-in-law introduced him to Rich Handler, who led Jefferies' high-yield business at the time. Williams Capital operated as an entity of Jefferies, which held a 49% stake in the firm.

"Leaving Lehman, the team at Sallie Mae told me, 'If you're able to bring the same quality of deals under Jefferies, I'll make sure we do business with you,'" Williams told Insider. "Had we not had that endorsement, I don't know what would've happened."

Within two years, Williams spun off from Jefferies, but the investment firm had the right to remain a limited partner. Williams then opted to buy the firm out.

According to Williams, Handler, who is now Jefferies' CEO, jokes with Williams that his subsequent growth was a testament that he got away too cheaply.

While the firm's enjoyed some success, it's the tie-up with Suzanne Shank that advanced its progress as a minority-owned firm.

In 2019, Siebert Williams Shank was born, and it became the first minority-led investment bank to crack the top 10 underwriter rankings for municipal-bond issuance. In addition to the municipal- and corporate-bond market, SWS is also digging into advisory work for mergers and acquisitions and is building out an asset-management business.

Alongside Shank, SWS has poured resources into an internship program focused on minority communities and also helps screen candidates for its clients.

Tech and telecom outfits including Microsoft, Apple, and Comcast, among others, were part of the first round of fundraising for the earlier-mentioned Clear Vision Impact Fund, Williams said.

Proceeds are being invested in opportunities that support further employment for diverse individuals and formerly incarcerated people reentering the world.

And while minority-owned firms remain the biggest advocates for diverse communities, Williams reckons corporate America is also getting onboard.

"Speaking with our corporate partners, tech in particular, they want to think through investments beyond securities. Investments that can be more helpful and positive on the broader community," he said.

Annie Seelaus, CEO of R. Seelaus & Co. R. Seelaus

The financial crisis of 2008 proved a watershed moment for Annie Seelaus.

After 10 years with HSBC's investment-grade corporate bond desk in London and New York, she decided to join the family business.

"This was a now-or-never moment to see if we could do institutional credit," Seelaus told Insider.

It was a risk, taking on something untested amid one of the most uncertain periods in market history.

But she was not deterred. In 2009 she joined the firm founded by her father in 1984, to construct institutional credit sales and trading.

"I was like a one-woman show in corporate bonds for a while, but I leveraged the firm's liquidity in municipal-bond coverage for corporates," she said.

That leverage enabled Seelaus to pivot not only toward corporate bonds, but also other asset classes like treasury trading, and mortgage-backed securities. Or as Seelaus put it, "the whole enchilada."

When her father retired in 2015, she became CEO and was driven by the idea of a firm owned by women.

"Sometimes, people don't appreciate the scale of the problem we are trying to solve," Seelaus said. "I'm not sure companies fully realize how institutionalized the problem of lack of women is, so that's been a challenge getting people to understand that."

Indeed, the proportion of women in leadership roles in financial services was just 22% at the end of 2019, a report from Deloitte showed. It's projected to grow to 31% by 2030, but that's still subpar, according to the report.

To help, Seelaus' asset-management arm launched a rotational job program in March alongside Apple for young women of color to enter and learn the trade.

While Seelaus said women have struggled to be seen in an industry dominated by men, she's hopeful the tide is turning as companies double down on diversity and inclusion initiatives.

"We're trying to break through our label and be first on merits," Seelaus said. And today, women comprise 75% of R. Seelaus' C-suite.