Ashley Weatherspoon and Ashley North didn’t imagine their laid-back friendship would bloom into a six-figure brand, but what started as an unlikely bond on a “football wives” trip has grown into Ask Ashley, their widely loved podcast exploring womanhood, friendship, motherhood, and identity with equal parts warmth and wit.
With that in mind, we’re spotlighting their success story and close connection for Black Women’s History Month.
Both women were navigating the world of dating professional athletes when they first met in a world often portrayed with glitz, glam, and glossy Instagram facades.
“We used to feel bad sharing the story,” Ashley Weatherspoon told BOSSIP with a laugh. “But now, especially with all the WAGs shows, it actually makes sense.”
On a trip filled with curated poolside photo ops and materialistic posturing, the two Ashleys found themselves craving authenticity.
“At one point, I turned to her and said, ‘God, I wish I had a joint,’” Ashley Weatherspoon recalled. “And she was like, ‘Damn, me too.’” What followed was a candid, honest conversation — the first of many — that revealed a real connection beyond shared lifestyles or social circles.
That single moment sparked a deep and lasting friendship, one that would stretch across coasts and decades.
Today, Ashley Weatherspoon and Ashley North, who refer to each other as chosen sisters, live on opposite ends of the country but stay closely tethered through constant FaceTime calls and mutual support.
“We’re those friends you see memes about,” said Ashley North. “We’ll just sit on FaceTime folding laundry or picking up the kids. It keeps us part of each other’s daily lives.”
Their podcast Ask Ashley, now in its fourth season, has become a sleeper hit and testament to the power of natural chemistry, not manufactured partnerships. Unlike many podcast duos assembled by producers hoping to force magic on the mic, the Ashleys’ bond was built off-mic first.
“We’d go out, and people never wanted us to leave,” Ashley Weatherspoon recalled. “One of our friends’ tough, no-nonsense partners actually requested dinner with us again. That’s when we knew we had something. If we cracked him, we could crack a population.”
The podcast, which touches on everything from pop culture to parenting to personal growth, blossomed from that realization, as well as North’s lingering frustration from her time on reality television.
“I was on a show about WAGs that promised I could show my career and my life as a mom,” she explained. “But instead, they painted me as a weak girl chasing marriage. That wasn’t my story.”
In reality, Ashley North styles some of the biggest names in sports and entertainment, from Kevin Hart to Dodgers star Mookie Betts. Her career, hustle, and motherhood deserve center stage, and she knew she needed a platform that reflected that truth.
“Ashley had already created a space with Dear Young Queen,” she said about Weatherspoon. “So we joined forces.”
The result was Ask Ashley, a blend of authenticity and light-hearted insight that immediately resonated.
“We’re a really good time,” said Ashley Weatherspoon. “And we’re not out here just talking sex or engaging in gender wars. We’re creating real content that reflects who we are.”
Their early $30,000 investment in the podcast was a leap of faith, but it paid off. Post-pandemic shifts in media consumption, coupled with heightened investment in Black female voices following the 2020 racial reckoning, created a unique window for Ask Ashley to shine.
“Suddenly, brands were looking for our exact voice,” Ashley said. “Not too raunchy, not combative — just relatable, authentic women speaking their truth.”
Their voice proved magnetic. Major brands took notice, and the podcast became a rare financial success in an oversaturated field.
“It’s surreal,” Ashley Weatherspoon said “But we built this. We showed up every week. We didn’t let up.”
Much of the podcast’s appeal lies in its warmth and its segments that let listeners feel like part of the friendship. “Question Time” remains a fan favorite, an unfiltered exchange that tests how well the Ashleys really know each other after 15 years. And for North, “TV Time” is a chance to indulge her inner critic.
“I’m basically Roger Ebert,” she joked.
Yet perhaps what resonates most deeply is the duo’s shared reverence for their mothers, both raised primarily by strong, hardworking women.
“Their influence comes through in everything,” Ashley Weatherspoon told BOSSIP. “How we parent, how we move through the world, how we love.”
It’s these slices of real life, honest, unvarnished, and profoundly human, that make Ask Ashley more than just a podcast and more of a window into sisterhood and a celebration of what happens when two Ashleys show up as their full selves.
Ask Ashley, which is part of the Dear Young Queen podcast network, is available to stream HERE.
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