Of
Nigerian and Black American descent (her father being a
Yoruba man from
Lagos and her mother being Black American[4]), Olayiwola was born in
Chicago.[5] When Olayiwola was a child, her father was abruptly deported to
Nigeria, forcing her mother to struggle alone to raise and support Olayiwola and her siblings. Olayiwola occasionally writes about the pain of growing up without her father physically present.[6][7]
When speaking to Boston Hassle about how she discovered performance poetry, Olayiwola stated, “I used to write all kinds of things when I was in middle school. I was running for electoral office in eighth grade, and my speech was a poem. But it was a high school teacher who suggested Louder Than a Bomb, which is the largest youth spoken-word festival in the world that happens in Chicago. It was the first time I heard other young people writing well-crafted poems, and also the first time I was able to come up with what I thought at the time was a very cohesive piece. And I haven’t stopped writing since that moment.”[8]
As an undergraduate, she performed poetry non-competitively on campus at the University of Illinois.[9]
In 2010, after finishing her degree, Olayiwola moved to Boston to serve as an
AmeriCorps*VISTA for the National
Coalition for the Homeless.[10][11] She worked as the dean of enrichment at
Codman Academy for five years and volunteered at Pine Street Inn, a homeless shelter in Boston.[12]
Her first poetry collection, i shimmer sometimes, too was released in 2019 by
Button Poetry.[15][16]
In 2020 her work was included in the exhibition Women Take the Floor at the Museum of Fine Arts, Boston.[17][18]
Olayiwola is the Artistic Director at Massachusetts Literary Education and Performance (MassLEAP), an artistic nonprofit that empowers
Massachusetts youth through writing, social justice, and community.[19]
Olayiwola founded and led the first Roxbury Poetry Festival hosted at Blair Lot in
Nubian Square on June 5, 2021. The festival included a keynote address from 2020
Pulitzer Prize winning poet,
Jericho Brown and a live poetry slam, which awarded two local poets with Button Poetry book deals.[20][21]
In September 2022,
MFA and
ICA-featured multimedia artist Stephen Hamilton unveiled a piece he created in Olayiwola's likeness titled, “Iya Ogun” Acrylic, enamel, and natural dyes and pigments on wood and Hand-woven and hand-dyed fabric.[22][23][24]
In October 2022, she performed her poem, "SESTINA", at a
Celtics pre-game ceremony for the opening game of the 2022-23
NBA season at
T.D. Garden in honor of
Bill Russell.[25][26]
In November 2022, The Boston Globe announced that Olayiwola and Bing Broderick would create a bookstore in
Fields Corner that would be “culturally curated, radically influenced, and locally inspired.” They plan to open the store by the fall of 2023.[27]
Personal life
In 2016, Olayiwola began a relationship with New York City's former Poet Laureate, Crystal Valentine.[28] In 2017, they collaborated on poetry show, LEVITATE, focused on Black queer womanhood.[29] In 2023, Olayiwola and Valentine became engaged.[30]
In 2014, Olayiwola won the Individual World Poetry Slam in Phoenix. In 2015, she tied for 7th place with
Javon Johnson at the competition in D.C.[31]
National Poetry Slam
In an effort to create a free poetry slam space that centered the voices of Black poets, Olayiwola and Janae Johnson co-founded The House Slam in October 2014 at the Haley House Bakery Café in
Roxbury.[32]
In August 2015, Olayiwola coached and competed with House Slam at the
National Poetry Slam Oakland where they beat 71 other teams to become champions in their first year.[33] House Slam was the first Boston poetry slam team to compete at NPS, and thus, was the first Boston poetry slam team to win nationals.[32] In its founding year, House Slam also became “the first venue in history to simultaneously hold the country’s three major slam titles,” according to the event's host,
Poetry Slam Inc.[33]
In 2016 in
Decatur, and again, in 2017 in Denver, House Slam, coached by Olayiwola, won their way back to the NPS Final Stage and ranked third both years.[34][35]
Brave New Voices
In August 2016, Olayiwola coached Mass LEAP's first team at
Brave New VoicesD.C. where they placed in the semi-finals. In 2017, she coached Mass LEAP's team at BNV
Bay Area, which placed 2nd overall, and earned a spot performing on final stage for 3,200 people at the
San Francisco Opera House.[36] Again, in 2018, Olayiwola coached Mass LEAP's team at Brave New Voices
Houston, where they took 4th place overall.[37]
College Unions Poetry Slam Invitational
In April 2017, Olayiwola coached the Wellesley Out Loud team and the Fundamental Lyricists of
Wheelock team, both in their first year of existence, at the College Unions Poetry Slam Invitational
University of Illinois Chicago. Team Wellesley placed 35th and Wheelock placed 18th, out of 72 teams.[38] In April 2018, Olayiwola coached
Wellesley Out Loud's team at CUPSI
Temple University, where they ranked 4th out of 66 teams.[39]
Awards
Isabella Stewart Gardner Museum, where Olayiwola was the artist in residence in 2021.[40]
Championships
2014 Individual World Poetry Slam Champion,
Phoenix[41]
"
Dorothy Dips A Toe Into A Hotel Pool After Being Warned The Water Would Need To Be Drained If A Black Person Swam In It, 1953 Las Vegas", Indiana University Press, 2020[76]
"Finding a Black Queer Woman Love", Button Poetry, 2020[77]
Of
Nigerian and Black American descent (her father being a
Yoruba man from
Lagos and her mother being Black American[4]), Olayiwola was born in
Chicago.[5] When Olayiwola was a child, her father was abruptly deported to
Nigeria, forcing her mother to struggle alone to raise and support Olayiwola and her siblings. Olayiwola occasionally writes about the pain of growing up without her father physically present.[6][7]
When speaking to Boston Hassle about how she discovered performance poetry, Olayiwola stated, “I used to write all kinds of things when I was in middle school. I was running for electoral office in eighth grade, and my speech was a poem. But it was a high school teacher who suggested Louder Than a Bomb, which is the largest youth spoken-word festival in the world that happens in Chicago. It was the first time I heard other young people writing well-crafted poems, and also the first time I was able to come up with what I thought at the time was a very cohesive piece. And I haven’t stopped writing since that moment.”[8]
As an undergraduate, she performed poetry non-competitively on campus at the University of Illinois.[9]
In 2010, after finishing her degree, Olayiwola moved to Boston to serve as an
AmeriCorps*VISTA for the National
Coalition for the Homeless.[10][11] She worked as the dean of enrichment at
Codman Academy for five years and volunteered at Pine Street Inn, a homeless shelter in Boston.[12]
Her first poetry collection, i shimmer sometimes, too was released in 2019 by
Button Poetry.[15][16]
In 2020 her work was included in the exhibition Women Take the Floor at the Museum of Fine Arts, Boston.[17][18]
Olayiwola is the Artistic Director at Massachusetts Literary Education and Performance (MassLEAP), an artistic nonprofit that empowers
Massachusetts youth through writing, social justice, and community.[19]
Olayiwola founded and led the first Roxbury Poetry Festival hosted at Blair Lot in
Nubian Square on June 5, 2021. The festival included a keynote address from 2020
Pulitzer Prize winning poet,
Jericho Brown and a live poetry slam, which awarded two local poets with Button Poetry book deals.[20][21]
In September 2022,
MFA and
ICA-featured multimedia artist Stephen Hamilton unveiled a piece he created in Olayiwola's likeness titled, “Iya Ogun” Acrylic, enamel, and natural dyes and pigments on wood and Hand-woven and hand-dyed fabric.[22][23][24]
In October 2022, she performed her poem, "SESTINA", at a
Celtics pre-game ceremony for the opening game of the 2022-23
NBA season at
T.D. Garden in honor of
Bill Russell.[25][26]
In November 2022, The Boston Globe announced that Olayiwola and Bing Broderick would create a bookstore in
Fields Corner that would be “culturally curated, radically influenced, and locally inspired.” They plan to open the store by the fall of 2023.[27]
Personal life
In 2016, Olayiwola began a relationship with New York City's former Poet Laureate, Crystal Valentine.[28] In 2017, they collaborated on poetry show, LEVITATE, focused on Black queer womanhood.[29] In 2023, Olayiwola and Valentine became engaged.[30]
In 2014, Olayiwola won the Individual World Poetry Slam in Phoenix. In 2015, she tied for 7th place with
Javon Johnson at the competition in D.C.[31]
National Poetry Slam
In an effort to create a free poetry slam space that centered the voices of Black poets, Olayiwola and Janae Johnson co-founded The House Slam in October 2014 at the Haley House Bakery Café in
Roxbury.[32]
In August 2015, Olayiwola coached and competed with House Slam at the
National Poetry Slam Oakland where they beat 71 other teams to become champions in their first year.[33] House Slam was the first Boston poetry slam team to compete at NPS, and thus, was the first Boston poetry slam team to win nationals.[32] In its founding year, House Slam also became “the first venue in history to simultaneously hold the country’s three major slam titles,” according to the event's host,
Poetry Slam Inc.[33]
In 2016 in
Decatur, and again, in 2017 in Denver, House Slam, coached by Olayiwola, won their way back to the NPS Final Stage and ranked third both years.[34][35]
Brave New Voices
In August 2016, Olayiwola coached Mass LEAP's first team at
Brave New VoicesD.C. where they placed in the semi-finals. In 2017, she coached Mass LEAP's team at BNV
Bay Area, which placed 2nd overall, and earned a spot performing on final stage for 3,200 people at the
San Francisco Opera House.[36] Again, in 2018, Olayiwola coached Mass LEAP's team at Brave New Voices
Houston, where they took 4th place overall.[37]
College Unions Poetry Slam Invitational
In April 2017, Olayiwola coached the Wellesley Out Loud team and the Fundamental Lyricists of
Wheelock team, both in their first year of existence, at the College Unions Poetry Slam Invitational
University of Illinois Chicago. Team Wellesley placed 35th and Wheelock placed 18th, out of 72 teams.[38] In April 2018, Olayiwola coached
Wellesley Out Loud's team at CUPSI
Temple University, where they ranked 4th out of 66 teams.[39]
Awards
Isabella Stewart Gardner Museum, where Olayiwola was the artist in residence in 2021.[40]
Championships
2014 Individual World Poetry Slam Champion,
Phoenix[41]
"
Dorothy Dips A Toe Into A Hotel Pool After Being Warned The Water Would Need To Be Drained If A Black Person Swam In It, 1953 Las Vegas", Indiana University Press, 2020[76]
"Finding a Black Queer Woman Love", Button Poetry, 2020[77]