This Robin Hood Moment

What does it take to build a career when every step forward comes with a tradeoff—when choosing training means losing wages, when choosing stability means rearranging childcare, and when choosing your future means risking the little security you have today?For many New Yorkers, the road to stability isn’t a straight line—it’s a climb, one careful choice at a time.In this companion to our conversation with Brooklyn Workforce Innovations’ Executive Director Aaron Shiffman, we hear from Tiphany, a lifelong NYCHA resident who turned a moment of uncertainty into a path toward purpose. After coming across a flyer in her building lobby for the NYCHA Resident Training Academy—a program facilitated by BWI—Tiphany made a choice that would transform her life.As a single mother searching for stability, Tiphany faced the hard tradeoffs that define the cost of choice: balancing work and childcare, risking short-term income for long-term opportunity, and fighting through doubt to build something better for her family. Nearly a decade later, she’s risen from Caretaker to Property Maintenance Superintendent, overseeing the very kind of buildings she once called home.Through Tiphany’s story, we see what happens when access meets determination—and how investing in career mobility can help New Yorkers move from surviving to leading.Tune in for insightful discussions on shaping policies to uplift communities and #FightPoverty. Subscribe for more episodes wherever you listen to your podcasts.You can find transcripts and more episodes of "This Robin Hood Moment" at robinhood.org/podcasts.Thoughts? Guest suggestions? Email us at info@robinhood.org.Support Robin Hood’s work to elevate New Yorkers out of poverty at https://give.robinhood.org/give/61654/#!/donation/checkout?c_src=YT.LEARN MOREhttps://www.robinhood.org/https://www.facebook.com/robinhood/https://www.instagram.com/robinhoodnyc/https://www.linkedin.com/company/robin-hood/https://twitter.com/robinhoodnyc/

What does it take to rebuild your life when you’ve fallen through the cracks—after the job is gone, the rent’s past due, and there’s no safety net to catch you?In New York City, the margin for error is razor thin—especially for low-income workers. One missed paycheck can mean eviction. One illness can mean job loss. One childcare emergency can unravel a household. For many New Yorkers, there is no cushion. There is no safety net. There is only the cost of choice: working while sick, delaying care, or turning down opportunity because stability is always on the line.In this episode, we explore how workforce development can serve as a bridge—not just to employment, but to restored stability—after someone has already fallen through the cracks. Our guest is Aaron Shiffman, Executive Director of Brooklyn Workforce Innovations (BWI), a nonprofit that has spent over 25 years helping New Yorkers build in-demand skills and launch careers in industries like transportation, media production, woodworking, and construction. For BWI, training isn’t the finish line—it’s the starting point of long-term support and upward mobility.Together, we examine what it takes to help someone rebuild after crisis, how BWI navigates the gaps in public systems, and why meaningful employment remains one of the most powerful tools to fight poverty in New York City.Tune in for insightful discussions on shaping policies to uplift communities and #FightPoverty. Subscribe for more episodes wherever you listen to your podcasts.You can find transcripts and more episodes of "This Robin Hood Moment" at robinhood.org/podcasts.Thoughts? Guest suggestions? Email us at info@robinhood.org.Support Robin Hood’s work to elevate New Yorkers out of poverty at https://give.robinhood.org/give/61654/#!/donation/checkout?c_src=YT.LEARN MOREhttps://www.robinhood.org/ https://www.facebook.com/robinhood/https://www.instagram.com/robinhoodnyc/https://www.linkedin.com/company/robin-hood/https://twitter.com/robinhoodnyc/

What does it mean to chase opportunity when every step forward comes with a sacrifice?In New York City, the high cost of child care forces many parents—especially mothers—to make impossible choices between earning a living and being there for their children. For Marlyn, a mother of two in Inwood, balancing work, childcare, and her dreams for her family means constantly negotiating what she can afford to give up.In this episode, Marlyn shares her story of resilience and resourcefulness as she works to build a better life for her kids with support from Children’s Aid, a Robin Hood grantee providing early childhood education and family services across the city. Her story reveals what it really takes to raise a family in a city where love is abundant—but affordable child care is not.Tune in for insightful discussions on shaping policies to uplift communities and #FightPoverty. Subscribe for more episodes wherever you listen to your podcasts.You can find transcripts and more episodes of "This Robin Hood Moment" at robinhood.org/podcasts.Thoughts? Guest suggestions? Email us at info@robinhood.org.Support Robin Hood’s work to elevate New Yorkers out of poverty at https://give.robinhood.org/give/61654/#!/donation/checkout?c_src=YT.LEARN MOREhttps://www.robinhood.org/https://www.facebook.com/robinhood/https://www.instagram.com/robinhoodnyc/https://www.linkedin.com/company/robin-hood/https://twitter.com/robinhoodnyc/

What happens when every choice you make for your child comes at the cost of another?For parents living in poverty, raising a child in New York City can feel like navigating an impossible maze of tradeoffs. Do you skip work to care for a sick child and risk losing your job? Do you buy groceries or pay for internet so they can finish their homework? Do you move into a more affordable apartment—even if it means transferring your child out of a good school? While most parents make choices to give their kids more, low-income parents are often forced to choose which basic needs they can afford to meet.In this episode, we sit down with Phoebe Boyer, President & CEO of the Children’s Aid, to explore how poverty reshapes the possibilities of childhood. We’ll hear what’s at stake for kids when families live paycheck to paycheck, and the systemic investments—in education, health, housing, and family support — that can help children thrive. This is a conversation about protecting potential, and the urgent need to create a city where every child has a real shot at a better future.Tune in for insightful discussions on shaping policies to uplift communities and #FightPoverty. Subscribe for more episodes wherever you listen to your podcasts.You can find transcripts and more episodes of "This Robin Hood Moment" at robinhood.org/podcasts.Thoughts? Guest suggestions? Email us at info@robinhood.org.Support Robin Hood’s work to elevate New Yorkers out of poverty at https://give.robinhood.org/give/61654/#!/donation/checkout?c_src=YT.LEARN MOREhttps://www.robinhood.org/https://www.facebook.com/robinhood/https://www.instagram.com/robinhoodnyc/https://www.linkedin.com/company/robin-hood/https://twitter.com/robinhoodnyc/

How do you feed your family when the cost of groceries keeps climbing, but your paycheck doesn’t?In Harlem, Monique has learned to stretch every dollar, every meal, and every ounce of energy to keep food on the table for her children. But when the price of basic groceries rivals the cost of a utility bill, the choice between eating and keeping the lights on becomes painfully real.In this episode, Monique shares how the Food Bank for New York City—one of Robin Hood’s grantee partners—helps her family bridge that gap. Her story offers a human portrait of food insecurity in New York: a city of abundance where far too many still go hungry, and where every full plate comes at a price.Tune in for insightful discussions on shaping policies to uplift communities and #FightPoverty. Subscribe for more episodes wherever you listen to your podcasts.You can find transcripts and more episodes of "This Robin Hood Moment" at robinhood.org/podcasts.Thoughts? Guest suggestions? Email us at info@robinhood.org.Support Robin Hood’s work to elevate New Yorkers out of poverty at https://give.robinhood.org/give/61654/#!/donation/checkout?c_src=YT.LEARN MOREhttps://www.robinhood.org/https://www.facebook.com/robinhood/https://www.instagram.com/robinhoodnyc/https://www.linkedin.com/company/robin-hood/https://twitter.com/robinhoodnyc/

What happens when eating well isn’t a choice—but a calculation?When the cost of food forces impossible choices, what would you give up to keep your family fed? In this episode, This Robin Hood Moment welcomes Leslie Gordon, President & CEO of Food Bank For New York City, to explore how rising grocery prices, stagnant wages, and looming federal cuts to programs like SNAP are reshaping the daily realities for millions of New Yorkers. Leslie shares on-the-ground insights into how families weigh food against other essentials—housing, child care, healthcare—and what it will take to ensure no New Yorker has to choose between eating dinner and keeping the lights on.Tune in for insightful discussions on shaping policies to uplift communities and #FightPoverty. Subscribe for more episodes wherever you listen to your podcasts.You can find transcripts and more episodes of "This Robin Hood Moment" at robinhood.org/podcasts.Thoughts? Guest suggestions? Email us at info@robinhood.org.Support Robin Hood’s work to elevate New Yorkers out of poverty at https://give.robinhood.org/give/61654/#!/donation/checkout?c_src=YT.LEARN MOREhttps://www.robinhood.org/https://www.facebook.com/robinhood/https://www.instagram.com/robinhoodnyc/https://www.linkedin.com/company/robin-hood/https://twitter.com/robinhoodnyc/

What does home mean when it’s always just out of reach?For Michelle, finding an apartment wasn’t just about having a roof over her head—it was about reclaiming a sense of security after years of uncertainty. With support from Anthos|Home, a Robin Hood-funded organization helping New Yorkers use housing vouchers to move quickly into affordable homes, Michelle finally found a place to settle and breathe.In this episode, Michelle reflects on the emotional toll of searching for stability in one of the most expensive housing markets in the world, and what it means to finally hold the key to her own front door. Her story is a reminder that in New York City, the fight for housing is about more than rent—it’s about dignity, belonging, and the chance to build a future.Tune in for insightful discussions on shaping policies to uplift communities and #FightPoverty. Subscribe for more episodes wherever you listen to your podcasts.You can find transcripts and more episodes of "This Robin Hood Moment" at robinhood.org/podcasts.Thoughts? Guest suggestions? Email us at info@robinhood.org.Support Robin Hood’s work to elevate New Yorkers out of poverty at https://give.robinhood.org/give/61654/#!/donation/checkout?c_src=YT.LEARN MOREhttps://www.robinhood.org/https://www.facebook.com/robinhood/https://www.instagram.com/robinhoodnyc/https://www.linkedin.com/company/robin-hood/https://twitter.com/robinhoodnyc/

What happens when keeping your home means so much more than paying your rent?Keeping your home in New York City takes more than just paying the rent—it takes navigating an invisible maze of systems. Affordable child care, steady employment, timely public benefits, and support in moments of crisis all determine whether a family can hold on to housing long term. In this episode, we speak with Molly Wasow Park, Commissioner of the NYC Department of Social Services, about how she is reimagining the safety net to make it easier for New Yorkers to not only find housing but to keep it. From breaking down bureaucratic barriers to connecting families with the services they don’t even know exist, we explore what it really takes to stay home in the city.Tune in for insightful discussions on shaping policies to uplift communities and #FightPoverty. Subscribe for more episodes wherever you listen to your podcasts.You can find transcripts and more episodes of "This Robin Hood Moment" at robinhood.org/podcasts.Thoughts? Guest suggestions? Email us at info@robinhood.org.Support Robin Hood’s work to elevate New Yorkers out of poverty at https://give.robinhood.org/give/61654/#!/donation/checkout?c_src=YT.LEARN MOREhttps://www.robinhood.org/https://www.facebook.com/robinhood/https://www.instagram.com/robinhoodnyc/https://www.linkedin.com/company/robin-hood/https://twitter.com/robinhoodnyc/

What do you do when taking care of your health means putting your job on the line?For a Brooklynite like Wendell, getting sick came with a price he couldn’t afford. Without paid sick leave, every doctor’s visit meant lost wages—and the risk of falling behind on rent and bills. The result: a cycle of exhaustion, illness, and work that feels impossible to break.In this episode, Wendell shares his story of pushing through pain, navigating the city’s healthcare maze, and learning how to advocate for himself along the way. His story of becoming a NYC Care member captures the quiet courage of New Yorkers who keep the city moving while struggling to care for themselves in a system where healing too often comes at a cost.Tune in for insightful discussions on shaping policies to uplift communities and #FightPoverty. Subscribe for more episodes wherever you listen to your podcasts.You can find transcripts and more episodes of "This Robin Hood Moment" at robinhood.org/podcasts.Thoughts? Guest suggestions? Email us at info@robinhood.org.Support Robin Hood’s work to elevate New Yorkers out of poverty at https://give.robinhood.org/give/61654/#!/donation/checkout?c_src=YT.LEARN MOREhttps://www.robinhood.org/https://www.facebook.com/robinhood/https://www.instagram.com/robinhoodnyc/https://www.linkedin.com/company/robin-hood/https://twitter.com/robinhoodnyc/