Podcast Summary: Work with Erika Ayers Badan

Episode: Kelly Bensimon on Real Housewives, Real Estate & Reinvention
Date: September 29, 2025
Host: Erika Ayers Badan
Guest: Kelly Killoren Bensimon

Episode Overview

In this episode, Erika Ayers Badan sits down with Kelly Killoren Bensimon—former Real Housewife, author, top-tier real estate broker, and serial reinventer. The conversation explores Kelly’s multifaceted career, navigating public perception, her approach to resilience, lessons in leadership, and the parallels between reality television, real estate, and personal growth. Throughout, the tone is candid, lively, and sharply observant, with both women sharing unfiltered insights on work, life, and the art of pivoting.

Key Discussion Points & Insights

1. Opening Thoughts on Compromise at Work

• [00:26 – 05:32]
  Erika reflects on the notion that “leadership is often about compromise” and how solutions at work rarely have a clear winner or loser:

  “Running a project and managing a team… is really about compromise. And being able to get to compromise is really important.” —Erika [03:15]

• She acknowledges that being in charge often means making decisions that leave everyone a bit dissatisfied, but that’s often a sign things are being handled right.

2. Current Work Trends and Challenges

• [05:32 – 15:00]
• Discussion of Gen Z’s financial behaviors:
  • 46% are already dipping into retirement savings, often to pay debt or address financial emergencies.
  • Erika walks through a real-time math exercise, calculating typical Gen Z savings and commenting on broader economic stresses:

    “I think it indicates a bigger challenge, which is people aren't saving, there is a lot of debt, and… there's some struggle, which is natural because you're in your 20s.” —Erika [07:25]

• Jamie Dimon's advice highlighted:
  • “Do not stay in your lane.”
  • Erika argues that maintaining a point of view and stepping outside “the way it’s always been done” is becoming more valuable.

3. Lessons from Legends: Ogilvy & Drexler

• [12:00 – 16:30]
• Erika shares learnings from a David Ogilvy memo on acknowledging your shortcomings:

  “I loved this… how great to have done something and then rethought the way you should do it.” —Erika [13:20]

• Praise for business maxims from Mickey Drexler (via an intern’s memo):
  “Scarcity sells,” “obsess over the details,” “constantly edit, edit, edit,” and more, asserting these are great rules for both business and self-growth.

4. Kelly Bensimon’s Approach to Work and Life

• [16:35 – 21:00]
• Kelly describes herself as “curious” and skilled at compartmentalizing:

  “I just was, you know, raised to work smart. And then enjoy your life.” —Kelly [16:56]

• Emphasizes multitasking is second nature; she’s always balanced multiple roles—modeling, writing, editing, and parenting simultaneously.

5. On Real Housewives: Survival and Reinvention

• [21:00 – 28:40]
• Kelly joined RHONY after her divorce to provide for her children and broaden her professional scope.

  “I went on Housewives because… I need to really make money for my children… and I wanted to widen my scope.” —Kelly [21:02]

• She discusses the culture shock of reality TV, the “dangerous, unexpected” dynamic, and being misunderstood or packaged negatively:

  “It was actually a really good lesson… I learned to just be much more cautious about who people are and where their energy lies and what they're thinking versus what I was thinking.” —Kelly [25:34]

6. On Self-Definition, Openness & Endurance

• [28:40 – 32:42]
• Kelly shares advice on navigating reinvention and public perception:

  “Always let your guard down… be open to things that are super uncomfortable. That's the genesis of emotional growth.” —Kelly [28:50]

• She stresses the importance of resilience and letting failure fuel progress:

  “Failure drives me. And when people tell me no, I'm like, oh, really? That's so nice for you. I'm just gonna do that better and even more better and better and better.” —Kelly [31:17]

7. Kelly’s Real Estate Philosophy & Strategy

• [34:33 – 44:03]
• Rejects the idea that her looks or background should limit her; flips negative perceptions (“you’re pretty, so you’re stupid”) on their head.
• Kelly’s “unconventional” approach:
  • Leveraged social to showcase new developments before most people were even thinking about them.
  • Uses narrative and visual storytelling skills from fashion/media to differentiate herself as a broker.
  • Shares anecdote of selling a $42 million property without a set price, demonstrating her instinctual, bold approach.

    “I had all these people from all over the world looking at all these new developments. That’s really kind of how it started.” —Kelly [38:17] “Ten days later, we sold it for $42 million. The number one deal downtown. No way. That’s amazing. From no price.” —Kelly [39:37]

• Notably fearless in adjusting tactics, including raising rents on properties and pulling listings to test new price points:

  “I just can’t wrap my head around that number for that area… I’m gonna take it off. And… a million dollars more… Three days later, we got an offer and we’re closing it next week.” —Kelly [43:29]

8. Embracing Change, Fearlessness, and the Gig Economy

• [41:06 – 44:03]
• Erika points out that Kelly embodies the gig economy and NIL (name, image, likeness) movement before they were buzzwords—having multiple roles, leveraging her brand, and cross-pollinating skills.
• Kelly on rejection:

  “If I don't try, I'll never know… I don't even think about rejection.” —Kelly [42:03]

• Describes herself as “mildly fearless,” which Erika notes would make a great T-shirt.

9. Being Real Online & Off

• [34:52 – 44:03]
• Kelly views her social media as a real, unfiltered journal—not curated for image, but genuinely documenting her day-to-day and highlighting her network.

Notable Quotes & Memorable Moments

• On Leadership & Compromise:

  “It’s actually only going well if everybody’s unhappy… ultimately running a project… is really about compromise.” —Erika [02:24]

• On Financial Reality:

  “Tapping into their 15 grand to pay for stuff… that's just the reality. That's like working in your 20s.” —Erika [07:02]

• On Reinvention:

  “You're always reinventing yourself… always uncharted territory, and you're trying to, like, navigate and make things great.” —Kelly [27:38]

• On Resilience:

  “If it's like, you know, I got slammed around a couple times, and you know, but I mean, that's called endurance.” —Kelly [27:11]

• On Failure:

  “Failure drives me… I'm always like, what are your thoughts? Criticize me… I want to move forward on that.” —Kelly [30:55]

• On Not Fearing Rejection:

  “If I don't try, I'll never know… I don't even think about rejection.” —Kelly [42:03]

• On Being Open:

  “Let your guard down… that's the genesis of emotional growth… emotionally and mindfully open to other people.” —Kelly [28:50]

• On Life & Work Philosophy:

  “I just was… raised to work smart. And then enjoy your life.” —Kelly [16:56]

• On Being ‘Mildly Fearless’:

  “I guess I'm kind of mildly fearless.” —Kelly [44:03] “Mildly fearless would be a great T shirt.” —Erika [44:07]

Important Segments & Timestamps

| Segment Topic | Timestamp Start | Notes | |----------------------------------------------|----------------|---------------------------------------------------------------| | Leadership & Compromise | 00:26 | Opening thoughts on compromise at work | | Gen Z & Retirement Savings | 05:32 | Financial pressure and literacy for young workers | | On ‘Staying in Your Lane’ | 09:00 | Jamie Dimon advice, challenging status quo | | Lessons from David Ogilvy & Mickey Drexler | 12:00 | Shortcomings & business rules | | Kelly on Work Ethic & Multitasking | 16:35 | Curiosity, compartmentalization, always doing multiple things | | Entry into Real Housewives | 21:02 | Motivation and impact of show | | Navigating TV & Public Perception | 23:30 | Preconceptions, pecking order, learning lessons | | Resilience and Reinvention | 27:09 | Endurance, core values, advice for others | | Failure & Growth Mindset | 30:34 | Kelly: “Failure drives me…” | | Real Estate Strategy & Social Media | 34:33 | Kelly’s unconventional tactics, leveraging her network | | Bold Real Estate Moves | 39:37 | $42M deal, raising prices, taking listings off market | | Embracing the Gig Economy | 41:06 | Multiplicity, branding, NIL (name, image, likeness) | | Fearlessness & Trying New Things | 42:03 | “I don’t even think about rejection.” |

Episode Highlights

- The Art of the Pivot

Kelly’s life is defined by adaptability—moving fluidly between careers, finding lessons in failure, and transforming public misperception into opportunity. She openly discusses her time on Housewives as both a practical move and a learning experience, emphasizing the value of being open, the ability to compartmentalize, and the drive to provide.

- Leveraging Old Skills in New Ways

Kelly explains how editorial and fashion skills translate directly to curating real estate, especially in a social media-driven age. Her methods are unconventional—leveraging visibility, narrative, and bold pricing strategies as unique differentiators.

- Modern Work Realities

The conversation ties back to current work culture: necessity of side hustles, using personal branding as leverage, and challenging norms. Both host and guest agree: having a point of view and flexibility are rare and valuable career qualities.

Memorable Closing

Erika and Kelly’s mutual admiration is evident, with talk of T-shirts (“mildly fearless”) and possibilities for further collaboration, both online and off. Kelly’s mantra for success—“Let your guard down, be open, be mildly fearless”—serves as both a summary and a call to action for listeners seeking their own reinvention.

For more unfiltered career and leadership insights, follow the Work podcast or visit Erika's Substack.