She's So Lucky – "How to Win When People Underestimate You with Taylor Rooks"

Host: Les Alfred
Guest: Taylor Rooks (Sports journalist, producer, nonprofit founder)
Release Date: October 21, 2025

Episode Overview

This episode features a rich, energizing conversation between Les Alfred and Taylor Rooks focused on the central theme: how women can create their own luck, turn underestimation into opportunity, and thrive in male-dominated spaces. Taylor shares personal stories of persistence, seizing opportunity, and how she leveraged qualities unique to her womanhood in her career. The two dive deep into topics of self-trust, managing external feedback, the impact of “expanders,” and how challenges as both Black and female identities can be reframed as assets.

Key Discussion Points & Insights

1. Creating Your Own Luck

• Taylor's "Lucky" Moments:
  • Macro Level: Taylor describes 2025 as her "luckiest year"—she just got married and landed her dream job.

    "I feel like I'm living in just, like, the luckiest year of my life." (03:13)

  • Micro Level (Persistence Pays Off):
    Taylor, at 19, relentlessly emailed the NBA for media credentials, finally resulting in access to All Star Weekend. There, a fateful interview with Kevin Durant kickstarted a professional and personal relationship, which came full circle when Taylor was chosen to interview Durant live on stage as his trade news broke.

    "I just kept emailing until I could get to someone... and they said yes." (05:57)
    "The luck that I created with the relationship with KD, but then the real luck of Shams not having WiFi on his flight and the timing, aligning." (05:36)

2. Qualities Required for Success in Male-Dominated Fields

• Intuition vs. External Opinions:
  Taylor discusses learning to trust her intuition and internal vision over external projections or limitations—especially when venturing into new spaces.

  "It's very easy to become other people's projections... There are just things that I think happen because of osmosis." (08:22)

• Confidence and Preparation:
  She attributes much of her success to confidence in her own voice, dedicated preparation, and caring about the quality of her work.

  "Being confident in just what you believe and what you think... caring about the work that you're doing, dedicating to the work that you're doing that day." (07:34)

• Turning Underestimation into Fuel:
  Taylor reframes being underestimated as a source of motivation and believes qualities like warmth, empathy, and emotional intelligence give women an edge in sports media.

  "There are a lot of things that I believe make me good at my job because of my experience as a woman..." (25:04)

3. The Role of “Expanders”

• Taylor credits “expanders”—mentors and supporters who believed in and advocated for her—for every major step in her career.
  • Example: Cameraman Clem introducing her to a Big Ten Network executive led directly to her first job.

    "I owe my career to just the expanders... Everyone, you know, owes it to someone that believed in them." (11:12)

• Les shares how peer expanders (peers a step ahead) have helped normalize greater ambitions for her.

  "Spending time around people who have higher expectations of themselves and their experiences has helped me have higher expectations." (13:21)

4. Dealing with the Fear of “The Other Shoe Dropping”

• Both women discuss the persistent anxiety that joy or success will be interrupted, and how it can be self-protective but limiting.
  • Taylor emphasizes the need to name and challenge these feelings.

    "Now I really start to think about just having a large capacity for goodness... I'm always thinking I don't deserve this, like, good, happy joy that I'm feeling right now." (19:41)

  • Les counters with positive practices like "Best Case Scenario Journaling."

    "In the morning, I’ll write how I want the day to go, assuming best case scenarios… I feel like my life has completely changed in the past two years that I’ve been doing it." (21:36, 21:55)

5. Navigating Male-Dominated Spaces in Sports

• Challenges:
  Taylor enumerates hurdles: persistent doubt, oversexualization (especially for Black women), and navigating external projections of capability.

  "Being a woman in sports, where there are a lot of males that work in it, also male sports fans... It's your orbit, it's men, men, men, men." (24:54)

• Reframing Obstacles as Opportunities:
  She highlights the advantages her womanhood gives her: warmth, trust, emotional intelligence, a holistic view, and the power to tell fuller stories.

  "I always really begin this conversation by saying how much I enjoy being a woman and that there are a lot of things that I believe make me good at my job because of my experience as a woman..." (25:04)

6. Impact of Social Media & Sexualization

• Taylor shares how over-sexualization mainly manifests online, and why she detached from caring about social media commentary for her wellbeing and longevity.

  "Social media will ruin you if you care too much about it... you can't read them, you can't make their comments change what you do or don't do." (33:16)

• Notably, she addresses how the internet attributes her on-air success to her looks, which she finds deeply dismissive.

  "It makes no sense. But it's also super demeaning because... you're attributing the successes that I'm having to things that are incredibly irrelevant." (35:25)

7. Shifting Perspectives on Women's Sports

• Taylor underscores that media should "meet the moment" and ensure people covering women's sports are equipped with proper expertise and context, not just celebrity or outsider status.

  "You should have people behind the mics and in front of the camera that are educated on the sport... for this moment." (50:34)

• Advocates for telling full stories about women athletes—not just about their womanhood, but about their craft and lives as athletes.

  "You're never really interviewing LeBron James about being a male athlete... And this is what these women have worked for their entire lives." (52:37)

• Notes societal bias in interpreting women's actions as gendered, highlighting the need for greater media self-awareness.

  "If a woman commits a hard foul, she didn't do that because she doesn't like a player. She did it because it's basketball..." (52:46)

8. Taylor’s New Show and Leadership Approach

• Taylor shares excitement for her new role as host of Amazon Prime's NBA show—a dream come true and an opportunity to build something from the ground up.

  "It is a dream job. It is every single thing that I feel like I have ever worked for, I get to do it with the best team..." (42:14)

• Prioritizes authentic interpersonal relationships and chemistry as foundational to both on-air success and leadership.

  "The number one priority is creating that culture where you like each other, where you want to talk about basketball together..." (49:54)

9. Her Nonprofit Work

• Taylor recently launched the Taylor Wicks Foundation, which focuses on specific, practical support for individuals and communities, like donating supplies to teachers and girls’ clubs.

  "Through different things that I care about and stories that I’ve heard... Sometimes people just need help with a thing. Something that is direct and tangible." (55:22)

Notable Quotes & Memorable Moments

• On Persistence:
  "I just kept emailing until I could get to someone… and they said yes. Different time. I don't know if that would happen now."
  —Taylor Wicks (05:57)

• On Self-Trust:
  "It's very easy to become other people's projections… which is why what you tell yourself, you have to say that as often as you might hear its counterpart."
  —Taylor Wicks (08:22)

• On Expanders:
  "Everyone, you know, owes it to someone that believed in them. So that has absolutely, absolutely happened."
  —Taylor Wicks (11:12)

• On the Other Shoe Dropping:
  "Why is it that I'm always thinking I don't deserve this, like, good, happy joy that I'm feeling right now?"
  —Taylor Wicks (19:41)

• On the Power of Womanhood:
  "Those are all things that I credit a lot of my success in the space to… But again, I think you really always have to lead with, again, the good."
  —Taylor Wicks (26:07)

• On Social Media:
  "Social media will ruin you if you care too much about it... The only people that you should care about what they have to say are your close friends, your family, most importantly people that are paying you."
  —Taylor Wicks (33:16)

Timestamps for Key Segments

• [03:13] – Taylor’s big luck story and the Kevin Durant moment
• [05:36] – The magic of persistence and seizing opportunity
• [07:34] – Confidence, intuition, and the importance of preparation
• [10:46] – The impact of expanders and mentorship
• [13:21] – Les on peer expanders and normalizing big ambitions
• [19:41] – Addressing the anxiety that “the other shoe will drop”
• [24:54] – Women in sports: challenges and reframing them as advantages
• [33:16] – Navigating social media negativity/sexualization
• [42:14] – Taylor’s new NBA show at Amazon and leading a team
• [50:34] – Evolving coverage and attitudes around women’s sports
• [55:22] – The Taylor Wicks Foundation: goals and launch

Conclusion

This episode is an inspiring roadmap for turning being underestimated into advantage, the value of relentless self-trust, and the power of women supporting women. Taylor Rooks illustrates, through vivid stories and actionable insights, how to persist, prepare, and leverage the unique strengths of womanhood to succeed—even (or especially) when you're underestimated. The conversation is warm, honest, and filled with practical wisdom for anyone seeking to create their own luck and rise above others’ limited expectations.

Where to Watch / Learn More:

• Taylor's sports coverage: Thursday Night Football (Sept 11) & NBA show (Oct 24) on Amazon Prime
• Taylor Wicks Foundation: Instagram: @TaylorFoundation | Web: TaylorRooks.com/foundation