How Leaders Lead with David Novak

Episode #259: Sarah Gibson Tuttle, Founder and CEO of Olive & June – Work on Yourself

Release Date: October 2, 2025

Episode Overview

This episode features David Novak in conversation with Sarah Gibson Tuttle, Founder and CEO of Olive & June, the brand redefining the at-home nail care industry. The discussion explores Sarah's personal journey from corporate finance to entrepreneurship, the creation and purpose behind Olive & June, her approach to leadership and self-awareness, and insights into building a business that disrupts a category while staying true to its community. The episode closes with actionable leadership advice, candid reflections on personal growth, and a post-interview analysis with co-host Kula.

Key Discussion Points & Insights

1. Personal Journey and Early Influences

• Childhood Themes: Sarah reflects on her upbringing, highlighting moments that shaped her leadership, including her strict father who disliked nail polish, leading to her sneaking manis as a form of self-expression.

  "Nails has always been my go to. When my nails were done, when they were painted, I felt like I could take on the world." – Sarah (03:32)

• Coping & Confidence: She describes how manicures became a grounding ritual, providing confidence whether as a teenager or in her first finance job as a philosophy major out of her depth.

  “I always felt a little bit...scared of things...but when my nails were done, I felt really like a full person and I could do anything.” – Sarah (03:56)

2. Transition from Finance to Entrepreneurship

• Wall Street Years: Sarah shares her decade-long career as an equity trader, driven by family influence and excelling under pressure, but ultimately feeling unfulfilled.
  • Key skills learned: High standards (07:04), time sensitivity, balancing internal vs external clients.
  • On “that moment” she knew she needed change:

    “I was waking up thinking, can I sleep in today? Can I say I'm sick? When I'm a bad version of myself...I know I'm in the wrong place.” – Sarah (10:54)

• Journey to Pivot: Realization set in gradually ("a slow evolution"), with Selena describing external and internal factors (job/marriage dissatisfaction) converging before the founding insight arrived.

3. The Genesis and Growth of Olive & June

• Lightbulb Moment: Inspired by a stellar Dry Bar experience and a lackluster nail salon visit, Sarah saw the need for an elevated, joyful nail experience.

  “Why don't they have this for nails?...It takes time to marinate a bit...but that leads to the best decisions.” – Sarah (12:44)

• Brand Purpose: Launching as a salon chain and pivoting to at-home products, Olive & June aims to democratize salon-quality nails and make everyone feel their best "at an affordable price."
  • Distinction: Focus on accessibility, education, and community.
  • Education via "Olive University":

    “Not only do you have the best products...but you also have this education. And we do it in a ton of different ways, whether...long form [or] snackable content...That’s the voice you’re receiving it in.” – Sarah (16:10)

4. Branding & Decision-Making

• Name Story: The brand is named after Sarah’s grandmother (June) and great-grandmother (Olive), honoring family roots and embracing a unique, non-obvious name strategy.

  “If they don’t know what it is, then I haven’t done my job right.” – Sarah (17:48)

• Processing Feedback: Sarah prefers "no people" in her circle for honest critique, actively filters valued feedback, and adjusts strategy after independent research.
  • Example: Adjusted polish pricing after advice from advisor Brian Sugar (20:06).

5. Leadership, Letting Go, and Culture

• Scaling Up: Hardest part of scaling was relinquishing creative control and trusting her team, reminding herself “I’m just an n of 1” in a vibrant, diverse community (22:14).
• Experimentation & Failure: Sarah fosters a culture where it’s safe to err, modeling vulnerability and emphasizing learnings over perfection.

  “Perfection is boring... I think there’s a lot of beauty in the imperfection.” – Sarah (31:00)

6. Self-Awareness & Personal Growth

• Working on Yourself: Sarah credits therapy, active feedback-seeking, and reflection for her self-awareness—an example she hopes to set, especially for her daughter.

  “The only way that you become the best version of yourself is...it’s not just one thing or one process. It’s if everyone in your life...plus you’re open to it.” – Sarah (33:12)

• Resilience & Openness: She advocates for ongoing evolution and viewing growth as a gift, not a chore.

7. Crisis-Era Growth & Community Connection

• COVID-19 Response: Olive & June's at-home mani system was launched a year before the pandemic, positioning them for explosive (16x) growth when salons closed.
  • Daily Instagram Lives helped support and educate new users, keeping the brand close to its community in a time of need.

  “People need the support and the pep talk in order to get the confidence to try something.” – Sarah (27:29)

8. Social Media, AI, and Metrics

• Social as Inspiration: Sarah views social media not as a conversion engine, but as a channel for delight, education, and brand-building, believing “if you build it, they will come” (28:41).
• AI’s Role: Used for operational help and brainstorming, but not core product development (29:47).

9. Personal Tidbits – Lightning Round (36:40-39:26)

• Descriptive Words: Loyal, loving, enthusiastic.
• Person for a Day: Great-grandmother Olive—"one beer and one cigarette every day...life of the party."
• Biggest Pet Peeve: People saying, “I tried my best.”
• Favorite Taylor Swift Era: Reputation (“badass” vibe).
• Self-Care Ritual: TikTok scrolling in bed, post-daughter bedtime.
• Most Prized Possession: Great-grandmother’s engagement ring, worn as a necklace.
• Relaxation: More chill than she appears.

10. Leading at Home and Vision

• Parenting Approach: Advocates structure, boundaries, and fun, balancing strictness with joy (41:36).
• Dream Come True: Feels grateful for her current life, but aspires for Olive & June to become the number one nail brand globally and is committed to “not leaving anything on the field.”

11. Advice for Aspiring Leaders (42:44)

“You can’t escape hard work. Hard work and putting in the time and...effort...Nothing can be done without true hard work.” – Sarah (42:44)

Notable Quotes & Memorable Moments

• On Finding Purpose:

  “When I’m a bad version of myself...I know I’m in the wrong place.” – Sarah (10:54)

• On Letting Go:

  “We hire amazing people to do their jobs, let them do it in the best way possible and see what the results are.” – Sarah (23:16)

• On Community:

  “Community is not just a word at Olive & June. It's the heart and soul of our business." – Sarah (22:34)

• On Therapy and Growth:

  “I want to live it to the best of my ability. But also, my daughter is 10. How do I model for her what real growth and evolution looks like?” – Sarah (35:21)

• On Self-Awareness:

  "The only way you can ever grow is to really know who you are and know what your capabilities are." – David (47:22, debrief)

• On Preparation vs. Luck:

  “But I think the reality is, if we hadn’t had the right products...it would have been a flash in the pan. And that’s why we’ve been able to scale.” – Sarah (26:18)

• On Making an Impact:

  “Don’t ever underestimate what feeling good about yourself can do for a business.” – Kula (54:04, debrief)

Noteworthy Timestamps

• Reflections on Childhood and Nails as Confidence: 02:25–04:47
• Transition Out of Finance: 10:11–12:15
• Olive & June Origin Story: 12:34–14:27
• Explosive COVID Growth & Community Support: 25:32–27:29
• Letting Go of Creative Control: 22:14–23:48
• Advice for Leaders: 42:44

Debrief: Post-Interview Analysis with Kula and David

In the episode wrap-up, co-host Kula and David Novak reflect on:

• The importance of self-awareness in leadership (“Know yourself to grow yourself”).
• How Sarah’s pivot out of finance demonstrates courage and self-knowledge (47:22).
• Tips for navigating major career changes without burning bridges (48:39).
• The value of personal confidence rituals—like nail care or fitness routines—in enhancing leadership effectiveness (51:11–54:04).
• The power of a differentiated brand rooted in personal story and authenticity.

Actionable Takeaways

• Self-Reflection: Regularly assess personal fulfillment and energy in your current role.
• Community Focus: Innovate for the user and remain in constant dialogue with your community.
• Feedback Loops: Cultivate honest truth-tellers and process criticism thoughtfully.
• Growth Mindset: Embrace feedback, therapy, and mistakes as part of becoming a better leader.
• Hard Work & Consistency: There is no substitute for hard work and grinding toward mastery.

This episode provides insightful, relatable lessons on self-knowledge, resilience, and driving consumer-focused innovation—ideal for established and aspiring leaders alike.