School of Hard Knocks Podcast

Guest: Kendra Scott | From Single Mom & College Dropout to Billion-Dollar Entrepreneur

Date: October 24, 2025
Host: The School of Hard Knocks (James, Jack, Josh)
Featured Guest: Kendra Scott, Founder of Kendra Scott Jewelry

Episode Overview

This episode tells the remarkable story of Kendra Scott—the journey from being a single mother and college dropout who started a jewelry business at her bedroom card table, to becoming the founder of a billion-dollar omnichannel retail brand. Through candid storytelling and hard-won insights, Kendra shares her foundational beliefs, stories of early struggle, how she built company culture, how she approaches mentorship, and her perspective on purposeful entrepreneurship, fundraising, and enduring success.

Key Themes & Discussion Points

1. Humble Beginnings and Mindset

Timestamps: 01:23–04:48

• Starting out small:
  Kendra didn’t set out to create a billion-dollar company. Her goal was to provide for her family while being present as a mom.
  • “When I started, I wasn't saying, oh, I'm going to build a billion dollar company out of my bedroom. ...I wanted to create a business that allowed me to provide for my family, but also allow me to be a mother first….” (02:40)
• Previous failures:
  Her first business at age 19—a hat shop—failed. She was hesitant to make a big announcement about her new jewelry venture due to fear of being laughed at.
• Day-by-day confidence:
  She focused on small wins:
  • “Each day that I'd get a win, I'd get an order and get another order. It was like, okay, a little bit more of that confidence built….” (03:50)
• Purpose-driven foundation:
  Early on, philanthropy was part of her brand: making jewelry for silent auctions, donations—her core values: Family, Fashion, and Philanthropy.

2. Integrating Family and Business Values

Timestamps: 04:48–06:06, 41:00–43:16

• Putting family first, always:
  At Kendra Scott, being a mom comes before CEO duties—for Kendra and her employees.
  • “Everybody that works in my business knows that I'm a mom first before I'm a CEO, before I'm chairwoman. My kids, my family, they come first. I want the people that work for me, for their kids and their family to come first.” (05:02)
• Unique company culture:
  Headquarters has a kids’ play area, nursing rooms, and an environment that truly supports families.
  • “We've created an environment where we support family and that is something that's super magical and I hope can be a North Star for other businesses and brands.” (06:03)
• Core values as North Star:
  Company values guide hiring, partnerships, and daily work.
  • “Because it's your North Star... If you don't know your purpose, your why, and who you are, who you really want to work with, what is your brand doing for this world?” (41:08)

3. Overcoming Early Challenges and Asking for Help

Timestamps: 06:06–09:23, 12:12–14:35

• Early resource constraints:
  All products were handmade; shipping big orders from the dining room; involving friends and family.
• Breakthrough moment:
  The first major order: 1,500 units, $75k from Harold’s.
  • She didn’t know how she’d fulfill it, and reached out to Bill Fields (former Walmart CEO) for manufacturing help.
• The power of the network:
  • “As an entrepreneur, asking for help is not a sign of weakness, people. It is the greatest sign of strength.” (08:22)
• Relationship-building strategy:
  • “Remember, you give what you get... Be really thoughtful about how you approach people. ...Have one strategic question where they can really make an impact. You're being thoughtful of their time, and I promise you, most people will give you that five minutes.” (13:22)

4. Building in Austin, Texas & The Power of Non-Coastal Markets

Timestamps: 09:23–12:12

• Austin’s unique DNA:
  Stubbornly built the brand outside of New York/LA; Austin’s culture, supportiveness, and creativity fueled growth.
  • “Austin became part of the DNA of our brand. ...We didn’t look like anybody else because we were influenced by the place we were in.” (09:44)
• Serving overlooked markets:
  Focusing on Texas, Midwest, and the South unlocked a huge, loyal customer base.
  • “Go where your customers are, especially when you're trying to be scrappy. ...I needed to be in Plano, Texas. That's where my customer was.” (20:47)

5. Strategic Growth and Innovations in Retail

Timestamps: 14:35–22:52

• Retail pivot catalyzed by crisis:
  The 2008 recession forced the shift from wholesale to direct-to-consumer, opening the first Kendra Scott store in 2010.
  • “It was the greatest gift our business ever had. ...I had given all the power of my business to other people. ...We need to focus on direct to consumer.” (14:51)
• Stores as living labs:
  Flagship stores doubled as company offices, fostering real-time feedback and innovation.
  • “...A laboratory. It is a place for you to learn and be a sponge every day. Stand in those stores, see what your customers are attracted to... We were learning from our customer and we were making better products every Day because we had that little laboratory.” (17:18)
• Smart, data-driven expansion:
  Expansion was fueled by customer data—opening in markets with existing strong demand rather than chasing “vanity” locations.
  • “10 year plans are ridiculous. Nobody should be doing a 10 year plan. ...I was able to take that data and those metrics to be able to figure out out where would the next place be.” (20:47)

6. Fundraising: Discipline & Values Over Dollars

Timestamps: 22:52–30:05

• Getting the right investors:
  Kendra prioritized alignment of values, not just dollar amounts.
  • “Not all money is good money... Do not work with them, period. Stop. ...Every single partner I've ever worked with, I always say, okay, how did they make me feel when I'm with them? ...It’s not about just checks, folks, because the right humans will make those checks become so much bigger.” (28:24)
• Advisory board before investors:
  She formed a board of advisors early for accountability and to gain expertise.
• First major investment:
  Her mentor Steve Hicks invested $5 million, which grew almost 10-fold; more importantly, he became a trusted, values-aligned partner.
  • “He's like a second dad to me. I just, I love him so much and I love our friendship and I value it so much and I've learned so much from him over the years.” (28:04)

7. What Investors (and Kendra) Look for in Founders

Timestamps: 30:05–34:53

• Passion and traction over theory:
  • “You gotta have More than just an idea. You've gotta have some proven results, period. ...Why this business? Because if you're just doing it to get a billion dollar brand and put money in your pocket, you're not gonna survive. Honey, you gotta have passion, you gotta have drive, you have to have purpose…” (30:43)
• Bootstrapped, scrappy mindset:
  Prefers entrepreneurs who “stretch a dollar,” have discipline, and are open and humble.
• Vulnerability & authenticity:
  • “Vulnerability is so powerful in today's world. Authenticity is so powerful. Be your most authentic, vulnerable self, and it will go so far in everything, not just business, in friendships and relationships.” (34:53)
• Not faking it:
  It’s okay to admit where you are struggling; real stories (like her mom answering Nordstrom’s calls for “Shipping & Receiving”) are part of the journey.

8. Building & Scaling Teams and Culture

Timestamps: 39:03–41:00

• Collaboration over ego:
  • “It's never been an I, it's been a we from day one. ...The DNA of Kendra Scott is every single person who touches this brand every day.” (39:36)
• Hiring & partnering for core values:
  All hires, vendors, and partners must align with the core values: family, fashion, philanthropy.
  • “If they do not share your core values and your heart, do not work with them, period. Stop.” (28:24)

9. Lifelong Learning, Mentorship & Giving Back

Timestamps: 43:42–52:13

• New horizons:
  Created the Kendra Scott Women’s Entrepreneurial and Leadership Institute at UT Austin—to inspire and empower other entrepreneurs (including men).
• Mentorship through example and community:
  Kendra stresses learning from others, being part of EO (Entrepreneurs Organization), and constantly reading business books. She highlights mentorship comes by seeking—books, videos, networks, not just in-person.
• Experience as the true teacher:
  • “Get your hands dirty, you gotta do it to learn it. We don’t learn just by sitting and watching people… you gotta roll your sleeves up, you gotta get in business…” (46:11)

10. Reflection, Legacy, and Advice

Timestamps: 52:13–54:25

• Core hiring lesson:
  • “I would definitely tell her [young Kendra] hire on heart. ...the best people on paper are not always the best people for your business.” (52:21)
• Guiding Principle—Living With Purpose:
  • “We’ve got a very small grain of sand time on this earth and take that time to go, why am I here? What is my purpose? And how can I make a positive impact on the people and the world around me?” (53:15)
• How She Wants to Be Remembered:
  • “I hope that I'm remembered as a woman who gave younger girls hope that it doesn't matter... you can achieve anything in this world when you put your mind to it and don't let anybody tell you different.” (53:54)

Notable Quotes

• “You have to ask for help. As an entrepreneur, asking for help is not a sign of weakness, people. It is the greatest sign of strength.” — Kendra Scott (08:22)
• “If you don't know your purpose, your why, and who you are, who you really want to work with, what is your brand doing for this world? ...In order to create culture, you have to have core values.” — Kendra Scott (41:08)
• “Not all money is good money... Do not work with them, period. Stop.” — Kendra Scott (28:24)
• “Get your hands dirty, you gotta do it to learn it. ...Experience, experience, experience. ...Your worst boss is gonna be your best boss. Cause they're gonna teach you exactly the kind of leader you don't want to be.” — Kendra Scott (46:11)
• “Hire on heart. ...The best people on paper are not always the best people for your business.” — Kendra Scott (52:21)
• “We've got a very small grain of sand time on this earth... How can I make a positive impact on the people and the world around me? If you can do that, you will live a life that is full and happy.” — Kendra Scott (53:15)
• “I hope that I'm remembered as a woman who gave younger girls hope that ...you can achieve anything in this world when you put your mind to it and don't let anybody tell you different.” — Kendra Scott (53:54)

Memorable Moments

• Kendra’s story about pretending to have a ‘Shipping and Receiving’ department—her mom acting as the department on Nordstrom’s calls. (35:24)
• Describing the shock of transitioning from almost going bankrupt to building a billion-dollar brand—that “the only B word I had really known before that was potential bankruptcy.” (01:28)
• The applause from her MIT entrepreneurship peers when she introduced herself as a single mom, college dropout, and proud graduate of “the school of hard knocks”—catalyzing a more authentic conversation among high-achievers. (37:08)
• Discussion of giving back—her creation of women’s entrepreneurship programs and the Yellow Rose lifestyle brand as a love letter to Texas. (43:42–47:57)

Recommended Listening Order (Timestamps)

• Humble Beginnings (01:23–04:48)
• Family & Company Culture (04:48–06:06)
• Overcoming Challenges (06:06–09:23)
• Austin Roots & Scale (09:23–14:35)
• Retail Expansion (14:35–22:52)
• Fundraising and Values (22:52–30:05)
• What Investors Want (30:05–34:53)
• Vulnerability & Team-Building (34:53–41:00)
• Legacy, Mentorship, and Last Advice (52:13–54:25)

For anyone seeking inspiration, practical entrepreneurial wisdom, and a testament to the power of values-driven business, this is a must-listen conversation with one of America’s most admired founders.