Leap Academy with Ilana Golan

Episode 130: "Betting $250M on Women’s Sports: How Rejection Became Kara Nortman’s Superpower"

Release Date: October 21, 2025 | Guest: Kara Nortman

Episode Overview

In this engaging episode, Ilana Golan sits down with Kara Nortman—managing partner at Monarch Collective, co-founder of Angel City Football Club, and a trailblazer in women’s sports investment. The conversation dives deep into how Kara transformed personal curiosity into a $250 million wager on the future of women’s sports, why rejection became her "superpower," and the lessons she's learned as a leader, founder, community-builder, and venture capitalist. This episode is stacked with actionable wisdom for anyone looking to reinvent their career, build resilient ventures, or leap into uncharted professional territory.

Key Discussion Points & Insights

1. From Curiosity to Action: The Spark for Women's Sports Investment

• Personal Joy as a Compass: Kara’s journey began not as a business plan but as a deeply personal moment of realization at the 2015 Women’s World Cup with her family, which reignited her sense of fun and curiosity (03:00).
• Market Gap Discovery: The inability to buy a simple jersey after the match raised a profound question: "Why is there such massive demand but no way to participate as a fan?"

  "It’s like you have a 90-minute Gatorade commercial and then there’s no Gatorade in the store. But everyone told me I was the only one who wanted Gatorade." – Kara (04:00)

2. Turning Frustration into Market Research

• The “Joyful Irritation” Principle: Kara describes following her energy and serendipity—noticing the subjects you stay "joyfully irritated" about as a cue for deeper exploration (05:20).
• Proactive Curiosity: Instead of moving on, she began talking to players, unions, and stakeholders—what started as personal curiosity became informal but insightful market research (05:20–08:19).

3. Volunteering as a Path to Passion & Purpose

• Testing without Transactionality: Kara emphasizes the power of volunteering—using your time and skills as a way to assess genuine interest before making major leaps (08:19).
• Intrinsic Motivation:

  “We are so wired to think about efficiency and ROI… but sometimes the question is simply, ‘Where are you finding subtle pockets of joy or energy?’” – Kara (09:00)

4. Building Angel City FC: From “Impossible” to Breakout Success

• The Portfolio of Interests Approach: Kara illustrates the long, non-linear arc from 2015 curiosity to 2019’s Angel City launch. Success required letting interests marinate, staying open to serendipity, and seeking accountability partners (12:47–16:34).
• The Power of Diverse Collaboration: The founding team’s complementary skills—Kara, Julie Uhrman, Natalie Portman—were essential.

  "Finding people that you can walk with who inspire you, and knowing when to run through walls and take risk." – Kara (49:00)

• Innovative Ownership Structure: Instead of defaulting to traditional sports team models, Angel City was structured more like a tech startup—founders maintained significant equity and control (19:30–25:29).
• Facing—and Segmenting—Rejection: Raising capital involved facing constant skepticism and multiple last-minute turn-downs from investors (25:29–31:50).

  "There’s some rejection that’s comfortable for me, others that hurt every time I get it… if I believe in something, I’ll keep going." – Kara (29:33)

5. Resilience Through Rejection: Finding Growth in "No"

• Rejection as a Superpower: Kara reframes rejection as an inevitable part of aiming high and taking risks.

  "Every driven person eventually becomes in the rejection business. The bigger you're trying to aim, the more rejections you’re going to face." – Ilana (29:00)

• Segmenting Rejection: Kara suggests analyzing what types of rejection you find bearable—and which you need to build resilience against, whether in funding, relationships, or leadership (29:33–31:50).

6. Leaping Into and Across Worlds: From Venture Capital to Operating

• Choosing Experience over Comfort: Kara’s career spanned from Morgan Stanley to Battery Ventures to IAC/Urban Spoon, blending analytical rigor with operational drive.

  "Go get a skill that scales across both [finance and service]; you should follow your passions, but also ask, what skills span a lot of different things?" – Kara (32:26)

• Cold-calling and Board Roles: Early in her career, Kara pushed boundaries (and sometimes rules), learning to combine hustle with technical acumen—skills that translated directly into later ventures (35:00–39:10).

7. Operator vs. Investor Mindset

• Operationally-Oriented Investing: Kara highlights the difference between passive portfolio managers and hands-on, operational investors, noting her own preference and success in building companies as well as funds (39:31).
• Incubating Market-Moving Products: She tells the inside story of helping incubate Tinder at IAC, underscoring the satisfaction of building platforms that change industries (39:31–43:29).

8. Monarch Collective: Redefining Investment in Women’s Sports

• A New Kind of Investment Platform: Monarch Collective launched with a $250M fund—at the time, pioneering the dedicated investment in women’s sports teams, leagues, and rights (50:10–54:54).
• Building Cultural and Financial Value:

  "There’s no reason the women’s side couldn’t be bigger... We’re helping teams be more like Angel City, where we can come in as a large shareholder and help catalyze outcomes—cultural and financial." – Kara (50:10)

• Thesis-Driven, Relationship Focused: Monarch is intentional about building long-term partnerships and mapping out new sports and markets years in advance (55:02).

9. Building Teams, Building Trust

• All-Female Investment Firm (But Open-Minded): Monarch’s culture is built on collaboration, deep trust, and hiring both women and men using open, meritocratic processes (57:12).
• The Importance of Partnership:

  "Pick your partner well. People who help you move through the low moments and anxiety… Some days, just wake up and put one foot in front of the other and wait for the magic to show up." – Kara (58:29, 59:30)

Notable Quotes & Memorable Moments

• On Rejection as a Feature, Not a Bug:

  "You realize you’re in the rejection business. You get so much rejection. And I’m like, you’re right… I love getting rejection around our fund." – Kara (01:26 & 18:46)

• On Following Genuine Energy:

  "I was joyfully irritated and deeply curious… The things you’re talking about all the time—that’s your roadmap." – Kara (05:20)

• On Volunteering as Market Research:

  "Volunteering your time is an incredible way to assess if this is something you love to do more seriously." – Ilana (08:19)

• On Building a Legacy:

  "I was in a cathedral in Seville with my husband and daughters… I’m laying the brick in the middle of a cathedral that’s part of something bigger." – Kara (50:10)

• Advice to her younger self:

  “Operate out of abundance and not fear. Sit in the pain, don’t run away from something—run to something. Some days, just put one foot in front of the other and wait for the magic to show up.” – Kara (58:31)

Timestamps for Key Segments

• 03:00 – Kara describes discovering the gap in women’s sports as a fan
• 05:20 – The “Art of the Side Hustle” and finding passion via joyful irritation
• 08:19 – Importance of volunteering and exploring interests non-transactionally
• 12:47 – The slow, portfolio approach to building ventures and the role of serendipity
• 18:46 – Navigating relentless rejection while founding Angel City FC
• 25:29 – Hard lessons from fundraising and learning to segment rejection
• 32:26 – Early career as a woman in finance and the advice that shaped her journey
• 39:31 – Transitioning from investing to operating—hard lessons and growth
• 46:30 – Angel City’s commercial breakthrough; building community and culture
• 50:10 – The leap to Monarch Collective; building an industry-changing fund
• 55:02 – Monarch’s strategy for value creation and cultural leadership
• 58:29 – Kara’s advice to her younger self on abundance, collaboration, and courage

Episode Summary & Takeaways

Kara Nortman’s story is a masterclass in blending passion, patience, and operational excellence in pioneering new markets. Her advice on segmenting rejection, volunteering, and finding partners who lift you in low moments resonates for anyone seeking to leap in their own career or business. The episode is both an inspiring and practical guide for those wanting to build something bigger—whether a new venture, a personal brand, or a transformational community. The true lesson: lean into curiosity, don’t fear rejection, and be relentless in crafting joy and impact.