How Leaders Lead with David Novak

Episode #275: Ania Smith, CEO, TaskRabbit – Take risks that teach you something

Date: January 22, 2026
Guest: Ania Smith, CEO of TaskRabbit
Host: David Novak

Episode Overview

This episode features a conversation between David Novak and Ania Smith, CEO of TaskRabbit, focusing on leadership, risk-taking, personal growth, and building a bold, customer-centric culture. Ania shares her unique journey from immigrating to the U.S. at age 12 without knowing English, to holding leadership roles at Walmart, Uber, and Airbnb, ultimately leading TaskRabbit. The discussion unpacks lessons from immigrant grit, the value of discomfort, fostering boldness in organizations, evolving with technology (notably AI), and balancing ambition with family life.

Key Discussion Points & Insights

1. Early Lessons in Risk, Change, and Adversity

• Immigrant Roots Shaping Leadership

  • Ania moved from Poland to South Dakota at age 12, not speaking English.
  • Early jobs (paper route, door-to-door sales) built resilience:

    “Those lessons of sort of being told no over and over and over a thousand times stay with you really a lifetime... working through adversity are main lessons from those early days.” (05:10)

• Adaptation and Motivation

  • Having three kids with “very different” personalities taught her the importance of understanding unique motivations, both as a parent and as a leader.

    “Learning how to live through change and adversity and learning how to find your way in places that are very different, I think it’s a lesson...when we stay very comfortable, the learning ends up being a little bit less.” (01:41)

• Impact of Parental Sacrifice

  • Her father immigrating alone first instilled appreciation for sacrifice and empathy, now seen through the lens of being a parent herself. (07:44)

2. Risk-Taking: The Family Gap Year

• Taking the Leap

  • Ania’s gap year in Argentina with her family, pausing her career while at Airbnb:

    “Even though I was obviously somewhat concerned, I really felt that the learnings and the growth... the adventure, and having the time with our family... was well worth the effort.” (03:36)

• Planning, Courage, and Long-Term Perspective

  • The decision was meticulously planned (savings, logistics) and reinforced a philosophy of being intentional and “never too comfortable.”

3. Crucial Leadership Lessons from Career Milestones

• Consulting at Booz Allen

  • “Problems are very difficult and even people who are very, very smart don't necessarily have all answers.”
  • Value of tackling complex challenges and being “just a sponge, willing to do anything and really willing to learn a lot.” (12:18)

• Walmart: Navigating Big Company Culture

  • Learned to quickly identify decision-makers in large organizations to avoid misdirected effort and move with agility.

    “Understanding who has the power to make that decision is really important...in order to make any progress.” (13:48)

• Airbnb & Uber: Trust and Marketplace Matching

  • Listening deeply to customers builds organizational trust and reveals patterns.

    “There’s been no conversation I’ve had with a Tasker...or host from which I didn’t come away thinking about a problem maybe slightly different.” (15:18)

  • TaskRabbit is compared to Uber (matching needs to skills) but with more complex, less commodified tasks, emphasizing the importance of reliability and skill in “solving problems for people in their homes.” (16:40)

4. Building TaskRabbit: Leadership Philosophy in Practice

• Empathy for the Tasker

  • Ania’s immigrant experience gives her deep empathy for Taskers seeking to supplement income or build a new life. (18:23)
  • Shares a story of a Tasker who shifted from sales to painting via TaskRabbit, finding fulfillment and freedom.

    “It’s such a heartwarming story that we’re able to provide some sort of a path for people who are in between jobs or in between careers.” (20:13)

• Reducing Skepticism and Earning Trust

  • TaskRabbit relies on transparent reviews, high standards, and customer testimonials. (22:45)
  • “The way you know that is really by checking their reviews... you can read about the jobs that they have done.” (22:45)

• Experimentation and Failure

  • Failure is part of being bold—a core value of TaskRabbit culture:

    “If we're running experiments that do not fail, then we're probably not being bold enough.” (23:56)

  • Example: Testing whether customers want to choose their Tasker—results vary by category, and learning comes from failed assumptions.

• Deciding Amid Complexity

  • When faced with limited data:

    “Am I doing the right thing? ...Data often sort of doesn't tell you the why behind things.” (25:54)

  • Relies on experience (“your gut”) and favors making reversible decisions quickly over “analysis paralysis.”

5. Shaping a Bold, Nimble Culture

• Nurturing Boldness and Psychological Safety

  • Leaders need to create spaces where taking risks (and failing) is safe:

    “It is about being bold. It is about feeling safe enough to really try a lot of things that may or may not work...” (27:42, echoing 00:58)

  • Encourages fast decision-making and avoiding unnecessary bureaucracy as the company grows. (29:01)

• AI and Organizational Curiosity

  • Personally leverages AI (ChatGPT, Gemini) for productivity, brainstorming, and strategic thinking. Envisions AI supporting both employees (“Power Hour” trainings) and customers (using LLMs for better matching and experience).

    “What I'm really thinking a lot about is...how do we use large language models to help us drive revenue more...to help the customer have a better experience.” (30:08)

  • Fosters gradual adoption, acknowledging some staff are “reserved” about new technologies, but underscores inevitability of change. (32:03)

6. Self-Knowledge, Team Learning, and Recognition

• Best Fit for TaskRabbit

  • Considers TaskRabbit “home” due to confluence of skills in marketplaces, retail, and European operations—plus genuine passion. (33:21)
  • Loves seeing measurable impact in Tasker earnings (“we get to live that mission”).

    “Our mission is to transform lives one task at a time. And I feel that every day we get to live that mission.” (33:28)

• Ongoing CEO Learning Curve

  • Most difficult: Calibrating decision speed (“making some decisions too slow and others too fast”).
  • CEO’s role: Set vision, enable execution/culture, and communicate effectively.(35:16)

• Learning from Teams

  • Values disagreement (“disruptors” spur better thinking) and feedback as a “gift.”

    “Every day I learn from my team...not necessarily the same lessons—different people bring something different.” (36:50)

• Personalized Motivation

  • Recognizes that team members are motivated by different drivers.

    “Everyone on your team is likely motivated by very different things...it’s by far the most rewarding part of my job.” (38:02)

• Recognition & Being Heard

  • Most meaningful recognition: Being called on as a junior staffer, feeling heard:

    “Everyone wants to belong, and they want to feel heard. They want to feel like their contributions matter.” (39:12)

  • Most powerful recognition given: Praising creativity that was unconventional, giving “momentum to keep going.” (40:28)

7. Quick Hits: Lightning Round & Personal Rituals

• Describes herself as “Lively, curious and ambitious.”
• Would love to be “a dancer performer on stage.”
• Pet peeve: Indirect complaints (“Have you spoken to that person yet?”).
• Unique Polish tradition: “Schmingus Dingus” (water-dousing on Easter Monday).
• Most shaping leadership experience: Running a cashew plant in Kenya, learning “patience and grace.”
• Most creative TaskRabbit job: “Waiting in line for sample sales” (all-night tenting for exclusive shopping).
• Curiosity: Affordable housing/NIMBY vs. YIMBY, inspired by Ezra Klein’s “abundance” concept.
• Morning ritual: Reading long-form news journalism.
• Daily ritual: Working out—“very necessary.” (45:11)

8. Balancing Career and Family: The Point System

• Innovated a “point system” with her husband to ensure work-life balance:
  • Each job rated 1–3 based on intensity; the couple never exceeds a shared cap (ideally 4½ points).

    “If we are getting close to a 5, then one of us probably needs to make a change.”

  • Framework ensures prioritization of family, communication, and balance. (45:36)

9. Concluding Advice

• Advice to Aspiring Leaders:

  “Be curious and learn to listen.” (47:38)

Notable Quotes & Memorable Moments

• “Learning ends up being a little bit less when we stay very comfortable... It’s good to sometimes take ourselves out of the comfort zone.” — Ania Smith (01:41)
• “If we’re running experiments that do not fail, then we’re probably not being bold enough.” — Ania Smith (23:56)
• “What’s the right thing to do?... your gut to me is just the experience of having been in that situation before.” — Ania Smith (25:54)
• “Everyone wants to belong, and they want to feel heard... that was a great lesson very early in my career.” — Ania Smith (39:12)
• “Be curious and learn to listen.” — Ania Smith (47:38)

Timestamps for Key Segments

• 01:41 – Lessons from her gap year and adapting to change
• 03:36 – Taking the risk of a family gap year
• 05:10 – Childhood lessons in adversity and hard work
• 13:48 – Insights from leadership at Walmart
• 15:18 – Building trust at Airbnb and TaskRabbit
• 16:40 – Marketplace matching: Uber’s influence
• 20:13 – Heartwarming Tasker stories
• 23:56 – The value of failed experiments
• 25:54 – Decision-making under uncertainty
• 27:42 – Fostering boldness and psychological safety
• 29:01 – Avoiding bureaucracy while scaling
• 30:08 – Leveraging AI for leadership and operations
• 33:28 – Why TaskRabbit is the “right home”
• 35:16 – Biggest CEO learning curve
• 36:50 – Learning from her team
• 39:12 – The impact of being seen and heard
• 45:36 – The family “point system” for work-life balance
• 47:38 – Final advice: Curiosity and listening

Final Reflections & Takeaways

• Put yourself in new—and sometimes uncomfortable—environments to accelerate growth and self-awareness.
• “Customer obsession” is not just a phrase: being a product user herself, Ania ensures authentic feedback and trust in her leadership.
• True leadership means understanding and motivating people at an individual level, not just as a collective.
• Being bold means accepting—and even seeking—failure as a path to learning.
• Curiosity, self-awareness, and listening are fundamental leadership skills that open the door to innovation and trust.

This episode is a masterclass in integrating personal narrative, calculated risk, culture-building, and empathetic leadership, making Ania Smith’s journey and philosophy relevant far beyond TaskRabbit or the gig economy.