Most leaders believe that scaling a team is a linear path to success. Ian Kraskoff learned the hard way that it’s often a trap.

In this episode, Ian Kraskoff (former leader at Uber and Loft) shares the raw, unfiltered story of building a team to 60 people, watching it nearly collapse, and the "hellish" process of scaling back down to 15 to save the company. We dive deep into why "throwing people at a problem" is the most expensive mistake a leader can make and how to transition from the "La La Land" of hyper-growth into the "Real World" of sustainable profit.

🕒 In this episode, we discuss:

• The 60-to-15 Reset: Why downsizing was the hardest—and best—decision Ian ever made for his culture.

• The O-Ring Theory: How tiny, microscopic flaws in your process can cause your entire organization to "explode" as you grow.

• Hiring "Only When it Hurts": Why hiring for expected growth is a recipe for disaster.

• Athletes of the Mind: Why top-tier leaders must view therapy and mental maintenance as a professional requirement.

• The "Neanderthal" Guide to AI: How Ian is using AI to teach himself to code and automating 65% of his business operations.

• The Fishbowl Habit: A simple, tactical way for busy founders to reclaim their weekends and protect their family life.
  
  Connect with Anugreh:

  LinkedIn: https://www.linkedin.com/in/anugrehsapra/

  Instagram: @anugreh

  Email for guest ideas: [email protected]

  #Leadership #SmallTeamLeadership #FounderJourney #ScalingBusiness #Fintech #LeadershipLessons #TeamsUnder100