Leadership Under 100

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.

• 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

Bernardo Riveros co-founded ILAC—one of Canada's most successful English language schools—growing it from three small classrooms and a simple brochure into an institution welcoming thousands of international students every year. What started as an immigrant's dream in Toronto became a thriving business empire.

Then, at its peak, he walked away.

In this raw and honest conversation, Bernardo shares the parts of success rarely discussed: the emptiness that can follow financial achievement, the toll on his marriage, the habits and environment that no longer aligned with his values, and the moment he realized money alone wasn’t enough. Through faith, a renewed focus on self-leadership, and a deep commitment to living with integrity, he chose a different path—one centered on his soul, his family, and true purpose.

Key takeaways for leaders of teams under 100:

• Why leading yourself first (habits, health, faith, relationships) is harder—and more important—than leading others
• The danger of measuring success only by revenue or growth
• How misalignment with core values quietly erodes even the most successful businesses
• The courage it takes to walk away from “everything you worked for” when it no longer serves your life
• Redefining success as 360°: thriving as a person, partner, parent, and leader—not just in the boardroom

Whether you're a founder scaling fast, a middle manager feeling the pressure, or anyone leading people while questioning “Is this worth it?”—this episode offers a powerful reminder that real leadership starts inside.

Timestamps:
0:00 – Intro & Bernardo’s immigrant journey to Canada
3:00 – From film dreams to starting ILAC with friends
8:00 – The scrappy early days: roommates, everything roles, miracles in Colombia
13:00 – When “startup spirit” becomes unsustainable
18:00 – Marriage struggles, faith awakening, and realizing something was missing
23:00 – The dark side of success: money came, but emptiness followed
27:00 – Self-leadership first: habits, health, values, and treating people well
31:00 – Redefining success as 360° (personal, family, business)
35:00 – Learning from John Maxwell: adding value in every interaction
38:00 – Final wisdom: align your business with your non-negotiable values

New here? Subscribe to Leadership Under 100 for practical conversations and honest breakdowns designed for founders, first-time leaders, middle managers, and department heads leading teams of 1–100 in any sector.

Connect with Anugreh:

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

Instagram: @anugreh

Email for guest ideas: [email protected]

What’s one value you refuse to compromise in your leadership or business? Drop it below—I read every comment. 👇

#Leadership #SelfLeadership #FounderJourney #ImmigrantSuccess #FaithInBusiness #WorkLifeBalance #ValuesDrivenLeadership #TorontoEntrepreneur #ILAC #CanadaBusiness

How does a 22-year-old from a small town in Brazil go from factory work to building and scaling a fintech company to over 100 people—and getting it acquired by one of Brazil's largest enterprises?

In this powerful conversation, Mike Allan shares his unfiltered journey: starting with zero tech background, landing an innovation grant that forced him to incorporate his first company, pivoting from hardware to banking-as-a-service infrastructure, navigating explosive growth, and leading through the chaos of 50–100+ employees.

Key lessons for leaders of teams under 100:

- How alignment shifts from casual chats to structured processes and SOPs

- The real challenges of leading older/more experienced people as a young founder

- Why being a constant example (hustle, long hours, getting hands dirty) builds unbreakable culture

- When to promote internally vs. hire externally—and the hidden costs of getting it wrong

- Focusing energy on your highest-leverage strengths (like a veteran soccer player choosing their ground)

Whether you're a first-time leader, founder scaling your first hires, middle manager dealing with org politics, or department head in any sector—this episode is packed with practical, hard-won insights on reducing bottlenecks, building trust, and leading through growth without losing the early-day energy.

Timestamps:

0:00 – Intro & Mike’s unexpected origin story

3:00 – From factory line to innovation grant: How the company was born

7:00 – Pivoting to payments infrastructure & massive Brazil fintech growth

11:00 – Scaling pain points: Alignment at 10 vs. 50 vs. 100 people

15:00 – Being the example: Hustle culture in scrappy startups

19:00 – Hiring mistakes: Promote vs. hire, and why internal often wins in niche markets

24:00 – Leading older teams as a young founder: Gaining respect & handling pushback

29:00 – What Mike would do differently next time (his new stealth startup)

34:00 – Final advice for young leaders: Don’t obsess over approval—be the standard

Connect with Anugreh:

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

Instagram: @anugreh

Email for guest ideas: [email protected]

Drop a comment: What’s the biggest scaling lesson you’ve learned so far? 👇

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

In this breakdown episode, I distill my conversation with leadership consultant Cameron McDonald into three practical lessons for teams under 100.

We cover how to define leadership in a way you can actually use, why training values matter just as much as training tasks, and how simple one-liners shape culture more than long documents ever will.

If you lead a small team and want clarity, consistency, and language that sticks—this one’s for you.

Free Gift (Job Profile Template): https://cameronlmcdonald.com/future-fit-job-profile

How do you create and protect culture as your team grows?

In this episode of Leadership Liftoff, I’m joined by Cam McDonald, leadership coach and former leader of a 100-person staff at a Leadership College, to talk about what founders need to know as they move from doing everything themselves to leading people.

We unpack what leadership really is, why culture can’t just live on a wall, and how small, everyday actions shape the health of your team.

Cam shares a simple, practical framework for building culture along with concrete examples founders can apply right away.

If you’re leading a team under 100 and figuring out how to scale without losing who you are, this episode is for you.

Free Gift (Job Profile Template): https://cameronlmcdonald.com/future-fit-job-profile

In this breakdown episode of Leadership Liftoff, we'll talk about three leadership lessons for teams under 100 drawn from a recent conversation with Luiz, one of the co-founders of the GigU App.

This episode explores how rituals shape culture, why fun makes leadership stick, and how empathy creates responsibility inside growing teams.

If you’re leading a small, scaling team and want leadership lessons you can actually use, this breakdown is for you.

As teams grow, many founders and leaders unknowingly become the bottleneck—every decision, hire, and conversation flows through them.

In this episode, Luiz Neves, co-founder of GigU, will share:

• Why founders and leaders often become the biggest constraint to scale
• How to move from “everyone follows the ball” to clear ownership and trust
• What empowered leadership actually looks like in teams under 100
• The hidden costs of urgency-driven hiring decisions
• How to build culture that keeps people aligned without constant oversight

Welcome to Episode Zero of Leadership Lift Off. If you're finding this podcast and want to know what it's about, start here.