Best Manager Ever

Annie Riley
  • 5.0 (29)
  • CAREERS
  • UPDATED WEEKLY

Best Manager Ever reveals the secrets of successful management and empowers leaders to build winning teams. Join a community dedicated to sharing insights and stories from the most successful and beloved leaders in the startup world. All guests have been nominated as the “best manager ever” by a recent direct report. Before each interview, we go behind the guest’s back to collect feedback and stories from their team about what they’re *actually* like to work for. Then we sit down with the guest to unpack that feedback and to dig into their leadership playbook and lessons learned. Tune in, learn from the experts, and enhance your management skills while building meaningful connections throughout your career. Hosted on Acast. See acast.com/privacy for more information.

  1. Bad Meetings Are Disrespectful

    3D AGO

    Bad Meetings Are Disrespectful

    Meetings can be a real problem when they’re not run well or have the wrong people in them. Julia Bernstein, COO at Brightside Health joins Annie Riley to break down how she audits, redesigns, and even “dress rehearses” meetings to make them actually useful. From cutting unnecessary attendees to auditing recurring meetings regularly, Julia shares her no-BS approach to protecting time and driving results. Timestamps: 00:00 – Meet Julia Bernstein 02:00 – Translating business into people-first leadership 04:50 – Influencing without authority 06:30 – Managing diverse teams  07:15 – Building career ladders from day one 16:20 – Being involved vs informed 20:50 – The meeting audit: cutting what doesn’t work 24:50 – Designing better meetings  26:40 – Giving your team real ownership 27:20 – No one will set your boundaries for you 33:15 – Weekly rituals that keep teams aligned, human, and performing Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Julia Bernstein Nominate Your Best Manager Ever Best Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.

    49 min
  2. A Manager’s Word Has To Mean Something

    MAR 25

    A Manager’s Word Has To Mean Something

    What if the secret to great leadership is actually learning to say no? Annie Riley sits down with Gautam Prabhu, VP of Engineering at Scribe AI and longtime startup operator, to unpack his lessons from 25+ years of building teams at PagerDuty, Zendesk, and Opentrons. Gautam talks through why leaders should treat every “yes” as a promise, how winning teams are built through systems (not heroics), why a bad decision is better than no decision at all, and how he builds trust through honesty and accountability. Time Stamps: 00:00 Meet Gautam Prabhu 02:11 From engineer to accidental manager 05:04 Learning leadership the hard way 08:26 The two kinds of trust 12:03 Why intent matters first 15:42 Competence has to follow 19:18 Why great managers say no 23:57 A bad decision beats no decision 28:41 Startups can’t run on heroes forever 33:22 Building systems that scale 39:48 What great leadership really leaves behind Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Gautam Prabhu Nominate Your Best Manager Ever Best Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.

    55 min
  3. COO of Headspace: Why You Should Re-Recruit Yourself

    MAR 18

    COO of Headspace: Why You Should Re-Recruit Yourself

    What does it take to lead through 15 years of pivots, mergers, layoffs, and massive growth— without losing your people (or your mind!) along the way? Annie Riley sits down with Karan Singh, co-founder of Ginger and COO of Headspace, to unpack why great managers win people over through curiosity and genuine connection, how managers need to learn to ride the “J-curve” of change, and why everyone should re-recruit themselves to their role.  Timestamps: 00:00 Meet Karan Singh 04:30 Learning to manage on the fly 07:20 Winning people over 09:25 The mindset for surviving startup chaos 12:01 The j-curve of change 14:41 Speed vs. Space: giving teams time to process change 18:32 Healthy departures  22:24 Creating a “Next Play Plan”  26:49 Why you should re-recruit yourself 38:52 Rethinking PIPs: What most people get wrong  Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Karan Singh Nominate Your Best Manager Ever Best Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.

    50 min
  4. Welcome to Season 4

    SEASON 4 TRAILER

    Welcome to Season 4

    Best Manager Ever shares hard-earned leadership lessons from the very best and most successful managers in startups and tech. But here’s the twist: Every guest is endorsed by their team as the “best manager ever.” We talk to the guest’s direct reports to learn how they *really* lead, and then unpack that feedback live with the guest.  This season we’re leveling up with world-class experts who have spent their careers studying the science of leadership, including professors, authors, and coaches. Season 4 kicks off March 18th, with new episodes every Wednesday wherever you get podcasts. If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.com Join us on Substack  Connect with Annie Riley Check out Fort Light to level up your leadership skills Connect with our show’s Producer, Alexis Ramdaou Nominate your Best Manager Ever for the Podcast This is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

    2 min
  5. Best Manager Ever: Santa

    12/24/2025 ·  BONUS

    Best Manager Ever: Santa

    In this special holiday spoof episode of Best Manager Ever,  Annie Riley, host and founder of Fort Light, chats with the one and only Santa Claus! Known for spreading holiday cheer and managing a diverse team at the North Pole, Santa gives a rare interview about life behind the scenes. His direct reports, including elves and reindeer, praise Santa for his leadership, though they note he's their only manager ever ;)  We will dive into Santa's leadership style, the secrets behind the naughty and nice lists, and the challenges of maintaining the Christmas spirit all year long. Join us for a fun-filled episode with laughter and insight into the man behind the magic. Connect with Annie Riley Connect with our hilarious Santa, Jason Gore Listen to Jason’s podcast 108.9 The Hawk Check out Fort Light to level up your leadership skills Connect with our show’s producer Alexis Ramdaou Nominate your Best Manager Ever for the Podcast This is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

    13 min
  6. Best Manager Ever: Top Takeaways From Season 3

    12/17/2025

    Best Manager Ever: Top Takeaways From Season 3

    In this recap episode of Best Manager Ever, host Annie Riley reflects on standout lessons from Season 3. Annie discusses the six things our top manager guests have in common: high standards, clear communication, strong relationships with peers, a relentless focus on their own growth, a unique view of career management, and a human-first perspective.  It’s a chance to pause, look back, and notice what makes our guests so exceptional— and then think about how to apply those lessons in your own work.  Whether you're a longtime listener or just tuning in, this episode offers a meaningful recap of the themes that shaped our season.  Share your feedback and suggestions from the season in this super quick form, so we can make future episodes even better.  If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.com Join us on Substack  Connect with Annie Riley Check out Fort Light to level up your leadership skills Connect with our show’s Producer, Alexis Ramdaou Nominate your Best Manager Ever for the Podcast This is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

    20 min
  7. Best Manager Ever: Jared Erondu – Hard Mode Leadership

    12/10/2025

    Best Manager Ever: Jared Erondu – Hard Mode Leadership

    Jared Erondu is a seasoned design and startup leader, and is currently the Head of Design at early-stage startup Span. Jared spent eight years at Lattice rising from a solo designer pulling all-nighters in the early days, to leading a 50-person design organization and serving as GM across product and GTM as the company scaled. Earlier in his career, he was a design leader at Teespring and Omada Health. Jared is known for his design mentorship and community-building, and is an active advisor and angel investor.  Jared brings a calm, steady presence, especially during challenging times, always seeing the long view and providing unwavering support. His team appreciates his high standards, attention to detail, and commitment to craft, but also noted that he balances intensity with humor and approachability. In this episode, show creator and Fort Light founder Annie Riley sits down with Jared, and they discuss: Why all managers should master selective transparencyThe right way to communicate destabilizing intel How to recondition your mindset for “hard mode” leadershipHow to build a bench of resources to support yourself  The best way to recruit exceptional talent Why managing your own mindset is the ultimate leadership unlock  If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.com Join us on Substack  Connect with Jared Erondu Connect with Annie Riley Check out Fort Light to level up your leadership skills Connect with our show’s Producer, Alexis Ramdaou Nominate your Best Manager Ever for the Podcast This is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

    52 min
  8. Best Manager Ever: Dana Lawson - Conquering Imposter Syndrome and Fostering Team Resilience

    12/03/2025

    Best Manager Ever: Dana Lawson - Conquering Imposter Syndrome and Fostering Team Resilience

    Dana Lawson is the CTO of Netlify. She’s been a technologist for decades, and was previously the VP of Engineering at Github and the Director of Engineering at New Relic, Heptio, InVision (acquired by Miro), and more. Dana has a diverse background, and served in the military.  Dana's direct reports praise her for building confidence, providing autonomy support, for bringing honesty and compassion, and for sponsorship that goes beyond mentorship.  In this episode, show creator and Fort Light founder Annie Riley sits down with Dana, and they discuss: How imposter shows up at senior levels– and how to handle it  How to deal with interpersonal conflictsWhat it takes to be an effective sponsorThe importance of embracing change If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.com Join us on Substack  Connect with Dana Lawson Connect with Annie Riley Check out Fort Light to level up your leadership skills Connect with our show’s Producer, Alexis Ramdaou Nominate your Best Manager Ever for the Podcast This is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

    44 min
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Trailer

5
out of 5
29 Ratings

About

Best Manager Ever reveals the secrets of successful management and empowers leaders to build winning teams. Join a community dedicated to sharing insights and stories from the most successful and beloved leaders in the startup world. All guests have been nominated as the “best manager ever” by a recent direct report. Before each interview, we go behind the guest’s back to collect feedback and stories from their team about what they’re *actually* like to work for. Then we sit down with the guest to unpack that feedback and to dig into their leadership playbook and lessons learned. Tune in, learn from the experts, and enhance your management skills while building meaningful connections throughout your career. Hosted on Acast. See acast.com/privacy for more information.

Information

  • Creator
    Annie Riley
  • Years Active
    2024 - 2026
  • Episodes
    52
  • Rating
    Explicit
  • Copyright
    © Annie Riley
  • Show Website
    Best Manager Ever

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